Language selection

Search

Patent 3127303 Summary

Third-party information liability

Some of the information on this Web page has been provided by external sources. The Government of Canada is not responsible for the accuracy, reliability or currency of the information supplied by external sources. Users wishing to rely upon this information should consult directly with the source of the information. Content provided by external sources is not subject to official languages, privacy and accessibility requirements.

Claims and Abstract availability

Any discrepancies in the text and image of the Claims and Abstract are due to differing posting times. Text of the Claims and Abstract are posted:

  • At the time the application is open to public inspection;
  • At the time of issue of the patent (grant).
(12) Patent Application: (11) CA 3127303
(54) English Title: HERBICIDAL MIXTURES COMPRISING IMAZETHAPYR, IMAZAMOX AND FOMESAFEN
(54) French Title: MELANGES HERBICIDES CONTENANT DE L'IMAZETHAPYR, DE L'IMAZAMOX ET DU FOMESAFENE
Status: Allowed
Bibliographic Data
(51) International Patent Classification (IPC):
  • A01N 43/50 (2006.01)
  • A01N 41/06 (2006.01)
  • A01N 43/88 (2006.01)
  • A01P 13/00 (2006.01)
(72) Inventors :
  • ZAGAR, CYRILL (United States of America)
  • BEGLIOMINI, EDSON (Singapore)
  • BEOHAR, ABHISHEK (India)
  • CHANDOLA, AJAY (India)
  • GANIGER, SATISH (Singapore)
  • KANDRU, SUDHAKAR (Germany)
  • OTURKAR, YOGESH (India)
  • RATHORE, YOGENDRA (India)
  • SANYAL, NILANJAN (India)
(73) Owners :
  • BASF AGROCHEMICAL PRODUCTS B.V.
(71) Applicants :
  • BASF AGROCHEMICAL PRODUCTS B.V.
(74) Agent: ROBIC AGENCE PI S.E.C./ROBIC IP AGENCY LP
(74) Associate agent:
(45) Issued:
(22) Filed Date: 2015-01-05
(41) Open to Public Inspection: 2015-07-16
Examination requested: 2021-08-10
Availability of licence: N/A
Dedicated to the Public: N/A
(25) Language of filing: English

Patent Cooperation Treaty (PCT): No

(30) Application Priority Data:
Application No. Country/Territory Date
14154658.0 (European Patent Office (EPO)) 2014-02-11
61/924,729 (United States of America) 2014-01-08

Abstracts

English Abstract


The present invention relates to ternary herbicidally active compositions,
which comprise a)
5-ethyl-2-[(RS)-4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl]nicotinic acid
(common
name: imazethapyr) and 2-[(RS)-4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl]-5-
methoxymethylnicotinic acid (common name: imazamox) and
b) the herbicide 5-(2-chloro- a , a , a -trifluoro-p-tolyloxy)-N-mesyl-2-
nitrobenzamide
(common name: fomesafen).


Claims

Note: Claims are shown in the official language in which they were submitted.


- 39 -
Claims
1. Herbicidal compositions comprising:
a) a herbicide A, which is the combination of imazethapyr, or agriculturally
acceptable salts thereof and imazamox, or agriculturally acceptable salts
thereof, and
b) a herbicide B which is fomesafen, or agriculturally acceptable salts
thereof.
2. Compositions as claimed in claim 1, wherein the relative amount
of the
herbicide A to the herbicide B is from 20:1 to 1:100.
3. Composition as claimed in claim 1, wherein the relative amount
of the
herbicide A to the herbicide B is from 10:1 to 1:40.
4. Composition as claimed in claim 1, wherein the relative amount of the
herbicide A to the herbicide B is from 5:1 to 1:20.
5. Use of the compositions as claimed in any one of claims 1 to 4 for
controlling undesirable vegetation.
6. The use of the compositions as claimed in claim 5 wherein the
undesirable vegetation is monocotyledonous and/or dicotyledonous weeds.
7. The use of the composition as claimed in claim 5 or 6 wherein the
undesirable vegetation are weeds selected from the group consisting of
Date Recue/Date Received 2021-08-10

- 40 -
Acalypha spec., Commelina spec., Dinebra spec., Cynotis spec., Parthenium
spec., Physalis spec., Digera spec., Phalaris spec., Leptochloa spec.,
Echinochloa
spec., Setaria spec., Digitaria spec., Panicum spec., Brachiaria spec.,
Ambrosia
spec., Geranium spec., Abutilon spec., Sesbania spec., Conyza spec.,
Convolvulus spec., and Polygonum spec.
8. The use as claimed in any one of claims 5 to 7 for controlling
undesirable
vegetation in crop plants.
9. The use as claimed in claim 8, wherein the crop plants are leguminous
crops.
10. The use as claimed in claim 9, wherein the crop plants are leguminous
crops selected from soybean, green gram, black gram, peas, cluster beans,
pulse
crops, and peanut.
11. The use as claimed in claim 10, wherein the crop plant is soybean.
12. The use as claimed in any one of claims 8 to 11, wherein the crop
plants
are tolerant to acetohydroxyacid synthase inhibiting herbicides.
13. The use as claimed in claim 8, wherein the crop plants are tolerant to
acetohydroxyacid synthase inhibiting herbicides selected from the group
consisting of wheat, barley, canola, corn, lentils, oilseed rape, rice,
soybean,
sunflower, and mixtures thereof.
Date Recue/Date Received 2021-08-10

- 41 -
14. A method for controlling undesirable vegetation, which comprises
applying a combination of a) the herbicide A, which is the combination of
imazethapyr, or agriculturally acceptable salts thereof and imazamox, or
agriculturally acceptable salts thereof, and b) the herbicide B which is
bentazone, or agriculturally acceptable salt thereof to act on plants to be
controlled or their habitat.
15. The method for controlling undesired vegetation as claimed in claim 14,
which comprises applying the combination before, during and/or after the
emergence of the undesirable plants; the herbicide A and the at least one
herbicide B being applied simultaneously or in succession.
16. The method for controlling undesired vegetation as claimed in claim 14
or
15, wherein the combination is the herbicidal compositions as claimed in any
one of claims 1 to 4.
17. An herbicide formulation comprising the composition as claimed in any
one of claims 1 to 4 and at least one solid or liquid carrier.
Date Recue/Date Received 2021-08-10

Description

Note: Descriptions are shown in the official language in which they were submitted.


- 1 -
Herbicidal mixtures comprising imazethapyr, imazamox and fomesafen
Field of the invention
The present invention relates to ternary herbicidally active compositions,
which comprise
a) 5-ethy1-2-[(RS)-4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-y]nicotinic acid
(common
name: imazethapyr) and 2-[(RS)-4-isopropy1-4-methyl-5-oxo-2-imidazolin-2-y1]-5-
methoxymethylnicotinic acid (common name: imazamox) and
b) 5-(2-chloro- a , a , a -trifluoro-p-tolyloxy)-N-mesy1-2-nitrobenzamide
(common name:
.. fomesafen).
Background of the invention
In crop protection, it is desirable in principle to increase the specificity
and the reliability
of the action of active compounds. In particular, it is desirable for the crop
protection
product to control the harmful plants effectively and, at the same time, to be
tolerated by
the useful plants in question.
5-ethy1-2-[(RS)-4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-y]nicotinic acid
(common
name: imazethapyr; formula I) is an active compound from the group of
imidazolinone
herbicides, which are known e.g. from Shaner, D. L., 0 Conner, S.L, The
Imidazolinone
Herbicides, CRC Press Inc., Boca Raton, Florida 1991 and also from The
Compendium of
Pesticide Common Names as described on the BCPC website.
Date Recue/Date Received 2021-08-10

- 2 -
H3C
C3
HC H
HO 0
I0
H3C N
2-[(RS)-4-isopropy1-4-methyl-5-oxo-2-imidazolin-2-y1]-5-methoxymethylnicotinic
acid
(common name: imazamox; formula II) is an active compound from the group of
imidazolinone herbicides, which are known e.g. from Shaner, D. L. 0 Conner,
S.L The
Imidazolinone Herbicides, CRC Press Inc., Boca Raton, Florida 1991 and also
from The
Compendium of Pesticide Common Names as described on the BCPC website.
CH2-0
II
CH3 CH __________
CH, CH,
5-(2-chloro- a , a , a -trifluoro-p-tolyloxy)-N-mesy1-2-nitrobenzamide (common
name:
fomesafen, formula III) is an active compound that inhibits protoporphyrinogen
IX oxidase
(FPO).
00
rd-g-cH3
Fsc a No2
Date Recue/Date Received 2021-08-10

