WO2014181281A1

WO2014181281A1 - Herbicidal mixture of imazethapyr and propaquizafop

Info

Publication number: WO2014181281A1
Application number: PCT/IB2014/061291
Authority: WO
Inventors: Josef GOLDSHMIDT
Original assignee: Quena Plant Protection N.V.
Priority date: 2013-05-08
Filing date: 2014-05-08
Publication date: 2014-11-13
Also published as: AR096214A1; RU2656400C2; BR112015028146A2; RU2015151447A; UA119849C2

Abstract

A synergistic herbicidal mixture for controlling undesired vegetation comprising imazethapyr and propaquizafop, esters, salts and/or combination thereof.

Description

HERBICIDAL MIXTURE OF IMAZETHAPYR AND PROPAQUIZAFOP

CROSS-REFERENCE TO RELATED APPLICATIONS

The present application claims the benefit of Indian Provisional Application No. 524/KOL/2013, filed May 8, 2013, which is hereby incorporated by reference herein in its entirety.

FIELD

The present subject matter relates to a herbicidal mixture for controlling undesired vegetation. Specifically, the present subject matter relates to a herbicidal mixture comprising a synergistic combination of propaquizafop and imazethapyr.

BACKGROUND

The control of undesired vegetation is extremely important in order to achieve high crop efficiency. In many cases, herbicides have an effect against a spectrum of weeds; however, these herbicides may not be effective certain type of other weeds, which may also be present in the crop to be protected. Therefore, there is a strong need for mixing two or more herbicides.

Mixtures of selected herbicides have several advantages over the use of a single herbicide including (a) an increase in the spectrum of weeds controlled or an extension of weed control over a longer period of time, (b) an improvement in crop safety by using minimum doses of selected herbicides applied in combination rather than a single high dose of one herbicide and (c) a delay in the appearance of resistant weed species to selected herbicides {Int. J. Agri. Biol., Vol. 6, No. 1, 2004, pages 209-212).

However, the activity and selectivity behavior of a mixture is difficult to predict since the behavior of each single herbicide in the mixture is often affected by the presence of the other(s) and the activity of the mixture may also vary considerably depending on chemical character, plant species, growth stage, and environmental conditions, mostly this practice results in reduced activity of the herbicides in the mixture.

Propaquizafop, ((R)-2- [[( 1 -methylethylidene)amino] oxyjethyl 2- [4- [(6-chloro-2- quinoxalinyl)oxy]phenoxy]propanoate), disclosed in US4545807, is a Fatty acid synthesis inhibitor which inhibits acetyl CoA carboxylase (ACCase). It is a systemic post-emergence herbicide absorbed by foliage and roots, and translocated throughout the plant. Propaquizafop is used for the control of a wide range of annual and perennial grasses (including Sorghum halepense, Agropyron repens and Cynodon dactylon) in soya beans, cotton, sugar beet, potatoes, peanuts, peas, oilseed rape and vegetables.

Imazethapyr, (R5)-5-ethyl-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl) nicotinic acid, disclosed in US 4,798,619, is a branched chain amino acid synthesis (ALS or AHAS) inhibitor. Hence reduces levels of valine, leucine and isoleucine, leading to disruption of protein and DNA synthesis. Imazethapyr is a systemic herbicide, absorbed by the roots and foliage. Imazethapyr control many major annual and perennial grass and broad leaved weeds.

According to Herbicide Mixture Compatibility Chart, published by the government of Western Australia, Department of agriculture and food Tank, mixing imazethapyr and propaquizafop is not recommended. The chart teaches that excessive crop damage or reduction in weed control may occur by the combination of both herbicides

[www.agric.wa.gov.au/objtwr/imported_assets/content/pw/weed/herbicide%20compatib ility%20chart.pdfj.

In addition, Paul F. Myers and Harold D. Coble {Weed Technology Vol. 6, No. 2, 1992, pp. 333-338) teaches that tank-mix combinations of imazethapyr with clethodim, fluazifop-P, quizalofop, or sethoxydim, all inhibitors of acetyl CoA carboxylase similar to propaquizafop, resulted in an antagonistic interaction.

SUMMARY

The subject matter relates to a herbicidal mixture comprising imazethapyr and propaquizafop, esters, salts and/or combination thereof. According to an embodiment, the weight ratio of imazethapyr to propaquizafop may be from 20: 1 to 1:20 In a specific embodiment, the weight ratio of imazethapyr to propaquizafop may be from 5: 1 to 1 :5.

According to an embodiment, the compounds of the mixture may be applied jointly or in a succession. The application rate of the mixture may be from 0.1 liter/ha to 10 liter/ha. In a specific embodiment, the application rate of the mixture may be 1.25 liter/ha. The mixture may be applied in an amount of 125 g/ha.The amount of imazethapyr to be applied may be 75 g/ha and the amount of propaquizafop may be 50 g/ha.

