Water-soluble complexes, which have herbicidal utility, can be formed from urea and alkali metal salts of selected sulfonylureas, e.g., chlorsulfuron.

BACKGROUND OF THE INVENTION 
Sulfonylurea herbicides are well-known in the art. Such herbicides are 
often utilized in agriculturally suitable solvents. It is desirable to 
maximize the amount of sulfonylurea herbicide which can be dissolved in 
such a solvent so that one may make maximum use of the sulfonylurea 
herbicide. 
Sulfonylurea herbicides are well-known in the art; there does not appear to 
be a teaching, however, to the formation of water-soluble complexes 
between urea, and urea derivatives with alkali metal salts of such 
sulfonylureas. 
According to this invention it has unexpectedly been discovered that such 
complexes may be formed. 
The complexes are more soluble in agriculturally suitable solvents which 
represents distinct advantages over the art; such as rapid formation of 
solutions for spraying, and higher concentrations of active ingredient in 
such solutions. 
The comlexes also possess hydrolytic stability. 
SUMMARY OF THE INVENTION 
This invention pertains to products obtained by the process of contacting 
sulfonylurea salts of Formula I with ureas of Formula II under complexing 
conditions in a ratio of about 1:1, when m is 1, and about 1:2, when m is 
2, to compositions containing said products and to their method-of-use as 
pre- and/or postemergence herbicides or plant growth regulants. 
##STR1## 
wherein R is 
##STR2## 
R.sub.1 is H or CH.sub.3 ; R.sub.2 is F, Cl, Br, C.sub.1 -C.sub.4 alkyl 
optionally substituted with 1-3 atoms of F or Cl, SO.sub.2 NR.sub.6 
R.sub.7, S(O).sub.n R.sub.8, SO.sub.2 NCH.sub.3 (OCH.sub.3), CO.sub.2 
R.sub.9, OSO.sub.2 R.sub.10, OR.sub.11, NO.sub.2, C.sub.2 -C.sub.4 
alkenyl, CONR.sub.6 R.sub.7, phenyl, 
##STR3## 
R.sub.3 is H, F, Cl, Br, CH.sub.3, OCH.sub.3 or CF.sub.3 ; R.sub.4 is Cl, 
NO.sub.2, CO.sub.2 R.sub.10 ; 
R.sub.5 is Cl, Br, SO.sub.2 NR.sub.6 R.sub.7, S(O).sub.n R.sub.10, CO.sub.2 
R.sub.10, C.sub.1 -C.sub.3 alkyl, NO.sub.2, CON(CH.sub.3).sub.2 or 
SO.sub.2 N(OCH.sub.3)CH.sub.3 ; 
R.sub.6 is H or C.sub.1 -C.sub.3 alkyl; 
R.sub.7 is H or C.sub.1 -C.sub.2 alkyl; 
R.sub.8 is C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkyl substituted 
with 1-5 atoms of F, Cl or Br; 
R.sub.9 is C.sub.1 -C.sub.4 alkyl, CH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 
CH.sub.2 Cl or CH.sub.2 CH.dbd.CH.sub.2 ; 
R.sub.10 is C.sub.1 -C.sub.3 alkyl; 
R.sub.11 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.3 alkyl substituted with 
1-5 atoms of F, Cl or Br, CH.sub.2 CH.dbd.CH.sub.2 or CH.sub.2 C.tbd.CH; 
R.sub.12 is H, C.sub.1 -C.sub.12 alkyl, C.sub.3 -C.sub.6 cycloalkyl or 
C.sub.3 -C.sub.6 alkenyl; 
R.sub.13 is H, CH.sub.3 or CH.sub.2 CH.sub.3 or R.sub.12 and R.sub.13 may 
be taken together to be --(CH.sub.2).sub.4 -- or --(CH.sub.2).sub.5 -- or 
R.sub.1 and R.sub.12 may be taken together to be --(CH.sub.2).sub.2 --; 
R.sub.14 is C.sub.1 -C.sub.3 alkyl, F, Cl, Br, NO.sub.2, CO.sub.2 R.sub.10, 
SO.sub.2 N(CH.sub.3).sub.2, SO.sub.2 R.sub.12, or phenyl; 
R.sub.15 is H, C.sub.1 -C.sub.3 alkyl, or CH.sub.2 CH.dbd.CH.sub.2 ; 
R.sub.16 is H or CH.sub.3 ; 
R.sub.17 is H or CH.sub.3 ; 
n is 0 or 2; 
M is an alkali metal cation, magnesium or calcium; 
Z is CH or N; 
X is CH.sub.3, OCH.sub.3 or OCHF.sub.2 ; 
Y is CH.sub.3, OCH.sub.3, CH(OCH.sub.3).sub.2, OCHF.sub.2, C.sub.2 H.sub.5, 
OC.sub.2 H.sub.5, OCH.sub.2 CF.sub.3 or CH.sub.2 OCH.sub.3 ; and 
m is 1 or 2. 
Preferred for reasons of their expected higher herbicidal activity and/or 
more favorable ease of synthesis and/or improved stability of compositions 
containing them are: 
(1) complexes of the generic scope containing sulfonylurea salts of Formula 
I 
wherein 
R is 
##STR4## 
R.sub.2 is Cl, CH.sub.3, SO.sub.2 N(CH.sub.3).sub.2, S(O).sub.n R.sub.8, 
CO.sub.2 R.sub.9, OSO.sub.2 R.sub.10, OR.sub.11, NO.sub.2 or 
CON(CH.sub.3).sub.2 ; 
R.sub.3 is H, Cl, CH.sub.3, OCH.sub.3 or CF.sub.3 ; 
R.sub.8 is C.sub.1 -C.sub.3 alkyl, CF.sub.3, CF.sub.2 H or CF.sub.2 
CF.sub.2 H; 
R.sub.9 is C.sub.1 -C.sub.4 alkyl; and 
R.sub.11 is C.sub.1 -C.sub.4 alkyl, CF.sub.3, CF.sub.2 H, CF.sub.2 CF.sub.2 
H or CH.sub.2 CH.sub.2 Cl; 
(2) complexes of the generic scope containing the urea of Formula II 
wherein R.sub.1, R.sub.12 and R.sub.13 are H; 
(3) complexes of the preferred 1 where the sulfonylurea salt of Formula I 
is selected from the salts of: 
2-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]benz 
oic acid, methyl ester; 
2-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoic acid, 
methyl ester; 
2-chloro-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]benzenesul 
fonamide; 
2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonylmethyl]benzoic 
acid, methyl ester; 
5-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-1-methyl-1H-p 
yrazole-4-carboxylic acid ethyl ester; 
2-(2-Chloroethoxy)-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonylb 
enzenesulfonamide; and 
3-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]-2-t 
hiophene-carboxylic acid, methyl ester. 