- 3 -
Herbicidal combinations of imazethapyr and imazamox are known to be highly
effective
as pre- and post-emergence herbicides; for example, such a combination is
commercialized under the brand name Odyssey . Still, in some cases such
combinations
do not provide a sufficient control of the relevant harmful plants and their
activity at low
application rates is not always satisfactory. Apart from that, their
compatibility with
certain dicotyledonous crop plants such as soybean, peanuts or other pulse or
leguminous crops is not always satisfactory, i.e. in addition to the harmful
plants, the crop
plants are also damaged to an extent which is not acceptable.
Though it is in principle possible to spare crop plants by lowering the
application rates,
the extend of the control of harmful plants is naturally also reduced.
Summary of the invention
In one aspect, there is provided an herbicidal compositions comprising:
a) a herbicide A, which is the combination of imazethapyr, or agriculturally
acceptable
salts thereof and imazamox, or agriculturally acceptable salts thereof, and
b) a herbicide B which is fomesafen, or agriculturally acceptable salt
thereof.
In another aspect, there is provided a method for controlling undesirable
vegetation,
which comprises applying a combination of a) the herbicide A, which is the
combination
of imazethapyr, or agriculturally acceptable salts thereof and imazamox, or
agriculturally
acceptable salts thereof, and b) the herbicide B which is fomesafen, or
agriculturally
acceptable salt thereof to act on plants to be controlled or their habitat.
Date Recue/Date Received 2021-08-10

- 4 -
Detailed description of the invention
It is an object of the present invention to provide herbicidal compositions,
which show
enhanced herbicide action against undesirable harmful plants, in particular
against
Acalypha species such as Acalypha indica, Dinebra species such as Dinebra
Arab/ca,
Cynotis spec such as Cynotis axillaris, Parthenium spec such as Parthenium
hysterophorus, Physalis spec such as Physalis minima, Digera spec such as
Digera
arvensis, Alopecurus myosuroides, Apera spicaventi, Ambrosia spec. such as
Ambrosia
artemisiifolia, Conyza spec. such as Conyza canadensis, Convolvulus spec. such
as
Convolvulus arvensis, Echinochloa spec. such as Echinochloa colonum and
Echinochloa
crus-galli, Rottboellia cochinchinensis, Digitaria spec. such as Digitaria
sanguinalis,
Eleusine indica, Saccharum spontaneum, Cynodon dactylon, Euphorbia hirta,
Euphorbia
geniculata, Commelina benghalensis, Commelina communis, Celosia argentea,
Xanthium
strumarium, Papa ver rhoeas, Polygonum spec. such as Polygonum persicaria,
Pan/cum
spec. such as Pan/cum mllaceum, Geranium spec. such as Geranium dissectum,
Brass/ca
spec, Avena fatua, Bromus spec., Echinocloa spec., Leptochloa spec. such as
Leptochloa
fusca, Lo//um spec., Phalaris spec. such as Phalaris canariensis, Setaria
spec. such as
Setaria faberi, Sesbania spec. such as Sesbania exaltataõ Brach/aria spec.
such as
Brach/aria decumbens, Amaranthus spec., Chenopodium spec., Abut//on spec. such
as
Abut//on theophrasti, Gal/um aparine, Veronica spec., or Solanum spec. and/or
to improve
their compatibility with crop plants, such as soybean, peanut, pea, bean,
lentil, green
gram, black gram, cluster bean, fenugreek, other pulse or leguminous crops, or
crops
which are tolerant to the action of acetohydroxyacid synthase inhibiting
herbicides, such
Date Recue/Date Received 2021-08-10

- 5 -
as for example Cearfied wheat, Cearfied barley, Cearfied corn, Cearfied
lentil,
Cearfied oilseed rape or canola, Cearfied rice, Cutivance soybean and/or
Cearfied sunflower. The composition should also have a good pre-emergence
herbicidal activity.
We consider this object to be achievable, by herbicidally active compositions
comprising
a) the combination of imazethapyr, agriculturally acceptable salts thereof and
imazamox, agriculturally acceptable salts thereof (collectively hereinafter
also
referred to as herbicide A); and
b) at least one herbicide B selected from the group of fomesafen,
agriculturally
acceptable salts thereof, sulfentrazone, agriculturally acceptable salts
thereof
and bentazone and agriculturally acceptable salts thereof.
The invention relates in particular to compositions in the form of
herbicidally active
compositions as defined above.
The invention furthermore relates to the use of compositions as defined herein
for
controlling undesirable vegetation in crops. When using the compositions of
the invention
for this purpose the herbicide A and the at least one herbicide B can be
applied
simultaneously or in succession in crops, where undesirable vegetation may
occur.
The invention furthermore relates to the use of compositions as defined herein
for
controlling undesirable vegetation in crops which, by genetic engineering or
by breeding,
Date Recue/Date Received 2021-08-10

- 6 -
are tolerant to one or more herbicides, e.g. acetohydroxyacid synthase
inhibiting
herbicides such as imazethapyr, and/or pathogens such as plant-pathogenous
fungi,
and/or to attack by insects; preferably tolerant to one or more herbicides
that act as
acetohydroxyacid synthase inhibitors.
The invention furthermore relates to a method for controlling undesirable
vegetation,
which comprises applying an herbicidal composition according to the present
invention to
the undesirable plants. Application can be done before, during and/or after,
preferably
during and/or after, the emergence of the undesirable plants. The herbicide A
and the at
least one herbicide B can be applied simultaneously or in succession.
The invention in particular relates to a method for controlling undesirable
vegetation in
crops, which comprises applying an herbicidal composition according to the
present
invention in crops where undesirable vegetation occurs or might occur.
The invention furthermore relates to a method for controlling undesirable
vegetation,
which comprises allowing a composition according to the present invention to
act on
plants, their habitat or on seed.
In the methods of the present invention it is immaterial whether the
combination of
herbicide A and the at least one herbicide B are formulated and applied
jointly or
separately, and, in the case of separate application, in which order the
application takes
place. It is only necessary, that the combination of herbicide A and the at
least one
Date Recue/Date Received 2021-08-10

- 7 -
herbicide B are applied in a time frame, which allows simultaneous action of
the active
ingredients on the plants.
In the methods of the present invention it is further immaterial whether the
components
of herbicide A, i.e. imazethapyr and imazamox and the at least one herbicide
are
formulated and applied jointly or separately, and, in the case of separate
application, in
which order the application takes place. It is only necessary, that the
components of
herbicide A and the at least one herbicide B are applied in a time frame,
which allows
simultaneous action of the active ingredients on the plants.
The invention also relates to an herbicide formulation, which comprises a
herbicidally
active composition as defined herein and at least one carrier material,
including liquid
and/or solid carrier materials.
It is believed that the compositions according to the invention have better
herbicidal
activity against harmful plants than would have been expected by the
herbicidal activity
of the individual compounds. In other words, the joint action of the
imazethapyr +
imazamox combination and the at least one herbicide B results in an enhanced
activity
against harmful plants in the sense of a synergy effect (synergism). For this
reason, the
compositions can, based on the individual components, be used at lower
application rates
to achieve a herbicidal effect comparable to the individual components. The
compositions
of the invention also show an accelerated action on harmful plants, i.e.
damaging of the
harmful plants is achieved more quickly in comparison with application of the
individual
Date Recue/Date Received 2021-08-10

- 8 -
herbicides. Moreover, the compositions of the present invention provide good
pre-
emergence herbicidal activity, i.e. the compositions are particularly useful
for
combating/controlling harmful plants before their emergence. Apart from that,
the
compositions of the present invention show good crop compatibility, i.e. their
use in crops
leads to a reduced damage of the crop plants.
As used herein, the terms "controlling" and "combating" are synonyms.
As used herein, the terms "undesirable vegetation" and "harmful plants" are
synonyms.
Where reference is made to imazethapyr, this includes the free base as well as
agriculturally acceptable salts thereof.
Examples of agriculturally acceptable salts of imazethapyr include alkaline or
earth
alkaline metals or ammonium or organoammonium salts, for instance,
sodium, potassium, ammonium and isopropyl ammonium. Particularly preferred is
imazethapyr ammonium salt. Reference to a salt includes the anhydrous form as
well as
hydrated forms thereof.
Where reference is made to imazamox, this includes the free base as well as
agriculturally acceptable salts thereof.
Examples of agriculturally acceptable salts of imazamox include alkaline or
earth alkaline
Date Recue/Date Received 2021-08-10