According to another aspect of the described subject matter provided herein, a composition comprising imazethapyr and propaquizafop, esters, salts or combination thereof and at least one agriculturally acceptable carrier. The composition may further include at least one surfactant, solid diluent, liquid diluent, or a combination thereof.

According to yet another aspect there is provided a method of controlling undesired vegetation comprising applying to the locus of the undesired vegetation a herbicidally effective amount of the mixture comprising imazethapyr, propaquizafop esters, salts and/or combination thereof. The crop may be selected from the group consisting of soybeans, blackgram, peanuts, green gram, pigeon pea, beans, field peas and cluster beans. In an embodiment the mixture may be applied in an amount of 1 to 500 g/ha. In a preferred embodiment, the mixture may be applied in an amount of 125 g/ha.

The undesired vegetation may be selected from the group consisting of

Echinochloa Colona, Dinebra Arabica, Cynotis sp, Eleusine Indica, Cynodon Dactylon, Euphorbia Hirta, Amaranthus Viridis, Digeria Arvensis, Digera sp., Panicum sp., Phyllanthus sp, Commelina benghalensis L, Parthenium, Trianthema Portulacasturm, Cleome viscosa, Digera arvensis, Parthenium hysterophorus, Cynadon dactylone, Commelina bengalensis and Dinebra sp., Portulaca sp., Trianthima sp., Dactyloctenium aegyptium, Corchprus sp., Trianthema monogyna, Brachiaria sp.

According to yet another aspect there is provided a method of controlling undesired vegetation comprising applying to the locus of the undesired vegetation a herbicidally effective amount of the composition comprising imazethapyr, propaquizafop esters, salts and/or combination thereof.

According to yet another aspect there is provided a synergistic mixture comprising imazethapyr and propaquizafop, esters, salts and/or combination thereof.

DETAILED DESCRIPTION

All technical and scientific terms used herein have the same meanings as commonly understood by someone ordinarily skilled in the art to which the present subject matter belongs. The following definitions are provided for clarity. As used herein the term "crop" includes reference to whole plant, plant organ (e.g., leaves, stems, twigs, roots, trunks, limbs, shoots, fruits etc.), or plant cells.

As used herein the term "locus" includes not only areas where weeds may already be growing, but also areas where weeds have yet to emerge, and also to areas under cultivation.

As used herein the term "agriculturally acceptable carrier" means carriers of which are known and accepted in the art for the formation of formulations for agricultural or horticultural use.

The term "surfactant," as used herein, refers to an agriculturally acceptable material which imparts emulsifiability, stability, spreading, wetting, dispersibility or other surface-modifying properties.

The term "a" or "an" as used herein includes the singular and the plural, unless specifically stated otherwise. Therefore, the term "a," "an," or "at least one" can be used interchangeably in this application.

Throughout the application, descriptions of various embodiments use the term

"comprising;" however, it will be understood by one of skill in the art, that in some specific instances, an embodiment can alternatively be described using the language "consisting essentially of or "consisting of."

For the purposes of better understanding the present teachings and in no way limiting the scope of the teachings, unless otherwise indicated, all numbers expressing quantities, percentages or proportions, and other numerical values used in the specification and claims, are to be understood as being modified in all instances by the term "about." Accordingly, unless indicated to the contrary, the numerical parameters set forth in the following specification and attached claims are approximations that may vary depending upon the desired properties sought to be obtained. At the very least, each numerical parameter should at least be construed in light of the number of reported significant digits and by applying ordinary rounding techniques.

The present subject matter relates to a herbicidal mixture comprising imazethapyr and propaquizafop, esters, salts and/or combination thereof.

An embodiment relates to a synergistic herbicidal mixture comprising imazethapyr and propaquizafop, esters, salts and/or combination thereof. In an embodiment, the weight ratio of imazethapyr to propaquizafop in the mixture may be from about 50: 1 to 1 :50. In another embodiment, the weight ratio of imazethapyr to propaquizafop may be from about 20: 1 to 1:20. In yet another embodiment, the weight ratio of imazethapyr to propaquizafop may be from about 5: 1 to 1 :5. In yet another embodiment, the weight ratio of imazethapyr to propaquizafop may be from about 1.75: 1 to 1 : 1.75. In yet another embodiment, the weight ratio of imazethapyr to propaquizafop may be from about 1.5: 1 to 1 : 1.5. In yet another embodiment, the weight ratio of imazethapyr to propaquizafop may be from about 1.4: 1 to 1 :1.4. In yet another embodiment, the weight ratio of imazethapyr to propaquizafop may be from about 1.2: 1 to 1: 1.2.