(4) complexes of the preferred 3 containing the urea of Formula II where 
R.sub.1, R.sub.12 and R.sub.13 are H; 
(5) products of the generic process prepared from sulfonylurea salts of 
Formula I wherein R is 
##STR5## 
R.sub.2 is Cl, CH.sub.3, SO.sub.2 N(CH.sub.3).sub.2, S(O).sub.n R.sub.8, 
CO.sub.2 R.sub.9, OSO.sub.2 R.sub.10, OR.sub.11, NO.sub.2 or 
CON(CH.sub.3).sub.2 ; 
R.sub.3 is H, Cl, CH.sub.3, OCH.sub.3 or CF.sub.3 ; 
R.sub.8 is C.sub.1 -C.sub.3 alkyl, CF.sub.3, CF.sub.2 H or CF.sub.2 
CF.sub.2 H; 
R.sub.9 is C.sub.1 -C.sub.4 alkyl; and 
R.sub.11 is C.sub.1 -C.sub.4 alkyl, CF.sub.3, CF.sub.2 H, CF.sub.2 CF.sub.2 
H or CH.sub.2 CH.sub.2 Cl; 
(6) products of the generic process prepared from ureas of Formula II 
wherein 
R.sub.1 is H; 
R.sub.12 is C.sub.2 -C.sub.6 alkyl; and 
R.sub.13 is H; and 
(7) products of the preferred 5 where the sulfonylurea salt is selected 
from the salts of: 
2-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]benz 
oic acid, methyl ester; 
2-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoic acid, 
methyl ester; 
2-chloro-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]benzenesul 
fonamide; 
2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonylmethyl]benzoic 
acid, methyl ester; 
5-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-1-methyl-1H-p 
yrazole-4-carboxylic acid, ethyl ester; 
2-(2-chloroethoxy)-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl] 
benzenesulfonamide; and 
3-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]-2-t 
hiophenecarboxylic acid, methyl ester. 
DETAILED DESCRIPTION OF THE INVENTION 
This invention relates to novel reaction products of sulfonylurea salts of 
Formula I with ureas of Formula II, to the process for preparing them, to 
compositions containing them and to their method-of-use as pre- and 
postemergence herbicides or plant growth regulants. Agriculturally 
suitable salts of Formula I are also useful herbicides and can be prepared 
by a number of ways known to the art. For example, a metal salt of Formula 
I can be made by contacting the corresponding conjugate acid with a 
solution of an alkali or alkaline earth metal salt having an anion 
sufficiently basic to neutralize at least 95% of the conjugate acid (e.g., 
hydroxides, alkoxide, carbonate or hydroxide). 
Salts of Formula I can also be prepared by exchange of one cation for 
another. Cationic exchange can be effected by direct reaction of a 
solution of a salt of Formula I with a solution containing the cation to 
be exchanged. This method is most effective when the desired salt 
containing the exchange cation has acceptably low solubility in the 
solvent and can be separated by filtration. 
Exchange may also be effected by passing an aqueous solution of a salt of 
Formula I through a column packed with a cation exchange resin containing 
the cation to be exchanged. In this method, the cation of the resin is 
exchanged for that of the original salt and the desired product is eluted 
from the column. 
The ureas of Formula II can be prepared by a number of ways well-known in 
the art. The simplest compound, urea, is commercially produced by reacting 
carbon dioxide and ammonia. Substituted ureas can be prepared by reacting 
primary or secondary amines with potassium cyanate or with urea in a 
water-free acid such as glacial acetic acid. Also, alkyl isocyanates or 
carbamoyl chlorides may be reacted with ammonia to give substituted ureas 
of Formula II. Additionally, substituted ureas useful in this invention 
can be made by reacting primary and secondary amines with esters of 
carbamic acid such as methyl or ethyl carbamate. 
The products of this invention formed by reacting the sulfonylurea salts of 
Formula I where m is 1 or Formula I where m is 2 with ureas of Formula II 
where R.sub.1 is hydrogen or methyl and R.sub.12 and R.sub.13 are hydrogen 
have been found to be 1:1 and 1:2 molar complexes respectively. That is, 
when a salt of Formula I where m is 1 and a urea of Formula II where 
R.sub.1 is hydrogen or methyl and R.sub.12 and R.sub.13 are hydrogen are 
mixed in any molar proportion in a suitable solvent, the product which 
forms and is isolated contains an equimolar amount of each reactant. When 
a salt of Formula I, where m is 2 and a urea of Formula II where R.sub.1 
is hydrogen or methyl and R.sub.12 and R.sub.13 are hydrogen are mixed in 
any molar proportions in a suitable solvent, the product which forms and 
is isolated contains a 1:2 molar amount of the sulfonylurea and urea 
reactants. Solvents suitable for the preparation of complexes are any that 
will dissolve a sufficient amount of a sulfonylurea salt and urea compound 
to enable complete reaction to occur within an acceptable period of time, 
e.g., 5 minutes to 2 hours. These include water, alcohols such as 
methanol, ethanol and 2-propanol, ketones such as acetone, methyl isobutyl 
ketone, and methyl ethyl ketone, acetonitrile, tetrahydrofuran, 
.gamma.-butyrolactone and N-methylpyrrolidone. In order to readily isolate 
a complex, the solvent preferably is one in which it has low solubility. 
For example, sodium salts of a number of sulfonylureas and urea are 
appreciably soluble in methanol but complexes formed are not. 
Alternatively, if solutions of complexes are desired, a good solvent for 
the complex is required. Complexes of lithium salts of most sulfonylureas 
and methylurea are fairly soluble in .gamma.-butyrolactone, for example. 
In general, lithium salts contribute more to complex solubility in any 
solvent than sodium salts and methylurea gives much improved solubility 
over urea. 
