Disclosed are compounds such as 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitroacetophenone oxime-O-methyl ether, and the method of controlling weeds, such as wild oats with the compounds.

BACKGROUND OF THE INVENTION 
1. Field of the Invention 
The invention pertains to 5-(4-trifluoromethyl, or 
(2-chloro-4-trifluoromethyl) or 
(2,6-dichloro-4-trifluoromethylphenoxy-2-nitro substituted carbonyl 
oxime-O-alkyl ethers, such as 
5-(2-chloro-4-trifluoromethylphenoxy)-2-nitro-acetaphenone oxime-O-methyl 
ether and their use to control weeds, i.e., wild oats. 
2. Description of the Prior Art 
The prior art describes diphenyl ethers in general. The prior art, however, 
is silent concerning the novel compounds of this invention and their use 
as preemergence herbicides against certain weeds and postemergence 
herbicides against weeds. 
SUMMARY OF THE INVENTION 
The invention concerns novel herbicidal compounds graphically represented 
by general Formula I 
##STR1## 
wherein: Y is chlorine or hydrogen; Z is chlorine when Y is chlorine, or Z 
is hydrogen when Y is chlorine or hydrogen; R is hydrogen or an alkyl of 
up to three carbon atoms, and R.sup.1 is an alkyl of up to four carbon 
atoms; as well as the method of preparing these novel compounds and the 
control of weeds with the compounds; for example 
5-(2-chloro-4-trifluorophenoxy)-2-nitroacetophenone oxime-O-methyl ether 
in its anti and syn isomer forms is useful for controlling the weeds 
described herein. 
DETAILED DESCRIPTION OF THE INVENTION 
The novel agriculturally useful 5(2-chloro-4-trifluoromethyl- or 
4-trifluoromethyl or 
2,6-dichloro-4-trifluoromethylphenoxy)-2-nitro-substituted carbonyl oxime 
alkyl ethers in both their anti and syn forms are graphically represented 
by general Formula I wherein: 
##STR2## 
Y is chlorine or hydrogen; Z is chlorine when Y is chlorine, or Z is 
hydrogen when Y is chlorine or hydrogen; 
R is hydrogen or an alkyl of up to three carbon atoms, and 
R.sup.1 is an alkyl of up to four carbon atoms. 
Representative compounds are those in which 
I. R is an alkyl of up to three carbon atoms; such as 
5-(4-trifluoromethylphenoxy)-2-nitrobutyrophenone oxime-O-t-butyl ether, 
5-(2-chloro-4-trifluoromethylphenoxy)-2-nitro-2-methylpropiophenone 
oxime-O-sec butyl ether, 
5-(2,6-dichloro-4-trifluoronethylphenoxy)-2-nitro butyrophenone 
oxime-O-isopropyl ether, 
5-(4-trifluoromethylphenoxy)-2-nitropropiophenone oxime-O-propyl ether, 
5-(2-chloro-4-trifluoromethylphenoxy)-2-nitropropiophenone oxime-O-methyl 
ether, 
5-(2-chloro-4-trifluoromethylphenoxy)-2-nitroacetophenone oxime-O-ethyl 
ether, 
5-(2-chloro-4-trifluoromethylphenoxy)-2-nitroacetophenone oxime-O-isobutyl 
ether, 
5-(2,6-dichloro-4-trifluoromethylphenoxy)-2-nitroacetophenone 
oxime-O-propyl ether, 
II. R is hydrogen; such as: 
5-(4-trifluoromethylphenoxy)-2-nitrobenzaldoxime-O-t-butyl ether, 
5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzaldoxime-O-methyl ether, 
5-(2,6-dichloro-4-trifluoromethylphenoxy)-2-nitrobenzaldoxime-O-ethyl 
ether, 
5-(4-trifluoromethylphenoxy)-2-nitrobenzaldoxime-O-propyl ether. 