In a specific embodiment, the weight ratio of imazethapyr to propaquizafop may be about 1.1 :1.

In another embodiment, a composition comprising imazethapyr and propaquizafop including esters and salts thereof and an agriculturally acceptable carrier, is provided.

In yet another embodiment, the composition comprising at least one additional component selected from the group of surfactants, solid diluents and liquid diluents.

The herbicidal compositions and herbicidal mixtures may be applied jointly or in a succession.

The compositions may include additional other crop protection agents, for example pesticides, safeners or agents for controlling phytopathogenic fungi or bacteria.

In an embodiment, the herbicidal mixture may be applied in an amount of about 0.1 to 500 liter/ha. In yet another embodiment, the herbicidal mixture may be applied in an amount of about 0.1 to 100 liter/ha. In another embodiment, the herbicidal may be applied in an amount of about 0.1 to 10 liter/ha. In a specific embodiment, the mixture may be applied in an amount of about 1.25 liter/ha (equal to 0.50 liter/acre). In yet another specific embodiment, the mixture may be applied in an amount of about 1.35 liter/ha (equal to 0.55 liter/acre). In yet another specific embodiment, the mixture may be applied in an amount of about 1.50 liter/ha (equal to 0.60 liter/acre). In a specific embodiment, the mixture may be applied in an amount of about 2.00 liter/ha (equal to 0.80 liter/acre). In yet another specific embodiment, the mixture may be applied in an amount of about 2.25 liter/ha (equal to 0.90 liter/acre). In yet another specific embodiment, the mixture may be applied in an amount of about 2.50 liter/ha (equal to 1.00 liter/acre).

According to an embodiment, the herbicidal mixture may be applied in an amount of about 1 to 1000 g/ha. In another embodiment, the herbicidal mixture may be applied in an amount of about 1 to 500 g/ha. In a specific embodiment, the mixture may be applied in an amount of about 125 g/ha. Correspondingly, the amount of imazethapyr is about 75 g/ha and propaquizafop is about 50 g/ha.

Additionally, a method of controlling undesired vegetation comprising applying to the locus of the undesired vegetation a herbicidally effective amount of a mixture of imazethapyr and propaquizafop, esters, salts and/or combination thereof, is provided.

The mixtures and/or the herbicidal compositions may be applied pre-plant incorporated, pre- or post-emergence.

In an embodiment, the mixture may be applied on crops which include soybeans, blackgram, peanuts, green gram, pigeon pea, cluster beans, field peas, mung beans, dry beans, peanuts, groundnuts, snap bean, alfalfa, lettuce, beans. In a specific embodiment the crop includes soybeans, groundnuts, blackgram, peanuts, green gram, pigeon pea, beans, field peas and cluster beans. In an embodiment, the mixture may be applied on tolerant or resistant mutants or transgenic crops plants such as soybean, and etc.

In an embodiment, the undesired vegetation may include Hibiscus trionum,

Lolium perenne L. ssp. multiflorum (Lam.) Husnot, Sida rhombifolia L., Anoda cristata (L.) Schlecht., Lamium spp. L, Cyperus di formis L., Croton sperrsifeorus, Nicandra physalodes, Chenopodium album L., Echinochloa colona, Amaranthus viridis, Hordeum murinum subsp. Leporinum, Sisymbrium orientate, Ipomoea plebeia, Cerastium vulgatum, Bifora radians Bieb., Echinochloa crus-galli (L.) Beauv. , Digera spp., Digera arvensis, Arctotheca calendula (L.) Levyns., Cynadon dactylone, Commelina benghalensis L., Eragrostis pilosa (L.) Beauv., Amaranthus retroflexus L., Amaranthus sp., Euphorbia hirta L., Datura wrightii Regel, Capsella bursa-pastoris (L.) Medik., Emex australis, Urtica dioica L., Veronica hederifolia L., Erodium cicutarium, Juncus tenuis Willd., Juncus bufonius, Lythrum hyssopifolia, Rapistrum rugosum (L.) AIL, Salvia reflexa, Buglossoides arvensis syn Lithospermum arvens, Xanthium pungens, Ribes divaricatum, Cyperus rotundus, Raphanus raphanistrum L., Echium plantagineum, Polygonumaviculare and Polygonum arenastrum, Parthenium, Lactuca serriola L., Acanthospermum, Galium tricornutum Dandy, Amsinckia calycina (Moris) Chater, Amsinckia intermedia Fischer & C.Meyer, Amsinckia lycopsoides (Lehm.) Lehm., Triticum sp., Hordeum vulgare, Alopecurus myosuroides Huds., Lolium sp., Elymus repens, Bromus sterilis, Xanthium Spinosum, Datura ferox, Dinebra Arabica, Eleusine indica, Cynodon dactylon, Euphorbia Hirta, Trianthema Portulacasturm, Amaranthus deflexus, Amaranthus hybridus L., Polygonum, Persicaria maculosa, Synapis arvensis, Abutilon theophrasti Medik., Ambrosia artemisiifolia L., Solanum ptychanthum, Xanthium strumarium L., Polygonum convolvulus, Alopecurus sp., Bromus madritensis sp., Panicum sp., Hordeum jubatum sp., Setaria sp., Panicum capillare L., Panicum miliaceum L., Digitaria sp., Cyperus esculentus L., Acanthospermum hispidum DC, Cynotis sp, Tradescantia fluminernsis, Galinsoga sp., Portulaca oleracea L., Alternanthera caracasana, Tribulus zeyheri, Acanthospermum australe, Acanthospermum glabratum, Cleome monophylla, Phyllanthus sp., Flaveria bidentis, Galinsoga parviflora, Soliva sessilis, Bidens pilosa, Parnassia palustris, Eragrostis, Ipomeas sp., Hierochloe odorata, Anthoxanthum nitens, Rottboellia cochinchinensis L., Schkuhria Bonariensi L., Sorghum halepense, Devil thorn, Zea mays L, Cleome viscosa, Parthenium hysterophorus, Commelina bengalensis, Dinebra sp., Portulaca sp., Trianthima sp., Dactyloctenium aegyptium, Corchprus sp., Trianthema monogyna and Brachiaria sp.