- 9 -
metals or ammonium or organoammonium salts, for instance, sodium, potassium,
ammonium and isopropyl ammonium. Particularly preferred is imazamox ammonium
salt.
Reference to a salt includes the anhydrous form as well as hydrated forms
thereof.
Where reference is made to fomesafen, this includes the free base as well as
agriculturally acceptable salts thereof.
Examples of agriculturally acceptable salts of fomesafen include alkaline or
earth alkaline
metals or ammonium or organoammonium salts, for instance, sodium, potassium,
ammonium and isopropyl ammonium. Particularly preferred is fomesafen sodium
salt.
Reference to a salt includes the anhydrous form as well as hydrated forms
thereof.
Where reference is made to sulfentranzone, this includes the free base as well
as
agriculturally acceptable salts thereof.
Examples of agriculturally acceptable salts of sulfentranzone include alkaline
or earth
alkaline metals or ammonium or organoammonium salts, for instance, sodium,
potassium,
ammonium and isopropyl ammonium. Reference to a salt includes the anhydrous
form as
well as hydrated forms thereof.
Where reference is made to bentazone, this includes the free base as well as
agriculturally acceptable salts thereof.
Date Recue/Date Received 2021-08-10

- 10 -
Examples of agriculturally acceptable salts of bentazone include alkaline or
earth alkaline
metals or ammonium or organoammonium salts, for instance, lithium, sodium,
potassium,
magnesium, calcium, ammonium, methylammonium, dimethylammonium,
methyltrioctylammonium and isopropyl ammonium as well as the diethanolamine
and
choline salts. Particularly preferred is bentazone sodium salt. Reference to a
salt includes
the anhydrous form as well as hydrated forms thereof.
The compositions of the invention comprise the imazethapyr + imazamox
combination as
a first component a).
As a second component b), the compositions of the invention comprise at least
one
herbicide B which is selected from the at least one herbicide B from the group
of
fomesafen, sulfentrazone or bentazone. In one embodiment a herbicide B is
present, in
another embodiment two herbicides B are present.
The herbicide B is selected from the group of fomesafen, sulfentrazone or
bentazone.
Imazethapyr may be present in the form of its racemate or in the form of the
pure R-or S-
enantiomers (including salts as defined above). Particularly preferred is the
racemate
and/or R-imazethapyr.
Imazamox may be present in the form of its racemate or in the form of the pure
R-or S-
enantiomer (including salts as defined above). Particularly suitable is R-
imazamox.
Date Recue/Date Received 2021-08-10

- 11 -
Particularly preferred is the racemate.
In one embodiment the imazethapyr/imazamox combination is combined with
fomesafen.
In the compositions of the present invention, imazethapyr and imazamox are
present in a
weight ratio preferably in the range from 100:1 to 1:100, in particular in the
range from 5:1
to 1:5, more preferably from 2:1 to 1:2 and even more preferably 1:1.
In the compositions of the present invention the relative weight ratio of
herbicide A to
herbicide B is preferably in the range from 20:1 to 1:100, in particular in
the range from
10:1 to 1:40 and more preferably from 5:1 to 1:20. Accordingly, in the methods
and uses of
the invention, herbicide A and the at least one herbicide B are applied within
these weight
ratios.
In the composition comprising herbicide A and fomesafen the relative weight
ratio of
herbicide A to fomesafen is preferably in the range of 10:1 to 1:100, more
preferably 5:1
to 1:20 and most preferably 1:1 to 1:10.
The compositions of the invention may also comprise, as a component c), one or
more
safeners. Safeners, also termed as herbicide safeners are organic compounds
which in
some cases lead to better crop plant compatibility when applied jointly with
specifically
acting herbicides. Some safeners are themselves herbicidally active. In these
cases, the
safeners act as antidote or antagonist in the crop plants and thus reduce or
even prevent
Date Recue/Date Received 2021-08-10

- 12 -
damage to the crop plants. However, in the compositions of the present
invention,
safeners are generally not required. Therefore, a preferred embodiment of the
invention
relates to compositions which contain no safener or virtually no safener (i.e.
less than 1 %
by weight, based on the total amount of herbicide A and herbicide B).
Suitable safeners, which can be used in the compositions according to the
present
invention are known in the art, e.g. from The Compendium of Pesticide Common
Namesas described on the BCPC website; Farm Chemicals Handbook 2000 Vol. 86,
Meister Publishing Company, 2000; B. Hock, C. Fedtke, R. R. Schmidt,
Herbizide, Georg
Thieme Verlag, Stuttgart 1995; W. H. Ahrens, Herbicide Handbook, 7th Edition,
Weed
Science Society of America, 1994; and K. K. Hatzios, Herbicide Handbook,
Supplement to
7th Edition, Weed Science Society of America, 1998.
Safeners include benoxacor, cloquintocet, cyometrinil, cyprosulfamide,
dichlormid,
dicyclonon, dietholate, fenchlorazole, fenclorim, flurazole, fluxofenim,
furilazole,
isoxadifen, mefenpyr, mephenate, naphthalic anhydride, 2,2,5-trimethy1-3-
(dichloracety1)-
1,3-oxazolidine, 4-(dichloroacety1)-1-oxa-4-azaspiro[4.5]decane and
oxabetrinil, as well
as thereof agriculturally acceptable salts and, provided they have a carboxyl
group, their
agriculturally acceptable derivatives. 2,2,5-Trimethy1-3-(dichloroacety1)-1,3-
oxazolidine
[CAS No. 52836-31-4] is also known under the name R-29148.4-(Dichloroacety1)-1-
oxa-
4-azaspiro[4.5]decane [CAS No. 71526-07-03] is also known under the names AD-
67 and
MON 4660.
As safener, the compositions according to the invention particularly
preferably comprise
Date Recue/Date Received 2021-08-10

- 13 -
at least one of the compounds selected from the group of benoxacorõ
cloquintocet,
cyprosulfamide, dichlormid, fenchlorazole, fenclorim, fluxofenim, furilazole,
isoxadifen,
mefenpyr, naphthalic anhydride, 2,2,5-trimethy1-3-(dichloroacety1)-1,3-
oxazolidine, and 4-
(dichloroacety1)-1-oxa-4-azaspiro[4.5]decane and oxabetrinil; and the
agriculturally
acceptable salt thereof and, in the case of compounds having a COOH group, an
agriculturally acceptable derivative as defined below.
A preferred embodiment of the invention relates to compositions which contain
no
safener or virtually no safener (i.e. less than 1 % by weight, based on the
total amount of
herbicide A and the at least one herbicide B) is applied.
If the compounds of herbicidally active compounds mentioned as herbicides B
and
safeners (see below) have functional groups, which can be ionized, they can
also be used
in the form of their agriculturally acceptable salts. In general, the salts of
those cations
are suitable whose cations have no adverse effect on the action of the active
compounds
("agriculturally acceptable").
In general, the salts of those cations are suitable whose cations have no
adverse effect
on the action of the active compounds ("agriculturally acceptable"). Preferred
cations are
the ions of the alkali metals, preferably of lithium, sodium and potassium, of
the alkaline
earth metals, preferably of calcium and magnesium, and of the transition
metals,
preferably of manganese, copper, zinc and iron, furthermore ammonium and
substituted
ammonium (hereinafter also termed as organoammonium) in which one to four
hydrogen
Date Recue/Date Received 2021-08-10

- 14 -
atoms are replaced by C1-C4-alkyl, hydroxy-C1-C4-alkyl, C1-C4-alkoxy-C1-C4-
alkyl,
hydroxy-C1-C4-alkoxy-C1-C4-alkyl, phenyl or benzyl, preferably ammonium,
methylammonium, isopropylammonium, dimethylammonium, diisopropylammonium,
trimethylammonium, tetramethylammonium, tetraethylammonium,
tetrabutylammonium,
2-hydroxyethylammonium, 2-(2-hydroxyethoxy)eth-1-ylammonium, di(2-hydroxyeth-1-
yl)ammonium, benzyltrimethylammonium, benzyltriethylammonium, furthermore
phosphonium ions, sulfonium ions, preferably tri(C1-C4-alkyl)sulfonium such as
trimethylsulfonium, and sulfoxonium ions, preferably tri(C1-C4-
alkypsulfoxonium.
In the compositions according to the invention, the compounds that carry a
carboxyl
group can also be employed in the form of agriculturally acceptable
derivatives, for
example as amides such as mono- or di-C1-C6-alkylamides or arylamides, as
esters, for
example as allyl esters, propargyl esters, C1-C10-alkyl esters or alkoxyalkyl
esters, and
also as thioesters, for example as C1-C10-alkyl thioesters. Preferred mono-
and di-C1-
C6-alkylamides are the methyl- and the dimethylamides. Preferred arylamides
are, for
example, the anilidines and the 2-chloroanilides. Preferred alkyl esters are,
for example,
the methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, mexyl (1-
methylhexyl) or
isooctyl (2-ethylhexyl) esters. Preferred C1-C4-alkoxy-C1-C4-alkyl esters are
the
straight-chain or branched C1-C4-alkoxyethyl esters, for example the
methoxyethyl,
ethoxyethyl or butoxyethyl esters. An example of the straight-chain or
branched C1-C10-
alkyl thioesters is the ethyl thioester. Preferred derivatives are the esters.
The compositions of the present invention are suitable for controlling a large
number of
Date Recue/Date Received 2021-08-10

