U.S. patent application number 13/786758 was filed with the patent office on 2014-01-30 for herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2- -carboxylic acid or a derivative thereof and a sulfonylaminocarbonyltriazolinone.
This patent application is currently assigned to Dow AgroSciences LLC. The applicant listed for this patent is Bryston L. Bangel, Norbert M. Satchivi. Invention is credited to Bryston L. Bangel, Norbert M. Satchivi.
Application Number | 20140031209 13/786758 |
Document ID | / |
Family ID | 49995426 |
Filed Date | 2014-01-30 |
United States Patent
Application |
20140031209 |
Kind Code |
A1 |
Satchivi; Norbert M. ; et
al. |
January 30, 2014 |
HERBICIDAL COMPOSITIONS COMPRISING
4-AMINO-3-CHLORO-5-FLUORO-6-(4-CHLORO-2-FLUORO-3-METHOXYPHENYL)PYRIDINE-2-
-CARBOXYLIC ACID OR A DERIVATIVE THEREOF AND A
SULFONYLAMINOCARBONYLTRIAZOLINONE
Abstract
A herbicidal composition containing (a) a compound of formula
(I): ##STR00001## or an agriculturally acceptable salt or ester
thereof and (b) a sulfonylaminocarbonyltriazone herbicide, or an
agriculturally acceptable salt or ester thereof.
Inventors: |
Satchivi; Norbert M.;
(Carmel, IN) ; Bangel; Bryston L.; (Camby,
IN) |
|
Applicant: |
Name |
City |
State |
Country |
Type |
Satchivi; Norbert M.
Bangel; Bryston L. |
Carmel
Camby |
IN
IN |
US
US |
|
|
Assignee: |
Dow AgroSciences LLC
Indianapolis
IN
|
Family ID: |
49995426 |
Appl. No.: |
13/786758 |
Filed: |
March 6, 2013 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
|
|
61674995 |
Jul 24, 2012 |
|
|
|
Current U.S.
Class: |
504/103 ;
504/130 |
Current CPC
Class: |
A01N 43/40 20130101;
A01N 43/653 20130101; A01N 43/40 20130101; A01N 47/38 20130101;
A01N 2300/00 20130101 |
Class at
Publication: |
504/103 ;
504/130 |
International
Class: |
A01N 43/40 20060101
A01N043/40; A01N 43/653 20060101 A01N043/653 |
Claims
1. A herbicidal composition comprising a herbicidally effective
amount of (a) a compound of the formula (I) ##STR00008## or an
agriculturally acceptable salt or ester thereof and (b) a
sulfonylaminocarbonyltriazone herbicide, or an agriculturally
acceptable salt or ester thereof.
2. The composition of claim 1, wherein (a) is a C.sub.1-4 alkyl or
benzyl ester of compound (I).
3. The composition of claim 2, wherein (a) is a benzyl ester of
compound (I).
4. The composition of claim 1, wherein (a) is the compound of
formula (I), which is the carboxylic acid.
5. The composition of any of claims 1-4, wherein the
sulfonylaminocarbonyltriazone herbicide is flucarbazone,
propoxycarbazone, thiencarbazone, or a salt or ester thereof.
6. The composition of claim 1, wherein (a) is the compound of
formula (I) or an agriculturally acceptable benzyl ester and (b)
flucarbazone or a salt or ester thereof.
7. The composition of claim 1, wherein (a) is the compound of
formula (I) or an agriculturally acceptable benzyl ester and (b)
propoxycarbazone or a salt or ester thereof.
8. The composition of any of claims 1-7, further comprising a
herbicide safener.
9. The composition of any of claims 1-8, wherein the weight ratio
of compound of formula (I) or agriculturally acceptable salt or
ester thereof to the sulfonylaminocarbonyltriazone herbicide or
agriculturally acceptable salt or ester thereof is from 5:1 to
1:256.
10. The composition of any of claims 1-8, wherein the weight ratio
of compound of formula (I) or agriculturally acceptable salt or
ester thereof to the sulfonylaminocarbonyltriazone herbicide or
agriculturally acceptable salt or ester thereof is from 2:1 to
1:2.
11. The composition of any of claims 1-10, further comprising an
agriculturally acceptable adjuvant or carrier.
12. The composition of any of claims 1-11, which is synergistic as
determined by the Colby equation.
13. A method of controlling undesirable vegetation comprising
contacting the undesirable vegetation or applying to the soil or
water adjacent thereto with the composition of any of claims
1-12.
14. The method of claim 13, wherein the undesirable vegetation is
controlled in cereal crops.
15. The method of claim 13, wherein the undesirable vegetation is
controlled in direct-seeded rice, water-seeded rice, transplanted
rice, wheat, barley, oats, rye, sorghum, corn or maize, soybean,
cotton, canola, oilseed rape, pastures, grasslands, rangelands,
fallowland, turf, tree and vine orchards, aquatics, or IVM.
16. The method of claim 13, wherein the undesirable vegetation is
controlled in glyphosate, glufosinate, dicamba, imidazolinone,
2,4-D, ALS, or ACC'ase tolerant crops.
17. The method of claim 13, wherein the contacting is a
post-emergence application, pre-emergence application, or in-water
application to flooded paddy rice or water bodies.
18. The method of claim 13, wherein the undesirable vegetation is
immature undesirable vegetation.
Description
[0001] This application claims the benefit of U.S. Provisional
Patent Application Ser. No. 61/674,995, filed Jul. 24, 2012.
BACKGROUND
[0002] The protection of crops from weeds and other vegetation
which inhibit crop growth is a constantly recurring problem in
agriculture. To help combat this problem, researchers in the field
of synthetic chemistry have produced an extensive variety of
chemicals and chemical formulations effective in the control of
such unwanted growth. Chemical herbicides of many types have been
disclosed in the literature and a large number are in commercial
use.
SUMMARY
[0003] Provided herein are herbicidal compositions comprising a
herbicidally effective amount of (a) a compound of the formula
(I)
##STR00002##
or an agriculturally acceptable salt or ester of thereof, and (b) a
sulfonylaminocarbonyltriazone herbicide, or an agriculturally
acceptable salt or ester thereof. The compositions may also contain
an agriculturally acceptable adjuvant or carrier.
[0004] Provided herein also are methods of controlling undesirable
vegetation comprising applying (a) a compound of formula (I) or an
agriculturally acceptable ester or salt thereof and (b) a
sulfonylaminocarbonyltriazone herbicide, or an agriculturally
acceptable salt or ester thereof.
DETAILED DESCRIPTION
Definitions
[0005] As used herein, the compound of formula (I) has the
following structure:
##STR00003##
The compound of formula (I) can be identified by the name
4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-
-carboxylic acid and has been described in U.S. Pat. No. 7,314,849
(B2), which is incorporated herein by reference in its entirety.