As used herein and in the claims, the word "compound" and the name of 
compound, for example 5-(2-chloro-4-trifluorophenoxy)-2-nitroacetophenone 
oxime-O-methyl ether, refers to the two isomers of the compound, the syn 
and anti isomers. 
Although all the compounds as disclosed herein are useful for the purposes 
disclosed herein, some compounds are preferred over others. Those 
compounds in which R is methyl are preferred to those compounds in which R 
is hydrogen or an alkyl of from two to three carbon atoms. Those compounds 
in which Y and Z are as mentioned herein, in order of increasing 
preference are; those in which Y and Z are hydrogen, those in which Y and 
Z are chlorine, and those in which Y is chlorine and Z is hydrogen. Those 
compounds in which R.sup.1 is methyl or ethyl are greatly preferred. 
The highly preferred compounds graphically represented by general Formula I 
are: 
5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzaldoxime-O-methyl ether, 
5-(2-chloro-4-trifluoromethylphenoxy)-2-nitro benzaldoxime-O-ethyl ether, 
5-(2-chloro-4-trifluoromethylphenoxy)-2-nitroacetophenone oxime-O-ethyl 
ether, and 
5-(2-chloro-4-trifluoromethylphenoxy)-2-nitroacetophenone oxime-O-methyl 
ether. 
The most preferred compound is 
5-(2-chloro-4-trifluoromethylphenoxy)-2-nitroacetophenone oxime-O-methyl 
ether. 
SYNTHESIS 
a. GENERAL PROCEDURE 
The synthesis of the 5-(substituted-phenoxy)-2-nitro substituted carbonyl 
oxime ethers, described herein proceeds according to the reaction 
equations (1), (2), (3) and (4) shown below: 
The appropriate trifluoromethyl halo substituted compound of Formula V 
where Y and Z are as described herein is reacted with a salt of a 
metal-3-substituted carboxyl phenoxide of Formula VI, where M is a cation 
of sodium, (Na+), potassium (K+) to form a compound of Formula VII, which 
is separated from the reaction mixture and nitrated to a compound of 
Formula II. Note the step of nitrating also includes the step of 
separating the compound of Formula VI from the nitrating reaction mixture. 
##STR3## 
The appropriate carbonyl compound (aldehyde) graphically represented by 
general Formula II wherein Y and Z, are as defined herein and R is 
hydrogen; for example (0.001 mole) is dissolved in 20 milliliters of 
tetrahydrofuran (THF) and 12 milliliters of absolute ethanol. To this 
stirred solution is added hydroxylamine hydrochloride (0.012 mole) in 1 
milliliter of water, and then 0.6 grams (0.015 mole) sodium hydroxide in 5 
milliliters of water. The solution is stirred overnight at ambient 
temperature and the THF and ethanol is stripped off in vacuo, leaving a 
two-phase system. The oil phase is dissolved in chloroform (HCCl.sub.3) 
and then separated from the aqueous phase. The chloroform layer is then 
extracted with water, and with a saturated sodium chloride solution, and 
then dried over anhydrous magnesium sulfate (MgSO.sub.4). Filtration and 
evaporation affords the crude product of 5-(2-chloro-4-trifluoromethyl-, 
or 4-trifluoromethyl- or 2,6-dichloro-4-trifluoromethylphenoxy)-2-nitro 
substituted carbonyl oximes of general Formula III wherein Y, Z, and R are 
as defined herein. The crude product can be recrystallized in carbon 
tetrachloride (CCl.sub.4). 
An alternate procedure is used when R of Formula II is an alkyl described 
herein. This procedure employs anhydrous conditions. For example, (0.0056 
mol) of the appropriate carbonyl compound of general Formula II, wherein Y 
and Z are as defined herein and R is an alkyl defined herein, is dissolved 
in 20 ml. of a 1:1 mixture of absolute ethanol and dry benzene. To this 
solution is added 0.77 grams of hydroxylamine hydrochloride in 15 ml. of 
absolute ethanol and (0.0112 mol) of a tertiary amine, such as 
triethylamine, which is preferred. The solution is heated to reflux and 
the water formed in the reaction is azeotroped off. After refluxing for 18 
hours, solvent is removed in vacuo, the residue dissolved in chloroform 
and extracted with water and saturated sodium chloride solution and dried 
over anhydrous magnesium sulfate. Filtration and evaporation affords the 
crude product oximes of general Formula III. 