In a specific embodiment, the undesired vegetation may include Echinochloa Colona, Dinebra Arabica, Cynotis sp, Eleusine Indica, Cynodon Dactylon, Euphorbia Hirta, Amaranthus Viridis, Digeria Arvensis, Digera sp., Panicum sp., Phyllanthus sp, Commelina benghalensis L, Parthenium, Trianthema Portulacasturm, Cleome viscosa, Digera arvensis, Parthenium hysterophorus, Cynadon dactylone, Commelina bengalensis and Dinebra sp., Portulaca sp., Trianthima sp., Dactyloctenium aegyptium, Corchprus sp., Trianthema monogyna, Brachiaria sp.

The described compositions may be made at the time of use, or diluted, or else they can be concentrated compositions, or so-called "ready-to-use" compositions, that is to say, ready for marketing. In an embodiment, the formulation may be obtained by combining a synergistic amount of the active ingredients with an agriculturally acceptable carrier, a surfactant or other application-promoting adjuvant customarily employed in formulation technology.

In yet another embodiment, the composition may be employed in any conventional form, for example, in the form of a twin pack, or as emulsion concentrates (EC), microemulsion concentrates (MEC), suspension concentrates (SC), soluble concentrates (SL), suspoemulsion (SE), oil dispersions (OD), water dispersible granules (WDG), water soluble granules (SG) and wettable powders (WP). Such compositions can be formulated using with agriculturally acceptable carriers, surfactants or other application-promoting adjuvants customarily employed in formulation technology and formulation techniques that are known in the art.

In a specific embodiment, the composition of imazethapyr and propaquizafop is an emulsion concentrate, preferably a microemulsion.

In an embodiment, the amount of the mixture of active ingredient in the composition may be about 0.1-99 wt. , specifically about 0.1-95 wt. , more specifically about 0.1-90 wt. , based on the total weight of the composition. In another embodiment, the amount of the mixture of active ingredient in the composition may be about 0.1-50 wt , specifically about 0.1-25 wt. , more specifically about 0.1-10 wt. , based on the total weight of the composition.

Examples of suitable liquid carriers to be used in the composition may include water, aromatic hydrocarbons such as alkylbenzenes and alkylnaphthalenes, alcohols such as methanol, cyclohexanol and decanol, ethylene glycol, polypropylene glycol and dipropropylene glycol, N,N-dimethylformamide, dimethylsulfoxide, N- alkylpyrrolidone, paraffins, oils of olive, castor, linseed, tung, sesame, corn, peanut, cotton-seed, soybean, rape-seed and coconut, fatty acid esters, ketones such as cyclohexanone, 2-heptanone, isophorone and 4-hydroxy-4-methyl-2-pentanone and the like.

Examples of suitable solid carriers to be used in the composition may include mineral earths such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, sodium carbonate and bicarbonate, and sodium sulfate, ground synthetic materials, fertilizers, such as, for example, ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders and other solid carriers.

