This application discloses compounds of the structural formula: ##STR1## wherein each X is independently selected from the group consisting of oxygen and sulfur; m is 0 or 1; R is alkyl. Each R.sup.1 is independently selected from the group consisting of hydrogen and alkyl. Y is selected from the group consisting of alkyl and ##STR2## wherein each Z is independently selected from the group consisting of hydrogen and alkyl. These compounds are particularly useful as pre-emergence herbicides.

This invention relates to new heterocyclic aniline compounds useful as 
herbicides. In particular, this invention relates to compounds of the 
following structural formula: 
##STR3## 
wherein each X is independently selected from the group consisting of 
oxygen and sulfur; m is 0 or 1; R is alkyl; each R.sup.1 is independently 
selected from the group consisting of hydrogen and alkyl; and Y is 
selected from the group consisting of alkyl and 
##STR4## 
wherein each Z is independently selected from the group consisting of 
hydrogen and alkyl. 
In a preferred embodiment of this invention, each alkyl group in the above 
structural formula is a lower alkyl group. By lower alkyl it is meant 
straight or branched chain alkyl groups having from 1 to 6 carbon atoms. 
The compounds of the present invention can be prepared by the following 
reaction: 
##STR5## 
This reaction can be conveniently performed in the presence of an inert 
organic solvent such as toluene, heptane, xylene, benzene, etc. at an 
elevated temperature between about 60.degree. C. and about 150.degree. C. 
in the presence of an acid acceptor for the by-product hydrochloric acid 
such as pyridine or a tertiary amine. The reactants are added in 
approximately equimolar amounts, although a small excess (about 10%) of 
the compound of formula III can be preferred. After the addition of the 
reactants, solvent and acid acceptor, the mixture is heated to reflux and 
maintained at reflux from one to eight hours. Then the solvent and acid 
acceptor are removed from the system to yield the desired product. This 
product can be used as such or can be purified by conventional means such 
as recrystallization. 
All of the reactants are known in the literature. When desired the dinitro 
reactant can be readily prepared by nitration of the corresponding 
mononitro compound which are also reported in the literature. 
The manner in which the compounds of the present invention can be prepared 
is more specifically illustrated in the following examples.

EXAMPLE 1 
PREATION OF 4-CHLORO-3,5-DINITROPHENYLMETHYLSULFONE 
Red fuming nitric acid (15 ml) was added to fuming sulfuric acid [(30% 
oleum) 45 ml] contained in a three-necked glass reaction flask equipped 
with addition funnel, heating mantle, thermometer, stirrer and reflux 
condenser. The mix was maintained at a temperature of 5.degree.-25.degree. 
C. during the thirty minute addition and 
4-chloro-3-nitrophenylmethylsulfone (6 grams; 0.025 mol) was added 
portionwise to the reaction mixture and maintained at a temperature of 
over a period of thirty minutes. The reaction mixture was let stand 
overnight. It was then heated to 122.degree. C. and held there for four 
hours. After that time had elapsed, it was cooled to room temperature and 
the reaction mixture was quenched with ice and filtered to give a white 
solid (melting point 190.degree.-195.degree. C.). Chromatographic analysis 
indicated that this solid was the desired product. It was recrystallized 
from a mixture of dimethyl formamide and ethanol resulting in pale yellow 
crystals which washed with ethanol and dried. This product weighted 5.30 
grams and had a melting point of 197.degree.-199.degree. C. 
EXAMPLE 2 
PREATION OF 
N-[(1,3-DIOXOLAN-2-YL)METHYL]-N-ETHYL-4-METHYLSULFONYL-2,6-DINITROANILINE 
4-Chloro-3,5-dinitrophenylmethylsulfone (2 grams; 0.007 mol), 
N-ethyl-N-(1,3-dioxolan-2-yl methyl) amine (2.25 grams; 0.017 mol), 
triethylamine (10 ml), and toluene (30 ml) were added to a three-necked 
glass reaction flask equipped with thermometer, heating mantle, stirrer 
and reflux condenser. The reaction mixture was heated to reflux and 
maintained there overnight. Thin layer chromatographic analysis showed 
that the reaction was complete. The reaction mixture was cooled to room 
temperature. The triethylamine hydrochloride salt was filtered from the 
reaction mixture and the solvent was stripped off. The residue was washed 
with isopropanol and dried to give 2.0 grams or product (melting point 
125.degree.-127.degree. C.). 
