U.S. patent application number 12/636420 was filed with the patent office on 2010-05-13 for selective herbicides based on a substituted phenylsulfonylaminocarbonyl-triazolinone.
This patent application is currently assigned to Arysta LifeScience North America, LLC. Invention is credited to Peter Dahmen, DIETER FEUCHT, Klaus Lurssen, Klaus-Helmut Muller, Hans-Joachim Santel, Ingo Wetcholowsky.
Application Number | 20100120622 12/636420 |
Document ID | / |
Family ID | 7883188 |
Filed Date | 2010-05-13 |
United States Patent
Application |
20100120622 |
Kind Code |
A1 |
FEUCHT; DIETER ; et
al. |
May 13, 2010 |
SELECTIVE HERBICIDES BASED ON A SUBSTITUTED
PHENYLSULFONYLAMINOCARBONYL-TRIAZOLINONE
Abstract
The present invention relates to selective-herbicidal
compositions, characterized in that they contain an effective
amount of the compound
2-(2-trifluoromethoxy-phenylsulphonylaminocarbonyl)-4-methyl-5-methoxy-2,-
4-dihydro-3H-1,2,4-triazol-3-one of the formula (I) ##STR00001##
and/or of salts of the compound of the formula (I), and to the use
of these compositions for the selective control of weeds in crops
of cereals, in particular crops of wheat, and to methods for the
selective control of weeds in crops of cereals by applying the
compositions together with surfactants and/or customary
extenders.
Inventors: |
FEUCHT; DIETER; (Monheim,
DE) ; Santel; Hans-Joachim; (Leawood, KS) ;
Lurssen; Klaus; (Bergisch Gladbach, DE) ;
Wetcholowsky; Ingo; (Rua Avare, BR) ; Dahmen;
Peter; (Neuss, DE) ; Muller; Klaus-Helmut;
(Dusseldorf, DE) |
Correspondence
Address: |
PILLSBURY WINTHROP SHAW PITTMAN LLP
ATTENTION: DOCKETING DEPARTMENT, P.O BOX 10500
McLean
VA
22102
US
|
Assignee: |
Arysta LifeScience North America,
LLC
Cary
NC
|
Family ID: |
7883188 |
Appl. No.: |
12/636420 |
Filed: |
December 11, 2009 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
|
|
10393359 |
Mar 21, 2003 |
7651978 |
|
|
12636420 |
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09806338 |
May 14, 2001 |
6562760 |
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PCT/EP99/06989 |
Sep 21, 1999 |
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10393359 |
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Current U.S.
Class: |
504/273 ;
548/263.4 |
Current CPC
Class: |
A01N 47/38 20130101 |
Class at
Publication: |
504/273 ;
548/263.4 |
International
Class: |
A01N 43/653 20060101
A01N043/653; C07D 249/12 20060101 C07D249/12; A01P 13/00 20060101
A01P013/00 |
Foreign Application Data
Date |
Code |
Application Number |
Oct 2, 1998 |
DE |
198 45 407.4 |
Claims
1. Selective-herbicidal compositions, characterized in that they
contain an effective amount of the compound
2-(2-trifluoromethoxy-phenyl-sulphonylaminocarbonyl)-4-methyl-5-methoxy-2-
,4-dihydro-3H-1,2,4-triazol-3-one of the formula (I) ##STR00011##
and/or of salts of the compound of the formula (I).
2. Selective-herbicidal compositions according to claim 1,
characterized in that they contain an effective amount of the
sodium salt of the compound of the formula (I).
3. The use of the compound
2-(2-trifluoromethoxy-phenylsulphonyl-aminocarbonyl)-4-methyl-5-methoxy-2-
,4-dihydro-3H-1,2,4-triazol-3-one of the formula (I) according to
claim 1 and/or of salts of the compound of the formula (I) for the
selective control of weeds in crops of cereals.