Examples of suitable surfactants include non-ionic, anionic, cationic and ampholytic types such as alkoxylated fatty alcohols, ethoxylated polysorbate (e.g. tween 20), ethoxylated castor oil, lignin sulfonates, fatty acid sulfonates (e.g. lauryl sulfonate), phosphate esters such as phosphate esters of alcohol alkoxylates, phosphate esters of alkylphenol alkoxylates and phosphate esters of styrylphenol ethoxylates, condensates of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensates of naphthalene or of naphthalenesulfonic acid with phenol and formaldehyde, alkylarylsulfonates, ethoxylated alkylphenols and aryl phenols, polyalkylene glycols and sorbitol esters.

Other ingredients, such as wetting agents, anti-foaming, adhesives, neutralizers, thickeners, binders, sequestrants, stabilizers, solubilizer, salts, fertilizers or anti-freeze agents, may also be added to the disclosed compositions.

In another embodiment, a kit comprising the herbicidal mixture as described herein, or components thereof, is provided. Such kits may comprise, in addition to the aforementioned active components, one or more additional active and/or inactive ingredients, either within the provided herbicidal composition or separately. Certain kits comprise imazethapyr, propaquizafop, each in a separate container, and each optionally combined with a carrier.

A synergistic effect exists wherever the action of a combination of active components is greater than the sum of the action of each of the components alone. Therefore, a synergistically effective amount (or an effective amount of a synergistic composition or combination) is an amount that exhibits greater pesticidal activity than the sum of the pesticidal activities of the individual components.

In the field of agriculture, it is often understood that the term "synergy" is as defined by Colby S. R. in an article entitled "Calculation of the synergistic and antagonistic responses of herbicide combinations" published in the journal Weeds, 1967, 15, p. 20-22, incorporated herein by reference in its entirety. The action expected for a given combination of two active components can be calculated as follows: in which E represents the expected percentage of pesticidal control for the combination of the two pesticides at defined doses (for example equal to x and y respectively), X is the percentage of herbicidal control observed by imazethapyr at a defined dose (equal to x) and Y is the percentage of herbicidal control observed by propaquizafop at a defined dose (equal to y). When the percentage of herbicidal control observed for the combination is greater than the expected percentage, there is a synergistic effect, when the percentage of control observed for the combination is equal to the expected percentage, there is an additive effect and wherein the percentage of herbicidal control observed for the combination is lower than the expected percentage, there is an antagonistic effect.

EXPERIMENTAL DETAILS

Formulation Example

One exemplary embodiment of the ready mix emulsion concentrate formulation is illustrated in Table 1, below:

TABLE 1

d= 1.068 g/1.

The above formulation was prepared by forming a mixture comprising 37.5 g of imazethapyr, the surfactants, the additives and dipropylene glycol, propylene glycol and water as solvents. Afterwards, a premix of 25 g of propaquizafop dissolved in Solgad 200 ULN was added to the mixture. This was then stirred until a homogeneous mixture was obtained.

Experiments

The experiments were conducted by tank mixing commercially available Agil (propaquizafop 10% EC, 100 gr/L) and commercially available Weedlock (imazethapyr 10% SL, 100 gr/L) on soybean, black gram, ground nut (peanut), red gram (pigeon peas), green gram, beans, field peas and cluster beans (tables 2-10) in different application rates.

Applications were made with a Knapsack sprayer fitted with Flat fan nozzle for 5 the application of herbicides. Experiment design was in random blocks with three

replication and nine treatments.

Species wise weed count recorded at 15 and 30 DAA (Days After Application) by using 0.25 m quadrant treatment wise in minimum 3 places randomly selected in the plot / replication. The average of each variable was used together with the sum of 10 all the variables per plot to calculate the percentage of control.

The % control observed was calculated as follows:

% control observed =

Mean weed count in untreated control -Mean weed count in treated plot

* 100

Mean weed count in untreated control

EXAMPLE 1 : Tank mix of Propaquizafop + Imazethapyr on Soybean

TABLE 2

Tank mix of Propaquizafop + Imazethapyr on Soybean

% control % control

Colby Ratio o/e observed expected

Application

AI rate 15DAA 30DAA 15DAA 30DAA 15DAA 30DAA

(ml/Acre)

Propaquizafop 200 64.02 67.08

Propaquizafop 250 67.78 74.58

Imazethapyr 300 65.69 66.67

Imazethapyr 350 66.53 66.25

Propaquizafop + Imazethapyr 200+300 95.40 98.33 87.65 89.03 1.09 1.10

Propaquizafop + Imazethapyr 200+350 96.65 98.33 87.96 88.89 1.10 1.11

Propaquizafop + Imazethapyr 250+300 93.72 91.25 88.95 91.53 1.05 1.00

Propaquizafop + Imazethapyr 250+350 92.05 92.50 89.22 91.42 1.03 1.01 DAA means days after treatment.