- 15 -
harmful plants, including monocotyledonous weeds, in particular annual weeds
such as
gramineous weeds (grasses) including Echinochloa species such as barnyardgrass
(Echinochloa crusgalli var. crus-galk) or Echinochloa colonum, Leptochloa
species such
as Leptochloa fusca, Digitaria species such as crabgrass (Digitaria
sanguinalis), Setaria
species such as green foxtail (Setaria viridis) and giant foxtail (Setaria
faberii), Sorghum
species such as johnsongrass (Sorghum halepense Pers.), Avena species such as
wild
oats (Avena fatua), Cenchrus species such as Cenchrus echinatus, Bromus
species,
Lolium species, Phalaris species such as Phalaris canariensis, Eriochloa
species,
Pan/cum species such as Pan/cum miliaceum, Brach/aria species such as
Brach/aria
decumbens, annual bluegrass (Poa annua), blackgrass (Alopecurus myosuroides),
Aegllops cylindrica, Agropyron repens, Apera spica-venti, Eleusine indica,
Cynodon
dactylon, Rottboellia cochinchinensis, Dinebra arabica, Saccharum spontaneum,
and the
like.
The compositions of the present invention are particularly suitable for
controlling the
monocotyledonous weeds selected from Echinochloa species such as barnyardgrass
(Echinochloa crus-gall/) or Echinochloa colonum, Leptochloa species such as
Leptochloa
fusca, Phalaris species such as Phalaris canariensis, Setaria species such as
green foxtail
(Setaria Digitaria species such as crabgrass (Digitaria sanguinalis),
Pan/cum
species such as Pan/cum miliaceum and Brach/aria species such as Brach/aria
decumbens, Dinebra species such as Dinebra arabica.
The compositions of the present invention are also suitable for controlling a
large number
Date Recue/Date Received 2021-08-10

- 16 -
of dicotyledonous weeds, in particular broad leaf weeds including Acalypha
species such
as Acalypha indica, Polygonum species such as wild buckwheat (Polygonum
convolvolus)
or Polygonum persicaria, Amaranthus species such as pigweed (Amaranthus
retroflexus)
or (Amaranthus viridis), Chenopodium species such as common lambsquarters
(Chenopodium album L.), Sida species such as prickly sida (Sida spinosa L.),
Ambrosia
species such as common ragweed (Ambrosia artemisiifolia), Acanthospermum
species,
Anthemis species, Atriplex species, Cirsium species, Con volvulus species such
as
Con volvulus arvensis, Conyza species such as Conyza canadensis, Cassia
species,
Commelina species such as for example Commelina communis or Commelina
benghalensis, Datura species, Euphorbia species such as for example Euphorbia
hirta or
Euphorbia geniculata, Geranium species such as Geranium dissectum, Galinsoga
species,
morningglory (Ipomoea species), Lamium species, Malva species, Matricaria
species,
Sysimbrium species, Solanum species, Xanthium species such as for example
Xanthium
strumiarium, Veronica species, Viola species, common chickweed (Stellaria
media),
Abutllon species such as velvetleaf (Abutllon theophrash), Sespania species
such as
Hemp sesbania (Sesbania exaltata Cory), Anoda cristata, Bidens pllosa,
Brassica kaber,
Capsella bursa-pastoris, Centaurea cyanus, Galeopsis tetrahit, Galium aparine,
Helianthus annuus, Desmodium tortuosum, Kochia scoparia, Mercurialis annua,
Myosotis
arvensis, Papa ver rhoeas, Raphanus raphanistrum, Salsola kali, Sinapis
arvensis, Sonchus
arvensis, Thlaspi arvense, Tagetes minuta, Richardia brasiliensis, Rumex
crispus, Rumex
obtusifolius, Heracleaum sphondylium, Aethusa cynapium, Daucus carota,
Equisetum
arvense, Parthenium hysterophorus, Celosia argentea, Cynotis spec such as
Cynotis
axillaris, Parthenium spec such as Parthenium hysterophorus, Physalis spec
such as
Date Recue/Date Received 2021-08-10

- 17 -
Physalis minima, Digera spec such as Digera arvensis, and the like.
In particular, the compositions of the present invention are suitable for
controlling the
dicotyledonous weeds selected from Acalypha species such as Acalypha indica,
Commelina species such as Commelina benghalensis or Commelina communis,
Ambrosia
species such as common ragweed (Ambrosia artemisiifolia), Geranium species
such as
Geranium dissectum, Abutllon species such as velvetleaf (Abutllon theophrasb),
Sespania
species such as Hemp sesbania (Sesbania exaltata), Conyza species such as
Conyza
canadensis, Con volvulus species such as Con volvulus arvensis, Polygonum
species such
as Polygonum persicaria, Parthenium spec such as Parthenium hysterophorus,
Physalis
spec such as Physalis minima, Digera spec such as Digera arvensis, Cynotis
spec such as
Cynotis axillaris.
The herbicidal composition comprising imazethapyr, imazamox and fomesafen is
particularly suitable for controlling Acalypha species such as Acalypha
indica, Commelina
species such as Commelina benghalensis or Commelina communis, Echinochloa
spec.
such as Echinochloa crus-galli or Echinochloa colonum, Phalaris spec. such as
Phalaris
canariensis, Leptochloa spec. such as Leptochloa fusca, Ambrosia spec. such as
Ambrosia artemisiifolia, Geranium spec. such as Geranium dissectum, Sesbania
spec.
such as Sesbania exaltata, Conyza spec. such as Conyza Canadensis, convolvulus
spec.
such as Convolvulus arvensis and Polygonum spec. such as Polygonum persicaria,
Parthenium spec such as Parthenium hysterophorus, Physalis spec such as
Physalis
minima, Digera spec such as Digera arvensis, Cynotis spec such as Cynotis
axillaris,
Date Recue/Date Received 2021-08-10

- 18 -
Dinebra spec. such as Dinebra arabica.
The herbicidal composition comprising imazethapyr, imazamox and sulfentrazone
is
particularly suitable for controlling Acalypha species such as Acalypha
indica, Commelina
species such as Commelina benghalensis or Commelina communis, Echinochloa
spec.
such as Echinochloa crus-galli or Echinochloa colonum, Setaria spec. such as
Setaria
faberi, Pan/cum spec. such as Pan/cum miliaceum, Phalaris spec. such as
Phalaris
canariensis, Leptochloa spec. such as Leptochloa fusca, Geranium spec. such as
Geranium dissectum, Sesbania spec. such as Sesbania exaltata, Brachiaria spec.
such as
Brachiariadecumbens, Polygonum spec. such as Polygonum persicaria, Parthenium
spec
.. such as Parthenium hysterophorus, Physalis spec such as Physalis minima,
Digera spec
such as Digera arvensis, Cynotis spec such as Cynotis axillaris, Dinebra spec.
such as
Dinebra arabica.
The compositions of the invention are suitable for controlling weeds selected
from
.. Acalypha spec., Commelina spec., Echinochloa spec., Phalaris spec,
Leptochloa spec,
Echinochloa spec., Setaria spec., Digitaria spec., Pan/cum spec., Brach/aria
spec.
Ambrosia spec., Geranium spec. Abut/Ion spec., Sesbania spec., Conyza spec.,
Con volvulus spec. and Polygonum spec, Parthenium spec., Physalis spec.,
Digera spec.,
Dinebra spec, Cynotis spec
The compositions of the invention are particular suitable for controlling
weeds selected
from Acalypha spec., Commelina spec., Echinochloa spec., Phalaris spec,
Leptochloa
spec, Pan/cum spec., Brach/aria spec. Ambrosia spec., Geranium spec. Sesbania
spec.,
Date Recue/Date Received 2021-08-10

