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Synergistic Phenylphthalimide And Dinitroaniline Combinations, Formulations, Process For Preparing And Use Thereof

Abstract: ABSTRACT SYNERGISTIC PHENYLPHTHALIMIDE and DINITROANILINE COMBINATIONs, FORMULATIONs, PROCESS FOR PREPARING AND USE THEREOF The present invention relates to synergistic composition comprising combination of a phenylphthalimide herbicide and dinitroaniline herbicide. The present invention also relates to synergistic comprising combination of a phenylphthalimide herbicide, dinitroaniline herbicide and other agrochemical auxiliaries. The present invention specifically relates to emulsifiable concentrate (EC) composition comprising combination of Flumioxazin and Pendimethalin. The present invention also relates to a process for the preparation of emulsifiable concentrate composition comprising combination of Flumioxazin and Pendimethalin, wherein the composition is prepared by simple blending and homogenization process.

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Patent Information

Application #
Filing Date
26 August 2020
Publication Number
09/2022
Publication Type
INA
Invention Field
CHEMICAL
Status
Email
patfiling@ipropat.com
Parent Application

Applicants

COROMANDEL INTERNATIONAL LIMITED
Coromandel House, Sardar Patel Road, Secunderabad, Telangana, India 500003

Inventors

1. Kiran PAWAR
Coromandel House, Sardar Patel Road, Secunderabad, Telangana, India 500003
2. Balaram BHAVANI
Coromandel House, Sardar Patel Road, Secunderabad, Telangana, India 500003
3. Rajan Kumar TRIVEDI
Coromandel House, Sardar Patel Road, Secunderabad, Telangana, India 500003
4. Rajul EDOLIYA
Coromandel House, Sardar Patel Road, Secunderabad, Telangana, India 500003
5. Aminul ISLAM
Coromandel House, Sardar Patel Road, Secunderabad, Telangana, India 500003

Specification

DESC:FORM 2

THE PATENTS ACT, 1970
(SECTION 39 OF 1970)
&
The Patents Rules, 2003

COMPLETE SPECIFICATION
(Section 10 and Rule 13)

SYNERGISTIC PHENYLPHTHALIMIDE and DINITROANILINE COMBINATIONs, FORMULATIONs, PROCESS FOR PREPARING AND USE THEREOF

We, COROMANDEL INTERNATIONAL LIMITED,
an Indian company incorporated under Companies Act of 1956, having its principal place of business 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 synergistic composition comprising combination of a phenylphthalimide herbicide and dinitroaniline herbicide.

The present invention also relates to synergistic comprising combination of a phenylphthalimide herbicide, dinitroaniline herbicide and other agrochemical auxiliaries.

The present invention specifically relates to emulsifiable concentrate (EC) composition comprising combination of Flumioxazin and Pendimethalin.

The present invention specifically relates to emulsifiable concentrate composition comprising combination of Flumioxazin and Pendimethalin at a weight in the ratio of 1 : 15 to 15 : 1 of first active ingredient to the second active ingredient, more preferably in the ratio of 1 : 10 to 10 : 1.

The present invention also relates to a process for the preparation of emulsifiable concentrate composition comprising combination of Flumioxazin and Pendimethalin, wherein the composition is prepared by simple blending and homogenization process.

BACKGROUND OF THE INVENTION
Flumioxazin is a member of diphenyl ether group of herbicides, which inhibits protoporphyrinogen oxidase (PPO). Flumioxazin is a light-dependent peroxidizing herbicide (LDPH), which acts by blocking heme and chlorophyll biosynthesis resulting in an endogenous accumulation of phototoxic porphyrins. This class of herbicides are known to have a phototoxic mode of action in plants and possibly in fish. The formulated product contains 51% flumioxazin in a water soluble granule. The product is applied as a foliar spray at a maximum application rate of three ounces per acre per year, or 0.0956 lb. active ingredient/acre/year. The product is labeled for control of susceptible weeds in peanuts and soybeans, and can also be used as part of an early preplant burn down program in cotton, field corn, rice, sorghum, sunflowers, and wheat.