Exemplary uses of the compound of the formula (I) include
controlling undesirable vegetation, including grass, broadleaf and
sedge weeds, in multiple non-crop and cropping situations.
[0006] As used herein, the sulfonylaminocarbonyltriazolinone
herbicides inhibit the acetolactate synthetase enzyme, i.e., they
act by inhibiting biosynthesis of the essential amino acids
leucine, valine and isoleucine, thereby stopping cell division and
plant growth. Sulfonylaminocarbonyltriazolinones include, but are
not limited to flucarbazone, propoxycarbazone, thiencarbazone, and
salts or esters thereof.
[0007] As used herein, flucarbazone is
4,5-dihydro-3-methoxy-4-methyl-5-oxo-N-[[2-(trifluoromethoxy)phenyl]sulfo-
nyl]-1H-1,2,4-triazole-1-carboxamide and has the following
structure:
##STR00004##
Flucarbazone's herbicidal activity is exemplified in The Pesticide
Manual, Fifteenth Edition, 2009. Flucarbazone provides
post-emergence control of annual grass weeds and some perennial
grass weeds and some broad-leaved weeds.
[0008] As used herein, propoxycarbazone is methyl
2-[[[(4,5-dihydro-4-methyl-5-oxo-3-propoxy-1H-1,2,4-triazol-1-yl)carbonyl-
]amino]sulfonyl]benzoate and has the following structure:
##STR00005##
Propoxycarbazone's herbicidal activity is exemplified in The
Pesticide Manual, Fifteenth Edition, 2009. Propoxycarbazone
provides post-emergence control of grass weeds and some
broad-leaved weeds.
[0009] As used herein, thiencarbazone is
4-[[[(4,5-dihydro-3-methoxy-4-methyl-5-oxo-1H-1,2,4-triazol-1-yl)carbonyl-
]amino]sulfonyl]-5-methyl-3-thiophenecarboxylic acid and has the
following structure:
##STR00006##
Thiencarbazone's herbicidal activity is exemplified in The
Pesticide Manual, Fifteenth Edition, 2009. Thiencarbazone provides
post-emergence control of grass weeds and some broad-leaved
weeds.
[0010] As used herein, herbicide means an active ingredient that
kills, controls or otherwise adversely modifies the growth of
plants.
[0011] As used herein, a herbicidally effective or vegetation
controlling amount is an amount of active ingredient which causes
an adversely modifying effect and includes deviations from natural
development, killing, regulation, desiccation, retardation, and the
like.
[0012] As used herein, controlling undesirable vegetation means
preventing, reducing, killing, or otherwise adversely modifying the
development of plants and vegetation. Described herein are methods
of controlling undesirable vegetation through the application of
certain herbicide combinations or compositions. Methods of
application include, but are not limited to applications to the
vegetation or locus thereof, as well as preemergence,
postemergence, and foliar applications.
[0013] As used herein, plants and vegetation include, but are not
limited to, germinant seeds, emerging seedlings, plants emerging
from vegetative propagules, and established vegetation.
[0014] As used herein, agriculturally acceptable salts and esters
refer to salts and esters that exhibit herbicidal activity, or that
are or can be converted in plants, water, or soil to the referenced
herbicide. Exemplary agriculturally acceptable esters are those
that are or can by hydrolyzed, oxidized, metabolized, or otherwise
converted, e.g., in plants, water, or soil, to the corresponding
carboxylic acid which, depending on the pH, may be in the
dissociated or undissociated form. Exemplary salts include those
derived from alkali or alkaline earth metals and those derived from
ammonia and amines. Exemplary cations include sodium, potassium,
magnesium, and aminium cations of the formula:
R.sup.1R.sup.2R.sup.3R.sup.4N.sup.+
wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 each, independently
represents hydrogen or C.sub.1-C.sub.12 alkyl, C.sub.3-C.sub.12
alkenyl or C.sub.3-C.sub.12 alkynyl, each of which is optionally
substituted by one or more hydroxy, C.sub.1-C.sub.4 alkoxy,
C.sub.1-C.sub.4 alkylthio or phenyl groups, provided that R.sup.1,
R.sup.2, R.sup.3 and R.sup.4 are sterically compatible.
Additionally, any two of R.sup.1, R.sup.2, R.sup.3 and R.sup.4
together may represent an aliphatic difunctional moiety containing
one to twelve carbon atoms and up to two oxygen or sulfur atoms.
Salts can be prepared by treatment with a metal hydroxide, such as
sodium hydroxide, with an amine, such as ammonia, trimethylamine,
diethanolamine, 2-methylthiopropylamine, bisallylamine,
2-butoxyethylamine, morpholine, cyclododecylamine, or benzylamine
or with a tetraalkylammonium hydroxide, such as tetramethylammonium
hydroxide or choline hydroxide.
[0015] Exemplary esters include those derived from C.sub.1-C.sub.12
alkyl, C.sub.3-C.sub.12 alkenyl, C.sub.3-C.sub.12 alkynyl or
C.sub.7-C.sub.10 aryl-substituted alkyl alcohols, such as methyl
alcohol, isopropyl alcohol, 1-butanol, 2-ethylhexanol,
butoxyethanol, methoxypropanol, allyl alcohol, propargyl alcohol,
cyclohexanol or unsubstituted or substituted benzyl alcohols.
Benzyl alcohols may be substituted with from 1-3 substituents
independently selected from halogen, C.sub.1-C.sub.4 alkyl or
C.sub.1-C.sub.4 alkoxy. Esters can be prepared by coupling of the
acids with the alcohol using any number of suitable activating
agents such as those used for peptide couplings such as
dicyclohexylcarbodiimide (DCC) or carbonyl diimidazole (CDI); by
reacting the acids with alkylating agents such as alkylhalides or
alkylsulfonates in the presence of a base such as triethylamine or
lithium carbonate; by reacting the corresponding acid chloride of
an acid with an appropriate alcohol; by reacting the corresponding
acid with an appropriate alcohol in the presence of an acid
catalyst or by transesterification.
Compositions and Methods
[0016] Provided herein are herbicidal compositions comprising a
herbicidally effective amount of (a) a compound of the formula
(I)
##STR00007##
or an agriculturally acceptable salt or ester of thereof, and (b) a
sulfonylaminocarbonyltriazone herbicide, or an agriculturally
acceptable salt or ester thereof.
[0017] Provided herein also are methods of controlling undesirable
vegetation comprising contacting the vegetation or applying to the
soil or water adjacent thereto to prevent the emergence or growth
of vegetation a herbicidally effective amount of the compound of
formula (I) and (b) a sulfonylaminocarbonyltriazone herbicide, or
an agriculturally acceptable salt or ester thereof. The undesirable
vegetation can be immature undesirable vegetation. In certain
embodiments, the methods employ the compositions described
herein.