4. The use of the sodium salt of the compound
2-(2-trifluoromethoxy-phenylsulphonylaminocarbonyl)-4-methyl-5-methoxy-2,-
4-dihydro-3H-1,2,4-triazol-3-one of the formula (I) according to
claim 1 for the selective control of weeds in crops of cereals.
5. The use of the compound
2-(2-trifluoromethoxy-phenylsulphonyl-aminocarbonyl)-4-methyl-5-methoxy-2-
,4-dihydro-3H-1,2,4-triazol-3-one of the formula (I) according to
claim 1 and/or of salts of the compound of the formula (I) for the
selective control of weeds in crops of wheat.
6. Method for the selective control of weeds in crops of cereals,
characterized in that the compound
2-(2-trifluoromethoxy-phenylsulphonylaminocarbonyl)-4-methyl-5-methoxy-2,-
4-dihydro-3H-1,2,4-triazol-3-one of the formula (I) according to
claim 1 and/or salts of the compound of the formula (I) are applied
together with surfactants and/or customary extenders in crops of
cereals.
Description
[0001] The invention relates to the use of the known compound
2-(2-trifluoromethoxy-phenylsulphonylaminocarbonyl)-4-methyl-5-methoxy-2,-
4-dihydro-3H-1,2,4-triazol-3-one of the formula (I) shown
below--alias
4,5-dihydro-3-methoxy-4-methyl-5-oxo-N[[2-(trifluoromethoxy)-phenyl]-sulp-
honyl]-1H-1,2,4-triazol-l-carboxamide (CAS-Reg.-No.:
145026-88-6)--and its salts, in particular its sodium salt
(CAS-Reg.-No. 181274-17-9), for the selective control of weeds in
crops of useful plants, in particular for controlling problematic
weeds in cereals.
[0002] Substituted phenylsulphonylaminocarbonyltriazolinones such
as, for example, the compounds
2-(2-trifluoromethoxy-phenylsulphonylaminocarbonyl)-4-ethyl-5-methoxy-2,4-
-dihydro-3H-1,2,4-triazol-3-one,
2-(2-trifluoromethoxy-phenyl-sulphonylaminocarbonyl)-4-methyl-5-ethoxy-2,-
4-dihydro-3H-1,2,4-triazol-3-one,
2-(2-trifluoromethoxy-phenylsulphonylaminocarbonyl)-4-methoxy-5-methyl-2,-
4-dihydro-3H-1,2,4-triazol-3-one,
2(2-trifluoromethyl-phenylsulphonylamino-carbonyl)-4-methyl-5-methoxy-2,4-
-dihydro-3H-1,2,4-triazol-3-one and
2-(2-di-fluoromethoxy-phenylsulphonylaminocarbonyl)-4-methyl-4-methoxy-2,-
4-dihydro-3H-1,2,4-triazol-3-one and their salts, processes for
preparing these compounds and their use as herbicides are the
subject of earlier patent applications (cf. EP-341 489, EP-422 469,
EP-507 171, U.S. Pat. No. 5,534,486). The individual abovementioned
substituted phenylsulphonylaminocarbonyltriazolinones have a
molecular structure which is very similar to that of the compound
(I) to be used according to the invention but, in contrast to this
compound, they show shortcomings in their activity or activity gaps
in the case of certain weeds.
[0003] Surprisingly, it has now been found that the compound
2-(2-trifluoromethoxy-phenylsulphonylaminocarbonyl)-4-methyl-5-methoxy-2,-
4-dihydro-3H-1,2,4-triazol-3-one (I) and salts thereof, in
particular the sodium salt of the compound of the formula (I), in
comparison with the abovementioned structurally similar compounds,
show considerably stronger activity against some weeds in cereal
crops which are difficult to control, combined with very good
compatibility with cereal species, such as, in particular, wheat,
and are therefore particularly suitable for the efficient and
selective control of weeds in cereals, in particular in wheat. The
activity gaps observed with the abovementioned comparative
compounds which are closely related to (I) do not occur in the weed
spectrum of the compound (I) and its salts.