______________________________________ 
Elemental Analysis: 
C H N S 
______________________________________ 
Theoretical: 41.60 4.57 11.20 
8.54 
Found: 41.71 4.66 11.02 
8.37 
______________________________________ 
EXAMPLE 3 
PREATION OF 
N-[(1,3-DIOXAN-2-YL)METHYL]-N-METHYL-4-METHYLSULFONYL-2,6-DINITROANILINE 
4-Chloro-3,5-dinitrophenylmethylsulfone (2 grams; 0.007 mol) and toluene 
(30 ml) were added to a three-necked glass reaction flask equipped with 
thermometer, heating mantle, stirrer and reflux condenser. 
N-Methyl-N-(1,3-dioxan-2-yl methyl) amine (2.25 grams; 0.017 mol) and 
triethylamine (10 ml) were added to the reaction mixture which refluxed 
overnight. Then the reaction mixture was cooled to room temperature and 
the triethylamine hydrochloride salt filtered from the reaction mixture. 
The solvent was stripped off and the residue washed with isopropanol and 
hexane to give the desired product. 
EXAMPLE 4 
PREATION OF 
N-[4,4,6,6-TETRAMETHYL-1,3-DIOXAN-2-YL)METHYL]-N-BUTYL-4-ETHYLAMIDOSULFONY 
L-2,6-DINITROANILINE 
4-Chloro-3,5-dinitrophenylethylamidosulfone (2 grams; 0.0065 mol) and 
toluene (30 ml) are added to a three-necked glass reaction flask equipped 
with thermometer, heating mantle, stirrer and reflux condenser. 
N-Butyl-N-(4,4,6,6-Tetramethyl-1,3-Dioxan-2-yl methyl) amine (2.50 grams; 
0.014 mol) and triethylamine (10 ml) are added to the reaction mixture 
which is refluxed overnight. Then the reaction mixture is cooled to room 
temperature. The triethylamine hydrochloride is filtered frowm the 
reaction mixture and the solvent is stripped off. The residue is washed 
with isopropanol to give the desired product. 
EXAMPLE 5 
PREATION OF 
N-[4,5-DI-n-BUTYL-1,3-DITHIOLAN-2-YL)METHYL]-N-METHYL-4-DIMETHYLAMIDOSULFO 
NYL-2,6-DINITROANILINE 
4-Chloro-3,5-dinitrophenyldimethylamidosulfone (2.0 grams; 0.0065 mol) and 
toluene (30 ml) are added to a three-necked glass reaction flask equipped 
with thermometer, heating mantle, stirrer and reflux condenser. 
N-Methyl-N-(4,5-di-n-butyl-1,3-dithiolan-2-yl methyl) amine (4.5 grams; 
0.015 mol) and triethylamine (10 ml) are added to the reaction mixture 
which is refluxed overnight. Then the reaction mixture is cooled to room 
temperature and the triethylamine hydrochloride filtered from the reaction 
mixture. The solvent is stripped off and the residue washed with 
isopropanol and hexane to give the desired product. 
EXAMPLE 6 
PREATION OF 
N-[(4,6-DIPENTYL-1-THIO-3-OXAN-2-YL)METHYL]-N-HEXYL-4-PROPYLSULFONYL-2,6-D 
INITROANILINE 
4-Chloro-3,5-dinitrophenylpropylsulfone (2.0 grams; 0.0065 mol) and toluene 
(30 ml) are added to a three-necked glass reaction flask equipped with 
thermometer, heating mantle, stirrer, and reflux condenser. 
N-Hexyl-N-(4,6-dipentyl-1-thio-3-oxan-2-yl methyl) amine (10 ml) are added 
to the reaction mixture which is refluxed overnight. The reaction mixture 
is cooled to room temperature. The triethylamine hydrochloride is filtered 
from the reaction mixture and the solvent is stripped off. The residue is 
washed with isopropanol and hexane and the desired product is obtained as 
a solid material. 
