This invention relates to compositions comprising 1-aryl-4,5-dihydro-1,2,4-triazol-5(1H)-ones (triazolinones) in combination with the herbicide (2,4-dichlorophenoxy)acetic acid (2,4-D), or like substituted phenoxyalkanoic acids, or esters, or alkali metal or ammonium salts thereof; or with certain herbicidal sulfonylureas, or mixtures of these classes of compounds, to provide herbicidal compositions which are highly effective against a broad array of crop weeds, particularly broadleaf weeds, in crops such as wheat.

BACKGROUND OF THE INVENTION 
This invention relates to compositions comprising 
1-aryl-4,5-dihydro-1,2,4-triazol-5(1H)-ones (hereinafter "triazolinones") 
in combination with other herbicidal compounds, which compositions are 
useful as herbicides, especially against broadleaf weeds such as mustards, 
kochia, and the like. More particularly, it relates to these triazolinones 
in combination with the herbicide (2,4-dichlorophenoxy)acetic acid 
("2,4-D"), or like substituted phenoxyalkanoic acids, or herbicidally 
effective commercially available esters, or alkali metal or ammonium salts 
thereof; or with certain herbicidal sulfonylureas, as defined below 
(hereinafter "sulfonylureas"), or mixtures of these classes of compounds, 
to provide post-emergence herbicidal compositions which are highly 
effective against a broad array of weeds which infest crops. 
The triazolinones employed in this invention, their preparation, and their 
use in combination with other herbicides including known herbicidal 
acetamides, benzothiodiazinones, triazines, dinitroanilines, and aryl 
ureas, is known from PCT International Application WO 90/02120, published 
Mar. 9, 1990, discussed in further detail below, and whose U.S. 
counterpart is a parent of the present continuation-in-part application. 
The combination of these triazolinones with 2,4-D, or other substituted 
phenoxy alkanoic acids, or with sulfonylureas is, however, not taught or 
suggested by this PCT publication. 
SUMMARY OF THE INVENTION 
In accordance with the present invention it has now been found that 
compositions comprising triazolinones, as defined herein, in combination 
with 2,4-D, or like herbicidally effective substituted phenoxy alkanoic 
acids, or with sulfonylureas, or mixtures of the latter compounds, in 
agriculturally acceptable carriers, are highly effective post-emergence 
herbicides in the control of a wide number of weeds which infest crops, 
particularly members of the mustard family, including shepherdspurse, 
bitter cress, blue mustard, tansymustard, flixweed, and field pennycress. 
These compositions are particularly advantageous in that they provide for 
rapid kill of the majority of plant tissues, protection against the 
regrowth of the weeds and herbicidal control over a broad spectrum of 
broadleaf weeds, thus providing overall better herbicidal control. These 
compositions are generally faster acting or more effective than any one 
component alone. In the case of 2,4-D, the combination allows the use of 
lower rate of 2,4-D, compared with a higher application rate of 2,4-D 
alone.

DETAILED DESCRIPTION OF THE INVENTION 
As described in PCT application WO 90/02120 (supra), which is incorporated 
herein by reference, the triazolinones employed as components of the 
claimed compositions comprise herbicidal 
1-aryl-4,5-dihydro-2,4-triazol-5(1H)-ones of the formula 
##STR1## 
in which 
R is halogen or lower alkyl; 
R.sup.1 is haloalkyl; 
X is hydrogen, halogen, alkyl, haloalkyl, alkoxy or nitro; 
Y is hydrogen, halogen, alkyl, alkoxy, haloalkyl, halo lower alkylsulfinyl, 
or halo lower alkoxy; 
Q is --CH(R.sup.2)C(R.sup.3)(R.sup.4)Q' or --CH.dbd.C(R.sup.4)Q'; 
R.sup.2 is H or halogen; 
R.sup.3 is halogen; 
R.sup.4 is H or lower alkyl; 
Q' is CO.sub.2 H, CO.sub.2 R.sup.5, CON(R.sup.6)(R.sup.7), CN, CHO, or 
C(O)R.sup.5 ; 
R.sup.5 is alkyl, alkoxycarbonylalkyl, cycloalkyl, benzyl, chlorobenzyl, 
alkylbenzyl, or haloalkylbenzyl; and each of R.sup.6 and R.sup.7 is 
independently H, or a radical which is an alkyl, cycloalkyl, alkenyl, 
alkynyl, alkoxy, phenyl, benzyl, or SO.sub.2 R.sup.6 (in which R.sup.6 is 
other than H) or is one of said radicals substituted by halogen, alkyl, or 
cyano; 
or a base-addition salt of the compound in which Q' is CO.sub.2 H; or 
resolved isomers thereof; with the proviso that any alkyl, alkenyl, or 
alkynyl moiety have less than 6 carbon atoms and that any cycloalkyl 
moiety have 3 to 7 carbon atoms. 
Preferred amongst these compounds where R.sup.2, R.sup.3 and R.sup.4 have 
the meanings set forth above, and R, R', X and Y may be as follows: each 
of R and R.sup.1 may, independently, be lower alkyl (preferably methyl) or 
halo lower alkyl such as fluoro lower alkyl (e.g. CF.sub.2 CHF.sub.2 or 
CHF.sub.2). R may also be a halogen atom such as chlorine. Preferably R is 
methyl and R.sup.1 is CHF.sub.2. The substituent X may be hydrogen; 
halogen such as chlorine, bromine, or fluorine (preferably fluorine); 
alkyl such as lower alkyl (e.g. methyl); haloalkyl such as halo lower 
alkyl (e.g. CF.sub.3, CH.sub.2 F or CHF.sub.2); alkoxy such as lower 
alkoxy (e.g. methoxy); or nitro; and Y may be hydrogen; halogen such as 
chlorine, bromine, or fluorine (preferably bromine or chlorine); alkyl 
such as lower alkyl (e.g. methyl); alkoxy such as lower alkoxy (e.g. 
methoxy); haloalkyl such as halo lower alkyl (e.g. fluoroalkyl); halo 
lower alkylsulfinyl (e.g. --SOCF.sub.3); or halo lower alkoxy (e.g. 
--OCHF.sub.2). Particularly preferred X, Y substituents are: 2-F, 4-Cl; 
2-F, 4-Br; 2,4-diCl; 2-Br, 4-Cl; and 2-F, 4-CF.sub.3. 
It is preferable that any alkyl, alkenyl, alkynyl or alkylene moiety (such 
as the hydrocarbon moiety of an alkoxy or haloalkoxy group) have less than 
6 carbon atoms, e.g. 1 to 3 or 4 carbon atoms, and that any cycloalkyl 
moiety have 3 to 7 ring carbon atoms, preferably 3-6 carbon atoms. 
Any acidic compounds, including sulfonamides in which NR.sup.6 R.sup.7 is 
NHSO.sub.2 R.sup.6, may be converted to the corresponding base addition 
salt by known methods. 
Of particular interest in this invention are such compounds as ethyl 
2-chloro-3-[2-chloro-4-fluoro-5-(4-difluoromethyl-4,5-dihydro-3-methyl-5-o 
xo-1H-1,2,4-triazol-1-yl)phenyl]propionate, (hereinafter "Compound P") 
having the formula 
##STR2## 
and, e.g., the 4-chloro analog of this 4-fluoro compound. 
