Description:FORM 2

THE PATENTS ACT 1970
(SECTION 39 OF 1970)

&

THE PATENT RULES, 2003

COMPLETE SPECIFICATION
(Section 10 and Rule 13)

SUSPO EMULSION COMPOSITION OF SULFENTRAZONE, PENDIMETHALIN AND OXYFLUORFEN

We, COROMANDEL INTERNATIONAL LIMITED,
an Indian company incorporated under the Companies Act, 1956, and validly existing under the Companies Act, 2013. Having its registered office at Coromandel House, Sardar Patel Road,
Secunderabad – 500 003, Telangana, India

The following specification particularly describes the invention and the manner in which it is to be performed.

FIELD OF THE INVENTION

The present invention relates to a kind of synergistic herbicide composition that contains herbicidal active compounds, and it is suitable for preventing unwanted plants in the crops like soybean, paddy rice and sugarcane.

Particularly the present invention relates to a synergistic herbicidal composition comprising of sulfentrazone, pendimethalin and oxyfluorfen along with suitable agrochemical adjuvants.

BACKGROUND OF THE INVENTION

Herbicides are the most used method in our country and worldwide for the control of weed due to easy application, getting the results in a short time, having long lasting and powerful effect. They have nowadays increasingly become the most important and indispensable control method in agricultural production. They are used for a long time to increase the production of agricultural activities.

But the continued use of herbicides created many problems like weed resistance, shift weed in shift flora, and environment hazards. From this all-problems herbicide resistance is very serious problem in present time all over the world. The main reasons for resistance are lack of rotation of the herbicide and use of herbicides with long residue period. Herbicide resistance is a worldwide phenomenon and the number of resistant biotypes of weeds is increasing at an alarming rate. Currently there are 480 cases of herbicide resistance in 252 plant species. Herbicide resistance in weeds should be minimized because it is a major limiting factor of food security. A proper knowledge of development and mechanism of resistance would help us with its management. Herbicide resistance problems are controlled with integrated weed management practices, including crop and herbicide rotations, herbicide combinations, and cultural, mechanical, and biological methods of weed control.

Hence, there is always a need for new active ingredients or new combinations of existing active ingredients to overcome the existing problems faced in the agricultural industry. Compositions comprising a single herbicidally active component suffer from numerous drawbacks such as formation of resistant weeds, requirement of high amount and concentration of the active ingredient, environmental damage, seepage of the active component into ground water, phytotoxicity and harmful effects on the health of animals and humans.

Active compounds having different mechanisms of action are combined to delay the generation of resistance and reduce the amount of application and prevention and treatment costs. Consequently, research is being conducted to produce herbicides and combinations of herbicides that are safer, that have better performance, that require lower dosages, that are easier to use, and that cost less.

Sulfentrazone is a broad-spectrum herbicide and it acts by inhibiting the enzyme protoporphyrinogen oxidase in plants. PPO inhibitors at the herbicide site-of-action interfere with an enzyme involved in chlorophyll biosynthesis and lead to an accumulation of intermediates that are highly reactive when exposed to light resulting in membrane disruption.

It can be used both as pre-emergence and as a post emergence herbicide in the control of annual broadleaf weeds and yellow nutsedge in a variety of crops including soybeans, sunflowers, dry beans, and dry peas.

Pendimethalin is an herbicide of the dinitroaniline class used in preemergence and postemergence applications to control annual grasses and certain broadleaf weeds. It inhibits cell division and cell elongation for different crops including cereals (wheat, barley, rye, triticale), corn, soybeans, rice, potato, legumes, fruits, vegetables, nuts as well as lawns and ornamental plants and wheat, corn, soybeans, potatoes, cabbage, peas, carrots, and asparagus. It is used to control annual grasses and certain broadleaf weeds which interfere with growth, development, yield, and quality of agricultural and horticultural crops by competing on nutrients, water, and light.

Oxyfluorfen is a diphenyl-ether herbicide used for broad spectrum pre- and post-emergent control of annual broadleaf and grassy weeds in a variety of tree fruit, nut, vine, and field crops. The largest agricultural markets in terms of total pounds active ingredient are wine grapes and almonds. There are also non-agricultural ornamental and forestry uses. Oxyfluorfen is also used for weeding control in landscapes, patios, driveways, and similar areas in residential sites.

The synergistic herbicidal composition of the present invention can control a wide range of undesired plants emerging in agricultural fields or non-agricultural fields. It has a remarkable herbicidal activity when applied as sulfentrazone, pendimethalin and oxyfluorfen combination.

OBJECT OF THE INVENTION

In one object of the present invention is to provide a synergistic herbicidal composition suitable for preventing unwanted plants in crops like soybean, paddy rice and sugarcane.

In yet another object of the present invention is to provide a synergistic herbicidal composition comprising sulfentrazone, pendimethalin and oxyfluorfen in effective amounts, along with suitable agrochemical adjuvants.

In yet another object of the present invention is to provide synergistic, crop-selective herbicidal combination with broad-spectrum weed control.

In yet another object of the present invention is to provide a method for controlling undesired plants or inhibiting their growth, which comprises applying a herbicidally effective amount of the said composition to the undesired plants or to a place where they grow.

SUMMARY OF THE INVENTION

The present invention is to provide a synergistic herbicidal composition suitable for preventing unwanted plants in crops like soybean, paddy rice and sugarcane.

