Disclosed are herbicidal compositions containing a combination of the compound 2-[1-(3-transchloroallyloxyimino)propyl]-5-(2-ethylthiopropyl)-3-hydroxy-2 -cyclohexene-1-one (or a herbicidally effective salt thereof) and the compound 2-[7-fluoro-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazine-6-yl]-4,5, 6,7-tetrahydro-1H-isoindole-1,3(2H)-dione. It has been found that this combination synergistically interacts so as to accelerate the post-emergent herbicidal activity of 2-[1-(3-trans-chloroallyloxyimino)propyl]-5-(2-ethylthiopropyl)-3-hydroxy- 2-cyclohexen-1-one (or its salt) against grassy weeds.

BACKGROUND OF THE INVENTION 
1. Field of the Invention 
The present invention is directed to a synergistic herbicidal composition 
having an enhanced speed-up or acceleration in its post-emergent 
herbicidal activity against grassy weeds. In particular, the present 
invention is directed to a herbicidal composition containing a 
herbicidally effective amount of the compound 
2-[1-(3-trans-chloroallyloxyimino)propyl]-5-(2-ethylthiopropyl)-3-hydroxy- 
2-cyclohexen-1-one or a herbicidally effective salt thereof. This compound 
is a known pre-emergent and post-emergent herbicide having herbicidal 
activity against grassy weeds. The composition of the present invention 
further contains the compound 
2-[7-fluoro-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazine-6-yl]-4,5, 
6,7-tetrahydro-1H-isoindole-1,3-(2H)-dione in an amount effective to 
accelerate the post-emergent herbicidal activity of 
2-[1-(3-trans-chloroallyloxyimino)propyl]-5-(2-ethylthiopropyl)-3-hydroxy- 
2-cyclohexen-1-one or its salt. The present invention is based upon my 
discovery that the compound 
2-[7-fluoro-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazine-6-yl]-4,5, 
6,7-tetrahydro-1H-isoindole-1,3(2H)-dione unexpectedly and synergistically 
interacts with the compound 
2-[1-(3-trans-chloroallyloxyimino)propyl]-5-(2-ethylthiopropyl)-3-hydroxy- 
2-cyclohexen-1-one or its salt to provide for a marked acceleration in the 
herbicidal activity of this latter compound against grassy weeds. 
2. Description of the Related Art 
U.S. Pat. Nos. 4,640,707 and 4,792,605 describe the compound 
2-[7-fluoro-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazine-6-yl]-4,5, 
6,7-tetrahydro-1H-isoindole-1,3(2H)-dione; compounds related thereto; the 
preparation of such compounds; and the fact that these compounds possess 
herbicidal activity. In practice, while the compound 
2-[7-fluoro-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazine-6-yl]-4,5, 
6,7-tetrahydro-1H-isoindole-1,3(2H)-dione has shown excellent herbicidal 
activity against dicotyledonous weeds, this compound possesses poorer 
post-emergent herbicidal activity against grassy weeds such as 
johnsongrass (sorghum halepense), etc. 
Reissue U.S. Pat. No. 32,489 as well as European Patent Application No. 
85/904 773 and International Patent Application WO 87/01699 disclose 
compounds such as 
2-[1-(3-trans-chloroallyloxyimino)propyl]-5-(2-ethylthiopropyl)-3-hydroxy- 
2-cyclohexen-1-one (and salts thereof, see also U.S. Pat. No. 4,741,768 for 
suitable salts) as well as disclose that these compounds possess 
pre-emergent and post-emergent herbicidal activity against grassy weeds. 
In practice, while the compound 
2-[1-(3-trans-chloroallyloxyimino)propyl]-5-(2-ethylthiopropyl)-3-hydroxy- 
2-cyclohexen-1-one (and its salts) possesses excellent herbicidal activity 
against grassy weeds, this compound has little or no activity against 
dicotyledonous weeds. Additionally, the post-emergent herbicidal activity 
of this compound against grassy weeds manifests itself over an extended 
period of time. Thus, when a herbicidally effective amount of this 
compound is applied against grassy weeds, a suitable high level of kill of 
such weeds, e.g., generally greater than 90%, usually occurs about 7-21 
days after application. While this delay between application and the 
resulting high levels of kill may in some circumstances be acceptable or 
even desirable, there are also circumstances where it would be desirable 
for the herbicidal activity of this compound to be accelerated. For 
example, in no-till planting of crops such as soybeans, peanuts, corn, 
etc., it is common practice for the seeds to be planted either shortly 
before or shortly after the application of a herbicidal composition 
designed to completely kill all of the existing weeds without the prior 
tilling of the soil to remove these weeds. In this circumstance, it would 
be desirable for a rapid burndown (kill) of all of the weeds so that the 
germinating crop seeds as well as the resulting seedlings do not have 
competition from these weeds for soil moisture and nutrients. Such a rapid 
burndown should preferably occur within 5 days after application of the 
herbicidal composition and even more preferably within 3 days. 