Certain of the 1-aryl-4,5-dihydro-1,2,4-triazol-5(1H)-ones of the present 
invention contain an asymmetric carbon atom; the invention thus includes 
individual stereoisomers as well as racemic and non-racemic mixtures of 
enantiomers of the instant compounds. For example, ethyl 
2-chloro-3-[2-chloro-4-fluoro-5-(4-difluoromethyl-4,5-dihydro-3-methyl-5-o 
xo-1H-1,2,4-triazol-1-yl)phenyl]propionate ("Compound P") is composed of a 
2S and a 2R isomer. The 2S and 2R isomers of Compound P were separated by 
High Pressure Liquid Chromatography (HPLC), a method known to one skilled 
in the art, using a DIACEL CHIRALCEL OD column (distributed by Diacel 
Chemical Industries Ltd., Exton, Pa.), 4.6 mm ID.times.250 mm, packed with 
silica gel of 10 .mu.m in particle size. Elution was accomplished with 
1.5% ethanol in hexane at a flow rate of 1 mL/minute. 
The triazolinone compounds may be prepared by methods described in PCT 
Application WO/02120 or in the following illustrative example, or by 
methods analogous and similar thereto which are within the skill of the 
art. 
For instance, in Step A of the example below an amino compound of the 
formula (II) 
##STR3## 
(such as the compound shown in Example 1 of International patent 
publication WO 87/03782, published Jul. 2, 1987) is reacted (according to 
the Meerwein arylation reaction described below or a modification thereof) 
with an olefinic compound having the formula CHR.sup.2 .dbd.CR.sup.4 Q' to 
form a compound of Formula I above in which Q is 
--CH(R.sup.2)C(R.sup.3)(R.sup.4)Q' and in which R.sup.3 is halogen. In 
this type of reaction the amino compound is converted to a diazonium salt 
which then reacts with the olefinic compound through a radical mechanism. 
The Meerwein arylation reaction is discussed in an article by Doyle et al 
in J. Org. Chem., 42, 2431 (1977) which also describes a modification of 
that reaction in which an alkyl nitrite and a copper (II) halide are 
employed. (Step A of the example below employs the Doyle et al 
modification.) Instead, one may employ the unmodified reaction, in which 
the arenediazonium halide is initially prepared in an aqueous halogen acid 
solution and then mixed with the olefinic compound in the presence of an 
appropriate solvent (e.g. acetone) followed by the copper salt, such as 
copper (I) chloride. 
Examples of olefinic compounds having the formula CHR.sup.2 .dbd.CR.sup.4 
Q' are methyl acrylate, ethyl acrylate, methyl methacrylate, methyl 
crotonate, methyl 3-chloroacrylate, methacrolein, vinyl methyl ketone, 
methacrylonitrile and acrylamide. 
The product made by the reactions described above, i.e. a compound of 
Formula I in which Q is --CH(R.sup.2)C(R.sup.3)(R.sup.4)Q' and in which 
R.sup.3 is halogen, may be treated to form other compounds of this 
invention. Dehydrohalogenation of that compound (e.g. with sodium hydride 
or other suitable base), when R.sup.2 is H, yields a compound in which Q 
is --CH.dbd.C(R.sup.4)Q' (as in Step B of the example). That compound may 
be hydrogenated or halogenated to form a compound in which Q is 
--CH(R.sup.2)C(R.sup.3)(R.sup.4)Q' and R.sup.3 is H (from hydrogenation, 
as in Step C) or R.sup.2 and R.sup.3 are halogen. When Q' is --CO.sub.2 H, 
the acidic compound of formula I may be converted to the corresponding 
amide, as by first treating with a reagent such as thionyl chloride to 
form the acid halide (wherein Q' is, for example, --COCl) and then 
reacting with ammonia or an amine. Alternative methods of amide formation, 
involving carbodiimide-mediated coupling, are known, as for example where 
the amide is formed from the carboxylic acid (of e.g. formula I) and the 
amine, in the presence of dicyclohexylcarbodiimide, I-hydroxybenzotriazole 
and a base such as a tertiary amine, e.g. N,N-diisopropylethylamine or 
triethylamine, in a solvent such as tetrahydrofuran. 
Instead of starting with an amino compound one may start with an otherwise 
identical compound having a CHO group in place of the NH2 group and react 
it with a Wittig reagent (which may be a standard type of Wittig reagent 
or a modified type such as a Wadsworth-Emmons reagent). Thus, the reagent 
may be an alkylidene phosphorane whose alkylidene group has the formula 
.dbd.C(R.sup.4)Q' such as (C.sub.6 H.sub.5).sub.3 P.dbd.CHCO.sub.2 R.sub.5 
or it may be a phosphonate ylide comprising a phosphonate diester in which 
the group directly attached to the P atom has the formula --CH(R.sup.4)Q 
such as (C.sub.2 H.sub.5 O).sub.2 P(O)CH.sub.2 CO.sub.2 R.sup.5, used 
together with, say, NaH in known manner. R.sup.5 is preferably lower alkyl 
such as methyl or ethyl. The product thereof may be hydrogenated to 
produce a compound of Formula I in which R.sup.2 and R.sup.3 are each 
hydrogen, or it may be halogenated (e.g. with chlorine) to form a compound 
of Formula I in which R.sup.2 and R.sup.3 are each halogen. The latter 
compound may in turn be dehydrohalogenated to form a compound in which 
R.sup.4 is halogen and then hydrogenated to form a compound of Formula I 
in which R.sup.4 is halogen and R.sup.3 and R.sup.2 are H. 
Instead of starting with a compound containing the triazolinone ring and 
adding thereto the Q substituent, one may start with a compound of the 
formula 
##STR4## 
and then form the triazolinone ring. Compounds of Formula III are shown, 
for instance, in published European patent applications 300387 and 300398. 
The NH.sub.2 group may be converted to a triazolinone ring in known 
manner. For instance it may be converted to an NHNH.sub.2 (i.e. hydrazine) 
group in the conventional fashion, by diazotization followed by reduction 
with sodium sulfite, and the hydrazine group may be converted to a 
triazolinone ring. 
When X and Y are substituents other than H, such substituents may be 
introduced at various stages of the process, e.g., prior to the formation 
of a compound containing the Q substituent. One or both of these 
substituents may be introduced after the introduction of the Q 
substituent; for instance, a chlorine substituent on the benzene ring may 
be introduced during one of the halogenation steps which modify the Q 
substituent, as described above. 
The preparation of the triazolinone components is illustrated by the 
following example. In this application, all parts are by weight and all 
temperatures are in .degree.C. unless otherwise indicated. 