One aspect of the present invention provides a synergistic herbicidal composition comprising of a) sulfentrazone, b) pendimethalin, and c) oxyfluorfen with suitable agrochemical additives.

Another aspect of the present invention is to provide a synergistic herbicidal composition comprising of:
a) sulfentrazone in a range from 5% (w/w) to 15% (w/w);
b) pendimethalin in a range from 20% (w/w) to 30% (w/w);
c) oxyfluorfen present in a range from 0.5% (w/w) to 5% (w/w), and
d) agrochemical additives.

Another aspect of the present invention is to provide a Suspo emulsion (SE) composition comprising of:
a) sulfentrazone in a range from 5% (w/w) to 15% (w/w);
b) pendimethalin in a range from 20% (w/w) to 30% (w/w);
c) oxyfluorfen present in a range from 0.5% (w/w) to 5% (w/w), and
d) agrochemical additives.

In an aspect of the present invention, the suitable agrochemical additives are selected from a wetting agent, a dispersing agent, an anionic emulsifier, a non-ionic emulsifier, an antifreezing agent, a biocide, a defoamer, a rheology modifier, a solvent, and a filler.

In an aspect of the present invention, the wetting agent is selected from the group comprising of tristyrylphenol ethoxylate phosphate ester, polyoxyethylene polyoxypropylene condensate, polyoxyethylene alkyl ether, TERSEPERSE 2288, and cardphenol ethoxylate, present in a range from 1% to 5% (w/w).

In an aspect of the present invention, the dispersing agent is selected from the group comprising of anionic tristyrylphenol phosphate, tristyryl phenyl ether phosphate TEA salt, polymethyl methacrylate-polyethylene glycol graft copolymer, and ethoxylated alcohols (C12-16), present in a range from 1% to 5% (w/w).

In an aspect of the present invention, the anionic and non-ionic emulsifiers are selected from the group comprising of dodecylbenzene sulfonate, tristyrylphenol ethoxylate, IAL PA100, IAL PA200, alkoxylated alcohol and Ca-DDBS, castor oil ethylene oxide adduct, iso-C12 alkyl benzene sulfonate calcium salt, tristyrylphenol ethoxylate 16 mol EO, n-C12 alkyl benzene sulfonate calcium salt, castor oil based ethoxylate, 36 mol EO (EMULSOGEN EL 360), and combination thereof, present in a range from 1% to 10% (w/w).

In an aspect of the present invention, the antifreezing agent is propylene glycol, present in a range from 5% to 15% (w/w).

In an aspect of the present invention, the biocide is 1,2-benzisothiazalin-3-one, present in a range from 0.01% to 0.5% (w/w).

In an aspect of the present invention, the defoamer is silicone antifoam emulsion, present in a range from 0.1% to 2% (w/w).

In an aspect of the present invention, the rheology modifier is xanthan gum, present in a range from 5% to 10% (w/w).

In an aspect of the present invention, the solvent is selected form C9-aromatic hydrocarbons (or) solvent naphtha, (petroleum), light aromatic, present in a range from 15% to 20% (w/w).

In an aspect of the present invention, the filler is water, present in Q.S.

Yet another aspect of the present invention is to provide a process for the preparation of a Suspo emulsion (SE) composition comprising of sulfentrazone, pendimethalin, and oxyfluorfen.

In yet another aspect of the present invention provides an effective control of weeds especially grassy weeds, at application rates which are as low as possible, compositions which, at a reduced total amount of active compounds applied, have improved activity against the harmful weeds and a broadened activity spectrum, for certain indications.

In yet another aspect of the present invention is to provide a synergistic herbicidal composition, which can improve biological performance in single application and minimize occupational exposure and hazards.

In yet another aspect of the present invention is to provide a synergistic herbicidal composition, which demonstrates a high controlling effect with reduced environmental load and reduced cost in crop production as well as crop protection.

In yet another aspect of the present invention is to provide a synergistic herbicidal composition which can decrease the cost of application, save fuel cost, labor cost and therefore very economical.

The composition of the present invention decreases application rates of each of the active ingredients and is non-phytotoxic. Thus, it is effective to reduce the environmental load on an area where the composition is applied or a surrounding area thereof.

DESCRIPTION OF THE INVENTION

The term "comprising", which is synonymous with "including", "containing", or "characterized by” here is defined as being inclusive or open-ended, and does not exclude additional, unrecited elements or method steps, unless the context clearly requires otherwise.

It is to be noted that, as used in the specification, the singular forms "a", "an" and "the" include plural referents unless the context clearly dictates otherwise. Thus, for example, reference to a composition containing “a compound” includes a mixture of two or more compounds. It should also be noted that the term “or” is generally employed in its sense including “and/or” unless the content clearly dictates otherwise.

As used herein, the terms "crops" and "vegetation" can include, for instance, dormant seeds, germinant seeds, emerging seedlings, plants emerging from vegetative propagules, immature vegetation, and established vegetation.

As used herein, immature vegetation may be understood to include small vegetative plants prior to reproductive stage, and mature vegetation may be understood to include vegetative plants during and after the reproductive stage.

As used herein, the terms “herbicide” may be understood as a substance that is toxic to plants, used to destroy unwanted vegetation.