The trial detailed in Table 2 was conducted on Soybean crop in the district of Singauda, Madhya Pradesh (India). The sowing was done during first week of July with 5 a variety JS9560. Phenological Status: Vegetative growth 20 DAS, Design & Plot size:

RBD & 36 Sq.mt. The weeds that have been controlled include Dinebra, Echinochloa colona, Eleusine indica, Cynadon dactylone, Cynotis sp, Commelina bengalensis, Alternanthera, and Parthenium.

10 EXAMPLE 2: Tank mix of Propaquizafop + Imazethapyr on Black Gram

TABLE 3

DAA means days after treatment.

The trial detailed in Table 3 was conducted on Black gram in the district of Kaza, Guntur (Andhra Pradesh, India). The sowing was done during second week of July with a variety LBG756. Phenological Status: Vegetative growth 20 DAS, Design & Plot size: RBD & 20 Sq.mt. The weeds that have been controlled include Echinochloa colona, Panicum sp, Amaranthus sp. and Phyllanthus sp. EXAMPLE 3: Tank mix of Propaquizafop + Imazethapyr on Ground nut (Peanut)

TABLE 4

DAA means days after treatment.

5 The trial detailed in Table 4 was conducted on Peanut in the district of Koppaka,

West Godavari (Andhra Pradesh, India). The sowing was done during second week of August with a variety K20. Phenological Status: Vegetative growth 20 DAS, Design & Plot size: RBD & 20 Sq.mt. The weeds that have been controlled include Echinochloa colona, Trianthema portulcastrum, Cleome viscosa, Digera arvensis, and Parthenium 10 hysterophorus.

EXAMPLE 4: Tank mix of Propaquizafop + Imazethapyr on Pigeon peas (Red Gram)

TABLE 5

DAA means days after treatment.

5 The trial detailed in Table 5 was conducted on Red gram in the district of

Amaravati (Maharashtra, India). The sowing was done during third week of October with a variety Maruti. Phenological Status: Vegetative growth 20 DAS, Design & Plot size: RBD & 30 Sq.mt. The weeds that have been controlled include Echinochloa colona, Panicum sp, Amaranthus sp and Phyllanthus sp.

0

EXAMPLE 5: Tank mix of Propaquizafop + Imazethapyr on Green gram

TABLE 6

Tank mix of Propaquizafop + Imazethapyr on Green Gram

% control % control

Colby Ratio o/e observed expected

Application

AI rate 15DAA 30DAA 15DAA 30DAA 15DAA 30DAA

(ml/Acre) Propaquizafop 200 70.98 70.00

Propaquizafop 250 68.30 72.27

Imazethapyr 300 67.41 68.18

Imazethapyr 350 64.29 65.45

Propaquizafop + Imazethapyr 200+300 94.64 98.18 90.54 90.45 1.05 1.09

Propaquizafop + Imazethapyr 200+350 94.64 98.18 89.64 89.64 1.06 1.10

Propaquizafop + Imazethapyr 250+300 93.30 95.45 89.67 91.18 1.04 1.05

Propaquizafop + Imazethapyr 250+350 92.86 95.45 88.68 90.42 1.05 1.06

DAA means days after treatment.

The trial detailed in Table 6 was conducted on Green gram in the district of Mogalauru, Krishna (Andhra Pradesh, India). The sowing was done during first week of 5 July with a local variety. Phenological status: vegetative growth 20 DAS. Design & Plot

size: RBD & 20 Sq.mt. The weeds that have been controlled include Echinochloa colona, Panicum sp, Amaranthus sp and Phyllanthus sp.

EXAMPLE 6: Tank mix of Propaquizafop + Imazethapyr on Ground nut (Peanut)

10 TABLE 7

Tank mix of Propaquizafop + Imazethapyr on Ground nut

% control % control

Colby Ratio o/e observed expected

Application

AI rate 15DAA 30DAA 15DAA 30DAA 15DAA 30DAA

(ml/Acre)

Propaquizafop 200 54.07 61.96

Propaquizafop 250 58.14 65.76

Imazethapyr 300 56.40 62.50

Imazethapyr 350 54.65 61.96

Propaquizafop + Imazethapyr 200+300 93.60 97.83 79.97 85.73 1.17 1.14

Propaquizafop + Imazethapyr 200+350 94.77 97.83 79.17 85.53 1.20 1.14

Propaquizafop + Imazethapyr 250+300 89.53 92.39 81.75 87.16 1.10 1.06 Propaquizafop + Imazethapyr 250+350 90.12 92.93 81.02 86.97 1.11 1.07

DAA means days after treatment.