EXAMPLE 
Methyl 3-[2,4-Dichloro-5-(4-Difluoromethyl-4,5-Dihydro 
3-Methyl-5-Oxo-1H-1,2,4-Triazol-1-Yl)Phenyl]Propionate 
Step A: Methyl 
2-Chloro-3-[2,4-dichloro-5-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H 
-1,2,4-triazol-1-yl)phenyl]propionate 
To a cold (0.degree. C.), stirred mixture of 28.7 g (0.333 mole) of methyl 
acrylate, 2.51 g (0.0244 mole) of tert-butyl nitrite, and 2.6 g (0.019 
mole) of copper (II) chloride in 50 mL of acetonitrile was added dropwise 
a solution of 5.0 g (0.016 mole) of 
1-(5-amino-2,4-dichlorophenyl)-4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4 
-triazol-5(1H)-one in 15 mL of acetonitrile. After complete addition the 
reaction mixture was allowed to warm to room temperature and was stirred 
for approximately 18 hours. The reaction mixture was diluted with 15 mL of 
2N hydrochloric acid solution. The mixture was extracted with four 
portions of diethyl ether. The combined extracts were dried over anhydrous 
magnesium sulfate, filtered, and the filtrate evaporated under reduced 
pressure to give an oil. The oil was purified by column chromatography on 
silica gel, eluting with n-heptane:ethyl acetate (4:1) to give 5.0 g of 
methyl 2-chloro-3-[2,4-dichloro-5 
-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-I-yl)phenyl 
]propionate as an oil. 
Step B Methyl 
3-[2,4-dichloro-5-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-tr 
iazol-1-yl)phenyl]-2-propenoate 
To a stirred, cold (0.degree. C.) solution of 4.16 g (0.0100 mole) of 
methyl 2-chloro-3-[2,4-dichloro-5-(4-difluoromethyl-4,5-dihydro-3-methyl-5 
-oxo-1H-l,2,4 -triazol-1-yl)phenyl]propionate in 15 mL of 
N,N-dimethylformamide was added portionwise 0.29 g (0.012 mole) of sodium 
hydride. After complete addition the reaction mixture was allowed to warm 
to room temperature and was stirred for 30 minutes. The reaction mixture 
was heated at 60.degree. C. for six hours, then was stirred at room 
temperature for approximately 18 hours. The reaction mixture was poured 
into ice water, and the resultant aqueous mixture was extracted with four 
portions of diethyl ether. The extracts were combined and washed 
successively with water and an aqueous, saturated sodium chloride 
solution. The washed organic phase was dried over anhydrous magnesium 
sulfate and was filtered. The filtrate was evaporated under reduced 
pressure to give a white foam. The foam was purified by column 
chromatography on silica gel, eluting with n-heptane:ethyl acetate (4:1), 
to give 1.63 g of methyl 
3-[2,4-dichloro-5-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-l,2,4-tr 
iazol-1-yl)phenyl]-2-propenoate as a solid, m.p. 141.degree.-151.degree. C. 
Step C: Methyl 
3-[2,4-dichloro-5-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-tr 
iazol-1-yl)phenyl]propionate 
Hydrogenation of 0.59 g (0.0016 mole) of methyl 
3-[2,4-dichloro-5-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-tr 
iazol-1-yl)phenyl]-2-propenoate over approximately 0.2 g (0.0009 mole) of 
platinum (IV) oxide in approximately 15 mL of ethyl acetate gave 0.59 g of 
methyl 
3-[2,4-dichloro-5-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-tr 
iazol-I-yl)phenyl]propionate as a clear oil, which crystallized upon 
standing. The crystals were triturated with petroleum ether and recovered 
by filtration, m.p. 70.degree.-73.degree. C. 
The preferred triazolinone component of the compositions of this invention 
as stated above, namely ethyl 
2-chloro-3-[2-chloro-4-fluoro-5-(4-difluoromethyl-4,5-dihydro-3-methyl-5-o 
xo-(1H)-1,2,4-triazol-1yl)phenyl]propionate, (i.e., "Compound P") may 
readily be prepared in accordance with the procedures of the foregoing 
example, but substituting 
1-(5-amino-4-chloro2-fluorophenyl)-4-difluoromethyl-4,5-dihydro-3-methyl1, 
2,4-triazol-5-(1H)-one and ethyl acrylate for 1-(5 
-amino-2,4-dichlorophenyl)-4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-tri 
azol-5(1H)-one and methyl acrylate in Step A. 
As stated above, the second component of the herbicidal triazolinone 
composition of this invention is preferably a chlorinated phenoxy lower 
alkanoic acid compound, and most particularly (2,4-dichlorophenoxy)acetic 
acid, commonly known as 2,4-D, and the esters, or alkali metal or ammonium 
salts thereof, all of which are available commercially from several 
sources, e.g. Chevron (Weed-B-Gone.TM.), Pennwalt (Pennamine.TM.D), and 
the like. However, there may also be employed related, commercially 
available herbicidal chlorinated lower alkylphenoxy alkanoic acid 
compounds as (4-chloro-2-methylphenoxy)acetic acid, commonly known as 
MCPA; 4-(4-chloro-2-methylphenoxy)butanoic acid, commonly known as MCPB; 
2-(4-chloro-2-methylphenoxy)propionic acid, commonly known as MCPP or 
mecoprop, and its herbicidally active isomers; and the esters, salts, and 
amines of each of the above, such as MCPA amine, or MCPA ester, (Riverdale 
Chemical Co., Glenwood, Illinois), MCPP-p (BASF), or the like. 
By the term esters, as used above to define 2,4-D and related phenoxy 
alkanoic acid derivatives, is meant principally those prepared from 
C.sub.1 -C.sub.10 aliphatic alcohols. Of these, the isooctyl ester of 
2,4-D, which is commercially available as Weedtime II ("2,4-D ester") from 
Applied Biochemists Inc. (Mequon, Wis.), is preferred. The corresponding 
salts are generally alkali metal or ammonium salts, commercially available 
as, e.g., the potassium salt, or as the ammonium salt, (commonly referred 
to as "amines" of 2,4-D compounds), e.g., the dimethylamine salt. (See, 
e.g., Farm Chemicals Handbook, Meister Publishing Co. (1990), pp. 
C-87-88.) The compound MCPP-p, set forth above, is the resolved (+) isomer 
of the above-defined commercially available mecoprop. (See Farm Chemicals 
Handbook, supra, pp. C-183-185.). 
Alternatively, in a further embodiment of this invention, the triazolinones 
may instead be combined with herbicidal sulfonylureas of the formula 
##STR5## 
Included amongst the sulfonylureas which, in accordance with this 
invention, may be used in combination with the herbicidal triazolinones 
are known commercially available herbicides such as: 
methyl 
2-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]amino]sulfonyl 
]benzoate (metsulfuronmethyl), (ALLY.TM. - E. I. DuPont, Wilmington, Del.); 
2-chloro-N-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]benzenes 
ulfonamide (chlorsulfuron), (GLEAN.TM. - E. I. DuPont, Wilmington, Del.); 
methyl 
2-[[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]-carbony]amino]sulfonyl]methyl]b 
enzoate (bensulfuronmethyl), (LONDAX.TM. - E. I. DuPont, Wilmington, Del.); 
methyl 2-[[[[N-(4-methoxy-6-methyl-1 
,3,5-triazin-2-yl)methylamino]carbonyl]amino]sulfonyl]benzoate 
(tribenuron-methyl), (EXPRESS.TM.- E. I. DuPont, Wilmington, Del.); 
methyl 
3-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]amino]sulfonyl 
]-2-thiophenecarboxylate (thifensulfuron-methyl), (HARMONY.TM. - E. I. 
