U.S. patent application number 13/840236 was filed with the patent office on 2014-09-18 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 fungicides.
The applicant listed for this patent is DOW AGROSCIENCES LLC. Invention is credited to Richard K. Mann, Carla N. Yerkes.
Application Number | 20140274697 13/840236 |
Document ID | / |
Family ID | 51529779 |
Filed Date | 2014-09-18 |
United States Patent
Application |
20140274697 |
Kind Code |
A1 |
Mann; Richard K. ; et
al. |
September 18, 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
FUNGICIDES
Abstract
Provided herein are synergistic herbicidal compositions
containing (a) a compound of formula (I): ##STR00001## or an
agriculturally acceptable salt or ester thereof and (b) fungicides,
including but not limited to, azoxystrobin, carbendazim,
difenoconazole, flutolanil, hexaconazole, iprobenfos,
isoprothiolane, isotianil, kasugamycin, mancozeb, myclobutanil,
phthalide, probenazole, propiconazole, pyroquilon, tebuconazole,
thifluzamide, tricyclazole, trifloxystrobin, validamycin, and a
compound of formula (II) ##STR00002## The compositions and methods
provided herein control undesirable vegetation, e.g., in
direct-seeded, water-seeded and transplanted rice, cereals, wheat,
barley, oats, rye, sorghum, corn/maize, sugarcane, sunflower,
oilseed rape, canola, sugar beet, soybean, cotton, pineapple,
pastures, grasslands, rangelands, fallowland, turf, tree and vine
orchards, plantation crops, vegetables, industrial vegetation
management (IVM) and rights of way (ROW).
Inventors: |
Mann; Richard K.; (Franklin,
IN) ; Yerkes; Carla N.; (Crawfordsville, IN) |
|
Applicant: |
Name |
City |
State |
Country |
Type |
DOW AGROSCIENCES LLC; |
|
|
US |
|
|
Family ID: |
51529779 |
Appl. No.: |
13/840236 |
Filed: |
March 15, 2013 |
Current U.S.
Class: |
504/103 ;
504/126; 504/127; 504/130; 504/136 |
Current CPC
Class: |
A01N 43/40 20130101;
A01N 43/40 20130101; A01N 37/24 20130101; A01N 37/50 20130101; A01N
43/12 20130101; A01N 43/16 20130101; A01N 43/28 20130101; A01N
43/54 20130101; A01N 43/653 20130101; A01N 43/78 20130101; A01N
43/80 20130101; A01N 43/90 20130101; A01N 47/14 20130101; A01N
47/18 20130101; A01N 57/14 20130101 |
Class at
Publication: |
504/103 ;
504/130; 504/136; 504/127; 504/126 |
International
Class: |
A01N 43/40 20060101
A01N043/40; A01N 57/14 20060101 A01N057/14; A01N 43/653 20060101
A01N043/653; A01N 43/90 20060101 A01N043/90; A01N 43/52 20060101
A01N043/52; A01N 43/54 20060101 A01N043/54; A01N 55/02 20060101
A01N055/02 |
Claims
1. A herbicidal composition comprising a herbicidally effective
amount of (a) a compound of the formula (I) ##STR00034## or an
agriculturally acceptable salt or ester thereof and (b)
azoxystrobin, carbendazim, difenoconazole, flutolanil,
hexaconazole, iprobenfos, isoprothiolane, isotianil, kasugamycin,
mancozeb, myclobutanil, phthalide, probenazole, propiconazole,
pyroquilon, tebuconazole, thifluzamide, tricyclazole,
trifloxystrobin, validamycin, and a compound of formula (II)
##STR00035##
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 1, wherein (a) is a C.sub.1-4 alkyl
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 claim 1, further comprising at least one
compound selected from the group consisting of: herbicide safeners,
carriers and adjuvants.
6. The composition of claim 1, wherein the weight ratio of compound
of formula (I) or agriculturally acceptable salt or ester thereof
to a compound of formula (II) is from about 1:375 to about
150:1.
7. A method of controlling undesirable vegetation which comprises
contacting the vegetation or the area adjacent to the vegetation
with or applying to the soil or water to prevent the emergence or
growth of vegetation a herbicidally effective amount of (a) a
compound of the formula (I) ##STR00036## or an agriculturally
acceptable salt or ester thereof and (b) azoxystrobin, carbendazim,
difenoconazole, flutolanil, hexaconazole, iprobenfos,
isoprothiolane, isotianil, kasugamycin, mancozeb, myclobutanil,
phthalide, probenazole, propiconazole, pyroquilon, tebuconazole,
thifluzamide, tricyclazole, trifloxystrobin, validamycin, and a
compound of formula (II) ##STR00037##
8. The method of claim 7, wherein the undesirable vegetation is
controlled in direct-seeded, water-seeded and transplanted rice,
cereals, wheat, barley, oats, rye, sorghum, corn/maize, sugarcane,
sunflower, oilseed rape, canola, sugar beet, soybean, cotton,
pineapple, pastures, grasslands, rangelands, fallowland, turf, tree
and vine orchards, plantation crops, vegetables, industrial
vegetation management (IVM) and rights of way (ROW).
9. The method of claim 7, wherein the undesirable vegetation is
immature.
10. The method of claim 7, wherein the (a) and (b) are applied to
water.
11. The method of claim 10, wherein the water is part of a flooded
rice paddy.
12. The method of claim 7, wherein the (a) and (b) are applied
pre-emergently and/or post emergently to the weed or the crop.
13. The method of claim 7, wherein the (a) and (b) are applied
post-emergently to the weed or the crop.
14. The method of claim 7, wherein the undesirable vegetation is
controlled in glyphosate-, 5-enolpyruvylshikimate-3-phosphate
(EPSP) synthase inhibitor-, glufosinate-, glutamine synthetase
inhibitor-, dicamba-, phenoxy auxin-, pyridyloxy auxin-, synthetic
auxin-, auxin transport inhibitor-, aryloxyphenoxypropionate-,
cyclohexanedione-, phenylpyrazoline-, acetyl CoA carboxylase
(ACCase) inhibitor-, imidazolinone-, sulfonylurea-,
pyrimidinylthiobenzoate-, triazolopyrimidine-,
sulfonylaminocarbonyltriazolinone-, acetolactate synthase (ALS) or
acetohydroxy acid synthase (AHAS) inhibitor-,
4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitor-, phytoene
desaturase inhibitor-, carotenoid biosynthesis inhibitor-,
protoporphyrinogen oxidase (PPO) inhibitor-, cellulose biosynthesis
inhibitor-, mitosis inhibitor-, microtubule inhibitor-, very long
chain fatty acid inhibitor-, fatty acid and lipid biosynthesis
inhibitor-, photosystem I inhibitor-, photosystem II inhibitor-,
triazine-, or bromoxynil-tolerant crops.
15. The method of claim 14, wherein the tolerant crop possesses
multiple or stacked traits conferring tolerance to multiple
herbicides or multiple modes of action.
16. The method of claim 7, wherein the undesirable vegetation
comprises a herbicide resistant or tolerant weed.
17. The method of claim 16, wherein the resistant or tolerant weed
is a biotype with resistance or tolerance to multiple herbicides,
multiple chemical classes, multiple herbicide modes-of-action or
via multiple resistance mechanisms.
18. The method of claim 16, wherein the resistant or tolerant weed
is a biotype resistant or tolerant to acetolactate synthase (ALS)
or acetohydroxy acid synthase (AHAS) inhibitors, photosystem II
inhibitors, acetyl CoA carboxylase (ACCase) inhibitors, synthetic
auxins, auxin transport inhibitors, photosystem I inhibitors,
5-enolpyruvylshikimate-3-phosphate (EPSP) synthase inhibitors,
microtubule assembly inhibitors, fatty acid and lipid synthesis
inhibitors, protoporphyrinogen oxidase (PPO) inhibitors, carotenoid
biosynthesis inhibitors, very long chain fatty acid (VLCFA)
inhibitors, phytoene desaturase (PDS) inhibitors, glutamine
synthetase inhibitors, 4-hydroxyphenyl-pyruvate-dioxygenase (HPPD)
inhibitors, mitosis inhibitors, cellulose biosynthesis inhibitors,
herbicides with multiple modes-of-action, quinclorac,
arylaminopropionic acids, difenzoquat, endothall, or
organoarsenicals.
19. The method of claim 17, wherein the resistant or tolerant weed
is a biotype resistant or tolerant to acetolactate synthase (ALS)
or acetohydroxy acid synthase (AHAS) inhibitors, photosystem II
inhibitors, acetyl CoA carboxylase (ACCase) inhibitors, synthetic
auxins, auxin transport inhibitors, photosystem I inhibitors,
5-enolpyruvylshikimate-3-phosphate (EPSP) synthase inhibitors,
microtubule assembly inhibitors, fatty acid and lipid synthesis
inhibitors, protoporphyrinogen oxidase (PPO) inhibitors, carotenoid
biosynthesis inhibitors, very long chain fatty acid (VLCFA)
inhibitors, phytoene desaturase (PDS) inhibitors, glutamine
synthetase inhibitors, 4-hydroxyphenyl-pyruvate-dioxygenase (HPPD)
inhibitors, mitosis inhibitors, cellulose biosynthesis inhibitors,
herbicides with multiple modes-of-action, quinclorac,
arylaminopropionic acids, difenzoquat, endothall, or
organoarsenicals.
Description
FIELD
[0001] Provided herein are compositions comprising (a)
4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl)
pyridine-2-carboxylic acid or an agriculturally acceptable ester or
salt thereof and (b) fungicides. Provided herein are also methods
of controlling undesirable vegetation comprising applying (a)
4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-
-carboxylic acid or an agriculturally acceptable ester or salt
thereof and (b) fungicides.
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. However, there remains a need for compositions and methods
that are effective in controlling undesirable vegetation.
SUMMARY
[0003] A first embodiment including a herbicidal composition
comprising a herbicidally effective amount of (a) a compound of the
formula (I)
##STR00003##
or an agriculturally acceptable salt or ester thereof and (b)
azoxystrobin, carbendazim, difenoconazole, flutolanil,
hexaconazole, iprobenfos, isoprothiolane, isotianil, kasugamycin,
mancozeb, myclobutanil, phthalide, probenazole, propiconazole,
pyroquilon, tebuconazole, thifluzamide, tricyclazole,
trifloxystrobin, validamycin, and a compound of formula (II)
##STR00004##
[0004] A second embodiment, including the composition according to
the first embodiment, wherein (a) is a C.sub.1-4 alkyl or benzyl
ester of compound (I).
[0005] A third embodiment, including the composition according to
the first embodiment, wherein (a) is a C.sub.1-4 alkyl ester of
compound (I).
[0006] A fourth embodiment including the composition according to
the second embodiment, wherein (a) is a benzyl ester of compound
(I).
[0007] A fifth embodiment including the composition according to
the first embodiment, wherein (a) is the compound of formula (I),
which is the carboxylic acid.
[0008] A sixth embodiment including the compositions according to
the first through the fifth embodiments, further comprising at
least one compound selected from the group consisting of: a
herbicide safener, carrier and adjuvent.
[0009] A seventh embodiment including at least one composition
according the first through the sixth embodiments the wherein the
ratios of the compound of formula (I) or agriculturally acceptable
salt or ester thereof to azoxystrobin in units of g to g, gae/ha to
gae/ha, or gae/ha gai/ha is from about 1:500 to about 12:1.
[0010] An eighth embodiment including at least one composition
according the first through the sixth embodiments the wherein the
ratios of the compound of formula (I) or agriculturally acceptable
salt or ester thereof to carbendazim in units of g to g, gae/ha to
gae/ha, or gae/ha gai/ha is from about 1:375 to about 12:1.
[0011] A ninth embodiment including at least one composition
according the first through the sixth embodiments the wherein the
ratios of the compound of formula (I) or agriculturally acceptable
salt or ester thereof to difenoconazole in units of g to g, gae/ha
to gae/ha, or gae/ha gai/ha is from about 1:250 to about 12:1.
[0012] A tenth embodiment including at least one composition
according the first through the sixth embodiments the wherein the
ratios of the compound of formula (I) or agriculturally acceptable
salt or ester thereof to flutolanil in units of g to g, gae/ha to
gae/ha, or gae/ha gai/ha is from about 1:500 to about 12:1.
[0013] An eleventh embodiment including at least one composition
according the first through the sixth embodiments the wherein the
ratios of the compound of formula (I) or agriculturally acceptable
salt or ester thereof to hexaconazole in units of g to g, gae/ha to
gae/ha, or gae/ha gai/ha is from about 1:250 to about 60:1.
[0014] A twelfth embodiment including at least one composition
according the first through the sixth embodiments the wherein the
ratios of the compound of formula (I) or agriculturally acceptable
salt or ester thereof to iprobenfos in units of g to g, gae/ha to
gae/ha, or gae/ha gai/ha is from about 1:1,000 to about 3:1.
[0015] A thirteenth embodiment including at least one composition
according the first through the sixth embodiments the wherein the
ratios of the compound of formula (I) or agriculturally acceptable
salt or ester thereof to isoprothiolane in units of g to g, gae/ha
to gae/ha, or gae/ha gai/ha is from about 3:11:500 to about
6:1.
[0016] A fourteenth embodiment including at least one composition
according the first through the sixth embodiments the wherein the
ratios of the compound of formula (I) or agriculturally acceptable
salt or ester thereof to isotianil in units of g to g, gae/ha to
gae/ha, or gae/ha gai/ha is from about 1:500 to about 30:1.
[0017] A fifteenth embodiment including at least one composition
according the first through the sixth embodiments the wherein the
ratios of the compound of formula (I) or agriculturally acceptable
salt or ester thereof to kasugamycin in units of g to g, gae/ha to
gae/ha, or gae/ha gai/ha is from about 1:250 to about 150:1.
[0018] A sixteenth embodiment including at least one composition
according the first through the sixth embodiments the wherein the
ratios of the compound of formula (I) or agriculturally acceptable
salt or ester thereof to mancozeb in units of g to g, gae/ha to
gae/ha, or gae/ha gai/ha is from about 1:2500 to about 12:1.
[0019] A seventeenth embodiment including at least one composition
according the first through the sixth embodiments the wherein the
ratios of the compound of formula (I) or agriculturally acceptable
salt or ester thereof to myclobutanil in units of g to g, gae/ha to
gae/ha, or gae/ha gai/ha is from about 1:250 to about 12:1.
[0020] An eighteenth embodiment including at least one composition
according the first through the sixth embodiments the wherein the
ratios of the compound of formula (I) or agriculturally acceptable
salt or ester thereof to phthalide in units of g to g, gae/ha to
gae/ha, or gae/ha gai/ha is from about 1:500 to about 15:1.
[0021] A nineteenth embodiment including at least one composition
according the first through the sixth embodiments the wherein the
ratios of the compound of formula (I) or agriculturally acceptable
salt or ester thereof to probenazole in units of g to g, gae/ha to
gae/ha, or gae/ha gai/ha is from about 1:2500 to about 6:1.
[0022] A twentieth embodiment including at least one composition
according the first through the sixth embodiments the wherein the
ratios of the compound of formula (I) or agriculturally acceptable
salt or ester thereof to propiconazole in units of g to g, gae/ha
to gae/ha, or gae/ha gai/ha is from about 1:250 to about 30:1.
[0023] A twenty-first embodiment including at least one composition
according the first through the sixth embodiments the wherein the
ratios of the compound of formula (I) or agriculturally acceptable
salt or ester thereof to pyroquilon in units of g to g, gae/ha to
gae/ha, or gae/ha gai/ha is from about 1:1,500 to about 3:1.
[0024] A twenty-second embodiment including at least one
composition according the first through the sixth embodiments the
wherein the ratios of the compound of formula (I) or agriculturally
acceptable salt or ester thereof to tebuconazole in units of g to
g, gae/ha to gae/ha, or gae/ha gai/ha is from about 1:250 to about
12:1.
[0025] A twenty-third embodiment including at least one composition
according the first through the sixth embodiments the wherein the
ratios of the compound of formula (I) or agriculturally acceptable
salt or ester thereof to thifluzamide in units of g to g, gae/ha to
gae/ha, or gae/ha gai/ha is from about 1:375 to about 30:1.
[0026] A twenty-fourth embodiment including at least one
composition according the first through the sixth embodiments the
wherein the ratios of the compound of formula (I) or agriculturally
acceptable salt or ester thereof to tricyclazole in units of g to
g, gae/ha to gae/ha, or gae/ha gai/ha is from about 1:375 to about
15:1.
[0027] A twenty-fifth embodiment including at least one composition
according the first through the sixth embodiments the wherein the
ratios of the compound of formula (I) or agriculturally acceptable
salt or ester thereof to trifloxystrobin in units of g to g, gae/ha
to gae/ha, or gae/ha gai/ha is from about 1:250 to about 30:1.
[0028] A twenty-sixth embodiment including at least one composition
according the first through the sixth embodiments the wherein the
ratios of the compound of formula (I) or agriculturally acceptable
salt or ester thereof to validamycin in units of g to g, gae/ha to
gae/ha, or gae/ha gai/ha is from about 1:25 to about 3,000:1.
[0029] A twenty-seventh embodiment including at least one
composition according the first through the sixth embodiments the
wherein the ratios of the compound of formula (I) or agriculturally
acceptable salt or ester thereof to a compound of formula (II) in
units of g to g, gae/ha to gae/ha, or gae/ha gai/ha is from about
1:375 to about 150:1.
[0030] A twenty-eighth embodiment includes methods for controlling
undesirable vegetation which comprises contacting the vegetation or
the area adjacent to the vegetation with or applying to the soil or
water to prevent the emergence or growth of vegetation the
composition of any of the composition according to the first
through the twenty-seventh embodiments.
[0031] A twenty-ninth embodiment includes methods of controlling
undesirable vegetation which comprises contacting the vegetation or
the area adjacent to the vegetation with or applying to the soil or
water to prevent the emergence or growth of vegetation a
herbicidally effective amount of (a) a compound of the formula
(I)
##STR00005##
or an agriculturally acceptable salt or ester thereof and (b)
azoxystrobin, carbendazim, difenoconazole, flutolanil,
hexaconazole, iprobenfos, isoprothiolane, isotianil, kasugamycin,
mancozeb, myclobutanil, phthalide, probenazole, propiconazole,
pyroquilon, tebuconazole, thifluzamide, tricyclazole,
trifloxystrobin, validamycin, and a compound of formula (II)
##STR00006##
[0032] A thirtieth embodiment includes methods according to the
twenty-eighth and twenty-ninth embodiments for controlling
undesired vegetation, wherein the undesirable vegetation is
controlled in direct-seeded, water-seeded and transplanted rice,
cereals, wheat, barley, oats, rye, sorghum, corn/maize, sugarcane,
sunflower, oilseed rape, canola, sugar beet, soybean, cotton,
pineapple, pastures, grasslands, rangelands, fallowland, turf, tree
and vine orchards, plantation crops, vegetables, industrial
vegetation management (IVM) and rights of way (ROW).
[0033] A thirty-first embodiment includes methods according to the
twenty-eighth and twenty-ninth embodiments, wherein the undesirable
vegetation is immature.
[0034] A thirty-second embodiment includes methods according to the
twenty-eighth and twenty-ninth embodiments, wherein the compounds
(a) and (b) are applied to water.
[0035] The thirty-third embodiment includes methods according to
the thirty-second embodiment wherein the water is part of a flooded
rice paddy.
[0036] A thirty-fourth embodiment includes methods according to the
twenty-eighth and twenty-ninth embodiments wherein the compound (a)
and (b) are applied pre-emergently and/or post emergently to the
weed or the crop.
[0037] A thirty-fifth embodiment includes methods according to the
twenty-eighth and twenty-ninth embodiments, wherein the undesirable
vegetation is controlled in glyphosate-,
5-enolpyruvylshikimate-3-phosphate (EPSP) synthase inhibitor-,
glufosinate-, glutamine synthetase inhibitor-, dicamba-, phenoxy
auxin-, pyridyloxy auxin-, synthetic auxin-, auxin transport
inhibitor-, aryloxyphenoxypropionate-, cyclohexanedione-,
phenylpyrazoline-, acetyl CoA carboxylase (ACCase) inhibitor-,
imidazolinone-, sulfonylurea-, pyrimidinylthiobenzoate-,
triazolopyrimidine-, sulfonylaminocarbonyltriazolinone-,
acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS)
inhibitor-, 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitor-,
phytoene desaturase inhibitor-, carotenoid biosynthesis inhibitor-,
protoporphyrinogen oxidase (PPO) inhibitor-, cellulose biosynthesis
inhibitor-, mitosis inhibitor-, microtubule inhibitor-, very long
chain fatty acid inhibitor-, fatty acid and lipid biosynthesis
inhibitor-, photosystem I inhibitor-, photosystem II inhibitor-,
triazine-, or bromoxynil-tolerant crops.