Techniques for preparing complexes are relatively simple. A preformed metal 
salt of a sulfonylurea of Formula I prepared as described above may be 
mixed with a urea compound in a solvent or a sulfonylurea and equivalent 
amounts of a basic alkali or alkaline earth metal salt and a urea compound 
may be combined in any order in a solvent. Reaction to produce complexes 
is rapid, generally occurring to completion within 1-15 minutes. 
Products of this invention formed by reacting the sulfonylurea salts of 
Formula I where m=1 with the ureas of Formula II where at least one of 
R.sub.1, R.sub.12 and R.sub.13 is other than hydrogen or methyl or two of 
R.sub.1, R.sub.12 and R.sub.13 are other than hydrogen also are complexes 
but exhibit somewhat different behavior than those prepared using the 
ureas of Formula II where R.sub.1 is hydrogen or methyl and R.sub.12 and 
R.sub.13 are hydrogen. Complexes prepared from sulfonylurea salts of 
Formula I where m is 1 and the more highly substituted and/or higher alkyl 
substituted ureas under the complexing conditions described above in a 
ratio of about 1:1 have exceptionally high solubility in a variety of 
solvents and are not isolatable. Lithium salts contribute more to 
solubility than sodium salts, longer straight chain alkyl groups on ureas 
contribute more than substituents which are branched and solubility 
increases with chain length. Attempts to isolate complexes may result in 
complex dissociation. 
Complex formation between sulfonylurea salts of Formula I where m is 1 and 
ureas of Formula II where at least one of R.sub.1, R.sub.12 and R.sub.13 
is other than hydrogen or methyl or two of R.sub.1, R.sub.12 and R.sub.13 
are other than hydrogen is shown by the fact that sulfonylurea salts which 
are virtually insoluble in a solvent are rapidly solubilized upon addition 
of the urea in an equal or greater molar proportion. For example, sodium 
salts of many sulfonylureas are slightly soluble in acetone but, when 
combined with n-butylurea, dissolve to an extent greater than 50%. 
Products of this invention formed by reacting the sulfonylurea salts of 
Formula I where m is 2 with the ureas of Formula II where one of R.sub.1, 
R.sub.12 and R.sub.13 is other than hydrogen or methyl or two of R.sub.1, 
R.sub.12 and R.sub.13 are other than hydrogen afford 1:2 complexes which 
like the complexes with ureas of Formula II where R.sub.1 is hydrogen or 
methyl and R.sub.12 and R.sub.13 are hydrogen are isolatable. 
The products of this invention have been shown to have herbicidal activity 
equivalent to that of precursor sulfonylurea salts of Formula I as well as 
their corresponding conjugate acids. They may be formulated into a number 
of agriculturally acceptable forms such as solutions, oil suspensions, 
aqueous suspensions, wettable powders and granules. 
The complexes are desirable products for agricultural usage because they 
are readily soluble in water and can be rapidly dissolved in preparing 
solutions for spraying. 
Solutions of complexes from selected sulfonylurea salts and ureas in 
agriculturally suitable organic solvents can be prepared in higher 
concentrations than those of the sulfonylurea salts themselves and their 
corresponding conjugate acids. Stability of the sulfonylureas in these 
complexes in organic solvents is significantly improved compared to that 
of the same sulfonylureas as salts or conjugate acids in the same 
solvents. This enables formulations of solutions relatively stable in 
storage to be prepared. 
The formulations of this invention may contain about 1 to 50%, (preferably 
10 to 40%) of the complexes of sulfonylurea salts of Formula I and ureas 
of Formula II. Compositions may contain more than one complex. 
Compositions may also optionally contain other herbicides. The following 
herbicides are examples of materials which may be particularly useful in 
such combinations: 
______________________________________ 
Common Name Chemical Name 
______________________________________ 
acifluorfen 5-[2-chloro-4-(trifluoromethyl)- 
phenoxy]-2-nitrobenzoic acid 
alachlor 2-chloro-2',6'-diethyl-N--(methoxy- 
methyl)acetanilide 
ametryn 2-(ethylamino)-4-(isopropylamino)- 
6-methylthio)- .sub.-s-triazine 
amitrole 3-amino- .sub.-s-triazole 
AMS ammonium sulfamate 
asulam methyl sulfanilylcarbamate 
atrazine 2-chloro-4-(ethylamino)-6-(isopropyl- 
amino)- .sub.-s-triazine 
barban 4-chloro-2-butynyl .sub.--m-chlorocarbanilate 
benefin N--butyl-N--ethyl-.alpha.,.alpha.,.alpha.-trifluoro-2,6- 
dinitro- -p-toluidine 
bensulide O,O--diisopropyl phosphorodithioate, 
S--ester with N--(2-mercaptoethyl)- 
benezenesulfonamide 
benzipram 3,5-dimethyl-N--(1-methylethyl)-N-- 
(phenylmethyl)benzamide 