DuPont, Wilmington, Del.); 
ethyl 5-[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]- 
C&gt;carbonyl]amino]sulfonyl]-1-methyl-1H-pyrazole-4carboxylate 
(pyrazosulfuron-ethyl), (SIRIUS - Nissan Chemical Industries, Ltd., Tokyo, 
Japan); 
2-[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]-carbonyl]amino]sulfonyl]-N,N-dime 
thyl-3-pyridinecarboxamide (nicosulfuron), (ACCENT.TM. - E. I. DuPont, 
Wilmington, Del.); 
methyl 
5-[[[[(4,6-dimethyl-2-pyrimidinyl)amino]-carbonyl]amino]sulfonyl]-1-(2-pyr 
idinyl)-1H-pyrazole-4carboxylate (NC-330, - available from Nissan Chemical 
Industries, Ltd., Tokyo, Japan); 
3-ethylsulfonyl-N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]-carbonyl]-2-pyridin 
ylsulfonamide (DPXE 9636, - available from E. I. DuPont Co., Wilmington, 
Del.); and 
N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-2-chloroimidazo-[1,2-a]pyr 
idinecarboxamide (TH-913, - available from Takeda Chemical Industries, 
Ltd., Tokyo, Japan). 
The active herbicidal compositions of this invention may also be used in 
combination with other herbicides, e.g. they may be mixed with, say, an 
equal or larger amount of known herbicides such as 
N-(1-ethylpropyl)-2,4-dinitro-3,4-xylidene (pendamethalin); 
(RS)-2-[2,4-dichlorophenoxy)phenoxy]propionic acid (diclofop); 
2,4-difluoro-2-(.alpha.,.alpha.,.alpha.-trifluoro-m-tolyloxy)nicotinalanil 
ide (diflufenican); 
(.+-.)-2-[4-(6-chloro-1,3-benzoxazol-2yloxy)phenoxy]propionic acid 
(fenoxaprop); 3-p-cumenyl1,1-dimethylurea (isoproturon); 
4-hydroxy-3,5diiodobenzonitrile (ioxynil); or 3,6-dichloro-o-anisic acid 
(dicamba). 
The weight ratio of triazolinone to 2,4-D, or to the sulfonylurea in order 
to obtain the desired herbicidal effect is not critical, and may be varied 
widely. Thus, for example, the ratio of triazolinone to 2,4-D may range 
from about 1:125 to 1:2, more preferably 1:17 to 1:4, while the ratio of 
triazolinone to sulfonylurea may range from about 8:1 to 30:1, more 
preferably 1:1 to 16:1. It will be understood that these ranges may be 
adjusted by those skilled in the art depending upon the crops involved, 
field conditions and the like. 
FORMULATIONS 
For herbicidal application, the active compositions are formulated by 
admixture in herbicidally effective amounts with adjuvants and carriers 
normally employed in the art for facilitating the dispersion of active 
ingredients for the particular utility desired, recognizing the fact that 
the formulation and mode of application of a toxicant may affect the 
activity of the material in a given application. Thus, for agricultural 
use the present herbicidal compositions may be formulated as granules of 
relatively large particle size, as water-soluble or water-dispersible 
granules, as powdery dusts, as wettable powders, as emulsifiable 
concentrates, as solutions, or as any of several other known types of 
formulations, depending on the desired mode of application. 
These herbicidal compositions may be applied either as water-diluted 
sprays, or dusts, or granules to the areas in which suppression of 
vegetation is desired. These formulations may contain as little as 0.1%, 
0.2% or 0.5% to as much as 95% or more by weight of active ingredients. 
Dusts are free flowing admixtures of the active ingredient with finely 
divided solids such as talc, natural clays, kieselguhr, flours such as 
walnut shell and cottonseed flours, and other organic and inorganic solids 
which act as dispersants and carriers for the toxicant; these finely 
divided solids have an average particle size of less than about 50 
microns. A typical dust formulation useful herein is one containing 1.0 
part or less of the herbicidal composition and 99.0 parts of talc. 
Wettable powders, also useful formulations for both pre- and postemergence 
herbicides, are in the form of finely divided particles which disperse 
readily in water or other dispersant. The wettable powder is ultimately 
applied to the soil either as a dry dust or as an emulsion in water or 
other liquid. Typical carriers for wettable powders include Fuller's 
earth, kaolin clays, silicas, and other highly absorbent, readily wet 
inorganic diluents. Wettable powders normally are prepared to contain 
about 5-80% of active ingredient, depending on the absorbency of the 
carrier, and usually also contain a small amount of a wetting, dispersing 
or emulsifying agent to facilitate dispersion. For example, a useful 
wettable powder formulation contains 80.8 parts of the herbicidal 
compound, 17.9 parts of Palmetto clay, and 1.0 part of sodium 
lignosulfonate and 0.3 part of sulfonated aliphatic polyester as wetting 
agents. Other wettable powder formulations are: 
______________________________________ 
Component: % by Wt. 
______________________________________ 
Active ingredients 40.00 
Sodium lignosulfonate 20.00 
Attapulgite clay 40.00 
Total 100.00 
Active ingredients 90.00 
Dioctyl sodium sulfosuccinate 
0.10 
Synthetic fine silica 9.90 
Total 100.00 
Active ingredients 20.00 
Sodium alkylnaphthalenesulfonate 
4.00 
Sodium lignosulfonate 4.00 
Low viscosity methyl cellulose 
3.00 
Attapulgite clay 69.00 
Total 100.00 
Active ingredients 25.00 
Base: 75.00 
96% hydrated aluminum magnesium silicate 
2% powdered sodium lignosulfonate 
2% powdered anionic sodium alkyl- 
naphthalenesulfonate 
Total 100.00 
______________________________________ 
Frequently, additional wetting agent and/or oil will be added to the 
tank-mix for postemergence application to facilitate dispersion on the 
foliage and absorption by the plant. 
Other useful formulations for herbicidal applications are emulsifiable 
concentrates (ECs) which are homogeneous liquid or paste compositions 
dispersible in water or other dispersant, and may consist entirely of the 
herbicidal compound and a liquid or solid emulsifying agent, or may also 
contain a liquid carrier, such as xylene, heavy aromatic naphthas, 
isophorone, or other non-volatile organic solvent. For herbicidal 
application these concentrates are dispersed in water or other liquid 
carrier, and normally applied as a spray to the area to be treated. The 
percentage by weight of the essential active ingredients may vary 
according to the manner in which the composition is to be applied, but in 
general comprise 0.5 to 95% of active ingredient by weight of the 
herbicidal composition. 
The following are specific examples of emulsifiable concentrate 
formulations: 
______________________________________ 
Component: % by Wt. 
______________________________________ 
Active ingredients 53.01 
Blend of alkylnaphthalenesulfonate 
6.00 
and polyoxyethylene ethers 
Epoxidized soybean oil 
1.00 
Xylene 39.99 
Total 100.00 
Active ingredients 10.00 
Blend of alkylnaphthalenesulfonate 
4.00 
and polyoxyethylene ethers 
Xylene 86.00 
Total 100.00 
______________________________________ 
Flowable formulations are similar to ECs except that the active ingredient 
is suspended in a liquid carrier, generally water. Flowables, like ECs, 
may include a small amount of a surfactant, and contain active ingredient 
in the range of 0.5 to 95%, frequently from 10 to 50%, by weight of the 
composition. For application, flowables may be diluted in water or other 
liquid vehicle, and are normally applied as a spray to the area to be 
treated. 