Accordingly, it is an object of this invention to provide for a herbicidal 
composition containing 
2-[1-(3-trans-chloroallyloxyimino)propyl]-5-(2-ethylthiopropyl)-3-hydroxy- 
2-cyclohexen-1-one (or its salt) in which the post-emergent herbicidal 
activity of this compound against grassy weeds is accelerated so that this 
compound could be more effectively used in herbicidal compositions 
employed in no-till planting. 
While it is common practice to attempt to design a herbicidal composition 
having a broad spectrum of herbicidal activity by combining two or more 
herbicides with limited activity, i.e., combining a herbicide having 
activity against grassy weeds with a herbicide having activity against 
dicotyledonous weeds, such compositions often do not result in the desired 
herbicidal activity. This result is attributed to some sort of antagonism 
between the herbicidal compounds. 
Accordingly, it is a further object of this invention to provide for a 
herbicidal composition having two or more herbicidal components which 
results in a complete burndown of both grassy and dicotyledonous weeds 
with little or no antagonism between the herbicidally active components. 
It is still a further object of this invention to provide for a herbicidal 
composition which results in the rapid burndown of grassy weeds as well as 
dicotyledonous weeds so that this composition could be used in no-till 
planting. 
These and other objects are achieved by the compositions of the present 
invention which provide for a composition containing both the compound 
2-[7-fluoro-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazine-6-yl]-4,5, 
6,7-tetrahydro-1H-isoindole-1,3(2H)-dione and the compound 
2-[1-(3-trans-chloroallyloxyimino)propyl]-5-(2-ethylthiopropyl)-3-hydroxy- 
2-cyclohexen-1-one (or a herbicidally effective salt thereof). In regard to 
this composition, none of the above cited references disclose this 
combination. 
SUMMARY OF THE INVENTION 
As noted above, the compound 
2-[1-(3-trans-chloroallyloxyimino)propyl]-5-(2-ethylthiopropyl)-3-hydroxy- 
2-cyclohexen-1-one (and its salts) possesses herbicidal activity against 
grassy weeds. In this context, the present invention is directed to the 
discovery that when this compound is combined with 
2-[7-fluoro-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazine-6-yl]-4,5, 
6,7-tetrahydro-1H-isoindole-1,3(2H)-dione, this combination results in the 
acceleration of the post-emergent herbicidal activity of this compound. 
Therefore, in one of its composition aspects, the present invention is 
directed toward a herbicidal composition comprising a biologically inert 
carrier; a herbicidally effective amount of the compound 
2-[1-(3-trans-chloroallyloxyimino)propyl]-5-(2-ethylthiopropyl)-3-hydroxy- 
2-cyclohexen-1-one or a herbicidally effective salt thereof; and an 
effective amount of the compound 
2-[7-fluoro-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazine-6-yl]-4,5, 
6,7-tetrahydro-1H-isoindole-1,3(2H)-dione to accelerate the post-emergent 
herbicidal activity of the former compound or its salt. 
As also noted above, the compound 
2-[7-fluoro-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazine-6-yl]-4,5, 
6,7-tetrahydro-1H-isoindole-1,3(2H)-dione possesses herbicidal activity, 
particularly against dicotyledonous weeds. Therefore, another composition 
aspect of this invention is directed toward a herbicidal composition 
comprising a biologically inert carrier; a herbicidally effective amount 
of the compound 
2-[1-(3-trans-chloroallyloxyimino)propyl]-5-(2-ethylthiopropyl)-3-hydroxy- 
2-cyclohexen-1-one or a herbicidally effective salt thereof; and a 
herbicidally effective amount of the compound 
2-[7-fluoro-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazine-6-yl]-4,5, 
6,7-tetrahydro-1H-isoindole-1,3(2H)-dione. This composition also provides 
for the accelerated post-emergent herbicidal activity of the compound 
2-[1-(3-trans-chloroallyloxyimino)propyl]-5-(2-ethylthiopropyl)-3-hydroxy- 
2-cyclohexen-1-one and its salts resulting in a quick burndown of both 
grassy and dicotyledonous weeds and is particularly useful in no-till 
planting of crops such as soybean, corn, peanuts, etc. 
The compositions of this invention result in the accelerated burndown of 
grasses. Therefore, in one of its method aspects, the present invention is 
directed toward a method for accelerating the post-emergent herbicidal 
activity of the compound 
2-[1-(3-trans-chloroallyloxyimino)propyl]-5-(2-ethylthiopropyl)-3-hydroxy- 
2-cyclohexen-1-one or a herbicidally effective salt thereof which comprises 
employing in combination with a herbicidally effective amount of this 
compound an effective amount of the compound 
2-[7-fluoro-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazine-6-yl]-4,5, 
6,7-tetrahydro-1H-isoindole-1,3(2H)-dione to accelerate the post-emergent 
herbicidal activity of the former compound. 
Another method aspect of the present invention is directed toward a method 
for killing grassy weeds which comprises applying to the grassy weeds or 
their growth medium, a herbicidal composition comprising a biologically 
inert carrier; a herbicidally effective amount of the compound 
2-[1-(3-trans-chloroallyloxyimino)propyl]-5-(2-ethylthiopropyl)-3-hydroxy- 
2-cyclohexen-1-one or a herbicidally effective salt thereof; and an 
effective amount of the compound 
2-[7-fluoro-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazine-6-yl]-4,5, 
6,7-tetrahydro-1H-isoindole-1,3(2H)-dione to accelerate the post-emergent 
herbicidal activity of the former compound or its salt. 
