Note: Descriptions are shown in the official language in which they were submitted.
CA 02864272 2014-08-11
WO 2013/127862 PCT/EP2013/053943
Use of an agrochemical composition with herbicidal action in rapeseed
Description
The present invention relates to the use of an agrochemical composition
comprising at
least one specific herbicide and at least one specific fungicide for
controlling undesired
vegetation in rapeseed cultures and for the desiccation and/or defoliation of
rapeseed.
The invention further relates to a method for controlling undesired vegetation
in rape-
seed cultures and to a method for the desiccation and/or defoliation of
rapeseed plants.
In the case of crop protection, such as herbicidal compositions, it is
desirable in
principle to increase the specific activity of an active compound and the
reliability of the
effect. For an herbicidal composition, it is particularly desirable to control
harmful plants
effectively, but at the same time to be compatible with the useful plants in
question.
Also desirable is a broad spectrum of activity allowing the simultaneous
control of
harmful plants. Frequently, this cannot be achieved using a single active
compound.
With many highly effective herbicides, there is the problem that their
compatibility with
useful plants, in particular dicotyledonous crop plants, such as cotton,
oilseed rape and
graminaceous plants, such as barley, millet, corn, rice, wheat and sugar cane,
is not
always satisfactory, i.e. in addition to the harmful plants, the crop plants,
too, are
damaged on a scale which cannot be tolerated. By reducing the application
rates, the
useful plants are spared; however, naturally, the extent of the control of
harmful plants
decreases, too.
It is known that special combinations of different specifically active
herbicides result in
enhanced activity of a herbicide component in the sense of a synergistic
effect. In this
manner, it is possible to reduce the application rates of herbicidal active
compounds
required for controlling the harmful plants.
Furthermore, it is known that in some cases joint application of specifically
acting
herbicides with other organic active compounds allows better crop plant
compatibility to
be achieved. In these cases, the active compounds act as antidotes or
antagonists and
are also referred to as safeners, since they reduce or even prevent damage to
the crop
plants.
Rapeseed are among the most important crop plants. Improving their growth
conditions
is thus an ongoing need.
It is an object of the present invention to provide agrochemical compositions
which are
highly active against unwanted harmful plants in rapeseed cultures.
CA 02864272 2014-08-11
WO 2013/127862
PCT/EP2013/053943
2
This and further objects are achieved by the agricultural composition
described below.
Surprisingly, this composition has better herbicidal activity, i.e. a better
activity against
harmful plants, than would have been expected based on the herbicidal activity
observed for the individual compounds, or a broader activity spectrum.
Moreover, the time frame, within which the desired herbicidal action can be
achieved,
may be expanded by said composition. This allows a more flexibly timed
application of
the compositions according to the present invention in comparison with the
single
compounds.
Said composition also has a better compatibility with useful plants.
Accordingly, the present invention relates to the use of an agrochemical
composition
comprising
A) at least one herbicide A selected from
A.a) lipid synthesis inhibitors selected from clethodim (A.1), cycloxydim
(A.2),
diclofop (A.3), fenoxaprop (A.4), fenoxaprop-P (A.5), fluazifop (A.6), fluazi-
fop-P (A.7), haloxyfop (A.8), haloxyfop-P (A.9), propaquizafop (A.10),
prosulfocarb (A.11), quizalofop-ethyl (A.12), quizalofop-P (A.13), sethox-
ydim (A.14) and tepraloxydim (A.15);
A.b) acetolactate synthase inhibitors (ALS inhibitors) selected from
ethametsul-
furon (A.16), flupyrsulfuron (A.17), thifensulfuron (A.18) and tribenuron
(A.19); and
A.c) glutamine synthase (GS) inhibitors selected from glufosinate (A.20) and
glufosinate-P (A.21);
and their agriculturally acceptable salts esters and amides;
and
B) at least one fungicide B selected from
B.a) inhibitors of complex Ill at Q0 site selected from azoxystrobin (B.1),
cou-
methoxystrobin (B.2), coumoxystrobin (B.3), dimoxystrobin (B.4), enestro-
burin (B.5), famoxadone (B.6), fenaminstrobin (B.7), fenoxy-
strobin/flufenoxystrobin (B.8), fluoxastrobin (B.9), kresoxim-methyl (B.10),
metominostrobin (B.11), picoxystrobin (B.12), pyraclostrobin (B.13),
pyrametostrobin (B.14), pyraoxystrobin (B.15), trifloxystrobin (B.16), 2-[2-
(2,5-dimethylphenyl-oxymethyl)pheny1]-3-methoxy-acrylic acid methyl ester
(B.17), 2-(2-(3-(2,6-dichloropheny1)-1-methyl-allylideneaminooxymethyl)-
CA 02864272 2014-08-11
WO 2013/127862 PCT/EP2013/053943
3
phenyl)-2-methoxyimino-N-methyl-acetamide (B.18), pyribencarb (B.19)
and triclopyricarb/chlorodincarb (B.20); and
B.b) inhibitors of complex ll selected from bixafen (B.21), boscalid (B.22),
car-
boxin (B.23), fluopyram (B.24), fluxapyroxad (B.25), isopyrazam (B.26),
penflufen (B.27), penthiopyrad (B.28), sedaxane (B.29), 3-difluoromethy1-1-
methyl-1H-pyrazole-4-carboxylic acid (9-dichloromethylene-1,2,3,4-
tetrahydro-1,4-methano-naphthalen-5-y1)-amide (B.30) and difluoromethyl-
1-methyl-1H-pyrazole-4-carboxylic acid (2-(2,4-dichloro-phenyl)-2-methoxy-
1-methyl-ethyl)-amide (B.31);
for controlling undesired vegetation in rapeseed.
In the context of the present invention, the term "rapeseed" denotes both the
plant itself
as well as its harvested product, such as rapeseed grains or seeds.
The invention moreover relates to a composition as defined above or below,
compris-
ing at least one herbicide A and at least one fungicide B.
The composition according to the invention or to be used according to the
invention
may be a physical mixture of the at least one compound A and the at least one
com-
pound B. Accordingly, the invention also provides a mixture comprising at
least one
compound A and at least one compound B. However, the composition may also be
any
combination of at least one compound A with at least one compound B, it not
being
required for compounds A and B to be present together in the same formulation.
An example of a composition according to the invention or to be used according
to the
invention in which the at least one compound A and the at least one compound B
are
not present together in the same formulation is a combipack. In a combipack,
two or
more components of a combipack are packaged separately, i.e., not jointly pre-
formulated. As such, combipacks include one or more separate containers such
as
vials, cans, bottles, pouches, bags or canisters, each container containing a
separate
component for an agrochemical composition. One example is a two-component
combi-
pack. Accordingly the present invention also relates to a two-component
combipack,
comprising a first component which in turn comprises at least one compound A,
a liquid
or solid carrier and, if appropriate, at least one surfactant and/or at least
one customary
auxiliary, and a second component which in turn comprises at least one
compound B, a
liquid or solid carrier and, if appropriate, at least one surfactant and/or at
least one cus-
tomary auxiliary. More details, e.g. as to suitable liquid and solid carriers,
surfactants
and customary auxiliaries are described below.
CA 02864272 2014-08-11
WO 2013/127862 PCT/EP2013/053943
4
The invention furthermore relates to a method for controlling undesired
vegetation in
rapeseed cultures, which method comprises allowing an effective amount of an
agrochemical composition as defined above or below to act on the rapeseed
plants or
parts thereof and/or on the environment where the rapeseed cultures grow or
are to
grow. The rapeseed might be resistant to one or more herbicides or to attack
by insects
owing to genetic engineering or breeding
The invention relates moreover to the use of a composition as defined above or
below,
for the desiccation and/or defoliation of rapeseed plants, and to a method for
the
desiccation and/or defoliation of rapeseed plants, which method comprises
treating
rapeseed plants or parts thereof with an effective amount of an agrochemical
composition as defined above or below.
The methods of the invention comprise allowing an effective amount of the
composition
as defined above or below to act on rapeseed plants or parts thereof and/or
the envi-
ronment (e.g. the locus) where the rapeseed cultures grow or are to grow. The
meth-
ods of the invention include treatment of the seeds from which the rapeseed
plants are
to grow. If the rapeseed plants are not resistant against the herbicide(s)
used and/or
the herbicide(s) is/are not selective enough and/or no safener is used, it is
convenient
to avoid their direct contact with the herbicide(s) used as far as possible in
order to
avoid injury of the rapeseed plants (except, of course, for the desiccation
and/or defoli-
ation method). This can be done, for example, by treating as selectively as
possible the
undesired vegetation or the locus where this is growing or expected to grow
(this ap-
plies of course only for the herbicidal method) or by treating the locus where
the rape-
seed plant is to grow, e.g. before or during sowing or before its emergence or
before
planting, or by treating the seeds of the rapeseed plant with the composition
of the in-
vention or, if the composition is not a physical mixture of herbicide and
fungicide, with
the herbicide of the composition. In all other cases, i.e. if the rapeseed
plants are re-
sistant against the herbicide(s) used and/or the herbicide is sufficiently
selective and
does not harm (or not to an economically dissatisfactory extent) the rapeseed
plants
and/or a safener is used, any known method for broadcasting agricultural
compositions
can be used. For further details, see below.
The herbicides A and the fungicides B as well as their agrochemical action and
meth-
ods for producing them are generally known. For instance, the commercially
available
compounds can be found in "The Pesticide Manual, 15th Edition, British Crop
Protec-
tion Council (2009)" among other publications.
CA 02864272 2014-08-11
WO 2013/127862 PCT/EP2013/053943
The preferred embodiments of the invention mentioned herein below have to be
under-
stood as being preferred either independently from each other or in
combination with
one another.
5 Preferably, the at least one herbicide A is selected from clethodim,
cycloxydim, sethox-
ydim, tepraloxydim, glufosinate, glufosinate-P; and their agriculturally
acceptable salts,
esters and amides.