Flumioxazin is chemically known as N-(7-fluoro-3,4-dihydro-3-oxo-4-prop-2-ynyl-2H-1,4-benzoxazin-6-yl)cyclohex-1-ene-1,2-dicarboximide and has the following structure:

Pendimethalin is an herbicide of the dinitroaniline class used in premergence and postemergence applications to control annual grasses and certain broadleaf weeds. It inhibits cell division and cell elongation. Pendimethalin is listed in the K1-group according to the Herbicide Resistance Action Committee (HRAC) classification and is approved in Europe, North America, South America, Africa, Asia and Oceania for different crops including cereals (wheat, barley, rye, triticale), corn, soybeans, rice, potato, legumes, fruits, vegetables, nuts as well as lawns and ornamental plants.

Pendimethalin protects crops like wheat, corn, soybeans potatoes, cabbage, peas, carrots and asparagus. It is used to control annual grasses and certain broad leaf weeds which interfere with growth, development, yield and quality of agricultural and horticultural crops by competing on nutrients, water and light. Pendimethalin acts both pre-emergence, that is before weed seedlings have emerged, and early post-emergence. Pendimethalin inhibits root and shoot growth. It controls the weed population and prevents weeds from emerging, particularly during the crucial development phase of the crop. Its primary mode of action is to prevent plant cell division and elongation in susceptible species. In the HRAC classification of herbicides according their mode of action, pendimethalin is listed in group K1.

Pendimethalin is chemically, 3,4-dimethyl-2,6-dinitro-N-pentan-3-yl-aniline and has the following structure:

US 3,920,742 A claims compositions of Pendimethalin and its analogs.

US 4,640,707 A claims Flumioxazin and its compositions.

Though, conventionally each of these active ingredients are used individually, combination product is not approved which has applications compared to the mono product. Hence, there is increased interest in the use of active ingredients in combination to give synergistic results.

Therefore, formulations of active substances in combinations should generally have good chemical and physical stability, good application properties, user friendliness, having good biological activity and enhanced efficacy combined with high selectivity. Proper formulation and efficient delivery systems of combinations fungicides are the key elements in the performance of different products.

Accordingly, there is a need in the art to provide herbicidal synergistic compositions which are environmentally safer and stable herbicidal compositions having two active ingredients with different physical and chemical properties, which are environmentally safe, easy and effective combination formulation of two active with enhanced efficacy and stable product during storage.

It was surprisingly and unexpectedly found by the present inventors that a selective combination composition of two active ingredients comprising Flumioxazin and Pendimethalin, and other agrochemical auxiliaries, possesses enhanced efficacy, improved penetration and long duration control of phytopathogens as compared to its other traditional formulations with long storage stability across a wide temperature range and having no adverse impact on photosynthetic activity in plant and seed quality.

OBJECTIVE OF INVENTION
The main objective of the present invention is to provide synergistic composition comprising combination of a phenylphthalimide herbicide and dinitroaniline herbicide.

Another objective of the present invention is to provide synergistic comprising combination of a phenylphthalimide herbicide, dinitroaniline herbicide and agrochemical auxiliaries.

Another objective of the present invention is to provide emulsifiable concentrate composition comprising combination of Flumioxazin and Pendimethalin.

Another objective of the present invention is to provide emulsifiable concentrate composition comprising combination of Flumioxazin and Pendimethalin and other agrochemical auxiliaries.

Another objective of the present invention is to provide emulsifiable concentrate composition comprising combination Flumioxazin and Pendimethalin at a weight in the ratio of 1 : 15 to 15 : 1 of first active ingredient to the second active ingredient, more preferably in the ratio of 1 : 10 to 10 : 1.

Another objective of the present invention is to provide a process for the preparation of emulsifiable concentrate composition comprising combination of Flumioxazin and Pendimethalin wherein the product is prepared by simple blending and homogenization process.

SUMMARY OF INVENTION
Accordingly, the present invention provides a synergistic composition comprising combination of phenylphthalimide herbicide and dinitroaniline herbicide.

In one embodiment, the present invention provides a synergistic composition comprising:
a) phenylphthalimide herbicide,
b) dinitroaniline herbicide, and
c) agrochemical auxiliaries.

In another embodiment, the present invention provides a synergistic composition comprising combination of phenylphthalimide herbicide, dinitroaniline herbicide and an agrochemical auxiliary, wherein said phenylphthalimide herbicide is Flumioxazin and dinitroaniline herbicide is Pendimethalin.

In another embodiment, the present invention provides a synergistic composition comprising combination of phenylphthalimide herbicide, dinitroaniline herbicide and agrochemical auxiliaries, wherein said composition is emulsifiable concentrate.