[0038] A thirty-sixth embodiment includes methods according to the
thirty-fifth embodiment, wherein the tolerant crop possesses
multiple or stacked traits conferring tolerance to multiple
herbicides or multiple modes of action.
[0039] A thirty-seventh embodiment includes methods according to
the twenty-eighth and twenty-ninth embodiments, wherein the
undesirable vegetation comprises a herbicide resistant or tolerant
weed.
[0040] A thirty-eighth embodiment includes methods according to the
thirty-seventh embodiment, wherein the resistant or tolerant weed
is a biotype with resistance or tolerance to multiple herbicides,
multiple chemical classes, multiple herbicide modes-of-action, or
via multiple resistance mechanisms.
[0041] The thirty-ninth embodiment includes methods according to
the twenty-eighth and twenty-ninth embodiments, wherein the
resistant or tolerant weed is a biotype resistant or tolerant to
acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS)
inhibitors, photosystem II inhibitors, acetyl CoA carboxylase
(ACCase) inhibitors, synthetic auxins, auxin transport inhibitors,
photosystem I inhibitors, 5-enolpyruvylshikimate-3-phosphate (EPSP)
synthase inhibitors, microtubule assembly inhibitors, fatty acid
and lipid synthesis inhibitors, protoporphyrinogen oxidase (PPO)
inhibitors, carotenoid biosynthesis inhibitors, very long chain
fatty acid (VLCFA) inhibitors, phytoene desaturase (PDS)
inhibitors, glutamine synthetase inhibitors,
4-hydroxyphenyl-pyruvate-dioxygenase (HPPD) inhibitors, mitosis
inhibitors, cellulose biosynthesis inhibitors, herbicides with
multiple modes-of-action, quinclorac, arylaminopropionic acids,
difenzoquat, endothall, or organoarsenicals.
[0042] 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)
fungicides. The compositions may also contain an agriculturally
acceptable adjuvant or carrier. Provided herein are also methods of
controlling undesirable vegetation comprising applying (a) a
compound of formula (I) or an agriculturally acceptable ester or
salt thereof and (b) fungicides.
DETAILED DESCRIPTION
Definitions
[0043] As used herein, the compound of formula (I) has the
following structure:
##STR00008##
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.
[0044] Fungicides are a class of pesticides used to control plant
pathogens in crop and non-crop settings. Without being limited to
any theory, these pesticides kill diseases/plant pathogens via
multiple, different modes of action. Exemplary uses of fungicides
include their use to control plant diseases and plant pathogens in
cereal, legume, vegetable, fruit, row and perennial crops.
[0045] Exemplary fungicides include, but are not limited to,
azoxystrobin, carbendazim, difenoconazole, flutolanil,
hexaconazole, iprobenfos, isoprothiolane, isotianil, kasugamycin,
mancozeb, myclobutanil, phthalide, probenazole, propiconazole,
pyroquilon, tebuconazole, thifluzamide, tricyclazole,
trifloxystrobin, validamycin, and a compound of formula (II):
##STR00009##
[0046] As used herein, azoxystrobin is methyl
(E)-{2-[6(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl}3-methoxyacrylate
and possesses the following structure:
##STR00010##
[0047] Its fungicidal activity is exemplified in Tomlin, C., ed. A
World Compendium The Pesticide Manual. 15.sup.th ed. Alton: BCPC
Publications, 2009. Exemplary uses of azoxystrobin include its use
as a protectant, curative and eradicant fungicide for the control
of many plant pathogens in crops, including Pyricularia and
Rhizoctonia in rice. Azoxystrobin can be applied, e.g., as a
post-emergence treatment to control undesirable plant
pathogens.
[0048] As used herein, carbendazim is methyl
benzimidazol-2-ylcarbamate and possesses the following
structure:
##STR00011##
[0049] Its fungicidal activity is exemplified in Tomlin, C., ed. A
World Compendium The Pesticide Manual. 15.sup.th ed. Alton: BCPC
Publications, 2009. Exemplary uses of carbendazim include its use
as a systemic fungicide with protective and curative action for the
control of Septoria, Fusarium, Erysiphe and other diseases in
cereals crops. Carbendazim can be applied, e.g., post-emergence to
control undesirable plant pathogens.
[0050] As used herein difenoconazole is cis,
trans-3-chloro-4-[4-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3,dioxolan-2-
-yl]pheyl chlorophenyl ether and possesses the following
structure:
##STR00012##
[0051] Its fungicidal activity is exemplified in Tomlin, C., ed. A
World Compendium The Pesticide Manual. 15.sup.th ed. Alton: BCPC
Publications, 2009. Exemplary uses of difenoconazole include its
use as a systemic fungicide with preventative and curative activity
for the control of plant diseases in many crops, including
Rhizoctonia, Cercospora, Septoria and many other diseases in rice,
cereals, oilseed rape, etc. Difenoconazole can be applied, e.g., as
a post-emergence treatment to control undesirable plant
pathogens.
[0052] As used herein, flutolanil is
.alpha.,.alpha.,.alpha.-trifluoro-3'-isopropoxy-o-toluanilide and
possesses the following structure:
##STR00013##
[0053] Its fungicidal activity is exemplified in Tomlin, C., ed. A
World Compendium The Pesticide Manual. 15.sup.th ed. Alton: BCPC
Publications, 2009. Exemplary uses of flutolanil include its use as
a systemic fungicide for the control of Rhizoctonia in many crops,
including rice, cereals, turf, etc. Flutolanil can be applied,
e.g., as a post-emergence treatment to control undesirable plant
pathogens.
[0054] As used herein, hexaconazole is
(RS)-2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)hexan-2-ol)
and possesses the following structure:
##STR00014##
[0055] Its fungicidal activity is exemplified in Tomlin, C., ed. A
World Compendium The Pesticide Manual. 15.sup.th ed. Alton: BCPC
Publications, 2009. Exemplary uses of hexaconazole include its use
for the control of Ascomycetes and Basidiomycetes in vine, coffee,
and other crops. Hexaconazole can be applied, e.g., as a
post-emergence treatment to control undesirable plant
pathogens.
[0056] As used herein, iprobenfos is S-benzyl O,O-diisopropyl
phosphorothioate and possesses the following structure:
##STR00015##
[0057] Its fungicidal activity is exemplified in Tomlin, C., ed. A
World Compendium The Pesticide Manual. 15.sup.th ed. Alton: BCPC
Publications, 2009. Exemplary uses of Iprobenfos include its use as
a systemic fungicide for the control of rice blast (Pyricularia),
stem rot and sheath blight (Rhizoctonia) in rice. Iiprobenfos can
be applied, e.g., as a post-emergence treatment to control
undesirable plant pathogens.
[0058] As used herein, isoprothiolane is diisopropyl
1,3-dithiolan-2-ylidenemalonate and possesses the following
structure:
##STR00016##
[0059] Its fungicidal activity is exemplified in Tomlin, C., ed. A
World Compendium The Pesticide Manual. 15.sup.th ed. Alton: BCPC
Publications, 2009. Exemplary uses of isoprothiolane include its
use as a systemic fungicide that inhibits penetration and
elongation of infection hyphae for the control of Pyricularia and
other diseases in rice and other crops. isoprothiolane can be
applied, e.g., post-emergence treatment to control undesirable
plant pathogens.
[0060] As used herein isotianil
is3,4-dichloro-2'cyano-1,2-thiazole-5-carboxanilide and possesses
the following structure:
##STR00017##
[0061] Its fungicidal activity is exemplified in Tomlin, C., ed. A
World Compendium The Pesticide Manual. 15.sup.th ed. Alton: BCPC
Publications, 2009. Exemplary uses of isotianil include its use for
the control of rice blast (Pyricularia) in rice. isotianil can be
applied, e.g., post-emergence or rice nursery box drench treatment
to control undesirable plant pathogens.
[0062] As used herein, kasugamycin is
11-1,3,4/2,5,6-1-deoxy-2,3,4,5,6,-pentahydroxycyclohexyl
2-amino-2,3,4,6-tetradeoxy-4-(.alpha.-iminoglycino)-.alpha.-D-arabino-hex-
opyranoside hydrochloride hydrate and possesses the following
structure:
##STR00018##
[0063] Its fungicidal activity is exemplified in Tomlin, C., ed. A
World Compendium The Pesticide Manual. 15.sup.th ed. Alton: BCPC
Publications, 2009. Exemplary uses of kasugamycin include its use
as a systemic fungicide and bactericide that inhibits hyphal growth
of rice blast (Pyricularia) in rice. Kasugamycin can be applied,
e.g., rice nursery drench and post-emergence treatments to control
undesirable plant pathogens.
[0064] As used herein, mancozeb is manganexe
ethylenebis(dithiocarbamate) (polymeric) complex with zinc salt and
possesses the following structure:
##STR00019##
x:y=1:0.091
[0065] Its fungicidal activity is exemplified in Tomlin, C., ed. A
World Compendium The Pesticide Manual. 15.sup.th ed. Alton: BCPC
Publications, 2009. Exemplary uses of mancozeb include its use as a
protectant fungicide for the control of many fungal diseases in
many crops. Mancozeb in a fungal respiration inhibitor, and can be
applied, e.g., as a post-emergence and seed treatment to control
many undesirable plant pathogens.
[0066] As used herein, myclobutanil
is2-p-chlorophenyl-2-(1H-1,2,4-triazol-1-ylmethyl)hexanenitrile and
possesses the following structure:
##STR00020##
[0067] Its fungicidal activity is exemplified in Tomlin, C., ed. A
World Compendium The Pesticide Manual. 15.sup.th ed. Alton: BCPC
Publications, 2009. Exemplary uses of myclobutanil, a known
ergosterol biosynthesis inhibitor with protective and curative
properties, include its use for the control of Ascomycetes, Fungi
Imperfecti and Basidomycetes in many crops. Myclobutanil can be
applied, e.g., post-emergence and seed treatment to control
undesirable plant pathogens.
[0068] As used herein, phthalide is 4,5,6,7-tetrachlorophthalide
and possesses the following structure:
##STR00021##
[0069] Its fungicidal activity is exemplified in Tomlin, C., ed. A
World Compendium The Pesticide Manual. 15.sup.th ed. Alton: BCPC
Publications, 2009. Exemplary uses of phthalide include its use for
the control of rice blast (Pyricularia oryzae) in rice. Phthalide
can be applied, e.g., drench and post-emergence to control rice
blast in rice.
[0070] As used herein, probenazole, is
3-allyloxy-1,2-benz[d]isothiazole 1,1-dioxide and possesses the
following structure:
##STR00022##
[0071] Its fungicidal activity is exemplified in Tomlin, C., ed. A
World Compendium The Pesticide Manual. 15.sup.th ed. Alton: BCPC
Publications, 2009. Exemplary uses of probenazole include its use
for the control of rice blast and leaf blight in transplanted rice.
Probenazole can be applied, e.g., post-emergence treatment to
control undesirable plant pathogens in rice.
[0072] As used herein, propiconazole is
1-[2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolan-2
ylmethyl]1H-1,2,4-triazole and possesses the following
structure:
##STR00023##
[0073] Its fungicidal activity is exemplified in Tomlin, C., ed. A
World Compendium The Pesticide Manual. 15.sup.th ed. Alton: BCPC
Publications, 2009. Exemplary uses of propiconazole include its use
for the control of Rhizoctonia and dirty panicle complex in rice,
as well as many diseases in cereal, turf and corn crops.
Propiconazole can be applied, e.g., post-emergence treatment to
control undesirable plant pathogens in many crops.
[0074] As used herein, pyroquilon is
1,2,5,6-tetrahydropyrrolo[3,2,1-ij]quinolin-4-one and possesses the
following structure:
##STR00024##
[0075] Its fungicidal activity is exemplified in Tomlin, C., ed. A
World Compendium The Pesticide Manual. 15.sup.th ed. Alton: BCPC
Publications, 2009. Exemplary uses of pyroquilon, a known melanin
biosynthesis inhibitor, include its use for the control of
Pyricularia in rice. Pyroquilon can be applied, e.g., as a
post-emergence and seed drench treatment to control undesirable
plant pathogens in rice.
[0076] As used herein, tebuconazole is
(RS)-1-p-chlorophenyl-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan--
3-ol and possesses the following structure:
##STR00025##
[0077] Its fungicidal activity is exemplified in Tomlin, C., ed. A
World Compendium The Pesticide Manual. 15.sup.th ed. Alton: BCPC
Publications, 2009. Tebuconazole acts by inhibition of ergosterol
biosynthesis, providing protective, curative and eradicant
activity. Exemplary uses of tebuconazole include its use for the
control of many diseases across many crops, including Puccinia,
Fusarium, Erysiphe and other diseases. Tebuconazole can be applied,
e.g., as a post-emergence treatment to control undesirable plant
pathogens.
[0078] As used herein, thifluzamide is
2',6'-dibromo-2-methyl-4'-trifluoromethoxy-4-trifluoromethyl-1,3-thiazole-
-5-carboxanilide and possesses the following structure:
##STR00026##
[0079] Its fungicidal activity is exemplified in Tomlin, C., ed. A
World Compendium The Pesticide Manual. 15.sup.th ed. Alton: BCPC
Publications, 2009. Exemplary uses of thifluzamide include its use
for the control of Basidiomycetes diseases including Rhizoctonia in
rice and cereal crops. Thifluzamide can be applied, e.g.,
post-emergence and seed treatment to control undesirable plant
pathogens.
[0080] As used herein, tricyclazole is
5-methyl-1,2,4-triazolo[3,4-b][1,3]benzothiazole and possesses the
following structure:
##STR00027##
[0081] Its fungicidal activity is exemplified in Tomlin, C., ed. A
World Compendium The Pesticide Manual. 15.sup.th ed. Alton: BCPC
Publications, 2009. Exemplary uses of tricyclazole, a known melanin
biosynthesis inhibitor, include its use for the control of rice
blast (Pyricularia oryzae) in seeded and transplanted rice.
Tricyclazole can be applied, e.g., as a post-emergence, seed or
soak treatment to control undesirable plant pathogens in rice.
[0082] As used herein, trifloxystrobin is methyl
(E)-methoxyimino-{(E)-.alpha.-[1-(.alpha.,.alpha.,.alpha.-trifluoro-m-tol-
yl)ethylideneaminooxy]-o-tolyl}acetate and possesses the following
structure:
##STR00028##
[0083] Its fungicidal activity is exemplified in Tomlin, C., ed. A
World Compendium The Pesticide Manual. 15.sup.th ed. Alton: BCPC
Publications, 2009. Exemplary uses of trifloxystrobin include its
use for the control of rusts and powdery mildew in cereal, fruit
and vegetable crops. Trifloxystrobin can be applied, e.g., as a
post-emergence treatment to control undesirable plant
pathogens.
[0084] As used herein, validamycin is
1L-(1R,2R,3S,4S,6R)-2,3-dihydroxy-6-(hydroxymethyl)-4-{[(1S,4S,5S,6S)-4,5-
,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl]amino}cyclohexyl
.beta.-D-glucopyranoside and possesses the following structure:
##STR00029##
[0085] Its fungicidal activity is exemplified in Tomlin, C., ed. A
World Compendium The Pesticide Manual. 15.sup.th ed. Alton: BCPC
Publications, 2009. Exemplary uses of validamycin include its use
for the control of Rhizoctonia solani in rice and many other crops.
Validamycin can be applied, e.g., post-mergence, soil drench or
seed treatment to control undesirable plant pathogens.
[0086] As used herein, a compound of formula (II) possesses the
following structure:
##STR00030##
[0087] Its fungicidal activity is exemplified in: International
Patent Publication No. WO 03/035617, published May 1, 2003.
Exemplary uses of a compound of formula (II) include its use for
the control of rust and other diseases in cereal crops. A compound
of formula (II) can be applied, e.g., post-emergence treatment to
control undesirable plant pathogens.
[0088] As used herein, fungicide means a compound, e.g., active
ingredient that kills, controls or otherwise adversely modifies the
growth of plant diseases/pathogens. As used herein, fungicide means
a compound, e.g., active ingredient that kills, controls or
otherwise adversely modifies the growth of fungi.
[0089] As used herein, a fungicidal effective or controlling amount
is an amount of active ingredient which causes an adversely
modifying effect to the fungi to be controlled, e.g., causing
deviations from natural development, killing, effecting regulation,
causing desiccation, causing retardation, and the like.
[0090] 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 and fungicide combinations or compositions
Methods of application include, but are not limited to applications
to the vegetation or locus thereof, e.g., application to the area
adjacent to the vegetation, as well as pre-emergence,
post-emergence, foliar (broadcast, directed, banded, spot,
mechanical, over-the-top, or rescue), and in-water applications
(emerged and submerged vegetation, broadcast, spot, mechanical,
water-injected, granular broadcast, granular spot, shaker bottle,
or stream spray) via hand, backpack, machine, tractor, or aerial
(airplane and helicopter) application methods.
[0091] As used herein, plants and vegetation include, but are not
limited to, germinant seeds, emerging seedlings, plants emerging
from vegetative propagules, immature vegetation, and established
vegetation.
[0092] 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.
[0093] 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
ammonium 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.
[0094] 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
[0095] Provided herein are herbicidal compositions comprising a
herbicidally effective amount of (a) a compound of the formula
(I)
##STR00031##
or an agriculturally acceptable salt or ester of thereof, and (b)
fungicides, including but not limited to, azoxystrobin,
carbendazim, difenoconazole, flutolanil, hexaconazole, iprobenfos,
isoprothiolane, isotianil, kasugamycin, mancozeb, myclobutanil,
phthalide, probenazole, propiconazole, pyroquilon, tebuconazole,
thifluzamide, tricyclazole, trifloxystrobin, validamycin, and a
compound of formula (II).
[0096] Provided herein are also methods of controlling undesirable
vegetation comprising contacting the vegetation or locus thereof,
i.e., the area adjacent to the vegetation with or applying to the
soil or water to prevent the emergence or growth of vegetation a
herbicidally effective amount of the compound of formula (I) or
agriculturally acceptable salt or ester thereof and (b) fungicides,
including but not limited to, azoxystrobin, carbendazim,
difenoconazole, flutolanil, hexaconazole, iprobenfos,
isoprothiolane, isotianil, kasugamycin, mancozeb, myclobutanil,
phthalide, probenazole, propiconazole, pyroquilon, tebuconazole,
thifluzamide, tricyclazole, trifloxystrobin, validamycin, and a
compound of formula (II). In certain embodiments, the methods
employ the compositions described herein.
[0097] Furthermore, in some embodiments, the combination of
compound (I) or agriculturally acceptable salt or ester thereof and
azoxystrobin, carbendazim, difenoconazole, flutolanil,
hexaconazole, iprobenfos, isoprothiolane, isotianil, kasugamycin,
mancozeb, myclobutanil, phthalide, probenazole, propiconazole,
pyroquilon, tebuconazole, thifluzamide, tricyclazole,
trifloxystrobin, validamycin, and a compound of formula (II)
exhibits synergism, e.g., the herbicidal activity is more effective
in combination than when compound of formula (1) is applied
individually. Synergism has been defined as "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." Senseman, S., ed. Herbicide Handbook. 9.sup.th ed.
Lawrence: Weed Science Society of America, 2007. In certain
embodiments, the compositions exhibit synergy as determined by the
Colby's equation. Colby, S. R. 1967. Calculation of the synergistic
and antagonistic response of herbicide combinations. Weeds
15:20-22.
[0098] In certain embodiments of the compositions and methods
described herein, the compound of formula (I), i.e., the carboxylic
acid, is employed. In certain embodiments, a carboxylate salt of
the compound of formula (I) is employed. In certain embodiments, an
aralkyl or alkyl ester is employed. In certain embodiments, a
benzyl, substituted benzyl, or C.sub.1-4 alkyl, e.g., n-butyl ester
is employed. In certain embodiments, the benzyl ester is
employed.