The appropriate oxime of general Formula III, prepared as above, (0.004 
mole) is dissolved in four milliliters of ethanol and added to a solution 
of 0.1 gram (0.0045 mole) of the appropriate halo-alkyl compound of 
general Formula IV wherein R.sup.1 is as defined herein, and A is 
chlorine, bromine, or iodine, and the reaction is followed by thin layer 
chromatography. The solution can be heated at reflux, if the reaction is 
sluggish. The product of general Formula I is obtained either by 
filtration or by evaporating the solvent, dissolving the residue in 
chloroform, extracting with water, drying and then evaporating the 
chloroform solvent. 
Sodium hydride can be used in place of the sodium alkoxide, and the solvent 
can be an ether such as THF or diethyl ether, etc.

b. EXAMPLES 
The following example illustrates the synthesis of the compound of general 
Formula I by the general procedure described above. 
EXAMPLE I 
Synthesis of 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitroacetophenone 
oxime-O-methyl ether 
a. Preparation of 3-(2-chloro-4-trifluoromethylphenoxy)acetophenone. 
To a 250 ml. flask containing a solution of 13.92 grams of the potassium 
salt of 3-hydroxyacetophenone in 30 ml. of dry dimethylsulfoxide (DMSO), 
was added 17.12 grams (0.08 mole) of 3,4-dichlorobenzotrifluoride. The 
reaction solution was heated to 175.degree. Centigrade for six hours, and 
then cooled and stirred at ambient temperature for 18 hours. The bulk of 
the DMSO was removed by evaporation, and the remaining dark residue was 
stirred with diethyl ether for 15 minutes and filtered. The filtrate was 
extracted once with wter, once with sodium hydroxide, once with a 
saturated sodium chloride solution, dried over anhydrous MgSO.sub.4, 
filtered, decolorized with charcoal, and evaporated to dryness leaving 
16.04 grams of a dark red oil of 
3-(2-chloro-4-trifluoromethylphenoxy)acetophenone. The material was 
further purified by passing through a neutral, grade III alumina column. 
b. Nitration of 3-(2-chloro-4-trifluoromethylphenoxy)acetophenone 
To a 100 milliliter (ml.) flask containing a solution of 26 ml. of 
concentrated sulfuric acid (H.sub.2 SO.sub.4), and 16 ml. of 
ethylenedichloride (EDC), which was cooled to zero (0.degree.) degrees 
Centigrade, 6.28 grams, (0.02 mole) of the dark red oil of 
3-(2-chloro-4-trifluoromethylphenoxy)acetophenone (prepared as described 
herein) was added dropwise to form a brownish-black solution. When the 
addition of 3-(2-chloro-4-trifluoromethylphenoxy)acetophenone was 
completed, dry potassium nitrate (KNO.sub.3), (2.0 grams, 0.020 mole) was 
added in small portions over a 20 minute period so as to maintain the 
reaction mixture below 4.degree. Centigrade. The reaction mixture was 
stirred for 0.5 hours at 0.degree. Centigrade. It was then poured into 250 
ml. of ice and water, and the resulting mixture was mixed with 200 ml. of 
chloroform, (CHCl.sub.3). The organic layer was separated, and then 
extracted twice with water, once with a saturated sodium chloride 
solution, and then dried over anhydrous magnesium sulfate, and then 
filtered. The organic solvent was evaporated off to yield 6.51 grams of an 
orange oil which analysis showed was a mixture of two positional isomers, 
one of which was 
5-(2-chloro-4-trifluoromethylphenoxy)-2-nitroacetophenone. The mixture was 
separated into two fractions by high pressure liquid chromatography (HPLC) 
using diethyl ether as the eluant. 