Still another method aspect of the present invention is directed toward a 
method for killing grassy and dicotyledonous weeds which comprises 
applying to said weeds or their growth medium a herbicidal composition 
comprising a biologically inert carrier; a herbicidally effective amount 
of the compound 
2-[1-(3-trans-chloroallyloxyimino)propyl]-5-(2-ethylthiopropyl)-3-hydroxy- 
2-cyclohexen-1-one or a herbicidally effective salt thereof; and a 
herbicidally effective amount of the compound 
2-[7-fluoro-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazine-6-yl]-4,5, 
6,7-tetrahydro-1H-isoindole-1,3(2H)-dione. 
Yet still another method aspect of the present invention is directed toward 
a method for the no-till planting of crops which comprises applying to the 
area planted with seeds for said crops either before or after the planting 
of said seeds, a herbicidal composition comprising a biologically inert 
carrier; a herbicidally effective amount of the compound 
2-[1-(3-trans-chloroallyloxyimino)propyl]-5-(2-ethylthiopropyl-3-hydroxy-2 
-cyclohexen-1-one or a herbicidally effective salt thereof; and a 
herbicidally effective amount of the compound 
2-[7-fluoro-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazine-6-yl]-4,5, 
6,7-tetrahydro-1H-isoindole-1,3(2H)-dione. This method is particularly 
suited for the no-till planting of soybeans, corn, peanuts, cotton, and 
grain sorghum, rice, etc.

DETAILED DESCRIPTION OF THE INVENTION 
The present invention is directed to compositions and methods which provide 
for accelerated post-emergent herbicidal activity for 
2-[1-(3-trans-chloroallyloxyimino)propyl]-5-(2-ethylthiopropyl)-3-hydroxy- 
2-cyclohexen-1-one or a herbicidally effective salt thereof. This compound 
possesses both pre-emergent and post-emergent herbicidal activity against 
grassy weeds such as johnsongrass (sorghum halepense), watergrass 
(echinochloa cuisgalli), etc. When so used, this compound will result in 
high levels of kill, e.g. &gt;90% of the grassy weeds, usually within 7-21 
days after application. On the other hand, the compositions of this 
invention, which also employ this compound, result in high levels of kill 
of grassy weeds within 5 days after application and generally within 3 
days after application. This result is surprising because the compound 
2-[7-fluoro-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazine-6-yl]-4,5, 
6,7-tetrahydro-1H-isoindole-1,3(2H)-dione, which is also employed in the 
composition of the present invention, does not possess superior herbicidal 
activity against grassy weeds. 
Prior to discussing this invention in detail, the following terms will 
first be defined. 
"2-[1-(3-trans-chloroallyloxyimino)propyl]-5-(2-ethylthiopropyl)-3-hydroxy- 
2-cyclohexen-1-one or a herbicidally effective salt thereof" means the 
compound represented by the formula: 
##STR1## 
wherein R is hydrogen or a herbicidally effective salt. Representative 
herbicidally effective salts include NH.sub.4.sup.+, Na.sup.+, K.sup.+, 
Ca.sup.++, etc. Methods for preparing this compound as well as its 
herbicidally effective salts are described in U.S. Reissue Pat. No. 
32,489, U.S. Pat. No. 4,741,768, and International Patent Application No. 
WO 87/01699 each of which are incorporated herein in their entirety. 
Additional synthetic procedures are disclosed in International Patent 
Application No. WO 86/02065 which is also incorporated herein by 
reference. The nomenclature employed in U.S. Reissue Pat. No. 32,489 is 
different from that employed herein. Thus, the compound described herein 
by the nomenclature 
"2-[1-(3-trans-chloroallyloxyimino)propyl]-5-(2-ethylthiopropyl)-3-hydroxy 
-2-cyclohexen-1-one" would be described in U.S. Reissue Pat. No. 32,489 by 
the nomenclature 
"trans-2-[1-(3-chloroallyloxyimino)propyl]-5-(2-ethylthiopropyl)cyclohexan 
e-1,3-dione". However, both names are in fact describing the same compound 
represented by the above formula. It is also noted that this compound 
exists in tautomeric forms and has optical isomers. Such tautomers and 
isomers are intended to be included within the above nomenclature. 
"2-[7-fluoro-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazine-6-yl]-4,5, 
6,7-tetrahydro-1H-isoindole-1,3(2H)-dione" means the compound represented 
by the formula: 
##STR2## 
The preparation of this compound is described in U.S. Pat. Nos. 4,640,707 
and 4,792,605 which are incorporated herein in their entirety. 