The following examples contain the reactants and the products which are 
obtained by using the procedure illustrated by the previous examples 
EXAMPLE 7 
4-Chloro-3,5-dinitrophenylmethylsulfone+[N-isopropyl-N-(1,3-dithian-2-yl)me 
thyl]amine=N-[(1,3-dithian-2-yl)methyl)methyl]-N-isopropyl-4-methylsulfonyl 
-2,6-dinitroaniline 
EXAMPLE 8 
4-chloro-3,5-dinitrophenylethylamidosulfone+(N-propyl-4,4,6-triethyl-1,3-di 
oxan-2-yl 
methyl)amine=N-[(4,4,6-triethyl-1,3-dioxan-2-yl)methyl]-N-propyl-4-ethylam 
idosulfonyl-2,6-dinitroaniline 
EXAMPLE 9 
4-chloro-3,5-dinitrophenylethylhexylamidosulfone+[N-methyl-N-(4-ethyl-5-pen 
tyl-3-oxa-1-thiolan-2-yl)methyl]amine=N-[(4-ethyl-5-pentyl-3-oxa-1-thiolan- 
2-yl)methyl]-N-methyl-4-ethylhexylamidosulfonyl-2,6-dinitroaniline 
EXAMPLE 10 
4-chloro-3,5-dinitrophenyldihexylamidosulfone+[N-butyl-N-(4,5-dipropyl-1,3- 
dioxolan-2-yl)methyl]amine=N-[4-dipropyl-1,3-dioxolan-2-yl)methyl]-N-butyl- 
4-dihexylamidosulfonyl-2,6-dinitroaniline 
EXAMPLE 11 
4-chloro-3,5-dinitrodiisopropylamidosulfone+[N-hexyl-N-(1,3-dithiolan-2-yl) 
methyl]amine=N-[(1,3-dithiolan-2-yl)methyl]-N-butyl-4-dihexylamidosulfonyl- 
2,6-dinitroaniline 
EXAMPLE 12 
4-chloro-3,5-dinitrophenylethylsulfone+[N-ethyl-N-(4,4-dibutyl-3-oxa-1-thia 
n-2-yl)methyl]amine=N-[(4,4-dibutyl-3-oxa-1-thian-2-yl)methyl]-N-ethyl-4-et 
hylsulfonyl-2,6-dinitroaniline 
EXAMPLE 13 
4-chloro-3,5-dinitrophenylpentylamidosulfone+[N-methyl-N-(4,4,6,6-tetraethy 
l-1,3-dithian-2-yl)methyl]amine=N-[(4,4,6,6-tetraethyl-1,3-dithian-2-yl)met 
hyl]-N-methyl-4-pentylamidosulfonyl-2,6-dinitroaniline 
EXAMPLE 14 
4-chloro-3,5-dinitrophenylpropylamidosulfone+[(N-isopropyl-4,4,6,6-tetraiso 
propyl-1,3-dioxan-2-yl)methyl]amine=N-[(4,4,6,6-tetraisopropyl-1,3-dioxan-2 
-yl)methyl]-N-isopropyl-4-dipropylsulfonyl-2,6-dinitroaniline 
For practical use as herbicides the compounds of this invention are 
generally incorporated into herbicidal compositions which comprise an 
inert carrier and a herbicidally toxic amount of such a compound. Such 
herbicidal compositions, which can also be called formulations, enable the 
active compound to be applied conveniently to the site of the weed 
infestation in any desired quantity. These compositions can be solids such 
as dusts, granules, or wettable powders; or they can be liquids such as 
solutions, aerosols or emulsifiable concentrates. 
For example, dusts can be prepared by grinding and blending the active 
compound with a solid inert carrier such as the talcs, clays, silicas, 
pyrophyllite, and the like. Granular formulations can be prepared by 
impregnating the compound, usually dissolved in a suitable solvent, onto 
and into granulated carriers such as the attapulgites or the vermiculites, 
usually of a particle size range of from about 0.3 to 1.5 mm. Wettable 
powders, which can be dispersed in water or oil to any desired 
concentration of the active compound, can be prepared by incorporating 
wetting agents into concentrated dust compositions. 
In some cases the active compounds are sufficiently soluble in common 
organic solvents such as kerosene or xylene so that they can be used 
directly as solutions in these solvents. Frequently, solutions of 
herbicides can be dispersed under superatmospheric pressure as aerosols. 