Among the agriculturally acceptable salts, esters and amides of the above
herbicides,
preference is given to the following compounds:
glufosinate: glufosinate-ammonium (A.22);
glufosinate-P: glufosinate-P-ammonium (A.23);
The at least one herbicide A is more preferably selected from clethodim,
cycloxydim,
sethoxydim, tepraloxydim, glufosinate, glufosinate-ammonium, glufosinate-P and
glufosinate-P-ammonium.
In a particular embodiment, the at least one herbicide A is clethodim and the
at least
one fungicide B has one of the above general or, in particular, one of the
below pre-
ferred meanings.
In another particular embodiment, the at least one herbicide A is cycloxydim
and the at
least one fungicide B has one of the above general or, in particular, one of
the below
preferred meanings.
In another particular embodiment, the at least one herbicide A is sethoxydim
and the at
least one fungicide B has one of the above general or, in particular, one of
the below
preferred meanings.
In another particular embodiment, the at least one herbicide A is tepraloxydim
and the
at least one fungicide B has one of the above general or, in particular, one
of the below
preferred meanings.
In another particular embodiment, the at least one herbicide A is glufosinate
and the at
least one fungicide B has one of the above general or, in particular, one of
the below
preferred meanings.
In another particular embodiment, the at least one herbicide A is glufosinate-
ammonium and the at least one fungicide B has one of the above general or, in
particu-
lar, one of the below preferred meanings.
CA 02864272 2014-08-11
WO 2013/127862 PCT/EP2013/053943
6
In another particular embodiment, the at least one herbicide A is glufosinate-
P and the
at least one fungicide B has one of the above general or, in particular, one
of the below
preferred meanings.
In another particular embodiment, the at least one herbicide A is glufosinate-
P-
ammonium and the at least one fungicide B has one of the above general or, in
particu-
lar, one of the below preferred meanings.
Preferably, the at least one fungicide is selected from azoxystrobin,
dimoxystrobin,
kresoxim-methyl, picoxystrobin, pyraclostrobin, bixafen, boscalid, fluopyram,
fluxapy-
roxad, isopyrazam, 3-difluoromethy1-1-methyl-1H-pyrazole-4-carboxylic acid (9-
dichloromethylene-1,2,3,4-tetrahydro-1,4-methano-naphthalen-5-yI)-amide and 3-
difluoromethy1-1-methyl-1H-pyrazole-4-carboxylic acid (2-(2,4-dichloro-phenyl)-
2-
methoxy-1-methyl-ethyl)-amide.
More preferably, the at least one fungicide is selected from azoxystrobin,
dimoxystrobin, pyraclostrobin, bixafen, boscalid, fluopyram, fluxapyroxad,
isopyrazam
and 3-difluoromethy1-1-methyl-1H-pyrazole-4-carboxylic acid (2-(2,4-dichloro-
phenyl)-2-
methoxy-1-methyl-ethyl)-amide.
In a particular embodiment, the at least one fungicide B is azoxystrobin and
the at least
one herbicide A has one of the above general or, in particular, one of the
preferred
meanings.
In another particular embodiment, the at least one fungicide B is
dimoxystrobin and the
at least one herbicide A has one of the above general or, in particular, one
of the pre-
ferred meanings.
In another particular embodiment, the at least one fungicide B is
pyraclostrobin and the
at least one herbicide A has one of the above general or, in particular, one
of the pre-
ferred meanings.
In another particular embodiment, the at least one fungicide B is bixafen and
the at
least one herbicide A has one of the above general or, in particular, one of
the pre-
ferred meanings.
In another particular embodiment, the at least one fungicide B is boscalid and
the at
least one herbicide A has one of the above general or, in particular, one of
the pre-
ferred meanings.
In another particular embodiment, the at least one fungicide B is fluopyram
and the at
least one herbicide A has one of the above general or, in particular, one of
the pre-
ferred meanings.
CA 02864272 2014-08-11
WO 2013/127862 PCT/EP2013/053943
7
In another particular embodiment, the at least one fungicide B is fluxapyroxad
and the
at least one herbicide A has one of the above general or, in particular, one
of the pre-
ferred meanings.
In another particular embodiment, the at least one fungicide B is isopyrazam
and the at
least one herbicide A has one of the above general or, in particular, one of
the pre-
ferred meanings.
In another particular embodiment, the at least one fungicide B is 3-
difluoromethy1-1-
methyl-1H-pyrazole-4-carboxylic acid (2-(2,4-dichloro-phenyl)-2-methoxy-l-
methyl-
ethyl)-amide and the at least one herbicide A has one of the above general or,
in par-
ticular, one of the preferred meanings.
In particular, the composition to be used in the uses and the methods
according to the
invention comprises
A) at least one herbicide A selected from clethodim, cycloxydim,
sethoxydim, tepra-
loxydim, glufosinate, glufosinate-ammonium, glufosinate-P, glufosinate-P-
ammonium; and other agriculturally acceptable salts, esters and amides; and
B) at least one fungicide B selected from azoxystrobin, dimoxystrobin, pyre-
clostrobin, bixafen, boscalid, fluopyram, fluxapyroxad, isopyrazam and 3-
d ifluoromethy1-1-methyl-1H-pyrazole-4-carboxylic acid (2-(2,4-d ichloro-
phenyl)-2-
methoxy-1-methyl-ethyl)-amide.
According to a preferred embodiment of the invention, the composition
comprises as
component A at least one, preferably exactly one, herbicide A.
According to another preferred embodiment of the invention, the composition
compris-
es as component A at least two, preferably exactly two, herbicides A different
from
each other.
According to another preferred embodiment of the invention, the composition
compris-
es as component A at least three, preferably exactly three, herbicides A
different from
each other.
According to another preferred embodiment of the invention, the composition
compris-
es as component B at least one, preferably exactly one, fungicide B.
According to another preferred embodiment of the invention, the composition
compris-
es as component B at least two, preferably exactly two, fungicides B different
from
each other.
According to another preferred embodiment of the invention, the composition
compris-
es as component A at least one, preferably exactly one, herbicide A, and at
least one,
preferably exactly one, fungicide B.
CA 02864272 2014-08-11
WO 2013/127862
PCT/EP2013/053943
8
According to another preferred embodiment of the invention, the composition
compris-
es as component A at least two, preferably exactly two, herbicides A different
from
each other, and at least one, preferably exactly one, fungicide B.
According to another preferred embodiment of the invention, the composition
compris-
es as component A at least three, preferably exactly three, herbicides A
different from
each other, and at least one, preferably exactly one, fungicide B.
According to another preferred embodiment of the invention, the composition
compris-
es as only active components at least one, preferably exactly one, herbicide
A, and at
least one, preferably exactly one, fungicide B.
Particularly preferred are the compositions 1.1 to 1.713, comprising at least
one herbi-
cide A and at least one fungicide B, preferably comprising the herbicide A and
the fun-
gicide B, as defined in the respective row of table 1. The compound numbers
(A.x for
herbicide A; B.x for fungicide B) correspond to the compound numbers given
above in
the list of herbicides A and fungicides B to be used according to the present
invention.
Table 1 (compositions 1.1. to 1.713)
No herb. fung. No herb. fung. No herb. fung.
A B A B A B
1.1 A.1 B.1 1.20 A.1 B.20 1.39 A.2 B.8
1.2 A.1 B.2 1.21 A.1 B.21 1.40 A.2 B.9
1.3 A.1 B.3 1.22 A.1 B.22 1.41 A.2 B.10
1.4 A.1 B.4 1.23 A.1 B.23 1.42 A.2 B.11
1.5 A.1 B.5 1.24 A.1 B.24 1.43 A.2 B.12
1.6 A.1 B.6 1.25 A.1 B.25 1.44 A.2 B.13
1.7 A.1 B.7 1.26 A.1 B.26 1.45 A.2 B.14
1.8 A.1 B.8 1.27 A.1 B.27 1.46 A.2 B.15
1.9 A.1 B.9 1.28 A.1 B.28 1.47 A.2 B.16
1.10 A.1 B.10 1.29 A.1 B.29 1.48 A.2 B.17
1.11 A.1 B.11 1.30 A.1 B.30 1.49 A.2 B.18
1.12 A.1 B.12 1.31 A.1 B.31 1.50 A.2 B.19
1.13 A.1 B.13 1.32 A.2 B.1 1.51 A.2 B.20
1.14 A.1 B.14 1.33 A.2 B.2 1.52 A.2 B.21
1.15 A.1 B.15 1.34 A.2 B.3 1.53 A.2 B.22
1.16 A.1 B.16 1.35 A.2 B.4 1.54 A.2 B.23
1.17 A.1 B.17 1.36 A.2 B.5 1.55 A.2 B.24
1.18 A.1 B.18 1.37 A.2 B.6 1.56 A.2 B.25
1.19 A.1 B.19 1.38 A.2 B.7 1.57 A.2 B.26
CA 02864272 2014-08-11
WO 2013/127862
PCT/EP2013/053943
9
No herb. fung. No herb. fung. No herb. fung.
