METHODS FOR CONTROLLING WEEDS USING FORMULATIONS
CONTAINING FLUTHIACET-METHYL AND HPPD HERBICIDES
FIELD OF THE DISCLOSED SUBJECT MATTER
[0001] The presently disclosed subject matter relates to compositions containing
fluthiacet-methyl and p-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors, and methods
for controlling weeds using those compositions.
BACKGROUND
[0002] One of the more preferred methods of controlling weeds in crops involves the
post-emergent control of weeds wherein herbicide(s) are applied after the crop in question
has emerged from the soil. Post-emergent control is desirable as it requires the application of
herbicide only where an infestation of weeds is present. In contrast, pre-emergent control
requires the application of herbicide early in the growing season before most weeds have
germinated, with the result that such chemicals must be employed throughout a field even if
they would ultimately not be needed.
[0003] Fluthiacet-methyl, or methyl [[2-chloro-4-fluoro-5-[(tetrahydro-3-oxo-lH,3H-
[l,3,4]thiadiazolo[3,4-a]pyridazin-l-ylidene)amino]phenyl]thio]acetate, is an effective post-
emergent herbicide for a number of weeds, particularly broadleaf weeds.
[0004] p-Hydroxyphenylpyruvate dioxygenase (HPPD) is an enzyme found in both
plants and animals, which catalyzes the catabolism of the amino acids phenylalanine and
tyrosine. Inhibition of this enzyme has profound effects on plants, affecting the formation of
homogentisic acid which is a key precursor for the biosynthesis of both tocopherols (vitamin
E) and plastoquinone, a critical co-factor in the formation of carotenoids, which protect
chlorophyll in plants from being destroyed by sunlight.

SUMMARY OF THE DISCLOSED SUBJECT MATTER
[0005] It has now been discovered that fluthiacet-methyl, when used in combination
with a para-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitor, is surprisingly effective
at controlling broadleaf weeds having an average height ranging from about 4 inches to about
8 inches.
[0006] The purpose and advantages of the disclosed subject matter will be set forth in
and apparent from the description that follows, as well as will be learned by practice of the
disclosed subject matter. Additional advantages of the disclosed subject matter will be
realized and attained by the methods and systems particularly pointed out in the written
description and claims hereof.
[0007] In one embodiment, the present disclosure describes an agricultural
formulation or tank mix containing at least two agriculturally active ingredients: fluthiacet-
methyl and an HPPD inhibitor. In an embodiment, the HPPD inhibitor is selected from
mesotrione, sulcotrione, nitisinine, tembotrione, topramezone, fenquinotrione, ketospiradox,
and tefuryltrione. In another embodiment, the HPPD inhibitor is preferably mesotrione.
According to one aspect of this embodiment, the fluthiacet-methyl and the HPPD inhibitor
are present in a ratio between about 1:2 and about 1:60 by weight. In a preferred aspect, the
fluthiacet-methyl and the HPPD inhibitor are present in a ratio between about 1:10 and about
1:40. In a more preferred aspect, the fluthiacet-methyl and the HPPD inhibitor are present in
a ratio between about 1:15 and about 1:35. These can be commercial formulations that are
tank mixed at the time of application or more preferably a suspension concentrate premix
formulation. In a further aspect, the agricultural formulation or tank mix contains an
additional crop protection agent. The additional crop protection agent can be selected from
the group consisting of atrazine, glyphosate, glufosinate, pyroxasulfone, dicamba,

diflufenzopyr, nicosulfuron, salts thereof, and mixtures of two or more thereof. In one aspect
the additional crop protection agent is atrazine.
[0008] In another embodiment, the present disclosure presents a method for
controlling weeds having an average height ranging from about 4 inches to about 8 inches in
a crop, wherein the method includes the step of applying to weeds having an average height
ranging from about 4 inches to about 8 inches a herbicidally effective amount of a
composition or tank mix comprising fluthiacet-methyl and an HPPD inhibitor. The HPPD
inhibitor can be mesotrione, sulcotrione, nitisinine, tembotrione, topramezone,
fenquinotrione, ketospiradox or tefuryltrione, and is preferably mesotrione. According to one
aspect of this embodiment, the fluthiacet-methyl and the HPPD inhibitor are present in a ratio
between about 1:2 and about 1:60 by weight. In a preferred aspect, the fluthiacet-methyl and
the HPPD inhibitor are present in a ratio between about 1:10 and about 1:40. In a more
preferred aspect, the fluthiacet-methyl and the HPPD inhibitor are present in a ratio between
about 1:15 and about 1:35. In another embodiment, the disclosure provides for methods for
making formulations comprising fluthiacet-methyl and an HPPD inhibitor. These can be
commercial formulations that are tank mixed at the time of application or more preferably a
suspension concentrate premix formulation. In a further aspect, the composition can contain
an additional crop protection agent. In another embodiment, the additional crop protection
agent is selected from atrazine, glyphosate, glufosinate, pyroxasulfone, dicamba,
diflufenzopyr, nicosulfuron, salts thereof, and mixtures of two or more thereof. In a preferred
aspect, the additional crop protection agent is atrazine.
DETAILED DESCRIPTION
[0009] The compositions of this disclosure include mixtures of fluthiacet-methyl and
a HPPD (p-hydroxyphenylpyruvate dioxygenase) inhibitor herbicide. In one embodiment,

the ratio of fluthiacet-methyl to HPPD inhibitor is about 1:2 to about 1:60 by weight,
preferably about 1:10 to about 1:40 and most preferred about 1:15 to about 1:35 by weight.
In another embodiment the ratio of fluthiacet-methyl to HPPD inhibitor is about 1:17.5 by
weight. In another embodiment the ratio of fluthiacet-methyl to HPPD inhibitor is about
1:32.5 by weight. These can be commercial formulations that are tank mixed at the time of
application, or more preferably, a suspension concentrate premix formulation. HPPD
herbicides include mesotrione, sulcotrione, nitisinine, tembotrione, topramezone,
fenquinotrione, ketospiradox and tefuryltrione. Preferably, the HPPD herbicide is
mesotrione.
[0010] The compositions of the present disclosure can be in any conventional
agriculturally useful form, for example, in the form of a twin pack, or in a ready-to-use
formulation, or in the form of a tank mix. Additionally, the active compounds can be
supplied (either separately or pre-mixed) in any appropriate formulation type, for example an
emulsion concentrate (EC), a suspension concentrate (SC), a suspo-emulsion (SE), a capsule
suspension (CS), a water dispersible granule (WG), an emulsifiable granule (EG), a water in
oil emulsion (EO), an oil in water emulsion (EW), a micro-emulsion (ME), an oil dispersion
(OD), an oil miscible flowable (OF), an oil miscible liquid (OL), a soluble concentrate (SL),
an ultra-low volume suspension (SU), an ultra-low volume liquid (UL), a dispersible
concentrate (DC), a wettable powder (WP) or any other technically feasible formulation in
combination with agriculturally acceptable adjuvants. For tank mixing, commercial
formulations of fluthiacet-methyl (CADET®) and the HPPD herbicide (for example,
mesotrione, commercial formulation CALLISTO®) are combined in a tank prior to
application, in the appropriate ratio to provide the targeted weight ratio of the active
ingredients. In one preferred embodiment, the compositions of the present disclosure are
supplied as premix suspension concentrates.