[0004] The invention provides selective-herbicidal compositions,
characterized in that they contain an effective amount of the
compound
2-(2-trifluoromethoxy-phenylsulphonylaminocarbonyl)-4-methyl-5-methoxy-2,-
4-dihydro -3H-1,2,4-triazol-3-one of the formula (I)
##STR00002##
and/or of salts of the compound of the formula (I), in particular
of their sodium salt [referred to as "(I)--Na-salt" in the use
examples].
[0005] The invention furthermore provides the use of the compound
2-(2-trifluoromethoxy-phenylsulphonylaminocarbonyl)-4-methyl-5-methoxy-2,-
4-dihydro-3H-1,2,4-triazol-3-one of the formula (I)--above--and/or
of salts of the compound of the formula (I), in particular of its
sodium salt, for the selective control of weeds in crops of
cereals, in particular in crops of wheat.
[0006] The invention furthermore provides a method for the
selective control of weeds in crops of cereals, in particular in
crops of wheat, which is characterized in that the compound
2-(2-trifluoromethoxy-phenylsulphonylaminocarbonyl)-4-methyl-5-methoxy-2,-
4-dihydro-3H-1,2,4-triazol-3-one of the formula (I)--above--and/or
salts of the compound of the formula (I), in particular its sodium
salt, is/are applied with surfactants and/or customary extenders in
crops of cereals.
[0007] The compound of the formula (I) and its Na salt are already
known (cf. U.S. Pat. No. 5,534,486--Examples 79 and 321).
[0008] The compound of the formula (I) and its salts have a broad
herbicidal activity. They can be used, for example, for controlling
the following weeds:
[0009] Dicotyledonous weeds of the orders: Sinapis, Lepidium,
Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium,
Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus,
Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus,
Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon,
Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium,
Ranunculus, Taraxacum.
[0010] Monocotyledonous weeds of the orders: Echinochloa, Setaria,
Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria,
Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon,
Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus,
Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis,
Alopecurus, Apera, Aegilops, Phalaris.
[0011] However, the use of the compound (I) and its salts is by no
means limited to these orders but extends in the same manner to
other plants as well.
[0012] The compound of the formula (I) and its salts have strong
herbicidal activity and a broad spectrum of activity when used on
the soil and on above-ground parts of plants. They are suitable for
the selective control of monocotyledonous and dicotyledonous weeds
in monocotyledonous crops, especially in cereals, in particular in
wheat, both by the pre-emergence and by the post-emergence
method.
[0013] Problematic weeds which can be controlled particularly well
with the compound of the formula (I) and its salts, in particular
its sodium salt, and whose control is less likely to succeed with
both conventional herbicides and more recent compounds of a similar
molecular structure are, in particular, Agropyron, Alopecurus,
Amaranthus, Apera, Avena, Brassica, Bromus, Capsella, Digitaria,
Echinochloa, Erysimum, Lolium, Matricaria, Phalaris, Poa,
Polygonum, Setaria, Sinapis, Thlaspi and Veronica.
[0014] The compound of the formula (I) and its salts, in particular
its sodium salt, can be converted into the customary formulations,
such as solutions, emulsions, wettable powders, suspensions,
powders, dusts, pastes, soluble powders, granules,
suspension/emulsion concentrates, natural and synthetic materials
impregnated with active compound, and very fine capsules in
polymeric substances.
[0015] These formulations are produced in a known manner, for
example by mixing the active compounds with extenders, that is
liquid solvents and/or solid carriers, optionally with the use of
surface-active agents, that is emulsifying agents and/or dispersing
agents and/or foam-forming agents.
[0016] If the extender used is water, it is also possible to employ
for example organic solvents as auxiliary solvents. Suitable liquid
solvents are essentially the following: aromatics, such as xylene,
toluene or alkylnaphthalenes, chlorinated aromatics, such as
chlorobenzenes, chlorinated aliphatics, such as chloroethylenes or
methylene chloride, aliphatic hydrocarbons, such as cyclohexane or
paraffins, for example petroleum fractions, mineral and vegetable
oils, alcohols, such as butanol or glycol and also their ethers and
esters, ketones, such as acetone, methyl ethyl ketone, methyl
isobutyl ketone or cyclohexanone, strongly polar solvents, such as
dimethylformamide and dimethyl sulphoxide, and also water.