A B A B A B
1.58 A.2 B.27 1.96 A.4 B.3 1.134 A.5 B.10
1.59 A.2 B.28 1.97 A.4 B.4 1.135 A.5 B.11
1.60 A.2 B.29 1.98 A.4 B.5 1.136 A.5 B.12
1.61 A.2 B.30 1.99 A.4 B.6 1.137 A.5 B.13
1.62 A.2 B.31 1.100 A.4 B.7 1.138 A.5 B.14
1.63 A.3 B.1 1.101 A.4 B.8 1.139 A.5 B.15
1.64 A.3 B.2 1.102 A.4 B.9 1.140 A.5 B.16
1.65 A.3 B.3 1.103 A.4 B.10 1.141 A.5 B.17
1.66 A.3 B.4 1.104 A.4 B.11 1.142 A.5 B.18
1.67 A.3 B.5 1.105 A.4 B.12 1.143 A.5 B.19
1.68 A.3 B.6 1.106 A.4 B.13 1.144 A.5 B.20
1.69 A.3 B.7 1.107 A.4 B.14 1.145 A.5 B.21
1.70 A.3 B.8 1.108 A.4 B.15 1.146 A.5 B.22
1.71 A.3 B.9 1.109 A.4 B.16 1.147 A.5 B.23
1.72 A.3 B.10 1.110 A.4 B.17 1.148 A.5 B.24
1.73 A.3 B.11 1.111 A.4 B.18 1.149 A.5 B.25
1.74 A.3 B.12 1.112 A.4 B.19 1.150 A.5 B.26
1.75 A.3 B.13 1.113 A.4 B.20 1.151 A.5 B.27
1.76 A.3 B.14 1.114 A.4 B.21 1.152 A.5 B.28
1.77 A.3 B.15 1.115 A.4 B.22 1.153 A.5 B.29
1.78 A.3 B.16 1.116 A.4 B.23 1.154 A.5 B.30
1.79 A.3 B.17 1.117 A.4 B.24 1.155 A.5 B.31
1.80 A.3 B.18 1.118 A.4 B.25 1.156 A.6 B.1
1.81 A.3 B.19 1.119 A.4 B.26 1.157 A.6 B.2
1.82 A.3 B.20 1.120 A.4 B.27 1.158 A.6 B.3
1.83 A.3 B.21 1.121 A.4 B.28 1.159 A.6 B.4
1.84 A.3 B.22 1.122 A.4 B.29 1.160 A.6 B.5
1.85 A.3 B.23 1.123 A.4 B.30 1.161 A.6 B.6
1.86 A.3 B.24 1.124 A.4 B.31 1.162 A.6 B.7
1.87 A.3 B.25 1.125 A.5 B.1 1.163 A.6 B.8
1.88 A.3 B.26 1.126 A.5 B.2 1.164 A.6 B.9
1.89 A.3 B.27 1.127 A.5 B.3 1.165 A.6 B.10
1.90 A.3 B.28 1.128 A.5 B.4 1.166 A.6 B.11
1.91 A.3 B.29 1.129 A.5 B.5 1.167 A.6 B.12
1.92 A.3 B.30 1.130 A.5 B.6 1.168 A.6 B.13
1.93 A.3 B.31 1.131 A.5 B.7 1.169 A.6 B.14
1.94 A.4 B.1 1.132 A.5 B.8 1.170 A.6 B.15
1.95 A.4 B.2 1.133 A.5 B.9 1.171 A.6 B.16
CA 02864272 2014-08-11
WO 2013/127862
PCT/EP2013/053943
No herb. fung. No herb. fung. No
herb. fung.
A B A B A B
1.172 A.6 B.17 1.210 A.7 B.24 1.248 A.8 B.31
1.173 A.6 B.18 1.211 A.7 B.25 1.249 A.9 B.1
1.174 A.6 B.19 1.212 A.7 B.26 1.250 A.9 B.2
1.175 A.6 B.20 1.213 A.7 B.27 1.251 A.9 B.3
1.176 A.6 B.21 1.214 A.7 B.28 1.252 A.9 B.4
1.177 A.6 B.22 1.215 A.7 B.29 1.253 A.9 B.5
1.178 A.6 B.23 1.216 A.7 B.30 1.254 A.9 B.6
1.179 A.6 B.24 1.217 A.7 B.31 1.255 A.9 B.7
1.180 A.6 B.25 1.218 A.8 B.1 1.256 A.9 B.8
1.181 A.6 B.26 1.219 A.8 B.2 1.257 A.9 B.9
1.182 A.6 B.27 1.220 A.8 B.3 1.258 A.9 B.10
1.183 A.6 B.28 1.221 A.8 B.4 1.259 A.9 B.11
1.184 A.6 B.29 1.222 A.8 B.5 1.260 A.9 B.12
1.185 A.6 B.30 1.223 A.8 B.6 1.261 A.9 B.13
1.186 A.6 B.31 1.224 A.8 B.7 1.262 A.9 B.14
1.187 A.7 B.1 1.225 A.8 B.8 1.263 A.9 B.15
1.188 A.7 B.2 1.226 A.8 B.9 1.264 A.9 B.16
1.189 A.7 B.3 1.227 A.8 B.10 1.265 A.9 B.17
1.190 A.7 B.4 1.228 A.8 B.11 1.266 A.9 B.18
1.191 A.7 B.5 1.229 A.8 B.12 1.267 A.9 B.19
1.192 A.7 B.6 1.230 A.8 B.13 1.268 A.9 B.20
1.193 A.7 B.7 1.231 A.8 B.14 1.269 A.9 B.21
1.194 A.7 B.8 1.232 A.8 B.15 1.270 A.9 B.22
1.195 A.7 B.9 1.233 A.8 B.16 1.271 A.9 B.23
1.196 A.7 B.10 1.234 A.8 B.17 1.272 A.9 B.24
1.197 A.7 B.11 1.235 A.8 B.18 1.273 A.9 B.25
1.198 A.7 B.12 1.236 A.8 B.19 1.274 A.9 B.26
1.199 A.7 B.13 1.237 A.8 B.20 1.275 A.9 B.27
1.200 A.7 B.14 1.238 A.8 B.21 1.276 A.9 B.28
1.201 A.7 B.15 1.239 A.8 B.22 1.277 A.9 B.29
1.202 A.7 B.16 1.240 A.8 B.23 1.278 A.9 B.30
1.203 A.7 B.17 1.241 A.8 B.24 1.279 A.9 B.31
1.204 A.7 B.18 1.242 A.8 B.25 1.280 A.10 B.1
1.205 A.7 B.19 1.243 A.8 B.26 1.281 A.10 B.2
1.206 A.7 B.20 1.244 A.8 B.27 1.282 A.10 B.3
1.207 A.7 B.21 1.245 A.8 B.28 1.283 A.10 B.4
1.208 A.7 B.22 1.246 A.8 B.29 1.284 A.10 B.5
1.209 A.7 B.23 1.247 A.8 B.30 1.285 A.10 B.6
CA 02864272 2014-08-11
WO 2013/127862
PCT/EP2013/053943
11
No herb. fung. No herb. fung. No herb. fung.
A B A B A B
1.286 A.10 B.7 1.324 A.11 B.14 1.362 A.12 B.21
1.287 A.10 B.8 1.325 A.11 B.15 1.363 A.12 B.22
1.288 A.10 B.9 1.326 A.11 B.16 1.364 A.12 B.23
1.289 A.10 B.10 1.327 A.11 B.17 1.365 A.12 B.24
1.290 A.10 B.11 1.328 A.11 B.18 1.366 A.12 B.25
1.291 A.10 B.12 1.329 A.11 B.19 1.367 A.12 B.26
1.292 A.10 B.13 1.330 A.11 B.20 1.368 A.12 B.27
1.293 A.10 B.14 1.331 A.11 B.21 1.369 A.12 B.28
1.294 A.10 B.15 1.332 A.11 B.22 1.370 A.12 B.29
1.295 A.10 B.16 1.333 A.11 B.23 1.371 A.12 B.30
1.296 A.10 B.17 1.334 A.11 B.24 1.372 A.12 B.31
1.297 A.10 B.18 1.335 A.11 B.25 1.373 A.13 B.1
1.298 A.10 B.19 1.336 A.11 B.26 1.374 A.13 B.2
1.299 A.10 B.20 1.337 A.11 B.27 1.375 A.13 B.3
1.300 A.10 B.21 1.338 A.11 B.28 1.376 A.13 B.4
1.301 A.10 B.22 1.339 A.11 B.29 1.377 A.13 B.5
1.302 A.10 B.23 1.340 A.11 B.30 1.378 A.13 B.6
1.303 A.10 B.24 1.341 A.11 B.31 1.379 A.13 B.7
1.304 A.10 B.25 1.342 A.12 B.1 1.380 A.13 B.8
1.305 A.10 B.26 1.343 A.12 B.2 1.381 A.13 B.9
1.306 A.10 B.27 1.344 A.12 B.3 1.382 A.13 B.10
1.307 A.10 B.28 1.345 A.12 B.4 1.383 A.13 B.11
1.308 A.10 B.29 1.346 A.12 B.5 1.384 A.13 B.12
1.309 A.10 B.30 1.347 A.12 B.6 1.385 A.13 B.13
1.310 A.10 B.31 1.348 A.12 B.7 1.386 A.13 B.14
1.311 A.11 B.1 1.349 A.12 B.8 1.387 A.13 B.15
1.312 A.11 B.2 1.350 A.12 B.9 1.388 A.13 B.16
1.313 A.11 B.3 1.351 A.12 B.10 1.389 A.13 B.17
1.314 A.11 B.4 1.352 A.12 B.11 1.390 A.13 B.18
1.315 A.11 B.5 1.353 A.12 B.12 1.391 A.13 B.19
1.316 A.11 B.6 1.354 A.12 B.13 1.392 A.13 B.20
1.317 A.11 B.7 1.355 A.12 B.14 1.393 A.13 B.21
1.318 A.11 B.8 1.356 A.12 B.15 1.394 A.13 B.22
1.319 A.11 B.9 1.357 A.12 B.16 1.395 A.13 B.23
1.320 A.11 B.10 1.358 A.12 B.17 1.396 A.13 B.24
1.321 A.11 B.11 1.359 A.12 B.18 1.397 A.13 B.25
1.322 A.11 B.12 1.360 A.12 B.19 1.398 A.13 B.26
1.323 A.11 B.13 1.361 A.12 B.20 1.399 A.13 B.27
CA 02864272 2014-08-11
WO 2013/127862
PCT/EP2013/053943
12
No herb. fung. No herb. fung. No herb. fung.
