Title of Invention

HERBICIDAL COMPOSITION

Abstract The present invention relates to a Liquid herbicidal composition, containing a grass herbicide that is suspended or dissolved in a non-aqueous liquid phase, a herbicide of the sulfonylurea type that is suspended in a non- aqueous liquid phase, and at least one surface-active substance.
Full Text Herbicidal composition
The present invention relates to a new liquid herbicidal composition, the preparation thereof, as well as the use of the composition in the control of undesired plant growth in crops of cultivated plants.
According to the present invention, a liquid herbicidal composition is proposed, which contains, in addition to customary formulation excipients, (a) at least one grass herbicide that is suspended or dissolved in a non-aqueous liquid phase, (b) at least one herbicide of the sulfonylurea type that is suspended in a non-aqueous liquid phase, and (c) at least one non-ionic or anionic, surface-active substance or a mixture of the non-ionic and anionic substances.
Grass herbicides which may be used in accordance with the Invention belong especially to the chemical classes of acetanilides, phenoxypropionic acids, pyrimidinyloxybenzoic acids, phenylsulfonyltriazoles, oxyacetamides, oxazolidindiones, phenylbenzamides, pyrimidinyl thiophthalides and indanes, and are preferably pretilachlor, cyhalofop, pyriminobac, cafenstrole, mefenacet, fentrazamid, oxaziclomefon, pentoxazone, etobenzanid, indanofan as well as epoprodan and the compound of formula I

These grass herbicides may also be used in a mixture together. They exist in dissolved or dispersed form in a non-aqueous liquid phase. The herbicides of the sulfonylurea type are also dispersed in preferably the same non-aqueous liquid phase. These are preferably cinosulfuron, pyrazosulfuron, bensulfuron, azimsulfuron, imazosulfuron, ethoxysulfuron, cyclosulfamuron or halosulfuron or mixtures thereof.
The preferred non-aqueous liquid phases include all vegetable and mineral oils, such as rapeseed oil, soybean oil, sunflower oil, castor oil, pine oil, cottonseed oil, as well as

derivatives of these oils, for example esters, especially methylesters of these oils, as well as paraffinic and aromatic mineral oils, such as Orchex 796, Shellsol types, Isopar types, aromatic fractions, such as Solvesso 200 and esters such as Exxate 700, as well as mixtures thereof.
The non-ionic and anionic surface-active substances may be conventional, commercially available substances, for example ethoxylated vegetable oils such as Emulsogen EL, ethoxylated fat alcohols such as Genapol O-050, ethoxylated alkylphenols such as Synperonic NP8, ethoxylated polyethylene glycols or polypropylene glycols, e.g. Pluronic types, ethoxylated tristyrylphenol derivatives such as Soprophor 4D384 or Soprophor S/25, oleyl polyglycol ethers such as Genapol U-050, and silicone surfactants such as Silwet L77, as well as dodecylbenzene sulfonates such as Sermul 88A, alcohol ether sulfonates such as Genapol LRO, lignin sulfonates such as Ultrazln NA, phenol sulfonates such as Sipragil GN and polycarboxylates such as Geropon TA72, sulfonated naphthalene/formaldehyde condensates such as Supragil MSN, sulfosuccinates such as Aerosol OT 70 PG, polyacrylate derivatives such as Atlox 4913, maleic acid/olefin copolymers such as Sokolan CP9, alkyl polyglycosides, alkyl succinic acid anhydride derivatives, sorbitan esters, ethoxylated sorbitan esters, alkyl and alkylaryt polyglycol ether phosphoric acid esters and ethoxylated fatty acid esters, as well as taurides such as Hostapon T hk.
The above-mentioned herbicides are described in the Pesticide Manual, Eleventh Edition, British Crop Protection Council, 1997. The compound of formula I is known from EP-A-447506, fentrazamid from British Crop Protection Conference Proceedings, 1997, 67-72, and oxaziclomefon from British Crop Protection Conference Proceedings, 1997,73-80.
Preferred herbicidal compositions according to the present invention contain as the grass herbicide cyhalofop, pyriminobac, cafenstrole, mefenacet, fentrazamid, oxaziclomefon, pentoxazone, etobenzanid, indanofan, epoprodan, pretilachlor or a compound of formula I


