Title of Invention

"METHOD FOR THE SELECTIVE CONTROL OF ONE OR MORE WEEDS"

Abstract The present invention relates to selective-herbicidal compositions, characterized in that they contain an effective amount of the compound 2-(2-methoxycarbonyl-phenylsulphonylaminocarbonyl)-4-methyl-5-propoxy-2,4-dihydro-3H-l,2,4-triazol-3-one of the formula (I) 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.
Full Text The present invention relates to a method for the selective control of one or more weeds.
Selective herbicides based on a substituted phenylsulphonvlaminocarbonyI-triazolinone
The invention relates to the use of the known compound 2-(2-methoxycarbonyl-phenylsulphonylaminocarbonyl)-4-methyl-5-propoxy-2J4-dihydro-3H-l,2,4-triazol-3-one of the formula (I) shown below - alias methyl 2-[[[(4,5-dihydro-4-methyl-5-oxo-S-propoxy-lH-l^^-triazol-l-yl)-carbonyll-aminol-sulphonyll-benzoate (CAS-Reg.-No.: 145026-81-9) - and its salts, in particular its sodium salt (CAS-Reg.-No. 181274-15-7), for the selective control of weeds in crops of useful plants, in particular for controlling problematic weeds in cereals.
Substituted phenylsulphonylaminocarbonyltriazoh'nones such as, for example, the
compounds 2-(2-methoxycarbonyl-phenylsulphonylaminocarbonyl)-4-methyl-
5-butoxy-2,4-dihydro-3H-1,2,4-triazol-3-one, 2-(2-methoxycarbonyl-phenyl-
sulphonylaminocarbonyl)-4-methyl-5-ethoxy-2,4-dihydro-3H-l,2,4-tria2ol-3-one, 2-(2-methoxycarbonyl-phenylsulphonylaminocarbonyl)-4-methyl-5-isopropoxy-2,4-dihydro-3H-1,2,4-triazol-3-one, 2-(2-ethoxycarbonyl-phenylsulphonylamino-carbonyl)-4-methyl-5-propoxy-2,4-dihydro-3H-1,2,4-triazol-3-one, 2-(2-memoxy-carbonyl-phenylsulphonylaminocarbonyl)-4-propoxy-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one and 2-(2-methoxycarbonyl-phenylsulphonylaminocarbonyl)-4-ethyl-5-propoxy-2,4-dihydro-3H-l,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-422469, EP-507 171, US-5 534486). 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.