[0018] Furthermore, the combination of compound (I) or
agriculturally acceptable salt or ester thereof and a
sulfonylaminocarbonyltriazone herbicide, or an agriculturally
acceptable salt or ester thereof can exhibit synergism, i.e., the
herbicidal active ingredients are more effective in combination
than when applied individually. The Herbicide Handbook of the Weed
Science Society of America, Ninth Edition, 2007, p. 429 notes that
"`synergism` [is] an interaction of two or more factors such that
the effect when combined is greater than the predicted effect based
on the response of each factor applied separately." Certain
compositions described herein exhibit synergy as determined by the
Colby's equation. Colby, S. R., Calculation of the synergistic and
antagonistic response of herbicide combinations, Weeds 15:20-22,
1967.
[0019] The compound of formula (I) or an agriculturally acceptable
salt or ester thereof and a sulfonylaminocarbonyltriazone
herbicide, or an agriculturally acceptable salt or ester thereof,
e.g., flucarbazone, propoxycarbazone, thiencarbazone, or an
agriculturally acceptable salt or ester thereof, can be formulated
in one composition, tank mixed, applied simultaneously, or applied
sequentially.
[0020] Herbicidal activity is exhibited by the compounds when they
are applied directly to the plant or to the soil or water adjacent
the plant at any stage of growth. The effect observed depends upon
the plant species to be controlled, the stage of growth of the
plant, the application parameters of dilution and spray drop size,
the particle size of solid components, the environmental conditions
at the time of use, the specific compound employed, the specific
adjuvants and carriers employed, the soil type, and the like, as
well as the amount of chemical applied. These and other factors can
be adjusted to promote non-selective or selective herbicidal
action. The compositions described herein can be applied as a
post-emergence application, pre-emergence application, or in-water
application to flooded paddy rice or water bodies (e.g., ponds,
lakes and streams). Additionally, the compositions described herein
can be applied to relatively immature undesirable vegetation to
achieve the maximum control of weeds.
[0021] The compositions and methods provided herein can be used to
control weeds in crops, including but not limited to cereal crops,
direct-seeded, water-seeded and transplanted rice, wheat, durum,
barley, oats, rye, sorghum, triticale, corn/maize, soybean, cotton,
canola, oilseed rape, pastures, grasslands, rangelands, fallowland,
turf, tree and vine orchards, aquatics, and IVM, and also in
glyphosate, glufosinate, dicamba, imidazolinone, phenoxy auxin,
2,4-D, pyridyloxy auxin, aryloxyphenoxypropionate, acetyl CoA
carboxylase (ACCase), acetolactate synthase (ALS),
4-hydroxyphenyl-pyruvate dioxygenase (HPPD, protoporphyrinogen
oxidase (PPO), triazine, and bromoxynil tolerant crops (such as,
but not limited to, soybean, cotton, canola/oilseed rape, rice,
cereals, corn, turf, etc).
[0022] The compositions and methods provided herein can be used to
control undesirable vegetation consisting of grass, broadleaf and
sedge weeds. For example, the compositions and methods provided
herein can be used to control undesirable vegetation such as
Alopecurus, Bromus, Apera, Phalaris, Lolium, Avena, Setaria,
Pennisetum, Poa, and Echinochloa; broadleaf weeds such as Papaver,
Galium, Lamium, Kochia, Salsola, Matricaria, Veronica, Viola,
Capsella, Descurainia, Cirsium, Polygonum, Sinapis, Chenopodium,
Amaranthus, Aeschynomene, Sesbania, Centaurea, Stellaria, Anthemis,
Brassica, Raphanus, Euphorbia, Rapistrum, Convolvulus, Sonchus,
Geranium, Portulaca, Malva, Silene, and Monochoria; and sedge
species such as Cyperus and Scirpus.
[0023] For further example, the combination of compound (I) or
agriculturally acceptable ester or salt thereof and a
sulfonylaminocarbonyltriazone herbicide, or an agriculturally
acceptable salt or ester thereof can be used to control chickweed
(Stellaria media L; STEME), scented mayweed (Matricaria chamomila
L; MATCH), Canada thistle (Cirsium arvense L; CIRAR), bird's-eye
speedwell (Veronica persica L; VERPE), purple deadnettle (Lamium
purpureum L; LAMPU).
[0024] In the compounds and methods described herein, an
agriculturally acceptable ester or salt of compound (I) is
employed. An agriculturally acceptable ester, such as an aralkyl or
alkyl ester, can be employed. The ester can be a C.sub.1-4 alkyl
ester, a n-butyl ester, a benzyl ester, or a substituted benzyl
ester. Additionally, the carboxylic acid form of compound (I) or
the carboxylate salt of the compound of formula (I) can be
used.
[0025] In the compounds and methods described herein, an
agriculturally acceptable ester or salt of a
sulfonylaminocarbonyltriazone herbicide, e.g., flucarbazone,
propoxycarbazone, thiencarbazone, or a salt or ester thereof, can
be used. For example, the sodium salt of flucarbazone,
propoxycarbazone, or thiencarbazone can be used.
[0026] For example, the compound of formula (I) or an
agriculturally acceptable benzyl ester can be combined with
flucarbazone or a salt or ester thereof. For further example, the
compound of formula (I) or an agriculturally acceptable benzyl
ester can be combined with propoxycarbazone or a salt or ester
thereof.
[0027] In the compositions and methods described herein, the weight
ratio of the compound of formula (I) or salt or ester thereof to
the sulfonylaminocarbonyltriazone herbicide is within the range of
from 5:1 to 1:256. The weight ratio of the compound of formula (I)
or salt or ester thereof to the sulfonylaminocarbonyltriazone
herbicide also can be within the range of from 5:1 to 1:128, 5:1 to
1:64, 5:1 to 1:32, 5:1 to 1:24, 5:1 to 1:16, 5:1 to 1:14, 5:1 to
1:12, 5:1 to 1:10, 5:1 to 1:9, 5:1 to 1:8, 5:1 to 1:7, 5:1 to 1:6,
5:1 to 1:5, 5:1 to 1:4, 5:1 to 1:3, 5:1 to 1:2, or 5:1 to 1:1.
Additionally, the weight ratio of the compound of formula (I) or
salt or ester thereof to the sulfonylaminocarbonyltriazone
herbicide can be within the range of from 2:1 to 1:128, 2:1 to
1:64, 2:1 to 1:32, 2:1 to 1:24, 2:1 to 1:16, 2:1 to 1:14, 2:1 to
1:12, 2:1 to 1:10, 2:1 to 1:9, 2:1 to 1:8, 2:1 to 1:7, 2:1 to 1:6,
2:1 to 1:5, 2:1 to 1:4, 2:1 to 1:3, 2:1 to 1:2, or 2:1 to 1:1.