[0017] Suitable solid carriers are: for example ammonium salts and
ground natural minerals, such as kaolins, clays, talc, chalk,
quartz, attapulgite, montmorillonite or diatomaceous earth, and
ground synthetic minerals, such as finely divided silica, alumina
and silicates; suitable solid carriers for granules are: for
example crushed and fractionated natural rocks such as calcite,
marble, pumice, sepiolite and dolomite, and also synthetic granules
of inorganic and organic meals, and granules of organic material
such as sawdust, coconut shells, maize cobs and tobacco stalks;
suitable emulsifying and/or foam-forming agents are: for example
non-ionic and anionic emulsifiers, such as polyoxyethylene fatty
acid esters, polyoxyethylene fatty alcohol ethers, for example
alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates,
arylsulphonates as well as protein hydrolysates; suitable
dispersing agents are: for example lignin-sulphite waste liquors
and methylcellulose.
[0018] Tackifiers such as carboxymethylcellulose and natural and
synthetic polymers in the form of powders, granules or latexes,
such as gum arabic, polyvinyl alcohol and polyvinyl acetate, as
well as natural phospholipids, such as cephalins and lecithins, and
synthetic phospholipids, can be used in the formulations. Other
possible additives are mineral and vegetable oils.
[0019] It is possible to use colourants such as inorganic pigments,
for example iron oxide, titanium oxide and Prussian Blue, and
organic dyes, such as alizarin dyes, azo dyes and metal
phthalocyanine dyes, and trace nutrients such as salts of iron,
manganese, boron, copper, cobalt, molybdenum and zinc.
[0020] The formulations in general contain between 0.1 and 95 per
cent by weight of active compound, preferably between 0.5 and
90%.
[0021] For the control of weeds, the compound of the formula (I)
and its salts, as such or in the form of their formulations, can
also be used as mixtures with known herbicides, finished
formulations or tank mixes being possible.
[0022] Possible components for the mixtures are known herbicides,
for example amidosulfuron, bentazon, bromoxynil,
carfentrazone(-ethyl), cinidon(-ethyl), clodi-nafop(-propargyl),
clopyralid, chlorsulfuron, chlortoluron, cyclosulfamuron, 2,4-D,
diclofop(-methyl), difenzoquat, diflufenican, florasulam,
flupyrsulfuron(-methyl, -sodium), pyraflufen(-ethyl), ethoxyfen,
fenoxaprop(-ethyl), fluoroglycofen(-ethyl), flupropacil,
fluroxypyr, iodosulfuron, isoproturon, mecoprop, metosulam,
metribuzin, metsulfuron(-methyl), pendimethalin, prosulfocarb,
pyridate, sulfosulfuron, thifensulfuron(-methyl), tralkoxydim,
triasulfuron, tribenuron-(-methyl), trifluralin.
[0023] Mixtures with other known active compounds, such as
fungicides, insecticides, acaricides, nematicides, bird repellents,
plant nutrients and agents which improve soil structure, are also
possible.
[0024] The compound of the formula (I) and its salts can be used as
such, in the form of their formulations or in the use forms
prepared therefrom by further dilution, such as ready-to-use
solutions, suspensions, emulsions, powders, pastes and granules.
They are used in the customary manner, for example by watering,
spraying, atomizing or scattering.
[0025] The compound of the formula (I) and its salts can be applied
either before or after emergence of the plants. They can also be
incorporated into the soil before sowing.
[0026] The amount of active compound used can vary within a
substantial range. It depends essentially on the nature of the
desired effect. In general, the amounts used are between 1 g and 1
kg of active compound per hectare of soil surface, preferably
between 5 g and 0.5 kg per ha.