The diethylether was stripped from fraction #1, leaving 2.37 grams of an 
orange oil of 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitroacetophenone. 
Nuclear magnetic resonance [(NMR) (CDCl.sub.3)]: 2.47.delta. (sing., 3H), 
6.78-8.21.delta. (mult. 6H); Infra Red (IR): 1710, 1575, 1520, 1400, 1315 
cm.sup.-1 ; Mass Spectra (MS) molecular ion at m/e 359. 
c. Synthesis of 
5-(2-chloro-4-trifluoromethylphenoxy)-2-nitroacetophenoneoxime 
A 100 ml. flask was charged with a solution of 2.0 grams (0.0056 mole) of 
the orange oil, 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitroacetophenone, 
in 10 ml. of absolute ethanol and 10 ml. of dry benzene. A solution of 
hydroxylamine hydrochloride (0.77 grams, 0.011 mole) in 15 ml. of absolute 
ethanol was added followed by addition of 1.12 grams (0.011 mole) of an 
acid acceptor triethylamine. The reaction mixture was then refluxed; when 
20 ml. of solvent was distilled off, an additional 15 ml. of benzene was 
added. Refluxing was continued until 15 ml. of solvent distilled off, and 
then the remaining solution was refluxed for 16 hours, with the formation 
of a mixture of the syn and anti isomers of 
5-(2-chloro-4-trifluoromethylphenoxy)-2-nitroacetophenone oxime. The 
solvent was stripped from the mixture, and the residue was dissolved in 
chloroform. The chloroform solution was extracted twice with water, then 
with a saturated solution of sodium chloride, and then dried over 
anhydrous magnesium sulfate. 
The chloroform solution was filtered and the solvent (chloroform) was 
evaporated to yield 2.03 grams of an orange oil of 
5-(2-chloro-4-trifluoromethylpehnoxy)-2-nitroacetophenone oxime (anti and 
syn), which had the following: 
Mass spectra (MS): molecular ion at m/e 374. 
Syn and Anti NMR (CDCl.sub.3): 2:138.delta. (sing., 3H), 6.91-8.178.delta. 
(mult., 6-H), 9.338.delta. (sing., 1H). 
Syn and Anti IR: 3100 broad, 1605, 1575, 1520, 1400 cm.sup.-1. 
d. Formation of the anti and syn Isomers of 
5-(2-chloro-4-trifluoromethylphenoxy)-2-nitro acetophenone oxime-O-methyl 
ether 
A solution of 0.10 grams (0.0045 ml.) of sodium metal in 5 ml. of methanol 
under nitrogen was charged into a 25 ml. flask. When all of the sodium had 
reacted, 1.50 grams (0.004 mole) of the 
5-(2-chloro-4-trifluoromethylphenoxy)-2-nitroacetophenone oxime (anti and 
syn) prepared as described, and dissolved in 3 ml. of methanol was added, 
and the solution stirred. Methyliodide (0.64 grams, 0.0045 mole) was added 
next to the solution; and the resulting mixture was stirred at ambient 
temperature under nitrogen for forty-two (42) hours. The solvent was 
stripped from the solution and the residue was dissolved in methylene 
chloride (CH.sub.2 Cl.sub.2). The CH.sub.2 Cl.sub.2 solution was extracted 
twice with water and once with a saturated sodium chloride solution, and 
then dried over anhydrous magnesium sulfate. The CH.sub.2 Cl.sub.2 
solution was then filtered and the solvent removed by evaporation to yield 
1.84 grams of an orange oil containing the anti and syn isomers of 
5-(2-chloro-4-trifluoromethylphenoxy)- 2-nitro acetophenone oxime-O-methyl 
ether. The orange oil was purified by chromatography by dissolving it into 
5 ml. of ethyl ether and placing it on top of an eight inch by 21 mm. 
column of grade III alumina. The column was eluted with diethyl ether and 
the desired fractions were collected. The solvent was removed to yield 
0.49 grams of a yellow oil of anti and syn isomers of 
5-(2-chloro-4-trifluoromethylphenoxy)-2-nitro-0-acetophenone oxime. 