Further, the weight ratio of the compound of formula (I) or salt or
ester thereof to the sulfonylaminocarbonyltriazone herbicide can be
within the range of from 1.9:1 to 1:2, 1.8:1 to 1:2, 1.7:1 to 1:2,
1.6:1 to 1:2, 1.5:1 to 1:2, 1.4:1 to 1:2, 1.3:1 to 1:2, 1.2:1 to
1:2, 1.1:1 to 1:2, 1:1 to 1:2, 2:1 to 1:1.9, 2:1 to 1:1.8, 2:1 to
1:1.7, 2:1 to 1:1.6, 2:1 to 1:1.5, 2:1 to 1:1.4, 2:1 to 1:1.3, 2:1
to 1:1.2, or 2:1 to 1:1.1. Additionally, the weight ratio of the
compound of formula (I) or salt or ester thereof to the
sulfonylaminocarbonyltriazone herbicide can be 1:1, 1:2, 2:1, 1:3,
3:1, 1:4, 4:1, 1:5, 5:1, 9:8, or 9:15.
[0028] The application rate will depend upon the particular type of
weed to be controlled, the degree of control required, and the
timing and method of application. In general, the compositions as
described herein can be applied at an application rate of from 4
grams acid equivalent per hectare (g ae/ha) to 1200 g ae/ha based
on the total amount of active ingredients in the composition. The
composition as described herein also can be applied at an
application rate of from 4 g ae/ha to 1000 g ae/ha, 4 g ae/ha to
800 g ae/ha, 4 g ae/ha to 600 g ae/ha, 4 g ae/ha to 500 g ae/ha, 4
g ae/ha to 400 g ae/ha, 4 g ae/ha to 300 g ae/ha, 4 g ae/ha to 250
g ae/ha, 4 g ae/ha to 200 g ae/ha, 4 g ae/ha to 150 g ae/ha, 4 g
ae/ha to 100 g ae/ha, 4 g ae/ha to 90 g ae/ha, 4 g ae/ha to 80 g
ae/ha, 4 g ae/ha to 70 g ae/ha, 4 g ae/ha to 60 g ae/ha, 4 g ae/ha
to 50 g ae/ha, 4 g ae/ha to 40 g ae/ha, 4 g ae/ha to 30 g ae/ha, or
4 g ae/ha to 20 g ae/ha, 4 g ae/ha to 10 g ae/ha, 4 g ae/ha to 5 g
ae/ha, or 4 g ae/ha based on the total amount of active ingredients
in the composition.
[0029] The components of the mixtures described herein can be
applied either separately or as part of a multipart herbicidal
system.
[0030] The mixtures described herein can be applied in conjunction
with one or more other herbicides to control a wider variety of
undesirable vegetation. When used in conjunction with other
herbicides, the composition can be formulated with the other
herbicide or herbicides, tank mixed with the other herbicide or
herbicides or applied sequentially with the other herbicide or
herbicides. Some of the herbicides that can be employed in
conjunction with the compositions and methods described herein
include, but are not limited to: 4-CPA; 4-CPB; 4-CPP; 2,4-D; 2,4-D
choline salt, 2,4-D esters and amines, 2,4-DB; 3,4-DA; 3,4-DB;
2,4-DEB; 2,4-DEP; 3,4-DP; 2,3,6-TBA; 2,4,5-T; 2,4,5-TB; acetochlor,
acifluorfen, aclonifen, acrolein, alachlor, allidochlor, alloxydim,
allyl alcohol, alorac, ametridione, ametryn, amibuzin,
amicarbazone, amidosulfuron, aminocyclopyrachlor, aminopyralid,
amiprofos-methyl, amitrole, ammonium sulfamate, anilofos, anisuron,
asulam, atraton, atrazine, azafenidin, azimsulfuron, aziprotryne,
barban, BCPC, beflubutamid, benazolin, bencarbazone, benfluralin,
benfuresate, bensulfuron-methyl, bensulide, benthiocarb,
bentazon-sodium, benzadox, benzfendizone, benzipram, benzobicyclon,
benzofenap, benzofluor, benzoylprop, benzthiazuron, bicyclopyrone,
bifenox, bilanafos, bispyribac-sodium, borax, bromacil, bromobonil,
bromobutide, bromofenoxim, bromoxynil, brompyrazon, butachlor,
butafenacil, butamifos, butenachlor, buthidazole, buthiuron,
butralin, butroxydim, buturon, butylate, cacodylic acid,
cafenstrole, calcium chlorate, calcium cyanamide, cambendichlor,
carbasulam, carbetamide, carboxazole chlorprocarb,
carfentrazone-ethyl, CDEA, CEPC, chlomethoxyfen, chloramben,
chloranocryl, chlorazifop, chlorazine, chlorbromuron, chlorbufam,
chloreturon, chlorfenac, chlorfenprop, chlorflurazole,
chlorflurenol, chloridazon, chlorimuron, chlornitrofen, chloropon,
chlorotoluron, chloroxuron, chloroxynil, chlorpropham,
chlorsulfuron, chlorthal, chlorthiamid, cinidon-ethyl, cinmethylin,
cinosulfuron, cisanilide, clethodim, cliodinate,
clodinafop-propargyl, clofop, clomazone, clomeprop, cloprop,
cloproxydim, clopyralid, cloransulam-methyl, CMA, copper sulfate,
CPMF, CPPC, credazine, cresol, cumyluron, cyanatryn, cyanazine,
cycloate, cyclosulfamuron, cycloxydim, cycluron, cyhalofop-butyl,
cyperquat, cyprazine, cyprazole, cypromid, daimuron, dalapon,
dazomet, delachlor, desmedipham, desmetryn, di-allate, dicamba,
dichlobenil, dichloralurea, dichlormate, dichlorprop,
dichlorprop-P, diclofop-methyl, diclosulam, diethamquat, diethatyl,
difenopenten, difenoxuron, difenzoquat, diflufenican,
diflufenzopyr, dimefuron, dimepiperate, dimethachlor,
dimethametryn, dimethenamid, dimethenamid-P, dimexano, dimidazon,
dinitramine, dinofenate, dinoprop, dinosam, dinoseb, dinoterb,
diphenamid, dipropetryn, diquat, disul, dithiopyr, diuron, DMPA,
DNOC, DSMA, EBEP, eglinazine, endothal, epronaz, EPTC, erbon,
esprocarb, ethalfluralin, ethbenzamide, ethametsulfuron,
ethidimuron, ethiolate, ethobenzamid, etobenzamid, ethofumesate,
ethoxyfen, ethoxysulfuron, etinofen, etnipromid, etobenzanid, EXD,
fenasulam, fenoprop, fenoxaprop, fenoxaprop-P-ethyl,
fenoxaprop-P-ethyl+isoxadifen-ethyl, fenoxasulfone, fenteracol,
fenthiaprop, fentrazamide, fenuron, ferrous sulfate, flamprop,
flamprop-M, flazasulfuron, florasulam, fluazifop,
fluazifop-P-butyl, fluazolate, flucarbazone, flucetosulfuron,