[0011] The compositions and tank mixes of the present disclosure are useful for the
control of susceptible weed species in crops such as corn and sugar cane. Susceptible weeds
include waterhemp, lambsquarters, velvetleaf, palmer amaranth, pigweed, morning glory,
cocklebur, ragweed, broadleaf signalgrass, foxtail, crabgrass, volunteer soybean, nutsedge,
Egyptian crowfoot grass, fumitory, denticulate medick, lesser swine cress, brown beetle
grass, jungle grass, tendla, false amaranth, common purslane and field bindweed, having an
average weed height of about 4 inches to about 8 inches. In one embodiment, the average
weed height is about 4 inches to about 6 inches; in a preferred embodiment the average weed
height is about 4 to about 5 inches. In another embodiment, the average weed height is
selected from about 4 to about 7 inches, or about 5 to about 6 inches, or about 5 to about 7
inches, or about 5 to about 8 inches, or about 6 to about 7 inches, or about 6 to about 8
inches, or about 7 to about 8 inches.
[0012] Rates of application of the composition, or tank-mixed separately formulated
active ingredients, will vary according to prevailing conditions such as targeted weeds,
degree of infestation, weather conditions, soil conditions, crop species, mode of application,
and application time. Compositions containing fluthiacet-methyl and an HPPD inhibitor can
be applied as sprays, such as water-dispersible concentrates, wettable powders, or water-
dispersible granules. In one embodiment, the rate of application for active ingredient ("ai")
(e.g. fluthiacet-methyl and an HPPD inhibitor) is from about 10 g ai/acre to about 500g
ai/acre, preferably about 50 g ai/acre to about 120 g ai/acre.
[0013] The compositions and tank mixes of the present disclosure can additionally
comprise further crop protection agents. Suitable crop protection active ingredients for the
formulations of the present disclosure include the following:
[0014] Insecticides: Al) the class of carbamates consisting of aldicarb, alanycarb,
benfuracarb, carbaryl, carbofuran, carbosulfan, methiocarb, methomyl, oxamyl, pirimicarb,

propoxur and thiodicarb; A2) the class of organophosphates consisting of acephate,
azinphos-ethyl, azinphos-methyl, chlorfenvinphos, chlorpyrifos, chlorpyrifos-methyl,
demeton-S-methyl, diazinon, dichlorvos/DDVP, dicrotophos, dimethoate, disulfoton, ethion,
fenitrothion, fenthion, isoxathion, malathion, methamidaphos, methidathion, mevinphos,
monocrotophos, oxymethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate,
phorate, phosalone, phosmet, phosphamidon, pirimiphos-methyl, quinalphos, terbufos,
tetrachlorvinphos, triazophos and trichlorfon; A3) the class of cyclodiene organochlorine
compounds such as endosulfan; A4) the class of fiproles consisting of ethiprole, fipronil,
pyrafluprole and pyriprole; A5) the class of neonicotinoids consisting of acetamiprid,
chlothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam; A6) the
class of spinosyns such as spinosad and spinetoram; A7) chloride channel activators from the
class of mectins consisting of abamectin, emamectin benzoate, ivermectin, lepimectin and
milbemectin; A8) juvenile hormone mimics such as hydroprene, kinoprene, methoprene,
fenoxycarb and pyriproxyfen; A9) selective homopteran feeding blockers such as
pymetrozine, flonicamid and pyrifluquinazon; A10) mite growth inhibitors such as
clofentezine, hexythiazox and etoxazole; Al 1) inhibitors of mitochondrial ATP synthase
such as diafenthiuron, fenbutatin oxide and propargite; uncouplers of oxidative
phosphorylation such as chlorfenapyr; A12) nicotinic acetylcholine receptor channel
blockers such as bensultap, cartap hydrochloride, thiocyclam and thiosultap sodium; A13)
inhibitors of the chitin biosynthesis type 0 from the benzoylurea class consisting of
bistrifluron, diflubenzuron, flufenoxuron, hexaflumuron, lufenuron, novaluron and
teflubenzuron; A14) inhibitors of the chitin biosynthesis type 1 such as buprofezin; A15)
moulting disruptors such as cyromazine; A16) ecdyson receptor agonists such as
methoxyfenozide, tebufenozide, halofenozide and chromafenozide; A17) octopamin receptor
agonists such as amitraz; A18) mitochondrial complex electron transport inhibitors

pyridaben, tebufenpyrad, tolfenpyrad, flufenerim, cyenopyrafen, cyflumetofen,
hydramethylnon, acequinocyl or fluacrypyrim;A19) voltage-dependent sodium channel
blockers such as indoxacarb and metaflumizone; A20) inhibitors of the lipid synthesis such
as spirodiclofen, spiromesifen and spirotetramat; A21) ryanodine receptor-modulators from
the class of diamides consisting of flubendiamide, the phthalamide compounds (R)-3-Chlor-
Nl - {2- methyl-4-[l ,2,2,2-tetrafluor-1 -(trifluormethyl)ethyl]phenyl} -N2-(l -methyl-2-
methylsulfonylethyl)phthalamidand(S)-3-Chlor-Nl-{2-methyl-4-[l,2,2,2-tetrafluor-l-
(trifluormethyl)ethyl]phenyl} -N2-( 1 - methyl-2-methylsulfonylethyl)phthalamid,
chloranthraniliprole and cyanthraniliprole; A22) compounds of unknown or uncertain mode
of action such as azadirachtin, amidoflumet, bifenazate, fluensulfone, piperonyl butoxide,
pyridalyl, sulfoxaflor; or A23) sodium channel modulators from the class of pyrethroids
consisting of acrinathrin, allethrin, bifenthrin, cyfluthrin, lambda-cyhalothrin, cypermethrin,
alpha-cypermethrin, beta-cypermethrin, zeta-cypermethrin, deltamethrin, esfenvalerate,
etofenprox, fenpropathrin, fenvalerate, flucythrinate, tau-fluvalinate, permethrin, silafluofen
and tralomethrin.
[0015] Fungicides: Bl) azoles selected from the group consisting of bitertanol,
bromuconazole, cyproconazole, difenoconazole, diniconazole, enilconazole, epoxiconazole,
fluquinconazole, fenbuconazole, flusilazole, flutriafol, hexaconazole, imibenconazole,
ipconazole, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole,
simeconazole, triadimefon, triadimenol, tebuconazole, tetraconazole, triticonazole,
prochloraz, pefurazoate, imazalil, triflumizole, cyazofamid, benomyl, carbendazim, thia-
bendazole, fuberidazole, ethaboxam, etridiazole and hymexazole, azaconazole, diniconazole-
M, oxpoconazol, paclobutrazol, uniconazol, l-(4-chlorophenyl)-2-([l,2,4]triazol-l-yl)-
cycloheptanol and imazalilsulfphate; B2) strobilurins selected from the group consisting of
azoxystrobin, dimoxystrobin, enestroburin, fluoxastrobin, kresoxim-methyl,

methominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, trifloxystrobin, enestroburin,
methyl (2-chloro-5-[l-(3-methylbenzyloxyimino)ethyl]benzyl)carbamate, methyl (2-chloro-
5-[l-(6-methylpyridin-2-ylmethoxyimino)ethyl]benzyl)carbamate and methyl 2-(ortho-(2,5-
dimethylphenyloxymethylene)- phenyl)-3 -methoxyacrylate, 2-(2-(6-(3 -chloro-2-methyl-
phenoxy)-5-fluoro-pyrimidin-4-yloxy)-phenyl)-2-methoxyimino-N-methyl-acetamide and 3 -
methoxy-2-(2-(N-(4-methoxy-phenyl)-cyclopropanecarboximidoylsulfanylmethyl)-phenyl)-
acrylic acid methyl ester; B3) carboxamides selected from the group consisting of carboxin,
benalaxyl, benalaxyl-M, fenhexamid, flutolanil, furametpyr, mepronil, metalaxyl,
mefenoxam, orurace, oxadixyl, oxycarboxin, penthiopyrad, isopyrazam, thifluzamide,
tiadinil, 3,4-dichloro-N-(2-cyanophenyl)isothiazole-5-carboxamide, dimethomorph,
flumorph, flumetover, fluopicolide (picobenzamid), zoxamide, carpropamid, diclocymet,
mandipropamid, N-(2- (4-[3-(4-chlorophenyl)prop-2-ynyloxy]-3-methoxyphenyl)ethyl)-2-
memanesulfonyl-amino-3 -methylbutyramide, N-(2-(4- [3 -(4-chlorophenyl)prop-2-ynyloxy]-3 -
methoxy-phenyl)ethyl)-2-ethanesulfonylamino- 3-methylbutyramide, methyl 3-(4-
chlorophenyl)-3 -(2-isopropoxycarbonyl- amino-3 -methyl-butyrylamino)propionate, N-(4"-
bromobiphenyl-2-yl)-4-difluoromethyl-methylthiazole-8-carboxamide, N-(4"-trifluoromethyl-
biphenyl-2-yl)-4-difluoromethyl-2-methylthiazole-5-carboxamide, N-(4"- chloro-3 "-
fluorobiphenyl-2-yl)-4-difluoromethyl-2-methyl-thiazole-5-carboxamide, N-(3,4"-dichloro-4-
fluorobiphenyl-2-yl)-3 -difluoro-methyl-1 -methyl-pyrazole-4-carboxamide, N-(3 ",4"-dichloro-
5-fluorobiphenyl-2-yl)-3 -difluoromethyl-1 -methylpyrazole-4-carboxamide, N-(2-cyano-
phenyl)- 3,4-dichloroisothiazole-5-carboxamide, 2-amino-4-methyl-thiazole-5-carboxanilide,
2-chloro-N-( 1,1,3 -trimethyl-indan-4-yl)-nicotinamide, N-(2-( 1,3-dimethylbutyl)-phenyl)-1,3 -
dimethyl-5-fluoro-1 H-pyrazole-4-carboxamide, N-(4"-chloro-3 ",5-difluoro-biphenyl-2-yl)-3 -
difluoromethyl-1 -methyl-I H-pyrazole-4-carboxamide, N-(4"-chloro-3",5-difluoro-biphenyl-
2-yl)-3-trifluoromethyl-l -methyl-lH-pyrazole-4-carboxamide, N-(3",4"- dichloro-5-fluoro-

biphenyl-2-yl)-3-trifluoromethyl-1 -methyl-1 H-pyrazole-4-carboxamide, N-(3",5-difluoro-4"-
methyl-biphenyl-2-yl)-3 -difluoromethyl-1 -methyl-1 H-pyrazole-4-carboxamide, N-(3 ",5-
difluoro-4"-methyl-biphenyl-2-yl)-3 -trifluoromethyl-1 -methyl-1 H-pyrazole-4-carboxamide,
N-(cis-2-bicyclopropyl-2-yl-phenyl)-3-difluoromethyl-1 -methyl-1 H-pyrazole-4-carboxamide,
N-(trans-2-bicyclopropyl-2-yl-phenyl)-3-difluoro-methyl-1 -methyl-1 H-pyrazole-4-
carboxamide, fluopyram, N-(3-ethyl-3,5-5- trimethyl-cyclohexyl)-3-foraiylamino-2-hydroxy-
benzamide, oxytetracyclin, silthiofam, N-(6-methoxy-pyridin-3-yl)
cyclopropanecarboxamide, 2-iodo-N-phenyl-benzamide, N-(2-bicyclo-propyl-2-yl-phenyl)-3 -
difluormethyl-1 -methylpyrazol-4-ylcarboxamide, N-(3 ",4",5"-trifluorobiphenyl-2-yl)-1,3-
dimethylpyrazol-4-ylcarboxamide, N-(3",4",5"-trifluorobiphenyl-2-yl)-l,3-dimethyl-5-
fluoropyrazol-4-ylcarboxamide, N-(3",4",5,-trifluorobiphenyl-2-yl)-5-chloro-l,3-dimethyl-
pyrazol-4-ylcarboxamide, N-(3",4",5"-trifluorobiphenyl-2-yl)-3- fluoromethyl-1 -
methylpyrazol-4-ylcarboxamide, N-(3 ",4",5"- trifluorobiphenyl-2-yl)-3 -(chlorofluoromethyl)-
l-methylpyrazol-4- ylcarboxamide,N-(3",4",5"-trifluorobiphenyl-2-yl)-3-difluoromethyl-l-
methylpyrazol-4-ylcarboxamide, N-(3",4",5"-trifluorobiphenyl-2-yl)-3-difluoromethyl-5-
fluoro-l-methylpyrazol-4-ylcarboxamide, N-(3",4",5"-trifluorobiphenyl-2- yl)-5-chloro-3-
difluoromethyl-l-methylpyrazol-4-ylcarboxamide, N- (3", 4", 5"-trifluorobiphenyl-2-yl)-3-
(chlorodifluoromethyl)-l-methylpyrazol-4-ylcarboxamide, N-(3",4"55,-trifluorobiphenyl-2-yl)-
1 -methyl-3-trifluoromethylpyrazol-4-ylcarboxamide, N-(3",4",5"-trifluorobiphenyl-2-yl)- 5-
fluoro-1 -methyl-3 -trifluoromethylpyrazol-4-ylcarboxamide, N-(3 ",4", 5 "-trifluorobiphenyl-2-
yl)-5-chloro-1 -methyl-3- trifluoromethylpyrazol-4-ylcarboxamide, N-(2",4",5"-
trifluorobiphenyl-2-yl)-1,3-dimethylpyrazol-4-ylcarboxamide, N-(2",4",5 "-trifluorobiphenyl-2-
yl)-l,3-dimethyl-5-fluoropyrazol-4-ylcarboxamide, N-(2",4",5"-trifluorobiphenyl-2-yl)-5-
chloro-1 ,3-dimetliylpyrazol-4-ylcarboxamide, N- (2",4",5"-trifluorobiphenyl-2-yl)-3-
fluoromethyl-1 -methylpyrazol-4-ylcarboxamide, N-(2",4",5"-trifluorobiphenyl-2-yl)-3 -