A B A B A B
1.400 A.13 B.28 1.438 A.15 B.4 1.476 A.16 B.11
1.401 A.13 B.29 1.439 A.15 B.5 1.477 A.16 B.12
1.402 A.13 B.30 1.440 A.15 B.6 1.478 A.16 B.13
1.403 A.13 B.31 1.441 A.15 B.7 1.479 A.16 B.14
1.404 A.14 B.1 1.442 A.15 B.8 1.480 A.16 B.15
1.405 A.14 B.2 1.443 A.15 B.9 1.481 A.16 B.16
1.406 A.14 B.3 1.444 A.15 B.10 1.482 A.16 B.17
1.407 A.14 B.4 1.445 A.15 B.11 1.483 A.16 B.18
1.408 A.14 B.5 1.446 A.15 B.12 1.484 A.16 B.19
1.409 A.14 B.6 1.447 A.15 B.13 1.485 A.16 B.20
1.410 A.14 B.7 1.448 A.15 B.14 1.486 A.16 B.21
1.411 A.14 B.8 1.449 A.15 B.15 1.487 A.16 B.22
1.412 A.14 B.9 1.450 A.15 B.16 1.488 A.16 B.23
1.413 A.14 B.10 1.451 A.15 B.17 1.489 A.16 B.24
1.414 A.14 B.11 1.452 A.15 B.18 1.490 A.16 B.25
1.415 A.14 B.12 1.453 A.15 B.19 1.491 A.16 B.26
1.416 A.14 B.13 1.454 A.15 B.20 1.492 A.16 B.27
1.417 A.14 B.14 1.455 A.15 B.21 1.493 A.16 B.28
1.418 A.14 B.15 1.456 A.15 B.22 1.494 A.16 B.29
1.419 A.14 B.16 1.457 A.15 B.23 1.495 A.16 B.30
1.420 A.14 B.17 1.458 A.15 B.24 1.496 A.16 B.31
1.421 A.14 B.18 1.459 A.15 B.25 1.497 A.17 B.1
1.422 A.14 B.19 1.460 A.15 B.26 1.498 A.17 B.2
1.423 A.14 B.20 1.461 A.15 B.27 1.499 A.17 B.3
1.424 A.14 B.21 1.462 A.15 B.28 1.500 A.17 B.4
1.425 A.14 B.22 1.463 A.15 B.29 1.501 A.17 B.5
1.426 A.14 B.23 1.464 A.15 B.30 1.502 A.17 B.6
1.427 A.14 B.24 1.465 A.15 B.31 1.503 A.17 B.7
1.428 A.14 B.25 1.466 A.16 B.1 1.504 A.17 B.8
1.429 A.14 B.26 1.467 A.16 B.2 1.505 A.17 B.9
1.430 A.14 B.27 1.468 A.16 B.3 1.506 A.17 B.10
1.431 A.14 B.28 1.469 A.16 B.4 1.507 A.17 B.11
1.432 A.14 B.29 1.470 A.16 B.5 1.508 A.17 B.12
1.433 A.14 B.30 1.471 A.16 B.6 1.509 A.17 B.13
1.434 A.14 B.31 1.472 A.16 B.7 1.510 A.17 B.14
1.435 A.15 B.1 1.473 A.16 B.8 1.511 A.17 B.15
1.436 A.15 B.2 1.474 A.16 B.9 1.512 A.17 B.16
1.437 A.15 B.3 1.475 A.16 B.10 1.513 A.17 B.17
CA 02864272 2014-08-11
WO 2013/127862
PCT/EP2013/053943
13
No herb. fung. No herb. fung. No herb. fung.
A B A B A B
1.514 A.17 B.18 1.552 A.18 B.25 1.590 A.20 B.1
1.515 A.17 B.19 1.553 A.18 B.26 1.591 A.20 B.2
1.516 A.17 B.20 1.554 A.18 B.27 1.592 A.20 B.3
1.517 A.17 B.21 1.555 A.18 B.28 1.593 A.20 B.4
1.518 A.17 B.22 1.556 A.18 B.29 1.594 A.20 B.5
1.519 A.17 B.23 1.557 A.18 B.30 1.595 A.20 B.6
1.520 A.17 B.24 1.558 A.18 B.31 1.596 A.20 B.7
1.521 A.17 B.25 1.559 A.19 B.1 1.597 A.20 B.8
1.522 A.17 B.26 1.560 A.19 B.2 1.598 A.20 B.9
1.523 A.17 B.27 1.561 A.19 B.3 1.599 A.20 B.10
1.524 A.17 B.28 1.562 A.19 B.4 1.600 A.20 B.11
1.525 A.17 B.29 1.563 A.19 B.5 1.601 A.20 B.12
1.526 A.17 B.30 1.564 A.19 B.6 1.602 A.20 B.13
1.527 A.17 B.31 1.565 A.19 B.7 1.603 A.20 B.14
1.528 A.18 B.1 1.566 A.19 B.8 1.604 A.20 B.15
1.529 A.18 B.2 1.567 A.19 B.9 1.605 A.20 B.16
1.530 A.18 B.3 1.568 A.19 B.10 1.606 A.20 B.17
1.531 A.18 B.4 1.569 A.19 B.11 1.607 A.20 B.18
1.532 A.18 B.5 1.570 A.19 B.12 1.608 A.20 B.19
1.533 A.18 B.6 1.571 A.19 B.13 1.609 A.20 B.20
1.534 A.18 B.7 1.572 A.19 B.14 1.610 A.20 B.21
1.535 A.18 B.8 1.573 A.19 B.15 1.611 A.20 B.22
1.536 A.18 B.9 1.574 A.19 B.16 1.612 A.20 B.23
1.537 A.18 B.10 1.575 A.19 B.17 1.613 A.20 B.24
1.538 A.18 B.11 1.576 A.19 B.18 1.614 A.20 B.25
1.539 A.18 B.12 1.577 A.19 B.19 1.615 A.20 B.26
1.540 A.18 B.13 1.578 A.19 B.20 1.616 A.20 B.27
1.541 A.18 B.14 1.579 A.19 B.21 1.617 A.20 B.28
1.542 A.18 B.15 1.580 A.19 B.22 1.618 A.20 B.29
1.543 A.18 B.16 1.581 A.19 B.23 1.619 A.20 B.30
1.544 A.18 B.17 1.582 A.19 B.24 1.620 A.20 B.31
1.545 A.18 B.18 1.583 A.19 B.25 1.621 A.21 B.1
1.546 A.18 B.19 1.584 A.19 B.26 1.622 A.21 B.2
1.547 A.18 B.20 1.585 A.19 B.27 1.623 A.21 B.3
1.548 A.18 B.21 1.586 A.19 B.28 1.624 A.21 B.4
1.549 A.18 B.22 1.587 A.19 B.29 1.625 A.21 B.5
1.550 A.18 B.23 1.588 A.19 B.30 1.626 A.21 B.6
1.551 A.18 B.24 1.589 A.19 B.31 1.627 A.21 B.7
CA 02864272 2014-08-11
WO 2013/127862
PCT/EP2013/053943
14
No herb. fung. No herb. fung. No herb. fung.
A B A B A B
1.628 A.21 B.8 1.657 A.22 B.6 1.686 A.23 B.4
1.629 A.21 B.9 1.658 A.22 B.7 1.687 A.23 B.5
1.630 A.21 B.10 1.659 A.22 B.8 1.688 A.23 B.6
1.631 A.21 B.11 1.660 A.22 B.9 1.689 A.23 B.7
1.632 A.21 B.12 1.661 A.22 B.10 1.690 A.23 B.8
1.633 A.21 B.13 1.662 A.22 B.11 1.691 A.23 B.9
1.634 A.21 B.14 1.663 A.22 B.12 1.692 A.23 B.10
1.635 A.21 B.15 1.664 A.22 B.13 1.693 A.23 B.11
1.636 A.21 B.16 1.665 A.22 B.14 1.694 A.23 B.12
1.637 A.21 B.17 1.666 A.22 B.15 1.695 A.23 B.13
1.638 A.21 B.18 1.667 A.22 B.16 1.696 A.23 B.14
1.639 A.21 B.19 1.668 A.22 B.17 1.697 A.23 B.15
1.640 A.21 B.20 1.669 A.22 B.18 1.698 A.23 B.16
1.641 A.21 B.21 1.670 A.22 B.19 1.699 A.23 B.17
1.642 A.21 B.22 1.671 A.22 B.20 1.700 A.23 B.18
1.643 A.21 B.23 1.672 A.22 B.21 1.701 A.23 B.19
1.644 A.21 B.24 1.673 A.22 B.22 1.702 A.23 B.20
1.645 A.21 B.25 1.674 A.22 B.23 1.703 A.23 B.21
1.646 A.21 B.26 1.675 A.22 B.24 1.704 A.23 B.22
1.647 A.21 B.27 1.676 A.22 B.25 1.705 A.23 B.23
1.648 A.21 B.28 1.677 A.22 B.26 1.706 A.23 B.24
1.649 A.21 B.29 1.678 A.22 B.27 1.707 A.23 B.25
1.650 A.21 B.30 1.679 A.22 B.28 1.708 A.23 B.26
1.651 A.21 B.31 1.680 A.22 B.29 1.709 A.23 B.27
1.652 A.22 B.1 1.681 A.22 B.30 1.710 A.23 B.28
1.653 A.22 B.2 1.682 A.22 B.31 1.711 A.23 B.29
1.654 A.22 B.3 1.683 A.23 B.1 1.712 A.23 B.30
1.655 A.22 B.4 1.684 A.23 B.2 1.713 A.23 B.31
1.656 A.22 B.5 1.685 A.23 B.3
Among the above compositions, preference is given to the following:
1.1, 1.4, 1.10, 1.12, 1.13, 1.21. 1.22, 1.24, 1.25. 1.26, 1.30, 1.31,
1.32, 1.35, 1.41, 1.43, 1.44, 1.52, 1.53, 1.55, 1.56, 1.57, 1.61, 1.62,
1.404, 1.407, 1.413, 1.415, 1.416, 1.424, 1.425, 1.427, 1.428, 1.429, 1.433,
1.434,
1.435, 1.438, 1.444, 1.446, 1.447, 1.455, 1.456, 1.458, 1.459, 1.460, 1.464,
1.465,
1.590, 1.593, 1.599, 1.601, 1.602, 1.610, 1.611, 1.613, 1.614, 1.615, 1.619,
1.620,
1.621, 1.624, 1.630, 1.632, 1.633, 1.641, 1.642, 1.644, 1.645, 1.646, 1.650,
1.651,
CA 02864272 2014-08-11
WO 2013/127862 PCT/EP2013/053943
1.652, 1.655, 1.661, 1.663, 1.664, 1.672, 1.673, 1.675, 1.676, 1.677, 1.681,
1,682,
1.683, 1.686, 1.692, 1.694, 1.695, 1.703, 1.704, 1.706, 1.707, 1.708, 1.712,
1.713.