[0099] In some embodiments, the compound of formula (I) or salt or
ester thereof and azoxystrobin, carbendazim, difenoconazole,
flutolanil, hexaconazole, iprobenfos, isoprothiolane, isotianil,
kasugamycin, mancozeb, myclobutanil, phthalide, probenazole,
propiconazole, pyroquilon, tebuconazole, thifluzamide,
tricyclazole, trifloxystrobin, validamycin, and a compound of
formula (II) are formulated in one composition, tank mixed, applied
simultaneously, or applied sequentially.
[0100] Herbicidal activity is exhibited by the compounds when they
are applied directly to the plant or to the area adjacent to 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. In some embodiments, the compositions described herein are
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), to relatively immature
undesirable vegetation to achieve the maximum control of weeds.
[0101] In some embodiments, the compositions and methods provided
herein are utilized to control weeds in crops, including but not
limited to direct-seeded, water-seeded and transplanted rice,
cereals, wheat, barley, oats, rye, sorghum, corn/maize, sugarcane,
sunflower, oilseed rape, canola, sugar beet, soybean, cotton,
pineapple, pastures, grasslands, rangelands, fallowland, turf, tree
and vine orchards, plantation crops, vegetables, industrial
vegetation management (IVM) and rights of way (ROW).
[0102] In certain embodiments, the compositions and methods
provided herein are utilized to control weeds in rice. In certain
embodiments, the rice is direct-seeded, water-seeded, or
transplanted rice.
[0103] The compositions and methods described herein may be used to
control undesirable vegetation in glyphosate-tolerant-,
5-enolpyruvylshikimate-3-phosphate (EPSP) synthase
inhibitor-tolerant-, glufosinate-tolerant-, glutamine synthetase
inhibitor-tolerant-, dicamba-tolerant-, phenoxy auxin-tolerant-,
pyridyloxy auxin-tolerant-, auxin-tolerant-, auxin transport
inhibitor-tolerant-, aryloxyphenoxypropionate-tolerant-,
cyclohexanedione-tolerant-, phenylpyrazoline-tolerant-, acetyl CoA
carboxylase (ACCase) inhibitor-tolerant-, imidazolinone-tolerant-,
sulfonylurea-tolerant-, pyrimidinylthiobenzoate-tolerant-,
triazolopyrimidine-tolerant-,
sulfonylaminocarbonyltriazolinone-tolerant-, acetolactate synthase
(ALS) or acetohydroxy acid synthase (AHAS) inhibitor-tolerant-,
4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitor-tolerant-,
phytoene desaturase inhibitor-tolerant-, carotenoid biosynthesis
inhibitor-tolerant-, protoporphyrinogen oxidase (PPO)
inhibitor-tolerant-, cellulose biosynthesis inhibitor-tolerant-,
mitosis inhibitor-tolerant-, microtubule inhibitor-tolerant-, very
long chain fatty acid inhibitor-tolerant-, fatty acid and lipid
biosynthesis inhibitor-tolerant-, photosystem I
inhibitor-tolerant-, photosystem II inhibitor-tolerant-,
triazine-tolerant- and bromoxynil-tolerant-crops (such as, but not
limited to, soybean, cotton, canola/oilseed rape, rice, cereals,
corn, sorghum, sunflower, sugar beet, sugarcane, turf, etc), for
example, in conjunction with glyphosate, EPSP synthase inhibitors,
glufosinate, glutamine synthase inhibitors, dicamba, phenoxy
auxins, pyridyloxy auxins, synthetic auxins, auxin transport
inhibitors, aryloxyphenoxypropionates, cyclohexanediones,
phenylpyrazolines, ACCase inhibitors, imidazolinones,
sulfonylureas, pyrimidinylthiobenzoates, triazolopyrimidines,
sulfonylaminocarbonyltriazolinones, ALS or AHAS inhibitors, HPPD
inhibitors, phytoene desaturase inhibitors, carotenoid biosynthesis
inhibitors, PPO inhibitors, cellulose biosynthesis inhibitors,
mitosis inhibitors, microtubule inhibitors, very long chain fatty
acid inhibitors, fatty acid and lipid biosynthesis inhibitors,
photosystem I inhibitors, photosystem II inhibitors, triazines, and
bromoxynil. The compositions and methods may be used in controlling
undesirable vegetation in crops possessing multiple or stacked
traits conferring tolerance to multiple chemistries and/or
inhibitors of multiple modes of action. In some embodiments, the
compound of formula (I) or salt or ester thereof and complementary
herbicide or salt or ester thereof are 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. In some embodiments, the
compositions described herein and other complementary herbicides
are applied at the same time, either as a combination formulation
or as a tank mix, or sequentially.
[0104] The compositions and methods may be used in controlling
undesirable vegetation in crops possessing agronomic stress
tolerance (including but not limited to drought, cold, heat, salt,
water, nutrient, fertility, pH), pest tolerance (including but not
limited to insects, fungi and pathogens) and crop improvement
traits (including but not limited to yield; protein, carbohydrate,
or oil content; protein, carbohydrate, or oil composition; plant
stature and plant architecture).
[0105] The compositions and methods provided herein are utilized to
control undesirable vegetation. Undesirable vegetation includes,
but is not limited to, undesirable vegetation that occurs in rice,
cereals, wheat, barley, oats, rye, sorghum, corn/maize, sugarcane,
sunflower, oilseed rape, canola, sugar beet, soybean, cotton,
pineapple, pastures, grasslands, rangelands, fallowland, turf, tree
and vine orchards, aquatics, plantation crops, vegetables,
industrial vegetation management (IVM) and rights of way (ROW).
[0106] In some embodiments, the methods provided herein are
utilized to control undesirable vegetation in rice. In certain
embodiments, the undesirable vegetation is Brachiaria platyphylla
(Groseb.) Nash or Urochloa platyphylla (Nash) R. D. Webster
(broadleaf signalgrass, BRAPP), Digitaria sanguinalis (L.) Scop.
(large crabgrass, DIGSA), Echinochloa species (ECHSS), Echinochloa
crus-galli (L.) P. Beauv. (barnyardgrass, ECHCG), Echinochloa
crus-pavonis (Kunth) Schult. (gulf cockspur, ECHCV), Echinochloa
colonum (L.) LINK (junglerice, ECHCO), Echinochloa oryzoides (Ard.)
Fritsch (early watergrass, ECHOR), Echinochloa oryzicola (Vasinger)
Vasinger (late watergrass, ECHPH), Echinochloa phyllopogon (Stapf)
Koso-Pol. (rice barnyardgrass, ECHPH), Echinochloa polystachya
(Kunth) Hitchc. (creeping river grass, ECHPO), Ischaemum rugosum
Salisb. (saramollagrass, ISCRU), Leptochloa chinensis (L.) Nees
(Chinese sprangletop, LEFCH), Leptochloa fascicularis (Lam.) Gray
(bearded sprangletop, LEFFA), Leptochloa panicoides (Presl.)
Hitchc. (Amazon sprangletop, LEFPA), Oryza species (red and weedy
rice, ORYSS), Panicum dichotomiflorum (L.) Michx. (fall panicum,
PANDI), Paspalum dilatatum Poir. (dallisgrass, PASDI), Rottboellia
cochinchinensis (Lour.) W. D. Clayton (itchgrass, ROOEX), Cyperus
species (CYPSS), Cyperus difformis L. (smallflower flatsedge,
CYPDI), Cyperus dubius Rottb. (MAPDU), Cyperus esculentus L.
(yellow nutsedge, CYPES), Cyperus iria L. (rice flatsedge, CYPIR),
Cyperus rotundus L. (purple nutsedge, CYPRO), Eleocharis species
(ELOSS), Fimbristylis miliacea (L.) Vahl (globe fringerush, FIMMI),
Schoenoplectus species (SCPSS), Schoenoplectus juncoides Roxb.
(Japanese bulrush, SCPJU), Bolboschoenus maritimus (L.) Palla or
Schoenoplectus maritimus L. Lye (sea clubrush, SCPMA),
Schoenoplectus mucronatus L. (ricefield bulrush, SCPMU),
Aeschynomene species, (jointvetch, AESSS), Alternanthera
phdoxeroides (Mart.) Griseb. (alligatorweed, ALRPH), Alisma
plantago-aquatica L. (common waterplantain, ALSPA), Amaranthus
species, (pigweeds and amaranths, AMASS), Ammannia coccinea Rottb.
(redstem, AMMCO), Commelina benghalensis L. (Benghal dayflower,
COMBE), Eclipta alba (L.) Hassk. (American false daisy, ECLAL),
Heteranthera limosa (SW.) Willd./Vahl (ducksalad, HETLI),
Heteranthera reniformis R. & P. (roundleaf mudplantain, HETRE),
Ipomoea species (morningglories, IPOSS), Ipomoea hederacea (L.)
Jacq. (ivyleaf morningglory, IPOHE), Lindernia dubia (L.) Pennell
(low false pimpernel, LIDDU), Ludwigia species (LUDSS), Ludwigia
linifolia Poir. (southeastern primrose-willow, LUDLI), Ludwigia
octovalvis (Jacq.) Raven (longfruited primrose-willow, LUDOC),
Monochoria korsakowii Regel & Maack (monochoria, MOOKA),
Monochoria vaginalis (Berm. F.) C. Presl ex Kuhth, (monochoria,
MOOVA), Murdannia nudiflora (L.) Brenan (doveweed, MUDNU),
Polygonum pensylvanicum L., (Pennsylvania smartweed, POLPY),
Polygonum persicaria L. (ladysthumb, POLPE), Polygonum
hydropiperoides Michx. (POLHP, mild smartweed), Rotala indica
(Willd.) Koehne (Indian toothcup, ROTIN), Sagittaria species,
(arrowhead, SAGSS), Sesbania exaltata (Raf.) Cory/Rydb. Ex Hill
(hemp sesbania, SEBEX), or Sphenoclea zeylanica Gaertn. (gooseweed,
SPDZE).
[0107] In some embodiments, the methods provided herein are
utilized to control undesirable vegetation in cereals. In certain
embodiments, the undesirable vegetation is Alopecurus myosuroides
Huds. (blackgrass, ALOMY), Apera spica-venti (L.) Beauv.
(windgrass, APESV), Avena fatua L. (wild oat, AVEFA), Bromus
tectorum L. (downy brome, BROTE), Lolium multiflorum Lam. (Italian
ryegrass, LOLMU), Phalaris minor Retz. (littleseed canarygrass,
PHAMI), Poa annua L. (annual bluegrass, POANN), Setaria pumila
(Poir.) Roemer & J. A. Schultes (yellow foxtail, SETLU),
Setaria viridis (L.) Beauv. (green foxtail, SETVI), Amaranthus
retroflexus L. (redroot pigweed, AMARE), Brassica species (BRSSS),
Chenopodium album L. (common lambsquarters, CHEAL), Cirsium arvense
(L.) Scop. (Canada thistle, CIRAR), Galium aparine L. (catchweed
bedstraw, GALAP), Kochia scoparia (L.) Schrad. (kochia, KCHSC),
Lamium purpureum L. (purple deadnettle, LAMPU), Matricaria recutita
L. (wild chamomile, MATCH), Matricaria matricarioides (Less.)
Porter (pineappleweed, MATMT), Papaver rhoeas L. (common poppy,
PAPRH), Polygonum convolvulus L. (wild buckwheat, POLCO), Salsola
tragus L. (Russian thistle, SASKR), Sinapis species (SINSS),
Sinapis arvensis L. (wild mustard, SINAR), Stellaria media (L.)
Vill. (common chickweed, STEME), Veronica persica Poir. (Persian
speedwell, VERPE), Viola arvensis Murr. (field violet, VIOAR), or
Viola tricolor L. (wild violet, VIOTR).
[0108] In some embodiments, the methods provided herein are
utilized to control undesirable vegetation in range and pasture,
fallowland, IVM and ROW. In certain embodiments, the undesirable
vegetation is Ambrosia artemisiifolia L. (common ragweed, AMBEL),
Cassia obtusifolia (sickle pod, CASOB), Centaurea maculosa auct.
non Lam. (spotted knapweed, CENMA), Cirsium arvense (L.) Scop.
(Canada thistle, CIRAR), Convolvulus arvensis L. (field bindweed,
CONAR), Euphorbia esula L. (leafy spurge, EPHES), Lactuca serriola
L./Torn. (prickly lettuce, LACSE), Plantago lanceolata L. (buckhorn
plantain, PLALA), Rumex obtusifolius L. (broadleaf dock, RUMOB),
Sida spinosa L. (prickly sida, SIDSP), Sinapis arvensis L. (wild
mustard, SINAR), Sonchus arvensis L. (perennial sowthistle, SONAR),
Solidago species (goldenrod, SOOSS), Taraxacum officinale G. H.
Weber ex Wiggers (dandelion, TAROF), Trifolium repens L. (white
clover, TRFRE), or Urtica dioica L. (common nettle, URTDI).
[0109] In some embodiments, the methods provided herein are
utilized to control undesirable vegetation found in row crops, tree
and vine crops, and perennial crops. In certain embodiments, the
undesirable vegetation is Alopecurus myosuroides Huds. (blackgrass,
ALOMY), Avena fatua L. (wild oat, AVEFA), Brachiaria decumbens
Stapf. or Urochloa decumbens (Stapf) R. D. Webster (Surinam grass,
BRADC), Brachiaria brizantha (Hochst. ex A. Rich.) Stapf. or
Urochloa brizantha (Hochst. ex A. Rich.) R. D. (beard grass,
BRABR), Brachiaria platyphylla (Groseb.) Nash or Urochloa
platyphylla (Nash) R. D. Webster (broadleaf signalgrass, BRAPP),
Brachiaria plantaginea (Link) Hitchc. or Urochloa plantaginea
(Link) R. D. Webster (alexandergrass, BRAPL), Cenchrus echinatus L.
(southern sandbar, CENEC), Digitaria horizontalis Willd. (Jamaican
crabgrass, DIGHO), Digitaria insularis (L.) Mez ex Ekman
(sourgrass, TRCIN), Digitaria sanguinalis (L.) Scop. (large
crabgrass, DIGSA), Echinochloa crus-galli (L.) P. Beauv.
(barnyardgrass, ECHCG), Echinochloa colonum (L.) Link (junglerice,
ECHCO), Eleusine indica (L.) Gaertn. (goosegrass, ELEIN), Lolium
multiflorum Lam. (Italian ryegrass, LOLMU), Panicum dichotomiflorum
Michx. (fall panicum, PANDI), Panicum miliaceum L. (wild-proso
millet, PANMI), Setaria faberi Herrm. (giant foxtail, SETFA),
Setaria viridis (L.) Beauv. (green foxtail, SETVI), Sorghum
halepense (L.) Pers. (Johnsongrass, SORHA), Sorghum bicolor (L.)
Moench ssp. Arundinaceum (shattercane, SORVU), Cyperus esculentus
L. (yellow nutsedge, CYPES), Cyperus rotundus L. (purple nutsedge,
CYPRO), Abutilon theophrasti Medik. (velvetleaf, ABUTH), Amaranthus
species (pigweeds and amaranths, AMASS), Ambrosia artemisiifolia L.
(common ragweed, AMBEL), Ambrosia psilostachya DC. (western
ragweed, AMBPS), Ambrosia trifida L. (giant ragweed, AMBTR), Anoda
cristata (L.) Schlecht. (spurred anoda, ANVCR), Asclepias syriaca
L. (common milkweed, ASCSY), Bidens pilosa L. (hairy beggarticks,
BIDPI), Borreria species (BOISS), Borreria alata (Aubl.) DC. or
Spermacoce alata Aubl. (broadleaf buttonweed, BOILF), Spermacose
latifolia (broadleaved button weed, BOILF), Chenopodium album L.
(common lambsquarters, CHEAL), Cirsium arvense (L.) Scop. (Canada
thistle, CIRAR), Commelina benghalensis L. (tropical spiderwort,
COMBE), Datura stramonium L. (jimsonweed, DATST), Daucus carota L.
(wild carrot, DAUCA), Euphorbia heterophylla L. (wild poinsettia,
EPHHL), Euphorbia hirta L. or Chamaesyce hirta (L.) Millsp. (garden
spurge, EPHHI), Euphorbia dentata Michx. (toothed spurge, EPHDE),
Erigeron bonariensis L. or Conyza bonariensis (L.) Cronq. (hairy
fleabane, ERIBO), Erigeron canadensis L. or Conyza canadensis (L.)
Cronq. (Canadian fleabane, ERICA), Conyza sumatrensis (Retz.) E. H.
Walker (tall fleabane, ERIFL), Helianthus annuus L. (common
sunflower, HELAN), Jacquemontia tamnifolia (L.) Griseb.
(smallflower morningglory, IAQTA), Ipomoea hederacea (L.) Jacq.
(ivyleaf morningglory, IPOHE), Ipomoea lacunosa L. (white
morningglory, IPOLA), Lactuca serriola L./Torn. (prickly lettuce,
LACSE), Portulaca oleracea L. (common purslane, POROL), Richardia
species (pusley, RCHSS), Sida species (sida, SIDSS), Sida spinosa
L. (prickly sida, SIDSP), Sinapis arvensis L. (wild mustard,
SINAR), Solanum ptychanthum Dunal (eastern black nightshade,
SOLPT), Tridax procumbens L. (coat buttons, TRQPR), or Xanthium
strumarium L. (common cocklebur, XANST).
[0110] In some embodiments, the methods provided herein are
utilized to control undesirable vegetation in turf. In certain
embodiments, the undesirable vegetation is Bellis perennis L.
(English daisy, BELPE), Cyperus esculentus L. (yellow nutsedge,
CYPES), Cyperus species (CYPSS), Digitaria sanguinalis (L.) Scop.
(large crabgrass, DIGSA), Diodia virginiana L. (Virginia
buttonweed, DIQVI), Euphorbia species (spurge, EPHSS), Glechoma
hederacea L. (ground ivy, GLEHE), Hydrocotyle umbellata L.
(dollarweed, HYDUM), Kyllinga species (kyllinga, KYLSS), Lamium
amplexicaule L. (henbit, LAMAM), Murdannia nudiflora (L.) Brenan
(doveweed, MUDNU), Oxalis species (woodsorrel, OXASS), Plantago
major L. (broadleaf plantain, PLAMA), Plantago lanceolata L.
(buckhorn/narrowleaf plantain, PLALA), Phyllanthus urinaria L.
(chamberbitter, PYLTE), Rumex obtusifolius L. (broadleaf dock,
RUMOB), Stachys floridana Shuttlew. (Florida betony, STAFL),
Stellaria media (L.) Vill. (common chickweed, STEME), Taraxacum
officinale G. H. Weber ex Wiggers (dandelion, TAROF), Trifolium
repens L. (white clover, TRFRE), or Viola species (wild violet,
VIOSS).
[0111] In some embodiments, the compositions and methods provided
herein are utilized to control undesirable vegetation consisting of
grass, broadleaf and sedge weeds. In certain embodiments, the
compositions and methods provided herein are utilized to control
undesirable grass, broadleaf and sedge vegetation including but not
limited to Brachiaria/Uroichloa, Cyperus, Digitaria, Echinochloa,
Fimbristylis, Ipomoea, Leptochloa, and Schoenoplectus.
[0112] In some embodiments, the combination of compound (I) or
agriculturally acceptable ester or salt thereof and fungicides are
used to control, including but not limited to, broadleaf
signalgrass (Brachiaria platyphylla (Groseb.) Nash), yellow
nutsedge (Cyperus esculentus L.), rice flatsedge (Cyperus iria L.),
purple nutsedge (Cyperus rotundus), large crabgrass (Digitaria
sanguinalis), barnyardgrass (Echinochloa crus-galli), jungle rice
(Echinochloa colona), watergrass (Echinochloa oryzoides), globe
fringerush (Fimbristylis miliacea (L.) Vahl), ivyleaf morningglory
(Ipomoea hederacea), Chinese sprangletop (Leptochloa chinensis) and
Japanese bulrush (Schoenoplectus juncoides).