(chlorofluoromethyl)-1 -methylpyrazol-4-ylcarboxamide,N-(2",4",5"-trifluorobiphenyl-2-yl)-3 -
difluoromethyl-l-methylpyrazol-4-ylcarboxamide, N-(2",4",5"-trifluorobiphenyl-2-yl)-3-
difluoromethyl-5-fluoro-l-methylpyrazol-4-ylcarboxamide, N-(2",4",5"-trifluorobiphenyl-2-
yl)-5-chloro-3-difluoromethyl-l-methylpyrazol-4-ylcarboxamide, N-(2",4",5"-
trifluorobiphenyl-2-yl)-3-(chlorodifluoromethyl)-1 -methylpyrazol-4-ylcarboxarnide, N-
(2",4",5"-trifluorobiphenyl-2-yl)-l-methyl-3- trifluoromethylpyrazol-4-ylcarboxamide, N-
(2",4",5,-trifluorobiphenyl-2-yl)- 5-fluoro-1 -methyl-3-trifluoromethylpyrazol-4-
ylcarboxamide, N-(2",4",5"-trifluorobiphenyl-2-yl)-5-chloro-l-methyl-3-
trifluoromethylpyrazol-4-ylcarboxamide, N-(3",4"-dichloro-3-fluorobiphenyl-2-yl)-l-methyl-
3-trifluoromethyl-lH-pyrazole-4-carboxamide, N-(3",4"-dichloro-3- fluorobiphenyl-2-yl)-l -
methyl-3-difluoromethyl-lH-pyrazole-4-carboxamide, N-(3",4"-difluoro-3-fluorobiphenyl-2-
yl)-1 -methyl-3-trifluoromethyl-1 H-pyrazole-4-carboxamide, N-(3 ",4"-difluoro-3 -
fluorobiphenyl-2-yl)-1 -methyl-S-difluoromethyl-1 H-pyrazole-4-carboxamide, N-(3 "-chloro-
4"- fluoro-3 -fluorobiphenyl-2-yl)-1 -methyl-3 -difluoromethyl-1 H-pyrazole-4-carboxamide,
N-(3 ",4"-dichloro-4-fluorobiphenyl-2-yl)-1 -methyl-3 -trifluoromethyl-1 H- pyrazole-4-
carboxamide, N-(3 ",4"-difluoro-4-fluorobiphenyl-2-yl)-1 - methyl-S-trifluoromethyl-1H-
pyrazole-4-carboxamide, N-(3",4"-dichloro-4- fluorobiphenyl-2-yl)-l -methyl-S-
difluoromethyl- 1 H-pyrazole-4-carboxamide, N-(3 ",4"-difluoro-4-fluorobiphenyl-2-yl)-1 -
methyl-3-difluoromethyl-1H- pyrazole-4-carboxamide, N-(3 "-chloro-4"-fluoro-4-
fluorobiphenyl-2-yl)-1 -methyl-S-difluoromethyl-1 H-pyrazole-4-carboxamide, N-(3",4"-
dichloro-5- fluorobiphenyl-2-yl)-1 -methyl-3 -trifluoromethyl-1 H-pyrazole-4-carboxamide, N-
(3 "54"-difluoro-5-fluorobiphenyl-2-yl)-1 -methyl-3 -trifluoromethyl-1H- pyrazole-4-
carboxamide, N-(3",4"-dichloro-5-fluorobiphenyl-2-yl)-l-methyl-S-difluoromethyl-lH-
pyrazole-4-carboxamide, N-(3 ",4"-difluoro-5- fluorobiphenyl-2-yl)-1 -methyl-3 -
difluoromethyl-1 H-pyrazole-4-carboxamide, N-(3",4"-dichloro-5-fluorobiphenyl-2-yl)-l,3-

dimethyl-1 H-pyrazole-4-carboxamide, N-(3 "-chloro-4"-fluoro-5-fluorobiphenyl-2-yl)-1 -
methyl-3- difluoromethyl-1 H-pyrazole-4-carboxamide, N-(4"-fluoro-4-fluorobiphenyl-2-yl)-1
-methyl-3 -trifluoromethyl-1 H-pyrazole-4-carboxamide, N-(4"-fluoro- 5-fluorobiphenyl-2-yl)-
l-methyl-3-trifluoromethyl-lH-pyrazole-4-carboxamide,N-(4"-chloro-5-fluorobiphenyl-2-yl)-
1 -methyl-3 -trifluoromethyl-1H- pyrazole-4-carboxamide, N-(4"-methyl-5-fluorobiphenyl-2-
yl)-1 -methyl-3-trifluoromethyl-1 H-pyrazole-4-carboxamide, N-(4"-fluoro-5- fluorobiphenyl-
2-yl)-1,3 -dimethyl-1 H-pyrazole-4-carboxamide, N-(4"- chloro-5-fluorobiphenyl-2-yl)-1,3-
dimethyl-1 H-pyrazole-4-carboxamide, N-(4"-methyl-5-fluorobiphenyl-2-yl)-1,3 -dimethyl-
lH-pyrazole-4-carboxamide, N-(4"-fluoro-6-fluorobiphenyl-2-yl)-l-methyl-3-trifluoromethyl-
1H- pyrazole-4-carboxamide, N-(4"-chloro-6-fluorobiphenyl-2-yl)-1 -methyl-3-
trifluoromethyl-lH-pyrazole-4-carboxamide, N-[2-(l,1,2,3,3,3- hexafluoropropoxy)-phenyl]-
3 -difluoromethyl-1 -methyl-1 H-pyrazole-4-carboxamide, N- [4"-(trifluoromethylthio)-
biphenyl-2-yl]-3-difluoromethyl-l-methyl-lH-pyrazole-4-carboxamide andN-[4"-
(trifluoromethylthio)-biphenyl-2-yl]-1 -methyl-3-trifluoromethyl-1 -methyl-1 H-pyrazole-4-
carboxamide; B4) heterocyclic compounds selected from the group consisting of fluazinam,
pyrifenox, bupirimate, cyprodinil, fenarimol, ferimzone, mepanipyrim, nuarimol,
pyrimethanil, tiiforine, fenpiclonil, fludioxonil, aldimorph, dodemorph, fenpropimorph,
tridemorph, fenpropidin, iprodione, procymidone, vinclozolin, famoxadone, fenamidone,
octhilinone, proben- azole, 5-chloro-7-(4-methyl-piperidin-l-yl)-6-(2,4,6-trifluorophenyl)-
[l,2,4]triazolo[l,5-a]pyrimidine, anilazine, diclomezine, pyroquilon, proquinazid,
tricyclazole, 2-butoxy-6-iodo-3-propylchromen-4-one, acibenzolar-S-methyl, captafol,
captan, dazomet, folpet, fenoxanil, quinoxyfen, N,N-dimethyl-3-(3-bromo-6-fluoro-2-
methylindole-1-sulfonyl)- [l,2,4]triazole-l-sulfonamide, 5-ethyl-6-octyl-[l,2,4]triazolo[l,5-
a]pyrimidin-2,7-diamine, 2,3,5,6-tetrachloro-4-methanesulfonyl-pyridine, 3,4,5-trichloro-
pyridine-2,6-di-carbonitrile, N-(l-(5-bromo-3-chloro-pyridin-2-yl)-ethyl)-2,4-dichloro-

nicotinamide, N-((5-bromo-3-chloropyridin-2-yl)-methyl)-2,4-dichloro-nicotinamide,
diflumetorim, nitrapyrin, dodemorphacetate, fluoroimid, blasticidin-S, chinomethionat,
debacarb, difenzoquat, difenzoquat-methylsulphate, oxolinic acid and piperalin; B5)
carbamates selected from the group consisting of mancozeb, maneb, metam,
methasulphocarb, metiram, ferbam, propineb, thiram, zineb, ziram, diethofencarb,
iprovalicarb, benthiavalicarb, propamocarb, propamocarb hydrochlorid, 4-fluorophenyl N-(l-
(l-(4-cyanophenyl)- ethanesulfonyl)but-2-yl)carbamate, methyl 3-(4-chloro-phenyl)-3-(2-
isopropoxycarbonylamino-3-methyl-butyrylamino)propanoate; or B6) other fungicides
selected from the group consisting of guanidine, dodine, dodine free base, iminoctadine,
guazatine, antibiotics: kasugamycin, streptomycin, polyoxin, validamycin A, nitrophenyl
derivatives: binapacryl, dinocap, dinobuton, sulfur-containing heterocyclyl compounds:
dithianon, isoprothiolane, organometallic compounds: fentin salts, organophosphorus
compounds: edifenphos, iprobenfos, fosetyl, fosetyl-aluminum, phosphorous acid and its
salts, pyrazophos, tolclofos- methyl, organochlorine compounds: dichlofluanid, flusulfamide,
hexachloro- benzene, phthalide, pencycuron, quintozene, thiophanate-methyl, tolylfluanid,
others: cyflufenamid, cymoxanil, dimethirimol, ethirimol, furalaxyl, metrafenone and
spiroxamine, guazatine-acetate, iminoctadine-triacetate, iminoctadine-tris(albesilate),
kasugamycin hydrochloride hydrate, dichlorophen, pentachlorophenol and its salts, N-(4-
chloro-2-nitro-phenyl)-N-ethyl-4-methyl-benzenesulfonamide, dicloran, nitrothal-isopropyl,
tecnazen, biphenyl, bronopol, diphenylamine, mildiomycin, oxincopper, prohexadione
calcium, N- (cyclopropylmethoxyimino-(6-difluoromethoxy-2,3-difluoro-phenyl)- methyl)-2-
phenyl acetamide, N"-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-
N-methyl formamidine, N"-(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-
ethyl-N-methyl formamidine, N"-(2-methyl-5-trifluormethyl-4-(3-trimethylsilanyl-propoxy)-