[0027] The use of the compound of the formula (I) and its salts can
be seen from the following examples.
USE EXAMPLES
[0028] In the use examples, the compounds shown below are used as
comparative substances:
##STR00003##
2-(2-Trifluoromethoxy-phenylsulphonylaminnocarbonyl)-4-ethyl-5-methoxy-2,-
4-di-hydro-3H-1,2,4-triazol-3-one (known from EP-507 171, U.S. Pat.
No. 5,534,486--Example 87)
##STR00004##
[0029]
2-(2-Trifluoromethoxy-phenylsulphonylaminocarbonyl)-4-methyl-5-etho-
xy-2,4-dihydro-3H-1,2,4-triazol-3-one--sodium salt--(known from
U.S. Pat. No. 5,534,486--Example 260)
##STR00005##
[0031]
2-(2-Thfluoromethoxy-phenylsulphonylaminocarbonyl)-4-methoxy-5-meth-
yl-2,4-dihydro-3H-1,2,4-triazol-3-one (known from EP-422
469--Example 96; see also U.S. Pat. No. 5,057,144--Example 96)
##STR00006##
2-(2-Trifluoromethyl-phenylsulphonylaminocarbonyl)-4-methyl-5-methoxy-2,4-
-dihydro-3H-1,2,4-triazol-3-one--sodium salt (known from EP-507
171, U.S. Pat. No. 5,534,486--Example 187)
##STR00007##
[0032]
2-(2-Difluoromethoxy-phenylsulphonylaminocarbonyl)-4-methyl-5-metho-
xy-2,4-dihydro-3H-1,2,4-triazol-3-one--sodium salt (known from U.S.
Pat. No. 5,534,486--Example 319)
##STR00008##
[0033]
2-(2-Chlorodifluoromethoxy-phenylsulphonylaminocarbonyl)-4-methyl-5-
-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one--sodium salt (in the
claim of EP-507 171 and U.S. Pat. No. 5,534,486)
##STR00009##
[0034]
2-[2-(1,1,2,2-Tetrafluoroethoxy)-phenylsulphonylaminocarbonyl]-4-me-
thyl-5-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one (in the claim of
EP-507 171 and U.S. Pat. No. 5,534,486)
##STR00010##
[0035]
2-[2-(Pentafluoroethoxy)-phenylsulphonylaminocarbonyl]-4-methyl-5-m-
ethoxy-2,4-dihydro-3H-1,2,4-triazol-3-one--sodium salt (in the
claim of EP-507 171 and U.S. Pat. No. 5,534,486)
EXAMPLE A
[0036] Pre-Emergence Test/Greenhouse
[0037] Solvent: 5 parts by weight of acetone
[0038] Emulsifier: 1 part by weight of alkylaryl polyglycol
ether
[0039] To produce a suitable preparation of active compound, 1 part
by weight of active compound is mixed with the stated amount of
solvent, the stated amount of emulsifier is added and the
concentrate is diluted with water to the desired concentration.
[0040] Seeds of the test plants are sown in normal soil. After
about 24 hours, the soil is sprayed with the preparation of active
compound such that the particular amount of active compound desired
is applied per unit area. The concentration of the spray liquor is
chosen so that the particular amount of active compound desired is
applied in 500 ml of water per hectare.
[0041] After three weeks, the degree of damage to the plants is
assessed in % damage in comparison to the development of the
untreated control.
[0042] The figures denote: [0043] 0%=no effect (like untreated
control) [0044] 100%=total destruction
[0045] In this test, for example, the sodium salt of the compound
of the formula (I) exhibits, at an application rate of from 30
g/ha, very strong activity (efficacy 80% to 100%) against weeds,
such as, for example, Alopecurus, Avena, Bromus, Digitaria,
Echinochloa, Matricaria, Polygonum and Setaria, combined with very
good compatibility with crop plants, such as, for example, wheat,
whereas the comparative compounds (A), (C), (D), (E) and (F)
exhibit considerably weaker herbicidal activity and the comparative
compound (B) is not compatible with wheat (cf. Table A1). The
considerable superiority of (I)--Na-salt over the comparative
compound (G) is shown in Table A2 ["ai."="active ingredient"].