MS: Molecular ion at m/e. 388. 
Syn and Anti IR: 2965, 1605, 1570, 1520, 1400 cm.sup.-1. 
Syn and Anti NMR (CDCl.sub.3): 2.31.delta. and 2.25.delta. (sing., 3H), 
3.69.delta. and 3.91 (sing., 3H), 6.85-8.19.delta. (mult.6H). 
APPLICATIONS OF THE COMPOSITIONS AGAINST WEEDS 
The novel compounds of this invention are particularly valuable for 
preemergence and postemergence weed control because they are toxic to many 
species and groups of weeds and are relatively nontoxic to many beneficial 
plants. The exact amount of one or more of the compounds described herein 
required depends upon a variety of factors, including the hardiness of the 
particular weed species, the weather, the type of soil, the method of 
application, the kind of beneficial plants in the same area, and the like. 
Thus, while the application of up to only about 0.1 pounds of active 
compound per acre may be sufficient for good control of a light 
infestation of weeds growing under adverse conditions, the application of 
2 pounds or more of an active compound per acre may be required for good 
control of a dense infestation of hardy perennial weeds growing under 
favorable conditions. The preferred compounds mentioned herein are 
generally used at the lower application rates such as from 0.1 to 10 
pounds per acre; the less preferred but generally useful compounds are 
generally applied at the higher applications of from 10 to 20 pounds per 
acre, and those compounds which are intermediate between the most 
preferred compounds and the generally useful compounds are generally 
applied at rates from 5 to 15 pounds per acre. 
a. Examples of Weeds Which May Be Controlled By The Compounds Described 
Herein 
Weeds are undesirable plants growing where they are not wanted and may be 
classified as broadleaf or grassy weeds, a classification which includes 
many types of known weeds. It is believed that many weeds may be 
controlled by the compositions set forth herein, when applied in a 
herbicidally effective amount. These include field pennycress, ryegrass, 
goosegrass, chickweed, purslane, smartweed, knotweed, wild buckwheat, 
kochia, medic, corn cockle, ragweed, sow-thistle, croton, cuphea, dodder, 
fumitory, groundsel, hempnettle, knawel, spurge, spurry, emex, jungle 
rice, pondweed, dogfennel, carpetweed, bedstraw, ducksalad, naiad, 
cheatgrass, fall panicum, witchgrass, switchgrass, watergrass, teaweed, 
wild turnip, and sprangletop; biennials such as wild carrot, matricaria, 
wild barley, campion, chamomile, burdock, mullein, roundleaved mallow, 
bull thistle, houndstongue, moth mullein, and purple star thistle; or 
perennials such as white cockle, perennial ryegrass, quackgrass, 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, cat-tail, wintercress, horsenettle, nutsedge, 
milkweed, and sicklepod. 
The genus of weeds the compounds, particularly the most preferred 
compounds, appear most active against preemergence are: Sorghum, Sesbania, 
Fatua and Echinochola. 
Weed species against which the compounds of the invention appear to be most 
effective (preemergence) are: Sorghum halepense (johnsongrass), Sesbania 
spp. (coffeeweed), Avena fatus (L) (wild oats), and Echinochola crusgalli 
(L) (barnyard grass). 
The genus of weeds that the compounds, particularly the most preferred 
compounds, appear most active against postemergence are: Sida, Datura, 
Brassica, Setaria, Gossypium, Sorghum, Sesbania, Abutilon, Ipomoea, Avena, 
and Echinochola. 