As used herein, the term “synergistic composition” may be understood to include effective combination of more than one agrochemical that allows the application of the said agrochemical in a much lower dosage, which results in a less dosage treatment for the crops.
As used herein, the term “agrochemical additives” may be understood to include a range of surfactants, dispersing agents, organic or inorganic pigments, solvents, de-solvents, defoamers, and emulsions, crystallization inhibitors, viscosity modifiers, suspending agents, dyes, antioxidants, foaming agents, light absorbers, mixing aids, neutralizers or pH adjusting substances and buffers, corrosion inhibitors, fragrances, wetting agents, absorption enhancers, micronutrients, plasticizers, lubricants, thickeners, anti-freezing agents, sterilization agents among others.

The herbicidal composition of the present invention may be formulated as capsule suspension (CS), dispersible concentrate (DC), dustable powder (DP), powder for dry seed treatment (DS), emulsifiable concentrate (EC), emulsifiable granule (EG), emulsion water in-oil (EO), emulsifiable powder (EP), emulsion for seed treatment (ES), emulsion oil-in-water (EW), flowable concentrate for seed treatment (FS), granules (GR), micro-emulsion (ME), oil-dispersion (OD), oil miscible flowable concentrate (OF), oil miscible liquid (OL), oil dispersible powder (OP), suspension concentrate (SC), suspension concentrate for direct application (SD), Suspo emulsion (SE), water soluble granule (SG), soluble concentrate (SL), spreading oil (SO), water soluble powder (SP), water soluble tablet (ST), ultra-low volume (ULV) suspension, tablet (TB), ultra-low volume (ULV) liquid, water dispersible granules (WG or WDG), wettable powder (WP), water dispersible powder for slurry seed treatment (WS), water dispersible tablet (WT), a mixed formulation of CS and SC (ZC), a mixed formulation of CS and SE (ZE), and a mixed formulation of CS and EW (ZW). Preferably, the composition of the present invention is formulated as Suspo emulsion (SE).

In an embodiment of the present invention provides a synergistic herbicidal composition suitable for preventing unwanted plants in crops like soybean, paddy rice and sugarcane.

One embodiment of the present invention provides a synergistic herbicidal composition comprising of a) sulfentrazone, b) pendimethalin, and c) oxyfluorfen with suitable agrochemical additives.

Another embodiment of the present invention provides a synergistic herbicidal composition comprising of:
a) sulfentrazone in a range from 5% (w/w) to 15% (w/w);
b) pendimethalin in a range from 20% (w/w) to 30% (w/w);
c) oxyfluorfen present in a range from 0.5% (w/w) to 5% (w/w), and
d) agrochemical additives.

Another embodiment of the present invention provides a Suspo emulsion (SE) composition comprising of:
a) sulfentrazone in a range from 5% (w/w) to 15% (w/w);
b) pendimethalin in a range from 20% (w/w) to 30% (w/w);
c) oxyfluorfen present in a range from 0.5% (w/w) to 5% (w/w), and
d) agrochemical additives.

According to the present invention, the suitable agrochemical additives are selected from a wetting agent, a dispersing agent, an anionic emulsifier, a non-ionic emulsifier, an antifreezing agent, a biocide, a defoamer, a rheology modifier, a solvent, and a filler.

According to the present invention, the wetting agent is selected from the group comprising of tristyrylphenol ethoxylate phosphate ester, polyoxyethylene polyoxypropylene condensate, polyoxyethylene alkyl ether, TERSEPERSE 2288, and cardphenol ethoxylate, present in a range from 1% to 5% (w/w).

According to the present invention, the dispersing agent is selected from the group comprising of anionic tristyrylphenol phosphate, tristyryl phenyl ether phosphate TEA salt, polymethyl methacrylate-polyethylene glycol graft copolymer, and ethoxylated alcohols (C12-16), present in a range from 1% to 5% (w/w).

According to the present invention, the anionic and non-ionic emulsifiers are selected from the group comprising of dodecylbenzene sulfonate, tristyrylphenol ethoxylate, IAL PA100, IAL PA200, alkoxylated alcohol and Ca-DDBS, castor oil ethylene oxide adduct, iso-C12 alkyl benzene sulfonate calcium salt, tristyrylphenol ethoxylate 16 mol EO (Emulsogen TS 160), n-C12 alkyl benzene sulfonate calcium salt, Castor oil based ethoxylate, 36 mol EO (EMULSOGEN EL 360), and combination thereof, present in a range from 1% to 10% (w/w).

According to the present invention, the antifreezing agent is propylene glycol, present in a range from 5% to 15% (w/w).

According to the present invention, the biocide is 1,2-benzisothiazalin-3-one, present in a range from 0.01% to 0.5% (w/w).

According to the present invention, the defoamer is Silicone antifoam emulsion, present in a range from 0.1% to 2% (w/w).

According to the present invention, the rheology modifier is xanthan gum, present in a range from 5% to 10% (w/w).

According to the present invention, the solvent is selected form C9-aromatic hydrocarbons (or) solvent naphtha, (petroleum), light aromatic, present in a range from 15% to 20% (w/w).

According to the present invention, the filler is water, present in Q.S.

In another embodiment of the present invention provides a process for the preparation of a Suspo emulsion (SE) composition comprising of sulfentrazone, pendimethalin and oxyfluorfen.