fluchloralin, flufenacet, flufenican, flufenpyr-ethyl, flumetsulam,
flumezin, flumiclorac-pentyl, flumioxazin, flumipropyn,
fluometuron, fluorodifen, fluoroglycofen, fluoromidine,
fluoronitrofen, fluothiuron, flupoxam, flupropacil, flupropanate,
flupyrsulfuron, fluridone, fluorochloridone, fluoroxypyr,
flurtamone, fluthiacet, fomesafen, foramsulfuron, fosamine,
fumiclorac, furyloxyfen, glufosinate, glufosinate-ammonium,
glufosinate-P-ammonium, glyphosate, halosafen, halosulfuron-methyl,
haloxydine, haloxyfop-methyl, haloxyfop-P-methyl,
hexachloroacetone, hexaflurate, hexazinone, imazamethabenz,
imazamox, imazapic, imazapyr, imazaquin, imazosulfuron,
imazethapyr, indanofan, indaziflam, iodobonil, iodomethane,
iodosulfuron, iodosulfuron-ethyl-sodium, iofensulfuron, ioxynil,
ipazine, ipfencarbazone, iprymidam, isocarbamid, isocil,
isomethiozin, isonoruron, isopolinate, isopropalin, isoproturon,
isouron, isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop,
karbutilate, ketospiradox, lactofen, lenacil, linuron, MAA, MAMA,
MCPA esters and amines, MCPA-thioethyl, MCPB, mecoprop, mecoprop-P,
medinoterb, mefenacet, mefluidide, mesoprazine, mesosulfuron,
mesotrione, metam, metamifop, metamitron, metazachlor,
metazosulfuron, metflurazon, methabenzthiazuron, methalpropalin,
methazole, methiobencarb, methiozolin, methiuron, methometon,
methoprotryne, methyl bromide, methyl isothiocyanate, methyldymron,
metobenzuron, metobromuron, metolachlor, metosulam, metoxuron,
metribuzin, metsulfuron, metsulfuron-methyl, molinate, monalide,
monisouron, monochloroacetic acid, monolinuron, monuron,
morfamquat, MSMA, naproanilide, napropamide, naptalam, neburon,
nicosulfuron, nipyraclofen, nitralin, nitrofen, nitrofluorfen,
norflurazon, noruron, OCH, orbencarb, ortho-dichlorobenzene,
orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxapyrazon,
oxasulfuron, oxaziclomefone, oxyfluorfen, paraflufen-ethyl,
parafluoron, paraquat, pebulate, pelargonic acid, pendimethalin,
penoxsulam, pentachlorophenol, pentanochlor, pentoxazone,
perfluidone, pethoxamid, phenisopham, phenmedipham,
phenmedipham-ethyl, phenobenzuron, phenylmercury acetate, picloram,
picolinafen, pinoxaden, piperophos, potassium arsenite, potassium
azide, potassium cyanate, pretilachlor, primisulfuron-methyl,
procyazine, prodiamine, profluazol, profluralin, profoxydim,
proglinazine, prohexadione-calcium, prometon, prometryn, pronamide,
propachlor, propanil, propaquizafop, propazine, propham,
propisochlor, propoxycarbazone, propyrisulfuron, propyzamide,
prosulfalin, prosulfocarb, prosulfuron, proxan, prynachlor,
pydanon, pyraclonil, pyraflufen-ethyl, pyrasulfotole, pyrazogyl,
pyrazolynate, pyrazosulfuron-ethyl, pyrazoxyfen, pyribenzoxim,
pyributicarb, pyriclor, pyridafol, pyridate, pyriftalid,
pyriminobac, pyrimisulfan, pyrithiobac-sodium, pyroxasulfone,
pyroxsulam, quinclorac, quinmerac, quinoclamine, quinonamid,
quizalofop, quizalofop-P-ethyl, rhodethanil, rimsulfuron,
saflufenacil, S-metolachlor, sebuthylazine, secbumeton, sethoxydim,
siduron, simazine, simeton, simetryn, SMA, sodium arsenite, sodium
azide, sodium chlorate, sulcotrione, sulfallate, sulfentrazone,
sulfometuron, sulfosate, sulfosulfuron, sulfuric acid, sulglycapin,
swep, TCA, tebutam, tebuthiuron, tefuryltrione, tembotrione,
tepraloxydim, terbacil, terbucarb, terbuchlor, terbumeton,
terbuthylazine, terbutryn, tetrafluoron, thenylchlor,
thiazafluoron, thiazopyr, thidiazimin, thidiazuron,
thiencarbazone-methyl, thifensulfuron, thifensulfurn-methyl,
thiobencarb, tiocarbazil, tioclorim, topramezone, tralkoxydim,
triafamone, tri-allate, triasulfuron, triaziflam, tribenuron,
tribenuron-methyl, tricamba, triclopyr choline salt, triclopyr
esters and salts, tridiphane, trietazine, trifloxysulfuron,
trifluralin, triflusulfuron, trifop, trifopsime,
trihydroxytriazine, trimeturon, tripropindan, tritac tritosulfuron,
vernolate, xylachlor and salts, esters, optically active isomers
and mixtures thereof.
[0031] The compositions and methods described herein also can be
used in conjunction with glyphosate, glufosinate, dicamba, phenoxy
auxins, pyridyloxy auxins, aryloxyphenoxypropionates, acetyl CoA
carboxylase (ACCase) inhibitors, imidazolinones, acetolactate
synthase (ALS) inhibitors, 4-hydroxyphenyl-pyruvate dioxygenase
(HPPD) inhibitors, protoporphyrinogen oxidase (PPO) inhibitors,
triazines, and bromoxynil on glyphosate-tolerant,
glufosinate-tolerant, dicamba-tolerant, phenoxy auxin-tolerant,
pyridyloxy auxin-tolerant, aryloxyphenoxypropionate-tolerant,
ACCase-tolerant, imidazolinone-tolerant, ALS-tolerant,
HPPD-tolerant, PPO-tolerant, triazine-tolerant,
bromoxynil-tolerant, and crops possessing multiple or stacked
traits conferring tolerance to multiple chemistries and/or multiple
modes of action. The compound of formula (I) or salt or ester
thereof and complementary herbicide or salt or ester thereof can be
used in combination with herbicides that are selective for the crop
being treated and which complement the spectrum of weeds controlled
by these compounds at the application rate employed. The
compositions described herein and other complementary herbicides
can be applied at the same time, either as a combination
formulation or as a tank mix.