More preference is given to following compositions:
5 1.1, 1.4, 1.13, 1.21. 1.22, 1.24, 1.25. 1.26, 1.31,
1.32, 1.35, 1.44, 1.52, 1.53, 1.55, 1.56, 1.57, 1.62,
1.404, 1.407, 1.416, 1.424, 1.425, 1.427, 1.428, 1.429, 1.434,
1.435, 1.438, 1.447, 1.455, 1.456, 1.458, 1.459, 1.460, 1.465,
1.590, 1.593, 1.602, 1.610, 1.611, 1.613, 1.614, 1.615, 1.620,
10 1.621, 1.624, 1.633, 1.641, 1.642, 1.644, 1.645, 1.646, 1.651,
1.652, 1.655, 1.664, 1.672, 1.673, 1.675, 1.676, 1.677, 1,682,
1.683, 1.686, 1.695, 1.703, 1.704, 1.706, 1.707, 1.708, 1.713.
It may be useful to apply the compositions according to the present invention
compris-
15 ing at least one the herbicide A and the at least one fungicide B in
combination with
safeners. Accordingly in another embodiment of the present invention the
compositions
according to the present invention comprise as additional component at least
one saf-
ener C.
Safeners are chemical compounds which prevent or reduce damage on useful
plants
without having a major impact on the herbicidal action of the herbicidal
active compo-
nents of the present compositions towards unwanted plants. They can be applied
either
before sowings (e.g. on seed treatments, shoots or seedlings) or in the pre-
emergence
application or post-emergence application of the useful plant. The at least
one safener
C and at least one the herbicide A and at least one fungicide B can be applied
simulta-
neously or in succession.
Suitable safeners C are e.g. (quinolin-8-oxy)acetic acids, 1-phenyl-5-
haloalky1-1H-
1,2,4-triazol-3-carboxylic acids, 1-phenyl-4,5-dihydro-5-alkyl-1H-pyrazol-3,5-
dicarboxylic acids, 4,5-dihydro-5,5-diary1-3-isoxazol carboxylic acids,
dichloroacetam-
ides, alpha-oximinophenylacetonitriles, acetophenonoximes, 4,6-dihalo-2-
phenylpyrimidines, N[[4-(aminocarbonyl)phenyl]sulfony1]-2-benzoic amides, 1,8-
naphthalic anhydride, 2-halo-4-(haloalkyl)-5-thiazol carboxylic acids,
phosphorthiolates
and N-alkyl-O-phenylcarbamates and their agriculturally acceptable salts and
their ag-
riculturally acceptable derivatives such amides, esters, and thioesters,
provided they
have an acid group.
Examples of preferred safeners C are benoxacor, cloquintocet, cyometrinil,
cyprosul-
famide, dichlormid, dicyclonon, dietholate, fenchlorazole, fenclorim,
flurazole, fluxofen-
CA 02864272 2014-08-11
WO 2013/127862
PCT/EP2013/053943
16
im, furilazole, isoxadifen, mefenpyr, mephenate, naphthalic anhydride,
oxabetrinil,
4-(dichloroacetyI)-1-oxa-4-azaspiro[4.5]decane (M0N4660, CAS 71526-07-3),
2,2,5-
trimethy1-3-(dichloroacety1)-1,3-oxazolidine (R-29148, CAS 52836-31-4) and N-
(2-
MethoxybenzoyI)-4-[(methylaminocarbonyl)amino]benzenesulfonamide (CAS 129531-
12-0).
Especially preferred safeners C are benoxacor, cloquintocet, cyprosulfamide,
dichlor-
mid, fenchlorazole, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen,
mefenpyr,
naphthalic anhydride, oxabetrinil, 4-(dichloroacetyI)-1-oxa-4-
azaspiro[4.5]decane
(M0N4660, CAS 71526-07-3), 2,2,5-trimethy1-3-(dichloroacety1)-1,3-oxazolidine
(R-
29148, CAS 52836-31-4) and N-(2-Methoxybenzoy1)-4-[(methylaminocarbony1)-
amino]benzenesulfonamide (CAS 129531-12-0).
Particularly preferred safeners C are benoxacor, cloquintocet, cyprosulfamide,
dichlor-
mid, fenchlorazole, fenclorim, furilazole, isoxadifen, mefenpyr, naphtalic
anhydride, 4-
(dichloroacetyI)-1-oxa-4-azaspiro[4.5]decane (M0N4660, CAS 71526-07-3), 2,2,5-
trimethy1-3-(dichloroacety1)-1,3-oxazolidine (R-29148, CAS 52836-31-4) and N-
(2-
MethoxybenzoyI)-4-[(methylaminocarbonyl)amino]benzenesulfonamide (CAS 129531-
12-0).
The safeners C are known safeners, see, for example, The Compendium of
Pesticide
Common Names (http://www.alanwood.net/pesticides/); Farm Chemicals Handbook
2000 volume 86, Meister Publishing Company, 2000; B. Hock, C. Fedtke,
R. R. Schmidt, Herbizide [Herbicides], 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 for the 7th edition,
Weed
Science Society of America, 1998.
The assignment of the active compounds to the respective mechanisms of action
is
based on current knowledge. If several mechanisms of action apply to one
active com-
pound, this substance was only assigned to one mechanism of action.
If the herbicide A, the fungicide B and/or the safener C are capable of
forming geomet-
rical isomers, for example E/Z isomers, both the pure isomers and mixtures
thereof
may be used in the compositions according to the invention. If the herbicide A
and/or
the fungicide B have one of more centers of chirality and are thus present as
enantio-
mers or diastereomers, both the pure enantiomers and diastereomers and
mixtures
thereof may be used in the compositions according to the invention.
CA 02864272 2014-08-11
WO 2013/127862 PCT/EP2013/053943
17
The herbicide A, the fungicide B and/or the safener C can be present in
different crystal
modifications whose biological activity may differ. They are likewise subject
matter of
the present invention.
If the herbicide A, the fungicide B and/or the safener C have ionizable
functional
groups, they can also be employed in the form of their agriculturally
acceptable salts.
Suitable are, in general, the salts of those cations and the acid addition
salts of those
acids whose cations and anions, respectively, have no adverse effect on the
activity of
the active compounds.
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, further
ammoni-
um and substituted ammonium in which one to four hydrogen atoms are replaced
by
Ci-C4-alkyl, hydroxy-C1-04-alkyl, Ci-C4-alkoxy-C1-04-alkyl, hydroxy-C1-04-
alkoxy-C1-04-
alkyl, phenyl or benzyl, preferably ammonium, methylammonium,
isopropylammonium,
dimethylammonium, diisopropylammonium, trimethylammonium, tetramethylammoni-
um, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium, 2-(2-
hydroxyeth-1-oxy)eth-1-ylammonium, di(2-hydroxyeth-1-yl)ammonium, benzyltrime-
thylammonium, benzyltriethylammonium, furthermore phosphonium ions, sulfonium
ions, preferably tri(Ci-04-alkyl)sulfonium, such as trimethylsulfonium, and
sulfoxonium
ions, preferably tri(Ci-04-alkyl)sulfoxonium.
Anions of useful acid addition salts are primarily chloride, bromide,
fluoride, iodide, hy-
drogensulfate, methylsulfate, sulfate, dihydrogenphosphate, hydrogenphosphate,
ni-
trate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate,
benzoate and
also the anions of Ci-04-alkanoic acids, preferably formate, acetate,
propionate and
butyrate.
The herbicide A, the fungicide B and/or the safener C having a carboxyl group
can be
employed in the form of the acid, in the form of an agriculturally suitable
salt or else in
the form of an agriculturally acceptable derivative in the compositions
according to the
invention, for example as amides, such as mono- and di-Ci-Co-alkylamides or
aryla-
mides, as esters, for example as allyl esters, propargyl esters, Ci-Cio-alkyl
esters,
alkoxyalkyl esters and also as thioesters, for example as Ci-Cio-alkylthio
esters. Pre-
ferred mono- and di-Ci-Co-alkylamides are the methyl and the dimethylamides.
Pre-
ferred arylamides are, for example, the anilides 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 Ci-04-
alkoxy-Ci-04-
CA 02864272 2014-08-11
WO 2013/127862 PCT/EP2013/053943
18
alkyl esters are the straight-chain or branched C1-C4-alkoxy ethyl esters, for
example
the methoxyethyl, ethoxyethyl or butoxyethyl ester. An example of a straight-
chain or
branched Ci-Cio-alkylthio ester is the ethylthio ester.
Suitable and preferred salts and esters of specific herbicides A are listed
above.
The compositions according to the present invention are useful in plant
protection of
rapeseed. The term "plant" as used herein includes all parts of a plant such
as germi-
nating seeds, emerging seedlings and herbaceous vegetation including all below-
ground portions (such as the roots) and aboveground portions.
Rapeseed (Brassica napus) is also known as rape, oilseed rape, rapa, rappi,
rapaseed,
colza and, in the case of one particular group of cultivars, canola. In the
terms of the
present invention, "rapeseed" is used as a synonym for all these terms,
inclusive cano-
la, as well as other cultivated Brassica species, such as for example field
mustard
(Brassica campestris) or Indian mustard (Brassica juncea).