In one embodiment, the present invention provides a synergistic herbicidal emulsifiable concentrate composition comprising:
a) phenylphthalimide,
b) dinitroaniline, and
c) agrochemical auxiliaries.

In another embodiment, the present invention provides an emulsifiable concentrate composition comprising combination of Flumioxazin and Pendimethalin.

In another embodiment, the present invention provides an emulsifiable concentrate composition comprising combination of Flumioxazin and Pendimethalin at a weight in the ratio of 1 : 15 to 15 : 1 of first active ingredient to the second active ingredient, more preferably in the ratio of 1 : 10 to 10 : 1.

In another embodiment, the present invention provides an emulsifiable concentrate composition comprising:
a) Flumioxazin,
b) Pendimethalin, and
c) agrochemical auxiliaries.

In another embodiment, the present invention provides an emulsifiable concentrate composition comprising:
a) Flumioxazin,
b) Pendimethalin,
c) emulsifiers, and
d) solvents.

In another embodiment, the present invention provides an emulsifiable concentrate composition comprising:
a) 1% to 15% (w/w) of Flumioxazin,
b) 1% to 15% (w/w) of Pendimethalin,
c) 1% to 30% (w/w) of emulsifier, and
d) 1% to 80% (w/w) of solvent.

In another embodiment, the present invention provides an emulsifiable concentrate composition comprising:
a) 1% to 15% (w/w) of Flumioxazin,
b) 1% to 15% (w/w) of Pendimethalin,
c) 1% to 20% (w/w) of linear dodecylbenzene sulphonate, calcium salt in 2-ethylexanol solution,
d) 1% to 10% (w/w) of polyalkoxylated butyl ether,
e) 1% to 30% (w/w) of 1-methylpyrrolidin-2-one,
f) 1% to 20% (w/w) of cyclohexanone, and
g) 1% to 30% (w/w) of solvent naphtha (Petroleum).

In another embodiment, the present invention provides a process for the preparation of composition comprising the steps of:
a) weighing all the active ingredients and agrochemical auxiliaries,
b) mixing all the ingredients under stirring, and
c) homogenizing the obtained material, filtering and packing.

In another embodiment, the present invention provides a process for the preparation of emulsifiable concentrate composition comprising the steps of:
a) weighing and mixing Pendimethalin, Flumioxazin, linear dodecylbenzene sulphonate, calcium salt in 2-ethylexanol solution, polyalkoxylated butyl ether, of 1-methylpyrrolidin-2-one, cyclohexanone and solvent naphtha under stirring and
b) homogenizing the obtained material, filtering and packing.

DETAILED 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.

The present invention provides synergistic composition comprising combination of 1 : 15 to 15 : 1 of first active ingredient to the second active ingredient, more preferably in the ratio of 1 : 10 to 10 : 1. However, variables of the ratios of each of the active ingredients can be used and the selection of the particular amount is dependent upon many factors including, for example, type of formulations, the crop, disease sought to be controlled and environmental conditions. The selection of the proper quantity of active agent to be applied, however, is within the expertise of one skilled in the art.

The composition of the present invention could be applied to plants, seeds, fruits, soil as preventive and curative state.

ECs are versatile formulations that can be applied with many types of sprayers. EC compositionenable spontaneous emulsification upon dilution and are easy to handle and measure. Very little agitation is required to mix them with water, and will not separate; Little visible residue on the plant; do not wear sprayer parts or plug screens or nozzles; Seldom leaves visible residue

The emulsifier used in the composition allows the active ingredient in the solvent to mix with water, these form an emulsion. The emulsifying surfactant system enabling the EC to form an oil-in-water emulsion when the formulation is added to water is typically a mixture of two or more surfactants, at least one of which is a nonionic surfactant and optionally at least one of which is an anionic surfactant.

The surfactants customarily employed in formulation technology, which are described, inter alia, in “Mc Cutcheon's Detergents and Emulsifiers Annual” MC Publishing Corp., Ridgewood N.J., 1981, Stache, H., “Tensid-Taschenbuch”, Carl Hanser Verlag, Munich Nienna, 1981 and M. and J. Ash, “Encyclopedia of Surfactants”, Vol I-III, Chemical Publishing Co., New York, 1980-81, are also suitable for preparation of the herbicidal compositions according to the invention.