benzoylprop Ethyl N--benzoyl-N--(3,4-dichlorophen- 
oxy)-DL-alaninate 
bifenox methyl 5-(2,4-dichlorophenoxy)-2- 
nitrobenzoate 
bromacil 5-bromo-3- ---sec-butyl-6-methyluracil 
bromoxynil 3,5-dibromo-4-hydroxybenzonitrile 
butachlor N--(butoxymethyl)-2-chloro-2',6'- 
diethylacetanilide 
butam 2,2-dimethyl-N--(1-methylethyl)-N-- 
phenylmethyl)propanamide 
buthidazole 3-[5-(1,1-dimethylethyl)-1,3,4-thia- 
diazol-2-yl]-4-hydroxy-1-methyl-2- 
imidazolidinone 
butralin 4-(1,1-dimethylethyl)-N--(1-methyl- 
propyl)-2,6-dinitrobenzenamine 
cacodylic acid 
hydroxydimethylarsine oxide 
carbetamide D-N--ethyllactamide carbanilate (ester) 
CDAA N,N--diallyl-2-chloroacetamide 
CDEC 2-chloroallyl diethyldithiocarbamate 
chloramben 3-amino-2,5-dichlorobenzoic acid 
chlorbromuron 
3-(4-bromo-3-chlorophenyl)-1-methoxy- 
1-methylurea 
chloroxuron 3-[ -p-( -p-chlorophenoxy)phenyl]-1,1- 
dimethylurea 
chlorpropham 
isopropyl .sub.--m-chlorocarbanilate 
cisanilide --cis-2,5-dimethyl-N--phenyl-1-pyrroli- 
dinecarboxamide 
CMA calcium methanearsonate 
cyanazine 2-[[4-chloro-6-(ethylamino)- .sub.-s-triazin- 
2-yl]amino]-2-methylpropionitrile 
cycloate S--ethyl N--ethylthiocyclohexanecarbamate 
cycluron 3-cyclooctyl-1,1-dimethylurea 
cyperquat 1-methyl-4-phenylpyridinium 
cyprazine 2-chloro-4-(cyclopropylamino)-6-(iso- 
propylamino)- .sub.-s-triazine 
cyprazole N--[5-(2-chloro-1,1-dimethylethyl)- 
1,3,4-thiadiazol-2-yl]cyclopropane- 
carboxamide 
cypromid 3',4'-dichlorocyclopropanecarboxanilide 
dalapon 2,2-dichloropropionic acid 
dazomet tetrahydro-3,5-dimethyl-2H--1,3,5- 
thiadiazine-2-thione 
DCPA dimethyl tetrachloroterephthalate 
desmetryn 2-(isopropylamino)-4-(methylamino)-6- 
methylthio)- .sub.-s-triazine 
diallate S--(2,3-dichloroallyl)diisopropylthio- 
carbamate 
dicamba 3,6-dichloro- -o-anisic acid 
dichlobenil 2,6-dichlorobenzonitrile 
dichlorprop 2-(2,4-dichlorophenoxy)propionic acid 
diclofop 2-[4-(2,4-dichlorophenoxy)phenoxy]pro- 
panoic acid 
diethatyl N--(chloroacetyl)-N--(2,6-diethylphen- 
yl)glycine 
difenzoquat 1,2-dimethyl-3,5-diphenyl-1H--pyrazolium 
dinitramine N.sup.4,N.sup.4 --diethyl-.alpha.,.alpha.,.alpha.-trifluoro-3, 
5- 
dinitrotoluene-2,4-diamine 
dinoseb 2- ---sec-butyl-4,6-dinitrophenol 
diphenamid N,N--dimethyl-2,2-diphenylacetamide 
dipropetryn 2-(ethylthio)-4,6-bis(isopropylamino)- 
.sub.-s-triazine 
diquat 6,7-dihydrodipyrido[1,2-.alpha.:2',1'-c]- 
pyrazinediium ion 
diuron 3-(3,4-dichlorophenyl)-1,1-dimethyl- 
urea 
DSMA disodium methanearsonate 
endothall 7-oxabicyclo[2.2.1]heptane-2,3-dicar- 
boxylic acid 
erbon 2-(2,4,5-trichlorophenoxy)ethyl 2,2- 
dichloropropionate 
ethafluralin 
N--ethyl-N--(2-methyl-2-propenyl)-2,6- 
dinitro-4-(trifluoromethyl)benzen- 
amine 
ethofumesate 
(.+-.)-2-ethoxy-2,3-dihydro-3,3-dimethyl- 
5-benzofuranyl methanesulfonate 
fenac (2,3,6-trichlorophenyl)acetic acid 
fenuron 1,1-dimethyl-3-phenylurea 
fenuron TCA 1,1-dimethyl-3-phenylurea mono(tri- 
chloroacetate) 
flamprop N--benzoyl-N--(3-chloro-4-fluorophenyl)- 
DL-alanine 
fluchloralin 
N--(2-chloroethyl)-2,6-dinitro-N-- 
propyl-4-(trifluoromethyl)aniline 
fluometuron 1,1-dimethyl-3-(.alpha.,.alpha.,.alpha.-trifluoro- .sub.--m- 
tolyl)urea 
fluorodifen -p-nitrophenyl .alpha.,.alpha.,.alpha.-trifluoro-2-nitro- 
-p-tolyl ether 
fluridone 1-methyl-3-phenyl-5-[3-(trifluoro- 
methyl)phenyl]-4(1H)--pyridinone 
fosamine ethyl hydrogen (aminocarbonyl)phos- 
phonate 
glyphosate N--(phosphonomethyl)glycine and agri- 
culturally suitable salts thereof 
hexaflurate potassium hexafluoroarsenate 
hexazinone 3-cyclohexyl-6-(dimethylamino)-1- 
methyl-1,3,5-triazin-2,5(1H,3H)--dione 
ioxynil 4-hydroxy-3,5-diiodobenzonitrile 
isopropalin 2,6-dinitro-N,N--dipropylcumidine 
karbutilate ---tert-butylcarbamic acid ester with 3- 
( .sub.--m-hydroxyphenyl)-1,1-dimethylurea 
lenacil 3-cyclohexyl-6,7-dihydro-1H--cyclo- 
pentapyrimidine-2,4(3H,5H)--dione 
linuron 3-(3,4-dichlorophenyl)-1-methoxy-1- 
methylurea 
MAA methanearsonic acid 
MAMA monoammonium methanearsonate 
MCPA [(4-chloro- -o-tolyl)oxy]acetic acid 
MCPB 4-[(4-chloro- -o-tolyl)oxy]butyric acid 
mecoprop 2-[(4-chloro- -o-tolyl)oxy]propioninc acid 
mefluidide N--[2,4-dimethyl-5-[[(trifluoro- 
methyl)sulfonyl]amino]phenyl]- 
acetamide 
methalpropalin 
N--(2-methyl-2-propenyl)-2,6-dinitro- 
N--propyl-4-(trifluoromethyl)benzenamide 
metham sodium methyldithiocarbamate 
methazole 2-(3,4-dichlorophenyl)-4-methyl-1,2,4- 
oxadiazolidine-3,5-dione 
metoachlor 2-chloro-N--(2-ethyl-6-methylphenyl)-N-- 
(2-methoxy-1-methylethyl)acetamide 
metribuzin 4-amino-6- ---tert-butyl-3-(methylthio)- 
as-triazin-5(4H)one 
molinate S--ethyl hexahydro-1H--azepine-1-carbo- 
thioate 
monolinuron 3-( -p-chlorophenyl)-1-methoxy-1-methyl- 
urea 