The composition of the present invention and method provided may be utilized to control weeds or battle undesired vegetation in crops or other settings, including but not limited to cereals, such as wheat, barley, rye, oats, corn/maize, rice, sorghum, triticale and related crops; fruit, such as pomes, stone fruit and soft fruit, for example apples, grapes, pears, plums, peaches, almonds, cherries, and berries, for example strawberries, raspberries and blackberries; leguminous plants, for examples beans, lentils, peas, soybeans, peanut; oil plants, for example rape, mustard, and sunflower; cucurbitaceae, for example marrows, cucumbers, melons; fiber plants, for example cotton, flax, hemp, jute; citrus fruit, for example oranges, lemons, grapefruit and mandarins; vegetable, for example spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, paparika; as well as ornamentals, such as flowers, shrubs, broad-leaved trees and evergreens, for example conifers, pastures, grasslands, rangelands, fallow and, turf, tree and vine orchards, and industrial vegetation management. Preferably, the undesirable vegetation includes species from the families of broadleaved and grass weeds, more preferably from the families of Aeschynomene, Ageratum, Amaranthus, Bidens, Brachiaria, Cenchrus, Cyperus, Digitaria, Echinochloa, Eclipta, Eleusine, Eragrostis Fimbristylis, Galinsoga, Ischaemum, Leptochloa, Monochoria, Panicum, Paspalum, Polygonum, Portulaca, Richardia, Sesbania, Setaria, Sida, Sorghum, most preferably Echinochloa, Leptochloa, Ischaemum, Monochoria, and Cyperus, or combinations thereof. It has been surprisingly found that the herbicidal composition of the present invention delays the appearance of the resistant strains of weeds and achieves effective and economical control of undesired weeds.
The composition achieves improved biological activity by enhancing overall control of weeds over a shorter period. Additional benefits of using the herbicidal composition of the present invention includes reduced risk of occupational hazard, lower cost of application, better cost: benefit ratio to the end user, reduced fuel, and labor cost, saving in applicator’s time and loss caused by mechanical damage to the crop and soil.

The present compositions can be applied to the undesirable vegetation and/or weeds or their locus using conventional ground or aerial dusters, sprayers, and granule applicators, by addition to irrigation or paddy water, and by other conventional means known to those skilled in the art.

The present invention is further illustrated by the following examples which are provided merely to be exemplary of the inventions and is not intended to limit the scope of the invention. Certain modifications and equivalents will be apparent to those skilled in the art and are intended to be included within the scope of the present invention.

Examples:

Example-1: The illustrative embodiments show the composition of sulfentrazone + pendimethalin + oxyfluorfen in Suspo emulsion (SE) form in different amount as follows:

Table-1: Sulfentrazone 9.29% + Pendimethalin 28.57% + Oxyfluorfen 1.57% SE
S. No Compositions Function Charge in (%)
1. Sulfentrazone Active ingredient 9.29
2. Pendimethalin Active ingredient 28.57
3. Oxyfluorfen Active ingredient 1.57
4. Tristyrylphenol ethoxylate phosphate ester Wetting agent 1.5
5. Anionic phosphate ester Dispersing agent 1.5
6. Dodecylbenzene sulfonate Anionic emulsifier 1.5
7. Tristyrylphenol ethoxylate Non-ionic emulsifier 1.5
8. Propylene glycol Antifreezing agent 12.0
9. 1,2-benzisothiazalin-3-one Biocide 0.10
10. Silicone antifoam emulsion Defoamer 0.50
11. Xanthan gum Rheology modifier 1.75
12. Solvent naphtha, (petroleum), light aromatic Solvent 20.0
13. Water Filler Q.S.

Process for manufacture of composition is as follows:
Step 1: Preparation of EW (A)
• An EW was prepared by incorporating Pendimethalin and Oxyfluorfen technical in suitable solvent C9 (Solvent naphtha, (petroleum), light aromatic) followed by addition of anionic (dodecylbenzene sulfonate) and non-anionic (tristyrylphenol ethoxylate) emulsifiers.
• Required quantity of antifreezing agent (propylene glycol) and filler (water) were added to the resultant mixture and kept under stirring.
Step 2: Preparation of Aqueous Slurry (B)
• Required quantity of dispersing agent (anionic phosphate ester) and wetting agents (tristyrylphenol ethoxylate phosphate ester) were added to antifreezing agent (propylene glycol) followed by addition of defoamer (Silicone antifoam emulsion) and biocide (1,2-benzisothiazalin-3-one).
• Required quantity of Sulfentrazone was added to the above and mixed under stirring.
• Post addition of water, stir the mixture for homogenization for about 1 hour (the mixture should be thoroughly homogenized).
Step 3:
• In this step, EW (A) portion was added to the Aqueous Slurry (B) and mixed under stirring.
Step 4: Wet Milling of Slurry
• Pass the wet slurry from Vessel No. 1 through Dyno-Mill at temperature less than 40 °C and collect material in Vessel No. 2 (Post-Mixer).
• Maintain continuous Stirring in both the vessels to avoid the sedimentation.
• Submit the sample to Quality Control Department to check the Particle Size distribution (PSD). The PSD of the material should be d90 < 5 µ. If the d90 is higher than > 5 µ then grind the mixture further till the PSD value complies the specification.
Step 5: Preparation of 2.0% Gel (Gel Suspension)
• Add 2.0 parts by weight of Xanthan gum (rheology modifier) in 4.0 parts by weight of Propylene glycol (antifreezing agent) then add this slurry into 94.0 parts by weight of distilled water and stir the mixture until it gets lumps free homogeneous mixture.
• Keep this gel as such for 4-5 hours to get a translucent homogeneous gel.
Step 6: Gelling of Wet Milled Slurry.
• Add the required quantity of Gel (prepared above) to the wet slurry in Vessel No. 2 and stir the mixture for ~2 h for homogenization.
• Submit the sample for total Quality Control for complete analysis.
Step 7: Pack the sample in HDPE container.