As the herbicide of the sulfonylurea type, the compositions according to the invention preferably contain pyrazosulfuron, bensulfuron, azimsulfuron, imazosulfuron, ethoxysulfuron, cyclosulfamuron, halosulfuron or cinosulfuron or mixtures thereof.
The non-aqueous liquid phases to be used are preferably mineral oils or vegetable oils, or also mixtures thereof. The preferred non-ionic, surface-active substances that may be considered are ethoxylated vegetable oil, ethoxylated fat alcohol, ethoxylated alkylphenol, ethoxylated polyethylene glycol and polypropylene glycol and copolymers thereof, ethoxylated tristyrylphenol derivative, oleyl polyglycol ether or silicone surfactant, and the anionic surface-active substance may be a dodecylbenzene sulfonate, sulfosuccinate, ethoxylated tristyrylphenol sulfate or phosphate, alcohol ether sulfonate, lignin sulfonate, ethoxylated phenol sulfonate or polycarboxylate.
A significant composition is one which contains as the grass herbicide pretilachlor or the compound of formula I or a mixture thereof suspended or dissolved in a vegetable oil, as the herbicide of the sulfonylurea type bensulfuron, pyrazosulfuron, azimsulfuron, imazosulfuron or cinosulfuron or mixtures thereof suspended in a vegetable oil, and as the surface-active substance a mixture of non-ionic and anionic compounds. Of these, preference is given to a composition which contains as the grass herbicide the compound of formula I suspended or dissolved in a vegetable oil, as the herbicide of the sulfonylurea type cinosulfuron suspended in a vegetable oil, and as the surface-active substance a mixture of non-ionic and anionic compounds. Of these, further preference is given to a composition which contains as the grass herbicide pretilachlor suspended or dissolved in a vegetable oil, as the heribicide of the sulfonylurea type cinosulfuron suspended in a

vegetable oil, and as the surface-active substance a mixture of non-ionic and anionic compounds.
An especially effective composition contains as the grass herbicide pretilachlor or the compound of formula I or a mixture thereof, preferably the compound of formula I alone, suspended or dissolved in rapeseed oil or rapeseed oil methyl ester or in a mixture thereof, as the herbicide of the sulfonylurea type bensulfuron suspended in rapeseed oil or rapeseed oil methyl ester or in a mixture thereof, and as the surface-active substance a mixture of a non-ionic with an anionic compound selected from castor oil ethoxylate, dodecylbenzene sulfonate, ethoxylated tristyrylphenol sulfate and oleyl polyglycol ether.
The compositions according to the invention have the great advantage that they may contain the herbicidal active ingredients in high concentrations, and that they remain protected from decomposition over a longer period of time. They also offer the possibility that other oil-soluble or liquid admixtures may be added without problems, such as additives that are suitable for increasing the biological activity, as well as stabilisers such as epoxidised vegetable oils. Surprisingly, the compositions according to the invention show practically no damage to the crops of cultivated plants after their application, despite using organic liquids.
The compositions according to the invention are preferably suitable for the control of weeds in flooded paddy fields. The process is advantageously carried out in such a way that the required amount of composition is mixed with the same amount or up to ten times the amount of water, and applied directly to the already flooded paddy field, or is added to the water flowing in during flooding of the paddy field (so-called splash application). Furthermore, it is also possible, to apply the composition dropwise or in portions simultaneously with the mechanical planting of the rice plants (so-called dip application). Spray application of the composition according to the invention is similarly possible, but requires a higher dilution with water.
The application rates of composition according to the invention may vary within a wide range. It is preferable to use 50 to 2000 g/ha herbicide (grass herbicide plus herbicide of the sulfonylurea type).