The following are specific examples of flowable formulations: 
______________________________________ 
Component: % by Wt. 
______________________________________ 
Active ingredients 46.00 
Colloidal magnesium aluminum silicate 
0.40 
Sodium alkylnaphthalenesulfonate 
2.00 
Paraformaldehyde 0.10 
Water 40.70 
Propylene glycol 7.50 
Acetylenic alcohols 2.50 
Xanthan gum 0.80 
Total 100.00 
Active ingredients 45.00 
Water 48.50 
Purified smectite clay 2.00 
Xanthan gum 0.50 
Sodium alkylnaphthalenesulfonate 
1.00 
Acetylenic alcohols 3.00 
Total 100.00 
______________________________________ 
Typical wetting, dispersing or emulsifying agents used in agricultural 
formulations include, but are not limited to, the alkyl and alkylaryl 
sulfonates and sulfates and their sodium salts; alkylaryl polyether 
alcohols; sulfated higher alcohols; polyethylene oxides; sulfonated animal 
and vegetable oils; sulfonated petroleum oils; fatty acid esters of 
polyhydric alcohols and the ethylene oxide addition products of such 
esters; and the addition product of long-chain mercaptans and ethylene 
oxide. Many other types of useful surfaceactive agents are available in 
commerce. The surfaceactive agent, when used, normally comprises from 1 to 
15% by weight of the composition. 
Other useful formulations include simple solutions or suspensions of the 
active ingredient in a relatively non-volatile solvent such as water, corn 
oil, kerosene, propylene glycol, or other suitable solvents. The 
following illustrate specific suspensions: 
______________________________________ 
% by Wt. 
______________________________________ 
Oil Suspension: 
Active ingredients 25.00 
Polyoxyethylene sorbitol hexaoleate 
5.00 
Highly aliphatic hydrocarbon oil 
70.00 
Total 100.00 
Aqueous Suspension: 
Active ingredients 40.00 
Polyacrylic acid thickener 
0.30 
Dodecylphenol polyethylene glycol ether 
0.50 
Disodium phosphate 1.00 
Monosodium phosphate 0.50 
Polyvinyl alcohol 1.00 
Water 56.70 
Total 100.00 
______________________________________ 
Other useful formulations for herbicidal applications include simple 
solutions of the active ingredient in a solvent in which it is completely 
soluble at the desired concentration, such as acetone, alkylated 
naphthalenes, xylene, or other organic solvents. Granular formulations, 
wherein the toxicant is carried on relatively coarse particles, are of 
particular utility for aerial distribution or for penetration of cover 
crop canopy. Pressurized sprays, typically aerosols wherein the active 
ingredient is dispersed in finely divided form as a result of vaporization 
of a low boiling dispersant solvent carrier, such as the Freon fluorinated 
hydrocarbons, may also be used. Water-soluble or water-dispersible 
granules are also useful formulations for herbicidal application of the 
present compounds. Such granular formulations are free-flowing, non-dusty, 
and readily water-soluble or water-miscible. The soluble or dispersible 
granular formulations described in U.S. Pat. No. 3,920,442 are useful 
herein with the present herbicidal compounds. In use by the farmer on the 
field, the granular formulations, emulsifiable concentrates, flowable 
concentrates, solutions, etc., may be diluted with water to give a 
concentration of active ingredient in the range of say 0.1% or 0.2% to 
1.5% or 2%. 
The active herbicidal compositions of this invention may be formulated 
and/or applied with insecticides, fungicides, nematicides, plant growth 
regulators, fertilizers, or other agricultural chemicals and may be used 
as effective soil sterilants as well as selective herbicides in 
agriculture. In applying an active composition of this invention, whether 
formulated alone or with other agricultural chemicals, an effective amount 
and concentration of the active compounds are of course employed; for 
example, amounts as low as 1 g/ha or less, e.g. 1-125 g/ha, may be 
employed for control of broadleafed weeds with little or no injury to 
crops such as maize or wheat. For field use, where there are losses of 
herbicide, higher application rates (e.g. four times the rates mentioned 
above) may be employed. 
Herbicidal Activity 
The test species used in demonstrating the herbicidal postemergence 
activity of the compositions of this invention are set forth in each of 
the tables below. These tests were conducted on populations of these 
species located in fields at various locations in the United States, the 
United Kingdom or France. The crops were planted; the weeds were either 
planted or grew naturally at these locations. 
Test plots were typically 10.0 ft by 20.0 ft, with 6.7 ft by 20.0 ft 
treated with a given rate of a herbicide or herbicide combination. (At any 
given location these were at least three, and most always, four 
replications of the individual treatments.) Control of the weed species 
and injury to the crop was assessed on a percent basis, relative to the 
nearest untreated area. Percent control was determined by a method similar 
to the 0 to 100 rating system disclosed in "Research Methods in Weed 
Science," 2nd ed., B. Truelove, Ed.; Southern Weed Science Society; Auburn 
University, Auburn, Ala., 1977. This rating system is set forth in the 
following table, captioned "Herbicide Rating System." 
The herbicides were applied to the test area by spraying an aqueous 
solution or suspension or emulsion of the compound or combination of 
compounds over the entire designated area. The formulated herbicides were 
diluted to a concentration appropriate for the desired application rate on 
the basis of a spraying rate of 20 gallons per acre. Unless otherwise 
noted, no surfactant or other adjuvant was added to the spray solution. 
For example, to treat the four test replicates at a single location with 
0.031 lb/acre of Compound P, 1.04 ml of the 2 lb/gal emulsifiable 
concentrate formulation was mixed with 1500 ml of water. The solution was 
sprayed through T-Jet Flat Fan 8002E nozzles (T-Jet Spraying Systems.TM.) 
at 30 psi pressure. 
Applications were typically made when the weed species were 1-3 inches 
tall. Percent control was rated at various times after application, as 
shown in the tables below, using the following "Rating System." 
______________________________________ 
Herbicide Rating System 
Rating Description 
Percent 
of Main Crop Weed 
Control 
Categories Description Description 
______________________________________ 
0 No effect No crop No weed 
reduction control 
or injury 
10 Slight dis- Very poor weed 
coloration control 
or stunting 
20 Slight Some dis- Poor weed 
effect coloration, control 
stunting or 
stand loss 
30 Crop injury Poor to 
more pronounced 
deficient weed 
but not lasting 
control 
40 Moderate injury, 
Deficient weed 
crop usually control 
recovers 
50 Moderate Crop injury Deficient to 
effect more lasting, 
moderate weed 
recovery doubtful 
control 
60 Lasting crop Moderate weed 
injury, no control 
recovery 
70 Heavy injury and 
Control some- 
stand loss what less than 
satisfactory 
80 Severe Crop nearly Satisfactory 
destroyed, a to good weed 
few survivors 
control 
90 Only occasional 
Very good to 
live plants left 
excellent 
control 
100 Complete Complete crop 
Complete weed 
effect destruction destruction 
______________________________________ 
TABLES 
Herbicidal data at selected application rates are given for various 
compounds of the invention in the tables below. The test compounds are 
identified in footnotes of the tables. 