monuron 3-( -p-chlorophenyl)-1,1-dimethylurea 
monuron TCA 3-( -p-chlorophenyl)-1,1-dimethylurea 
mono(trichloroacetate) 
MSMA monosodium methanearsonate 
napropamide 2-(.alpha.-naphthoxy)-N,N--diethylpropionamide 
naptalam N--1-naphthylphthalamic acid 
neburon 1-butyl-3-(3,4-dichlorophenyl)-1- 
methylurea 
nitralin 4-(methylsulfonyl)-2,6-dinitro-N,N-- 
dipropylaniline 
nitrofen 2,4-dichlorophenyl -p-nitrophenyl ether 
nitrofluorfen 
2-chloro-1-(4-nitrophenoxy)-4-(tri- 
fluoromethyl)benzene 
norea 3-(hexahydro-4,7-methanoindan-5-yl)- 
1,1-dimethylurea 
norflurazon 4-chloro-5-(methylamino)-2-(.alpha.,.alpha.,.alpha.-tri- 
fluoro- .sub.--m-tolyl)-3(2H)--pyridazinone 
oryzalin 3,5-dinitro-N.sup.4,N.sup.4 --dipropylsulfanilamide 
oxadiazon 2- ---tert-butyl-4-(2,4-dichloro-5-isopro- 
poxyphenyl).DELTA..sup.2 -1,3,4-oxadiazolin-5-one 
oxyfluorfen 2-chloro-1-(3-ethoxy-4-nitrophenoxy)- 
4-(trifluoromethyl)benzene 
paraquat 1,1'-dimethyl-4,4'-bipyridinium ion 
PBA chlorinated benzoic acid 
pendimethalin 
N--(1-ethylpropyl)-3,4-dimethyl-2,6- 
dinitrobenzenamine 
perfluidone 1,1,1-trifluoro-N--[2-methyl-4-(phenyl- 
sulfonyl)phenyl]methanesulfonamide 
picloram 4-amino-3,5,6-trichloropicolinic acid 
procyazine 2-[[4-chloro-6-(cyclopropylamino)- 
1,3,5-triazine-2-yl]amino]-2-methyl- 
propanenitrile 
profluralin N--(cyclopropylmethyl)-.alpha. ,.alpha.,.alpha.-trifluoro- 
2,6-dinitro-N--propyl- -p-toluidine 
prometon 2,4-bis(isopropylamino)-6-methoxy- 
.sub.-s-triazine 
prometryn 2,4-bis(isopropylamino)-6-(methyl- 
thio)- .sub.-s-triazine 
pronamide 3,5-dichloro(N--1,1-dimethyl-2-propyn- 
yl)benzamide 
propachlor 2-chloro-N--isopropylacetanilide 
propanil 3',4'-dichloropropionalide 
propazine 2-chloro-4,6-bis(isopropylamino)- .sub.-s- 
triazine 
propham isopropyl carbanilate 
prosulfalin N--[[4-(dipropylamino)-3,5-dinitro- 
phenyl]sulfonyl]-S,S--dimethyl- 
sulfilimine 
prynachlor 2-chloro-N--(1-methyl-2-propynyl)- 
acetanilide 
secbumeton N--ethyl-6-methoxy-N'--(1-methylpropyl)- 
1,3,5-triazine-2,4-diamine 
siduron 1-(2-methylcyclohexyl)-3-phenylurea 
simazine 2-chloro-4,6-bis(ethylamino)- .sub.-s-triazine 
simetryn 2,4-bis(ethylamino)-6-(methylthio)- .sub.-s- 
triazine 
TCA trichloroacetic acid and its salts 
tebuthiuron N--[5-(1,1-dimethylethyl)-1,3,4-thia- 
diazol-2-yl]-N,N'--dimethylurea 
terbacil 3- ---tert-butyl-5-chloro-6-methyluracil 
terbuchlor N--(butoxymethyl)-2-chloro-N--[2-(1,1- 
dimethylethyl)-6-methylphenyl]acetamide 
terbuthylazine 
2-( ---tert-butylamino)-4-chloro-6-(ethyl- 
amino)- .sub.-s-triazine 
terbutol 2,6-di- ---tert-butyl- -p-tolyl methylcarbamate 
terbutryn 2-( ---tert-butylamino)-4-(ethylamino)-6- 
methylthio)- .sub.-s-triazine 
tetrafluron N,N--dimethyl-N'--[3-(1,1,2,2-tetra- 
fluoroethoxy)phenyl]urea 
thiobencarb S--[(4-chlorophenyl)methyl] diethyl- 
carbamothioate 
triallate S--(2,3,3-trichloroallyl)diisopropyl- 
thiocarbamate 
trifluralin .alpha.,.alpha.,.alpha.-trifluoro-2,6-dinitro-N,N-- 
dipropyl- -p-toluidine 
trimeturon 1-( -p-chlorophenyl)-2,3,3-tri- 
methylpseudourea 
2,3,6-TBA 2,3,6-trichlorobenzoic acid and 
agriculturally suitable salts 
and esters thereof 
2,4-D (2,4-dichlorophenoxy)acetic acid 
and agriculturally suitable 
salts and esters thereof 
2,4-DB 4-(2,4-dichlorophenoxy)butyric 
acid and agriculturally suit- 
able salts and esters thereof 
2,4-DEP tris[2-(2,4-dichlorophenoxy)- 
ethyl] phosphite 
methabenzthiazuron 
1,3-dimethyl-3-(2-benzothiazolyl)- 
urea 
chlortoluran 
N'--(3-chloro-4-methylphenyl)-N'N-- 
dimethylurea 
isoproturan N--(4-isopropylphenyl)-N'N'--di- 
dimethylurea 
metoxuran N'--(3-chloro-4-methoxyphenyl)-N,N-- 
dimethylurea 
______________________________________ 
When an added herbicide is water-soluble, the pH of the resulting 
composition may need to be adjusted to lie within the range of 6 to 9. 
The following examples illustrate methods for preparing the complexes of 
sulfonylurea salts of Formula I with ureas of Formula II wherein R.sub.1 
is H or CH.sub.3 and R.sub.12 and R.sub.13 are H.

EXAMPLE 1 
Thirty grams of 
2-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]ben 
zoic acid, methyl ester of 98.9% purity (0.0778 mole) were added to 100 g 
water containing 3.1 g (0.0778 mole) sodium hydroxide with vigorous 
stirring. A clear solution of the sodium salt of the sulfonylurea was 
formed, pH 7.61. To the solution then was added a solution of 18.7 g (0.31 
mole) urea in 50 g water. The initially clear mixture clouded rapidly in 
less than one minute and precipitation of fine crystals occurred. After 30 
minutes, the slurry was filtered and the cake was washed with cold 
methanol and dried. The water-soluble product weighed 34 g and was 
analyzed as a 1:1 molar complex of the sodium salt of the sulfonylurea and 
urea. 