"Herbicidally effective adjuvants" refer to compounds or compositions which 
while not possessing herbicidal activity, enhance the herbicidal activity 
of the composition. Typically, herbicidally effective adjuvants include 
surfactants, petroleum oils and vegetable oils and are well known in the 
art. Typical surfactants include nonionic surfactants, cationic 
surfactants, and anionic surfactants. Suitable surfactants include X-77 
(registered trademark) surfactant (available from Valent USA), Triton Ag 
98 (Rohm & Haas Chemical Company, Philadelphia, Pa.); LI-700 (Loveland 
Industries, Greely, Colo.); sodium long-chain carboxylates, alkylaryl 
sulfonates, sodium lauryl sulfate, polyethylene oxides, lignin sulfonates 
and the like. Typical vegetable oils include soybean oil, cottonseed oil, 
etc. Suitable herbicidally effective adjuvants include 
Agridex.TM.--available from Helena Chemical (Memphis, Tenn.); 
Dash.TM.--available from BASF; Surfel.TM. available from Rhone-Poulanc, 
Raleigh, N.C.; Red Panther Super Oil--available from Red Panther Chemical 
Company, Clarksdale, Miss.; Peptoil--available from Drexel Chemical 
Company; and the like. Without being limited by any theory, it is believed 
that the adjuvant enhances herbicidal activity by facilitating penetration 
of the herbicide(s) across the cell wall of the plant thereby allowing for 
more rapid uptake of the herbicide by the plant. 
The adjuvant should be employed in an amount sufficient to permit 
enhancement of the herbicidal activity of the composition. Typically, when 
the herbicidal composition is a liquid, the adjuvant is employed at about 
0.1 to about 2.5 percent volume/volume of the total herbicidal 
composition; preferably, at from about 0.25 to about 1.5 percent 
volume/volume; and more preferably, at from about 0.75 to about 1.25 
percent volume/volume. It is understood that when an adjuvant, such as 
Agridex, is employed, the volume/volume percentages set forth above are 
for Agridex itself and not the petroleum oil portion contained therein. 
When the herbicidal composition is a powder or dust, the adjuvant is 
typically employed at about 0.1 to about 2.5 percent by weight of the 
total herbicidal composition. 
"Accelerating the post-emergent herbicidal activity" refers to the increase 
in speed with which the herbicidal composition of this invention results 
in a kill of at least 80%, and preferably at least 90%, of the grassy 
weeds treated with this composition as compared to the time it takes for a 
similar herbicidal composition containing the compound 
2-[1-(3-trans-chloroallyloxyimino)propyl]-5-(2-ethylthiopropyl)-3-hydroxy- 
2-cyclohexen-1-one (or its salt), as the only active herbicidal agent, to 
kill at least 80%, and preferably, at least 90%, of the same weeds treated 
with this latter composition. Preferably, the acceleration of the 
post-emergent herbicidal activity resulting from the composition of this 
invention should be at least 20%, and more preferably, at least 30%, 
faster than the post-emergent herbicidal activity arising from a similar 
herbicidal composition containing the compound 
2-[1-(3-trans-chloroallyloxyimino)propyl]-5-(2-ethylthiopropyl)-3-hydroxy- 
2-cyclohexen-1-one as the only active herbicidal agent wherein both 
compositions employ the same amount of this compound. Accordingly, if the 
herbicidal composition containing the compound 
2-[1-(3-trans-chloroallyloxyimino)propyl]-5-(2-ethylthiopropyl)-3-hydroxy- 
2-cyclohexen-1-one requires 10 days after application to exhibit its 
post-emergent herbicidal activity, the herbicidal composition of this 
invention should exhibit such post-emergent herbicidal activity at least 
by 8 days after application and preferably at least by 7 days after 
application. In general, accelerations in the order of 50% or more can be 
achieved by the composition of this invention. 
COMPOSITIONS 
The compositions of the present invention employ the compound 
2-[1-(3-trans-chloroallyloxyimino)propyl]-5-(2-ethylthiopropyl)-3-hydroxy- 
2-cyclohexen-1-one or a herbicidally effective salt thereof as a grassy 
weed herbicide. This compound is employed in the herbicidal composition in 
an amount sufficient to be herbicidally effective. That is to say 
sufficient amounts of this compound should be employed in the herbicidal 
composition so as to result in phytotoxicity to the treated grassy weeds. 
Generally, for both pre-emergent and post-emergent herbicidal control, 
this compound is employed at a rate of about 0.06 lb/acre to about 0.25 
lb/acre. For post-emergence control, this compound is preferably employed 
in the compositions of this invention at a rate of about 0.075 lb/acre to 
about 0.125 lb/acre; and even more preferably at about 0.10 lb/acre. 