- 19 -
Conyza spec., Convolvulus spec. and Polygonum spec. Parthenium spec., Physalis
spec.,
Digera spec., Dinebra spec, Cynotis spec.
The compositions of the present invention are in particular useful against
annual and
perennial grasses and broad-leaved weeds in post-emergence application.
The compositions of the present invention are also suitable for controlling a
large number
of annual and perennial sedge weeds including cyperus species such as purple
nutsedge
(Cyperus rotundusL.), yellow nutsedge (Cyperus esculentusL.), hime-kugu
(Cyperus
brevifolius H.), sedge weed (Cyperus microiriaSteud), rice flatsedge (Cyperus
iriaL.), and
the like.
The compositions according to the present invention are suitable for combat-
ing/controlling common harmful plants in useful plants (i.e. in crops). The
compositions
of the present invention are generally suitable for combating/controlling
undesired
vegetation in
- Legumes (Fabaceae), including e.g. soybeans (Glycine max.), peanuts
(Arachis
hypogaea) and pulse crops such as peas including Pisum sativum, pigeon pea and
cowpea, beans including broad beans (V/c/a faba), Vigna spp., and
Phaseolusspp. and
lentils (lens culinaris var.).
- crops which are tolerant to the action of acetohydroxyacid synthase
inhibiting
herbicides, such as for example Cearfied wheat, Cearfied barley, Cearfied
corn,
Cearfied lentil, Cearfied oilseed rape or canola, Cearfied rice, Cutivance
soybean
Date Recue/Date Received 2021-08-10

- 20 -
and/or Clearfield sunflower.
The compositions of the present invention are in particular suitable for
combat-
ing/controlling undesired vegetation in soybean, peanut, pea, bean, lentil,
green gram,
black gram, cluster bean, fenugreek, other pulse or leguminous crops, or crops
which are
tolerant to the action of acetohydroxyacid synthase inhibiting herbicides,
such as for
example Cearfied wheat, Cearfied barley, Cearfied corn, Cearfied lentil,
Cearfied oilseed rape or canola, Cearfied rice, Cutivance soybean and/or
Cearfied sunflower.
The compositions of the present invention are most suitable for
combating/controlling
undesired vegetation in soybean, peanut, pea, bean, lentil, green gram, black
gram,
cluster bean, fenugreek, other pulse or leguminous crops, preferably soybean
(Glycine
max.).
If not stated otherwise, the compositions of the invention are suitable for
application in
any variety of the aforementioned crop plants.
The compositions according to the invention can also be used in crop plants
which are
tolerant to one or more herbicides owing to genetic engineering or breeding,
which are
resistant to one or more pathogens such as plant pathogenous fungi to genetic
engineering or breeding, or which are resistant to attack by insects owing to
genetic
engineering or breeding. Suitable are for example pulse or leguminous crop
plants,
Date Recue/Date Received 2021-08-10

- 21 -
preferably soybean, peanut, pea, bean, green gram, black gram, cluster bean,
fenugreek,
or lentil which are tolerant to herbicidal AHAS inhibitors, such as, for
example
imazethapyr, or pulse or leguminous crop plants, preferably soybean, peanut,
pea, bean,
green gram, black gram, cluster bean, fenugreek, or lentil which, owing to
introduction of
the gene for Bt toxin by genetic modification, are resistant to attack by
certain insects.
Most suitable are soybeans which are tolerant to herbicidal AHAS inhibitors,
such as, for
example imazethapyr or soybean plants which, owing to introduction of the gene
for Bt
toxin by genetic modification, are resistant to attack by certain insects.
The compositions of the present invention can be applied in conventional
manner by
using techniques as skilled person is familiar with. Suitable techniques
include spraying,
atomizing, dusting, spreading or watering. The type of application depends on
the
intended purpose in a well known manner; in any case, they should ensure the
finest
possible distribution of the active ingredients according to the invention.
The compositions can be applied pre- or post-emergence, i.e. before, during
and/or after
emergence of the undesirable plants. Preferably, the compositions are applied
post-
emergence, in particular after the emergence of both the crop and the
undesirable plants.
When the compositions are used in crops, they can be applied after seeding and
before or
after the emergence of the crop plants. The compositions invention can,
however, also be
applied prior to seeding of the crop plants.
In any case the components of herbicide A and the at least one herbicide B can
be
Date Recue/Date Received 2021-08-10

- 22 -
applied simultaneously or in succession.
The compositions are applied to the plants mainly by spraying, in particular
foliar
spraying. Application can be carried out by customary spraying techniques
using, for
example, water as carrier and spray liquor rates of from about 10 to 2000 I/ha
or 50 to
1000 I/ha (for example from 100 to 500 I/ha). Application of the herbicidal
compositions
by the low-volume and the ultra-low-volume method is possible, as is their
application in
the form of microgranules.
__ In the case of a post-emergence treatment of the plants, the herbicidal
mixtures or
compositions according to the invention are preferably applied by foliar
application.
Application may be effected, for example, by usual spraying techniques with
water as the
carrier, using amounts of spray mixture of approx. 20 to 1000 I/ha.
__ The required application rate of the composition of the pure active
compounds, i.e. of
herbicide A, herbicide B and optionally safener depends on the density of the
undesired
vegetation, on the development stage of the plants, on the climatic conditions
of the
location where the composition is used and on the application method. In
general, the
application rate of the composition (total amount of herbicide A, herbicide B
and optional
further actives) is from 1 to 5,000 g/ha, preferably from 5 to 1,500 g/ha of
active
substance.
The required application rates of imazethapyr are generally in the range from
1 g/ha to
Date Recue/Date Received 2021-08-10

- 23 -
200 g/ha and preferably in the range from 5 g/ha to 150 g/ha or from 10 g/ha
to 100 g/ha
of active substance.
The required application rates of imazamox are generally in the range from 1
g/ha to 200
g/ha and preferably in the range from 5 g/ha to 150 g/ha or from 10 g/ha to
100 g/ha of
active substance.
The required application rates of the herbicide B (total amount of herbicide
B) are
generally in the range from 1 g/ha to 5,000 g/ha and preferably in the range
from 5 g/ha
to 3,000 g/ha or from 10 g/ha to 1,500 g/ha of active substance.
The required application rates of the safener, if applied, are generally in
the range from 1
g/ha to 2,000 g/ha and preferably in the range from 2 g/ha to 2,000 g/ha or
from 5 g/ha
to 2,000 g/ha of active substance.
The compositions of these embodiments are particularly suitable for
controlling mono-
and dicotyledonous weeds and sedge weeds, in particular Acalypha spec.,
Physalis spec.,
Digera spec., Aegllops Cylindrica, Agropyron repens, Alopecurus myosuroides,
Avena
fatua, Brass/ca spec., Brach/aria spec., Bromus spec., Echinochloa spec. such
as for
example Echinochloa colonum, Lolium spec., Phalaris spec., red rice, Setaria
spec.,
Sorghum spec., Abuthllon theoprasti, Amarantus spec., Brass/ca kaber, Capsella
bursa-
pastor/s, Chenopodium spec., Cyperus spec., Euphorbia spec. such as for
example
Euphorbia hirta or Euphorbia geniculata, Geranium sepc., Ipomoea spec.,
Polygonum
Date Recue/Date Received 2021-08-10

- 24 -
spec., Raphanus raphanistrum, Sinapis arevensis, Sysimbrium spec., Thlaspi
arvense,
Rottboellia cochinchinensis, Dinebra spec., Digitaria sanguinalis, Eleusine
indica,
Saccharum spontaneum, Cynodon dactylon, Commelina benghalensis, Commelina
communis, Parthenium spec., Celosia argentea, Cynotis spp and Xanthium
strumarium.
The herbicidal composition comprising imazethapyr, imazamox and fomesafen is
particularly suitable for controlling Phalaris spec. such as
Phalariscanariensis,
Leptochloa spec. such as Leptochloa fusca, Ambrosia spec. such as Ambrosia
artemisiifolia, Geranium spec. such as Geranium dissectum, Sesbania spec. such
as
Sesbania exaltata, Conyza spec. such as Conyza Canadensis, convolvulus spec.
such as
Convolvulus arvensis and Polygonum spec. such as Polygonum persicaria.
The compositions of the invention are suitable for controlling weeds selected
from
Phalaris spec, Leptochloa spec, Echinochloa spec., Setaria spec., Digitaria
spec., Pan/cum
spec., Brachiaria spec. Ambrosia spec., Geranium spec. Abut//on spec.,
Sesbania spec.,
Conyza spec., Convolvulus spec. and Polygonum spec..
The compositions of the invention are particular suitable for controlling
weeds selected
from Phalarisspec, Leptochloa spec, Panicum spec., Brachiaria spec. Ambrosia
spec.,
Geranium spec. Sesbania spec., Conyza spec., Convolvulus spec. and Polygonum
spec.
The compositions of these embodiments are in particular suitable for combating
undesired vegetation in soybean, peanut, pea, bean, lentil, green gram, black
gram,
Date Recue/Date Received 2021-08-10