Anionic surfactants suitable for use in the invention may be any known in the art. The anionic surfactants may be polyarylphenol polyalkoxyether sulfates and/or phosphates; C8-18 alcohol polyalkoxyether phosphates, carboxylates, and/or citrates; alkyl benzenesulfonic acids; C8-20 alkyl carboxylates including fatty acids; C8-20 alcohol sulfates; C8-20 alcohol phosphate mono- and diesters; C8-20 alcohol and (C8-20alkyl)phenol polyoxyethylene ether carboxylates, sulfates and sulfonates; C8-20 alcohol and (C8-20 alkyl)phenol polyoxyethylene phosphate mono- and diesters; C8-20 alkylbenzene sulfonates (Geronol FF4 and Geronol FF6 etc), naphthalene sulfonates and formaldehyde condensates thereof; lignosulfonates; C8-20 alkyl sulfosuccinates and sulfosuccinamates; C8-20 acyl glutamates, sarcosinates, isethionates and taurates; water-soluble soaps and mixtures thereof.

Exemplary polyarylphenol polyalkoxyether sulfates and phosphates include polyarylphenol polyethoxyether sulfates and phosphates, polyarylphenol polypropoxyether sulfates and phosphates, polyarylphenol poly(ethoxy/propoxy)ether sulfates and phosphates, and salts thereof. The term “aryl” includes, for example, phenyl, tolyl, naphthyl, tetrahydronaphthyl, indanyl, indenyl, styryl, pyridyl, quinolinyl, and mixtures thereof. Exemplary polyarylphenol polyethoxyether sulfates and phosphates include distyrylphenol polyethoxyether sulfates and phosphates, and tristyrylphenol polyethoxyether sulfates and phosphates. The polyarylphenol polyalkoxether sulfates and phosphates may have a degree of alkoxylation (e.g., ethoxylation) of between about 1 and about 50, preferably between about 2 and about 40, more preferably between about 5 and about 30. Commercially available polyarylphenol polyalkoxyether sulfates and phosphates include, for example, SOPROPHOR® 4 D 384 (tristyrylphenol (EO)16 sulfate ammonium salt), SOPROPHOR® 3 D 33 (tristyrylphenol (EO)16 phosphate free acid), SOPROPHOR® FLK (tristyrylphenol (EO)16 phosphate potassium salt) and SOPROPHOR® RAM/384 (tristyrylphenol polyethoxylated ether sulfate neutralized with polyethoxylated oleylamine). In other embodiments, the polyarylphenol polyalkoxyether sulfates and phosphates may be mono-arylphenol polyalkoxyether sulfates and phosphates, such as styrylphenol polyethoxyether sulfates and phosphates.

Exemplary C8-18 alcohol polyethoxyether phosphates, carboxylates and citrates include STEPFAC® 8180 (tridecylalcohol (EO)3 phosphate), STEPFAC® 8181 (tridecylalcohol (EO)6 phosphate), STEPFAC® 8182 (tridecylalcohol (EO)12 phosphate), EMCOL® CN-6 (tridecylalcohol (EO)6 carboxylate). The C8-18 alcohol polyethoxyether phosphates, carboxylates and citrates may have a degree of ethoxylation of between about 1 and about 25, preferably between about 1 and about 20.

Exemplary alkylbenzene sulfonic acids and salts thereof include dodecylbenzene sulfonic acid, and metal (for example sodium or calcium, Atlox™ 4838B, Rhodacal 60/BER), ammonia or amine salts of the alkylbenzene sulfonic acids, including dodecylbenzene sulfonic acid. Amine neutralized versions include primary amines, diamines, triamines and alkanol amines.

Additional preferred anionic surfactants include (C8-12 alkyl)phenol polyoxyethylene ether sulfates, and (C8-12 alkyl)phenol polyoxyethylene phosphate mono- and diesters, accompanied in each case by monovalent counterions. In one embodiment the monovalent counterion for a (C8-12 alklyl)phenol polyoxyethylene ether sulfate or a (C8-12 alkyl)phenol polyoxyethylene phosphate is a protonated polyoxyethylene C12-20 alkylamine surfactant. More specifically, polyoxyethylene tallowamine salt of a nonylphenol polyoxyethylene ether sulfate, nonylphenol polyoxyethylene phosphate, and a blend of such nonylphenol polyoxyethylene phosphate with polyoxyethylene tallowamine.