phenyl)-N-emyl-N-memylfonnamidine and N"-(5-difluormethyl-2-methyl- 4-(3-
trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N-methylformaniidine.
[0016] Herbicides: CI) acetyl-CoA carboxylase inhibitors (ACC), for example
cyclohexenone oxime ethers, such as alloxydim, clethodim, cloproxydim, cycloxydim,
sethoxydim, tralkoxydim, butroxydim, clefoxydim or tepraloxydim;
phenoxyphenoxypropionic esters, such as clodinafop-propargyl, cyhalofop-butyl, diclofop-
methyl, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenthiapropethyl, fluazifop-butyl, fluazifop-P-
butyl, haloxyfop-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl, isoxapyrifop,
propaquizafop, quizalofop-ethyl, quizalofop-P-ethyl or quizalofop-tefuryl; or
arylaminopropionic acids, such as flamprop-methyl or flamprop-isopropyl; C2 acetolactate
synthase inhibitors (ALS), for example imidazolinones, such as imazapyr, imazaquin,
imazamethabenz-methyl (imazame), imazamox, imazapic or imazethapyr; pyrimidyl ethers,
such as pyrithiobac-acid, pyrithiobac-sodium, bispyribac-sodium. KIH-6127 or
pyribenzoxym; sulfonamides, such as florasulam, flumetsulam or metosulam; or
sulfonylureas, such as amidosulfuron, azimsulfuron, bensulfuron-methyl, chlorimuron-ethyl,
chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron-methyl, ethoxysulfuron,
flazasulfuron, halosulfuron-methyl, imazosulfuron, metsulfuron-methyl, nicosulfuron,
primisulfuron-methyl, prosulfuron, pyrazosulfuron-ethyl, rimsulfuron, sulfometuron-methyl,
thifensulfuron-methyl, triasulfuron, tribenuron-methyl, triflusulfuron-methyl, tritosulfuron,
sulfosulfuron, foramsulfuron or iodosulfuron; C3) amides, for example allidochlor (CDAA),
benzoylprop-ethyl, bromobutide, chlorthiamid. diphenamid, etobenzanid, fluthiamide,
fosamin or monalide; C4) auxin herbicides, for example pyridinecarboxylic acids, such as
clopyralid or picloram; or 2,4-D or benazolin; C5) auxin transport inhibitors, for example
naptalame or diflufenzopyr; C6) carotenoid biosynthesis inhibitors, for example benzofenap,
clomazone, diflufenican, fluorochloridone, fluridone, pyrazolynate, pyrazoxyfen,

isoxaflutole, isoxachlortole, mesotrione, sulcotrione (chlormesulone), ketospiradox,
flurtamone, norfliirazon or amitrol; C7) enolpyruvylshikimate-3-phosphate synthase
inhibitors (EPSPS), for example glyphosate or sulfosate; C8) glutamine synthetase inhibitors,
for example bilanafos or glufosinate-ammonium; C9) lipid biosynthesis inhibitors, for
example anilides, such as anilofos or mefenacet; chloroacetanilides, such as dimethenamid,
S-dimethenamid, acetochlor, alachlor, butachlor, butenachlor, diethatyl-ethyl, dimethachlor,
metazachlor, metolachlor, S-metolachlor, pretilachlor, propachlor, prynachlor, terbuchlor,
thenylchlor or xylachlor; thioureas, such as butylate, cycloate, di-allate, dimepiperate, EPTC.
esprocarb, molinate, pebulate, prosulfocarb, thiobencarb (benthiocarb), tri-allate or vemolate;
or benfuresate or perfluidone; CIO) mitosis inhibitors, for example carbamates, such as
asulam, carbetamid, chlorpropham, orbencarb, propyzamid, propham or tiocarbazil;
dinitroanilines, such as benefin, butralin, dinitramin, ethalfluralin, fluchloralin, oryzalin,
pendimethalin, prodiamine or trifluralin; pyridines, such as dithiopyr or thiazopyr; or
butamifos, chlorthal-dimethyl (DCPA) or maleic hydrazide; CI 1) protoporphyrinogen IX
oxidase inhibitors, for example diphenyl ethers, such as acifluorfen, acifluorfen-sodium,
aclonifen, bifenox, chlomitrofen (CNP), ethoxyfen, fluorodifen, fluoroglycofen-ethyl,
fomesafen, furyloxyfen, lactofen, nitrofen, nitrofluorfen or oxyfluorfen; oxadiazoles, such as
oxadiargyl or oxadiazon; cyclic imides, such as azafenidin, butafenacil, carfentrazone-ethyl,
cinidon-ethyl, flumiclorac-pentyl, flumioxazin, flumipropyn, flupropacil, fluthiacet-methyl,
sulfentrazone or thidiazimin; or pyrazoles, such as ET-751, JV 485 or nipyraclofen; CI2)
photosynthesis inhibitors, for example propanil, pyridate or pyridafol; benzothiadiazinones,
such as bentazone; dinitrophenols, for example bromofenoxim, dinoseb, dinoseb-acetate,
dinoterb or DNOC; dipyridylenes, such as cyperquat-chloride, difenzoquat-methylsulfate,
diquat or paraquat-dichloride; ureas, such as chlorbromuron, chlorotoluron, difenoxuron,
dimefuron, diuron, ethidimuron, fenuron, fluometuron, isoproturon, isouron, linuron,