The trial detailed in Table 7 was conducted on Peanut in the district of Koppaka, West Godavari (Andhra Pradesh, India). The sowing was done during second week of 5 August with a variety K20. Phenological Status: Vegetative growth 24 DAS, Design &

Plot size: RBD & 20 Sq.mt. The weeds that have been controlled include Echinochloa colona, Brachiaria sp., Digera sp., and Trianthima sp.

EXAMPLE 7: Tank mix of Propaquizafop + Imazethapyr on Beans

TABLE 8

DAA means days after treatment.

The trial detailed in Table 8 was conducted on beans in the district of Jabalpur, Madhya Pradesh, INDIA. The sowing was done during second week of July with a variety JDL 79 of beans. Phenological Status: Vegetative growth 27 DAS, Design &

15 Plot size: RBD & 20 Sq.mt. The weeds that have been controlled include Echinochloa

colona, Panicum sp., Dinebra sp., Portulaca sp., Digera sp., and Trianthima sp. EXAMPLE 8: Tank mix of Propaquizafop + Imazethapyr on Field Peas

TABLE 9

DAA means days after treatment.

5 The trial detailed in Table 9 was conducted on field peas in the district of

Amaravati, Maharashtra, India. The sowing was done during third week of October with a variety of field peas. Phenological Status: Vegetative growth 28 DAS, Design & Plot size: RBD & 20 Sq.mt. The weeds that have been controlled include Eleusine indica, Dactyloctenium aegyptium, Corchprus sp., and Trianthema monogyna.

0

EXAMPLE 9: Tank mix of Propaquizafop + Imazethapyr on Cluster Beans

TABLE 10

Tank mix of Propaquizafop + Imazethapyr on Cluster Beans

% control % control

Colby Ratio o/e observed expected

Application

AI rate 15DAA 30DAA 15DAA 30DAA 15DAA 30DAA

(ml/Acre) Propaquizafop 200 65.64 72.43

Propaquizafop 250 65.13 71.96

Imazethapyr 300 62.56 68.69

Imazethapyr 350 58.97 66.36

Propaquizafop + Imazethapyr 200+300 93.85 98.13 87.14 91.37 1.08 1.07

Propaquizafop + Imazethapyr 200+350 94.36 98.13 85.90 90.72 1.10 1.08

Propaquizafop + Imazethapyr 250+300 90.77 94.39 86.95 91.22 1.04 1.03

Propaquizafop + Imazethapyr 250+350 90.77 94.86 85.69 90.57 1.06 1.05

DAA means days after treatment.

The trial detailed in Table 10 was conducted on cluster beans in the district of

Nagra, Hanumangarh dt, Rajsthan, India. The sowing was done during second week of July with a variety HG-365 of cluster beans. Phenological Status: Vegetative growth 27 DAS, Design & Plot size: RBD & 50 Sq.mt. The weeds that have been controlled

include Echinochloa colona, Panicum sp., Dinebra sp., Portulaca sp., Digera sp., and Trianthima sp.

DISCUSSION

All the above results show that the percentage of herbicidal control observed for the combination is greater than the expected percentage (Colby Ratio o/e). The data shows efficacy of total weeds (grassy+ broad leaf weed) on soybean, black gram, ground nut (peanut), red gram (pigeon peas), green gram, beans, field peas and cluster beans. In spite of what has been reported in the prior art it can be concluded that by combining imazethapyr and propaquizafop, a herbicidal mixture which has a broader spectrum of activity is obtained without crop damage.

All publications, patents and patent applications mentioned in this specification are herein incorporated in their entirety by reference into the specification, to the same extent as if each individual publication, patent or patent application was specifically and individually indicated to be incorporated herein by reference.

Features of the disclosed embodiments may be combined, rearranged, omitted, etc., within the scope of the present disclosure to produce additional embodiments. Furthermore, certain features may sometimes be used to advantage without a corresponding use of other features. It is thus apparent that there is provided in accordance with the present disclosure, mixtures, compositions and methods of a herbicidal mixture. Many alternatives, modifications, and variations are enabled by the present disclosure. While specific embodiments have been shown and described in detail to illustrate the application of the principles of the present subject matter, it will be understood that the subject matter may be embodied otherwise without departing from such principles. Accordingly, Applicants intend to embrace all such alternatives, modifications, equivalents, and variations that are within the spirit and scope of the present subject matter.