The composition of the present invention may also include non-ionic surfactant as additional emulsifier, which is a water-soluble, 20 to 250 ethylene glycol ether groups containing polyadducts of ethylene oxide and propylene oxide, ethylene diamino polypropylene glycol and alkyl polypropylene glycol with 1 to 10 carbon atoms in the alkyl moiety, the substances normally contain 1 to 5 ethylene glycol units per propylene glycol unit. Examples of non-ionic surfactants are nonylphenol polyethoxy ethanols, vegetable oil polyglycol ethers, polyadducts of ethylene oxide and propylene oxide, tributyl phenoxy polyethoxy ethanol (Ethylan NS 500), octyl phenoxy polyethoxy ethanol.

The emulsifiers are present in the composition in a range of about 1 to 30%, more preferably 2 to 20% of the total weight of the composition.

Solvents as used herein is a suitable water-immiscible solvents selected from the group consisting of aromatic hydrocarbons, aliphatic hydrocarbons, dialkylene glycol dialkyl ethers (diethylene glycol dimethyl ether), ketones such as acetone, MIBK, cyclohexanone, alkyl esters of acetic acid or mixtures thereo. Aromatic and aliphatic hydrocarbons such as hexane, cyclohexane, benzene, toluene, xylene, mineral oil or kerosene or substituted naphthalenes, polar aprotic solvents such as DMSO, DMF, 1-methylpyrrolidin-2-one (NMP) etc, mixtures of mono- and polyalkylated aromatics are commercially available under the registered trademarks Solvent C-9, Solvesso® and Shellsol® and Petrol Spezial® or combinations thereof.

Flumioxazin and Pendimethalin may be present in the composition or applied in any amounts relative to each other, to provide the enhanced or synergistic effect of the mixture. Flumioxazin and Pendimethalin may be present in the synergistic pesticidal composition in any suitable amount, and is generally present in an amount of from 1% to 15% by weight of the composition,. However, variables of the ratios of each of the active ingredients can be used and the selection of the particular amount is dependent upon many factors including, for example, type of formulations, the crop, disease sought to be controlled and environmental conditions. The selection of the proper quantity of active agent to be applied, however, is within the expertise of one skilled in the art.

Formulation includes water soluble concentrate (SL), an emulstifiable concentrate (EC), an emulsion (EW), a microemulsion (ME), a suspension concentrates (SC), an oil dispersions (OD), a flowable suspension (FS), water soluble powder (WS), water-dispersible granule (WDG), water-soluble granule (SG), a water-dispersible powder (WP), a water soluble powder (SP), a granule (GR), an encapsulated granule (CG), a fine granule (FG), a macrogranule (GG), an aqueous suspoemulsion (SE), capsule suspension (CS) and a microgranule (MG).

Preferably, the synergistic pesticidal composition can be formulated as Emulsifiable concentrate (EC).

The EC compositions of the present invention can be diluted with water or water solutions of agronomic compounds before use to produce a sprayable suspension composition which is used in treating plants or increasing plant growth, Dilution in water usually results in suspensions, emulsions, suspoemulsions or solutions of the agrochemical active ingredient at a concentration of at least 0.001 g/l.

A particular mode of administering the composition of the present invention is the administration to the aboveground parts of plants, in particular to the leaves thereof (leaf-application). The number of applications and the administered doses are chosen in accordance with the biological and climatic conditions of life of the causative agent. The antifungal compositions though, can also be applied to the soil and get into the plants through the root system (systemic activity), in case the locus of the plants is sprayed with a liquid composition or if the components are added to the soil in a solid formulation e.g. in the form of wettable powder (soil application).

When using the active compound combinations according to the invention, the application rate can be varied within a relatively wide range, depending on the kind of application. For the treatment of parts of plants, the active-compound combination application rates are generally between 0.1 and 10000 g/ha, preferably between 100 and 2500 g/ha. For seed dressing, the active compound combination application rates are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 20 g per kilogram of seed. For the treatment of the soil, the active-compound combination application rates are generally between 0.1 and 10000 g/ha preferably between 1 and 5000 g/ha.