Surprisingly, it has now been found that the compound 2-(2-methoxycarbonylphenylsulphonylaminocarbonyl)-
4-methyl-5-propoxy-2,4-dihydro-3H-l,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.
The invention provides selective-herbicidal compositions, characterized in that they
contain an effective amount of the compound 2-(2-methoxycarbonyl-phenylsulphonylaminocarbonyl)-
4-methyl-5-propoxy-2,4-dihydro-3H- 1 ,2,4-triazol-3-one of
the formula (I)
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].
The invention furthermore provides the use of the compound 2-(2-methoxycarbonylphenylsulphonylaminocarbonyl)-
4-methyl-5-propoxy-2,4-dihydro-3H-l,2,4-triazol-
3-one of the formula (I) 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.
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-methoxycarbonyl-phenylsulphonylaminocarbonyl)-4-methyl-
5-propoxy-2,4-dihydro-3H-l,2,4-triazol-3-one of the formula (I) 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.
The compound of the formula (I) and its Na salt are already known (cf. US-5 534 486
- Examples 72 and 320).
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:
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, Linderaia, Lamium,
Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium,
Ranunculus, Taraxacum.
Monocotvledonous weeds of the orders: Echinochloa, Setaria, Panicum, Digitaria,
Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Brornus, Avena, Cyperus,
Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis,
Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus,
Apera, Aegilops, Phalaris.
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.
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.
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, Bromus, Capsella, Erysimum, Lolium, Phalaris, Poa, Setaria, Sinapis
and Thlaspi.
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.
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.
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: aromatic
hydrocarbons, 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, 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 dimethylfbrmamide and dimethyl
sulphoxide, and also water.
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.
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.
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.
The formulations in general contain between 0.1 and 95 per cent by weight of active
compound, preferably between 0.5 and 90%.
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.
Possible components for the mixtures are known herbicides, for example
amidosulfuron, bentazon, bromoxynil, carfentrazone(-ethyl), cinidon(-ethyl), clodinafop(-
propargyl), clopyralid, chlorsulfuron, chlortoluron, cyclosulfamuron, 2,4-D,
diclofop(-methyl), difenzoquat, diflufenican, floransulam, 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.
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.
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 readyto-
use solutions, suspensions, emulsions, powders, pastes and granules. They are used
in the customary manner, for example by watering, spraying, atomizing or scattering.
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.
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.
The use of the compound of the formula (I) and its salts can be seen from the following
examples.
Use Examples:
The compounds listed below are used as comparative substances in the use examples:
2-(2-Methoxycarbonyl-phenylsulphonylaminocarbonyl)-4-methyl-5-butoxy-2,4-dihydro-
3H-l,2,4-triazol-3-one (known from EP-507 171, US-5 534 486 - Example 40)
2-(2-Methoxycarbonyl-phenylsulphonylaminocarbonyl)-4-methyl-5-ethoxy-2,4-
dihydro-3H-l,2,4-triazol-3-one - sodium salt (known from US-5 534 486 - Example
185)
2-(2-Methoxycarbonyl-phenylsulphonylaminocarbonyl)-4-methyl-5-isopropoxy-
2,4-dihydro-3H-l,2,4-triazol-3-one - sodium salt (known from US-5534486
Example 259)
0-C3H7-n
2-(2-Ethoxycarbonyl-phenylsulphonylaminocarbonyl)-4-methyl-5-propoxy-2,4-dihydro-
3H-l,2,4-triazol-3-one (in the claim of EP-507 171 and US-5 534 486)
2-(2-Methoxycarbonyl-phenylsulphonylaminocarbonyl)-4-propoxy-5-methyl-2,4-dihydro-
3H-l,2,4-triazol-3-one (in the claim of EP-341 489 and EP-422 469 and also
US-5 057 144)
2-(2-Methoxycarbonyl-phenylsulphonylaminocarbonyl)-4-ethyl-5-propoxy-2,4-dihydro-
3H-l,2,4-triazol-3-one (in the claim of EP-507 171 and US-5 534 486)
Example A
Post-emergence test/greenhouse
Solvent: 5 parts by weight of acetoneEmulsifier: 1 part by weight of alkylaryl polyglycol ether
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.
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 5001 of water/ha.
After three weeks, the degree of damage to the plants is assessed in % damage in
comparison to the development of the untreated control.
The figures denote:
0% = no effect (like untreated control)
100 % = total destruction
In this test, for example, the sodium salt of the compound of the formula (I) exhibits,
at an application rate of 60 g/ha, very strong activity (efficacy 80% to 100%) against
weeds, such as, for example, Agropyron, Alopecurus, Avena, Bromus and Lolium,
combined with very good compatibility with crop plants, such as, for example,
wheat, whereas the comparative compounds (A), (C), (D), (E) and (F) have
considerably weaker herbicidal activity and the comparative compounds (B) and (F)
are not entirely compatible with wheat, ["ai." = "active ingredient"].
Example B
Pre-emergence test/greenhouse
Solvent: 5 parts by weight of acetone
Emulsifier: 1 part by weight of alkylaryl polyglycol ether
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.
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 litres of water per hectare.
After three weeks, the degree of damage to the plants is tested in % damage in
comparison to the development of the untreated control.
The figures denote:
0% = no effect (like untreated control)
100% = total destruction
In this test, for example, the sodium salt of the compound of the formula (I) exhibits,
at application rates of from 15 g/ha to 60 g/ha, very strong activity (efficacy 80% to
100%) against weeds, such as, for example, Agropyron, Alopecurus, Avena, Bromus,
Lolium, Poa, Setaria and Sinapis, 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
Example C
Post emergence tests/outdoors
Under outdoor conditions, the sodium salt of the compound of the formula (I) was
tested in winter wheat in Germany and France 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.
The active compound was applied by the post-emergence method (spring) 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.
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:
0% = no damage of the crops or no herbicidal effect,
100% = total destruction of the crops or the weeds.
The experiments which were carried out show that the sodium salt of the compound
of the formula (I) is particularly suitable for controlling the perennial species
Agropyron repens, which is difficult to control, and the annual species Alopecurus
myosuroides, Apera spica-venti, Capsella bursa-pastoris and Sinapis arvensis in
cereals.
["% w/w" = per cent by weight]
Table C
Post-emergence tests/outdoors
Test plants Number of tests
(I)-Na-salt
(42 g of a.i./ha to 45 g of
a.i./ha)
herbicidal effect
Agropyron repens 83 89
Alopecurus myosuroides 204 91
Apera spica-venti 87 94
Poa annua 67
Capsella bursa-pastoris 100
Sinapis arvensis 100
Damage to the crop (wheat) 439
Example D
Post-emergence tests/outdoors
The sodium salt of the compound of the formula (I) was tested under outdoor
conditions in the main cultivation areas of winter wheat in the USA (Pacific
Northwest, North Central Area, Central Plains) against economically important
weeds. The design, the practice and the evaluation of the experiments corresponded
to Example C. The active compound was applied in autumn. Wetting of the plants
was improved by addition of commercial surface-active substances (SAS) in the
concentrations recommended by the respective manufacturer.
The tests show that the sodium salt of the compound of the formula (I) is particularly
suitable for controlling Bromus species, Erysimum cheiranthoides and Thlaspi
arvense in cereals.
Post-emergence tests/outdoors
Test plants
Bromus secalinus
Bromus tectorum
Erysimum cheiranthoides
Thlaspi arvense
Damage to the crop (wheat)
Post-emergence tests/outdoors
The sodium salt of the compound of the formula (I) was tested under outdoor
conditions in an irrigation wheat growing area of the USA (California) against
economically important weeds. The design, the practice and the evaluation of the
tests corresponded to Example D.
The tests which were carried out show that the sodium salt of the compound of the
formula (I) is particularly suitable for controlling Phalaris species in cereals.
Table E
Post-emergence test/outdoors
Test plants
Phalaris minor
Phalaris paradoxa
Damage to the crop (wheat)
Number of tests