The compositions of the present invention also employ the compound 
2-[7-fluoro-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazine-6-yl]-4,5, 
6,7-tetrahydro-1H-isoindole-1,3(2H)-dione. The amount of this compound 
employed in the compositions of this invention depends on the intended use 
of the composition. Thus, if the composition is intended only to kill 
grassy weeds, then the amount of this compound used in this composition 
need only be sufficient to accelerate the post-emergent activity of 
2-[1-(3-trans-chloroallyloxyimino)propyl]-5-(2-ethylthiopropyl)-3-hydroxy- 
2-cyclohexen-1-one (or a salt thereof) against grassy weeds. In this 
circumstance, because the compound 
2-[7-fluoro-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazine-6-yl]-4,5, 
6,7-tetrahydro-1H-isoindole-1,3(2H)-dione lacks superior herbicidal 
activity against grassy weeds, use of quantities of this compound in 
excess of the amount required to accelerated the post-emergent herbicidal 
activity of the compound 
2-[1-(3-trans-chloroallyloxyimino)propyl]-5-(2-ethylthiopropyl)-3-hydroxy- 
2-cyclohexen-1-one (or its salt) is unnecessary. In general, amounts of 
about 0.5 g/acre and greater of the compound 
2-[7-fluoro-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazine-6-yl]-4,5, 
6,7-tetrahydro-1H-isoindole-1,3(2H)-dione are sufficient to accelerate the 
post-emergent herbicidal activity of the compositions of this invention 
against grassy weeds. Preferably, the compound 
2-[7-fluoro-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazine-6-yl]-4,5, 
6,7-tetrahydro-1H-isoindole-1,3(2H)-dione is employed at a rate of about 
0.5 g/acre to 10 g/acre, and more preferably at a rate of 1 g/acre to 5 
g/acre to accelerate the post-emergent herbicidal activity of the present 
compositions against grassy weeds. 
If the composition of the present invention is intended to kill both grassy 
weeds and dicotyledonous weeds, then the amount of the compound 
2-[7-fluoro-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazine-6-yl]-4,5, 
6,7-tetrahydro-1H-isoindole-1,3(2H)-dione employed in this composition 
should be sufficient to be herbicidally effective. That is to say 
sufficient amounts of this compound should be employed in the herbicidal 
composition so as to result in phytotoxicity to the treated dicotyledonous 
weeds. While amounts as low as 0.25 gm/acre of this compound are 
phytotoxic to some dicotyledonous weeds, this compound is generally 
employed in the compositions of this invention at a rate of at least about 
10 g/acre in order to be phytotoxic to all of the treated dicotyledonous 
weeds such as is necessary when conducting no-till planting. For 
pre-emergent control, this compound is preferable employed at a rate of 
about 1 g/acre to about 75 g/acre. For post-emergent control, this 
compound is preferably employed in the compositions of this invention at a 
rate of at least about 10 g/acre; more preferably at about 20 g/acre to 
about 40 g/acre; and even more preferably at about 25 g/acre. 
The ratio of 
2-[1-(3-trans-chloroallyloxyimino)propyl]-5-(2-ethylthiopropyl)-3-hydroxy- 
2-cyclohexen-1-one (or its salt) to 
2-[7-fluoro-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazine-6yl]-4,5,6 
,7-tetrahydro-1H-isoindole-1,3(2H)-dione employed in the compositions of 
this invention also depends on the intended use of the composition. In 
particular, if the composition is intended only to kill grassy weeds, then 
this ratio can range from about 2.5:1 to about 225:1. On the other hand, 
if the composition is intended for use in no-till planting, then this 
ratio can range from about 1:1.5 to about 10:1, with a preferred ratio of 
2:1. 
In a preferred embodiment, the compositions of this invention also employ a 
herbicidally effective adjuvant described above at rates which are also 
described above. Preferred adjuvants are petroleum oil based or vegetable 
oil based adjuvants. Particularly preferred adjuvants include Agridex.TM. 
available from Helena Chemical, and X-77 (registered trademark) available 
from Valent U.S.A. 
The compositions of this invention can also include extenders. In such a 
case, the compounds employed in the compositions of this invention can be 
extended with a carrier material (extender) of the kind used and commonly 
referred to in the art as inert solids, water and organic liquids. 
The compounds employed in this invention will be included in sufficient 
amounts so as to provide the desired effect. Usually, the formulation will 
contain from about 0.5 to 95% by weight of such compounds. Obviously, 
higher amounts of compounds in the formulation will require that lesser 
amounts of the formulation be applied per acre to obtain the desired 
application rate of the compounds. 
Solid compositions can be made with inert powders. The compositions thus 
can be homogeneous powders that can be used as such, diluted with inert 
solids to form dusts, or suspended in a suitable liquid medium for spray 
application. The powders usually comprise the active ingredients admixed 
with minor amounts of conditioning agent. Natural clays, either 
absorptive, such as attapulgite, or relatively non-absorptive, such as 
china clays, diatomaceous earth, synthetic fine silica, calcium silicate 
and other inert solid carriers of the kind conventionally employed in 
powdered herbicidal compositions can be used. The active ingredients 
usually make up from 0.5-90% or these powder compositions. The solids 
ordinarily should be very finely divided. For conversion of the powders to 
dusts, talc, pyrophyllite, and the like, are customarily used. 
Liquid compositions including the active compounds described above can be 
prepared by admixing the compounds with a suitable liquid diluent medium. 
Typical of the liquid media commonly employed are methanol, benzene, 
toluene, and the like. The active ingredients usually make up about 0.5 to 
50% of these liquid composition. Some of these compositions are designated 
to be used as such, and others to be extended with large quantities of 
water. 
Compositions in the form of wettable powders or liquids can also include 
one or more surface-active agents, such as wetting, dispersing or 
emulsifying agents. The surface-active agents cause the compositions of 
wettable powders or liquids to disperse or emulsify easily in water to 
give aqueous sprays. 