TABLE-US-00001 TABLE A1 Pre-emergence test/greenhouse Application
rate Active (g of compounds ai./ha) Wheat Alopecurus Avena Bromus
Digitaria Echinochloa Setaria Matricaria Polygonum (A) 30 0 20 0 40
0 50 60 0 0 (B) 30 50 70 80 -- -- -- -- -- 80 (C) 30 0 0 0 0 0 0 0
0 0 (D) 30 0 70 50 -- 80 -- -- 30 70 (E) 30 0 50 30 0 40 30 80 0 60
(F) 30 0 90 40 95 80 80 95 50 0 (I)- 30 0 100 95 100 100 80 100 100
90 Na- salt
TABLE-US-00002 TABLE A2 Pre-emergence test/greenhouse Active
Application rate compounds (g ai./ha) Alopecurus Avena Setaria (G)
250 50 0 50 (I)-Na-salt 250 100 99 99
EXAMPLE B
[0046] Post-Emergence Test/Greenhouse
[0047] Solvent: 5 parts by weight of acetone
[0048] Emulsifier: 1 part by weight of alkylaryl polyglycol
ether
[0049] To produce a suitable preparation of active compound, 1 part
by weight of active compound is mixed with the stated amount of
solvent, the stated amount of emulsifier is added and the
concentrate is diluted with water to the desired concentration.
[0050] Test plants which have a height of 5-15 cm are sprayed with
the preparation of active compound such that the particular amounts
of active compound desired are applied per unit area. The
concentration of the spray liquor is chosen so that the particular
amounts of active compound desired are applied in 500 ml of
water/ha.
[0051] After three weeks, the degree of damage to the plants is
assessed in % damage in comparison to the development of the
untreated control.
[0052] The figures denote: [0053] 0%=no effect (like untreated
control) [0054] 100%=total destruction
[0055] In this test, for example, the sodium salt of the compound
of the formula (I) exhibits, at an application rate of 60 g/ha,
strong activity (efficacy 70% to 100%) against weeds, such as, for
example, Agropyron, Alopecurus, Avena, Bromus, Lolium, Setaria and
Veronica, combined with very good compatibility with crop plants,
such as, for example, wheat, whereas the comparative compounds (A),
(B), (C), (D), (E) and (F) have considerably weaker herbicidal
activity (cf. Table B1). A considerable superiority of (I)--Na-salt
(at 125 g/ha) over the comparative compounds (G) and (H) (in each
case at 250 g/ha!) is shown in Table B2.
TABLE-US-00003 TABLE B1 Post-emergence test/greenhouse Application
Active rate compounds (g ai./ha) Wheat Agropyron Alopecurus Avena
Bromus Lolium Setaria Veronica (A) 60 0 0 0 0 40 0 40 -- (B) 60 0
-- 40 -- -- 70 -- 70 (C) 60 0 0 0 0 0 0 0 0 (D) 60 0 -- -- -- -- --
-- 0 (E) 60 0 60 20 70 0 20 -- 30 (F) 60 10 -- 70 70 90 70 70 80
(I)-Na- 60 0 70 80 70 90 90 100 90 salt
TABLE-US-00004 TABLE B2 Post-emergence test/greenhouse Active
Application rate compounds (g ai./ha) Alopecurus Avena Setaria (G)
250 30 0 30 (H) 250 40 80 20 (I)-Na-salt 125 90 90 95
EXAMPLE C
[0056] Post-Emergence Tests/Outdoors
[0057] In addition to the comparative compounds (B) and (D), the
sodium salt of the compound of the formula (I) was tested under
outdoor conditions in the main cultivation areas of summer wheat in
Canada against economically important weeds. The small-plot
experiments were carried out on cultivated land under agricultural
use. Areas with particularly extensive weed growth were chosen
preferably.