The compositions, particularly, the most preferred compositions, appear to 
be most effective when applied postemergence against the weed species Sida 
spinosa (L) (teaweed, prickly sida), Datura stramonium (L) (jimsonweed), 
Brassica kaber (DC) (wild mustard), Setaria glauca (L) (yellow foxtail), 
Gossypium hirsutum (L) (cotton), Sesbania spp. (coffeeweed), Abutilon 
theophrasti (L) (velvetleaf), Ipomoea purpurea (L) Roth (tall 
morningglory), Sorghum halepense (johnsongrass), Avena fatua (L) (wild 
oats) and Echinochola crusgalli (L) (barnyard grass). 
b. Description of the Method of Controlling Weeds 
As used herein and in the claims, the method of controlling the weeds 
comprises contacting the weeds with a herbicidally effective amount of a 
composition represented by the general formula described herein. The term 
"contacting the weeds" refers to any method of contacting the weeds, both 
preemergence (before the weeds appear) and/or postemergence (after the 
weeds appear), such as applying granules of the compound to the soil prior 
to emergence, or spraying a solution of the compound or compounds 
described by the general formula, or any other method known in the art by 
which the weeds are contacted either before they emerge or after they 
emerge, or both before and after they emerge, but preferably after they 
emerge, with one or more of the compounds represented by Formula I 
described herein. The phrase "the herbicidally effective amount" refers to 
that amount required under the environmental conditions in order to 
effectively control, that is, by which the weeds are killed or are injured 
so severely as not to be able to recover from the application of the 
compound. 
c. GENERAL APPLICATION OF THE COMPOUNDS 
For practical use as herbicides, the compounds of this invention are 
generally incorporated into herbicidal formulations which comprise an 
inert carrier and a herbicidally toxic amount of a compound mentioned 
herein. Such herbicidal formulations enable the active compound to be 
applied conveniently to the side of the weed infestation in any desired 
quantity. These formulations 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 millimeters. 
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 formulations 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 conentration 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 formulation according to this invention is illustrated 
by the following example, in which the quantities are in parts by weight. 
EXAMPLE III 
Preparation of a Dust 
Product of Example I: 10 
Powdered Talc: 90 
The above ingredients are mixed in a mechanical grinder-blender and are 
ground until a homogeneous, freeflowing dust of the desired particle size 
is obtained. This dust is suitable for direct application to the site of 
the weed infestation. 
d. Use of Compounds Alone Or In Mixtures 
Although all of the compounds described herein and represented by the 
general formula described herein are useful as herbicides, some of these 
are preferred and are better for applications against weeds. In general, 
all of the compounds described herein may be used either alone or together 
in mixtures of the compounds described herein. When used in mixtures the 
amount of ratio of one compound to another may vary from 0.01 to 100. The 
amount to use ranges from 0.10 pounds per acre to 20 pounds per acre 
depending upon the conditions. 
e. Manner of Application Of The Compounds Of This Invention In Formulations 
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 formulation comprised 
of an inert carrier and one or more of the compounds of this invention as 
an essential active ingredient, in a quantity which is herbicidally toxic 
to said weeds. The concentration of the new compounds of this invention in 
the herbicidal formulations will vary greatly with the type of formulation 
and the purpose for which it is designed, but generally the herbicidal 
formulations 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 formulations will comprise from about 5 to 
75 percent by weight of the active compound. The formulations can also 
comprise 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, desiccants, growth inhibitors, and the 
like in the herbicidal formulations heretofore described. These other 
materials can comprise from about 5 percent to about 95 percent of the 
active ingredients in the herbicidal compositions. Use of combinations of 
the present invention provide herbicidal formulations which are more 
effective in controlling weeds and often provide results unattainable with 
separate formulations of the individual herbicides. 