The surface-active agents employed can be of the anionic, cationic or 
nonionic type. They include, for example, sodium long-chain carboxylates, 
alkyl aryl sulfonates, sodium lauryl sulfate, polyethylene oxides, lignin 
sulfonates and other surface-active agents. 
When used as a pre-emergent treatment, it is desirable to include a 
fertilizer, an insecticide, a fungicide or another herbicide. 
While the compositions of the present invention are, in general, herbicidal 
in both pre- and post-emergent applications, the post-emergent application 
is preferred particularly in view of the acceleration of the post-emergent 
herbicidal activity against grassy weeds demonstrated by the compositions 
of this invention. 
For pre-emergent control of undesirable vegetation, the herbicidal 
compositions will be applied in herbicidally effective amounts to the 
locus or growth medium of the vegetation, e.g., soil infested with seeds 
and/or seedlings of such vegetation. Such application will inhibit the 
growth of or kill the seeds, germinating seeds and seedlings. 
For post-emergent applications, the herbicidal compositions of the 
invention will be applied directly to the foliage and other plant parts. 
Generally, the herbicidal compositions of the invention are especially 
effective against grassy weeds because of its accelerated activity against 
such weeds. The herbicidal composition of the invention is also especially 
effective in providing for a rapid burndown of both grassy weeds and 
dicotyledonous weeds as is required in no-till planting of crops. However, 
when so used, it is necessary that the herbicidal composition employ a 
herbicidally effective amount of 
2-[7-fluoro-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazine-6-yl]-4,5, 
6,7-tetrahydro-1H-isoindole-1,3(2H)-dione. Also, when such a composition is 
used in no-till planting, it is preferable that the composition be applied 
either prior to planting of the crop seeds or after planting of such seeds 
but prior to emergence of the seedlings so as to avoid possible damage or 
injury to the crop. In general, the composition can be applied up to about 
30 days prior to planting of the seeds, although preferably up to about 7 
days prior to planting Likewise, after planting the seeds and unless 
already so applied, the composition is preferably applied at any time 
after planting and prior to the emergence of the seedlings. 
In a preferred embodiment, the composition of the invention is applied 
shortly after, e.g., 1 to 3 days, planting of the seeds so as to 
substantially minimize the likelihood of seedling emergence. 
However, if after crop emergence application of the composition of the 
invention is desired, such application should not be applied to the crop 
since contact with the crop can result in crop damage. Methods of applying 
herbicidal compositions without contacting emerged crops are known in the 
art, e.g., post-directed applications. 
The following preparatory examples are directed to the preparation of the 
compounds employed in the present invention. 
PREATORY EXAMPLE A 
Preparation of 2-[1-(3-trans-chloroallyloxyimino) 
propyl]-5-(2-ethylthiopropyl)-3-hydroxy-b 2-cyclohexen-1-one 
In this example, 17.2 g (0.0636 mol) of 
2-propionyl-5-(2-ethylthiopropyl)cyclohexane-1,3-dione; 0.9 g (0.0153 mol) 
of acetic acid, and 10 9 g (0.0757 mol) of 3-trans-chloroallyloxyamine in 
35 ml of water are added to 20 ml of hexane and stirred. Aqueous 5 wt. 
percent sodium hydroxide is slowly added over about 15 minutes until 3.0 g 
(0.0757 mol+small excess) of sodium hydroxide is added--pH of reaction 
mixture about 6. The mixture is heated to and maintained at 40.degree. C. 
for 21/2 hours and then cooled to room temperature. The organic (i.e., 
hexane) phase is separated and washed with 10 ml of aqueous 5 weight 
percent hydrochloric acid and then aqueous 6.25 weight percent sodium 
hydroxide added until pH 12. The aqueous phase is separated and admixed 
with 25 ml of hexane and the pH adjusted to 5.4 by the dropwise addition 
of aqueous 36 weight percent hydrochloric acid over an ice bath. The 
organic phase is separated, dried over magnesium sulfate and then 
concentrated by evaporation affording the crude product. The crude product 
is purified by column chromatography over silica gel eluting with 
hexane:methylene chloride affording the purified title compound. 
PREATORY EXAMPLE B 
Preparation of 
2-[7-fluoro-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazine-6-yl]-4,5, 
6,7-tetrahydro-1H-isoindole-1,3(2H)-dione 
A. Iron powder (36.42 g) is suspended in 5% aqueous acetic acid (69 ml) and 
heated to 80.degree. C. To the suspension, a solution of ethyl 
5-fluoro-2-nitrophenoxyacetate (15.86 g) in acetic acid (65 ml) and ethyl 
acetate (65 ml) is dropwise added, and the resulting mixture is heated at 
60.degree. to 80.degree. C. under reflux for 3 hours. After removal of 
residue by filtration, the filtrate is extracted with ethyl acetate. The 
extract is washed with water and sodium bicarbonate solution, dried and 
concentrated to give 7-fluoro-3,4-dihydro-3-oxo-2H-1,4-benzoxazine. 
B. A solution of 7-fluoro-3,4-dihydro-3-oxo-2H-1,4-benzoxazine (2.0 gram) 
in 80% aqueous sulfuric acid (30 ml) is cooled to 0.degree. to 5.degree. 