[0058] The active compounds were applied across the area by the
spray method, with an average droplet size. To produce a useful
preparation of active compound, the active compounds were
formulated as 70 WP (70% w/w water-dispersible powder) and applied
with customary amounts of water. Wetting of the plants was improved
by addition of a surface-active substance (SAS) in the
concentrations recommended by the respective manufacturer.
[0059] To assess the crop compatibility, from 1 to 8 weeks after
the treatment, plant growth inhibitions or ailing of the leaf area
were assessed in % damage in comparison to the development of the
untreated control. At different intervals after the treatment, the
herbicidal activity was assessed as % reduction in comparison to
the untreated control, based on the weed development. The figures
denote: [0060] 0%=no damage of the crops or no herbicidal effect,
[0061] 100%=total destruction of the crops or the weeds.
[0062] The tests that were carried out show that the sodium salt of
the compound of the formula (I) has considerably stronger activity
against Avena fatua than the comparative compounds (B) and (D),
combined with approximately the same compatibility.
["% w/w"=percentage by weight]
TABLE-US-00005 TABLE C Post-emergence tests/outdoors herbicidal
effect herbicidal effect herbicidal effect (%) (%) (%) (I)-Na-salt
+ Number (B) + SAS (D) + SAS SAS Test plants of tests (30 g of
a.i./ha) (15 g of a.i./ha) (30 g of a.i./ha) Avena fatua 6 69 65 88
Setaria viridis 5 95 81 94 Fallopia convolvulus 5 71 70 73 Sinapis
arvensis 5 97 95 94 Thlaspi arvense 3 97 95 93 Crop damage 9 5 12 6
(wheat) SAS = "Canplus 411" (commercial product)
EXAMPLE D
[0063] Post-Emergence Tests/Outdoors
[0064] The sodium salt of the compound of the formula (I) was
tested under outdoor conditions in the main cultivation areas of
summer wheat in Canada and the USA against economically important
weeds. The small-plot experiments were carried out on cultivated
land under agricultural use, with cultivation and climate
conditions which can be considered to be representative for the
period of the trial. Areas with particularly extensive weed growth
were chosen by way of preference.
[0065] The active compound was applied across the area by the spray
method, with an average droplet size. To produce a useful
preparation of active compound, the active compound was formulated
as 70 WP or 70 WG (70% w/w water-dispersible powder or granules)
and applied with customary amounts of water. Wetting of the plants
was improved by addition of a surface-active substance (SAS) in the
concentration recommended by the manufacturer.
[0066] To assess the crop compatibility, from 1 to 8 weeks after
the treatment, plant growth inhibitions or ailing of the leaf area
were assessed in % damage in comparison to the development of the
untreated control. At different intervals after the treatment, the
herbicidal activity was assessed as % reduction in comparison to
the untreated control, based on the weed development. The figures
denote: [0067] 0%=no damage of the crops or no herbicidal effect,
[0068] 100%=total destruction of the crops or the weeds.
[0069] The tests that were carried out show that the sodium salt of
the compound of the formula (I) is particularly suitable for
controlling Avena fatua, Setaria viridis, Amaranthus retroflexus,
Brassica spp., Capsella bursa-pastoris, Sinapis arvensis and
Thlaspi arvense in cereals.
TABLE-US-00006 TABLE D Post-emergence tests/outdoors (I)-Na-salt +
SAS (28-30 g of a.i./ha) herbicidal effect Test plants Number of
tests (%) Avena fatua 263 90 Setaria viridis 102 94 Amaranthus
retroflexus 60 90 Brassica spp. 27 93 Capsella bursa-pastoris 12 90
Sinapis arvensis 48 98 Thlaspi arvense 45 97 Crop damage (wheat)
408 3 SAS = Agral, Agsurf, Canplus 411, X-77 (commercial
products)
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