Table-2: Sulfentrazone 5.5% + Pendimethalin 25% + Oxyfluorfen 1.2% SE

S. No Compositions Function Charge in (%)
1. Sulfentrazone Active ingredient 5.50
2. Pendimethalin Active ingredient 25.0
3. Oxyfluorfen Active ingredient 1.2
4. Polyoxyethylene polyoxypropylene condensate Wetting agent 2.5
5. Tristyryl phenyl ether phosphate TEA salt Dispersing agent 2.5
6. IAL PA100 Anionic emulsifier 5.0
7. IAL PA200 Non-ionic emulsifier 5.0
8. Propylene glycol Antifreezing agent 10.0
9. 1,2-benzisothiazalin-3-one Biocide 0.02
10. Silicone antifoam emulsion Defoamer 0.10
11. Xanthan gum Rheology modifier 5.0
12. Solvent naphtha, (petroleum), light aromatic Solvent 20.0
13. Water Filler Q.S.

The process for manufacture of composition is similar to the procedure as described in Table-1.

Table-3: Sulfentrazone 10.0% + Pendimethalin 22.5% + Oxyfluorfen 2.50% SE

S. No Compositions Function Charge in (%)
1. Sulfentrazone Active ingredient 10.0
2. Pendimethalin Active ingredient 22.50
3. Oxyfluorfen Active ingredient 2.50
4. Nonionic proprietary surfactant blend Wetting agent 5.0
5. Acrylic copolymer solution Dispersing agent 5.0
6. Alkoxylated alcohol and Ca-DDBS Anionic emulsifier 2.5
7. Castor oil ethylene oxide adduct Non-ionic emulsifier 2.5
8. Propylene glycol Antifreezing agent 12.0
9. 1,2-benzisothiazalin-3-one Biocide 0.20
10. Silicone antifoam emulsion Defoamer 1.0
11. Xanthan gum Rheology modifier 5.0
12. Solvent naphtha, (petroleum), light aromatic Solvent 15.0
13. Water Filler Q.S.

The process for manufacture of composition is similar to the procedure as described in Table-1.

Table-4: Sulfentrazone 12.0% + Pendimethalin 25.0% + Oxyfluorfen 3.80% SE

S. No Compositions Function Charge in (%)
1. Sulfentrazone Active ingredient 12.0
2. Pendimethalin Active ingredient 25.0
3. Oxyfluorfen Active ingredient 3.80
4. TERSEPERSE 2288 Wetting agent 5.0
5. Ethoxylated alcohols (C12-16) Dispersing agent 5.0
6. Iso-C12 alkyl benzene sulfonate calcium salt Anionic emulsifier 2.5
7. Tristyrylphenol ethoxylate Non-ionic emulsifier 2.5
8. Propylene glycol Antifreezing agent 10.0
9. 1,2-benzisothiazalin-3-one Biocide 0.5
10. Silicone antifoam emulsion Defoamer 0.5
11. Xanthan gum Rheology modifier 5.0
12. Solvent naphtha, (petroleum), light aromatic Solvent 15.0
13. Water Filler Q.S.

The process for manufacture of composition is similar to the procedure as described in Table-1.

Table-5: Sulfentrazone 11% + Pendimethalin 29.5% + Oxyfluorfen 0.8% SE

S. No Compositions Function Charge in (%)
1. Sulfentrazone Active ingredient 11.0
2. Pendimethalin Active ingredient 29.5
3. Oxyfluorfen Active ingredient 0.80
4. Cardphenol Ethoxylate Wetting agent 2.5
5. n-C12 alkyl benzene sulfonate calcium salt Anionic emulsifier 2.5
6. Castor oil based ethoxylate, 36 mol EO Non-ionic emulsifier 5.0
7. Propylene glycol Antifreezing agent 15.0
8. 1,2-benzisothiazalin-3-one Biocide 0.01
9. Silicone antifoam emulsion Defoamer 0.1
10. Xanthan Rheology modifier 10.0
11. Solvent naphtha, (petroleum), light aromatic Solvent 20.0
12. Water Filler Q.S.

The process for manufacture of composition is similar to the procedure as described in Table-1.

Example 2: Efficacy study of Sulfentrazone 9.29% + Pendimethalin 28.57% + Oxyfluorfen 1.57% in Suspo emulsion (SE) form:

SYNERGY STUDIES:

Soybean is an important rainy season crop of India. In India, it is grown on an area of 108.83 lakh ha with an annual production of 104.36 lakh million tons. Successful weed control is the most important factor for fruitful soybean production because losses due to weeds have been one of the major limiting factors in soybean production. Weeds compete with crops for light moisture and nutrients. Being a rainy season crop soybean faces severe weed competition during crop growth, resulting in a loss of about 40-60% of the potential yield. Traditionally, weed control in India has been largely dependent on manual weeding. However, increased labour scarcity and costs are encouraging farmers to adopt herbicides.