The compositions according to the invention can also be used in genetically
modified
rapeseed plants. The term "genetically modified plants" is to be understood as
plants
whose genetic material has been modified by the use of recombinant DNA
techniques
to include an inserted sequence of DNA that is not native to that plant
species' genome
or to exhibit a deletion of DNA that was native to that species' genome,
wherein the
modification(s) cannot readily be obtained by cross breeding, mutagenesis or
natural
recombination alone. Often, a particular genetically modified plant will be
one that has
obtained its genetic modification(s) by inheritance through a natural breeding
or propa-
gation process from an ancestral plant whose genome was the one directly
treated by
use of a recombinant DNA technique. Typically, one or more genes have been
inte-
grated into the genetic material of a genetically modified plant in order to
improve cer-
tain properties of the plant. Such genetic modifications also include but are
not limited
to targeted post-translational modification of protein(s), oligo- or
polypeptides. e. g., by
inclusion therein of amino acid mutation(s) that permit, decrease, or promote
glycosyla-
tion or polymer additions such as prenylation, acetylation farnesylation, or
PEG moiety
attachment.
Rapeseed plants as well as the propagation material of said plants, which can
be treat-
ed with the inventive mixtures include all modified non-transgenic plants or
transgenic
plants, e.g. crops which tolerate the action of herbicides or fungicides or
insecticides
owing to breeding, including genetic engineering methods, or plants which have
modi-
fied characteristics in comparison with existing plants, which can be
generated for ex-
CA 02864272 2014-08-11
WO 2013/127862 PCT/EP2013/053943
19
ample by traditional breeding methods and/or the generation of mutants, or by
recom-
binant procedures.
For example, mixtures according to the present invention can be applied (as
seed
treatment, foliar spray treatment, in-furrow application or by any other
means) also to
plants which have been modified by breeding, mutagenesis or genetic
engineering in-
cluding but not limiting to agricultural biotech products on the market or in
development
(cf. http://www.bio.org/speeches/pubs/er/agri_products.asp).
Rapeseed plants that have been modified by breeding, mutagenesis or genetic
engi-
neering, e.g. have been rendered tolerant to applications of specific classes
of herbi-
cides, such as auxinic herbicides such as dicamba or 2,4-D; bleacher
herbicides such
as 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors or phytoene
desaturase
(PDS) inhibitors; acetolactate synthase (ALS) inhibitors such as sulfonylureas
or imid-
azolinones, e.g. imazamox; enolpyruvyl shikimate 3-phosphate synthase (EPSP)
inhibi-
tors such as glyphosate or sulfosate; glutamine synthetase (GS) inhibitors
such as
glufosinate or bialafos; protoporphyrinogen-IX oxidase (PPO) inhibitors; lipid
biosyn-
thesis inhibitors such as acetylCoA carboxylase (ACCase) inhibitors; or
photosynthetic
electron transport inhibitors at the photosystem II receptor site, such as
bromoxynil,
ioxynil, atrazine, simazine or terbutylazine as a result of conventional
methods of
breeding or genetic engineering; furthermore, plants have been made resistant
to mul-
tiple classes of herbicides through multiple genetic modifications, such as
resistance to
both glyphosate and glufosinate or to both glyphosate and a herbicide from
another
class such as ALS inhibitors, HPPD inhibitors, auxinic herbicides, or ACCase
inhibitors.
These herbicide resistance technologies are, for example, described in Pest
Manage-
ment Science 61, 2005, 246; 61, 2005, 258; 61, 2005, 277; 61, 2005, 269; 61,
2005,
286; 64, 2008, 326; 64, 2008, 332; Weed Science 57, 2009, 108; Australian
Journal of
Agricultural Research 58, 2007, 708; Science 316, 2007, 1185; and references
quoted
therein. Several cultivated plants have been rendered tolerant to herbicides
by mut-
genesis and conventional methods of breeding, e. g., Clearfield summer rape
(Cano-
la, BASF SE, Germany) being tolerant to imidazolinones, e. g., imazamox.
Genetic
engineering methods have been used to render rapeseed plants tolerant to
herbicides
such as glyphosate, imidazolinones and glufosinate, some of which are under
devel-
opment or commercially available under the brands or trade names RoundupReady
(glyphosate tolerant, Monsanto, USA) and LibertyLink (glufosinate tolerant,
Bayer
CropScience, Germany). Preferably, the rapeseed plants are tolerant against
herbi-
cides selected from the group of photosynthetic electron transport inhibitors
at the pho-
tosystem II receptor site, e.g. atrazine, simazine, terbutylazine or
bromoxynil or its agri-
culturally acceptable esters; acetolactate synthase inhibitors (ALS
inhibitors), e.g. ima-
CA 02864272 2014-08-11
WO 2013/127862 PCT/EP2013/053943
zamox or its agriculturally acceptable salts; auxinic herbicides, e.g. 2,4-D,
dicamba and
their agriculturally acceptable salts, esters and amides; EPSP synthase
inhibitors, e.g.
glyphosate, sulfosate and their agriculturally acceptable salts; and glutamine
synthase
inhibitors, e.g. glufosinate, bialafos and their agriculturally acceptable
salts.
5
Furthermore, rapeseed plants are also covered that are by the use of
recombinant
DNA techniques capable to synthesize one or more insecticidal proteins,
especially
those known from the bacterial genus Bacillus, particularly from Bacillus
thuringiensis,
such as delta-endotoxins, e. g., CrylA(b), CrylA(c), Cryl F, Cryl F(a2), Cryl
IA(b), CryIIIA,
10 CryIIIB(b1) or Cry9c; vegetative insecticidal proteins (VIP), e.g.,
VIP1, VIP2, VIP3 or
VIP3A; insecticidal proteins of bacteria colonizing nematodes, e. g.,
Photorhabdus spp.
or Xenorhabdus spp.; toxins produced by animals, such as scorpion toxins,
arachnid
toxins, wasp toxins, or other insect-specific neurotoxins; toxins produced by
fungi, such
as Streptomycetes toxins, plant lectins, such as pea or barley lectins;
agglutinins; pro-
15 teinase inhibitors, such as trypsin inhibitors, serine protease
inhibitors, patatin, cystatin
or papain inhibitors; ribosome-inactivating proteins (RIP), such as ricin,
maize-RIP,
abrin, luffin, saporin or bryodin; steroid metabolism enzymes, such as 3-
hydroxy-steroid oxidase, ecdysteroid-IDP-glycosyl-transferase, cholesterol
oxidases,
ecdysone inhibitors or HMG-CoA-reductase; ion channel blockers, such as
blockers of
20 sodium or calcium channels; juvenile hormone esterase; diuretic hormone
receptors
(helicokinin receptors); stilbene synthase, bibenzyl synthase, chitinases or
glucanases.
In the context of the present invention these insecticidal proteins or toxins
are to be
understood expressly also as including pre-toxins, hybrid proteins, truncated
or other-
wise modified proteins. Hybrid proteins are characterized by a new combination
of pro-
tein domains, (see, e.g., WO 02/015701). Further examples of such toxins or
genet-
ically modified plants capable of synthesizing such toxins are disclosed, e.
g., in EP-A
374 753, WO 93/007278, WO 95/34656, EP-A427 529, EP-A 451 878, WO 03/18810
and WO 03/52073. The methods for producing such genetically modified plants
are
generally known to the person skilled in the art and are described, e. g., in
the publica-
tions mentioned above. These insecticidal proteins contained in the
genetically modi-
fied plants impart to the plants producing these proteins tolerance to harmful
pests from
all taxonomic groups of arthropods, especially to beetles (Coleoptera), two-
winged in-
sects (Diptera), and moths (Lepidoptera) and to nematodes (Nematoda).
Genetically
modified plants capable to synthesize one or more insecticidal proteins are,
e. g., de-
scribed in the publications mentioned above.
Furthermore, rapeseed plants are also covered that are by the use of
recombinant
DNA techniques capable to synthesize one or more proteins to increase the
resistance
or tolerance of those plants to bacterial, viral or fungal pathogens. Examples
of such
CA 02864272 2014-08-11
WO 2013/127862 PCT/EP2013/053943
21
proteins are the so-called "pathogenesis-related proteins" (PR proteins, see,
e.g., EP-A
392 225), plant disease resistance genes or T4-lyso-zym. The methods for
producing
such genetically modified plants are generally known to the person skilled in
the art and
are described, e.g., in the publications mentioned above.
Furthermore, rapeseed plants are also covered that are by the use of
recombinant
DNA techniques capable to synthesize one or more proteins to increase the
productivi-
ty (e.g., bio-mass production, grain yield, starch content, oil content or
protein content),
tolerance to drought, salinity or other growth-limiting environmental factors
or tolerance
to pests and fungal, bacterial or viral pathogens of those plants.
Furthermore, plants are also covered that contain by the use of recombinant
DNA
techniques a modified amount of ingredients or new ingredients, specifically
to improve
human or animal nutrition, e. g., oil crops that produce health-promoting long-
chain
omega-3 fatty acids or unsaturated omega-9 fatty acids (e. g., Nexera rape,
Dow
AgroSciences, Canada).
Furthermore, plants are also covered that contain by the use of recombinant
DNA
techniques a modified amount of ingredients or new ingredients, specifically
to improve
raw material production.
The compositions to be used according to the invention or the crop protection
composi-
tions comprising them or formulated therefrom can be used, for example, in the
form of
ready-to-spray aqueous solutions, powders, suspensions, also highly
concentrated
aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions,
pastes,
dusts, materials for broadcasting, or granules, by means of spraying,
atomizing, dust-
ing, broadcasting or watering or treatment of the seed or mixing with the
seed. The use
forms depend on the intended purpose; in any case, they should ensure the
finest pos-
sible distribution of the active compounds according to the invention.
The crop protection compositions comprise an effective amount of the
composition
according to the invention, i.e. at least one herbicide A or an agriculturally
useful salt
thereof and at least one fungicide B, and also auxiliaries customary for
formulating crop
protection agents.