In Tables I-IX the triazolinone 
ethyl-2-chloro-3-[2-chloro-4-fluoro-5-(4-difluoromethyl-4,5-dihydro-3-meth 
yl-5-oxo-(1H)-1,2,4-triazol-I-yl)phenyl]propionate (designated in the 
tables as "Compound P") was employed, but it will be understood that other 
triazolinones described above may be employed instead. 
The other active ingredients of the claimed herbicidal compositions are as 
identified in the tables. 
The scientific names of all the weed species used in these trials are 
presented in Table X. 
In the tables, the tests were carried out using formulations in which 
Compound P was first admixed with varying amounts of surfactants and 
aromatic hydrocarbon solvents. These formulations were then applied to 
various test plants, and at various rates, as indicated in these tables, 
using the triazolinone Compound P in combination with the other herbicides 
of this invention, also indicated in these tables. 
Examples of two such formulations of Compound P employed herein are as 
follows: 
______________________________________ 
wt/% 
______________________________________ 
Components (50 g/liter) 
Cmpd P (91.1% purity) 
6.06 
Emulsifier 1.sup.a 3.20 
Emulsifier 2.sup.b 3.20 
Dispersant.sup.c 1.60 
Aromatic 100 (solvent).sup.d 
85.94 
First Formulation (2 lbs/gal) 
Cmpd P (95% purity) 26.97 
Emulsifier 1.sup.a 1.95 
Emulsifier 2.sup.b 2.60 
Dispersant.sup.c 1.95 
Aromatic 100.sup.d 66.53 
Second Formulation (2 lbs/gal) 
Cpmd P (91.4% purity) 
24.42 
Emulsifier 1.sup.a 3.50 
Emulsifier 2.sup.b 1.40 
Dispersant.sup.c 2.10 
Aromatic 200.sup.e 68.58 
______________________________________ 
.sup.a An emulsifier consisting of 64% of an anionic calcium salt of 
dodecylbenzene sulfonate, 16% of a nonionic 6molar ethylene oxide 
condensation product of nonylphenol, and 20% butanol (Whitco Chemical 
Corp., Organics Div., New York, NY) 
.sup.b An emulsifier consisting of 56% of an anionic calcium salt of 
dodecylbenzene sulfonate, 24% of a nonionic 30molar ethylene oxide 
condensation product of nonylphenol, and 20% butanol (Whitco Chemical 
Corp., Organics Div., New York, NY) 
.sup.c A dispersant consisting of a nonionic paste of 100% polyalkylene 
glycol ether (Union Carbide Chemical and Plastics Co. Inc., Danbury, CT) 
.sup.d B.P. 156-167.degree. C. (Exxon Chemical Co., Houston, Texas) 
.sup.e B.P. 231-233.degree. C. (Exxon Chemical Co., Houston, Texas) 
Of these latter two solvents, the second formulation, which was less 
phytotoxic, is preferred. 
The formulations of the 2,4-D and sulfonylurea components described in the 
tables are all well-known to those skilled in the art, and are 
commercially available materials which may be routinely mixed with the 
above Compound P formulations at desired ratios and dilutions, desirably 
with water, necessary to obtain the application rates specified in the 
tables. 
It will be apparent that various modifications may be made in the 
formulations and applications of the compositions of this invention 
without departing from the inventive concepts herein as defined in the 
claims. 
TABLE I 
__________________________________________________________________________ 
Weed Control by Compound P Alone and in Combination with 
Express .RTM..sup.(a) and 
Harmony .RTM..sup.(b) Herbicides Evaluated 23 Days after Treatment 
Cpd. P 
Express Harmony 
Alone Alone Comb. Alone Comb. 
Weed Species 
L H L H LL LH HL HH L H LL LH HL HH 
Appln. Rate.sup.(c) 
Percent Control 
__________________________________________________________________________ 
Redroot Pigweed 
95 100 
82 89 95 100 
99 100 
100 
100 
100 
100 
100 
100 
Giant Ragweed 
30 55 56 65 54 68 58 63 83 86 84 88 
83 91 
Common 68 94 100 
100 
98 100 
98 100 
100 
99 99 100 
100 
100 
Lambsquarter 
Wild Sunflower 
56 78 84 93 78 90 79 95 100 
100 
100 
100 
100 
100 
Kochia 64 83 98 100 
78 99 96 96 90 93 93 100 
97 99 
Wild Buckwheat 
48 61 64 50 41 80 68 80 92 96 95 100 
97 99 
Russian Thistle 
66 87 100 
100 
94 100 
88 98 100 
100 
99 100 
99 99 
Wild Mustard 
24 31 99 98 81 99 89 99 75 86 74 84 
80 84 
Wild Garlic 
54 69 73 83 78 88 74 86 96 94 88 94 
90 93 
__________________________________________________________________________ 
Application Rate.sup.(c) 
Compound Low Rate (L) 
High Rate (H) 
__________________________________________________________________________ 
Compound P 0.008 0.015 
Express 0.004 0.008 
Harmony 0.008 0.015 
__________________________________________________________________________ 
L = Low rate 
H = High Rate 
LL = Low rate of Cpd. P + low rate of standard 
LH = Low rate of Cpd. P + high rate of standard 
HL = High rate of Cpd. P + low rate of standard 
HH = High rate of Cpd P + high rate of standard 
.sup.(a) Express: methyl 
2[[[[N(4-methoxy-6-methyl-1,3,5-triazin-2-yl)methylamino]carbonyl]amino]s 
lfonyl]benzoate (tribenuronmethyl) (DuPont, Wilmington, Del.) 
.sup.(b) Harmony: methyl 
3[[[[(4methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]amino]sulfonyl2 
thiophenecarboxylate (thifensulfuronmethyl) (DuPont, Wilmington, Del.) 
.sup.(c) Rate of application is in pounds of active ingredient/acre (lb/a 
TABLE II 
______________________________________ 
Percent Weed Control by Compound P Alone and in 
Combination with Express .RTM. Herbicide in Winter Barley 
and Winter Wheat Evaluated 22 Days After Treatment 
Cpd. P Express Cpd. P + Express 
Weed Species (7 g/ha).sup.(a) 
(19 g/ha) 
(7 + 19 g/ha) 
______________________________________ 
Catchweed Bedstraw 
100 65 97 
Red Deadnettle 
93 97 100 
Wild Chamomile 
97 97 97 
Field Forget-Me-Not 
95 97 100 
Corn Poppy 61 99 95 
Common Chickweed 
99 100 100 
Ivyleaf Speedwell 
92 92 97 
Persian Speedwell 
65 85 97 
Field Violet 65 90 97 
______________________________________ 
TABLE III 
__________________________________________________________________________ 
Percent Weed Control by Compound P Alone and in Combination with Ally 
.RTM. .sup.(b) 
Herbicide Evaluated 30 Days After Treatment 
Percent Control 
Rate Common 
Ivyleaf 
Prostate 
Herbicide 
g/ha.sup.(a) 
Pineappleweed 
Field Violet 
Mouseearcress 
Blackgrass 
Chickweed 
Speedwell 
Knotweed 
__________________________________________________________________________ 
Cpd. P 
10 19 0 0 0 69 96 99 
15 25 10 0 0 71 99 99 
30 39 17 14 0 81 100 100 
60 56 36 25 0 86 100 100 
Ally 3 34 0 0 0 81 7 95 
Cpd. P + 
15 + 3 
53 47 33 0 89 100 100 
Ally 
__________________________________________________________________________ 
.sup.(a) Rate of application is in grams of active ingredient/hectare 
(g/ha) 
.sup.(b) Ally: methyl 
2[[[[(4methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]amino]sulfonyl] 
enzoate (metsulfuronmethyl) (DuPont, Wilmington, Del.) 