- 25 -
cluster bean, fenugreek, other pulse or leguminous crops, or crops which are
tolerant to
the action of acetohydroxyacid synthase inhibiting herbicides, such as for
example
Cearfied wheat, Cearfied barley, Cearfied corn, Cearfied lentil, Cearfied
oilseed rape or canola, Cearfied rice, Cutivance soybean and/or Cearfied
sunflower. The compositions of these embodiments are most suitable for
combating
undesired vegetation in soybean, peanut, pea, bean, lentil, green gram, black
gram,
cluster bean, fenugreek, other pulse or leguminous crops, preferably soybean.
If not stated otherwise, the compositions of this embodiment are suitable for
application
in any variety of the aforementioned crop plants.
In particular, the compositions of these embodiments are suitable for
application in
soybean, peanut, pea, bean, lentil, green gram, black gram, cluster bean,
fenugreek, other
pulse or leguminous crops, preferably soybean.
The present invention also relates to formulations of the compositions
according to the
present invention. The formulations contain, besides the composition, at least
one
organic or inorganic carrier material. The formulations may also contain, if
desired, one or
more surfactants and, if desired, one or more further auxiliaries customary
for crop
protection compositions.
The formulation may be in the form of a single package formulation containing
both the
herbicide A and the at least one herbicide B together with liquid and/or solid
carrier
Date Recue/Date Received 2021-08-10

- 26 -
materials, and, if desired, one or more surfactants and, if desired, one or
more further
auxiliaries customary for crop protection compositions. The formulation may be
in the
form of a two package formulation, wherein one package contains a formulation
of the
herbicide A while the other package contains a formulation of the at least one
herbicide B
and wherein both formulations contain at least one carrier material, if
desired, one or
more surfactants and, if desired, one or more further auxiliaries customary
for crop
protection compositions. In the case of two package formulations the
formulation
containing the herbicide A and the formulation containing the herbicide B are
mixed prior
to application. In case the herbicide A itself is a two package formulation
the composition
is in the form of a three-pack formulation. Preferably the mixing is performed
as a tank
mix, i.e. the formulations are mixed immediately prior or upon dilution with
water.
In the formulation of the present invention the active ingredients, i.e.
imazethapyr,
imazamox, herbicide B and optional further actives are present in suspended,
emulsified
or dissolved form. The formulation according to the invention can be in the
form of
aqueous solutions, powders, suspensions, also highly-concentrated aqueous,
oily or other
suspensions or dispersions, aqueous emulsions, aqueous microemulsions, aqueous
suspoemulsions, oil dispersions, pastes, dusts, materials for spreading or
granules.
Depending on the formulation type, they comprise one or more liquid or solid
carriers, if
appropriate surfactants (such as dispersants, protective colloids,
emulsifiers, wetting
agents and tackifiers), and if appropriate further auxiliaries which are
customary for
formulating crop protection products. The person skilled in the art is
sufficiently familiar
Date Recue/Date Received 2021-08-10

- 27 -
with the recipes for such formulations. Further auxiliaries include e.g.
organic and
inorganic thickeners, bactericides, antifreeze agents, antifoams, colorants
and, for seed
formulations, adhesives.
Suitable carriers include liquid and solid carriers. Liquid carriers include
e.g. non-aqueous
solvents such as cyclic and aromatic hydrocarbons, e.g. paraffins, tetrahydro-
naphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes
and their
derivatives, alcohols such as methanol, ethanol, propanol, butanol and
cyclohexanol,
ketones such as cyclohexanone, strongly polar solvents, e.g. amines such as N-
methylpyrrolidone, and water as well as mixtures thereof. Solid carriers
include e.g.
mineral earths such as silicas, silica gels, silicates, talc, kaolin,
limestone, lime, chalk,
bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium
sulfate,
magnesium oxide, ground synthetic materials, fertilizers such as ammonium
sulfate,
ammonium phosphate, ammonium nitrate, ureas, and products of vegetable origin
such
as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose
powders, or other
solid carriers.
Suitable surfactants (adjuvants, wetting agents, tackifiers, dispersants and
also
emulsifiers) are the alkali metal salts, alkaline earth metal salts and
ammonium salts of
aromatic sulfonic acids, for example lignosulfonic acids (e.g. BorrespersTM-
types,
Borregaard), phenolsulfonic acids, naphthalenesulfonic acids (Morwet types,
Akzo Nobel)
and dibutylnaphthalenesulfonic acid (Nekal types, BASF SE), and of fatty
acids, alkyl-
and alkylarylsulfonates, alkyl sulfates, lauryl ether sulfates and fatty
alcohol sulfates, and
Date Recue/Date Received 2021-08-10

- 28 -
salts of sulfated hexa-, hepta- and octadecanols, and also of fatty alcohol
glycol ethers,
condensates of sulfonated naphthalene and its derivatives with formaldehyde,
condensates of naphthalene or of the naphthalenesulfonic acids with phenol and
formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl-, octyl-
or
nonylphenol, alkylphenyl or tributylphenyl polyglycol ether, alkylaryl
polyether alcohols,
isotridecyl alcohol, fatty alcohol/ethylene oxide condensates, ethoxylated
castor oil,
polyoxyethylene alkyl ethers or polyoxypropylene alkyl ethers, lauryl alcohol
polyglycol
ether acetate, sorbitol esters, lignosulfite waste liquors and proteins,
denaturated
proteins, polysaccharides (e.g. methylcellulose), hydrophobically modified
starches,
.. polyvinyl alcohol (Mowio types Clariant), polycarboxylates (BASF SE,
Sokaan types),
polyalkoxylates, polyvinylamine (BASF SE, Lupamine types), polyethyleneimine
(BASF
SE, Lupaso types), polyvinylpyrrolidone and copolymers thereof.
Examples of thickeners (i.e. compounds which impart to the formulation
modified flow
properties, i.e. high viscosity in the state of rest and low viscosity in
motion) are
polysaccharides, such as xanthan gum (Kezan from Kelco), Rhodopo 23 (Rhone
Poulenc) or Veegum (from R.T. Vanderbilt), and also organic and inorganic
sheet
minerals, such as Attacay (from Engelhardt).
Examples of antifoams are silicone emulsions (such as, for example, SHikon
SRE,
Wacker or RhodorsH from Rhodia), long-chain alcohols, fatty acids, salts of
fatty acids,
organofluorine compounds and mixtures thereof.
Date Recue/Date Received 2021-08-10

- 29 -
Bactericides can be added for stabilizing the aqueous herbicidal formulations.
Examples
of bactericides are bactericides based on diclorophen and benzyl alcohol
hemiformal
(Proxe from ICI or Acticide RS from Thor Chemie and Kathon MK from Rohm &
Haas), and also isothiazolinone derivates, such as alkylisothiazolinones and
benzisothiazolinones (Acticide MBS from Thor Chemie).
Examples of antifreeze agents are ethylene glycol, propylene glycol, urea or
glycerol.
Examples of colorants are both sparingly water-soluble pigments and water-
soluble dyes.
Examples which may be mentioned are the dyes known under the names Rhodamin B,
C.I. Pigment Red 112 and C.I. Solvent Red 1, and also pigment blue 15:4,
pigment blue
15:3, pigment blue 15:2, pigment blue 15:1, pigment blue 80, pigment yellow 1,
pigment
yellow 13, pigment red 112, pigment red 48:2, pigment red 48:1, pigment red
57:1,
pigment red 53:1, pigment orange 43, pigment orange 34, pigment orange 5,
pigment
green 36, pigment green 7, pigment white 6, pigment brown 25, basic violet 10,
basic
violet 49, acid red 51, acid red 52, acid red 14, acid blue 9, acid yellow 23,
basic red 10,
basic red 108.
Examples of adhesives are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl
alcohol and
tylose.
To prepare emulsions, pastes or oil dispersions, the active the components, as
such or
dissolved in an oil or solvent, can be homogenized in water by means of
wetting agent,
Date Recue/Date Received 2021-08-10

- 30 -
tackifier, dispersant or emulsifier. Alternatively, it is possible to prepare
concentrates
consisting of active substance, wetting agent, tackifier, dispersant or
emulsifier and, if
desired, solvent or oil, and these concentrates are suitable for dilution with
water.
Powders, materials for spreading and dusts can be prepared by mixing or
concomitant
grinding of the active the components a) and b) and optionally safener c) with
a solid
carrier.
Granules, e.g. coated granules, impregnated granules and homogeneous granules,
can be
prepared by binding the active ingredients to solid carriers.
The formulations of the invention comprise a herbicidally effective amount of
the
composition of the present invention. The concentrations of the active the
active
ingredients in the formulations can be varied within wide ranges. In general,
the
formulations comprise from 1 to 98% by weight, preferably 10 to 60 % by
weight, of active
ingredients (sum of imazethapyr, imazamox, herbicide B and optionally further
acitves).
The active ingredients are employed in a purity of from 90% to 100%,
preferably 95% to
100% (according to NMR spectrum).
The active compounds A and B as well as the compositions according to the
invention
can, for example, be formulated as follows:
1. Products for dilution with water
Date Recue/Date Received 2021-08-10