methabenzthiazuron, methazole, metobenzuron, metoxuron, monolinuron, neburon, siduron
or tebuthiuron; phenols, such as bromoxynil or ioxynil; chloridazon; triazines, such as
ametryn, atrazine, cyanazine, desmein, dimethamethryn, hexazinone, prometon, prometryn,
propazine, simazine, simetryn, terbumeton, terbutryn, terbutylazine or trietazine; triazinones,
such as metamitron or metribuzin; uracils, such as bromacil, lenacil or terbacil; or
biscarbamates, such as desmedipham or phenmedipham; CI3) synergists, for example
oxiranes, such as tridiphane; CI4) CIS cell wall synthesis inhibitors, for example isoxaben or
dichlobenil; CI6) various other herbicides, for example dichloropropionic acids, such as
dalapon; dihydrobenzofurans, such as ethofumesate; phenylacetic acids, such as chlorfenac
(fenac); or aziprotryn, barban, bensulide, benzthiazuron, benzofluor, buminafos, buthidazole,
buturon, cafenstrole, chlorbufam, chlorfenprop-methyl, chloroxuron, cinmethylin,
cumyluron, cycluron, cyprazine, cyprazole, dibenzyluron, dipropetryn, dymron, eglinazin-
ethyl, endothall, ethiozin, flucabazone, fluorbentranil, flupoxam, isocarbamid, isopropalin,
karbutilate, mefluidide, monuron, napropamide, napropanilide, nitralin, oxaciclomefone,
phenisopham, piperophos, procyazine, profluralin, pyributicarb, secbumeton, sulfallate
(CDEC), terbucarb, triaziflam, triazofenamid or trimeturon; or their environmentally
compatible salts.
[0017] Plant Growth Regulators: Dl) Antiauxins, such as clofibric acid, 2,3,5-tri-
iodobenzoic acid; D2) Auxins such as 4-CPA, 2,4-D, 2,4-DB, 2,4-DEP, dichlorprop,
fenoprop, IAA ,IBA, naphthaleneacetamide, a-naphthaleneacetic acids, 1-naphthol,
naphthoxyacetic acids, potassium naphthenate, sodium naphthenate, 2,4,5-T; D3) cytokinins,
such as 2iP, benzyladenine, 4-hydroxyphenethyl alcohol, kinetin, zeatin; D4) defoliants, such
as calcium cyanamide, dimethipin, endothal, ethephon, merphos, metoxuron,
pentachlorophenol, thidiazuron, tribufos; D5) ethylene inhibitors, such as aviglycine, 1-
methylcyclopropene; D6) ethylene releasers, such as ACC, etacelasil,ethephon, glyoxime;

D7) gametocides, such as fenridazon, maleic hydrazide; D8) gibberellins, such as
gibberellins, gibberellic acid; D9) growth inhibitors, such as abscisic acid, ancymidol,
butralin, carbaryl, chlorphonium, chlorpropham, dikegulac, flumetralin, fluoridamid,
fosamine, glyphosine, isopyrimol, jasmonic acid, maleic hydrazide, mepiquat, piproctanyl,
prohydrojasmon, propham, tiaojiean, 2,3,5-tri-iodobenzoic acid; D10) morphactins, such as
chlorfluren, chlorflurenol, dichlorflurenol, flurenol; Dl 1) growth retardants, such as
chlormequat, daminozide, flurprimidol, mefluidide, paclobutrazol, tetcyclacis, uniconazole;
D12) growth stimulators, such as brassinolide, brassinolide-ethyl, DCPTA, forchlorfenuron,
hymexazol, prosuler, triacontanol; D13) unclassified plant growth regulators, such as
bachmedesh, benzofluor, buminafos, carvone, choline chloride, ciobutide, clofencet,
cyanamide, cyclanilide, cycloheximide, cyprosulfamide, epocholeone, ethychlozate, ethylene,
fuphenthiourea, furalane, heptopargil, holosulf, inabenfide, karetazan, lead arsenate,
methasulfocarb, prohexadione, pydanon, sintofen, triapenthenol, trinexapac.
[0018] The compositions of the present disclosure can also include a preservative.
Suitable preservatives include but are not limited to C12 to C\5 alkyl benzoates, alkyl p-
hydroxybenzoates, aloe vera extract, ascorbic acid, benzalkonium chloride, benzoic acid,
benzoic acid esters of C9 to C15 alcohols, butylated hydroxytoluene, butylated
hydroxyanisole, tert-butylhydroquinone, castor oil, cetyl alcohols, chlorocresol, citric acid,
cocoa butter, coconut oil, diazolidinyl urea, diisopropyl adipate, dimethyl polysiloxane,
DMDM hydantoin, ethanol, ethylenediaminetetraacetic acid, fatty acids, fatty alcohols,
hexadecyl alcohol, hydroxybenzoate esters, iodopropynyl butylcarbamate, isononyl iso-
nonanoate, jojoba oil, lanolin oil, mineral oil, oleic acid, olive oil, parabens, polyethers,
polyoxypropylene butyl ether, polyoxypropylene cetyl ether, potassium sorbate, propyl
gallate, silicone oils, sodium propionate, sodium benzoate, sodium bisulfite, sorbic acid,
stearic fatty acid, sulfur dioxide, vitamin E, vitamin E acetate and derivatives, esters, salts

and mixtures thereof. Preferred preservatives include sodium o-phenylphenate, 5-chloro-2-
methyl-4-isothiazolin-3-one, 2-methyl-4-isothiazolin-3-one, and l,2-benisothiazolin-3-one.
[0019] In one preferred embodiment, the additional crop protection agent is atrazine.
Increased herbicidal activity was observed when atrazine was added to the composition of
Example 2, vide infra, in control of ivyleaf morningglory, waterhemp, giant foxtail, green
foxtail and giant ragweed. The herbicidal activity of the compositions of this disclosure can
be used to control herbicide-resistant weeds, such as glyphosate-resistant weeds, including
glyphosate-resistant waterhemp.
DEFINITIONS
[0020] As used in this application and unless otherwise indicated the term "herbicide"
refers to a compositional mixture that is produced, sold, or used in a field in order to kill or
otherwise inhibit unwanted plants such as, but not limited to, deleterious or annoying weeds,
broadleaf plants, grasses, and sedges; and can be used for crop protection, edifice protection
or turf protection. The term "herbicide" includes the end-use herbicidal product. This
composition can be a pure compound, a solution of chemical compounds, a mixture of
chemical compounds, an emulsion, a suspension, a solid-liquid mixture, or a liquid- liquid
mixture. The term "herbicide" also refers to the product that passes through the commercial
channels from the manufacturer to the ultimate end user who can either apply the herbicide to
the affected field as sold, or mix it with other excipients.
[0021] The term "weed" means and includes any plant which grows where not
wanted.
[0022] The term "herbicidally effective amount" means an amount necessary to
produce an observable herbicidal effect on unwanted plant growth, including one or more of
the effects of necrosis, death, growth inhibition, reproduction inhibition, inhibition of

proliferation, and removal, destruction, or otherwise diminishing the occurrence and activity
of unwanted plants.
[0023] The term "herbicidally active ingredient" means the active ingredient in the
herbicide that causes the herbicide to prevent, destroy, repel or mitigate any weed. Other
ingredients of the herbicide that are not herbicidally active ingredients are excipients that aid
in forming, storing, or delivering herbicidally active ingredient to the target. Examples of
excipients in the present embodiment include, without limitation, an organic liquid in which
herbicidally active ingredient is dissolved, a polyurea shell, a water-soluble polymer, and one
or more salts.
[0024] The definition of the term "herbicidal composition" refers to a herbicide, and
in addition, to any composition that comprises a herbicidally active ingredient. This
composition can be a solution or a mixture. Further, the definition of the term "herbicidal
composition" also refers to a product intended for use in manufacruting, or any product
intended for formulation or repackaging into other agricultural products.
[0025] "Fluthiacet-methyl" is the common name for methyl [[2-chloro-4-fluoro-5-
[(tetrahydro-3 -oxo-1 H,3H- [ 1,3,4]thiadiazolo[3,4-a]pyridazin-1 -ylidene)amino]phenyl]thio]
acetate.
[0026] "HPPD inhibitor" means a compound that inhibits para-hydroxyphenyl-
pyruvate dioxygenase.
[0027] The following examples serve only to illustrate the invention and should not
be interpreted as limiting the scope of the invention in any way, since further modifications
encompassed by the disclosed invention will be apparent to those skilled in the art. All such
modifications are deemed to be within the scope of the invention as defined in the present
specification and claims.