[0113] The compounds of formula I or agriculturally acceptable salt
or ester thereof may be used to control herbicide resistant or
tolerant weeds. The methods employing the combination of a compound
of formula I or agriculturally acceptable salt or ester thereof and
the compositions described herein may also be employed to control
herbicide resistant or tolerant weeds. Exemplary resistant or
tolerant weeds include, but are not limited to, biotypes resistant
or tolerant to acetolactate synthase (ALS) or acetohydroxy acid
synthase (AHAS) inhibitors (e.g., imidazolinones, sulfonylureas,
pyrimidinylthiobenzoates, triazolopyrimidines,
sulfonylaminocarbonyltriazolinones), photosystem II inhibitors
(e.g., phenylcarbamates, pyridazinones, triazines, triazinones,
uracils, amides, ureas, benzothiadiazinones, nitriles,
phenylpyridazines), acetyl CoA carboxylase (ACCase) inhibitors
(e.g., aryloxyphenoxypropionates, cyclohexanediones,
phenylpyrazolines), synthetic auxins (e.g., benzoic acids,
phenoxycarboxylic acids, pyridine carboxylic acids, quinoline
carboxylic acids), auxin transport inhibitors (e.g., phthalamates,
semicarbazones), photosystem I inhibitors (e.g., bipyridyliums),
5-enolpyruvylshikimate-3-phosphate (EPSP) synthase inhibitors
(e.g., glyphosate), glutamine synthetase inhibitors (e.g.,
glufosinate, bialafos), microtubule assembly inhibitors (e.g.,
benzamides, benzoic acids, dinitroanilines, phosphoramidates,
pyridines), mitosis inhibitors (e.g., carbamates), very long chain
fatty acid (VLCFA) inhibitors (e.g., acetamides, chloroacetamides,
oxyacetamides, tetrazolinones), fatty acid and lipid synthesis
inhibitors (e.g., phosphorodithioates, thiocarbamates,
benzofuranes, chlorocarbonic acids), protoporphyrinogen oxidase
(PPO) inhibitors (e.g., diphenylethers, N-phenylphthalimides,
oxadiazoles, oxazolidinediones, phenylpyrazoles, pyrimidindiones,
thiadiazoles, triazolinones), carotenoid biosynthesis inhibitors
(e.g., clomazone, amitrole, aclonifen), phytoene desaturase (PDS)
inhibitors (e.g., amides, anilidex, furanones, phenoxybutan-amides,
pyridiazinones, pyridines), 4-hydroxyphenyl-pyruvate-dioxygenase
(HPPD) inhibitors (e.g., callistemones, isoxazoles, pyrazoles,
triketones), cellulose biosynthesis inhibitors (e.g., nitriles,
benzamides, quinclorac, triazolocarboxamides), herbicides with
multiple modes-of-action such as quinclorac, and unclassified
herbicides such as arylaminopropionic acids, difenzoquat,
endothall, and organoarsenicals. Exemplary resistant or tolerant
weeds include, but are not limited to, biotypes with resistance or
tolerance to multiple herbicides, biotypes with resistance or
tolerance to multiple chemical classes, and biotypes with
resistance or tolerance to multiple herbicide modes-of-action, and
biotypes with multiple resistance or tolerance mechanisms (e.g.,
target site resistance or metabolic resistance).
[0114] In certain embodiments of the compositions and methods
described herein, the compound of formula (I) or salt or ester
thereof is used in combination with azoxystrobin. With respect to
the compositions, in some embodiments, the weight ratio of the
compound of formula (I) or salt or ester thereof to azoxystrobin is
within the range of from about 1:500 to about 12:1. In certain
embodiments, the weight ratio of the compound of formula (I) or
salt or ester thereof to azoxystrobin is within the range of from
about 1:57 to about 1:2. With respect to the methods, in certain
embodiments, the methods comprise contacting the undesirable
vegetation or locus thereof or applying to the soil or water to
prevent the emergence or growth of vegetation a composition
described herein. In some embodiments, the composition is applied
at an application rate of from about 27 grams active ingredient per
hectare (gai/ha) to about 1300 gai/ha based on the total amount of
active ingredients in the composition. In certain embodiments, the
composition is applied at an application rate of from about 66
grams active ingredient per hectare (gai/ha) to about 300 gai/ha
based on the total amount of active ingredients in the composition.
In some embodiments, the methods comprise contacting the
undesirable vegetation or locus thereof or applying to the soil or
water to prevent the emergence or growth of vegetation with a
compound of formula (I) or salt or ester thereof and azoxystrobin,
e.g., sequentially or simultaneously. In some embodiments,
azoxystrobin is applied at a rate from about 25 gai/ha to about
1000 gai/ha and the compound of formula (I) of salt or ester
thereof is applied at a rate from about 2 gae/ha to about 300
gae/ha. In some embodiments, azoxystrobin is applied at a rate from
about 62 gai/ha to about 250 gai/ha and the compound of formula (I)
of salt or ester thereof is applied at a rate from about 4 g acid
equivalent per hectare (gae/ha) to about 32 gae/ha. In certain
embodiments, the methods utilize the compound of formula (I), or
its benzyl ester and azoxystrobin. In one embodiment, the methods
utilize the compound of formula (I) and azoxystrobin, wherein the
compound of formula (I) is applied at a rate of from about 3 g acid
equivalent per hectare (gae/ha) to about 200 gae/ha, and
azoxystrobin is applied at a rate of about 30 gai/ha to about 900
gai/ha. In one embodiment, the methods utilize the benzyl ester of
the compound of formula (I) and azoxystrobin, wherein the benzyl
ester of the compound of formula (I) is applied at a rate of from
about 4.4 g acid equivalent per hectare (gae/ha) to about 32
gae/ha, and azoxystrobinis applied at a rate of about 62 gai/ha to
about 250 gai/ha.
[0115] In certain embodiments of the compositions and methods
described herein, the compound of formula (I) or salt or ester
thereof is used in combination with carbendazim. With respect to
the compositions, in some embodiments, the weight ratio of the
compound of formula (I) or salt or ester thereof to carbendazim is
within the range of from about 1:375 to about 12:1. In certain
embodiments, the weight ratio of the compound of formula (I) or
salt or ester thereof to carbendazim is within the range of from
about 1:31 to about 1:4. With respect to the methods, in certain
embodiments, the methods comprise contacting the undesirable
vegetation or locus thereof or applying to the soil or water to
prevent the emergence or growth of vegetation a composition
described herein. In some embodiments, the composition is applied
at an application rate of from about 27 grams active ingredient per
hectare (gai/ha) to about 1,050 gai/ha based on the total amount of
active ingredients in the composition. In certain embodiments, the
composition is applied at an application rate of from about 133
grams active ingredient per hectare (gai/ha) to about 282 gai/ha
based on the total amount of active ingredients in the composition.
In some embodiments, the methods comprise contacting the
undesirable vegetation or locus thereof or applying to the soil or
water to prevent the emergence or growth of vegetation with a
compound of formula (I) or salt or ester thereof and carbendazim,
e.g., sequentially or simultaneously. In some embodiments,
carbendazimis applied at a rate from about 25 gai/ha to about 750
gai/ha and the compound of formula (I) of salt or ester thereof is
applied at a rate from about 2 gae/ha to about 300 gae/ha. In some
embodiments, carbendazim is applied at a rate from about 50 gai/ha
to about 600 gai/ha and the compound of formula (I) of salt or
ester thereof is applied at a rate from about 3 g acid equivalent
per hectare (gae/ha) to about 200 gae/ha. In certain embodiments,
the methods utilize the compound of formula (I), or its benzyl
ester and carbendazim. In one embodiment, the methods utilize the
compound of formula (I) and carbendazim, wherein the compound of
formula (I) is applied at a rate of from about 3 g acid equivalent
per hectare (gae/ha) to about 200 gae/ha, and carbendazim is
applied at a rate of about 50 gai/ha to about 600 gai/ha. In one
embodiment, the methods utilize the benzyl ester of the compound of
formula (I) and carbendazim wherein the benzyl ester of the
compound of formula (I) is applied at a rate of from about 8 g acid
equivalent per hectare (gae/ha) to about 32 gae/ha, and carbendazim
is applied at a rate of about 125 gai/ha to about 250 gai/ha.
[0116] In certain embodiments of the compositions and methods
described herein, the compound of formula (I) or salt or ester
thereof is used in combination with difenoconazole. With respect to
the compositions, in some embodiments, the weight ratio of the
compound of formula (I) or salt or ester thereof to difenoconazole
is within the range of from about 1:250 to about 2:1. In certain
embodiments, the weight ratio of the compound of formula (I) or
salt or ester thereof to difenoconazoleis within the range of from
about 1:46 to about 1:1.5. With respect to the methods, in certain
embodiments, the methods comprise contacting the undesirable
vegetation or locus thereof or applying to the soil or water to
prevent the emergence or growth of vegetation a composition
described herein. In some embodiments, the composition is applied
at an application rate of from about 27 grams active ingredient per
hectare (gai/ha) to about 800 gai/ha based on the total amount of
active ingredients in the composition. In certain embodiments, the
composition is applied at an application rate of from about 54
grams active ingredient per hectare (gai/ha) to about 250 gai/ha
based on the total amount of active ingredients in the composition.
In some embodiments, the methods comprise contacting the
undesirable vegetation or locus thereof or applying to the soil or
water to prevent the emergence or growth of vegetation with a
compound of formula (I) or salt or ester thereof and
difenoconazole, e.g., sequentially or simultaneously. In some
embodiments, difenoconazole is applied at a rate from about 25
gai/ha to about 500 gai/ha and the compound of formula (I) of salt
or ester thereof is applied at a rate from about 2 gae/ha to about
300 gae/ha. In some embodiments, difenoconazole is applied at a
rate from about 50 gai/ha to about 200 gai/ha and the compound of
formula (I) of salt or ester thereof is applied at a rate from
about 8 g acid equivalent per hectare (gae/ha) to about 32 gae/ha.
In certain embodiments, the methods utilize the compound of formula
(I), or its benzyl ester and difenoconazole. In one embodiment, the
methods utilize the compound of formula (I) and difenoconazole,
wherein the compound of formula (I) is applied at a rate of from
about 3 g acid equivalent per hectare (gae/ha) to about 200 gae/ha,
and difenoconazole is applied at a rate of about 30 gai/ha to about
450 gai/ha. In one embodiment, the methods utilize the benzyl ester
of the compound of formula (I) and difenoconazole, wherein the
benzyl ester of the compound of formula (I) is applied at a rate of
from about 8 g acid equivalent per hectare (gae/ha) to about 32
gae/ha, and difenoconazoleis applied at a rate of about 50 gai/ha
to about 200 gai/ha.
[0117] In certain embodiments of the compositions and methods
described herein, the compound of formula (I) or salt or ester
thereof is used in combination with flutolanil. With respect to the
compositions, in some embodiments, the weight ratio of the compound
of formula (I) or salt or ester thereof to flutolanil is within the
range of from about 1:500 to about 12:1. In certain embodiments,
the weight ratio of the compound of formula (I) or salt or ester
thereof to flutolanil is within the range of from about 1:70 to
about 1:4. With respect to the methods, in certain embodiments, the
methods comprise contacting the undesirable vegetation or locus
thereof or applying to the soil or water to prevent the emergence
or growth of vegetation a composition described herein. In some
embodiments, the composition is applied at an application rate of
from about 27 grams active ingredient per hectare (gai/ha) to about
1,300 gai/ha based on the total amount of active ingredients in the
composition. In certain embodiments, the composition is applied at
an application rate of from about 148 grams active ingredient per
hectare (gai/ha) to about 592 gai/ha based on the total amount of
active ingredients in the composition. In some embodiments, the
methods comprise contacting the undesirable vegetation or locus
thereof or applying to the soil or water to prevent the emergence
or growth of vegetation with a compound of formula (I) or salt or
ester thereof and flutolanil, e.g., sequentially or simultaneously.
In some embodiments, flutolanil is applied at a rate from about 25
gai/ha to about 1,000 gai/ha and the compound of formula (I) of
salt or ester thereof is applied at a rate from about 2 gae/ha to
about 300 gae/ha. In some embodiments, flutolanil is applied at a
rate from about 50 gai/ha to about 900 gai/ha and the compound of
formula (I) of salt or ester thereof is applied at a rate from
about 3 g acid equivalent per hectare (gae/ha) to about 200 gae/ha.
In certain embodiments, the methods utilize the compound of formula
(I), or its benzyl ester and flutolanil. In one embodiment, the
methods utilize the compound of formula (I) and flutolanil, wherein
the compound of formula (I) is applied at a rate of from about 3 g
acid equivalent per hectare (gae/ha) to about 200 gae/ha, and
flutolanil is applied at a rate of about 50 gai/ha to about 900
gai/ha. In one embodiment, the methods utilize the benzyl ester of
the compound of formula (I) and flutolanil, wherein the benzyl
ester of the compound of formula (I) is applied at a rate of from
about 8 g acid equivalent per hectare (gae/ha) to about 32 gae/ha,
and flutolanil is applied at a rate of about 140 gai/ha to about
560 gai/ha.
[0118] In certain embodiments of the compositions and methods
described herein, the compound of formula (I) or salt or ester
thereof is used in combination with hexaconazole. With respect to
the compositions, in some embodiments, the weight ratio of the
compound of formula (I) or salt or ester thereof to hexaconazole is
within the range of from about 1:250 to about 60:1. In certain
embodiments, the weight ratio of the compound of formula (I) or
salt or ester thereof to hexaconazole is within the range of from
about 1:12.5 to about 1.25:1. With respect to the methods, in
certain embodiments, the methods comprise contacting the
undesirable vegetation or locus thereof or applying to the soil or
water to prevent the emergence or growth of vegetation a
composition described herein. In some embodiments, the composition
is applied at an application rate of from about 7 grams active
ingredient per hectare (gai/ha) to about 800 gai/ha based on the
total amount of active ingredients in the composition. In certain
embodiments, the composition is applied at an application rate of
from about 33 grams active ingredient per hectare (gai/ha) to about
150 gai/ha based on the total amount of active ingredients in the
composition. In some embodiments, the methods comprise contacting
the undesirable vegetation or locus thereof or applying to the soil
or water to prevent the emergence or growth of vegetation with a
compound of formula (I) or salt or ester thereof and hexaconazole,
e.g., sequentially or simultaneously. In some embodiments,
hexaconazole is applied at a rate from about 5 gai/ha to about 500
gai/ha and the compound of formula (I) of salt or ester thereof is
applied at a rate from about 2 gae/ha to about 300 gae/ha. In some
embodiments, hexaconazole is applied at a rate from about 25 gai/ha
to about 100 gai/ha and the compound of formula (I) of salt or
ester thereof is applied at a rate from about 8 g acid equivalent
per hectare (gae/ha) to about 32 gae/ha. In certain embodiments,
the methods utilize the compound of formula (I), or its benzyl
ester and hexaconazole. In one embodiment, the methods utilize the
compound of formula (I) and hexaconazole, wherein the compound of
formula (I) is applied at a rate of from about 3 g acid equivalent
per hectare (gae/ha) to about 200 gae/ha, and hexaconazole is
applied at a rate of about 7 gai/ha to about 475 gai/ha. In one
embodiment, the methods utilize the benzyl ester of the compound of
formula (I) and hexaconazole, wherein the benzyl ester of the
compound of formula (I) is applied at a rate of from about 8 g acid
equivalent per hectare (gae/ha) to about 32 gae/ha, and
hexaconazole is applied at a rate of about 25 gai/ha to about 100
gai/ha.
[0119] In certain embodiments of the compositions and methods
described herein, the compound of formula (I) or salt or ester
thereof is used in combination with iprobenfos. With respect to the
compositions, in some embodiments, the weight ratio of the compound
of formula (I) or salt or ester thereof to iprobenfosis within the
range of from about 1:1,000 to about 3:1. In certain embodiments,
the weight ratio of the compound of formula (I) or salt or ester
thereof to iprobenfos is within the range of from about 1:600 to
about 1:1. With respect to the methods, in certain embodiments, the
methods comprise contacting the undesirable vegetation or locus
thereof or applying to the soil or water to prevent the emergence
or growth of vegetation a composition described herein. In some
embodiments, the composition is applied at an application rate of
from about 102 grams active ingredient per hectare (gai/ha) to
about 2,300 gai/ha based on the total amount of active ingredients
in the composition. In certain embodiments, the composition is
applied at an application rate of from about 113 grams active
ingredient per hectare (gai/ha) to about 1,950 gai/ha based on the
total amount of active ingredients in the composition. In some
embodiments, the methods comprise contacting the undesirable
vegetation or locus thereof or applying to the soil or water to
prevent the emergence or growth of vegetation with a compound of
formula (I) or salt or ester thereof and iprobenfos, e.g.,
sequentially or simultaneously. In some embodiments, iprobenfos is
applied at a rate from about 100 gai/ha to about 2,000 gai/ha and
the compound of formula (I) of salt or ester thereof is applied at
a rate from about 2 gae/ha to about 300 gae/ha. In some
embodiments, iprobenfos is applied at a rate from about 200 gai/ha
to about 1,900 gai/ha and the compound of formula (I) of salt or
ester thereof is applied at a rate from about 3 g acid equivalent
per hectare (gae/ha) to about 200 gae/ha. In certain embodiments,
the methods utilize the compound of formula (I), or its benzyl
ester and iprobenfos. In one embodiment, the methods utilize the
compound of formula (I) and iprobenfos wherein the compound of
formula (I) is applied at a rate of from about 3 g acid equivalent
per hectare (gae/ha) to about 200 gae/ha, and iprobenfos is applied
at a rate of about 200 gai/ha to about 1,900 gai/ha. In one
embodiment, the methods utilize the benzyl ester of the compound of
formula (I) and iprobenfos, wherein the benzyl ester of the
compound of formula (I) is applied at a rate of from about 3 g acid
equivalent per hectare (gae/ha) to about 150 gae/ha, and
iprobenfosis applied at a rate of about 110 gai/ha to about 1,800
gai/ha.
[0120] In certain embodiments of the compositions and methods
described herein, the compound of formula (I) or salt or ester
thereof is used in combination with isoprothiolane. With respect to
the compositions, in some embodiments, the weight ratio of the
compound of formula (I) or salt or ester thereof to isoprothiolane
is within the range of from about 1:500 to about 6:1. In certain
embodiments, the weight ratio of the compound of formula (I) or
salt or ester thereof to isoprothiolane is within the range of from
about 1:300 to about 2:1. With respect to the methods, in certain
embodiments, the methods comprise contacting the undesirable
vegetation or locus thereof or applying to the soil or water to
prevent the emergence or growth of vegetation a composition
described herein. In some embodiments, the composition is applied
at an application rate of from about 52 grams active ingredient per
hectare (gai/ha) to about 1,300 gai/ha based on the total amount of
active ingredients in the composition. In certain embodiments, the
composition is applied at an application rate of from about 100
grams active ingredient per hectare (gai/ha) to about 1,100 gai/ha
based on the total amount of active ingredients in the composition.
In some embodiments, the methods comprise contacting the
undesirable vegetation or locus thereof or applying to the soil or
water to prevent the emergence or growth of vegetation with a
compound of formula (I) or salt or ester thereof and
isoprothiolane, e.g., sequentially or simultaneously. In some
embodiments, isoprothiolane is applied at a rate from about 50
gai/ha to about 1,000 gai/ha and the compound of formula (I) of
salt or ester thereof is applied at a rate from about 2 gae/ha to
about 300 gae/ha. In some embodiments, isoprothiolane is applied at
a rate from about 75 gai/ha to about 950 gai/ha and the compound of
formula (I) of salt or ester thereof is applied at a rate from
about 3 g acid equivalent per hectare (gae/ha) to about 200 gae/ha.
In certain embodiments, the methods utilize the compound of formula
(I), or its benzyl ester and isoprothiolane. In one embodiment, the
methods utilize the compound of formula (I) and isoprothiolane,
wherein the compound of formula (I) is applied at a rate of from
about 3 g acid equivalent per hectare (gae/ha) to about 200 gae/ha,
and isoprothiolane is applied at a rate of about 75 gai/ha to about
950 gai/ha. In one embodiment, the methods utilize the benzyl ester
of the compound of formula (I) and isoprothiolane, wherein the
benzyl ester of the compound of formula (I) is applied at a rate of
from about 3 g acid equivalent per hectare (gae/ha) to about 150
gae/ha, and isoprothiolane is applied at a rate of about 70 gai/ha
to about 900 gai/ha.