Examples for composition types are suspensions (SC, OD, FS), emulsifiable
concen-
trates (EC), emulsions (EW, EO, ES), pastes, pastilles, wettable powders or
dusts
(WP, SP, SS, WS, DP, DS) or granules (GR, FG, GG, MG), which can be water-
CA 02864272 2014-08-11
WO 2013/127862 PCT/EP2013/053943
22
soluble or wettable, as well as gel formulations for the treatment of plant
propagation
materials such as seeds (GF).
Usually the composition types (e. g. SC, OD, FS, EC, WG, SG, WP, SP, SS, WS,
GF)
are employed diluted. Composition types such as DP, DS, GR, FG, GG and MG are
usually used undiluted.
The compositions are prepared in a known manner (cf. US 3,060,084, EP-A 707
445
(for liquid concentrates), Browning: "Agglomeration", Chemical Engineering,
Dec. 4,
1967, 147-48, Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New
York, 1963, S. 8-57 und if. WO 91/13546, US 4,172,714, US 4,144,050, US
3,920,442,
US 5,180,587, US 5,232,701, US 5,208,030, GB 2,095,558, US 3,299,566,
Klingman:
Weed Control as a Science (J. Wiley & Sons, New York, 1961), Hance et al.:
Weed
Control Handbook (8th Ed., Blackwell Scientific, Oxford, 1989) and Mollet, H.
and
Grubemann, A.: Formulation technology (Wiley VCH Verlag, Weinheim, 2001).
The crop protection compositions may also comprise auxiliaries which are
customary in
agrochemical compositions. The auxiliaries used depend on the particular
application
form and active substance, respectively.
Examples of auxiliaries customary for the formulation of crop protection
agents are
inert auxilaries, solid or liquid carriers, surfactants (such as dispersants,
protective col-
loids, emulsifiers, wetting agents and tackifiers), organic and inorganic
thickeners, bac-
tericides, antifreeze agents, antifoams, optionally colorants and, for seed
formulations,
adhesives.
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 poly-
saccharides, such as xanthan gum (Kelzan from Kelco), Rhodopol 23 (Rhone Pou-
lenc) or Veegum (from R.T. Vanderbilt), and also organic and inorganic sheet
miner-
als, such as Attaclay (from Engelhardt).
Examples of antifoams are silicone emulsions (such as, for example, Silikon
SRE,
Wacker or Rhodorsil from Rhodia), long-chain alcohols, fatty acids, salts of
fatty ac-
ids, organofluorine compounds and mixtures thereof.
Bactericides can be added for stabilizing the aqueous herbicidal formulations.
Exam-
ples of bactericides are bactericides based on diclorophen and benzyl alcohol
hemi-
formal (Proxel 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 Rho-
damin B, C.I. Pigment Red 112 and C.I. Solvent Red 1, and also pigment blue
15:4,
CA 02864272 2014-08-11
WO 2013/127862 PCT/EP2013/053943
23
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 (tackifiers or binders) are polyvinylpyrrolidone,
polyvinyl ace-
tate, polyvinyl alcohol and cellulose ethers (Tylose , shin-Etsu, Japan).
Suitable inert auxiliaries are, for example, the following:
mineral oil fractions of medium to high boiling point, such as kerosene and
diesel oil,
furthermore coal tar oils and oils of vegetable or animal origin, aliphatic,
cyclic and ar-
omatic hydrocarbons, for example paraffin, tetrahydronaphthalene, alkylated
naphtha-
lenes and their derivatives, alkylated benzenes and their derivatives,
alcohols such as
methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as
cyclohexa-
none or strongly polar solvents, for example amines such as N-
methylpyrrolidone, and
water.
Suitable carriers include liquid and solid carriers.
Liquid carriers include e.g. non-aqueous solvents such as cyclic and aromatic
hydro-
carbons, e.g. paraffins, tetrahydronaphthalene, alkylated naphthalenes and
their deny-
atives, 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, kao-
lin, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth,
calcium sul-
fate, magnesium sulfate and magnesium oxide, ground synthetic materials,
fertilizers
such as ammonium sulfate, ammonium phosphate, ammonium nitrate and ureas, and
products of vegetable origin, such as cereal meal, tree bark meal, wood meal
and nut-
shell meal, cellulose powders, or other solid carriers.
Suitable surfactants (adjuvants, wetting agents, tackifiers, dispersants and
also emulsi-
fiers) are the alkali metal salts, alkaline earth metal salts and ammonium
salts of aro-
matic sulfonic acids, for example lignosulfonic acids (e.g. Borrespers-types,
Borre-
gaard), phenolsulfonic acids, naphthalenesulfonic acids (Morwet types, Akzo
Nobel)
and dibutylnaphthalenesulfonic acid (Nekal types, BASF AG), and of fatty
acids, alkyl-
and alkylarylsulfonates, alkyl sulfates, lauryl ether sulfates and fatty
alcohol sulfates,
and 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
for-
maldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl-, octyl- or
CA 02864272 2014-08-11
WO 2013/127862 PCT/EP2013/053943
24
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 pro-
teins, polysaccharides (e.g. methylcellulose), hydrophobically modified
starches, poly-
vinyl alcohol (Mowiol types Clariant), polycarboxylates (BASF AG, Sokalan
types), pol-
yalkoxylates, polyvinylamine (BASF AG, Lupamine types), polyethyleneimine
(BASF
AG, Lupasol types), polyvinylpyrrolidone and copolymers thereof.
Powders, materials for broadcasting and dusts can be prepared by mixing or
grinding
the active ingredients together with a solid carrier.
Granules, for example coated granules, impregnated granules and homogeneous
granules, can be prepared by binding the active ingredients to solid carriers.
Aqueous use forms can be prepared from emulsion concentrates, suspensions,
pastes,
wettable powders or water-dispersible granules by adding water. To prepare
emul-
sions, pastes or oil dispersions, the components of the compositions according
to the
invention either as such or dissolved in an oil or solvent, can be homogenized
in water
by means of a wetting agent, tackifier, dispersant or emulsifier.
Alternatively, it is also
possible to prepare concentrates comprising active compound, wetting agent,
tackifier,
dispersant or emulsifier and, if desired, solvent or oil, which are suitable
for dilution with
water.
In the formulation of the compositions according to the present invention the
active
ingredients are present in suspended, emulsified or dissolved form. The
formulation
according to the invention can be in the form of aqueous solutions, powders,
suspen-
sions, also highly-concentrated aqueous, oily or other suspensions or
dispersions,
aqueous emulsions, aqueous microemulsions, aqueous suspo-emulsions, oil disper-
sions, pastes, dusts, materials for spreading or granules.
The compositions of the invention can for example be formulated as follows:
1. Products for dilution with water
A Water-soluble concentrates (SL, LS)
10 parts by weight of active compound are dissolved in 90 parts by weight of
water or a
water-soluble solvent. As an alternative, wetters or other adjuvants are
added. The
active compound dissolves upon dilution with water. This gives a formulation
with an
active compound content of 10% by weight.
B Dispersible concentrates (DC)
20 parts by weight of active compound are dissolved in 70 parts by weight of
cyclohex-
anone with addition of 10 parts by weight of a dispersant, for example
polyvinylpyrroli-
CA 02864272 2014-08-11
WO 2013/127862 PCT/EP2013/053943
done. Dilution with water gives a dispersion. The active compound content is
20% by
weight
C Emulsifiable concentrates (EC)
15 parts by weight of active compound are dissolved in 75 parts by weight of
an organ-
5 ic solvent (eg. alkylaromatics) with addition of calcium
dodecylbenzenesulfonate 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.
D Emulsions (EW, EO, ES)
25 parts by weight of active compound are dissolved in 35 parts by weight of
an organ-
10 ic solvent (eg. alkylaromatics) with addition of calcium
dodecylbenzenesulfonate 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 (e.g. Ultraturrax) and made
into a
homogeneous emulsion. Dilution with water gives an emulsion. The formulation
has an
active compound content of 25% by weight.
15 E Suspensions(SC, OD, FS)
In an agitated ball mill, 20 parts by weight of active compound are comminuted
with
addition of 10 parts by weight of dispersants and wetters and 70 parts by
weight of wa-
ter 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
20 formulation is 20% by weight.
F Water-dispersible granules and water-soluble granules (WG, SG)
50 parts by weight of active compound 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,
fluid-
25 ized bed). Dilution with water gives a stable dispersion or solution of
the active com-
pound. The formulation has an active compound content of 50% by weight.
G Water-dispersible powders and water-soluble powders (WP, SP, SS, WS)
75 parts by weight of active compound 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
content of
the formulation is 75% by weight.
H Gel formulations (GF)
In a ball mill, 20 parts by weight of active compound, 10 parts by weight of
dispersant,
1 part by weight of gelling agent and 70 parts by weight of water or of an
organic sol-
vent 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 (DP, DS)
CA 02864272 2014-08-11
WO 2013/127862 PCT/EP2013/053943
26
parts by weight of active compound 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)
5 0.5 parts by weight of active compound 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 are dissolved in 90 parts by weight of
an organ-
ic solvent, for example xylene. This gives a product to be applied undiluted
with an ac-
tive compound content of 10% by weight.
The concentrations of the active compounds in the ready-to-use preparations
can be
varied within wide ranges. In general, the formulations comprise from 0.001 to
98% by
weight, preferably 0.01 to 95% by weight of at least one active compound. The
active
compounds are employed in a purity of from 90% to 100%, preferably 95% to 100%
(according to NMR spectrum).
In the ready-to-use preparations, i.e. in the compositions to be used
according to the
invention in the form of crop protection compositions, the components A and B
can be
present formulated jointly or separately in suspended, emulsified or dissolved
form.
The use forms depend entirely on the intended applications.
The components A and B can be formulated and applied jointly or separately,
simulta-
neously or in succession, before, during or after the emergence of the plants.