[0032] The compositions described herein can be employed in
combination with one or more herbicide safeners, such as AD-67 (MON
4660), benoxacor, benthiocarb, brassinolide, cloquintocet (mexyl),
cyometrinil, daimuron, dichlormid, dicyclonon, dimepiperate,
disulfoton, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim,
furilazole, harpin proteins, isoxadifen-ethyl, jiecaowan, jiecaoxi,
mefenpyr-diethyl, mephenate, naphthalic anhydride (NA),
oxabetrinil, R29148 and N-phenyl-sulfonylbenzoic acid amides, to
enhance their selectivity. The safener can be cloquintocet or an
ester or salt thereof, such as cloquintocet (mexyl). Cloquintocet
can be used to antagonize harmful effects of the compositions on
rice and cereals.
[0033] The compositions provided herein can further include at
least one agriculturally acceptable adjuvant or carrier. Suitable
adjuvants or carriers should not be phytotoxic to valuable crops,
particularly at the concentrations employed in applying the
compositions for selective weed control in the presence of crops,
and should not react chemically with herbicidal components or other
composition ingredients. Such mixtures can be designed for
application directly to weeds or their locus or can be concentrates
or formulations that are normally diluted with additional carriers
and adjuvants before application. They can be solids, such as, for
example, dusts, granules, water-dispersible granules, or wettable
powders, or liquids, such as, for example, emulsifiable
concentrates, solutions, emulsions or suspensions. They can also be
provided as a pre-mix or tank mixed.
[0034] Suitable agricultural adjuvants and carriers include, but
are not limited to, crop oil concentrate; nonylphenol ethoxylate;
benzylcocoalkyldimethyl quaternary ammonium salt; blend of
petroleum hydrocarbon, alkyl esters, organic acid, and anionic
surfactant; C.sub.9-C.sub.11 alkylpolyglycoside; phosphated alcohol
ethoxylate; natural primary alcohol (C.sub.12-C.sub.16) ethoxylate;
di-sec-butylphenol EO-PO block copolymer; polysiloxane-methyl cap;
nonylphenol ethoxylate+urea ammonium nitrate; emulsified methylated
seed oil; tridecyl alcohol (synthetic) ethoxylate (8EO); tallow
amine ethoxylate (15 EO); PEG(400) dioleate-99.
[0035] Liquid carriers that can be employed include water and
organic solvents. The organic solvents include, but are not limited
to, petroleum fractions or hydrocarbons such as mineral oil,
aromatic solvents, paraffinic oils, and the like; vegetable oils
such as soybean oil, rapeseed oil, olive oil, castor oil, sunflower
seed oil, coconut oil, corn oil, cottonseed oil, linseed oil, palm
oil, peanut oil, safflower oil, sesame oil, tung oil and the like;
esters of the above vegetable oils; esters of monoalcohols or
dihydric, trihydric, or other lower polyalcohols (4-6 hydroxy
containing), such as 2-ethyl hexyl stearate, n-butyl oleate,
isopropyl myristate, propylene glycol dioleate, di-octyl succinate,
di-butyl adipate, di-octyl phthalate and the like; esters of mono,
di and polycarboxylic acids and the like. Specific organic solvents
include, but are not limited to toluene, xylene, petroleum naphtha,
crop oil, acetone, methyl ethyl ketone, cyclohexanone,
trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate,
butyl acetate, propylene glycol monomethyl ether and diethylene
glycol monomethyl ether, methyl alcohol, ethyl alcohol, isopropyl
alcohol, amyl alcohol, ethylene glycol, propylene glycol,
glycerine, N-methyl-2-pyrrolidinone, N,N-dimethyl alkylamides,
dimethyl sulfoxide, liquid fertilizers and the like. Water can be
the carrier for the dilution of concentrates.
[0036] Suitable solid carriers include but are not limited to talc,
pyrophyllite clay, silica, attapulgus clay, kaolin clay,
kieselguhr, chalk, diatomaceous earth, lime, calcium carbonate,
bentonite clay, Fuller's earth, cottonseed hulls, wheat flour,
soybean flour, pumice, wood flour, walnut shell flour, lignin,
cellulose, and the like.
[0037] The compositions described herein further can include one or
more surface-active agents. Such surface-active agents are employed
in both solid and liquid compositions, and in certain embodiments
those designed to be diluted with carrier before application. The
surface-active agents can be anionic, cationic or nonionic in
character and can be employed as emulsifying agents, wetting
agents, suspending agents, or for other purposes. Surfactants which
may also be used in the present formulations are described, inter
alia, in "McCutcheon's Detergents and Emulsifiers Annual," MC
Publishing Corp., Ridgewood, N.J., 1998 and in "Encyclopedia of
Surfactants," Vol. I-III, Chemical Publishing Co., New York,
1980-81. Surface-active agents include, but are not limited to
salts of alkyl sulfates, such as diethanolammonium lauryl sulfate;
alkylarylsulfonate salts, such as calcium dodecylbenzenesulfonate;
alkylphenol-alkylene oxide addition products, such as
nonylphenol-C.sub.18 ethoxylate; alcohol-alkylene oxide addition
products, such as tridecyl alcohol-C.sub.16 ethoxylate; soaps, such
as sodium stearate; alkylnaphthalene-sulfonate salts, such as
sodium dibutylnaphthalenesulfonate; dialkyl esters of
sulfosuccinate salts, such as sodium di(2-ethylhexyl)
sulfosuccinate; sorbitol esters, such as sorbitol oleate;
quaternary amines, such as lauryl trimethylammonium chloride;
polyethylene glycol esters of fatty acids, such as polyethylene
glycol stearate; block copolymers of ethylene oxide and propylene
oxide; salts of mono and dialkyl phosphate esters; vegetable or
seed oils such as soybean oil, rapeseed/canola oil, olive oil,
castor oil, sunflower seed oil, coconut oil, corn oil, cottonseed
oil, linseed oil, palm oil, peanut oil, safflower oil, sesame oil,
tung oil and the like; and esters of the above vegetable oils, and
in certain embodiments, methyl esters.
[0038] These materials, such as vegetable or seed oils and their
esters, can be used interchangeably as an agricultural adjuvant, as
a liquid carrier or as a surface active agent.