[0121] In certain embodiments of the compositions and methods
described herein, the compound of formula (I) or salt or ester
thereof is used in combination with isotianil. With respect to the
compositions, in some embodiments, the weight ratio of the compound
of formula (I) or salt or ester thereof to isotianilis within the
range of from about 1:500 to about 30:1. In certain embodiments,
the weight ratio of the compound of formula (I) or salt or ester
thereof to isotianil is within the range of from about 1:48 to
about 1:3. With respect to the methods, in certain embodiments, the
methods comprise contacting the undesirable vegetation or locus
thereof or applying to the soil or water to prevent the emergence
or growth of vegetation a composition described herein. In some
embodiments, the composition is applied at an application rate of
from about 12 grams active ingredient per hectare (gai/ha) to about
1,300 gai/ha based on the total amount of active ingredients in the
composition. In certain embodiments, the composition is applied at
an application rate of from about 108 grams active ingredient per
hectare (gai/ha) to about 420 gai/ha based on the total amount of
active ingredients in the composition. In some embodiments, the
methods comprise contacting the undesirable vegetation or locus
thereof or applying to the soil or water to prevent the emergence
or growth of vegetation with a compound of formula (I) or salt or
ester thereof and isotianil, e.g., sequentially or simultaneously.
In some embodiments, isotianil is applied at a rate from about 10
gai/ha to about 1,000 gai/ha and the compound of formula (I) of
salt or ester thereof is applied at a rate from about 2 gae/ha to
about 300 gae/ha. In some embodiments, isotianil is applied at a
rate from about 25 gai/ha to about 380 gai/ha and the compound of
formula (I) of salt or ester thereof is applied at a rate from
about 8 g acid equivalent per hectare (gae/ha) to about 32 gae/ha.
In certain embodiments, the methods utilize the compound of formula
(I), or its benzyl ester and isotianil. In one embodiment, the
methods utilize the compound of formula (I) and isotianil, wherein
the compound of formula (I) is applied at a rate of from about 3 g
acid equivalent per hectare (gae/ha) to about 200 gae/ha, and
isotianil is applied at a rate of about 25 gai/ha to about 700
gai/ha. In one embodiment, the methods utilize the benzyl ester of
the compound of formula (I) and isotianil, wherein the benzyl ester
of the compound of formula (I) is applied at a rate of from about 8
g acid equivalent per hectare (gae/ha) to about 32 gae/ha, and
isotianil is applied at a rate of about 100 gai/ha to about 380
gai/ha.
[0122] In certain embodiments of the compositions and methods
described herein, the compound of formula (I) or salt or ester
thereof is used in combination with kasugamycin. With respect to
the compositions, in some embodiments, the weight ratio of the
compound of formula (I) or salt or ester thereof to kasugamycin is
within the range of from about 1:250 to about 150:1. In certain
embodiments, the weight ratio of the compound of formula (I) or
salt or ester thereof to kasugamycin is within the range of from
about 1:9 to about 2:1. With respect to the methods, in certain
embodiments, the methods comprise contacting the undesirable
vegetation or locus thereof or applying to the soil or water to
prevent the emergence or growth of vegetation a composition
described herein. In some embodiments, the composition is applied
at an application rate of from about 4 grams active ingredient per
hectare (gai/ha) to about 800 gai/ha based on the total amount of
active ingredients in the composition. In certain embodiments, the
composition is applied at an application rate of from about 25
grams active ingredient per hectare (gai/ha) to about 105 gai/ha
based on the total amount of active ingredients in the composition.
In some embodiments, the methods comprise contacting the
undesirable vegetation or locus thereof or applying to the soil or
water to prevent the emergence or growth of vegetation with a
compound of formula (I) or salt or ester thereof and kasugamycin,
e.g., sequentially or simultaneously. In some embodiments,
kasugamycin is applied at a rate from about 2 gai/ha to about 500
gai/ha and the compound of formula (I) of salt or ester thereof is
applied at a rate from about 2 gae/ha to about 300 gae/ha. In some
embodiments, kasugamycin is applied at a rate from about 4 gai/ha
to about 450 gai/ha and the compound of formula (I) of salt or
ester thereof is applied at a rate from about 3 g acid equivalent
per hectare (gae/ha) to about 200 gae/ha. In certain embodiments,
the methods utilize the compound of formula (I), or its benzyl
ester and kasugamycin. In one embodiment, the methods utilize the
compound of formula (I) and kasugamycin wherein the compound of
formula (I) is applied at a rate of from about 3 g acid equivalent
per hectare (gae/ha) to about 200 gae/ha, and kasugamycin is
applied at a rate of about 4 gai/ha to about 450 gai/ha. In one
embodiment, the methods utilize the benzyl ester of the compound of
formula (I) and kasugamycin, wherein the benzyl ester of the
compound of formula (I) is applied at a rate of from about 8 g acid
equivalent per hectare (gae/ha) to about 32 gae/ha, and kasugamycin
is applied at a rate of about 17.5 gai/ha to about 70 gai/ha.
[0123] In certain embodiments of the compositions and methods
described herein, the compound of formula (I) or salt or ester
thereof is used in combination with mancozeb. With respect to the
compositions, in some embodiments, the weight ratio of the compound
of formula (I) or salt or ester thereof to mancozeb is within the
range of from about 1:2,500 to about 12:1. In certain embodiments,
the weight ratio of the compound of formula (I) or salt or ester
thereof to mancozebis within the range of from about 1:210 to about
1:26. With respect to the methods, in certain embodiments, the
methods comprise contacting the undesirable vegetation or locus
thereof or applying to the soil or water to prevent the emergence
or growth of vegetation a composition described herein. In some
embodiments, the composition is applied at an application rate of
from about 27 grams active ingredient per hectare (gai/ha) to about
5,300 gai/ha based on the total amount of active ingredients in the
composition. In certain embodiments, the composition is applied at
an application rate of from about 848 grams active ingredient per
hectare (gai/ha) to about 1,712 gai/ha based on the total amount of
active ingredients in the composition. In some embodiments, the
methods comprise contacting the undesirable vegetation or locus
thereof or applying to the soil or water to prevent the emergence
or growth of vegetation with a compound of formula (I) or salt or
ester thereof and mancozeb, e.g., sequentially or simultaneously.
In some embodiments, mancozebis applied at a rate from about 25
gai/ha to about 5,000 gai/ha and the compound of formula (I) of
salt or ester thereof is applied at a rate from about 2 gae/ha to
about 300 gae/ha. In some embodiments, mancozeb is applied at a
rate from about 50 gai/ha to about 4,500 gai/ha and the compound of
formula (I) of salt or ester thereof is applied at a rate from
about 3 g acid equivalent per hectare (gae/ha) to about 200 gae/ha.
In certain embodiments, the methods utilize the compound of formula
(I), or its benzyl ester and mancozeb. In one embodiment, the
methods utilize the compound of formula (I) and mancozeb, wherein
the compound of formula (I) is applied at a rate of from about 3 g
acid equivalent per hectare (gae/ha) to about 200 gae/ha, and
mancozeb is applied at a rate of about 50 gai/ha to about 4,500
gai/ha. In one embodiment, the methods utilize the benzyl ester of
the compound of formula (I) and mancozeb, wherein the benzyl ester
of the compound of formula (I) is applied at a rate of from about 8
g acid equivalent per hectare (gae/ha) to about 32 gae/ha, and
mancozeb is applied at a rate of about 840 gai/ha to about 1,680
gai/ha.
[0124] In certain embodiments of the compositions and methods
described herein, the compound of formula (I) or salt or ester
thereof is used in combination with myclobutanil. With respect to
the compositions, in some embodiments, the weight ratio of the
compound of formula (I) or salt or ester thereof to myclobutanil is
within the range of from about 1:250 to about 12:1. In certain
embodiments, the weight ratio of the compound of formula (I) or
salt or ester thereof to myclobutanil is within the range of from
about 1:38 to about 1:1.5. With respect to the methods, in certain
embodiments, the methods comprise contacting the undesirable
vegetation or locus thereof or applying to the soil or water to
prevent the emergence or growth of vegetation a composition
described herein. In some embodiments, the composition is applied
at an application rate of from about 22 grams active ingredient per
hectare (gai/ha) to about 800 gai/ha based on the total amount of
active ingredients in the composition. In certain embodiments, the
composition is applied at an application rate of from about 55
grams active ingredient per hectare (gai/ha) to about 232 gai/ha
based on the total amount of active ingredients in the composition.
In some embodiments, the methods comprise contacting the
undesirable vegetation or locus thereof or applying to the soil or
water to prevent the emergence or growth of vegetation with a
compound of formula (I) or salt or ester thereof and myclobutanil,
e.g., sequentially or simultaneously. In some embodiments,
myclobutanil is applied at a rate from about 25 gai/ha to about 500
gai/ha and the compound of formula (I) of salt or ester thereof is
applied at a rate from about 2 gae/ha to about 300 gae/ha. In some
embodiments, myclobutanil is applied at a rate from about 50 gai/ha
to about 200 gai/ha and the compound of formula (I) of salt or
ester thereof is applied at a rate from about 5 g acid equivalent
per hectare (gae/ha) to about 32 gae/ha. In certain embodiments,
the methods utilize the compound of formula (I), or its benzyl
ester and myclobutanil. In one embodiment, the methods utilize the
compound of formula (I) and myclobutanil, wherein the compound of
formula (I) is applied at a rate of from about 3 g acid equivalent
per hectare (gae/ha) to about 200 gae/ha, and myclobutanil is
applied at a rate of about 50 gai/ha to about 450 gai/ha. In one
embodiment, the methods utilize the benzyl ester of the compound of
formula (I) and myclobutanil, wherein the benzyl ester of the
compound of formula (I) is applied at a rate of from about 5 g acid
equivalent per hectare (gae/ha) to about 32 gae/ha, and
myclobutanil is applied at a rate of about 50 gai/ha to about 200
gai/ha.
[0125] In certain embodiments of the compositions and methods
described herein, the compound of formula (I) or salt or ester
thereof is used in combination with phthalide. With respect to the
compositions, in some embodiments, the weight ratio of the compound
of formula (I) or salt or ester thereof to phthalide is within the
range of from about 1:500 to about 15:1. In certain embodiments,
the weight ratio of the compound of formula (I) or salt or ester
thereof to phthalide is within the range of from about 1:267 to
about 5:1. With respect to the methods, in certain embodiments, the
methods comprise contacting the undesirable vegetation or locus
thereof or applying to the soil or water to prevent the emergence
or growth of vegetation a composition described herein. In some
embodiments, the composition is applied at an application rate of
from about 22 grams active ingredient per hectare (gai/ha) to about
1,300 gai/ha based on the total amount of active ingredients in the
composition. In certain embodiments, the composition is applied at
an application rate of from about 33 grams active ingredient per
hectare (gai/ha) to about 950 gai/ha based on the total amount of
active ingredients in the composition. In some embodiments, the
methods comprise contacting the undesirable vegetation or locus
thereof or applying to the soil or water to prevent the emergence
or growth of vegetation with a compound of formula (I) or salt or
ester thereof and phthalide, e.g., sequentially or simultaneously.
In some embodiments, phthalide is applied at a rate from about 20
gai/ha to about 1,000 gai/ha and the compound of formula (I) of
salt or ester thereof is applied at a rate from about 2 gae/ha to
about 300 gae/ha. In some embodiments, phthalide is applied at a
rate from about 25 gai/ha to about 950 gai/ha and the compound of
formula (I) of salt or ester thereof is applied at a rate from
about 3 g acid equivalent per hectare (gae/ha) to about 200 gae/ha.
In certain embodiments, the methods utilize the compound of formula
(I), or its benzyl ester and phthalide. In one embodiment, the
methods utilize the compound of formula (I) and phthalide, wherein
the compound of formula (I) is applied at a rate of from about 3 g
acid equivalent per hectare (gae/ha) to about 200 gae/ha, and
phthalide is applied at a rate of about 25 gai/ha to about 950
gai/ha. In one embodiment, the methods utilize the benzyl ester of
the compound of formula (I) and phthalide, wherein the benzyl ester
of the compound of formula (I) is applied at a rate of from about 3
g acid equivalent per hectare (gae/ha) to about 150 gae/ha, and
phthalide is applied at a rate of about 30 gai/ha to about 800
gai/ha.
[0126] In certain embodiments of the compositions and methods
described herein, the compound of formula (I) or salt or ester
thereof is used in combination with probenazole. With respect to
the compositions, in some embodiments, the weight ratio of the
compound of formula (I) or salt or ester thereof to probenazoleis
within the range of from about 1:2,500 to about 6:1. In certain
embodiments, the weight ratio of the compound of formula (I) or
salt or ester thereof to probenazoleis within the range of from
about 1:500 to about 1:10. With respect to the methods, in certain
embodiments, the methods comprise contacting the undesirable
vegetation or locus thereof or applying to the soil or water to
prevent the emergence or growth of vegetation a composition
described herein. In some embodiments, the composition is applied
at an application rate of from about 52 grams active ingredient per
hectare (gai/ha) to about 5,300 gai/ha based on the total amount of
active ingredients in the composition. In certain embodiments, the
composition is applied at an application rate of from about 103
grams active ingredient per hectare (gai/ha) to about 4,050 gai/ha
based on the total amount of active ingredients in the composition.
In some embodiments, the methods comprise contacting the
undesirable vegetation or locus thereof or applying to the soil or
water to prevent the emergence or growth of vegetation with a
compound of formula (I) or salt or ester thereof and probenazole,
e.g., sequentially or simultaneously. In some embodiments,
probenazole is applied at a rate from about 50 gai/ha to about
5,000 gai/ha and the compound of formula (I) of salt or ester
thereof is applied at a rate from about 2 gae/ha to about 300
gae/ha. In some embodiments, probenazole is applied at a rate from
about 75 gai/ha to about 4,500 gai/ha and the compound of formula
(I) of salt or ester thereof is applied at a rate from about 3 g
acid equivalent per hectare (gae/ha) to about 200 gae/ha. In
certain embodiments, the methods utilize the compound of formula
(I), or its benzyl ester and probenazole. In one embodiment, the
methods utilize the compound of formula (I) and probenazole,
wherein the compound of formula (I) is applied at a rate of from
about 3 g acid equivalent per hectare (gae/ha) to about 200 gae/ha,
and probenazoleis applied at a rate of about 75 gai/ha to about
4,500 gai/ha. In one embodiment, the methods utilize the benzyl
ester of the compound of formula (I) and probenazole wherein the
benzyl ester of the compound of formula (I) is applied at a rate of
from about 8 g acid equivalent per hectare (gae/ha) to about 50
gae/ha, and probenazoleis applied at a rate of about 500 gai/ha to
about 4,000 gai/ha.
[0127] In certain embodiments of the compositions and methods
described herein, the compound of formula (I) or salt or ester
thereof is used in combination with propiconazole. With respect to
the compositions, in some embodiments, the weight ratio of the
compound of formula (I) or salt or ester thereof to propiconazole
is within the range of from about 1:250 to about 30:1. In certain
embodiments, the weight ratio of the compound of formula (I) or
salt or ester thereof to propiconazole is within the range of from
about 1:47 to about 1:3. With respect to the methods, in certain
embodiments, the methods comprise contacting the undesirable
vegetation or locus thereof or applying to the soil or water to
prevent the emergence or growth of vegetation a composition
described herein. In some embodiments, the composition is applied
at an application rate of from about 12 grams active ingredient per
hectare (gai/ha) to about 800 gai/ha based on the total amount of
active ingredients in the composition. In certain embodiments, the
composition is applied at an application rate of from about 67
grams active ingredient per hectare (gai/ha) to about 275 gai/ha
based on the total amount of active ingredients in the composition.
In some embodiments, the methods comprise contacting the
undesirable vegetation or locus thereof or applying to the soil or
water to prevent the emergence or growth of vegetation with a
compound of formula (I) or salt or ester thereof and propiconazole,
e.g., sequentially or simultaneously. In some embodiments,
propiconazole is applied at a rate from about 10 gai/ha to about
500 gai/ha and the compound of formula (I) of salt or ester thereof
is applied at a rate from about 2 gae/ha to about 300 gae/ha. In
some embodiments, propiconazole is applied at a rate from about 20
gai/ha to about 450 gai/ha and the compound of formula (I) of salt
or ester thereof is applied at a rate from about 3 g acid
equivalent per hectare (gae/ha) to about 200 gae/ha. In certain
embodiments, the methods utilize the compound of formula (I), or
its benzyl ester and propiconazole. In one embodiment, the methods
utilize the compound of formula (I) and propiconazole, wherein the
compound of formula (I) is applied at a rate of from about 3 g acid
equivalent per hectare (gae/ha) to about 200 gae/ha, and
propiconazole is applied at a rate of about 20 gai/ha to about 450
gai/ha. In one embodiment, the methods utilize the benzyl ester of
the compound of formula (I) and propiconazole, wherein the benzyl
ester of the compound of formula (I) is applied at a rate of from
about 5.3 g acid equivalent per hectare (gae/ha) to about 21.2
gae/ha, and propiconazole is applied at a rate of about 62.5 gai/ha
to about 250 gai/ha.
[0128] In certain embodiments of the compositions and methods
described herein, the compound of formula (I) or salt or ester
thereof is used in combination with pyroquilon. With respect to the
compositions, in some embodiments, the weight ratio of the compound
of formula (I) or salt or ester thereof to pyroquilon is within the
range of from about 1:1,500 to about 3:1. In certain embodiments,
the weight ratio of the compound of formula (I) or salt or ester
thereof to pyroquilon is within the range of from about 1:933 to
about 1:1. With respect to the methods, in certain embodiments, the
methods comprise contacting the undesirable vegetation or locus
thereof or applying to the soil or water to prevent the emergence
or growth of vegetation a composition described herein. In some
embodiments, the composition is applied at an application rate of
from about 102 grams active ingredient per hectare (gai/ha) to
about 3,300 gai/ha based on the total amount of active ingredients
in the composition. In certain embodiments, the composition is
applied at an application rate of from about 153 grams active
ingredient per hectare (gai/ha) to about 2,950 gai/ha based on the
total amount of active ingredients in the composition. In some
embodiments, the methods comprise contacting the undesirable
vegetation or locus thereof or applying to the soil or water to
prevent the emergence or growth of vegetation with a compound of
formula (I) or salt or ester thereof and pyroquilon, e.g.,
sequentially or simultaneously. In some embodiments, pyroquilon is
applied at a rate from about 100 gai/ha to about 3,000 gai/ha and
the compound of formula (I) of salt or ester thereof is applied at
a rate from about 2 gae/ha to about 300 gae/ha. In some
embodiments, pyroquilon is applied at a rate from about 75 gai/ha
to about 2,900 gai/ha and the compound of formula (I) of salt or
ester thereof is applied at a rate from about 3 g acid equivalent
per hectare (gae/ha) to about 200 gae/ha. In certain embodiments,
the methods utilize the compound of formula (I), or its benzyl
ester and pyroquilon. In one embodiment, the methods utilize the
compound of formula (I) and pyroquilon, wherein the compound of
formula (I) is applied at a rate of from about 3 g acid equivalent
per hectare (gae/ha) to about 200 gae/ha, and pyroquilon is applied
at a rate of about 75 gai/ha to about 2,900 gai/ha. In one
embodiment, the methods utilize the benzyl ester of the compound of
formula (I) and pyroquilon wherein the benzyl ester of the compound
of formula (I) is applied at a rate of from about 3 g acid
equivalent per hectare (gae/ha) to about 150 gae/ha, and pyroquilon
is applied at a rate of about 150 gai/ha to about 2,800 gai/ha.
[0129] In certain embodiments of the compositions and methods
described herein, the compound of formula (I) or salt or ester
thereof is used in combination with tebuconazole. With respect to
the compositions, in some embodiments, the weight ratio of the
compound of formula (I) or salt or ester thereof to tebuconazole is
within the range of from about 1:250 to about 12:1. In certain
embodiments, the weight ratio of the compound of formula (I) or
salt or ester thereof to tebuconazole is within the range of from
about 1:57 to about 1:2. With respect to the methods, in certain
embodiments, the methods comprise contacting the undesirable
vegetation or locus thereof or applying to the soil or water to
prevent the emergence or growth of vegetation a composition
described herein. In some embodiments, the composition is applied
at an application rate of from about 27 grams active ingredient per
hectare (gai/ha) to about 5,300 gai/ha based on the total amount of
active ingredients in the composition. In certain embodiments, the
composition is applied at an application rate of from about 66
grams active ingredient per hectare (gai/ha) to about 280 gai/ha
based on the total amount of active ingredients in the composition.