In case of
separate application, the order of the application of the components A and B
is of minor
importance. The only thing that is important is that the at least one active
components
A and B are present simultaneously at the site of action, i.e. are at the same
time in
contact with or taken up by the plant to be controlled and/or safened.
A first embodiment of the invention relates to the use compositions in the
form of a crop
protection composition formulated as a 1-component composition comprising the
at
least one active component A, at least one further active component B and
optionally at
least one safener C, and also a solid or liquid carrier and/or and, one or
more surfac-
tants, and, if desired, one or more further auxiliaries customary for crop
protection
compositions.
CA 02864272 2014-08-11
WO 2013/127862 PCT/EP2013/053943
27
A second embodiment of the invention relates to compositions in the form of a
crop
protection composition formulated as a 2-component composition comprising a
first
formulation (component) comprising the at least one active component A, a
solid or
liquid carrier and, if appropriate, one or more surfactants, and a second
component
comprising at least one further active component B, and optionally at least
one safener
C, and a solid or liquid carrier and, if appropriate, and/or one or more
surfactants,
where additionally both components may also comprise further auxiliaries
customary
for crop protection compositions.
The compositions to be used according to the invention are suitable as
herbicides.
They are suitable as such or as an appropriately formulated composition. The
composi-
tions according to the invention control vegetation on non-crop areas very
efficiently,
especially at high rates of application. They act against broad-leafed weeds
and grass
weeds in rapeseed crops without causing any significant damage to the crop
plants.
This effect is mainly observed at low rates of application.
Furthermore, it has been found that the compositions according to the
invention are
also suitable for the defoliation and/or desiccation of plant parts. In this
regard compo-
sitions have been found for the desiccation and/or defoliation of rapeseed
plants, pro-
cesses for preparing these compositions, and methods for desiccating and/or
defoliat-
ing rapeseed plants using the compositions according to the invention.
As desiccants, the compositions according to the invention are suitable in
particular for
desiccating the above-ground parts of rapeseed. This makes possible the fully
me-
chanical harvesting of these plants.
Also of economic interest is the facilitation of harvesting, which is made
possible by
concentrating within a certain period of time the dehiscence, or reduction of
adhesion
to the plant.
In the methods and uses according to the invention, it is principally of no
importance
whether the active compounds of components A and B are formulated and applied
jointly or separately and in which order application is carried out in the
case of separate
application.
In crop protection products, 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. It is known that in some cases
better crop
CA 02864272 2014-08-11
WO 2013/127862 PCT/EP2013/053943
28
plant compatibility can be achieved by joint application of specifically
acting herbicides
with organic active compounds, which act as antidotes or antagonists. Owing to
the
fact that they can reduce or even prevent damage to the crop plants, they are
also re-
ferred to as safeners.
It is therefore a further object of the present invention to provide
herbicidal composi-
tions, which are highly active against unwanted harmful plants, and, at the
same time,
the compositions should have good compatibility with useful plants. In
addition, the
compositions according to the invention should have a broad spectrum of
activity.
This object is also achieved by the herbicidal active compositions comprising
at least
one herbicide A as defined herein and at least one fungicide B as defined
herein.
The crop protection compositions comprise an herbicidally effective amount of
the
composition according to the invention, i.e. at least one herbicide A or an
agriculturally
useful salt thereof and at least one further active compound B, and also
auxiliaries cus-
tomary for formulating crop protection agents as defined herein.
The required application rate of pure active compound composition, i.e. A and
B and, if
appropriate, C without formulation auxiliaries depends on the composition of
the plant
stand, on the development stage of the plants, on the climatic conditions at
the site of
use and on the application technique. In general, the application rate of A
and B is from
0.001 to 3 kg/ha, preferably from 0.005 to 2.5 kg/ha and in particular from
0.01 to 2
kg/ha of active substance (a.s.).
The required application rates of the herbicide A are generally in the range
of from
0.0005 kg/ha to 2.5 kg/ha and preferably in the range of from 0.005 kg/ha to 2
kg/ha or
0.01 kg/ha to 1.5 kg/h of a.s.
The required application rates of the fungicide B are generally in the range
of from
0.0005 kg/ha to 2.5 kg/ha and preferably in the range of from 0.005 kg/ha to 2
kg/ha or
0.01 kg/ha to 1.5 kg/h of a.s.
The required application rates of the optional safener C are generally in the
range of
from 0.0005 kg/ha to 2.5 kg/ha and preferably in the range of from 0.005 kg/ha
to 2
kg/ha or 0.01 kg/ha to 1.5 kg/h of a.s.
The compositions according to the invention are applied to the plants mainly
by spray-
ing the leaves. Here, the application can be carried out using, for example,
water as
CA 02864272 2014-08-11
WO 2013/127862 PCT/EP2013/053943
29
carrier by customary spraying techniques using spray liquor amounts of from
about 100
to 1000 I/ha (for example from 300 to 400 I/ha). The herbicidal compositions
may also
be applied by the low-volume or the ultra-low-volume method, or in the form of
mi-
crogranules.
The herbicidal compositions according to the present invention can be applied
pre- or
post-emergence or together with the seed of a crop plant. It is also possible
to apply
In a further embodiment, the composition to be used according to the invention
can be
applied by treating seed. The treatment of seed comprises essentially all
procedures
The term seed comprises seed of all types, such as, for example, corns, seeds,
fruits,
tubers, seedlings and similar forms. Here, preferably, the term seed describes
corns
and seeds.
of transgenic plants or plants obtained by customary breeding methods.
The rates of application of the active compound are from 0.0001 to 3.0,
preferably 0.01
to 1.0 kg/ha of active substance (a.s.), depending on the control target, the
season, the
target plants and the growth stage. To treat the seed, the compounds I are
generally
employed in amounts of from 0.001 to 10 kg per 100 kg of seed.
Moreover, it may be advantageous to apply the compositions of the present
invention
on their own or jointly in combination with other crop protection agents, for
example
CA 02864272 2014-08-11
WO 2013/127862 PCT/EP2013/053943
with agents for controlling pests or phytopathogenic fungi or bacteria or with
groups of
active compounds which regulate growth. Also of interest is the miscibility
with mineral
salt solutions which are employed for treating nutritional and trace element
deficien-
cies. Non-phytotoxic oils and oil concentrates can also be added.
5
The herbicidal effect of the compositions to be used according to the present
invention
comprising at least an herbicide A and a fungicide B, and optionally one or
more saf-
eners C, on the growth of undersirable plants and the safening action on crops
was
demonstrated by the following greenhouse experiments:
The culture containers used were plastic pots containing loamy sand with
approximate-
ly 3.0% of humus as substrate. The seeds of the test plants were sown
separately for
each species.
For the pre-emergence treatment, the active compounds, suspended or emulsified
in
water, were applied directly after sowing by means of finely distributing
nozzles. The
containers were irrigated gently to promote germination and growth and
subsequently
covered with transparent plastic hoods until the plants had rooted. This cover
caused
uniform germination of the test plants unless this was adversely affected by
the active
compounds.
For the post-emergence treatment, the test plants were grown to a plant height
of from
3 to 15 cm, depending on the plant habit, and only then treated with the
active com-
pounds which had been suspended or emulsified in water. To this end, the test
plants
were either sown directly, and grown in the same containers, or they were
first grown
separately as seedlings and transplanted into the test containers a few days
prior to
treatment.
Depending on the species, the plants were kept at 10- 25 C and 20- 35 C,
respective-
ly. The test period extended over 2 to 4 weeks. During this time, the plants
were tended
and their response to the individual treatments was evaluated.
Evaluation was carried out using a scale from 0 to 100. 100 means no emergence
of
the plants, or complete destruction of at least the above-ground parts, and 0
means no
damage or normal course of growth. Good herbicidal activity is given at values
of at
least 70, and very good herbicidal activity is given at values of at least 85.
The respective stated components A and B, and if appropriate, C were
formulated as a
10% by weight strength emulsion concentrate and, with addition of the amount
of sol-
vent system, introduced into the spray liquor used for applying the active
compound. In
the examples, the solvent used was water.
CA 02864272 2014-08-11
WO 2013/127862 PCT/EP2013/053943
31
The test period extended over 20 and 21 days, respectively. During this time,
the plants
were tended, and their reaction to the treatment with active compound was
monitored.
In the examples below, using the method of S. R. Colby (1967) "Calculating
synergistic
and antagonistic responses of herbicide combinations", Weeds 15, p. 22ff., the
value
E, which is expected if the activity of the individual active compounds is
only additive,
was calculated.
E = X + Y ¨ (X.Y/100)
where
X = percent activity using active compound A at an application rate a;
Y = percent activity using active compound B at an application rate b;
E = expected activity (in %) by A + B at application rates a + b.
If the value found experimentally is higher than the value E calculated
according to
Colby, a synergistic effect is present.
In all uses and methods of the present invention the compositions preferably
contain
the at least one compound A and the at least one compound B in synergistically
effec-
tive amounts, i.e. in a weight ratio of A and B such that a synergistic effect
takes place.
This means that the relative amount, i.e. the weight ratio of the at least one
compound
A and the at least one compound B in the composition provides for an increased
herbi-
cidal efficacy on at least one weed which exceeds the additive herbicidal
efficacy of the
compounds of the composition as calculated from the herbicidal efficacy of the
individ-
ual compounds at a given application rate. The calculation of the additive
efficacies can
be performed e.g. by Colby's formula (Colby, S.R. "Calculating synergistic and
antago-
nistic responses of herbicide Combinations", Weeds, 15, 20-22, 1967).
Synergism is
present if the observed efficacy is greater than the calculated efficacy.
To ensure synergism, the at least one compound of the formula A and the at
least one
compound B are preferably present in the compositions of the present invention
in a
total weight ratio of from 100:1 to 1:100, more preferably from 50:1 to 1:50,
even more
preferably from 20:1 to 1:20, and in particular from 10:1 to 1:10, e.g. from
5:1 to 1:5 or
from 3:1 to 1:3 or from 2:1 to 1:2.