[0039] Other exemplary additives for use in the compositions
provided herein include but are not limited to compatibilizing
agents, antifoam agents, sequestering agents, neutralizing agents
and buffers, corrosion inhibitors, dyes, odorants, spreading
agents, penetration aids, sticking agents, dispersing agents,
thickening agents, freezing point depressants, antimicrobial
agents, and the like. The compositions may also contain other
compatible components, for example, other herbicides, plant growth
regulants, fungicides, insecticides, and the like and can be
formulated with liquid fertilizers or solid, particulate fertilizer
carriers such as ammonium nitrate, urea and the like.
[0040] The concentration of active ingredients in the compositions
described herein is generally from 0.0005 to 98 percent by weight.
Additionally, concentration is from 0.0006 to 90 percent by weight
can be used. In compositions designed to be employed as
concentrates, the active ingredients, can be present in a
concentration from 0.1 to 98 weight percent, or from 0.5 to 90
weight percent. Such compositions can be diluted with an inert
carrier, such as, for example, water, before application. The
diluted compositions usually applied to vegetation or the soil or
water adjacent thereto can contain from 0.0006 to 15.0 weight
percent active ingredient or from 0.001 to 10.0 weight percent.
[0041] The present compositions can be applied to weeds or to the
soil or water adjacent the weeds by use of conventional ground or
aerial dusters, sprayers, and granule applicators, by addition to
irrigation or paddy water, and by other conventional means known to
those skilled in the art.
[0042] The described compositions and methods and following
examples are for illustrative purposes and are not intended to
limit the scope of the claims. Other modifications, uses, or
combinations with respect to the compositions and methods described
herein will be apparent to a person of ordinary skill in the art
without departing from the spirit and scope of the claimed subject
matter.
EXAMPLES
Evaluation of Postemergence Herbicidal Activity of Mixtures in
Cereal Crops
[0043] Seeds of the desired test plant species were planted in Sun
Gro MetroMix 306 planting mixture, which typically has a pH of 6.0
to 6.8 and an organic matter content of about 30 percent, in
plastic pots with a surface area of 103.2 square centimeters
(cm.sup.2). When required to ensure good germination and healthy
plants, a fungicide treatment and/or other chemical or physical
treatment was applied. The plants were grown for 7-36 days in a
greenhouse with an approximate 14 hour photoperiod which was
maintained at about 18.degree. C. during the day and 17.degree. C.
during the night. Nutrients and water were added on a regular basis
and supplemental lighting was provided with overhead metal halide
1000-Watt lamps as necessary. The plants were employed for testing
when they reached the second or third true leaf stage.
[0044] Treatments consisted of the benzyl ester of the compound of
formula (I) (Compound A as listed in Tables 1-8) and a second
cereal herbicide alone and in combination. Specifically, weighed
amounts of Compound A (the benzyl ester of
4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-
-carboxylic acid) were placed in 25 milliliter (mL) glass vials and
dissolved in a volume of 97:3 v/v acetone/DMSO to obtain 4.5
milligrams (mg) active ingredient (ai)/mL stock solutions. If the
experimental compound did not dissolve readily, the mixture was
warmed and/or sonicated. The concentrated stock solutions were
diluted to 1.5 mg ai/mL with the addition of 2 volumes of an
aqueous mixture containing acetone, water, isopropyl alcohol, DMSO,
Agri-dex crop oil concentrate, and Triton.RTM. X-77 surfactant in a
64.7:26.0:6.7:2.0:0.7:0.01 v/v ratio. A dilution solution was
prepared by mixing 1 volume of 97:3 v/v acetone/DMSO and 2 volumes
of an aqueous mixture containing acetone, water, isopropyl alcohol,
DMSO, Agri-dex crop oil concentrate, and Triton.RTM. X-77
surfactant in a 64.7:26.0:6.7:2.0:0.7:0.01 v/v ratio. Compound
requirements are based upon a 12 mL application volume at a rate of
187 liters per hectare (L/ha). Spray solutions of the second cereal
herbicide and experimental compound mixtures were prepared by
adding the stock solutions to the appropriate amount of dilution
solution to form 12 mL spray solution with active ingredients in
two- and three-way combinations. Formulated compounds were applied
to the plant material with an overhead Mandel track sprayer
equipped with 8002E nozzles calibrated to deliver 187 L/ha over an
application area of 0.503 square meters (m.sup.2) at a spray height
of 18 inches (43 cm) above average plant canopy. Control plants
were sprayed in the same manner with the solvent blank.
[0045] The treated plants and control plants were placed in a
greenhouse as described above and watered by sub-irrigation to
prevent wash-off of the test compounds. After 20-22 days, the
condition of the test plants as compared with that of the control
plants was determined visually and scored on a scale of 0 to 100
percent where 0 corresponds to no injury and 100 corresponds to
complete kill.
[0046] Colby's equation was used to determine the herbicidal
effects expected from the mixtures (Colby, S. R. 1967. Calculation
of the synergistic and antagonistic response of herbicide
combinations. Weeds 15:20-22.). Specifically, the following
equation was used to calculate the expected activity of mixtures
containing two active ingredients, A and B:
Expected=A+B-(A.times.B/100) [0047] A=observed efficacy of active
ingredient A at the same concentration as used in the mixture.
[0048] B=observed efficacy of active ingredient B at the same
concentration as used in the mixture.
[0049] Details of the compounds tested, application rates employed,
plant species tested, and results are given in Table 1, Table 2,
Table 3, Table 4, Table 5, Table 6, Table 7, and Table 8.