The field studies were conducted to compare the weed controlling activity of the combination of Sulfentrazone, Oxyfluorfen & Pendimethalin. The active ingredient Sulfentrazone & Oxyfluorfen in the combination, belongs to chemical family “N-phenyl phthalimides & Diphenyl ethers” respectively, with mode of action Protoporphyrinogen oxidase (PPO) and Pendimethalin herbicide belongs to chemical class “Dinitroaniline” with microtubule Assembly inhibitor mode of action. Combination has the potential of controlling the cross-spectrum weeds (broad leaf weeds & grassy weeds) in soybean at the pre-emergence (0-3 DAS) application timing. Both the molecules are safe to soybean when applied at their recommended dose rate in pre-emergence (0-3 DAS) application timing.

The weed control activity of the individual herbicides of the invention and their combinations were evaluated on weeds such as Acalypha indica, Commelina benghalensis, Commelina communis, Digera arvensis, Echinochloa colona and Ischaemum rugosum. Trials were conducted with randomized block design with net plot size of 5m x 6 m. Each trial was replicated four times and conducted under GEP guidelines. Spraying was done with manual operated backpack knapsack sprayer with 300 L of water spray volume per hectare at pre-emergence (0-3 DAS) application timing. Such field trials were carried out at various locations to generate independent data, the locations were chosen randomly across India.

Visual observations were recorded on percent weed control for individual weeds on whole plot basis at 30 days after application. These observations are to be taken from the entire plot.

Appropriate analysis of plant response to herbicide combination is critical in determining the type of activity observed. The most widely used model is the one Gowing* derived and Colby** modified. Gowing described a mathematical formula for calculating the predicting response values for pesticide mixtures. He suggested the two formulae’s for determining the synergy between two-way and three-way combinations, *(Jerry Flint et al, 1988) ***

Three-way combination:
(AB + AC + BC) ABC
Expected (E) = A + B + C - +
100 10000
Where,
A = observed efficacy of active ingredient A at the same concentration as used in the mixture.
B = observed efficacy of active ingredient B at the same concentration as used in the mixture.
C = observed efficacy of active ingredient C at the same concentration as used in the mixture.

Two-way combination:

If A1 = the percent inhibition of growth by herbicide A at given rate
B1 = the percent inhibition of growth by herbicide B at given rate then,
B1 (100 – A1)
E = A1 +
100
Where,
A = observed efficacy of active ingredient A at the same concentration as used in the mixture.
B = observed efficacy of active ingredient B at the same concentration as used in the mixture.
C = observed efficacy of active ingredient C at the same concentration as used in the mixture.

When the percentage of pesticidal control observed for the combination is greater than the expected percentage, there is a synergistic effect. (Ratio of O/E > 1, means synergism observed.)

Reference:
*Gowing, D. P. 1960. Comments on tests of herbicide mixtures. Weeds 8:379–391.
**Colby, S. R. 1967. Calculating synergistic and antagonistic responses of herbicide combinations. Weeds 15:20–22
*** Jerry Flint et al, 1988. Analyzing Herbicide Interactions: A Statistical Treatment of Colby's Method. Weed Technology 2: 304-309

The herbicide combinations, application rates, plant species tested, and results are given in the following tables:

Table 6: Demonstrates synergy on weeds using the combination of Sulfentrazone, Pendimethalin and Oxyfluorfen. The field trials were carried out in India at various locations. The percentage efficacy was calculated after 30 days of application. The target weeds were Commelina benghalensis and Commelina communis and the results are recorded in the below table.

Active Dose (GAH) % Weed Control of Commelina benghalensis % Weed Control of Commelina communis
Expected Observed Expected Observed
Sulfentrazone 39.6% SC 300 75 70
Pendimethalin 30% EC 928 10 10
Oxyfluorfen 23.5% EC 51 55 50
Sulfentrazone 39.6% SC + Pendimethalin 30% EC 300 + 928 77.5 77.5 73 72
Ratio of O/E 1.00 0.98
Pendimethalin 30% EC + Oxyfluorfen 23.5% EC 928 + 51 59.5 55 55 55
Ratio of O/E 0.92 1.00
Sulfentrazone 39.6% SC + Oxyfluorfen 23.5% EC 300 + 51 88.75 85 85 82
Ratio of O/E 0.95 0.96
Sulfentrazone 9.29% + Pendimethalin 28.57% + Oxyfluorfen 1.57% SE 300 + 928 + 51 87.85 95 86.5 94
Ratio of O/E 1.01 1.05
SC – Suspension concentrate; EC – Emulsion concentrate; SE – Suspo emulsion; and DAA - Days after application.

The results in table 6 clearly demonstrate synergy between Sulfentrazone, Pendimethalin and Oxyfluorfen against weeds like Commelina benghalensis and Commelina communis. The higher ratio of the observed and the expected efficacy clearly demonstrates the synergistic effect of the combination.

Table 7: Demonstrates synergy on weeds using the combination of Sulfentrazone, Pendimethalin and Oxyfluorfen. The field trials were carried out in India at various locations. The percentage efficacy was calculated after 30 days of application. The target weeds were Echinochloa colonum and Ischaemum rugosum and the results are recorded in the below table.