TABLE IV 
__________________________________________________________________________ 
Postemergence Wheat Tolerance (Percent Injury) of Compound P Alone and in 
Combination 
with Ally .RTM. Herbicide 7 Days After Treatment and Weed Control 30 Days 
After Treatment 
Percent Control 
PI.sup.(b) Field- 
Rate To Catchweed 
Field 
Persian 
Common 
Forget- 
Cutleaf 
Red Ivyleaf 
Herbicide 
g/ha.sup.(a) 
Wheat 
Bedstraw 
Violet 
Speedwell 
Chickweed 
Me-Not 
Cranesbill 
Deadnettle 
Speedwell 
__________________________________________________________________________ 
Cpd. P 
7.5 1 78 13 10 10 13 30 8 15 
15 4 89 11 12 6 7 10 13 69 
30 8 96 45 12 9 5 10 8 89 
Ally 6 0 14 79 74 78 55 73 64 0 
Cpd. P + 
7.5 + 6 
1 67 81 67 73 53 80 54 30 
Ally 15 + 6 
3 79 92 86 89 83 93 82 81 
__________________________________________________________________________ 
.sup.(a) Rate of application is in grams of active ingredient/hectare 
(g/ha). 
.sup.(b) PI is percent injury to wheat. 
TABLE V 
______________________________________ 
Percent Control of Weeds and Tolerance of Wheat 
(Percent Injury) with Compound P Alone and in 
Combination with Ally .RTM. Herbicide 
Percent Control 
Percent Catch- 
Injury to 
White Persian weed 
Rate Wheat Mustard 
Speedwell 
Bedstraw 
Herbicide 
g/ha.sup.(a) 
7 DAT.sup.(b) 
30 DAT 30 DAT 30 DAT 
______________________________________ 
Cpd. P 10 2 71 91 90 
15 4 90 95 92 
30 6 95 99 96 
60 12 99 99 98 
Ally 3 0 35 69 25 
Cpd. P + 
15 + 3 4 98 99 97 
Ally 
______________________________________ 
.sup.(a) Rate of application is in grams of active ingredient/hectare 
(g/ha). 
.sup.(b) Represents days after treatment. 
TABLE VI 
__________________________________________________________________________ 
Percent Weed Control and Percent Wheat Discoloration by Compound P Alone 
and in Combination with Ally .RTM. Herbicide in Spring Wheat Evaluated 7 
and 21 
Days After Treatment 
Redroot 
Common Wild Russian 
PD.sup.(b) in 
Pigweed 
Lambsquarters 
Tansymustard 
Kochia 
Buckwheat 
Thistle 
Rate Spring Wheat 
Percent Control 
Herbicide 
lb/a.sup.(a) 
7 21 21 21 21 21 21 
__________________________________________________________________________ 
Cpd. P 
0.015 
2 43 45 95 23 43 25 
0.031 
4 63 80 100 45 50 43 
Ally 0.002 
0 90 10 100 10 65 30 
Cpd. P + 
0.015 
3 90 55 100 33 40 50 
Ally + 
0.002 
0.031 
3 84 75 100 38 80 53 
+ 
0.002 
__________________________________________________________________________ 
.sup.(a) Rate of application is in pounds of active ingredient/acre 
(lb/a). 
.sup.(b) PD is percent discoloration in wheat. 
TABLE VII 
__________________________________________________________________________ 
Percent Weed Control by Compound P Alone and in Combination with Ally 
.RTM. Herbicide in Spring Wheat 
Evaluated 30 Days After Treatment 
Percent Control 
Pennsyl- 
Wild 
Common Wild 
vania Common 
Rate Redroot 
Common 
Sun- 
Marsh- Buck- 
Smart- 
Russian 
Wild Velvet- 
Lambs- 
Herbicide 
lb/a.sup.(a) 
Pigweed 
Ragweed 
flower 
elder 
Kochia 
wheat 
weed Thistle 
Mustard 
leaf quarters 
__________________________________________________________________________ 
Cpd. P 
0.031 
87 0 92 98 89 40 10 86 54 95 97 
0.063 
96 3 95 98 96 75 13 95 60 99 100 
Cpd. P + 
0.031 
92 13 97 98 91 33 99 89 98 -- -- 
Ally + 
0.002 
__________________________________________________________________________ 
.sup.(a) Rate of application is in pounds of active ingredient/acre 
(lb/a). 
Tables VIII and IX (below) demonstrate the improved effect obtained in 
controlling weeds in post-emergence spring and winter wheat by combining 
2,4-dichlorophenoxy acetic acid ethyl ester ("2,4-D ester") with Compound 
P, as compared with the effect of either component alone. 
In Tables VIII and IX the expected synergistic effect was calculated as 
follows, using the Compound P observed values at 0.031 lb./a, and the 
2,4-D observed values at 0.50 lb./a: 
##EQU1## 
In these two tables (VIII and IX) the formulations employed comprised for 
Compound P a 2.0 lb/gal. emulsifiable concentrate; and for the 2,4-D ethyl 
ester a commercially available emulsifiable concentrate, each diluted to 
obtain the indicated application rates. 