C., and 60% nitric acid (1.6 g) is gradually added thereto at 0.degree. to 
5.degree. C. The resultant mixture is stirred at the same temperature for 
30 minutes and poured onto ice water. The precipitated crystals are 
collected by filtration, washed with water and dried to give 
7-fluoro-3,4-dihydro-3-oxo-6-nitro-2H-1,4-benzoxazine. 
C. A suspension of sodium hydride (0.06 g) in N,N-dimethylformamide (3 ml) 
is cooled to 0.degree. C. 
7-fluoro-3,4-dihydro-3-oxo-6-nitro-2H-1,4-benzoxazine (0.57 g) is added 
thereto at between 0.degree. to 5.degree. C., and the resultant mixture is 
stirred for 30 minutes. Propargyl bromide (0.35 g) is added to the 
mixture, which is gradually heated to room temperature, and the reaction 
is continued for 6 hours. After addition of water, the resultant mixture 
is extracted with ethyl acetate, and the extract is washed with water, 
dried and concentrated. The residue is purified by silica gel thin layer 
chromatography using a 1:1 mixture of ethyl acetate and n-hexane as the 
eluent to give 
7-fluoro-3,4-dihydro-3-oxo-6-nitro-4-(2-propynyl)-2H-1,4-benzoxazine. 
D. Iron powder (1.05 g) is suspended in 5% aqueous acetic acid (2.0 ml) and 
heated to 80.degree. C. To the suspension, a solution of 
7-fluoro-3,4-dihydro-3-oxo-6-nitro-4-(2-propynyl)-2H-1,4-benzoxazine (0.47 
g) in acetic acid (1.9 ml) and ethyl acetate (1.9 ml) is dropwise added, 
and the resulting mixture is heated under reflux at 60.degree. to 
80.degree. C. for 3 hours. After being allowed to cool, water and ethyl 
acetate are added to the mixture. The residue is removed by filtration, 
and the filtrate is extracted with ethyl acetate. The extract is washed 
with water and aqueous sodium bicarbonate solution, dried and concentrated 
to give 
6-amino-7-fluoro-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazine. 
E. A mixture of 
6-amino-7-fluoro-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazine (0.31 
g), 3,4,5,6-tetrahydrophthalic anhydride (0.28 g) and acetic acid (3 ml) 
is heated under reflux for 2 hours. After being allowed to cool, water is 
added to the mixture, which is then extracted with ethyl acetate. The 
organic layer is washed with water, neutralized with sodium bicarbonate 
solution, dried and concentrated. The residue is purified by silica gel 
thin layer chromatography using a (1:2) mixture of ethyl acetate and 
hexane as the eluent to give the title product. 
The following example is offered to illustrate the invention and should not 
be construed in any way as limiting the scope of this invention. 
EXAMPLE 1 
Post-Emergent Herbicidal Test 
Test compositions were formulated by combining the requisite amount of the 
compound 
2-[1-(3-trans-chloroallyloxyimino)propyl]-5-(2-ethylthiopropyl)-3-hydroxy- 
2-cyclohexen-1-one and the compound 
2-[7-fluoro-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazine-6-yl]-4,5, 
6,7-tetrahydro-1H-isoindole-1,3(2H)-dione into an aqueous formulation so as 
to provide, when applied, the concentrations set forth in Table I. When 
applied, each of these formulations also contained Agridex.TM.--available 
from Helena Chemical, at a concentration sufficient to provide 1 quart of 
Agridex.TM. per treated acre. 
TABLE I 
______________________________________ 
Formulation 
Concentration of Compound.sup.a 
No. A B C 
______________________________________ 
1 10.120 g/acre 
-- -- 
2 20.240 g/acre 
-- -- 
3 30.360 g/acre 
-- -- 
4 10.120 g/acre 
0.1 lb/acre 
-- 
5 20.240 g/acre 
0.1 lb/acre 
-- 
6 30.360 g/acre 
0.1 lb/acre 
-- 
7 -- 0.1 lb/acre 
-- 
8 -- 0.1 lb/acre 
0.37 lb/acre 
______________________________________ 
.sup.a concentration of compound as applied. 
A = 
2[7fluoro-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazine-6-yl4,5,6,7 
tetrahydro-1H-isoindole-1,3(2H)-dione 
B = 
2[1(3-trans-chloroallyloxyimino)propyl5-(2-ethylthiopropyl)-3-hydroxy-2-c 
clohexen-1-one 
C = Metribuzin commercially available as Sencor available from Mobay 
Chemical Company and used herein as a postemergent herbicide with activit 
against dicotyledonous weeds 
Each of these 8 test compositions were applied by foliar spray to the weeds 
under the following conditions: Row spacing 40 inches, gallons per acre 
20, PSI 20, nozzle size 8003, number of nozzles 4, nozzle spacing 20 
inches, applicator speed 3.16 miles per hour, air temperature 62.degree. 