In some embodiments, the methods comprise contacting the
undesirable vegetation or locus thereof or applying to the soil or
water to prevent the emergence or growth of vegetation with a
compound of formula (I) or salt or ester thereof and tebuconazole,
e.g., sequentially or simultaneously. In some embodiments,
tebuconazole is applied at a rate from about 25 gai/ha to about
5,000 gai/ha and the compound of formula (I) of salt or ester
thereof is applied at a rate from about 2 gae/ha to about 300
gae/ha. In some embodiments, tebuconazole is applied at a rate from
about 60 gai/ha to about 250 gai/ha and the compound of formula (I)
of salt or ester thereof is applied at a rate from about 4 g acid
equivalent per hectare (gae/ha) to about 32 gae/ha. In certain
embodiments, the methods utilize the compound of formula (I), or
its benzyl ester and tebuconazole. In one embodiment, the methods
utilize the compound of formula (I) and tebuconazole, wherein the
compound of formula (I) is applied at a rate of from about 3 g acid
equivalent per hectare (gae/ha) to about 200 gae/ha, and
tebuconazole is applied at a rate of about 50 gai/ha to about 450
gai/ha. In one embodiment, the methods utilize the benzyl ester of
the compound of formula (I) and tebuconazole, wherein the benzyl
ester of the compound of formula (I) is applied at a rate of from
about 4 g acid equivalent per hectare (gae/ha) to about 32 gae/ha,
and tebuconazole is applied at a rate of about 60 gai/ha to about
250 gai/ha.
[0130] In certain embodiments of the compositions and methods
described herein, the compound of formula (I) or salt or ester
thereof is used in combination with thifluzamide. With respect to
the compositions, in some embodiments, the weight ratio of the
compound of formula (I) or salt or ester thereof to thifluzamide is
within the range of from about 1:375 to about 30:1. In certain
embodiments, the weight ratio of the compound of formula (I) or
salt or ester thereof to thifluzamide is within the range of from
about 1:38 to about 1:2.5. With respect to the methods, in certain
embodiments, the methods comprise contacting the undesirable
vegetation or locus thereof or applying to the soil or water to
prevent the emergence or growth of vegetation a composition
described herein. In some embodiments, the composition is applied
at an application rate of from about 12 grams active ingredient per
hectare (gai/ha) to about 1,050 gai/ha based on the total amount of
active ingredients in the composition. In certain embodiments, the
composition is applied at an application rate of from about 83
grams active ingredient per hectare (gai/ha) to about 332 gai/ha
based on the total amount of active ingredients in the composition.
In some embodiments, the methods comprise contacting the
undesirable vegetation or locus thereof or applying to the soil or
water to prevent the emergence or growth of vegetation with a
compound of formula (I) or salt or ester thereof and thifluzamide,
e.g., sequentially or simultaneously. In some embodiments
thifluzamide is applied at a rate from about 10 gai/ha to about 750
gai/ha and the compound of formula (I) of salt or ester thereof is
applied at a rate from about 2 gae/ha to about 300 gae/ha. In some
embodiments, thifluzamide is applied at a rate from about 20 gai/ha
to about 700 gai/ha and the compound of formula (I) of salt or
ester thereof is applied at a rate from about 3 g acid equivalent
per hectare (gae/ha) to about 200 gae/ha. In certain embodiments,
the methods utilize the compound of formula (I), or its benzyl
ester and thifluzamide. In one embodiment, the methods utilize the
compound of formula (I) and thifluzamide, wherein the compound of
formula (I) is applied at a rate of from about 3 g acid equivalent
per hectare (gae/ha) to about 200 gae/ha, and thifluzamide is
applied at a rate of about 20 gai/ha to about 700 gai/ha. In one
embodiment, the methods utilize the benzyl ester of the compound of
formula (I) and thifluzamide, wherein the benzyl ester of the
compound of formula (I) is applied at a rate of from about 8 g acid
equivalent per hectare (gae/ha) to about 32 gae/ha, and
thifluzamide is applied at a rate of about 75 gai/ha to about 300
gai/ha.
[0131] In certain embodiments of the compositions and methods
described herein, the compound of formula (I) or salt or ester
thereof is used in combination with tricyclazole. With respect to
the compositions, in some embodiments, the weight ratio of the
compound of formula (I) or salt or ester thereof to tricyclazole is
within the range of from about 1:375 to about 15:1. In certain
embodiments, the weight ratio of the compound of formula (I) or
salt or ester thereof to tricyclazole is within the range of from
about 1:170 to about 1:1. With respect to the methods, in certain
embodiments, the methods comprise contacting the undesirable
vegetation or locus thereof or applying to the soil or water to
prevent the emergence or growth of vegetation a composition
described herein. In some embodiments, the composition is applied
at an application rate of from about 22 grams active ingredient per
hectare (gai/ha) to about 1,300 gai/ha based on the total amount of
active ingredients in the composition. In certain embodiments, the
composition is applied at an application rate of from about 55
grams active ingredient per hectare (gai/ha) to about 800 gai/ha
based on the total amount of active ingredients in the composition.
In some embodiments, the methods comprise contacting the
undesirable vegetation or locus thereof or applying to the soil or
water to prevent the emergence or growth of vegetation with a
compound of formula (I) or salt or ester thereof and tricyclazole,
e.g., sequentially or simultaneously. In some embodiments,
tricyclazole is applied at a rate from about 20 gai/ha to about
1,000 gai/ha and the compound of formula (I) of salt or ester
thereof is applied at a rate from about 2 gae/ha to about 300
gae/ha. In some embodiments, tricyclazole is applied at a rate from
about 30 gai/ha to about 750 gai/ha and the compound of formula (I)
of salt or ester thereof is applied at a rate from about 4 g acid
equivalent per hectare (gae/ha) to about 42 gae/ha. In certain
embodiments, the methods utilize the compound of formula (I), or
its benzyl ester and tricyclazole. In one embodiment, the methods
utilize the compound of formula (I) and tricyclazole, wherein the
compound of formula (I) is applied at a rate of from about 3 g acid
equivalent per hectare (gae/ha) to about 200 gae/ha, and
tricyclazole is applied at a rate of about 30 gai/ha to about 950
gai/ha. In one embodiment, the methods utilize the benzyl ester of
the compound of formula (I) and tricyclazole, wherein the benzyl
ester of the compound of formula (I) is applied at a rate of from
about 4.4 g acid equivalent per hectare (gae/ha) to about 42.4
gae/ha, and tricyclazole is applied at a rate of about 50 gai/ha to
about 750 gai/ha.
[0132] In certain embodiments of the compositions and methods
described herein, the compound of formula (I) or salt or ester
thereof is used in combination with trifloxystrobin. With respect
to the compositions, in some embodiments, the weight ratio of the
compound of formula (I) or salt or ester thereof to trifloxystrobin
is within the range of from about 1:250 to about 30:1. In certain
embodiments, the weight ratio of the compound of formula (I) or
salt or ester thereof to trifloxystrobin is within the range of
from about 1:38 to about 1:2. With respect to the methods, in
certain embodiments, the methods comprise contacting the
undesirable vegetation or locus thereof or applying to the soil or
water to prevent the emergence or growth of vegetation a
composition described herein. In some embodiments, the composition
is applied at an application rate of from about 12 grams active
ingredient per hectare (gai/ha) to about 800 gai/ha based on the
total amount of active ingredients in the composition. In certain
embodiments, the composition is applied at an application rate of
from about 83 grams active ingredient per hectare (gai/ha) to about
332 gai/ha based on the total amount of active ingredients in the
composition. In some embodiments, the methods comprise contacting
the undesirable vegetation or locus thereof or applying to the soil
or water to prevent the emergence or growth of vegetation with a
compound of formula (I) or salt or ester thereof and
trifloxystrobin, e.g., sequentially or simultaneously. In some
embodiments, trifloxystrobinis applied at a rate from about 10
gai/ha to about 500 gai/ha and the compound of formula (I) of salt
or ester thereof is applied at a rate from about 2 gae/ha to about
300 gae/ha. In some embodiments, trifloxystrobin is applied at a
rate from about 20 gai/ha to about 450 gai/ha and the compound of
formula (I) of salt or ester thereof is applied at a rate from
about 3 g acid equivalent per hectare (gae/ha) to about 200 gae/ha.
In certain embodiments, the methods utilize the compound of formula
(I), or its benzyl ester and trifloxystrobin. In one embodiment,
the methods utilize the compound of formula (I) and
trifloxystrobin, wherein the compound of formula (I) is applied at
a rate of from about 3 g acid equivalent per hectare (gae/ha) to
about 200 gae/ha, and trifloxystrobin is applied at a rate of about
20 gai/ha to about 450 gai/ha. In one embodiment, the methods
utilize the benzyl ester of the compound of formula (I) and
trifloxystrobin, wherein the benzyl ester of the compound of
formula (I) is applied at a rate of from about 8 g acid equivalent
per hectare (gae/ha) to about 32 gae/ha, and trifloxystrobin is
applied at a rate of about 75 gai/ha to about 300 gai/ha.
[0133] In certain embodiments of the compositions and methods
described herein, the compound of formula (I) or salt or ester
thereof is used in combination with validamycin. With respect to
the compositions, in some embodiments, the weight ratio of the
compound of formula (I) or salt or ester thereof to validamycin is
within the range of from about 1:25 to about 3,000:1. In certain
embodiments, the weight ratio of the compound of formula (I) or
salt or ester thereof to validamycin is within the range of from
about 1:13 to about 500:1. With respect to the methods, in certain
embodiments, the methods comprise contacting the undesirable
vegetation or locus thereof or applying to the soil or water to
prevent the emergence or growth of vegetation a composition
described herein. In some embodiments, the composition is applied
at an application rate of from about 2.1 grams active ingredient
per hectare (gai/ha) to about 350 gai/ha based on the total amount
of active ingredients in the composition. In certain embodiments,
the composition is applied at an application rate of from about 3.3
grams active ingredient per hectare (gai/ha) to about 190 gai/ha
based on the total amount of active ingredients in the composition.
In some embodiments, the methods comprise contacting the
undesirable vegetation or locus thereof or applying to the soil or
water to prevent the emergence or growth of vegetation with a
compound of formula (I) or salt or ester thereof and validamycin,
e.g., sequentially or simultaneously. In some embodiments,
validamycin is applied at a rate from about 0.1 gai/ha to about 50
gai/ha and the compound of formula (I) of salt or ester thereof is
applied at a rate from about 2 gae/ha to about 300 gae/ha. In some
embodiments, validamycin is applied at a rate from about 0.2 gai/ha
to about 45 gai/ha and the compound of formula (I) of salt or ester
thereof is applied at a rate from about 3 g acid equivalent per
hectare (gae/ha) to about 200 gae/ha. In certain embodiments, the
methods utilize the compound of formula (I), or its benzyl ester
and validamycin. In one embodiment, the methods utilize the
compound of formula (I) and validamycin, wherein the compound of
formula (I) is applied at a rate of from about 3 g acid equivalent
per hectare (gae/ha) to about 200 gae/ha, and validamycin is
applied at a rate of about 0.2 gai/ha to about 45 gai/ha. In one
embodiment, the methods utilize the benzyl ester of the compound of
formula (I) and validamycin, wherein the benzyl ester of the
compound of formula (I) is applied at a rate of from about 3 g acid
equivalent per hectare (gae/ha) to about 150 gae/ha, and
validamycin is applied at a rate of about 0.3 gai/ha to about 40
gai/ha.
[0134] In certain embodiments of the compositions and methods
described herein, the compound of formula (I) or salt or ester
thereof is used in combination with a compound of formula (II).
With respect to the compositions, in some embodiments, the weight
ratio of the compound of formula (I) or salt or ester thereof to a
compound of formula (II) is within the range of from about 1:375 to
about 150:1. In certain embodiments, the weight ratio of the
compound of formula (I) or salt or ester thereof to a compound of
formula (II) is within the range of from about 1:19 to about 1:1.
With respect to the methods, in certain embodiments, the methods
comprise contacting the undesirable vegetation or locus thereof or
applying to the soil or water to prevent the emergence or growth of
vegetation a composition described herein. In some embodiments, the
composition is applied at an application rate of from about 4 grams
active ingredient per hectare (gai/ha) to about 1,050 gai/ha based
on the total amount of active ingredients in the composition. In
certain embodiments, the composition is applied at an application
rate of from about 45 grams active ingredient per hectare (gai/ha)
to about 182 gai/ha based on the total amount of active ingredients
in the composition. In some embodiments, the methods comprise
contacting the undesirable vegetation or locus thereof or applying
to the soil or water to prevent the emergence or growth of
vegetation with a compound of formula (I) or salt or ester thereof
and a compound of formula (II), e.g., sequentially or
simultaneously. In some embodiments, a compound of formula (II) is
applied at a rate from about 2 gai/ha to about 750 gai/ha and the
compound of formula (I) of salt or ester thereof is applied at a
rate from about 2 gae/ha to about 300 gae/ha. In some embodiments,
a compound of formula (II) is applied at a rate from about 5 gai/ha
to about 700 gai/ha and the compound of formula (I) of salt or
ester thereof is applied at a rate from about 3 g acid equivalent
per hectare (gae/ha) to about 200 gae/ha. In certain embodiments,
the methods utilize the compound of formula (I), or its benzyl
ester and a compound of formula (II). In one embodiment, the
methods utilize the compound of formula (I) and a compound of
formula (II), wherein the compound of formula (I) is applied at a
rate of from about 3 g acid equivalent per hectare (gae/ha) to
about 200 gae/ha, and a compound of formula (II) is applied at a
rate of about 5 gai/ha to about 700 gai/ha. In one embodiment, the
methods utilize the benzyl ester of the compound of formula (I) and
a compound of formula (II), wherein the benzyl ester of the
compound of formula (I) is applied at a rate of from about 8 g acid
equivalent per hectare (gae/ha) to about 32 gae/ha, and a compound
of formula (II) is applied at a rate of about 37.5 gai/ha to about
180 gai/ha.
[0135] In certain embodiments, the methods and compositions
utilizing the compound of formula (I) or salt or ester thereof in
combination with azoxystrobin, carbendazim, difenoconazole,
flutolanil, hexaconazole, iprobenfos, isoprothiolane, isotianil,
kasugamycin, mancozeb, myclobutanil, phthalide, probenazole,
propiconazole, pyroquilon, tebuconazole, thifluzamide,
tricyclazole, trifloxystrobin, validamycin, and a compound of
formula (II) are used to control BRAPP, CYPES, CYPIR, CYPRO, DIGSA,
ECHCG, ECHCO, ECHOR, FIMMI, IPOHE, LEFCH and SCPJU.
[0136] The components of the mixtures described herein can be
applied either separately or as part of a multipart herbicidal
system.
[0137] 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, bialaphos,
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, clomeprop, cloprop, cloproxydim,
clopyralid, cloransulam-methyl, CMA, copper sulfate, CPMF, CPPC,
credazine, cresol, cumyluron, cyanatryn, cyanazine, cycloate,
cyclopyrimorate, 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, flurochloridone, fluroxypyr,
fluroxypyr-meptyl, flurtamone, fluthiacet, fomesafen,
foramsulfuron, fosamine, fumiclorac, furyloxyfen, glufosinate,
glufosinate-ammonium, glufosinate-P-ammonium, glyphosate salts and
esters, halauxifen, halauxifen-methyl, 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, parafluron,
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-methyl,
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,
SYN-523, swep, TCA, tebutam, tebuthiuron, tefuryltrione,
tembotrione, tepraloxydim, terbacil, terbucarb, terbuchlor,
terbumeton, terbuthylazine, terbutryn, tetrafluron, thenylchlor,
thiazafluron, 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 amines, tridiphane, trietazine, trifloxysulfuron,
trifluralin, triflusulfuron, trifop, trifopsime,
trihydroxytriazine, trimeturon, tripropindan, tritac tritosulfuron,
vernolate, xylachlor and salts, esters, optically active isomers
and mixtures thereof.
[0138] The compositions and methods described herein, can further
be used in conjunction with glyphosate,
5-enolpyruvylshikimate-3-phosphate (EPSP) synthase inhibitors,
glufosinate, glutamine synthetase inhibitors, dicamba, phenoxy
auxins, pyridyloxy auxins, synthetic auxins, auxin transport
inhibitors, aryloxyphenoxypropionates, cyclohexanediones,
phenylpyrazolines, acetyl CoA carboxylase (ACCase) inhibitors,
imidazolinones, sulfonylureas, pyrimidinylthiobenzoates,
triazolopyrimidines, sulfonylaminocarbonyltriazolinones,
acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS)
inhibitors, 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitors,
phytoene desaturase inhibitors, carotenoid biosynthesis inhibitors,
protoporphyrinogen oxidase (PPO) inhibitors, cellulose biosynthesis
inhibitors, mitosis inhibitors, microtubule inhibitors, very long
chain fatty acid inhibitors, fatty acid and lipid biosynthesis
inhibitors, photosystem I inhibitors, photosystem II inhibitors,
triazines, and bromoxynil on glyphosate-tolerant, EPSP synthase
inhibitor-tolerant, glufosinate-tolerant, glutamine synthetase
inhibitor-tolerant, dicamba-tolerant, phenoxy auxin-tolerant,
pyridyloxy auxin-tolerant, auxin-tolerant, auxin transport
inhibitor-tolerant, aryloxyphenoxypropionate-tolerant,
cyclohexanedione-tolerant, phenylpyrazoline-tolerant,
ACCase-tolerant, imidazolinone-tolerant, sulfonylurea-tolerant,
pyrimidinylthiobenzoate-tolerant, triazolopyrimidine-tolerant,
sulfonylaminocarbonyltriazolinone-tolerant, ALS- or AHAS-tolerant,
HPPD-tolerant, phytoene desaturase inhibitor-tolerant, carotenoid
biosynthesis inhibitor tolerant, PPO-tolerant, cellulose
biosynthesis inhibitor-tolerant, mitosis inhibitor-tolerant,
microtubule inhibitor-tolerant, very long chain fatty acid
inhibitor-tolerant, fatty acid and lipid biosynthesis
inhibitor-tolerant, photosystem I inhibitor-tolerant, photosystem
II inhibitor-tolerant, triazine-tolerant, bromoxynil-tolerant, and
crops possessing multiple or stacked traits conferring tolerance to
multiple chemistries and/or multiple modes of action via single
and/or multiple resistance mechanisms. In some embodiments, the
compound of formula (I) or salt or ester thereof and complementary
herbicide or salt or ester thereof are 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. In some embodiments, the
compositions described herein and other complementary herbicides
are applied at the same time, either as a combination formulation
or as a tank mix.
[0139] In some embodiments, the compositions described herein are
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.
In some embodiments, the safeners are employed in rice, cereal,
corn, or maize settings. In some embodiments, the safener is
cloquintocet or an ester or salt thereof. In certain embodiments,
cloquintocet is utilized to antagonize harmful effects of the
compositions on rice and cereals. In some embodiments, the safener
is cloquintocet (mexyl).
[0140] In some embodiments, the compositions described herein are
employed in combination with one or more plant growth regulators,
such as 2,3,5-tri-iodobenzoic acid, IAA, IBA, naphthaleneacetamide,
.alpha.-naphthaleneacetic acids, benzyladenine, 4-hydroxyphenethyl
alcohol, kinetin, zeatin, endothal, ethephon, pentachlorophenol,
thidiazuron, tribufos, aviglycine, maleic hydrazide, gibberellins,
gibberellic acid, abscisic acid, ancymidol, fosamine, glyphosine,
isopyrimol, jasmonic acid, maleic hydrazide, mepiquat,
2,3,5-tri-iodobenzoic acid, morphactins, dichlorflurenol,
flurprimidol, mefluidide, paclobutrazol, tetcyclacis, uniconazole,
brassinolide, brassinolide-ethyl, cycloheximide, ethylene,
methasulfocarb, prohexadione, triapenthenol and trinexapac.