- 31 -
A Water-soluble concentrates
parts by weight of active compound (or composition) are dissolved in 90 parts
by
weight of water or a water-soluble solvent. As an alternative, wetters or
other adjuvants
5 are added. The active compound dissolves upon dilution with water. This
gives a
formulation with an active compound content of 10% by weight.
Dispersible concentrates
parts by weight of active compound (or composition) are dissolved in 70 parts
by
10 weight of cyclohexanone with addition of 10 parts by weight of a
dispersant, for example
polyvinylpyrrolidone. Dilution with water gives a dispersion. The active
compound content
is 20% by weight.
Emulsifiable concentrates
15 15 parts by weight of active compound (or composition) are dissolved in
75 parts by
weight of an organic solvent (eg. alkylaromatics) with addition of calcium
dodecyl-
benzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight).
Dilution with
water gives an emulsion. The formulation has an active compound content of 15%
by
weight.
Emulsions
parts by weight of active compound (or composition) are dissolved in 35 parts
by
weight of an organic solvent (eg. alkylaromatics) with addition of calcium
dodecyl-
Date Recue/Date Received 2021-08-10

- 32 -
benzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight).
This mixture
is introduced into 30 parts by weight of water by means of an emulsifier
(Ultraturrax) and
made into a homogeneous emulsion. Dilution with water gives an emulsion. The
formulation has an active compound content of 25% by weight.
E Suspensions
In an agitated ball mill, 20 parts by weight of active compound (or
composition) are
comminuted with addition of 10 parts by weight of dispersants and wetters and
70 parts
by weight of water or an organic solvent to give a fine active compound
suspension.
Dilution with water gives a stable suspension of the active compound. The
active
compound content in the formulation is 20% by weight.
F Water-dispersible granules and water-soluble granules
50 parts by weight of active compound (or composition) are ground finely with
addition of
50 parts by weight of dispersants and wetters and made into water-dispersible
or water-
soluble granules by means of technical appliances (for example extrusion,
spray tower,
fluidized bed). Dilution with water gives a stable dispersion or solution of
the active
compound. The formulation has an active compound content of 50% by weight.
G Water-dispersible powders and water-soluble powders
75 parts by weight of active compound (or composition) are ground in a rotor-
stator mill
with addition of 25 parts by weight of dispersants, wetters and silica gel.
Dilution with
water gives a stable dispersion or solution of the active compound. The active
compound
Date Recue/Date Received 2021-08-10

- 33 -
content of the formulation is 75% by weight.
H Gel formulations
In a ball mill, 20 parts by weight of active compound (or composition), 10
parts by weight
of dispersant, 1 part by weight of gelling agent and 70 parts by weight of
water or of an
organic solvent are mixed to give a fine suspension. Dilution with water gives
a stable
suspension with active compound content of 20% by weight.
2. Products to be applied undiluted
I Dusts
5 parts by weight of active compound (or composition) are ground finely and
mixed
intimately with 95 parts by weight of finely divided kaolin. This gives a
dusting powder
with an active compound content of 5% by weight.
J Granules (GR, FG, GG, MG)
0.5 parts by weight of active compound (or composition) are ground finely and
associated
with 99.5 parts by weight of carriers. Current methods here are extrusion,
spray-drying or
the fluidized bed. This gives granules to be applied undiluted with an active
compound
content of 0.5% by weight.
K ULV solutions (UL)
10 parts by weight of active compound (or composition) are dissolved in 90
parts by
Date Recue/Date Received 2021-08-10

- 34 -
weight of an organic solvent, for example xylene. This gives a product to be
applied
undiluted with an active compound content of 10% by weight.
Aqueous use forms can be prepared from emulsion concentrates, suspensions,
pastes,
wettable powders or water-dispersible granules by adding water.
It may furthermore be beneficial to apply the compositions of the invention
alone or in
combination with other herbicides, or else in the form of a mixture with other
crop
protection agents, for example together with agents for controlling pests or
phytopathogenic fungi or bacteria. Also of interest is the miscibility with
mineral salt
solutions, which are employed for treating nutritional and trace element
deficiencies.
Other additives such as non-phytotoxic oils and oil concentrates may also be
added.
Synergism can be described as an interaction where the combined effect of two
or more
.. compounds is greater than the sum of the individual effects of each of the
compounds.
The presence of a synergistic effect in terms of percent control, between two
mixing
partners (X and Y) can be calculated using the Colby equation (Colby, S. R.,
1967,
Calculating Synergistic and Antagonistic Responses in Herbicide Combinations,
Weeds,
15, 21-22):
T7 XY
100
When the observed combined control effect is greater than the expected
(calculated)
Date Recue/Date Received 2021-08-10

- 35 -
combined control effect (E), then the combined effect is synergistic. The
synergictic
effect may also be present when the observed combined control effect is equal
to the
expected (calculates) combined control effect, especially when control values
over 90 are
calculated.
The following tests demonstrate the control efficacy of compounds, mixtures or
compositions of this invention on specific weeds. However, the weed control
afforded by
the compounds, mixtures or compositions is not limited to these species.The
analysis of
synergism or antagonism between the mixtures or compositions was determined
using
Colby's equation.
Analogously, the Colby's equation can be used to determine synergism of 3-way
and
higher mixtures:
XYZ + (X2) 1- (72)
E = X 1-17 f Z _________________________
10000 I 100
Examples
Products:
Imazethapyr ¨ 70 % WG
Imazamox ¨ 70 % WG
(Imazethapyr 35 + Imazamox 35) ¨70 % WG
Bentazon -480 g /Ht SC
Fomesafen - 240 g/lit SC
Sulfentrazone - 480 g/lit SC
Date Recue/Date Received 2021-08-10

- 36 -
Weeds in the study
EPPO Code Scientific Name
PHACA Phalaris canariensis
LEFFA Leptochloa fusca
AMBEL Ambrosia artemisiifolia
GERDI Geranium dissectum
ABUTH Abutilon theophrasti
ECHCG Echinochloa crus-galli
SETFA Setaria faberi
DIGSA Digitaria sanguinalis
SEBEX Sesbania exaltata
ERICA Conyza canadensis
CONAR Convolvulus arvensis
POLPE Polygonum persicaria
PANMI Panicum miliaceum
BRADC Brachiaria decumbens
Example 1: Post emergence treatment by the mixture of (Imazamox+Imazethapyr) +
Bentazon
Herbicidal activity against
Application rate in g ai/ha
PHACA LEFFA AMBEL GERD! ABUTH
Calcu Calcu Calcu Calcu Calcu
Imazethapyr Imazamox Bentazon Found Found Found Found Found
lated lated lated lated lated
15 -- -- 30 -- 45 -- 98 -- 65 -- 50
--
15 65 -- 85 98 -- 80 95 --
Date Recue/Date Received 2021-08-10

- 37 -
25 0 0 0 -- 0 0
(15+15) 25 85 76 98 92 100 100 98 93 98 98
Herbicidal activity against
Application rate in g ai/ha
ECHCG SETFA DIGSA SEBEX ERICA
Calcu Calcu Calcu Calcu Calcu
Imazethapyr Imazamox Bentazon Found Found Found Found Found
lated lated lated lated lated
15 -- -- 80 -- 90 -- 80 -- 0 --
55 --
-- 15 -- 98 -- 98 -- 98 -- 45 --
60 --
-- -- 50 35 -- 10 -- 40 -- 40 --
40 --
(15+15) 50 100 100 100 100 100 100 75 67 100 89
Example 2: Post emergence treatment by the mixture of (Imazamox+Imazethapyr) +
Fomesafen
Herbicidal activity against
Application rate in g ai/ha
PHACA LEFFA GERD! CONAR POLPE
Calcu Calcu Calcu Calcu Calcu
Imazethapyr Imazamox Fomesafen Found Found Found Found Found
lated lated lated lated lated
15 -- -- 30 -- 45 -- 65 -- 65 -- 0
--
-- 15 -- 65 -- 85 -- 80 -- 75 -- 95
--
-- -- 6 0 -- 0 -- 0 -- 0 -- 20 -
-
(15+15) 6 90 76 98 92 100 93 95 91 98 96
Herbicidal activity against
Application rate in g ai/ha
SEBEX ERICA GERD! AMBEL
Calcu Calcu Calcu Calcu
Imazethapyr Imazamox Fomesafen Found Found Found Found
lated lated lated lated
-- -- 0 -- 55 -- 65 -- 65 --
15 45 -- 60 -- 95 -- 70 --
Date Recue/Date Received 2021-08-10