F., soil temperature 69.degree. F., soil moisture-good, wind speed 0-3 
miles per hour from the south, weed stages Rhizome johnsongrass (sorghum 
halepense) 2-24 inches; teaweed (sida spinosa) 2 inches, 6 leaves; 
cocklebur (Xanthium Pensylvanicum) 3 inches; and spurge (euphorbia 
maculata) 0.5 to 3 inches, 3 leaves. Of the above weeds, the first weed is 
a grassy weed whereas the remaining three weeds are dicotyledonous weeds. 
After application, the percent kill of each of the weeds was visually 
determined at 3, 7 and 21 days after treatment. The results are set forth 
in Tables II-V below. 
TABLE II 
______________________________________ 
Percent kill of Rhizome johnsongrass 
Days After Treatment 
Formulation No. 
3 7 21 
______________________________________ 
1 45.00 22.50 0 
2 50.00 22.50 0 
3 52.50 22.50 0 
4 94.25 96.50 75.00 
5 96.50 97.00 73.75 
6 96.00 97.00 82.50 
7 32.50 50.00 92.50 
8 2.50 20.00 40.00 
______________________________________ 
TABLE III 
______________________________________ 
Percent kill of Teaweed 
Days After Treatment 
Formulation No. 
3 7 21 
______________________________________ 
1 95.25 91.00 83.75 
2 98.75 97.25 89.75 
3 97.75 97.75 96.25 
4 97.50 94.75 86.25 
5 98.75 98.00 94.25 
6 99.00 99.75 98.25 
7 2.50 0.00 0.00 
8 32.50 67.50 90.75 
______________________________________ 
TABLE IV 
______________________________________ 
Percent kill of cocklebur 
Days After Treatment 
Formulation No. 
3 7 21 
______________________________________ 
1 100.35.sup.a 100.00 -- 
2 99.89 100.00 -- 
3 96.65 100.00 -- 
4 99.00 100.00 -- 
5 100.36.sup.a 100.00 -- 
6 99.00 100.00 -- 
7 2.50 0.00 -- 
8 37.50 100.00 -- 
______________________________________ 
.sup.a percents over 100% were obtained as a result of computer 
extrapolations 
TABLE V 
______________________________________ 
Percent kill of spurge 
Days After Treatment 
Formulation No. 
3 7 21 
______________________________________ 
1 99.00 100.00 99.50 
2 99.00 100.00 99.75 
3 99.00 100.00 100.00 
4 99.00 100.00 97.00 
5 98.75 100.00 100.00 
6 99.00 100.00 100.00 
7 2.50 0.00 0.00 
8 40.00 40.00 12.50 
______________________________________ 
From the above data, it is seen that the herbicidal compositions containing 
the compound 
2-[7-fluoro-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazine-6-yl]-4,5, 
6,7-tetrahydro-1H-isoindole-1,3(2H)-dione as the only active herbicidal 
agent (formulations 1, 2 and 3) show some activity against Rhizome 
johnsongrass after 3 and 7 days but none after 21 days. On the other hand, 
this compound shows excellent activity against teaweed, cocklebur and 
spurge. This data substantiates the fact that this compound is an 
excellent post-emergent herbicide against dicotyledonous weeds while 
possessing poorer post-emergent herbicidal activity against grassy weeds. 
Also from the above data, it is seen that the herbicidal composition 
containing the compound 
2-[1-(3-trans-chloroallyloxyimino)propyl]-5-(2-ethylthiopropyl)-3-hydroxy- 
2-cyclohexen-1-one as the only active herbicidal agent (formulation 7) 
possesses excellent post-emergent herbicidal activity against Rhizome 
johnsongrass 21 days after application but possesses poorer activity 
against Rhizome johnsongrass 3 or 7 days after application. On the other 
hand, this compound possesses little or no post-emergent herbicidal 
activity against dicotyledonous weeds. This data substantiates the fact 
that the post-emergent herbicidal activity of this compound against grassy 
weeds manifests itself over an extended period of time. 
Again from the above data, it is seen that the herbicidal compositions 
containing both the compound 
2-[7-fluoro-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazine-6-yl]-4,5, 
6,7-tetrahydro-1H-isoindole-1,3(2H)-dione and the compound 
2-[1-(3-trans-chloroallyloxyimino)propyl]-5-(2-ethylthiopropyl)-3-hydroxy- 
2-cyclohexen-1-one as the only active herbicidal agents (formulations 4, 5 
and 6) possess the expected herbicidal activity against dicotyledonous 
weeds. However, these compositions show substantially accelerated 
herbicidal activity for Rhizome johnsongrass as compared to formulation 7. 
Because the activity against Rhizome johnsongrass at 3 and 7 days after 
treatment exceeds the additive result of each of these compounds used 
separately, this data substantiates the fact this combination 
synergistically interacts to accelerate the post-emergent herbicidal 
activity against grassy weeds. 
Lastly, comparison of the results of formulation 8 against formulation 7 
substantiate that the combination of the compound of formulation 7, a 
grassy weed herbicide, with Metribuzen.TM., a commercially available 
post-emergent herbicide for dicotyledonous weeds, results in antagonism 
between these compounds--at least with regard to the results of this 
combination against grassy weeds. On the other hand, the compounds 
employed in the compositions of this invention are not antagonistic toward 
each other, but are in fact synergistic.