EXAMPLES
Example 1: SC Formulation of Fluthiacet-methyl and Mesotrione, 1:17.5 Ratio by Weight
[0028] A mixture of 51.8 grams of magnesium aluminum silicate (VEEGUM® Ultra,
available from Vanderbuilt Minerals LLC) in 3,077.0 grams of deionized water was stirred
vigorously for about one hour at room temperature. To this was added 511.8 grams of
propylene glycol, 10.8 grams of an antifoam agent (Dow Corning® AF Emulsion, available
from Dow Corning Corporation), 204.9 grams of a wetting agent (Morwet D-425® Powder,
available from AkzoNobel Agrochemicals), 257.0 grams of premelted polyalkylene oxide
block copolymer (Atlas™ G-5000, available from Croda Crop Care) and 256.7 grams of an
acrylic graft copolymer (Atlox® 491, available from Croda Crop Care). The mixture was
stirred until uniform. Technical grade mesotrione (5,594.0 grams, 83.0% purity) and
fluthiacet-methyl (273 grams, 97.5% purity) were added and the mixture milled at a
temperature of about 35°C to about 45°C until a particle size of less than 3 microns was
achieved. The milled mixture was transferred to a tank fixed with a stirring blade. The mill
tank was rinsed with about 170 grams of deionized water and the rinse added to the milled
mixture. To this was added 1,080.0 grams of an aqueous mixture containing 2% by weight
xanthan gum and 1.3% by weight biocide (Kathon™ Preserative, available from Dow
Chemical Company). This was stirred for four hours at which time the pH was adjusted to
4.62 by adding 10.3 grams of triethanolamine. An additional 171.0 grams of deionized water
was added and the mixture stirred until homogenous. Analysis of this mixture indicated it
contained 38.4% by weight mesotrione, 2.22% by weight fluthiacet-methyl with an average
particle size of 1.63(D90) and a density of 1.18 gm/mL.
Example 2: SC Formulation of Fluthiacet-methyl and Mesotrione, 1:32.5 Ratio by Weight
[0029] A mixture of 72.8 grams of magnesium aluminum silicate (VEEGUM® Ultra,
available from Vanderbuilt Minerals LLC) in 4,369.3 grams of deionized water was stirred

vigorously for about one hour at room temperature. To this was added 728.2 grams of
propylene glycol, 14.6 grams of an antifoam agent (Dow Corning® AF Emulsion, available
from Dow Corning Corporation), 291.3 grams of a wetting agent (Morwet D-425® Powder,
available from AkzoNobel Agrochemicals), 364.1 grams of premelted polyalkylene oxide
block copolymer (Atlas™ G-5000, available from Croda Crop Care) and 364.1 grams of an
acrylic graft copolymer (Atlox® 491, available from Croda Crop Care). The mixture was
stirred until uniform. Technical grade mesotrione (4,499.8 grams, 83.0% purity) and
fluthiacet-methyl (119.5 grams, 97.5% purity) were added and the mixture milled at a
temperature of about 35°C to about 45°C until a particle size of less than 3 microns was
achieved. The milled mixture was transferred to a tank fixed with a stirring blade. The mill
tank was rinsed with 1324.0 grams of deionized water and the rinse added to the milled
mixture. To this was added 1,243.9 grams of an aqueous mixture containing 2% by weight
xanthan gum and 1.3% by weight biocide (Kathon™ Preserative, available from Dow
Chemical Company). This was stirred for four hours at which time the pH was adjusted to
4.8 by adding 24.7 grams of triethanolamine. An additional 1324.3 grams of deionized water
was added and the mixture stirred until homogenous. Analysis of this mixture indicated it
contained 30.6% by weight mesotrione, 0.81% by weight fluthiacet-methylwith an average
particle size of 2.31(D90) and a density of 1.14 gm/mL.
Example 3: Post-emergent Herbicidal Evaluation of Fluthiacet-Methyl In Mixtures With
HPPD Herbicides
[0030] Compositions of the present disclosure were tested for herbicidal efficacy in
the following manner:
[0031] Test compositions containing Fluthiacet-methyl (Cadet® Herbicide),
tembotrione (Laudis® Herbicide), topramezone (Impact® Herbicide), mesotrione (Callisto®
Herbicide) and mixtures of fluthiacet-methyl with these HPPD herbicides, were diluted with

water to provide the appropriate test rate concentrations. A crop oil concentrate (1% v/v,
crop oil concentrate, COC, or methylated seed oil, MSO) was added to each test solution.
[0032] The test crop was Pioneer 33M53 corn and the test weeds were redroot
pigweed (Amaranthus retroflexus), morningglory (Ipamea spp) and common waterhemp
(Amaranthus rudis).
[0033] For post-emergence testing, three disposable 3 inch square pots for each rate
of application of each herbicide solution were filled with a soil, comprised of peat moss,
vermiculite, bark ash, pine bark, limestone and a wetting agent (Metro Mix 360 artificial soil,
Scotts Company, Marysville, OH), to which 8 to 10 seeds were planted. The pots were
placed in a greenhouse and watered daily, thus allowing the seeds to germinate and the
foliage to develop into 5 inch to 6 inch plants.
[0034] Pots designated for treatment were placed on a conveyor belt and the conveyor
belt fed under a spray nozzle mounted about ten inches above the post-emergent foliage. The
spray of herbicidal solution was commenced and once stabilized; the pots were passed under
the spray at a speed to receive a coverage equivalent of 30 gallons per acre. The application
rates are those shown in Table 1 below for the individual herbicidal solutions and the
herbicide compositions of the present disclosure. The post-emergence pots were immediately
placed in the green-house and not watered for 24 hours after treatment. Thereafter they were
regularly watered at ground level. The control of weeds was evaluated in each experimental
test at 21 days after treatment (DAT). The results after 21 days, shown as an average of the
replications, were compared with results observed in untreated control pots in the same tests.
The results are in Table 1 below. Test mixtures of fluthiacet-methyl-methyl and HPPD
herbicides were found to exhibit similar or less crop injury then the individually applied
herbicides when applied to field corn.

[0035] Percent control was determined by a method similar to the 0 to 100 rating
system disclosed in "Research Methods in Weed Science," 2nd ed., B. Truelove, Ed.;
Southern Weed Science Society; Auburn University, Auburn, Ala., 1977. The rating system
is as follows:



Example 4: Post-emergence Control of Weeds Using Fluthiacet-methyl and Mesotrione
[0036] Compositions of the present disclosure were tested for herbicidal efficacy in
the following manner:
[0037] Test compositions containing Fluthiacet-methyl (Cadet® Herbicide),
mesotrione (15% SC formulation), mixtures of Cadet® Herbicide and mesotrione 15% SC,
and the formulation of Example 2 were diluted with water to provide the appropriate test rate
concentrations.