Active Dose (GAH) % Weed Control of Echinochloa colonum % Weed Control of Ischaemum rugosum
Expected Observed Expected Observed
Sulfentrazone 39.6% SC 300 10 0
Pendimethalin 30% EC 928 98 90
Oxyfluorfen 23.5% EC 51 40 25
Sulfentrazone 39.6% SC + Pendimethalin 30% EC 300 + 928 98.2 98 90 90
Ratio of O/E 0.98 1.00
Pendimethalin 30% EC + Oxyfluorfen 23.5% EC 928 + 51 98.8 98 92.5 90
Ratio of O/E 0.99 0.97
Sulfentrazone 39.6% SC + Oxyfluorfen 23.5% EC 300 + 51 46 45 25 20
Ratio of O/E 0.97 0.80
Sulfentrazone 9.29% + Pendimethalin 28.57% + Oxyfluorfen 1.57% SE 300 + 928 + 51 98.92 100 92.5 98
Ratio of O/E 1.01 1.05
SC – Suspension concentrate; EC – Emulsion concentrate; SE – Suspo emulsion; and DAA - Days after application.

The results in table 7 clearly demonstrate efficacy of Sulfentrazone, Pendimethalin and Oxyfluorfen against weeds like Echinochloa colonum and Ischaemum rugosum. The higher ratio of the observed and the expected efficacy clearly demonstrates the synergistic effect of the combination.

Table 8: Demonstrates synergy on weeds using the combination of Sulfentrazone, Oxyflurofen & Pendimethalin. The field trials were carried out in India at various locations. The percentage efficacy was calculated after 30 days of application. The target weeds were Dinebra retroflexa and Brachiaria erusiformis and the results are recorded in the below table.

Active Dose (GAH) % Weed Control of Dinebra retroflexa % Weed Control of Brachiaria erusiformis
Expected Observed Expected Observed
Sulfentrazone 39.6% SC 300 15 0
Pendimethalin 30% EC 928 80 85
Oxyfluorfen 23.5% EC 51 35 25
Sulfentrazone 39.6% SC + Pendimethalin 30% EC 300 + 928 83 80 85 85
Ratio of O/E 0.96 1.00
Pendimethalin 30% EC + Oxyfluorfen 23.5% EC 928 + 51 87 85 88.75 85
Ratio of O/E 0.97 0.95
Sulfentrazone 39.6% SC + Oxyfluorfen 23.5% EC 300 + 51 44.75 40 25 20
Ratio of O/E 0.89 0.80
Sulfentrazone 9.29% + Pendimethalin 28.57% + Oxyfluorfen 1.57% SE 300 + 928 + 51 88.95 95 88.75 95
Ratio of O/E 1.06 1.07
SC – Suspension concentrate; EC – Emulsion concentrate; SE – Suspo emulsion; and DAA - Days after application.

The results in table 8 clearly demonstrate efficacy of Sulfentrazone, Pendimethalin and Oxyfluorfen against weeds like Dinebra retroflexa and Brachiaria erusiformis. The higher ratio of the observed and the expected efficacy clearly demonstrates the synergistic effect of the combination.

Table 9: Demonstrates synergy on weeds using the combination of Sulfentrazone, Pendimethalin and Oxyfluorfen. The field trials were carried out in India at various locations. The percentage efficacy was calculated after 30 days of application. The target weeds were Acalypha indica and Digera arvensis and the results are recorded in the below table.

Active Dose (GAH) % Weed Control of Acalypha indica % Weed Control of Digera arvensis
Expected Observed Expected Observed
Sulfentrazone 39.6% SC 300 90 90
Pendimethalin 30% EC 928 0 20
Oxyfluorfen 23.5% EC 51 58 65
Sulfentrazone 39.6% SC + Pendimethalin 30% EC 300 + 928 90 90 92 92
Ratio of O/E 1.00 1.00
Pendimethalin 30% EC + Oxyfluorfen 23.5% EC 928 + 51 58 55 72 70
Ratio of O/E 0.94 0.97
Sulfentrazone 39.6% SC + Oxyfluorfen 23.5% EC 300 + 51 95.8 94 96.5 95
Ratio of O/E 0.98 0.98
Sulfentrazone 9.29% + Pendimethalin 28.57% + Oxyfluorfen 1.57% SE 300 + 928 + 51 95.8 98 97.2 100
Ratio of O/E 1.02 1.02
SC – Suspension concentrate; EC – Emulsion concentrate; SE – Suspo emulsion; and DAA - Days after application.

The results in table 9 clearly demonstrate efficacy of Sulfentrazone, Pendimethalin and Oxyfluorfen against weeds like Acalypha indica and Digera arvensis. The higher ratio of the observed and the expected efficacy clearly demonstrates the synergistic effect of the combination.

WE CLAIM:

1. A synergistic Suspo emulsion (SE) herbicidal composition for preventing unwanted plants in crops comprising of (a) sulfentrazone, (b) pendimethalin, and (c) oxyfluorfen.
2. The composition as claimed in claim 1, wherein the crops are soybean, paddy rice and sugarcane.
3. The composition as claimed in claim 1, wherein the composition comprising of:
a) sulfentrazone in a range from 5% (w/w) to 15% (w/w);
b) pendimethalin in a range from 20% (w/w) to 30% (w/w);
c) oxyfluorfen present in a range from 0.5% (w/w) to 5% (w/w), and
d) agrochemical additives.
4. The composition as claimed in claim 3, wherein the agrochemical additives are selected from a wetting agent, a dispersing agent, an anionic emulsifier, a non-ionic emulsifier, an antifreezing agent, a biocide, a defoamer, a rheology modifier, a solvent, and a filler.
5. The composition as claimed in claim 3, wherein the wetting agent is selected from tristyrylphenol ethoxylate phosphate ester, Polyoxyethylene polyoxypropylene condensate, polyoxyethylene alkyl ether, TERSEPERSE 2288, and Cardphenol ethoxylate, present in a range from 1% to 5% (w/w).
6. The composition as claimed in claim 3, wherein the dispersing agent is selected from anionic tristyrylphenol phosphate, tristyryl phenyl ether phosphate TEA salt, polymethyl methacrylate-polyethylene glycol graft copolymer, and ethoxylated alcohols (C12-16), present in a range from 1% to 5% (w/w).
7. The composition as claimed in claim 3, wherein the anionic and non-ionic emulsifiers are selected from the group comprising of dodecylbenzene sulfonate, tristyrylphenol ethoxylate, IAL PA100, IAL PA200, alkoxylated alcohol and Ca-DDBS, Castor oil ethylene oxide adduct, iso-C12 alkyl benzene sulfonate calcium salt, tristyrylphenol ethoxylate 16 mol EO, n-C12 alkyl benzene sulfonate calcium salt, castor oil based ethoxylate, 36 mol EO, and combination thereof, present in a range from 1% to 10% (w/w).
8. The composition as claimed in claim 3, wherein the defoamer is silicone antifoam emulsion, present in a range from 0.1% to 2% (w/w), the antifreezing agent is propylene glycol, present in a range from 5% to 15% (w/w), and biocide is 1,2-benzisothiazalin-3-one, present in a range from 0.01% to 0.5% (w/w).
9. The composition as claimed in claim 3, wherein the rheology modifier is xanthan gum, present in a range from 5% to 10% (w/w).
10. The composition as claimed in claim 3, wherein the solvent is solvent naphtha, (petroleum), light aromatic, present in a range from 15% to 20% (w/w), and the filler is water, present in Q.S.

Dated this Twenty-Eight (28th) day of November 2023

Sahadev Katam,
General Manager, Legal-IPR,
Coromandel International Limited,
Registered Indian Patent Agent No. IN/PA/5560

ABSTRACT

SUSPO EMULSION COMPOSITION OF SULFENTRAZONE, PENDIMETHALIN AND OXYFLUORFEN

The present invention relates to a kind of synergistic herbicide composition that contains herbicidal active compounds, and it is suitable for preventing unwanted plants in the crops like soybean, paddy rice and sugarcane.
, Claims:WE CLAIM:

1. A synergistic Suspo emulsion (SE) herbicidal composition for preventing unwanted plants in crops comprising of (a) sulfentrazone, (b) pendimethalin, and (c) oxyfluorfen.
2. The composition as claimed in claim 1, wherein the crops are soybean, paddy rice and sugarcane.
3. The composition as claimed in claim 1, wherein the composition comprising of:
a) sulfentrazone in a range from 5% (w/w) to 15% (w/w);
b) pendimethalin in a range from 20% (w/w) to 30% (w/w);
c) oxyfluorfen present in a range from 0.5% (w/w) to 5% (w/w), and
d) agrochemical additives.
4. The composition as claimed in claim 3, wherein the agrochemical additives are selected from a wetting agent, a dispersing agent, an anionic emulsifier, a non-ionic emulsifier, an antifreezing agent, a biocide, a defoamer, a rheology modifier, a solvent, and a filler.
5. The composition as claimed in claim 3, wherein the wetting agent is selected from tristyrylphenol ethoxylate phosphate ester, Polyoxyethylene polyoxypropylene condensate, polyoxyethylene alkyl ether, TERSEPERSE 2288, and Cardphenol ethoxylate, present in a range from 1% to 5% (w/w).
6. The composition as claimed in claim 3, wherein the dispersing agent is selected from anionic tristyrylphenol phosphate, tristyryl phenyl ether phosphate TEA salt, polymethyl methacrylate-polyethylene glycol graft copolymer, and ethoxylated alcohols (C12-16), present in a range from 1% to 5% (w/w).
7. The composition as claimed in claim 3, wherein the anionic and non-ionic emulsifiers are selected from the group comprising of dodecylbenzene sulfonate, tristyrylphenol ethoxylate, IAL PA100, IAL PA200, alkoxylated alcohol and Ca-DDBS, Castor oil ethylene oxide adduct, iso-C12 alkyl benzene sulfonate calcium salt, tristyrylphenol ethoxylate 16 mol EO, n-C12 alkyl benzene sulfonate calcium salt, castor oil based ethoxylate, 36 mol EO, and combination thereof, present in a range from 1% to 10% (w/w).
8. The composition as claimed in claim 3, wherein the defoamer is silicone antifoam emulsion, present in a range from 0.1% to 2% (w/w), the antifreezing agent is propylene glycol, present in a range from 5% to 15% (w/w), and biocide is 1,2-benzisothiazalin-3-one, present in a range from 0.01% to 0.5% (w/w).
9. The composition as claimed in claim 3, wherein the rheology modifier is xanthan gum, present in a range from 5% to 10% (w/w).
10. The composition as claimed in claim 3, wherein the solvent is solvent naphtha, (petroleum), light aromatic, present in a range from 15% to 20% (w/w), and the filler is water, present in Q.S.
Dated this Twenty-Eight (28th) day of November 2023

Sahadev Katam,
General Manager, Legal-IPR,
Coromandel International Limited,
Registered Indian Patent Agent No. IN/PA/5560