The liquid compositions according to the invention contain per litre preferably 30 to 1920 g grass herbicide and 20 to 80 g herbicide of the sulfonylurea type, as well as 50 to 300 g of surface-active substance (anionic plus non-ionic). Normally, 2 - 20 I/ha of the formulations described below by way of example are required for direct application or for splash application. For spray application, this amount Is usually 20 - 500 I/ha. The compositions according to the invention may also contain further customary additives, for example inert carriers such as kaolin and chalk, stabilisers, anti-foaming agents, presen/atives, viscosity regulators, thickeners such as silicic acid or bentonite, binders, tackif iers, as well as fertilisers or other active ingredients. The compositions are produced in known manner, e.g. by intimately mixing and/or grinding the active ingredients with the formulation excipients and with liquid or solid carriers. Particularly preferred formulations are made up as follows:


Compound of formula 1 active ingredient 180
pretilachlor Rifit, Solnet active ingredient 180
bensulfuron methyl Londax active ingredient 51
ethoxylated tristyrylphenol Soprophor 4D384 surface-active 20
sulfate substance
dodecylbenzene sulfonate Sermul EA88 surface-active substance 40
oleyl polyglycol ether Genapol U-050 surface-active substance 90
mineral oil Orchex 796 non-aqueous liquid remainder
phase to make up 1 1
F3:

Compound of formula 1 active ingredient 180
pretilachlor Rifit, Solnet active ingredient 180
bensulfuron methyl Londax active ingredient 51
ethoxylated tristyrylphenol Soprophor 4D384 surface-active 20
sulfate substance
dodecylbenzene sulfonate Sermul EA88 surface-active substance 50
castor oil ethoxylate 18E0 Alkamuls R/81 surface-active substance 80
rapeseed oil methyl ester Edenor ME-SU non-aqueous liquid remainder
phase to make up 1 1

F4:

Compound of formula 1 active ingredient 180
pretilachlor RIfit, Solnet active ingredient 180
bensulfuron methyl Londax active ingredient 51
castor oil derivative Marlowet LVS surface-active substance 150
rapeseed oil non-aqueous liquid remainder
phase to make up 1 1
F5:

Compound of formula 1 active ingredient 180
pretilachlor Rifit, Solnet active ingredient 180
bensulfuron methyl Londax active ingredient 30
azimsulfuron Gulliver active ingredient 6
dodecylbenzene sulfonate Sermul EA88 surface-active substance 50
castor oil ethoxylate Sermul EN24 surface-active substance 50
silicic acid Aerosil 200 thickener 20
rapeseed oil non-aqueous liquid phase 234
rapeseed oil methyl ester Agrimul 2232 F non-aqueous liquid remainder
phase to make up 1 1
F6:

Compound of formula pretilachlor

Rifit, Solnet

active Ingredient active ingredient

180 180

bensulfuron methyl Londax active ingredient 30
azimsulfuron Gulliver active ingredient 6
dodecylbenzene sulfonate Sermul EA88 surface-active substance 65
castor oil ethoxylate Semul EN24 surface-active substance 65
tristyrylphenol ethoxylate Soprophor BSD surface-active substance 20
silicic acid Aerosll 200 thickener 30
rapeseed oil non-aqueous liquid phase 174
rapeseed oil methyl ester Agrimul 2232 F non-aqueous liquid remainder
phase to make up 1 1
F7:

Compound of formula 1 active ingredient 180
cinosulfuron Setoff active ingredient 24
ethoxylated tristyrylphenol Soprophor 4D384 surface-active 20
sulfate substance
castor oil ethoxylate Sermul EN24 surface-active substance 40
dodecylbenzene sulfonate Sermul EA88 surface-active substance 40
silicic acid Aerosil 200 thickener 40
rapeseed oil methyl ester Agrimul 2232 F non-aqueous liquid remainder
phase to make up 1 1
F8:

Compound of formula

active ingredient

180

cinosulfuron Setoff active ingredient 24
ethoxyiated tristyrylphenol Soprophor 4D384 surface-active 20
sulfate substance
castor oil ethoxylate Sermul EN24 surface-active substance 65
dodecylbenzene sulfonate Sermul EA88 surface-active substance 65
silicic acid Aerosil 200 thickener 40
aluminium silicate Attagel 50 inert carrier 30
rapeseed oil methyl ester Agrimul 2232 F non-aqueous liquid remainder
phase to make up 1 1
F9:

pretilachlor Rifit active ingredient 450
cinosulfuron Setoff active ingredient 24
ethoxyiated tristyrylphenol Soprophor 4D384 surface-active 20
sulfate substance
castor oil ethoxylate Sermul EN24 surface-active substance 60
dodecylbenzene sulfonate Semiul EA88 surface-active substance 60
aluminium silicate Kaolin inert carrier 250
silicic acid Aerosil 200 thickener 30
rapeseed oil methyl ester Agrimul 2232 F non-aqueous liquid remainder
phase to make up 1 1
F10:

pretilachlor cinosulfuron

Rifit Setoff

active ingredient active ingredient

450 24

ethoxylated tristyrylphenol Soprophor 4D384 surface-active 20
sulfate substance
castor oil ethoxylate Sermul EN24 surface-active substance 60
dodecylbenzene sulfonate Senmul EA88 surface-active substance 60
aluminium silicate Kaolin inert carrier 200
silicic acid Aerosil 200 thickener 30
rapeseed oil methyl ester Agrimul 2232 F non-aqueous liquid remainder
phase to make up 1 1
Application examples
Formulations F1, F2, F3, F4, F5, F6, F7, F8, F9 and F10 are diluted with water to 5 litres, and introduced directly to a flooded paddy field at an application rate of 5 I/ha (splash application). 22 days after application, control of the weeds Echlnochloa, Scirpus and Monochoria is investigated, as well as the phytotoxic activity of the compositions on rice (100% indicates complete control of the weeds or completely withered rice, 0% indicates no control of the weeds or no phytotoxic activity on the rice). This takes place in tests running in parallel: a) upon emergence, b) at the 2.5 leaf stage and c) at the 4.1 leaf stage of Echlnochloa. The results obtained In these tests are summarised in the following Table:

Formulation
F1
F2


% weed control
% phytotoxic activity
a) b) c)
rice 0 5 11
Echlnochloa 99 96 95
Scirpus 98 92 94
Monochoria 100 95 95
rice 0 7 9
Echlnochloa 99 98 92

Scirpus 98 94 94
Monochoria 100 94 93
F3 rice 3 8 9
Echinochloa 100 95 93
Scirpus 99 90 95
Monochoria 100 89 96
% weed control
Formulation % phytotoxic activity
a) b)
F5 rice 0 0
Echinochloa 100 70
Scirpus 90 80
Monochoria 95 90
F6 rice 0 0
Echinochloa 100 80
Scirpus 90 80
Monochoria 98 90
F7 rice 0 0
Echinochloa 98 70
Scirpus 70 80
Monochoria 90 90
F8 rice 0 0
Echinochloa 98 70
Scirpus 70 90
Monochoria 95 90
F9 rice 0 0
Echinochloa 100 20
Scirpus 98 90
Monochoria 100 95
F10 rice 0 0
Echinochloa 100 10
Scirpus 95 90

Monochoria 100 90
The same results are obtained if these formulations are diluted with water, e.g. to 2 - 5001.


WE CLAIM:
1. Liquid herbicidal composition, containing
(a) at least one grass herbicide that is suspended or dissolved in a non-aqueous
liquid phase, said grass herbicide comprising at least one member selected from
the group consisting of cyhalofop, pyriminobac, cafenstrole, mefenacet,
fentrazamid, oxaziclomefon, pentoxazone, indanofan, epoprodan, pretilachlor
or a compound of formula I

or a mixture thereof,
(b) at least one herbicide of the sulfonylurea type that is suspended in a non┬Čaqueous liquid phase, and
(c) at least one non-ionic or anionic, surface-active substance or a mixture of the non-ionic and anionic surface-active substances.