The following examples describes the nature of the invention which are given only for the purpose of illustrating the present invention in more detail and are not limitative and relate to solutions, which have been particularly effective on bench scale.
EXAMPLES
Example 1: Composition of Flumioxazin 3.75% + Pendimethalin 27.5% EC:
S. No. Ingredients/Raw Materials Quantity (% w/w)
1. Pendimethalin @ 95% (b) 27.5 % 28.94
2. Flumioxazin @98.18% (b) 3.75% 3.819
3. 1-methylpyrrolidin-2-one (NMP) 25.0
4. Cyclohexanone 10.0
5. Linear dodecylbenzene sulphonate, calcium salt in 2-ethylexanol solution (Rhodacal 60/BER) 6.0
6. Polyalkoxylated butyl ether (Ethylan NS– 500 LQ) 6.0
7. Solvent naphtha (Solvent C-9) 20.24
Total 100

Manufacturing process:

NMP and cyclohexanone solvent was charged to a clean reactor vessel under stirring according to the batch size, followed by Pendimethalin technical and continue to stir for 15 minutes. Solvent C-9 was charged under continuous stirring and Flumioxazin technical was charged to the above step and continue to stir for 30 mins. Rhodacal 60/EBR to the above step and stir for 10 mins and Ethylan NS 500 LQ were charged and the contents stirred for 1 hour. The mixture was passed through 10µ sieve filter paper and the material was collected and packed.

Field Efficacy trials of Flumioxazin and Pendimethalin EC
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 tonnes. Successful weed control is most important factor for fruitful soybean production because losses due weeds have been one of the major limiting factors in soybean production. Weeds compete with crop 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 to use herbicides.

The field studies were conducted to compare the weed controlling activity of the combination of Flumioxazin and Pendimethalin EC. The active ingredient Flumioxazin in the combination belongs to chemical family “N-phenylphthalimides” 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 and 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 Dinebra retroflexa. Trials were conducted with randomized block design with net plot size of 5m x 6m. 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 15 days after application. These observations are to be taken from entire plot.

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

Table 1: Table 1 demonstrates synergy on weeds using the combination of Flumioxazin and Pendimethalin EC. The field trials were carried out in India at various locations. The percentage efficacy was calculated after 15 days of application. The target weeds were Commelina benghalensis and Commelina communis and the results are recorded in the tables 1 below:

Active Dose (GAH) % Weed Control of Commelina benghalensis % Weed Control of Commelina communis
Flumioxazin SC 120 55 55
Pendimethalin EC 880 0 10
Flumioxazin + Pendimethalin EC (Example 1) 120 + 880 80 75

The results in table 1 clearly demonstrates synergy between Flumioxazin and Pendimethalin against weeds like, Commelina benghalensis and Commelina communis.

Table 2: Table 2 demonstrates synergy on weeds using the combination of Flumioxazin and Pendimethalin. The field trials were carried out in India at various locations. The percentage efficacy was calculated after 15 days of application. The target weeds were Echinochloa colonum and Dinebra retroflexa and the results are recorded in the tables 2 below.

Active Dose (GAH) % Weed Control of Echinochloa colonum % Weed Control of Dinebra retroflexa
Flumioxazin SC 120 55 90
Pendimethalin EC 880 80 50
Flumioxazin + Pendimethalin EC (Example 1) 120 + 880 95 100

The results in table 2 clearly demonstrates efficacy of Flumioxazin and Pendimethalin ECagainst weeds like Echinochloa colonum and Dinebra retroflexa.

Table 3: Table 3 demonstrates synergy on weeds using the combination of Flumioxazin and Pendimethalin. The field trials were carried out in India at various locations. The percentage efficacy was calculated after 15 days of application. The target weeds were Acalypha indica and Digera arvensis and the results are recorded in the tables 3 below.

Active Dose (GAH) % Weed Control of Acalypha indica % Weed Control of Digera arvensis
Flumioxazin SC 120 70 80
Pendimethalin EC 880 0 60
Flumioxazin + Pendimethalin EC (Example 1) 120 + 880 75 95

The results in table 3 clearly demonstrates efficacy of Flumioxazin and Pendimethalin against weeds like, Acalypha indica and Digera arvensis.

,CLAIMS:WE CLAIM:
1. A synergistic herbicidal emulsifiable concentrate composition comprising:
a) phenylphthalimide,
b) dinitroaniline, and
c) agrochemical auxiliaries.