- 38 -
80 -- 30 -- 70 -- 65 --
(15+15) 10 100 89 100 87
100 99 100 96
Example 3: Post emergence treatment by the mixture of (Imazamox+Imazethapyr) +
Sulfentrazone
Herbicidal activity against
Application rate in g ai/ha
PHACA SETFA PANMI LEFFA GERD!
Calcu Calcu Calcu Calcu Calcu
Imazethapyr Imazamox Sulfentrazone Found Found Found Found
Found
lated lated lated lated lated
30 -- 95 70 -- 45 -- 65 --
-- 15 -- 65 -- 98 -- 98 -- 85 --
80 --
-- -- 6 0 -- 0 -- 0 -- 0 -- 0
--
(15+15) 6 85 76 100 100 100 99 98 92 95 93
Herbicidal activity against
Application rate in g ai/ha
BRADC SEBEX POLPE
Calcu Calcu Calcu
Imazethapyr Imazamox Sulfentrazone Found Found Found
lated lated lated
15 10 0 75 --
15 35 45 -- 95 --
-- -- 10 30 -- 80 -- 80 --
(15+15) 10 70 59 100 89 100 100
5
Date Recue/Date Received 2021-08-10

Representative Drawing

Sorry, the representative drawing for patent document number 3127303 was not found.

Administrative Status

2024-08-01:As part of the Next Generation Patents (NGP) transition, the Canadian Patents Database (CPD) now contains a more detailed Event History, which replicates the Event Log of our new back-office solution.

Please note that "Inactive:" events refers to events no longer in use in our new back-office solution.

For a clearer understanding of the status of the application/patent presented on this page, the site Disclaimer , as well as the definitions for Patent , Event History , Maintenance Fee  and Payment History  should be consulted.

Event History

Description Date
Letter Sent 2024-05-27
Notice of Allowance is Issued 2024-05-27
Inactive: Approved for allowance (AFA) 2024-05-23
Inactive: QS passed 2024-05-23
Inactive: Ack. of Reinst. (Due Care Not Required): Corr. Sent 2024-02-21
Amendment Received - Voluntary Amendment 2024-02-20
Amendment Received - Response to Examiner's Requisition 2024-02-20
Reinstatement Requirements Deemed Compliant for All Abandonment Reasons 2024-02-20
Reinstatement Request Received 2024-02-20
Deemed Abandoned - Failure to Respond to an Examiner's Requisition 2023-10-16
Examiner's Report 2023-06-15
Inactive: Q2 failed 2023-06-09
Examiner's Interview 2023-05-04
Amendment Received - Voluntary Amendment 2023-05-02
Amendment Received - Voluntary Amendment 2023-05-02
Inactive: Correspondence - Formalities 2023-02-03
Amendment Received - Response to Examiner's Requisition 2023-01-16
Amendment Received - Voluntary Amendment 2023-01-16
Examiner's Report 2022-09-29
Inactive: Report - No QC 2022-09-29
Letter sent 2022-03-04
Letter sent 2022-02-18
Common Representative Appointed 2021-11-13
Correct Applicant Request Received 2021-11-11
Inactive: Cover page published 2021-09-17
Inactive: First IPC assigned 2021-09-08
Inactive: IPC assigned 2021-09-08
Inactive: IPC assigned 2021-09-08
Inactive: IPC assigned 2021-09-08
Inactive: IPC assigned 2021-09-08
Letter sent 2021-09-08
Priority Claim Requirements Determined Compliant 2021-09-01
Letter Sent 2021-09-01
Letter Sent 2021-09-01
Divisional Requirements Determined Compliant 2021-09-01
Priority Claim Requirements Determined Compliant 2021-09-01
Request for Priority Received 2021-09-01
Request for Priority Received 2021-09-01
Inactive: QC images - Scanning 2021-08-10
Request for Examination Requirements Determined Compliant 2021-08-10
Inactive: Pre-classification 2021-08-10
All Requirements for Examination Determined Compliant 2021-08-10
Application Received - Divisional 2021-08-10
Application Received - Regular National 2021-08-10
Common Representative Appointed 2021-08-10
Application Published (Open to Public Inspection) 2015-07-16

Abandonment History

Abandonment Date Reason Reinstatement Date
2024-02-20
2023-10-16

Maintenance Fee

The last payment was received on 

Note : If the full payment has not been received on or before the date indicated, a further fee may be required which may be one of the following

  • the reinstatement fee;
  • the late payment fee; or
  • additional fee to reverse deemed expiry.

Please refer to the CIPO Patent Fees web page to see all current fee amounts.

Fee History

Fee Type Anniversary Year Due Date Paid Date
Request for examination - standard 2021-11-10 2021-08-10
Application fee - standard 2021-08-10 2021-08-10
MF (application, 6th anniv.) - standard 06 2021-08-10 2021-08-10
MF (application, 2nd anniv.) - standard 02 2021-08-10 2021-08-10
MF (application, 3rd anniv.) - standard 03 2021-08-10 2021-08-10
MF (application, 5th anniv.) - standard 05 2021-08-10 2021-08-10
Registration of a document 2021-08-10 2021-08-10
MF (application, 4th anniv.) - standard 04 2021-08-10 2021-08-10
MF (application, 7th anniv.) - standard 07 2022-01-05 2021-12-08
MF (application, 8th anniv.) - standard 08 2023-01-05 2022-12-08
MF (application, 9th anniv.) - standard 09 2024-01-05 2023-12-08
Reinstatement 2024-10-16 2024-02-20
MF (application, 10th anniv.) - standard 10 2025-01-06
Owners on Record

Note: Records showing the ownership history in alphabetical order.

Current Owners on Record
BASF AGROCHEMICAL PRODUCTS B.V.
Past Owners on Record
ABHISHEK BEOHAR
AJAY CHANDOLA
CYRILL ZAGAR
EDSON BEGLIOMINI
NILANJAN SANYAL
SATISH GANIGER
SUDHAKAR KANDRU
YOGENDRA RATHORE
YOGESH OTURKAR
Past Owners that do not appear in the "Owners on Record" listing will appear in other documentation within the application.
Documents

To view selected files, please enter reCAPTCHA code :



To view images, click a link in the Document Description column. To download the documents, select one or more checkboxes in the first column and then click the "Download Selected in PDF format (Zip Archive)" or the "Download Selected as Single PDF" button.

List of published and non-published patent-specific documents on the CPD .

If you have any difficulty accessing content, you can call the Client Service Centre at 1-866-997-1936 or send them an e-mail at CIPO Client Service Centre.


Document
Description 
Date
(yyyy-mm-dd) 
Number of pages   Size of Image (KB) 
Description 2024-02-20 40 1,885
Claims 2024-02-20 2 106
Description 2023-05-02 40 1,774
Description 2021-08-10 38 1,183
Claims 2021-08-10 3 65
Abstract 2021-08-10 1 10
Cover Page 2021-09-17 2 35
Description 2023-01-16 40 1,810
Claims 2023-01-16 2 105
Claims 2023-05-02 2 105
Confirmation of electronic submission 2024-09-24 2 62
Reinstatement / Amendment / response to report 2024-02-20 17 559
Commissioner's Notice - Application Found Allowable 2024-05-27 1 585
Courtesy - Acknowledgement of Request for Examination 2021-09-01 1 433
Courtesy - Certificate of registration (related document(s)) 2021-09-01 1 364
Courtesy - Abandonment Letter (R86(2)) 2023-12-27 1 557
Courtesy - Acknowledgment of Reinstatement (Request for Examination (Due Care not Required)) 2024-02-21 1 411
Examiner requisition 2023-06-15 3 160
PCT Correspondence 2023-02-03 6 220
New application 2021-08-10 17 647
Courtesy - Filing Certificate for a divisional patent application 2021-09-08 2 229
Modification to the applicant/inventor 2021-11-11 8 668
Courtesy - Filing Certificate for a divisional patent application 2022-02-18 2 258
Courtesy - Filing Certificate for a divisional patent application 2022-03-04 2 251
Examiner requisition 2022-09-29 4 274
Amendment / response to report 2023-01-16 18 601
Interview Record 2023-05-04 1 33
Amendment / response to report 2023-05-02 16 518