[0141] In some embodiments, the plant growth regulators are
employed in one or more crops or settings, such as rice, cereal
crops, corn, maize, broadleaf crops, oilseed rape/canola, turf,
pineapple, sugarcane, sunflower, pastures, grasslands, rangelands,
fallowland, tree and vine orchards, plantation crops, vegetables,
and non-crop (ornamentals) settings. In some embodiments, the plant
growth regulator is mixed with the compound of formula (I), or
mixed with the compound of formula (I) and fungicides to cause a
preferentially advantageous effect on plants.
[0142] In some embodiments, compositions provided herein further
comprise 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 the area adjacent to
the weeds 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.
[0143] 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.
[0144] 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. In certain
embodiments, water is the carrier for the dilution of
concentrates.
[0145] 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.
[0146] In some embodiments, the compositions described herein
further comprise one or more surface-active agents. In some
embodiments, 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;
alkyl-naphthalene-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.
[0147] In some embodiments, 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.
[0148] 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, fungicides, and the like and can be
formulated with liquid fertilizers or solid, particulate fertilizer
carriers such as ammonium nitrate, urea and the like.
[0149] In some embodiments, the concentration of the active
ingredients in the compositions described herein is from about
0.0005 to 98 percent by weight. In some embodiments, the
concentration is from about 0.0006 to 90 percent by weight. In
compositions designed to be employed as concentrates, the active
ingredients, in certain embodiments, are present in a concentration
from about 0.1 to 98 weight percent, and in certain embodiment's
about 0.5 to 90 weight percent. Such compositions are, in certain
embodiments, diluted with an inert carrier, such as water, before
application. The diluted compositions usually applied to weeds or
the locus of weeds contain, in certain embodiments, about 0.0006 to
25.0 weight percent active ingredient and in certain embodiments
contain about 0.001 to 20.0 weight percent.
[0150] The present compositions can be applied to undesirable
vegetation (weeds) or the area adjacent to the weeds by the 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.
[0151] The described embodiments 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 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
[0152] Results in Examples I and II are greenhouse trial
results.
Example I
Evaluation of Postemergence Foliar-Applied Herbicidal Mixtures for
Weed Control in Direct-Seeded Rice
[0153] Seeds or nutlets of the desired test plant species were
planted in a soil matrix prepared by mixing aloam or sandy loam
soil (e.g., 28.6 percent silt, 18.8 percent clay, and 52.6 percent
sand, with a pH of about5.8 and an organic matter content of about
1.8 percent) and calcareous grit in an 80 to 20 ratio. The soil
matrix was contained in plastic pots with a volume of 1 quart and a
surface area of 83.6 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 8-22 days in a greenhouse with an approximate 14 h photoperiod
which was maintained at about 29.degree. C. during the day and
26.degree. C. during the night. Nutrients (Peters Excel.RTM.
15-5-15 5-Ca 2-Mg and iron chelate) were applied in the irrigation
solution as needed and water was added on a regular basis.
Supplemental lighting was provided with overhead metal halide
1000-Watt lamps as necessary. The plants were employed for testing
when they reached the first through fourth true leaf stage.
[0154] Treatments consisted of the acid or esters of
4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxy-phenyl)pyridine--
2-carboxylic acid (Compound A), each formulated as an SC
(suspension concentrate), and various fungicidal components alone
and in combination. Forms of compound A were applied on an acid
equivalent basis.
Forms of compound A (compound of formula I) tested include:
##STR00032##
Other fungicidal components were applied on an active ingredient
basis and consisted of azoxystrobin formulated as Amistar.RTM.,
carbendazim (technical grade material), difenoconazole formulated
as Inspire.RTM., flutolanil (technical grade material),
hexaconazole (technical grade material), isotianil (technical grade
material), kasugamycin (technical grade material), mancozeb
formulated as Dithane.RTM. M45, myclobutanil formulated as
Eagle.RTM., propiconazole formulated as Tilt.RTM., tebuconazole
formulated as Corail.RTM., thifluzamide (technical grade material),
tricyclazole formulated as Beam.RTM., trifloxystrobin (technical
grade material), and a compound of formula (II) formulated as an
SC.
[0155] Treatment requirements were calculated based upon the rates
being tested, the concentration of active ingredient or acid
equivalent in the formulation, and a 12 mL application volume at a
rate of 187 L/ha.
[0156] For treatments comprised of technical compounds, weighed
amounts can be placed individually in 25 mL glass vials and
dissolved in a volume of 97:3 v/v acetone/DMSO to obtain 12.times.
stock solutions. If a test compound does not dissolve readily, the
mixture can be warmed and/or sonicated. Application solutions can
be prepared by adding an appropriate amount of each stock solution
(e.g., 1 mL) and diluted to the appropriate final concentrations
with the addition of 10 mL of an aqueous mixture of 1.5% (v/v) crop
oil concentrate so that the final spray solutions contain 1.25%
(v/v) crop oil concentrate. When technical materials are used, the
concentrated stock solutions can be added to the spray solutions so
that the final acetone and DMSO concentrations of the application
solutions are 16.2% and 0.5%, respectively.
[0157] For treatments comprised of formulated and technical
compounds, weighed amounts of the technical materials can be placed
individually in 25 mL glass vials and dissolved in a volume of 97:3
v/v acetone/DMSO to obtain 12.times. stock solutions, and measured
amounts of the formulated compounds can be placed individually in
25 mL glass vials and diluted in a volume of 1.5% (v/v) crop oil
concentrate or water to obtain 12.times. stock solutions. If a test
compound does not dissolve readily, the mixture can be warmed
and/or sonicated. Application solutions can be prepared by adding
an appropriate amount of each stock solution (e.g., 1 mL) and
diluted to the appropriate final concentrations with the addition
of an appropriate amount of an aqueous mixture of 1.5% (v/v) crop
oil concentrate so that the final spray solutions contain 1.25%
(v/v) crop oil concentrate. As required, additional water and/or
97:3 v/v acetone/DMSO can be added to individual application
solutions so that the final acetone and DMSO concentrations of the
application solutions being compared are 8.1% and 0.25%,
respectively
[0158] All stock solutions and applications solutions were visually
inspected for compound compatibility prior to application. Spray
solutions were applied to the plant material with an overhead
Mandel track sprayer equipped with a 8002E nozzles calibrated to
deliver 187 L/ha over an application area of 0.503 m.sup.2 at a
spray height of 18 to 20 inches (46 to 50 cm) above average plant
canopy height. Control plants were sprayed in the same manner with
the solvent blank.
[0159] 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 approximately 3
weeks, the condition of the test plants as compared with that of
the untreated plants was determined visually and scored on a scale
of 0 to 100 percent where 0 corresponds to no injury or growth
inhibition and 100 corresponds to complete kill.
[0160] 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.).
[0161] 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)
[0162] A=observed efficacy of active ingredient A at the same
concentration as used in the mixture.
[0163] B=observed efficacy of active ingredient B at the same
concentration as used in the mixture.
[0164] The compounds tested, application rates employed, plant
species tested, and results are given in Tables 1-22.
TABLE-US-00001 TABLE 1 Synergistic Activity of Foliar-Applied
Compound A Acid and Azoxystrobin Compositions on Weed Control in a
Rice Cropping System. Visual Weed Compound A Control (%) - 21 DAA
Acid Azoxystrobin DIGSA IPOHE gae/ha gai/ha Obs Exp Obs Exp 5.3 0
10 -- 10 -- 10.6 0 20 -- 15 -- 21.2 0 20 -- 20 -- 0 250 0 -- 0 --
5.3 250 30 10 20 10 10.6 250 25 20 30 15 21.2 250 NT 20 25 20
TABLE-US-00002 TABLE 2 Synergistic Activity of Foliar-Applied
Compound A Benzyl Ester and Azoxystrobin Compositions on Weed
Control in a Rice Cropping System. Visual Weed Compound A Control
(%) - 21 DAA Benzyl Ester Azoxystrobin DIGSA IPOHE gae/ha gai/ha
Obs Exp Obs Exp 4.38 0 20 -- 10 -- 8.75 0 15 -- 10 -- 17.5 0 20 --
20 -- 0 250 0 -- 0 -- 4.38 250 20 20 25 10 8.75 250 60 15 15 10
17.5 250 50 20 30 20 Visual Weed Control (%) - 22 Compound A DAA
Benzyl Ester Azoxystrobin CYPIR gae/ha gai/ha Obs Exp 16 0 73 -- 32
0 60 -- 0 62.5 0 -- 0 125 0 -- 0 250 0 -- 16 62.5 100 73 32 62.5
100 60 16 125 85 73 32 125 100 60 16 250 98 73 32 250 100 60 Visual
Weed Control (%) - 22 Compound A DAA Benzyl Ester Azoxystrobin
BRAPP gae/ha gai/ha Obs Exp 8 0 65 -- 16 0 70 -- 32 0 90 -- 0 125 0
-- 0 250 0 -- 8 125 70 65 16 125 73 70 32 125 90 90 8 250 78 65 16
250 83 70 32 250 90 90 Visual Weed Control (%) - 21 Compound A DAA
Benzyl Ester Azoxystrobin ECHOR gae/ha gai/ha Obs Exp 16 0 43 -- 32
0 70 -- 0 62.5 8 -- 0 125 8 -- 0 250 5 -- 16 62.5 40 47 32 62.5 85
72 16 125 58 47 32 125 90 72 16 250 58 45 32 250 90 72
TABLE-US-00003 TABLE 3 Synergistic Activity of Foliar-Applied
Compound A Benzyl Ester and Carbendazim Compositions on Weed
Control in a Rice Cropping System. Visual Weed Control (%) - 19
Compound A DAA Benzyl Ester Carbendazim ECHCO gae/ha gai/ha Obs Exp
8 0 65 -- 16 0 90 -- 32 0 95 -- 0 125 0 -- 0 250 0 -- 8 125 85 65
16 125 95 90 32 125 99 95 8 250 95 65 16 250 95 90 32 250 95 95
TABLE-US-00004 TABLE 4 Synergistic Activity of Foliar-Applied
Compound A Acid and Difenoconazole Compositions on Weed Control in
a Rice Cropping System. Com- pound A Visual Weed Control (%) - 21
DAA Acid Difenoconazole DIGSA ECHCG LEFCH gae/ha gai/ha Obs Exp Obs
Exp Obs Exp 5.3 0 10 -- 80 -- 10 -- 10.6 0 20 -- 90 -- 20 -- 21.2 0
20 -- 95 -- 45 -- 0 200 0 -- 0 -- 0 -- 5.3 200 10 10 95 80 50 10
10.6 200 25 20 95 90 30 20 21.2 200 50 20 99 95 40 45
TABLE-US-00005 TABLE 5 Synergistic Activity of Foliar-Applied
Compound A Benzyl Ester and Difenoconazole Compositions on Weed
Control in a Rice Cropping System. Visual Weed Compound A Control
(%) - 21 DAA Benzyl Ester Difenoconazole LEFCH IPOHE gae/ha gai/ha
Obs Exp Obs Exp 4.38 0 10 -- 10 -- 8.75 0 20 -- 10 -- 17.5 0 55 --
20 -- 0 200 0 -- 0 -- 4.38 200 30 10 10 10 8.75 200 45 20 30 10
17.5 200 50 55 40 20 Visual Weed Control (%) - 22 Compound A DAA
Benzyl Ester Difenoconazole DIGSA gae/ha gai/ha Obs Exp 8 0 15 --
16 0 23 -- 32 0 28 -- 0 50 0 -- 0 100 0 -- 0 200 0 -- 8 50 25 15 16
50 28 23 32 50 45 28 8 100 40 15 16 100 53 23 32 100 55 28 8 200 55
15 16 200 53 23 32 200 68 28 Visual Weed Control (%) - 21 Compound
A DAA Benzyl Ester Difenoconazole LEFCH gae/ha gai/ha Obs Exp 16 0
25 -- 32 0 43 -- 0 50 0 -- 0 100 0 -- 0 200 0 16 50 30 25 32 50 53
43 16 100 33 25 32 100 60 43 16 200 48 25 32 200 70 43 Visual Weed
Control (%) - 21 Compound A DAA Benzyl Ester Difenoconazole ECHCG
gae/ha gai/ha Obs Exp 8 0 70 -- 16 0 60 -- 32 0 90 -- 0 50 0 -- 0
100 0 -- 0 200 0 -- 8 50 83 70 16 50 90 60 32 50 93 90 8 100 80 70
16 100 88 60 32 100 95 90 8 200 88 70 16 200 95 60 32 200 95 90
Visual Weed Control (%) - 21 Compound A DAA Benzyl Ester
Difenoconazole ECHOR gae/ha gai/ha Obs Exp 8 0 45 -- 16 0 43 -- 32
0 70 -- 0 50 0 -- 0 100 0 -- 0 200 0 -- 8 50 58 45 16 50 63 43 32
50 96 70 8 100 65 45 16 100 88 43 32 100 95 70 8 200 65 45 16 200
88 43 32 200 93 70
TABLE-US-00006 TABLE 6 Synergistic Activity of Foliar-Applied
Compound A Benzyl Ester and Flutolanil Compositions on Weed Control
in a Rice Cropping System. Visual Weed Compound A Control (%) - 19
DAA Benzyl Ester Flutolanil ECHCO LEFCH gae/ha gai/ha Obs Exp Obs
Exp 8 0 65 -- 45 -- 16 0 90 -- 45 -- 32 0 95 -- 50 -- 0 280 0 -- 0
-- 0 560 0 -- 0 -- 8 280 85 65 60 45 16 280 95 90 60 45 32 280 100
95 70 50 8 560 90 65 50 45 16 560 95 90 50 45 32 560 99 95 55
50
TABLE-US-00007 TABLE 7 Synergistic Activity of Foliar-Applied
Compound A Benzyl Ester and Hexaconazole Compositions on Weed
Control in a Rice Cropping System. Com- pound A Visual Weed Control
(%) - 21 DAA Benzyl Ester Hexaconazole ECHCG ECHCO LEFCH gae/ha
gai/ha Obs Exp Obs Exp Obs Exp 8 0 45 -- 50 -- 25 -- 16 0 85 -- 65
-- 40 -- 32 0 90 -- 85 -- 55 -- 0 25 0 -- 0 -- 0 -- 0 50 0 -- 0 --
0 -- 0 100 0 -- 0 -- 0 -- 8 25 80 45 75 50 40 25 16 25 90 85 90 65
50 40 32 25 95 90 90 85 65 55 8 50 80 45 80 50 20 25 16 50 90 85 85
65 75 40 32 50 90 90 95 85 60 55 8 100 85 45 90 50 45 25 16 100 90
85 90 65 55 40 32 100 95 90 95 85 60 55 Visual Weed Control
Compound A (%) - 21 DAA Benzyl Ester Hexaconazole BRAPP IPOHE
gae/ha gai/ha Obs Exp Obs Exp 8 0 55 -- 10 -- 16 0 60 -- 25 -- 0 25
0 -- 0 -- 0 50 0 -- 0 -- 0 100 0 -- 0 -- 8 25 65 55 30 10 16 25 85
60 35 25 8 50 50 55 20 10 16 50 80 60 60 25 8 100 65 55 20 10 16
100 65 60 40 25 Visual Weed Control (%) - Compound A 21 DAA Benzyl
Ester Hexaconazole CYPIR gae/ha gai/ha Obs Exp 8 0 35 -- 0 25 0 --
0 50 0 -- 0 100 0 -- 8 25 80 35 8 50 60 35 8 100 50 35
TABLE-US-00008 TABLE 8 Synergistic Activity of Foliar-Applied
Compound A Benzyl Ester and Isotianil Compositions on Weed Control
in a Rice Cropping System. Visual Weed Control (%) - Compound A 20
DAA Benzyl Ester Isotianil BRAPP gae/ha gai/ha Obs Exp 8 0 60 -- 16
0 85 -- 32 0 90 -- 0 200 0 -- 8 200 75 60 16 200 90 85 32 200 90 90
8 0 20 -- 16 0 30 -- 32 0 40 -- 0 100 0 -- 0 200 0 -- 8 100 30 20
16 100 55 30 32 100 60 40 8 200 35 20 16 200 60 30 32 200 50 40
Compound A Benzyl Visual Weed Control (%) - 21 DAA Ester Isotianil
BRAPP DIGSA ECHCG ECHCO LEFCH gae/ha gai/ha Obs Exp Obs Exp Obs Exp
Obs Exp Obs Exp 8 0 55 -- 15 -- 45 -- 50 -- 25 -- 16 0 60 -- 25 --
85 -- 65 -- 40 -- 0 380 0 -- 0 -- 0 -- 0 -- 0 -- 8 380 80 55 50 15
80 45 80 50 55 25 16 380 90 60 50 25 85 85 90 65 55 40
TABLE-US-00009 TABLE 9 Synergistic Activity of Foliar-Applied
Compound A Benzyl Ester and Kasugamycin Compositions on Weed
Control in a Rice Cropping System. Compound A Benzyl Visual Weed
Control (%) - 21 DAA Ester Kasugamycin DIGSA ECHOR LEFCH IPOHE
gae/ha gai/ha Obs Exp Obs Exp Obs Exp Obs Exp 8 0 20 -- 20 -- 40 --
0 -- 16 0 40 -- 60 -- 40 -- 30 -- 32 0 50 -- 85 -- 65 -- 55 -- 0
17.5 0 -- 0 -- 0 -- 0 -- 0 35 0 -- 0 -- 0 -- 0 -- 0 70 0 -- 0 -- 0
-- 0 -- 8 17.5 30 20 40 20 50 40 10 0 16 17.5 40 40 65 60 60 40 50
30 32 17.5 55 50 90 85 75 65 65 55 8 35 25 20 60 20 50 40 25 0 16
35 40 40 80 60 70 40 50 30 32 35 65 50 95 85 65 65 65 55 8 70 40 20
35 20 45 40 50 0 16 70 45 40 65 60 55 40 45 30 32 70 60 50 95 85 70
65 70 55 Visual Weed Control (%) - Compound A 21 DAA Benzyl Ester
Kasugamycin CYPIR gae/ha gai/ha Obs Exp 8 0 50 -- 16 0 70 -- 0 17.5
0 -- 0 35 0 -- 0 70 0 -- 8 17.5 85 50 16 17.5 100 70 8 35 50 50 16
35 100 70 8 70 50 50 16 70 100 70 8 0 70 -- 0 17.5 0 -- 0 35 0 -- 0
70 0 -- 8 17.5 95 70 8 35 70 70 8 70 85 70
TABLE-US-00010 TABLE 10 Synergistic Activity of Foliar-Applied
Compound A Benzyl Ester and Mancozeb Compositions on Weed Control
in a Rice Cropping System. Visual Weed Control (%) - 21 Compound A
DAA Benzyl Ester Mancozeb LEFCH gae/ha gai/ha Obs Exp 16 0 15 -- 32
0 25 -- 0 840 0 -- 16 840 25 15 32 840 45 25 Visual Weed Control
(%) - 21 Compound A DAA Benzyl Ester Mancozeb IPOHE gae/ha gai/ha
Obs Exp 8 0 10 -- 16 0 50 -- 32 0 60 -- 0 1680 0 -- 8 1680 20 10 16
1680 70 50 32 1680 70 60
TABLE-US-00011 TABLE 11 Synergistic Activity of Foliar-Applied
Compound A Acid and Myclobutanil Compositions on Weed Control in a