2. The composition as claimed in claim 1, containing as the herbicide of the sulfonylurea type pyrazosulfuron, bensulfuron, azimsulfuron, imazosulfuron, ethoxysulfuron, cyclosulfamuron, halosulfuron or cinosulfuron or a mixture thereof
3. The composition as claimed in claim 1, containing as non-aqueous liquid phase a vegetable or mineral oil or a mixture of these oils.
4. The composition as claimed in claim 1, containing as the non-ionic, surface-
active substance, an ethoxylated vegetable oil, ethoxylated fat alcohol,

ethoxylated alkylphenol, ethoxylated polyethylene glycol or propylene glycol or copolymers thereof, ethoxylated tristyrylphenol derivative, oleyl polyglycol ether or silicone surfactant, or as the anionic surface-active substance, a dodecylbenzene sulfonate, sulfosuccinate, ethoxylated tristyrylphenol sulfate or phosphate, alcohol ether sulfonate, lignin sulfonate, ethoxylated phenol sulfate or polycarboxylate or a mixture of these non-ionic and anionic, surface-active compounds.
5. The composition as claimed in claim 1, containing as the grass herbicide pretilachlor or the compound of formula I or a mixture thereof suspended or dissolved in a vegetable oil, as the herbicide of the sulfonylurea type bensulfuron, pyrazosulfuron, azimsulfuron, imazosulfuron or cinosulfuron or mixtures thereof suspended in a vegetable oil, and as the surface-active substance a mixture of non-ionic and anionic compounds.
6. The composition as claimed in claim 5, containing as the grass herbicide the compound of formula I and as the herbicide of the sulfonylurea type cinosulfuron.
7. The composition as claimed in claim 5, containing as the grass herbicide pretilachior and as the herbicide of the sulfonylurea type cinosulfuron.
8. The composition as claimed in claim 5, containing as the grass herbicide pretilachior or the compound of formula I or a mixture thereof, suspended or dissolved in rapeseed oil or rapeseed oil methyl ester or in a mixture thereof, as the herbicide of the sulfonylurea type bensulfuron suspended in rapeseed oil or rapeseed oil methyl ester or in a mixture thereof, and as the surface-active substance a mixture of a non-ionic with an anionic compound selected from castor oil ethoxylate, dodecylbenzene sulfonate, ethoxylated tristyrylphenol sulfate and oleyl polyglycol ether.
9. The composition as claimed in claim 8, containing as the grass herbicide the compound of formula I.
10. A method for controlling undesired plant growth in rice crops said method comprising direct application of the composition as claimed in claim 1,

to already flooded paddy fields, to paddy fields that are just being flooded, or during planting of the rice plants.

Documents:

in-pct-2001-0596-che abstract duplicate.pdf

in-pct-2001-0596-che abstract.pdf

in-pct-2001-0596-che claims duplicate.pdf

in-pct-2001-0596-che claims.pdf

in-pct-2001-0596-che correspondence others.pdf

in-pct-2001-0596-che correspondence po.pdf

in-pct-2001-0596-che description (complete) duplicate.pdf

in-pct-2001-0596-che description (complete).pdf

in-pct-2001-0596-che form-1.pdf

in-pct-2001-0596-che form-19.pdf

in-pct-2001-0596-che form-26.pdf

in-pct-2001-0596-che form-3.pdf

in-pct-2001-0596-che form-4.pdf

in-pct-2001-0596-che form-5.pdf

in-pct-2001-0596-che pct.pdf

in-pct-2001-0596-che petition.pdf


Patent Number 202375
Indian Patent Application Number IN/PCT/2001/596/CHE
PG Journal Number 05/2007
Publication Date 02-Feb-2007
Grant Date 03-Oct-2006
Date of Filing 30-Apr-2001
Name of Patentee M/S.SYNGENTA PARTICIPATIONS AG
Applicant Address Schwarzwaldallee 215 CH-4058 Basel
Inventors:
# Inventor's Name Inventor's Address
1 KRUGER, Christian Talstrasse 21 D-79639 Grenzach-Wyhlen
2 ALLARD, Jean-Louis L'Orsastrasse 16 CH-4310 Rheinfelden
3 LABHART, Christoph Muspenacker 305 CH-4204 Himmelried
PCT International Classification Number A01N 25/04
PCT International Application Number PCT/EP1999/008359
PCT International Filing date 1999-11-02
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 2222/98 1998-11-04 Switzerland