TABLE-US-00001 TABLE 1 Synergistic Activity of Foliar-Applied
Compound A Benzyl ester and Flucarbazone-sodium Herbicidal
Compositions on Weed Control in a Cereal Cropping System
Application Rate (g/ha) VERPE STEME MATCH CIRAR Compound A
Flucarbazone-Na Obs Exp Obs Exp Obs Exp Obs Exp 8.75 0 50 -- 68 --
20 -- 40 -- 0 7.5 0 -- 60 -- 30 -- 50 -- 8.75 7.5 55 50 93 87 63 44
78 70 VERPE = Veronica persica STEME = Stellaria media MATCH =
Matricaria chamomila CIRAR = Cirsium arvense
TABLE-US-00002 TABLE 2 Synergistic Activity of Foliar-Applied
Compound A Benzyl ester and Flucarbazone-sodium Herbicidal
Compositions on Weed Control in a Cereal Cropping System
Application Rate (g/ha) Compound Flucarbazone- ALOMY APESV LOLMG A
Na Obs Exp Obs Exp Obs Exp 5 0 0 -- 0 -- 0 -- 10 0 0 -- 0 -- 0 -- 0
3.75 8 -- 33 -- 0 -- 0 7.5 17 -- 75 -- 0 -- 5 3.75 18 8 52 33 0 0
10 3.75 23 8 48 33 7 0 5 7.5 13 17 73 75 57 0 10 7.5 17 17 85 75 37
0 ALOMY = Alopecurus myosuroides APESV = Apera spica-venti LOLMG =
Lolium multiflorum subsp. gaudini
TABLE-US-00003 TABLE 3 Synergistic Activity of Foliar-Applied
Compound A Benzyl ester and Flucarbazone-sodium Herbicidal
Compositions on Weed Control in a Cereal Cropping System
Application Rate (g ai/ha) TRZAW STEME PAPRH SASKR MATCH VERPE
VIOTR Compound A Flucarbazone-Na Obs Exp Obs Exp Obs Exp Obs Exp
Obs Exp Obs Exp Obs Exp 5 0 7 -- 50 -- 46 -- 75 -- 20 -- 13 -- 27
-- 10 0 7 -- 63 -- 48 -- 78 -- 40 -- 25 -- 37 -- 0 3.75 2 -- 3 -- 0
-- 10 -- 10 -- 0 -- 7 -- 0 7.5 7 -- 7 -- 0 -- 7 -- 10 -- 0 -- 7 --
5 3.75 5 8 55 52 20 46 87 78 30 28 17 13 23 32 10 3.75 12 8 73 65
78 48 92 81 60 46 5 7.5 12 13 58 53 53 46 87 77 50 28 30 13 55 32
10 7.5 10 13 91 66 77 48 87 80 79 46 30 25 55 41 TRZAW = Triticum
aestivum STEME = Stellaria media PAPRH = Papaver rhoeas SASKR =
Alopecurus myosuroides MATCH = Apera spica-venti VERPE = Veronica
persica VIOTR = Viola tricolor
TABLE-US-00004 TABLE 4 Synergistic Activity of Foliar-Applied
Compound A Benzyl ester and Propoxycarbazone-sodium Herbicidal
Compositions on Weed Control in a Cereal Cropping System
Application Rate (g/ha) Com- pound Propoxycarbazone- LAMPU STEME
CIRAR A Na Obs Exp Obs Exp Obs Exp 8.75 0 83 -- 68 -- 40 -- 0 15 0
-- 45 -- 65 -- 8.75 15 93 83 90 82 95 79 LAMPU = Lamium purpureum
STEME = Stellaria media CIRAR = Cirsium arvense
TABLE-US-00005 TABLE 5 Synergistic Activity of Foliar-Applied
Compound A Benzyl ester and Propoxycarbazone-sodium Herbicidal
Compositions on Weed Control in a Cereal Cropping System
Application Rate (g ha) ALOMY APESV SETVI LOLMG Compound A
Propoxycarbazone-Na Obs Exp Obs Exp Obs Exp Obs Exp 5 0 0 -- 0 -- 0
-- 0 -- 10 0 0 -- 0 -- 0 -- 0 -- 0 7.5 10 -- 17 -- 0 -- 3 -- 0 15
43 -- 23 -- 0 -- 20 -- 5 7.5 15 10 22 17 13 0 7 3 10 7.5 15 10 27
17 23 0 13 3 5 15 47 43 22 23 20 0 13 20 10 15 50 43 32 23 33 0 20
20 ALOMY = Alopecurus myosuroides APESV = Apera spica-venti LOLMG =
Lolium multiflorum subsp. gaudini SETVI = Setaria viridis
TABLE-US-00006 TABLE 6 Synergistic Activity of Foliar-Applied
Compound A Benzyl ester and Propoxycarbazone-sodium Herbicidal
Compositions on Weed Control in a Cereal Cropping System
Application Rate (g ai/ha) TRZAW STEME PAPRH KCHSC MATCH VIOTR
Compound A Propoxycarbazone-Na Obs Exp Obs Exp Obs Exp Obs Exp Obs
Exp Obs Exp 5 0 7 -- 50 -- 46 -- 60 -- 20 -- 27 -- 10 0 7 -- 63 --
48 -- 57 -- 40 -- 37 -- 0 7.5 8 -- 12 -- 18 -- 13 -- 13 -- 13 -- 0
15 5 -- 10 -- 23 -- 25 -- 20 -- 23 -- 5 7.5 8 14 73 56 75 55 75 65
88 30 63 36 10 7.5 12 14 80 68 85 58 78 62 94 48 65 45 5 15 10 11
67 55 73 58 63 70 93 36 60 44 10 15 10 11 80 67 80 60 79 68 85 52
68 51 TRZAW = Triticum aestivum STEME = Stellaria media PAPRH =
Papaver rhoeas KCHSC = Kochia scoparia MATCH = Apera spica-venti
VIOTR = Viola tricolor
TABLE-US-00007 TABLE 7 Synergistic Activity of Foliar-Applied
Compound A Benzyl ester and Thiencarbazone-methyl Herbicidal
Compositions on Weed Control in a Cereal Cropping System
Application Rate (g ha) Thiencarbazone- TRZAS HORVS LAMPU GALAP
CHEAL Compound A methyl Obs Exp Obs Exp Obs Exp Obs Exp Obs Exp 2.5
0 0 -- 0 -- 80 -- 60 -- 50 -- 5 0 5 -- 0 -- 80 -- 60 -- 60 -- 0 2.5
0 -- 0 -- 10 -- 20 -- 10 -- 2.5 2.5 0 0 0 0 90 68 90 68 70 55 5 2.5
0 5 0 0 95 68 98 68 80 64 TRZAS = Triticum aestivum HORVS = Hordeum
vulgare LAMPU = Lamium purpureum GALAP = Galium aparine CHEAL =
Chenopodium album
TABLE-US-00008 TABLE 8 Synergistic Activity of Foliar-Applied
Compound A Benzyl ester and Thiencarbazone-methyl Herbicidal
Compositions on Weed Control in a Cereal Cropping System
Application Rate (g ha) Thiencarbazone- KCHSC SASKR VIOTR MATCH
CIRAR Compound A methyl Obs Exp Obs Exp Obs Exp Obs Exp Obs Exp 2.5
0 20 -- 10 -- 10 -- 0 -- 10 -- 5 0 40 -- 60 -- 10 -- 10 -- 20 -- 0
2.5 0 -- 10 -- 10 -- 10 -- 0 -- 2.5 2.5 70 20 70 19 70 19 90 10 30
10 5 2.5 65 40 80 64 60 19 80 19 40 20 KCHSC = Kochia scoparia (L.)
Schrad. SASKR = Salsola tragus VIOTR = Viola tricolor MATCH =
Matricaria chamomila CIRAR = Cirsium arvense
* * * * *