2. The composition as claimed in claim 1, wherein said phenylphthalimide herbicide is Flumioxazin and dinitroaniline herbicide is Pendimethalin.

3. The composition as claimed in claims 1 and 2, wherein said emulsifiable concentrate composition comprising:
a) Flumioxazin,
b) Pendimethalin,
c) emulsifiers, and
d) solvents.

4. The composition as claimed in claim 3, wherein said emulsifiers are selected from linear dodecylbenzene sulphonate, calcium salt in 2-ethylexanol solution, polyalkoxylated butyl ether or combinations thereof.

5. The composition as claimed in claim 3, wherein said solvents are selected from water-immiscible solvents selected from the group consisting of aromatic hydrocarbons, liphatic hydrocarbons, dialkylene glycol dialkyl ethers, ketones such as acetone, MIBK, cyclohexanone, alkyl esters of acetic acid or mixtures thereo, aromatic and aliphatic hydrocarbons such as hexane, cyclohexane, benzene, toluene, xylene, mineral oil or kerosene or substituted naphthalenes, polar aprotic solvents such as DMSO, DMF, 1-methylpyrrolidin-2-one (NMP) etc, mixtures of mono- and polyalkylated aromatics such as solvent naphtha (Solvent C-9) or combinations thereof.

6. The composition as claimed in claims 1 - 5, wherein said emulsifiable concentrate composition comprising:
a) Flumioxazin in a range of 1% to 15% (w/w),
b) Pendimethalin in a range of 1% to 15% (w/w),
c) linear dodecylbenzene sulphonate, calcium salt in 2-ethylexanol solution in a range of 1% to 20% (w/w),
d) polyalkoxylated butyl ether in a range of 1% to 10% (w/w),
e) 1-methylpyrrolidin-2-one in a range of 1% to 30% (w/w),
f) cyclohexanone in a range of 1% to 20% (w/w), and
g) solvent naphtha (Petroleum) in a range of 1% to 30% (w/w).

7. The process for the preparation of composition as claimed in claim 1, wherein said process comprising the steps of:
a) weighing all the active ingredients and agrochemical auxiliaries,
b) mixing all the ingredients under stirring, and
c) homogenizing the obtained material, filtering and packing.

8. The process for the preparation of composition as claimed in claim 6, wherein said process comprising the steps of:
a) weighing and mixing Pendimethalin, Flumioxazin, linear dodecylbenzene sulphonate, calcium salt in 2-ethylexanol solution, polyalkoxylated butyl ether, of 1-methylpyrrolidin-2-one, cyclohexanone and solvent naphtha under stirring and
b) homogenizing the obtained material, filtering and packing.

Dated this Twenty Fourth (24th) day of August, 2021

__________________________________
Dr. S. Padmaja
Agent for the Applicant
IN/PA/883

Documents

Orders

Section Controller Decision Date
15 MASTHAN VALI NAMA 2024-11-29
25(1) MASTHAN VALI NAMA 2024-11-29