However, preferred liquid herbicidal compositions are emulsifiable 
concentrates, which comprise an active compound according to this 
invention and as the inert carrier, a solvent and an emulsifier. Such 
emulsifiable concentrates can be extended with water and/or oil to any 
desired concentration of active compound for application as sprays to the 
site of the weed infestation. The emulsifiers most commonly used in these 
concentrates are nonionic or mixtures of nonionic with anionic 
surface-active agents. With the use of some emulsifier systems an inverted 
emulsion (water-in-oil) can be prepared for direct application to weed 
infestations. 
A typical herbicidal composition according to this invention is illustrated 
by the following example, in which the quantities are in parts by weight. 
EXAMPLE 15 
Preparation of a Dust 
Product of Example 2--10 
Powdered Talc--90 
The above ingredients are mixed in a mechanical grinder-blender and are 
ground until a homogeneous, free-flowing dust of the desired particle size 
is obtained. This dust is suitable for direct application to the site of 
the weed infestation. 
The compounds of this invention can be applied as herbicides in any manner 
recognized by the art. One method for the control of weeds comprises 
contacting the locus of said weeds with a herbicidal composition 
comprising an inert carrier and as an essential active ingredient, in a 
quantity which is herbicidally toxic to said weeds, a compound of the 
present invention. The concentration of the new compounds of this 
invention in the herbicidal compositions will vary greatly with the type 
of formulation and the purpose of which it is designed, but generally the 
herbicidal compositions will comprise from about 0.05 to about 95 percent 
by weight of the active compounds of this invention. In a preferred 
embodiment of this invention, the herbicidal compositions will comprise 
from about 5 to about 75 percent by weight of the active compound. The 
compositions can also comprise such additional substances as other 
pesticides, such as insecticides, nematocides, fungicides, and the like; 
stabilizers, spreaders, deactivators, adhesives, stickers, fertilizers, 
activators, synergists and the like. 
The compounds of the present invention are also useful when combined with 
other herbicides and/or defoliants, dessicants, growth inhibitors and the 
like in the herbicidal compositions heretobefore described. These other 
materials can comprise from about 5% to about 95% of the active 
ingredients in the herbicidal compositions. Use of combinations of these 
other herbicides and/or defoliants, dessicants, etc. with the compounds of 
the present invention provide herbicidal compositions which are more 
effective in controlling weeds and often provide results unattainable with 
separate compositions of the individual herbicides. The other herbicides, 
defoliants, dessicants and the plant growth inhibitors, with which the 
compounds of this invention can be used in the herbicidal compositions to 
control weeds, can include chlorophenoxy herbicides such as 2,4-D, 
2,4,5-T, MCPA, MCPB, 4(2,4-DB), 2,4-DEB, 4-CPB, 4, CPP, 2,4,5-TB, 
2,4,5-TES, 3,4-DA, silvex and the like; carbamate, herbicides such as IPC, 
CIPC, swep, barban, BCPC, CEPC, CPPC, and the like; thiocarbamate and 
dithiocarbamate herbicides such as DCEC, methan sodium, EPTX, diallate, 
PEBC, perbulate, vernolate and the like; substituted urea herbicides such 
as norea, siduron, dichloral urea, chloroxuron, cycluron, fenuron, 
monuron, monuron TCA, diuron, linuron, monolinuron, neburon, buturon, 
trimeturon and the like; symmetrical triazaine, herbicides such as 
simazine, chlorazine, atraone, desmetryne, norazine, ipazine, prometryn, 
atrazine, trietazine, simetone, prometone, propazine, ametyrne, and the 
like; chloroacetamide herbicides such as 
alpha-chloro-N,N-dimethylacetamide, CDEA, CDAA, 
alpha-chloro-N-isopropylacetamide, 2-chloro-N-isopropylacetanilide, 
4-(chloroacetyl)-morpholine, 1-(chloracetyl) piperidine, and the like; 
chlorinated aliphatic acid herbicides such as TCA, dalapon, 
2,3-dichloropropionic acid, 2,2,3-TPA and the like; chlorinated benzoic 
acid and the phenylacetic acid herbicides such as 2,3,6-TBA, 2,3,5,6-TBA, 
dicamba, tricamba, amiben, fenac, PBA, 2-methoxy-3,6-dichlorophenylacetic 
acid, 3-methoxy-2,6-dichlorophenylacetic acid, 
2-methoxy-3,4,6-trichlorophenylacetic acid, 2,4-dichloro-3-nitrobenzoic 
acid and the like; and such compounds as aminotriazole, maleic hydrazide, 
phenyl mercuric acetate, endothal, biuret, technical chlordane, dimethyl 
2,3,5,6-tetrachloroterephthalate, diquat, erbon, DNC, DNBP, dichlorobenil, 
DPA, diphenamid, dipropalin, trifluraline, solan, dicryl, merphos, DMPA, 
DSMA, MSMA, potassium azide, acrolein, benefin, bensulide, AMS, bromacil, 
2-(3,4-dichlorophenyl)-4-methyl-1,2,4-oxadiazolidine, 3,5-dione, 
bromoxynil, cacodylic acid, DMA, DPMF, cypromid, DCB, DCPA, dichlone, 
diphenatril, DMTT, DNAP, EBEP, EXD, HCA, ioxynil, IPX, isocyil, potassium 
cyanate, MAA, MAMA, MCPES, MCPP, MH, molinate, NPA, OCH, paraquat, PCP, 
picloram, DPA, PCA, pyrichlor, sesone, terbacil, terbutol, TCBA, brominil, 
CP-50144, H-176-1, H-732, M-2091, planavin, sodium tetraborate, calcium 
cyanamid, DEF, ethyl xanthogen disulfide, sindone, sindeone B, propanil 
and the like. 