EXAMPLE 2 
One gram of any one of the preformed sodium salts of the following 
sulfonylureas: 
A. 
5-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-1-methyl-1H- 
pyrazole-4-carboxylic acid, ethyl ester 
B. 
N-[[4-ethoxy-6-(methylamino)-1,3,5-triazin-2-yl]aminocarbonyl]-3,4-dihydro 
-3-methyl-1-oxo-1H-2-benzopyran-8-sulfonamide 
C. 
N-[[4-(2,2,2-trifluoroethoxy)-6-methoxy-1,3,5-triazin-2-yl]aminocarbonyl]- 
2-ethoxybenzenesulfonamide 
D. 
N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-(2-chloroethoxy 
)benzenesulfonamide, 
was dissolved in 15 ml of methanol and then the solution was mixed with 10 
ml of a methanolic solution of urea containing two equivalents of urea per 
equivalent of sulfonylurea salt. A precipitate of the 1:1 molar complex 
rapidly formed. 
EXAMPLE 3 
Thirty grams (0.0778 mole) of the sulfonylurea of Example 1 was neutralized 
with 4.36 g (0.0778 mole) potassium hydroxide and the salt was mixed with 
18.7 g (0.31 mole) urea as described in Example 1. Precipitation of a 
course granular solid began several minutes later and was complete in 15 
minutes. The product was isolated and identified as a 1:1 molar complex of 
the potassium salt of the sulfonylurea and urea; yield 26.5 g. 
EXAMPLE 4 
Preformed lithium salt of the sulfonylurea of Example 1 was used in the 
following experiments to show the effect of varying the proportion of 
urea-to-sulfonylurea salt upon the composition of the complex formed: 
A. 21.5 g (0.05 mole) lithium salt of sulfonylurea in 60 g methanol was 
mixed with 3.03 g (0.05 mole) urea. A complex rapidly formed and was 
isolated and dried; 12.6 g. 
B. Experiment A was repeated with 6.06 g (0.10 mole) urea; 13.9 g complex 
was obtained. 
C. Experiment A was repeated with 12.12 g (0.20 mole) urea; 18.9 g complex 
was obtained. 
Analyses showed that all of the products which 
were formed by combining urea and the lithium salt of the sulfonylurea in 
proportions of 1:1 (A.), 2:1 (B.) and 4:1 (C.) had the same 1:1 molar 
composition. 
In the following examples, 1:1 molar complexes of sulfonylurea salts and 
urea were prepared as described in Example 1: 
______________________________________ 
Sulfonylurea 
Ex. (Neutralizing Agent) 
Solvent 
______________________________________ 
5 A Water 
(LiOH) 
6 B Methanol 
(NaOH) 
7 C Methanol 
(NaOH) 
8 D Methanol 
(KOH) 
______________________________________ 
A=2-chloro-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]benzenes 
ulfonamide; 
B=2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonylmethyl]benzoi 
c acid, methyl ester; 
C=3-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]-2 
-thiophenecarboxylic acid, methyl ester; 
D=2-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoic acid, 
methyl ester. 
EXAMPLE 9 
To a dispersed mixture of 11.57 g (0.03 mole) of the sulfonylurea of 
Example 1 and 3.33 g (0.045 mole) of methylurea in 40 g ethyl alcohol was 
added 1.20 g (0.03 mole) of sodium hydroxide in 2 ml water. Upon stirring, 
a clear solution formed and shortly thereafter a fine solid rapidly 
precipitated. The slurry was cooled in ice water for 30 minutes and 
filtered. The cake was washed with ice-cold ethanol and dried to give 
13.85 g of a product identified as a 1:1 molar complex of the lithium salt 
of the sulfonylurea and methylurea. 
The following examples illustrate methods for preparing the complexes of 
sulfonylurea salts of Formula I with ureas of Formula II wherein at least 
one of R.sub.1, R.sub.12 and R.sub.13 is other than H. 
EXAMPLE 10 
Thirteen grams (0.03 mole) of the lithium salt of the sulfonylurea of 
Example 1 was dispersed in 30 g acetone. The solubility of the salt had 
been previously determined as less than 5%. To the stirred suspension was 
added solid n-butylurea in portions. With each addition of n-butylurea, 
part of the sulfonylurea salt dissolved until, after about 4.4 g (0.0375 
mole) had been added, a clear solution was obtained. This gave a solution 
which contained 27.4% of the sulfonylurea salt as a complex of 
n-butylurea. Preparation of a solution containing greater than 50% of the 
sulfonylurea salt was accomplished by evaporation of acetone. 
EXAMPLE 11 Twenty-two and six-tenths grams (0.06 mole) of 
2-chloro-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]benzenesu 
lfonamide of 95% purity and 9.75 g (0.075 mole) of n-pentylurea were 
slurried in 60 g methyl isobutyl ketone. Both solids had low solubility in 
the solvent. With rapid stirring, 2.56 g (0.061 mole) solid lithium 
hydroxide hydrate were added. The solids rapidly dissolved as the salt was 
formed and complexed with the urea compound. The sulfonylurea salt 
concentration in methyl isobutyl ketone was 26.5%. Without n-pentylurea 
present, the concentration of the salt would have been less than 5%. 
In the following examples, complexes of sulfonylurea salts and ureas are 
prepared as described in Example 10. 
______________________________________ 
Sulfonylurea 
(Neutralizing 
Ex. Agent) Urea Solvent 
______________________________________ 
12 A 1,3-Dimethylurea 
Methanol 
(KOH) 
13 B 1,1-Diethylurea Isopropanol 
(NaOH) 
14 C -n-Dodecylurea .gamma.-Butyrolactone 
(LiOH) 
15 D Cyclohexylurea NMethyl- 
(LiOH) pyrrolidine 
16 E (LiOH) 
##STR6## Cyclohexanone 
17 F 2-Butenylurea Ethyl Lactate 
(LiOH) 
______________________________________ 
A=2-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]be 
nzoic acid, methyl ester; 
B=2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonylmethyl]benzoi 
c acid, methyl ester; 
C=3-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]-2 
-thiophenecarboxylic acid, methyl ester; 
D=N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl;]-2-hydroxybenzenesulfonamid 
e, ethanesulfonate; 
E=2-[[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoic acid, 
methyl ester; 
F=2-chloro-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]benzenes 
ulfonamide. 