Rice Cropping System. Compound A Visual Weed Control (%) - 21 DAA
Acid Myclobutanil LEFCH IPOHE gae/ha gai/ha Obs Exp Obs Exp 5.3 0
10 -- 10 -- 10.6 0 20 -- 15 -- 21.2 0 45 -- 20 -- 0 250 0 -- 10 --
5.3 250 10 10 10 19 10.6 250 30 20 10 24 21.2 250 70 45 65 28
TABLE-US-00012 TABLE 12 Synergistic Activity of Foliar-Applied
Compound A Benzyl Ester and Myclobutanil Compositions on Weed
Control in a Rice Cropping System. Compound A Visual Weed Control
(%) - 21 DAA Benzyl Ester Myclobutanil LEFCH IPOHE gae/ha gai/ha
Obs Exp Obs Exp 4.38 0 10 -- 10 -- 8.75 0 20 -- 10 -- 17.5 0 55 --
20 -- 0 250 0 -- 10 -- 4.38 250 30 10 10 19 8.75 250 60 20 10 19
17.5 250 75 55 45 28 Visual Weed Compound A Control (%) - 21 DAA
Benzyl Ester Myclobutanil LEFCH gae/ha gai/ha Obs Exp 8 0 23 -- 16
0 25 -- 32 0 43 -- 0 200 0 -- 8 200 30 23 16 200 50 25 32 200 65 43
Visual Weed Compound A Control (%) - 21 DAA Benzyl Ester
Myclobutanil ECHCG gae/ha gai/ha Obs Exp 8 0 70 -- 16 0 60 -- 32 0
90 -- 0 50 0 -- 0 100 0 -- 0 200 0 -- 8 50 88 70 16 50 90 60 32 50
97 90 8 100 90 70 16 100 93 60 32 100 95 90 8 200 90 70 16 200 93
60 32 200 95 90 Visual Weed Compound A Control (%) - 21 DAA Benzyl
Ester Myclobutanil ECHOR gae/ha gai/ha Obs Exp 8 0 45 -- 16 0 43 --
32 0 70 -- 0 50 0 -- 0 100 0 -- 0 200 0 -- 8 50 80 45 16 50 85 43
32 50 95 70 8 100 90 45 16 100 93 43 32 100 97 70 8 200 85 45 16
200 90 43 32 200 97 70
TABLE-US-00013 TABLE 13 Synergistic Activity of Foliar-Applied
Compound A Benzyl Ester and Probenazole Compositions on Weed
Control in a Rice Cropping System. Visual Weed Control (%) - 19
Compound A DAA Benzyl Ester Probenazole ECHCO gae/ha gai/ha Obs Exp
8 0 65 -- 0 500 0 -- 8 500 85 65
TABLE-US-00014 TABLE 14 Synergistic Activity of Foliar-Applied
Compound A Acid and Propiconazole Compositions on Weed Control in a
Rice Cropping System. Visual Weed Control (%) - 21 Compound A DAA
Acid Propiconazole DIGSA gae/ha gai/ha Obs Exp 5.3 0 10 -- 10.6 0
20 -- 21.2 0 20 -- 0 190 0 -- 5.3 190 0 10 10.6 190 40 20 21.2 190
40 20
TABLE-US-00015 TABLE 15 Synergistic Activity of Foliar-Applied
Compound A Benzyl Ester and Propiconazole Compositions on Weed
Control in a Rice Cropping System. Compound A Visual Weed Control
(%) - 20 DAA Benzyl Ester Propiconazole CYPES SCPJU gae/ha gai/ha
Obs Exp Obs Exp 8 0 0 -- 70 -- 16 0 75 -- 85 -- 0 62.5 0 -- 0 -- 0
125 0 -- 0 -- 0 250 0 -- 0 -- 8 62.5 63 0 70 70 16 62.5 85 75 95 85
8 125 80 0 95 70 16 125 80 75 100 85 8 250 73 0 90 70 16 250 93 75
99 85
TABLE-US-00016 TABLE 16 Synergistic Activity of Foliar-Applied
Compound A Acid and Tebuconazole Compositions on Weed Control in a
Rice Cropping System. Compound Visual Weed Control (%) - 21 DAA A
Acid Tebuconazole DIGSA ECHCG LEFCH IPOHE gae/ha gai/ha Obs Exp Obs
Exp Obs Exp Obs Exp 5.3 0 10 -- 80 -- 10 -- 10 -- 10.6 0 20 -- 90
-- 20 -- 15 -- 21.2 0 20 -- 95 -- 45 -- 20 -- 0 250 0 -- 0 -- 0 --
0 -- 5.3 250 25 10 95 80 10 10 15 10 10.6 250 40 20 95 90 50 20 15
15 21.2 250 60 20 99 95 85 45 60 20
TABLE-US-00017 TABLE 17 Synergistic Activity of Foliar-Applied
Compound A Benzyl Ester and Tebuconazole Compositions on Weed
Control in a Rice Cropping System. Visual Weed Control (%) - 21
Compound A DAA Benzyl Ester Tebuconazole LEFCH gae/ha gai/ha Obs
Exp 4.38 0 10 -- 8.75 0 20 -- 17.5 0 55 -- 0 250 0 -- 4.38 250 20
10 8.75 250 60 20 17.5 250 65 55 8 0 23 -- 16 0 25 -- 32 0 43 -- 0
62.5 5 -- 0 125 10 -- 0 250 8 -- 8 62.5 55 26 16 62.5 53 29 32 62.5
75 45 8 125 50 30 16 125 58 33 32 125 70 48 8 250 43 28 16 250 60
31 32 250 80 47 Visual Weed Control (%) - 22 Compound A DAA Benzyl
Ester Tebuconazole BRAPP gae/ha gai/ha Obs Exp 8 0 65 -- 0 62.5 0
-- 0 125 0 -- 0 250 0 -- 8 62.5 78 65 8 125 63 65 8 250 85 65
Visual Weed Control (%) - 22 Compound A DAA Benzyl Ester
Tebuconazole CYPIR gae/ha gai/ha Obs Exp 8 0 75 -- 16 0 73 -- 32 0
60 -- 0 125 0 -- 0 250 0 -- 8 125 68 75 16 125 90 73 32 125 100 60
8 250 100 75 16 250 100 73 32 250 100 60 Visual Weed Control (%) -
22 Compound A DAA Benzyl Ester Tebuconazole IPOHE gae/ha gai/ha Obs
Exp 8 0 15 -- 16 0 33 -- 0 62.5 0 -- 8 62.5 30 15 16 62.5 53 33
Visual Weed Control (%) - Compound A 21 DAA Benzyl Ester
Tebuconazole ECHCG gae/ha gai/ha Obs Exp 8 0 70 -- 16 0 60 -- 32 0
90 -- 0 62.5 0 -- 0 125 5 -- 0 250 8 -- 8 62.5 90 70 16 62.5 95 60
32 62.5 95 90 8 125 88 72 16 125 90 62 32 125 95 91 8 250 93 72 16
250 90 63 32 250 97 91 Visual Weed Control (%) - Compound A 21 DAA
Benzyl Ester Tebuconazole ECHOR gae/ha gai/ha Obs Exp 8 0 45 -- 16
0 43 -- 32 0 70 -- 0 62.5 0 -- 0 125 5 -- 0 250 8 -- 8 62.5 90 45
16 62.5 90 43 32 62.5 97 70 8 125 93 48 16 125 95 45 32 125 95 72 8
250 88 49 16 250 95 47 32 250 95 72 Visual Weed Control (%) - 22
Compound A DAA Benzyl Ester Tebuconazole DIGSA gae/ha gai/ha Obs
Exp 8 0 15 -- 16 0 23 -- 32 0 28 -- 0 62.5 0 -- 0 125 0 -- 0 250 0
-- 8 62.5 38 15 16 62.5 53 23 32 62.5 60 28 8 125 43 15 16 125 40
23 32 125 58 28 8 250 45 15 16 250 45 23 32 250 63 28
TABLE-US-00018 TABLE 18 Synergistic Activity of Foliar-Applied
Compound A Benzyl Ester and Thifluzamide Compositions on Weed
Control in a Rice Cropping System. Compound A Visual Weed Control
(%) - 20 DAA Benzyl Ester Thifluzamide BRAPP DIGSA gae/ha gai/ha
Obs Exp Obs Exp 8 0 60 -- 20 -- 16 0 85 -- 30 -- 32 0 90 -- 40 -- 0
75 0 -- 0 -- 0 150 0 -- 0 -- 0 300 0 -- 0 -- 8 75 80 60 30 20 16 75
75 85 45 30 32 75 95 90 45 40 8 150 80 60 50 20 16 150 95 85 40 30
32 150 95 90 50 40 8 300 80 60 35 20 16 300 85 85 30 30 32 300 95
90 35 40
TABLE-US-00019 TABLE 19 Synergistic Activity of Foliar-Applied
Compound A Acid and Tricyclazole Compositions on Weed Control in a
Rice Cropping System. Visual Weed Control (%) - 21 Compound A DAA
Acid Tricyclazole IPOHE gae/ha gai/ha Obs Exp 5.3 0 10 -- 10.6 0 15
-- 21.2 0 20 -- 0 200 0 -- 5.3 200 30 10 10.6 200 25 15 21.2 200 60
20
TABLE-US-00020 TABLE 20 Synergistic Activity of Foliar-Applied
Compound A Benzyl Ester and Tricyclazole Compositions on Weed
Control in a Rice Cropping System. Visual Weed Control (%) - 21
Compound A DAA Benzyl Ester Tricyclazole IPOHE gae/ha gai/ha Obs
Exp 4.38 0 10 -- 8.75 0 10 -- 17.5 0 20 -- 0 200 0 -- 4.38 200 15
10 8.75 200 15 10 17.5 200 40 20 Visual Weed Control (%) - 21
Compound A DAA Benzyl Ester Tricyclazole ECHCG gae/ha gai/ha Obs
Exp 8 0 70 -- 16 0 60 -- 32 0 90 -- 0 50 0 -- 0 100 0 -- 0 200 0 --
8 50 75 70 16 50 80 60 32 50 95 90 8 100 65 70 16 100 78 60 32 100
93 90 8 200 85 70 16 200 90 60 32 200 95 90 Visual Weed Control (%)
- 21 Compound A DAA Benzyl Ester Tricyclazole ECHOR gae/ha gai/ha
Obs Exp 8 0 45 -- 16 0 43 -- 32 0 70 -- 0 50 0 -- 0 100 0 -- 0 200
0 -- 8 50 58 45 16 50 68 43 32 50 90 70 8 100 48 45 16 100 55 43 32
100 93 70 8 200 58 45 16 200 78 43 32 200 90 70 Visual Weed Control
(%) - 22 Compound A DAA Benzyl Ester Tricyclazole IPOHE gae/ha
gai/ha Obs Exp 8 0 15 -- 16 0 33 -- 0 50 0 -- 0 100 0 -- 0 200 10
-- 8 50 28 15 16 50 55 33 8 100 15 15 16 100 55 33 8 200 38 24 16
200 45 39
TABLE-US-00021 TABLE 21 Synergistic Activity of Foliar-Applied
Compound A Benzyl Ester and Trifloxystrobin Compositions on Weed
Control in a Rice Cropping System. Visual Weed Control (%) - 21
Compound A DAA Benzyl Ester Trifloxystrobin CYPIR gae/ha gai/ha Obs
Exp 8 0 50 -- 16 0 70 -- 32 0 100 -- 0 140 0 -- 8 140 70 50 16 140
95 70 32 140 100 100 Visual Weed Control (%) - 20 Compound A DAA
Benzyl Ester Trifloxystrobin DIGSA gae/ha gai/ha Obs Exp 8 0 15 --
0 75 0 -- 0 150 0 -- 0 300 0 -- 8 75 30 15 8 150 10 15 8 300 30 15
Visual Weed Control (%) - 20 Compound A DAA Benzyl Ester
Trifloxystrobin CYPES gae/ha gai/ha Obs Exp 16 0 40 -- 0 75 0 -- 0
150 0 -- 16 75 70 40 16 150 60 40
TABLE-US-00022 TABLE 22 Synergistic Activity of Foliar-Applied
Compound A Benzyl Ester and a compound of formula (II) Compositions
on Weed Control in a Rice Cropping System. Visual Weed Control (%)
- 21 Compound A Compound of DAA Benzyl Ester Formula (II) BRAPP
gae/ha gai/ha Obs Exp 8 0 70 -- 0 37.5 0 -- 0 75 0 -- 0 150 0 -- 8
37.5 80 70 8 75 90 70 8 150 90 70 Visual Weed Control (%) - 21
Compound A Compound of DAA Benzyl Ester Formula (II) ECHCG gae/ha
gai/ha Obs Exp 16 0 80 -- 32 0 95 -- 0 150 0 -- 16 150 95 80 32 150
99 95 Visual Weed Control (%) - 21 Compound A Compound of DAA
Benzyl Ester Formula (II) LEFCH gae/ha gai/ha Obs Exp 32 0 25 -- 0
37.5 0 -- 0 75 0 -- 0 150 0 -- 32 37.5 40 25 32 75 50 25 32 150 30
25 Visual Weed Control (%) - 21 Compound A Compound of DAA Benzyl
Ester Formula (II) CYPIR gae/ha gai/ha Obs Exp 8 0 50 0 37.5 0 0 75
0 8 37.5 70 50 8 75 100 50 BRAPP Brachiaria platyphylla (Groseb.)
Nash, broadleaf signalgrass. CYPES Cyperus esculentus L., nutsedge,
yellow CYPIR Cyperus iria L., flatsedge, rice DIGSA Digitaria
sanguinalis (L.) Scop.; crabgrass, large ECHCG Echinochloa
crus-galli (L.) Beauv.; barnyardgrass ECHCO Echinochloa colona (L.)
Link; junglerice IPOHE Ipomoea hederacea Jacq.; morningglory,
ivyleaf LEFCH Leptochloa chinensis (L.) Nees; sprangletop, Chinese
SCPJU Schoenoplectus juncoides Roxb., bulrush, Japanese gae/ha =
grams acid equivalent per hectare gai/ha = grams active ingredient
per hectare Obs = observed value Exp = expected value as calculated
by Colby's equation DAA = days after application
Example II
Evaluation of In-Water Applied Herbicidal Mixtures for Weed Control
in Transplanted Paddy Rice
[0165] Weed seeds or nutlets of the desired test plant species were
planted in puddled soil (mud) prepared by mixing a shredded,
non-sterilized mineral soil (50.5 percent silt, 25.5 percent clay,
and 24 percent sand, with a pH of about 7.6 and an organic matter
content of about 2.9 percent) and water at a 1:1 volumetric ratio.
The prepared mud was dispensed in 365 mL aliquots into 16-ounce
(oz.) non-perforated plastic pots with a surface area of 86.59
square centimeters leaving a headspace of 3 centimeters in each
pot. Rice seeds were planted in Sun Gro MetroMix.RTM. 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 plug trays.
Seedlings at the second or third leaf stage of growth were
transplanted into 860 mL of mud contained in 32-oz. non-perforated
plastic pots with a surface area of 86.59 cm.sup.2 4 days prior to
herbicide application. The paddy was created by filling the
headspace of the pots with 2.5 to 3 cm of water. 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 4-22 days in a greenhouse with an approximate 14 h
photoperiod which was maintained at about 29'C during the day and
about 26.degree. C. during the night. Nutrients were added as
Osmocote.RTM. (17:6:10, N:P:K+minor nutrients) at 2 g per cup.
Water was added on a regular basis to maintain the paddy flood, and
supplemental lighting was provided with overhead metal halide
1000-Watt lamps as necessary. The plants were employed for testing
when they reached the first through fourth true leaf stage.
[0166] Treatments consisted of the acid or esters of
4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxy-phenyl)pyridine--
2-carboxylic acid (compound A) each formulated as an SC (suspension
concentrate) and various fungicidal components alone and in
combination. Forms of compound A were applied on an acid equivalent
basis.
Forms of compound A (compound of formula I) tested include:
##STR00033##
Other fungicidal components were applied on an active ingredient
basis and consisted of flutolanil (technical grade material),
probenazole (technical grade material), and tricyclazole formulated
as Beam.RTM..
[0167] Treatment requirements for each compound or fungicidal
component were calculated based upon the rates being tested, the
concentration of active ingredient or acid equivalent in the
formulation, an application volume of 2 mL per component per pot,
and an application area of 86.59 cm.sup.2 per pot.
[0168] For formulated compounds, a measured amount was placed in an
individual 100 or 200 mL glass vial and was dissolved in a volume
of 1.25% (v/v) Agri-Dex.RTM. crop oil concentrate to obtain
application solutions. If the test compound did not dissolve
readily, the mixture was warmed and/or sonicated.
[0169] For technical grade compounds, a weighed amount can be
placed in an individual 100 to 200 mL glass vial and dissolved in a
volume of acetone to obtain concentrated stock solutions. If the
test compound does not dissolve readily, the mixture can be warmed
and/or sonicated. The concentrated stock solutions obtained can be
diluted with an equivalent volume of an aqueous mixture containing
2.5% (v/v) crop oil concentrate so that the final application
solutions contain 1.25% (v/v) crop oil concentrate.
[0170] Applications were made by injecting with a pipetter
appropriate amounts of the application solutions, individually and
sequentially, into the aqueous layer of the paddy. Control plants
were treated in the same manner with the solvent blank.
Applications were made so that all treated plant material received
the same concentrations of acetone and crop oil concentrate.
[0171] The treated plants and control plants were placed in a
greenhouse as described above and water was added as needed to
maintain a paddy flood. After approximately 3 weeks the condition
of the test plants as compared with that of the untreated plants
was determined visually and scored on a scale of 0 to 100 percent
where 0 corresponds to no injury or growth inhibition and 100
corresponds to complete kill.
[0172] 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.).
[0173] 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)
[0174] A=observed efficacy of active ingredient A at the same
concentration as used in the mixture.
[0175] B=observed efficacy of active ingredient B at the same
concentration as used in the mixture.
[0176] Some of the compounds tested, application rates employed,
plant species tested, and results are given in Tables 23-26.
TABLE-US-00023 TABLE 23 Synergistic Activity of In-Water Applied
Compound A Benzyl Ester and a Compound of Formula (II) Compositions
on Weed Control in a Transplanted Rice Cropping System. Visual Weed
Control (%) - 21 Compound A DAA Benzyl Ester Flutolanil ECHOR
gae/ha gai/ha Obs Exp 8 0 15 -- 16 0 20 -- 0 140 0 -- 0 560 0 -- 8
140 45 15 16 140 75 20 8 560 30 15 16 560 50 20 Visual Weed Control
(%) - 21 Compound A DAA Benzyl Ester Flutolanil LEFCH gae/ha gai/ha
Obs Exp 8 0 0 -- 16 0 0 -- 0 140 0 -- 8 140 20 0 16 140 20 0
TABLE-US-00024 TABLE 24 Synergistic Activity of In-Water Applied
Compound A Benzyl Ester and Probenazole Compositions on Weed
Control in a Transplanted Rice Cropping System. Visual Weed Control
(%) - 21 Compound A DAA Benzyl Ester Probenazole CYPRO gae/ha
gai/ha Obs Exp 8 0 40 -- 0 1000 0 -- 0 2000 0 -- 0 4000 0 -- 8 1000
95 40 8 2000 80 40 8 4000 75 40
TABLE-US-00025 TABLE 25 Synergistic Activity of In-Water Applied
Compound A Acid and Tricyclazole Compositions on Weed Control in a
Transplanted Rice Cropping System. Visual Weed Control (%) - 22
Compound A DAA Acid Tricyclazole CYPRO gae/ha gai/ha Obs Exp 10.6 0
0 -- 21.2 0 25 -- 42.4 0 95 -- 0 200 0 -- 10.6 200 80 0 21.2 200 70
25 42.4 200 90 95
TABLE-US-00026 TABLE 26 Synergistic Activity of In-Water Applied
Compound A Benzyl Ester and Tricyclazole Compositions on Weed
Control in a Transplanted Rice Cropping System. Visual Weed Control
(%) - 19 Compound A DAA Benzyl Ester Tricyclazole CYPRO gae/ha
gai/ha Obs Exp 8 0 20 -- 16 0 88 -- 32 0 87 -- 0 375 0 -- 0 750 0
-- 8 375 10 20 16 375 83 88 32 375 98 87 8 750 50 20 16 750 80 88
32 750 88 87 Visual Weed Control (%) - 22 Compound A DAA Benzyl
Ester Tricyclazole FIMMI gae/ha gai/ha Obs Exp 4.38 0 50 -- 8.75 0
80 -- 17.5 0 100 -- 0 200 0 -- 4.38 200 100 50 8.75 200 100 80 17.5
200 100 100 Visual Weed Control (%) - 19 Compound A DAA Benzyl
Ester Tricyclazole LEFCH gae/ha gai/ha Obs Exp 8 0 3 -- 16 0 8 -- 0
187.5 0 -- 0 750 0 -- 8 187.5 3 3 16 187.5 20 8 8 750 17 3 16 750
13 8 CYPRO Cyperus rotundus L.; nutsedge, purple ECHCO Echinochloa
colona (L.) Link; junglerice FIMMI Fimbristylis miliacea (L.) Vahl;
globe fringerush LEFCH Leptochloa chinensis (L.) Nees; sprangletop,
Chinese gae/ha = grams acid equivalent per hectare gai/ha = grams
active ingredient per hectare Obs = observed value Exp = expected
value as calculated by Colby's equation DAA = days after
application
* * * * *