Such herbicides can also be used in the methods and composition of this 
invention in the form of their salts, esters, amides, and other 
derivatives whenever applicable to the particular parent compounds. 
Weeds are undesirable plants growing where they are not wanted, having no 
economic value, and interfering with the production of cultivated crops, 
with the growing of ornamental plants, or with the welfare of livestock. 
Many types of weeds are known, including annuals such as pigweed, 
lambsquarter, foxtail, crabgrass, wild mustard, field pennycress, 
ryegrass, goose grass, chickweed, wild oats, velvet leaf, purselane, 
barnyard grass, smartweed, knotweed, cocklebur, wild buckwheat, kochia, 
medic corn cockle, ragweed, sowthistle, coffee-weed, croton, cuphea, 
dodder, fumitory, groundsel, hemp nettle, knowel, spurge, spurry, emex, 
jungle rice, pondweed, dog fennel, carpetweed, morning glory, bedstraw, 
ducksalad and naiad; biennials such as wild carrot, matricaria, wild 
barley, campion, chamomile, burdock, mullein, roundleaved mallow, bull 
thistle, hounds-tongue, moth mullein and purple star thistle; or 
perennials such as white cockle, perennial rye-grass, quackgrass, Johnson 
grass, Canada thistle, hedge bindweed, Bermuda grass, sheep sorrel, curly 
dock, nutgrass, field chickweed, dandelion, campanula, field bindweed, 
Russian knapweed, mesquite, toadflax, yarrow, aster, gromwell, horsetail, 
ironweed, sesbania, bulrush, cattail and wintercress. 
Similarly, such weeds can be classified as broadleaf or grassy weeds. It is 
economically desirable to control the growth of wuch weeds without 
damaging beneficial plants or livestock. 
The new compounds of this invention are particularly valuable for weed 
control because they are toxic to many species and groups of weeds while 
they are relatively nontoxic to many beneficial plants. The exact amount 
of compound required will depend on a variety of factors, including the 
hardiness of the particular weed species, weather, type of soil, method of 
application, the kind of beneficial plants in the same area, and the like. 
Thus, while the application of up to only about one or two ounces of 
active compound per acre may be sufficient for good control of a light 
infestation of weeds growing under adverse conditions, the application of 
ten pounds or more of active compound per acre may be required for good 
control of a dense infestation of hardy perennial weeds growing under 
favorable conditions. 
The herbicidal toxicity of the new compounds of this invention can be 
illustrated by many of the established testing techniques known to the 
art, such as pre- and post-emergence testing. 
The herbicidal activity of the compounds of this invention was demonstrated 
by experiments carried out for the pre-emergence control of a variety of 
weeds. In these experiments small plastic greenhouse pots filled with dry 
soil were seeded with the various weed seeds. Twenty-four hours or less 
after the seeding, the pots were sprayed with water until the soil was wet 
and the test compounds formulated as aqueous emulsions of acetone 
solutions containing emulsifiers were sprayed at the indicated 
concentrations on the surface of the soil. 