Application Documents

# Name Date
1 202041036779-Annexure [31-10-2024(online)].pdf 2024-10-31
1 202041036779-PROVISIONAL SPECIFICATION [26-08-2020(online)].pdf 2020-08-26
2 202041036779-POWER OF AUTHORITY [26-08-2020(online)].pdf 2020-08-26
2 202041036779-Written submissions and relevant documents [31-10-2024(online)].pdf 2024-10-31
3 202041036779-FORM 1 [26-08-2020(online)].pdf 2020-08-26
3 202041036779-ANY SUPPORTING DOCUMENT [14-10-2024(online)].pdf 2024-10-14
4 202041036779-Proof of Right [24-08-2021(online)].pdf 2021-08-24
4 202041036779-Correspondence to notify the Controller [10-10-2024(online)].pdf 2024-10-10
5 202041036779-PreGrant-HearingNotice-(HearingDate-16-10-2024)-1500.pdf 2024-09-16
5 202041036779-FORM 3 [24-08-2021(online)].pdf 2021-08-24
6 202041036779.Pregrant Opposition.pdf 2024-06-05
6 202041036779-ENDORSEMENT BY INVENTORS [24-08-2021(online)].pdf 2021-08-24
7 202041036779-FORM-26 [08-01-2024(online)].pdf 2024-01-08
7 202041036779-COMPLETE SPECIFICATION [24-08-2021(online)].pdf 2021-08-24
8 202041036779-FORM-26 [13-10-2022(online)].pdf 2022-10-13
8 202041036779-FORM 18 [07-03-2022(online)].pdf 2022-03-07
9 202041036779-FER.pdf 2022-03-14
9 202041036779-OTHERS [16-09-2022(online)].pdf 2022-09-16
10 202041036779-FER_SER_REPLY [20-04-2022(online)].pdf 2022-04-20
10 202041036779-PRE GRANT OPPOSITION DOCUMENT [16-09-2022(online)].pdf 2022-09-16
11 202041036779-CORRESPONDENCE [20-04-2022(online)].pdf 2022-04-20
11 202041036779-PRE GRANT OPPOSITION FORM [16-09-2022(online)].pdf 2022-09-16
12 202041036779-Annexure [15-09-2022(online)].pdf 2022-09-15
12 202041036779-COMPLETE SPECIFICATION [20-04-2022(online)].pdf 2022-04-20
13 202041036779-CLAIMS [20-04-2022(online)].pdf 2022-04-20
13 202041036779-Written submissions and relevant documents [15-09-2022(online)].pdf 2022-09-15
14 202041036779-ABSTRACT [20-04-2022(online)].pdf 2022-04-20
14 202041036779-Correspondence to notify the Controller [09-09-2022(online)].pdf 2022-09-09
15 202041036779-US(14)-HearingNotice-(HearingDate-14-09-2022).pdf 2022-08-30
16 202041036779-ABSTRACT [20-04-2022(online)].pdf 2022-04-20
16 202041036779-Correspondence to notify the Controller [09-09-2022(online)].pdf 2022-09-09
17 202041036779-Written submissions and relevant documents [15-09-2022(online)].pdf 2022-09-15
17 202041036779-CLAIMS [20-04-2022(online)].pdf 2022-04-20
18 202041036779-COMPLETE SPECIFICATION [20-04-2022(online)].pdf 2022-04-20
18 202041036779-Annexure [15-09-2022(online)].pdf 2022-09-15
19 202041036779-CORRESPONDENCE [20-04-2022(online)].pdf 2022-04-20
19 202041036779-PRE GRANT OPPOSITION FORM [16-09-2022(online)].pdf 2022-09-16
20 202041036779-FER_SER_REPLY [20-04-2022(online)].pdf 2022-04-20
20 202041036779-PRE GRANT OPPOSITION DOCUMENT [16-09-2022(online)].pdf 2022-09-16
21 202041036779-FER.pdf 2022-03-14
21 202041036779-OTHERS [16-09-2022(online)].pdf 2022-09-16
22 202041036779-FORM 18 [07-03-2022(online)].pdf 2022-03-07
22 202041036779-FORM-26 [13-10-2022(online)].pdf 2022-10-13
23 202041036779-COMPLETE SPECIFICATION [24-08-2021(online)].pdf 2021-08-24
23 202041036779-FORM-26 [08-01-2024(online)].pdf 2024-01-08
24 202041036779-ENDORSEMENT BY INVENTORS [24-08-2021(online)].pdf 2021-08-24
24 202041036779.Pregrant Opposition.pdf 2024-06-05
25 202041036779-PreGrant-HearingNotice-(HearingDate-16-10-2024)-1500.pdf 2024-09-16
25 202041036779-FORM 3 [24-08-2021(online)].pdf 2021-08-24
26 202041036779-Proof of Right [24-08-2021(online)].pdf 2021-08-24
26 202041036779-Correspondence to notify the Controller [10-10-2024(online)].pdf 2024-10-10
27 202041036779-FORM 1 [26-08-2020(online)].pdf 2020-08-26
27 202041036779-ANY SUPPORTING DOCUMENT [14-10-2024(online)].pdf 2024-10-14
28 202041036779-Written submissions and relevant documents [31-10-2024(online)].pdf 2024-10-31
28 202041036779-POWER OF AUTHORITY [26-08-2020(online)].pdf 2020-08-26
29 202041036779-PROVISIONAL SPECIFICATION [26-08-2020(online)].pdf 2020-08-26
29 202041036779-Annexure [31-10-2024(online)].pdf 2024-10-31

Search Strategy

1 Flumioxazin;Pendimethalin;dodecylbenzenesulphonate-GooglePatentsE_14-03-2022.pdf