[0038] The test weeds include purple nutsedge (Cyperus rotundus, PN), Egyptian
crowfoot grass (Dactylocatenium aegyptim, ECG), fumitory (Fumaria indica, FUM), giant
pigweed {Trianthema protulacastrum, GPW), lambsquarters (Chenopodium album, LQ),
denticulate medick (Medacigo denticulate, DM), lesser swine cress (Coronopus dodymus,
LSC), brown beetle grass (Diplachne fusca, BBG), jungle grass (Echinochloa colonum, JG),
tendla {Digera arvensis, TEN), and field bindweed (Convolvulus arvensis, FBW).
[0039] The test compositions were sprayed on 800 to 1000 square foot test plots (9
replicates at 3 sites in India, one in Lahore and two in) using a back pack sprayer at a rate of
188 liters per hectare when the crop (grain hybrid corn) and weeds were at the 4 to 5 leaf
growth stage. The percent phytotoxicity to corn (discoloration of leaves and miss-shaped
leaves) was determined at 10 days after treatment (DAT) and the percent control of weeds
was determined at 45 DAT. Table 2 below summarizes this data. The untreated control plots
had no damage to the corn and no control of weeds.
[0040] The expected phytotoxicity to corn and the expected control of weeds is
calculated using the Colby Equation (S. R. Colby, Weeds, Vol. 15, No. 1, pgs 20-22, 1967)
and is also provide in the table below. The Expected value "E" is calculated using the
following equation; E = X+Y- (XY/100); where X is the observed control of the first active at
rate xl and Y is the observed control of the second active at rate yl. When the observed
response of the combination is greater than the expected, the combination is synergistic;
when less than expected, it is antagonistic; when the observed and expected are the same, the
combination is additive.


Example 5: Weed Control in Sugarcane Field Tests
[0041] The composition of Example 2 was tested in sugarcane fields in India for
weed control and crop safety. The composition of Example 2 was diluted with water and
applied to test plots of 800 to 1000 square foot at five sugarcane farm locations. The
composition was applied at a rate of 400, 500 and 600 mL of test composition per acre as pre-
emergence and early post-emergence applications (15 days after sowing) using backpack
sprayers. A pre-emergent standard, Metric® Herbicide (clomazone and metribuzin) and a
post-emergent standard, Flisto Gold® Herbicide (atrazine and mesotrione) were included at 1
liter formulation diluted in water per acre. The data from all 5 trials was averaged and
summarized in Table 3 below. Untreated control plots were also included. Data for the pre-
emergence trials was collected 20-25 days after application; early post-emergence data was
collected 18-20 days after treatment. No damage to sugarcane plants was seen in any of the
test plots. Weed species included false amaranth (Digera muricata, FA), giant pigweed
(Trianthema portullactastrum, GPW), Egyptian crowfoot grass (Dactylium aegyptium, ECG),

purple nutsedge (Cyperus rotundus, PN), common purslane (Portulaca oleracea, CP) and
field bindweed (Convolvulus arvensis, FBW).

[0042] As can be seen in the above table, the composition of Example 2 is equal to or
in many cases more active than the commercial standards.
Example 6: Control of Palmer Amaranth and Waterhemp With Fluthiacet-methyl and
Mesotrione Compositions
[0043] Compositions of the present disclosure were tested for herbicidal efficacy in
the following manner:
[0044] Test compositions containing Fluthiacet-methyl (Cadet® Herbicide),
mesotrione (15% SC formulation), mixtures of Cadet® Herbicide and mesotrione 15% SC
and the formulation of Example 1 were diluted with water to provide the appropriate test rate
concentrations. Test plots in Nebraska, Iowa, Kansas and Illinois were sprayed with the test
compositions to determine control of common waterhemp {Amaranthus rudis) in corn fields.
Test plots in Indiana and Kansas were sprayed with the test compositions to determine palmer
amaranth {Amaranthuspalmeri) control in corn crops. Test plots in Kansas, Illinois and
Nebraska were sprayed with the test compositions to determine morningglory
{Convolvulaceae sp.) control in corn crops.

[0045] Test solutions of the following were prepared: solutions of Example 2 applied
at 2.0, 2.5 and 3.15 ounces of the composition per acre, diluted in water; Cadet® Herbicide
was applied at 0.6 ounce of the formulation per acre, diluted in water; Callisto® Herbicide
applied at 2.37 ounces of the formulation per acre, diluted with water; A mixture of Cadet®
Herbicide applied at 0.6 ounce of the formulation per acre, diluted in water and Callisto®
Herbicide applied at 2.37 ounces of the formulation per acre, diluted with water; A mixture
of Example 2 at 2.5 ounces of the composition and 16 ounces of Atrazine 4L Flowable
Herbicide per acre, diluted with water. All test solutions contained l%v/v crop oil
concentrate. The average of the waterhemp evaluations and the palmer amaranth evaluations
are summarized in Table 4 below. The addition of atrazine to the composition of Example 2
increases the herbicidal activity substantially.

[0046] While this invention has been described with an emphasis upon preferred
embodiments, it will be obvious to those of ordinary skill in the art that variations in the
preferred compositions and methods can be used and that it is intended that the invention can
be practiced otherwise than as specifically described herein. Accordingly, this invention
includes all modifications encompassed within the spirit and scope of the invention as
defined by the claims that follow.

CLAIMS
What is claimed is:
1. A method for controlling weeds in a crop, comprising applying to weeds having an
average height ranging from about 4 inches to about 8 inches a herbicidally effective amount
of a composition comprising (a) fiuthiacet-methyl and (b) a p-hydroxyphenylpyruvate
dioxygenase (HPPD) inhibitor.
2. The method of claim 1, wherein the average height of the weeds is about 4 inches to
about 6 inches.
3. The method of claim 1, wherein the average height of the weeds is about 4 inches to
about 5 inches.
4. The method of claim 1, wherein the weeds comprise one or more selected from the
group consisting of waterhemp, lambsquarters, velvetleaf, palmer amaranth, pigweed,
morning glory, cocklebur, ragweed, broadleaf signalgrass, foxtail, crabgrass and volunteer
soybean.
5. The method of claim 1, wherein the crop is selected from the group consisting of corn
and sugarcane.
6. The method of claim 1, wherein the HPPD inhibitor is selected from the group
consisting of mesotrione, sulcotrione, nitisinine, tembotrione, topramezone, fenquinotrione,
ketospiradox and tefuryltrione.
7. The method of claim 6, wherein the HPPD inhibitor is mesotrione.
8. The method of claim 1, wherein the fiuthiacet-methyl and the HPPD inhibitor are
present in a ratio between about 1:2 and about 1:60.
9. The method of claim 1, wherein the fiuthiacet-methyl and the HPPD inhibitor are
present in a ratio between about 1:10 and about 1:40.

10. The method of claim 1, wherein the fluthiacet-methyl and the HPPD inhibitor are
present in a ratio between 1:15 and 1:35.
11." The method of claim 1, wherein the composition further comprises an additional crop
protection agent.
12. The method of claim 11, wherein the additional crop protection agent is selected from
the group consisting of atrazine, glyphosate, glufosinate, pyroxasulfone, dicamba,
diflufenzopyr, nicosuifuron, salts thereof, and mixtures of two or more thereof.
13. The method of claim 12, wherein said addition crop protection agent is atrazine.
14. A method for controlling weeds in a crop, comprising applying to weeds having an
average height ranging from about 4 inches to about 8 inches herbicidally effective amounts
of (a) fluthiacet-methyl and (b) a p-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitor.
15. The method of claim 14, further comprising applying an additional crop protection
agent.
16. The method of claim 15, wherein the additional crop protection agent is selected from
the group consisting of atrazine, glyphosate, glufosinate, pyroxasulfone, dicamba,
diflufenzopyr, nicosuifuron, salts thereof, and mixtures of two or more thereof.
17. The method of claim 16, wherein said addition crop protection agent is atrazine.
18. The method of claim 14, wherein said HPPD inhibitor is mesotrione.

ABSTRACT

Methods for controlling weeds in a crop by applying to weeds having an average
height ranging from about 4 inches to about 8 inches a herbicidally effective amount of a
composition that includes (a) fluthiacet-methyl and (b) a p-hydroxyphenylpyruvate
dioxygenase (HPPD) inhibitor are presented.