EXAMPLE 18 
Four grams (0.01 equivalent) of the calcium salt of 
2-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]ben 
zoic acid, methyl ester was dispersed in 30 ml acetone and 1.65 g (0.015 
mole) n-butylurea was added. A clear solution formed but precipitation 
began shortly afterward. The precipitate was filtered, washed with acetone 
and dried. A yield of 4.6 g product was obtained. Analyses showed that the 
product was a complex of two moles n-butylurea per mole of the calcium 
salt of the sulfonylurea. 
EXAMPLE 19 
Four and three-tenths grams (0.01 mole) of the sodium salt of 
2-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]ben 
zoic acid, methyl ester and 1.29 g (0.015 mole) 2-imidazolidone, a cyclic 
urea compound, were dissolved in a mixture of 25 g methanol-5 g water. A 
precipitate formed over a period of several hours, was filtered, washed 
with methanol-water and dried. Total product weighed 4.4 g. Analyses 
showed that the product was a 1:1 molar complex of the urea and 
sulfonylurea salt. 
The following examples describe herbicidal formulations prepared from 
complexes of sulfonylurea salts with ureas: 
EXAMPLE 20 
Solution 
Twelve and one-half grams of a 93% purity lithium salt of the sulfonylurea 
of Example 1 (0.03 mole active material) and 4.4 g (0.0375 g) n-butylurea 
were dissolved in 40 g .gamma.-butyrolactone to give a 20% solution of 
active sulfonylurea. On accelerated aging for 3 weeks at 45.degree. C., 
the relative decomposition of active component was 3.15%. The water 
content was measured as 0.75%. A similar composition with this level of 
water containing no n-butylurea showed 18% relative decomposition. 
This example illustrates the improved hydrolytic stability of a 
sulfonylurea when its salt is complexed with a substituted urea. 
In the following examples, other solutions of sulfonylurea salts complexed 
with n-octylurea are shown to have improved stability. 
______________________________________ 
% Rel. % Rel. 
Sulfonylurea 
Solvent Decomp. 
Decomp. 
Ex. Salt (% H.sub.2 O) 
w Urea w/o Urea 
______________________________________ 
21 A Acetonitrile 2.0 12.0 
(1.25) 
22 B Methyl Isobutyl 
1.5 10.5 
Ketone (0.65) 
______________________________________ 
A=3-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]-2 
-thiophenecarboxylic acid, methyl ester; 
B=2-[[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoic acid, 
methyl ester. 
EXAMPLE 23 
______________________________________ 
Wettable Powder 
______________________________________ 
Complex of Example 1 40.0% 
dioctyl sodium sulfosuccinate 
1.5% 
sodium ligninsulfonate 
3.0% 
low viscosity methyl cellulose 
1.5% 
attapulgite 54.0% 
______________________________________ 
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. 
EXAMPLE 24 
______________________________________ 
Oil Suspension 
______________________________________ 
Complex of Example 5 25% 
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 
suspension may be applied directly, but preferably after being extended 
with oils or emulsified in water. 
EXAMPLE 25 
______________________________________ 
Granules 
______________________________________ 
Wettable powder of Example 23 
15% 
gypsum 69% 
potassium sulfate 16% 
______________________________________ 
The ingredients are blended in a rotating mixer and water is sprayed onto 
the blend to accomplish granulation. When most of the material has reached 
the desired range of 1.0 to 0.42 mm (U.S.S. #18 to 40 sieves), the 
granules are moved, dried, and screened. Oversize material is crushed to 
produce additional material in the desired range. 
EXAMPLE 26 
______________________________________ 
Dust 
______________________________________ 
complex of Example 7 
10% 
attapulgite 10% 
talc 80% 
______________________________________ 
The active ingredient is blended with attapulgite and then passed through a 
hammer mill to produce particles substantially all below 200 microns. The 
ground concentrate is then blended with powdered talc until homogeneous. 
EXAMPLE 27 
______________________________________ 
Aqueous Suspension 
______________________________________ 
complex of Example 9 
21.3% 
sodium ligninsulfonate 
1.11% 
sodium acetate 18.71% 
polysaccharide thickener 
0.05% 
water and impurities 
balance 
______________________________________ 
With stirring, the sodium ligninsulfonate and complex is added to the 
water. To this mixture is added the sodium acetate in portions over a 
period of 30 minutes. The resulting composition is ground in a sand mill 
to produce particles essentially under five microns in size. The 
polysaccharide thickener is added several minutes before completion of the 
milling operation. The suspension is passed through a 50 mesh screen to 
remove milling material. 
Utility 
Test results indicate that the compounds of the present invention are 
highly active preemergent or postemergent herbicides or plant growth 
regulants. Many of them have utility for broad-spectrum pre- and or 
post-emergence weed control in areas where complete control of all 
vegetation is desired, such as around fuel storage tanks, ammunition 
depots, industrial storage areas, parking lots, drive-in theaters, around 
billboards, highway and railroad structures. Some of the compounds have 
utility for selective weed control in crops such as rice, wheat, and 
barley. Alternatively, the subject compounds are useful to modify plant 
growth. 
The rates of application for the compounds of the invention are determined 
by a number of factors, including their use as plant growth modifiers or 
as herbicides, the crop species involved, the types of weeds to be 
controlled, weather and climate, formulations selected, mode of 
application, amount of foliage present, etc. In general terms, the subject 
compounds should be applied at levels of around 0.05 to 10 kg/ha, the 
lower rates being suggested for use on lighter soils and/or those having a 
low organic matter content, for plant growth modification or for 
situations where only short-term persistence is required. 
The compounds of the invention may be used in combination with any other 
commercial herbicide; examples of which are those of the triazine, 
triazole, uracil, urea, amide, diphenylether, carbamate and bipyridylium 
types. The compounds may also be used in combination with mefluidide. 
The herbicidal properties of the subject compounds were discovered in a 
number of greenhouse tests. The test procedures and results follow. 