Claims

1. A herbicidal mixture comprising imazethapyr and propaquizafop, esters, salts and/or combination thereof.

2. The herbicidal mixture of claim 1, wherein the weight ratio of imazethapyr to propaquizafop is from 20: 1 to 1:20.

3. The herbicidal mixture of claim 1 or 2, wherein the weight ratio of imazethapyr to propaquizafop is from 5: 1 to 1:5.

4. The herbicidal mixture of any one of claims 1 to 3, wherein the compounds are applied jointly or in a succession.

5. The herbicidal mixture of any one of claims 1 to 4, wherein the application rate of the mixture is from 0.1 liter/ha to 10 liter/ha.

6. The herbicidal mixture of claim 5, wherein the application rate of the mixture is 1.25 liter/ha.

7. The herbicidal mixture of any one of claims 1 to 6 wherein the mixture is applied in an amount of 125 g/ha.

8. The herbicidal mixture of claim 7 wherein the amount of imazethapyr is 75 g/ha and the amount of propaquizafop is 50 g/ha.

9. A herbicidal composition comprising a mixture of imazethapyr and propaquizafop, esters, salts and/or combination thereof, and at least one agriculturally acceptable carrier.

10. The herbicidal composition of claim 9, further comprising at least one surfactant, solid diluent, liquid diluent, or a combination thereof.

11. The herbicidal composition of claim 9 or 10, wherein the composition is a microemulsion.

12. The herbicidal composition of any one of claims 9-11, wherein the weight ratio of imazethapyr to propaquizafop is from 20: 1 to 1:20.

13. The herbicidal composition of any one of claims 9-12, wherein the weight ratio of imazethapyr to propaquizafop is from 5: 1 to 1 :5.

14. The herbicidal composition of any one of claims 9-11, wherein imazethapyr is present in an amount ranging from about 1% -10% w/w based on the total weight of the emulsion concentrate.

15. The herbicidal composition of any one of claims 9-14 wherein propaquizafop is present in an amount ranging from about 1% -10% w/w based on the total weight of the emulsion concentrate.

16. The herbicidal composition of any one of claims 9-15, wherein said acceptable carrier is present in an amount ranging from about 40% -55% w/w based on the total weight of the emulsion concentrate.

17. The herbicidal composition of any one of claims 10-16, wherein said surfactants are present in an amount ranging from about 30% -50% w/w based on the total weight of the emulsion concentrate.

18. A method of controlling undesired vegetation comprising applying to the locus of the undesired vegetation a herbicidally effective amount of a mixture comprising imazethapyr, propaquizafop esters, salts and/or combination thereof.

19. The method of claim 18 wherein the crop is selected from the group consisting of soybeans, blackgram, peanuts, green gram, pigeon pea, beans, field peas and cluster beans.

20. The method of claim 18 or 19, wherein the mixture is applied in an amount of 1 to 500 g/ha.

21. The method of claim 20, wherein the mixture is applied in an amount of 125 g/ha.

22. The method of any one of claims 18-21 wherein the undesired vegetation is selected from the group consisting of Echinochloa Colona, Dinebra Arabica, Cynotis sp, Eleusine Indica, Cynodon Dactylon, Euphorbia Hirta, Amaranthus Viridis, Digeria Arvensis, Digera sp., Panicum sp., Phyllanthus sp, Commelina benghalensis L, Parthenium, Trianthema Portulacasturm, Cleome viscosa, Digera arvensis, Parthenium hysterophorus, Cynadon dactylone, Commelina bengalensis and Dinebra sp., Portulaca sp., Trianthima sp., Dactyloctenium aegyptium, Corchprus sp., Trianthema monogyna, Brachiaria sp.

23. A method of controlling undesired vegetation comprising applying to the locus of the undesired vegetation the composition of any one of claims 9-17.

24. A synergistic herbicidal mixture comprising imazethapyr and propaquizafop, esters, salts and/or combination thereof.

25. The synergistic herbicidal mixture of claim 24, wherein the weight ratio of imazethapyr to propaquizafop is from 20: 1 to 1:20.

26. The synergistic herbicidal mixture of claim 24 or 25, wherein the weight ratio of imazethapyr to propaquizafop is from 5: 1 to 1 :5.

27. The synergistic herbicidal mixture of any one of claims 24 to 26, wherein the compounds are applied jointly or in a succession.

28. The synergistic herbicidal mixture of any one of claims 24 to 27, wherein the application rate of the mixture is from 0.1 liter/ha to 10 liter/ha.

29. The synergistic herbicidal mixture of claim 28, wherein the application rate of the mixture is 1.25 liter/ha.

30. The synergistic herbicidal mixture of any one of claims 24 to 29 wherein the mixture is applied in an amount of 125 g/ha.

31. The synergistic herbicidal mixture of claim 30 wherein the amount of imazethapyr is 75 g/ha and the amount of propaquizafop is 50 g/ha.

32. A kit comprising the herbicidal mixture of claim 1 or claim 24.