WE CLAIM:
1. Method for the selective control of one o'r more weeds selected from the
group consisting of agropyron, alopecurus, amaranthus, avena, capsalla,
erysimum, lollum, phalaris, poa, setarla, sinapis and thlaspi in crops of
cereals, characterized in that the compound 2-(2-
methoxycarbonylphenylsulfonylaminocarbonyl)-4-methyl-5-propoxy- 2,4-
dihydro-3H-l,2,4-triazol-3-on and/or the salts of this compound are applied in
the crops of cereals.
2. Method as claimed in claim 1, wherein the crop of cereals is wheat.
3. Method as claimed in claim 1 or 2, wherein the weeds are selected from
the group consisting of agropyron, alopecurus, avena, lollum, poa, setaria and
sinapis.
4. Method as claimed in claim 1 or 2, wherein the weed is an alopecurus
species.
5. Method as claimed in claim 1 or 2, wherein the weed is an agropyron
species.
6. Method as claimed in any of claims 1 to 5, wherein the compound 2-(2-
methoxycarbonyl-phenylsulfonylaminocarbonyl)-4-methyl-5-propoxy-2,4-
dihydro-3H-l,2,4-triazol-3-on and/or its salts is/are applied in an application
rate of 15 to 60 g/ha.
7. Process as claimed in claim 1, wherein the weed is alopecurus and the
crop of cereals is winter wheat.
8. Method as claimed in claim 1, wherein the weed is agropyron and the
crop of cereals is winter wheat.

9. Method as claimed in claim 7 or 8, wherein the 2-(2-methoxycarbonyl-
phenylsulfonylaminocarbonyl)-4-methyl-5-propoxy-2,4-dihydro-3H-1,2,4-
triazol-3-on and/or the salts of this compound is/are applied as a 70 wp or 70
wg formulation.
10. The compound 2-(2-methoxycarbonyl-phenylsulfonylaminocarbonyl)-4-
methyl-5-propoxy-2,4-dihydro-3H-l,2,4-triazol-3-on and/or its salts for use in
one of the methods as claimed in claims 1 to 9.
11. The method for the selective control of one or more weeds as claimed in
claims 1 to 3 substantially as herein described with reference to the foregoing
examples.



Documents:

1202-del-1999-abstract.pdf

1202-DEL-1999-Claims-30-04-2008.pdf

1202-del-1999-claims.pdf

1202-DEL-1999-Correspondence-Others-(17-03-2011).pdf

1202-DEL-1999-Correspondence-Others-30-04-2008.pdf

1202-del-1999-correspondence-others.pdf

1202-del-1999-description (complete)-30-04-2008.pdf

1202-del-1999-description (complete).pdf

1202-DEL-1999-Form-1-30-04-2008.pdf

1202-del-1999-form-1.pdf

1202-del-1999-form-18.pdf

1202-DEL-1999-Form-2-30-04-2008.pdf

1202-del-1999-form-2.pdf

1202-DEL-1999-Form-27-(17-03-2011).pdf

1202-DEL-1999-Form-3-30-04-2008.pdf

1202-del-1999-form-3.pdf

1202-del-1999-form-5.pdf

1202-DEL-1999-GPA-30-04-2008.pdf

1202-del-1999-gpa.pdf

1202-DEL-1999-Petition-137-30-04-2008.pdf

1202-DEL-1999-Petition-138-30-04-2008.pdf

abstract.jpg


Patent Number 220761
Indian Patent Application Number 1202/DEL/1999
PG Journal Number 30/2008
Publication Date 25-Jul-2008
Grant Date 04-Jun-2008
Date of Filing 08-Sep-1999
Name of Patentee BAYER AKTIENGESELLSCHAFT
Applicant Address
Inventors:
# Inventor's Name Inventor's Address
1 PETER DAHMEN
2 HANS-JOACHIM SANTEL
3 INGO WETCHOLOWSKY
4 DIETER FEUCHT
5 KLAUS LURSSEN
6 KLAUS-HELMUT MULLER
PCT International Classification Number A01N 27/00
PCT International Application Number N/A
PCT International Filing date
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 198 45 408.2 1998-10-02 Germany