TEST A 
Seeds of crabgrass (Digitaria sp.), barnyardgrass (Echinochloa crusgalli), 
wild oats (Avena fatua), sicklepod (Cassia obtusifolia), morningglory 
(Ipomoea spp.), cocklebur (Xanthium pensylvanicum), sorghum, corn, 
soybean, sugar beet, cotton, rice, wheat and purple nutsedge (Cyperus 
rotundus) tubers were planted and treated pre-emergence with the test 
chemicals dissolved in a non-phytotoxic solvent. At the same time, these 
crop and weed species were treated with a soil/foliage application. At the 
time of treatment, the plants ranged in height from 2 to 18 cm. Treated 
plants and controls were maintained in a greenhouse for sixteen days, 
after which all species were compared to controls and visually rated for 
response to treatment. The ratings, summarized in Table A, are based on a 
numerical scale extending from 0=no injury, to 10=complete kill. The 
accompanying descriptive symbols have the following meanings: 
C=chlorosis/necrosis; 
B=burn; 
D=defoliation; 
E=emergence inhibition; 
G=growth retardation; 
H=formative effect; 
U=unusual pigmentation; 
X=axillary stimulation; 
S=albinism; and 
6Y=abscised buds or flowers. 
##STR7## 
TABLE A 
__________________________________________________________________________ 
Complex 1 
Complex 2 
Complex 3 
Complex 4 
Complex 5 
Complex 6 
Complex 7 
Rate kg/ha .05 .05 .05 .05 .05 .05 .05 
__________________________________________________________________________ 
POSTEMERGENCE 
Morningglory 
9C 10C 10C 10C 10C 10C 10C 
Cocklebur 10C 10C 10C 8H 10C 10C 9C 
Sicklepod 2C,5G 5C,9G 9C 4C,9G 10C 10C 9C 
Nutsedge 5G 0 9C 5C,9G 6C,9G 4C,9G 5C,8G 
Crabgrass 2C,8G 2H 4C,8G 5G 6C,9G 9C 6C,9G 
Barnyardgrass 
3C,9H 1H 9C 3H 9C 5C,9G 6C,9G 
Wild Oats 2C 0 3C,9G 0 9C 4C,8G 2C,8G 
Wheat 2G 0 3G 0 9C 4G 4G 
Corn 8H 0 2C,9G 5H 9C 4U,9G 3U,9G 
Soybean 4H 2C,5H 9C 4C,9G 9C 9C 9C 
Rice 5C,9G 2G 6C,9G 2G 9C 9C 9C 
Sorghum 2U,9G 2C,4G 9C 6G 9C 5C,9G 5C,9G 
Sugar beet 9C 9C 9C 2C,7G 9C 9C 9C 
Cotton 9C 9C 9C 9C 9C 10C 10C 
PREEMERGENCE 
Morningglory 
9C 9G 9G 9C 9G 9G 9G 
Cocklebur 8H 9H 8H 9H 9H 9H 9H 
Sicklepod 8G 5C,9G 9G 9G 9G 9G 5C,9G 
Nutsedge 0 0 10E 7E 10E 8G 8G 
Crabgrass 3G 2G 3C,9G 5G 9C 5C,9G 2C,8G 
Barnyardgrass 
3C,7H 0 5C,9H 5C,8G 5C,9H 4C,8H 3C,9H 
Wild Oats 0 0 3C,8G 3G 9C 4C,8G 2C,8G 
Wheat 2G 0 2G 3G 10H 6G 5G 
Corn 8G 2C,5G 3C,9G 8G 5C,9H 3U,9H 2U,9H 
Soybean 5G 2C,6G 9H 3C,7H 9H 9H 9H 
Rice 3C,8G 0 5C,9H 3G 10E 10E 10E 
Sorghum 3C,9G 5G 5C,9H 3C,8H 5C,9H 5C,9H 5C,9H 
Sugar beet 5C,9G 5C,9G 9C 9G 6C,9G 9C 9C 
Cotton 9G 9G 10C 9G 2C,9G 9C 9C 
__________________________________________________________________________ 
Complex 8 
Complex 9 
Complex 10 
Complex 11 
Complex 12 
Complex 13 
Rate kg/ha .05 .05 .05 .05 .05 .05 
__________________________________________________________________________ 
POSTEMERGENCE 
Morningglory 
10C 10C 9C 9C 9C 9C 
Cocklebur 10C 10C 9C 10C 9C 9C 
Sicklepod 9C 9C 9C 9C 9C 9C 
Nutsedge 2C,8G 3C,5G 4G 5G 4G 2C,8G 
Crabgrass 5C,9G 4C,8G 2C,7G 4C,8G 3C,8G 4C,8G 
Barnyardgrass 
5C,9H 9C 9C 9C 9C 9C 
Wild Oats 2C,8G 3G 3G 2G 1C 2C,8G 
Wheat 3G 4G 3G 2G 2G 4G 
Corn 10C 9G 10C 2U,9G 4C,9G 2U,9G 
Soybean 9C 9C 9C 9C 9C 9C 
Rice 9C 5C,9G 6C,9G 5C,9G 5C,9G 9C 
Sorghum 5C,9G 3C,9H 2C,9H 4C,9H 3C,9H 3C,9G 
Sugar beet 9C 9C 9C 9C 9C 9C 
Cotton 10C 9C 9C 9C 9C 9C 
PREEMERGENCE 
Morningglory 
9C 9G 9C 9G 9C 9G 
Coclebur 9H 9H 9H 9H 8H 9H 
Sicklepod 9G 2C,9G 9G 3C,9G 9G 9G 
Nutsedge 2C,8G 0 3G 3G 3G 6G 
Crabgrass 3C,8G 3C,7G 6G 8G 8G 2C,8G 
Barnyardgrass 
3C,9H 4C,9H 4C,9H 3C,9H 3C,9H 3C,9H 
Wild Oats 3C,7G 3G 2G 3G 2G 2C,8G 
Wheat 5G 2G 2G 3G 2G 1C,3G 
Corn 3U,9H 3C,9H 9G 9G 9G 3C,9H 
Soybean 9H 9H 9H 9H 9H 9H 
Rice 10E 3C,9H 5C,9H 5C,9H 5C,9H 10E 
Sorghum 6C,9H 5C,9H 4C,9H 5C,9H 4C,9H 6C,9H 
Sugar beet 9C 9C 9C 9C 9C 9C 
Cotton 9C 9G 9G 9C 9G 9C 
__________________________________________________________________________