f. Examples of Other Pesticides And Herbicides For Combinations 
The other herbicides, defoliants, desiccants, and plant growth inhibitors, 
with which the compounds of this invention can be used in the herbicidal 
formulations to control weeds, can include: chlorophenoxy herbicides; such 
as 2,4-D, 2,4,5-T, MCPA, NCPB, 4-2,4-DB, 2,4-DEB, 4-CPB, 4-CPA, 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 CDEC, metam sodium, 
EPTC, diallate, PEBC, perbulate, vernolate and the like; substituted urea 
herbicides such as norea, siduron, dichloroal urea, chloroxuron, cycluron, 
fenuron, monuron, monuron TCA, diuron, linuron, monolinuron, neburon, 
buturon, trimeturon, and the like; symmetrical triazine herbicides such as 
simazine, chlorazine, desmetryne, norazine, ipazine, prometryn, atrazine, 
trietazine, simetone, prometone, propazine, ametryne, 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-(chloroacetyl) 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 phenylacetic acid herbicides 
such as 2,3,6-TBA, 2,3,5,6TBA, dicamba, tricamba, amiben, fenac, PBA, 
2-methoxy-3,5-dichlorophenylacetic acid, 3-methoxy-2, 
6-dichlorophenylacetic acid, 2-methoxy-3,5,6-trichlorophenylacetic acid, 
2,5-dichloro-3-nitrobenzoic acid, dual metribuzin and the like; and such 
compounds as aminotriazole, maleic hydrazide, phenyl mercuric acetate, 
endothall, biuret, technical chlordane, dimethyl 
2,3,5,6-tetrachloroterephthalate, diquat, erbon, DNC, DNBP, dichlobenil, 
DPA, diphenamid, dipropalin, trifluralin, solan, dicryl, merphos, DMPA, 
DSMA, MSMA, potassium azide, acrolein, benefin, bensulfide, AMS, bromacil, 
2-(3,4-dichlorophenyl)-4methyl-1,2,4-oxadiazolidine-3,5-dione, bromoxynil, 
cacodylic acid, CMA, CPMF, cypromid, DCB, DCPA, dichlone, dipheratril, 
DMTT, DNAP, EXD, ioxynil, isocil, potassium cyanate, MAA, MAMA, MCPES, 
MCPP, MH, molinate, NPA, paraquat, PCP, picloram, DPA, PCA, pyrichlor, 
sesone, terbacil, terbutol, TCBA, LASS0, planavin, sodium tetraborate, 
calcium cyanamide, DEF, ethyl xanthogen disulfide, sindone, sindone B, 
propanil, and the like. Such herbicides can also be used with the 
compositions of this invention in the form of their salts, esters, amides, 
and other derivatives whenever applicable to the particular parent 
compounds. 
g. Examples of Herbicidal Control 
The following examples illustrate the utility of the compositions described 
herein for the control of weeds. 
These tests described herein were conducted in a laboratory under 
laboratory conditions in accordance with standard herbicidal testing 
procedures for preemergence and postemergence control. The plants are 
observed for 21 days after treatment, and the observations were recorded. 
EXAMPLE II 
When 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitroacetophenone 
oxime-0-methyl ether (from Example I) was applied preemergence at ten (10) 
pounds per acre to Sorghum halepense (L) (johnsongrass--from seed); 
Sesbania spp. (coffeeweed), Avena fatua (L) (wild oats), and Echinochola 
crusgalli (L) (barnyard grass), the weeds were killed by 21 days. 
EXAMPLE III 
When 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitroacetophenone 
oxime-0-methyl ether (from Example I) was applied postemergence at ten 
(10) pounds per acre to: Sida spinosa (L) (teaweed, also called prickly 
sida); Datura stramonium (jimsonweed), Brassica kaber (wild mustard), 
Setaria glauca (L) (yellow foxtail), Gossypium hirsutum (cotton), Sesbania 
spp. (coffeeweed), Abutilon theophrasti (velvetleaf), Ipomoea purpurea (L) 
Roth (tall morningglory), Sorghum halephense (johnsongrass), Avena fatua 
(L) (wild oats), and Echinochola crusgalli (L) (barnyard grass), all the 
weeds were killed by 21 days. 
While the invention has been described with reference to specific details 
of certain illustrative embodiments, it is not intended that it shall be 
limited thereby except insofar as such details appear in the accompanying 
claims.