TABLE VIII 
__________________________________________________________________________ 
PERCENT CONTROL OF WEEDS IN WINTER WHEAT WITH A CMPD P COMBINATION 
WITH 2,4-D ISOOCTYL ESTER 15 DAYS AND 30 DAYS AFTER TREATMENT 
CMPD P CMPD P 2,4-D Ethyl Ester 
CMPD P Applied at 0.031 lb/a 
in 
Applied Alone 
Applied Alone 
Applied Alone 
Combination with 2,4-D Ethyl 
Ester 
at 0.031 lb/a 
at 0.063 lb/a 
at 0.5 lb/a 
Applied at 0.25 lb/a 
Plant Species Observed Observed Observed Observed Expected 
__________________________________________________________________________ 
15 DAYS AFTER TREATMENT 
Common Ragweed 0* 1 67 99 67 
Shepardspurse 30 95 15 87 41 
Bittercress 35 83 17 90 46 
Sticky Chickweed 
17 20 0 25 17 
Common Lambsquarter 
59 89 74 100 89 
Blue Mustard 68 81 32 89 78 
Field Bindweed 62 96 15 95 68 
Tansymustard 45 51 58 93 77 
Flixweed 80 94 23 94 85 
Bushy Wallflower 
82 96 29 92 87 
Pennsylvania Smartweed 
16 39 16 80 29 
Common Groundsel 
40 49 9 73 45 
Common Chickweed 
5 12 5 50 10 
Field Pennycress 
94 96 94 98 100 
Velvetleaf 99 100 97 100 100 
30 DAYS AFTER TREATMENT 
Shepardspurse 93 98 20 97 94 
Bittercress 90 95 77 95 98 
Smallseed Falseflax 
57 88 51 86 79 
Blue Mustard 51 64 43 96 72 
Tansymustard 68 63 88 100 96 
Flixweed 79 91 39 99 87 
Bushy Wallflower 
90 98 45 97 95 
Field Pennycress 
98 99 99 99 100 
Common Groundsel 
33 44 11 85 40 
Common Chickweed 
10 30 5 30 15 
White Clover 100 95 37 90 100 
Sticky Chickenweed 
40 10 5 24 43 
Common Lambsquarter 
60 89 93 100 97 
Field Bindweed 33 84 53 83 69 
Pennsylvania Smartweed 
25 73 15 92 36 
Velvetleaf 98 99 81 97 100 
Winter Wheat 4 -- 1 12 5 
__________________________________________________________________________ 
TABLE IX 
__________________________________________________________________________ 
PERCENT CONTROL OF WEEDS IN SPRING WHEAT WITH A CMPD P COMBINATION 
WITH 2,4-D ISOOCTYL ESTER 15 DAYS AND 30 DAYS AFTER TREATMENT 
CMPD P CMPD P 2,4-D Ethyl Ester 
CMPD P Applied at 0.031 lb/a 
in 
Applied Alone 
Applied Alone 
Applied Alone 
Combination with 2,4-D Ethyl 
Ester 
at 0.031 lb/a 
at 0.063 lb/a 
at 0.5 lb/a 
Applied at 0.25 lb/a 
Plant Species Observed Observed Observed Observed Expected 
__________________________________________________________________________ 
15 DAYS AFTER TREATMENT 
Redroot Pigweed 
82* 95 27 96 87 
Common Ragweed 0 1 45 99 45 
Wild Sunflower 85 91 88 88 98 
Common Marchelder 
91 90 79 95 98 
Kochia 80 90 47 95 89 
Wild Buckwheat 35 85 73 93 83 
Pennsylvania Smartweed 
9 9 25 62 32 
Russian Thistle 
73 88 36 94 83 
Common Lambsquarter 
100 100 98 100 100 
Velvetleaf 99 100 96 100 100 
30 DAYS AFTER TREATMENT 
Redroot Pigweed 
87 96 60 96 95 
Common Ragweed 0 3 95 100 95 
Wild Sunflower 92 95 97 92 100 
Common Marchelder 
98 98 98 97 100 
Kochia 89 96 71 95 97 
Wild Buckwheat 40 75 71 83 52 
Pennsylvania Smartweed 
10 13 24 50 32 
Russian Thistle 
86 95 73 96 96 
Common Lambsquarter 
97 100 91 99 100 
Wild Mustard 54 60 98 98 99 
Velvetleaf 95 99 78 97 99 
Spring Wheat 2 -- 0 10 2 
__________________________________________________________________________ 
TABLE X 
______________________________________ 
Weed Species Used in These Tests 
Common Name Scientific Name 
______________________________________ 
Redroot Pigweed Amaranthus retroflexus 
Giant Ragweed Ambrosia trifida 
Common Lambsquarters 
Chenopodium album 
Wild Sunflower Helianthus sp 
Kochia Kochia scoperia 
Wild Buckwheat Polygonum convolvulus 
Russian Thistle Salsola Kali 
Wild Mustard Brassica Kaber 
Wild Garlic Allium vineale 
Catchweed Bedstraw 
Galium aparine 
Red Deadnettle Lamium purpureum 
Wild Chamomile Matricaria chamomilla 
Field Forget-me-not 
Myosotis arvensis 
Corn Poppy Papaver rhoeas 
Common Chickweed Stellaria media 
Ivyleaf Speedwell Veronica hederaefolia 
Persian Speedwell Veronica persica 
Field Violet Viola arvensis 
Pineappleweed Matricaria matricarioides 
Mouseearcress Arabiodopsis thaliana 
Blackgrass Alopecurus myosuroides 
Prostate Knotweed Polygonum aviculare 
Cutleaf Cranesbill 
Geranium dissectum 
White Mustard Brassica hirta 
Tansymustard Descurainia pinnata 
Deadnettles Lamium sp 
Ryegrasses Lolium sp. 
Common Ragweed Ambrosia artemisiifolia 
Common Marshelder Iva xanthiafolia 
Pennsylvania Smartweed 
Polygonum pensylvanicum 
Velvetleaf Abutilon theophrasti 
______________________________________ 
From the above results in Tables I-IX it will be seen that generally, the 
combinations of Compound P with the herbicides disclosed herein do provide 
a broader spectrum of weed control than do each of the herbicides when 
tested alone. A brief discussion of the tables of data follows: 
In Table I, the combination of Compound P and Express herbicide provides 
greater control of wild buckwheat than either Compound P or Express 
herbicide when applied alone. The combination of Compound P and Harmony 
herbicide broadens the spectrum of activity of Compound P to include 
improved control of giant ragweed, wild sunflower, wild buckwheat, wild 
mustard, and wild garlic. 
In Table II, the combination of Compound P and Express herbicide provides 
greater control of corn poppy in winter wheat and winter barley than does 
Compound P alone. In addition, the combination of Compound P and Express 
herbicide provides greater control of persian speedwell and field violet 
than either compound when applied alone. 
In Table III, the combination of Compound P and Ally herbicide provides 
greater control of pineappleweed, field violet, and mouseearcress than 
either Compound P or Ally herbicide alone. 
In Table IV, the combination of Compound P and Ally herbicide appears to be 
particularly efficacious. The combination provides greater control of 
nearly all of the weed species (i.e. field violet, persian speedwell, 
common chickweed, field forget-me-not, cutleaf cranesbill, red deadnettle, 
and ivyleaf speedwell) than does either Compound P or Ally herbicide 
alone. The combination of Compound P and Ally herbicide provides greater 
than 75% control of all of the weed species in these trials. 
In Table V, the combination of Compound P and Ally herbicide provides 
nearly 100% control of persian speedwell and white mustard up to about 65 
days. 
Also, in Table V, the data shows that the combination of Compound P and 
Ally herbicide is essentially not phytotoxic to wheat. 
In Table VI, the combination of Compound P and Ally herbicide broadens the 
spectrum of activity of both compounds as compared to each when applied 
alone. The combination, again is essentially not phytotoxic to spring 
wheat. 
In Table VII, the combination of Compound P and Ally herbicide greatly 
increases the control of Pennsylvania smartweed and wild mustard as 
compared to the control shown by Compound P when applied alone. 
In Tables VIII and IX, Compound P and the 2,4-D ester were tested alone and 
in combination. The combinations provided a clear showing of synergism as 
evidenced by the comparison of the observed control from the combination 
with the expected (calculated) control, shown in the last two columns of 
Tables VIII and IX. Note especially the results for: 
common ragweed, shepherdspurse, bittercress, field bindweed, tansymustard, 
flixweed, Pennsylvania smartweed, and common groundsel, at 15 days after 
treatment in Table VIII; 
for blue mustard, flixweed, common groundsel, field bindweed, and 
Pennsylvania smartweed, at 30 days after treatment in Table VIII; 
for redroot pigweed, common ragweed, wild buckwheat, Pennsylvania 
smartweed, and russian thistle, at 15 days after treatment in Table IX; 
and 
for wild buckwheat, at 30 days after treatment in Table IX.