After spraying, the soil containers were placed in the greenhouse and 
provided with supplementary heat as required and daily or more frequent 
watering. The plants were maintained under these conditions for a period 
of 21 days and the condition of the plants and the degree of injury to the 
plants after 14 and again after 21 days was rated on a scale of from 0 to 
10, as follows: 0=no injury, 1, 2=slight injury, 3, 4=moderate injury, 5, 
6=moderately severe injury, 7, 8, 9=severe injury, 10=death and NE 
indicated not emerged. The effectiveness of these compounds is 
demonstrated by the following data: 
______________________________________ 
PRE-EMERGENCE HERBICIDE ACTIVITY 
14 DAYS AFTER TREATMENT 
PRODUCT OF EXAMPLE 2 
TEST RATE 
(Lbs/Acre) 0.5 0.25 0.125 
0.062 
______________________________________ 
Wild 0 0 0 0 
Mustard 
Bindweed 6 6 0 0 
Pigweed 0 0 0 0 
Jimsonweed 0 0 5 0 
Velvet NE NE 0 NE 
Leaf 
Morning 6 6 6 4 
Glory 
Yellow 2 1 0 0 
Foxtail 
Barnyard NE NE 6 0 
Grass 
Johnson 4 4 2 0 
Grass 
Quack Grass 4 2 0 0 
Wild Oats 6 5 3 0 
Crabgrass NE NE 9 3 
Sprangletop 9 NE 0 0 
Cheat Grass 5 2 0 0 
Sugar Beets 0 0 0 0 
Soybean 4 0 0 0 
Cotton 0 0 0 0 
Pinto Bean 3 0 0 0 
Alfalfa 0 0 4 0 
Wheat 8 6 4 0 
Rice 6 6 5 5 
Sorghum 7 7 5 3 
Corn 5 4 3 NE 
Oat 5 5 2 0 
______________________________________ 
______________________________________ 
PRE-EMERGENCE HERBICIDE ACTIVITY 
21 DAYS AFTER TREATMENT 
PRODUCT OF EXAMPLE 2 
TEST RATE 
(Lbs/Acre) 0.5 0.25 0.125 0.062 
______________________________________ 
Wild 0 0 0 0 
Mustard 
Bindweed 8 4 3 0 
Pigweed 0 0 0 0 
Jimsonweed 0 3 0 0 
Velvet NE NE 0 NE 
Leaf 
Morning 7 7 7 2 
Glory 
Yellow 4 3 0 0 
Foxtail 
Barnyard NE NE 7 1 
Grass 
Johnson 6 5 3 0 
Grass 
Quack Grass 6 2 0 0 
Wild Oats 5 4 2 0 
Crabgrass NE NE 6 0 
Sprangletop 7 NE 0 0 
Cheat Grass 4 0 0 0 
Sugar Beets 3 0 0 0 
Soybeans 7 4 3 4 
Cotton 3 4 3 3 
Pinto Bean 3 3 3 3 
Alfalfa 0 0 0 0 
Wheat 10 5 3 0 
Rice 6 4 3 3 
Sorghum 8 7 3 0 
Corn 6 3 0 NE 
Oat 3 3 1 0 
______________________________________ 
The herbicidal activity of the compounds of this invention was also 
demonstrated by experiments carried out for the post-emergence control of 
a variety of weeds. In these experiments the compounds to be tested were 
formulated as aqueous emulsions and sprayed at the indicated dosage on the 
foliage of the various weeds species that have attained a prescribed size. 
After spraying, the plants were placed in a greenhouse and watered daily 
or more frequently. Water was not applied to the foliage of the treated 
plants. The severity of the injury was determined 14 days after treatment 
and was rated on the scale of from 0 to 10 heretobefore described. The 
effectiveness of these compounds is demonstrated by the following data: 
______________________________________ 
POST-EMERGENCE HERBICIDAL ACTIVITY 
14 DAYS AFTER TREATMENT 
PRODUCT OF EXAMPLE 2 
TEST RATE 
(Lbs/Acre) 8 
______________________________________ 
Wild Mustard 
0 
Bindweed 3 
Morning Glory 
5 
Jimson Weed 
0 
Pigweed 0 
Soybeans 0 
Wild Oats 8 
Barnyard grass 
9 
Crabgrass 7 
Yellow Foxtail 
7 
Johnson Grass 
9 
Yellow Nutsedge 
4 
______________________________________