WO2013067706A1

WO2013067706A1 - Herbicidal composition and method of using the same

Info

Publication number: WO2013067706A1
Application number: PCT/CN2011/082066
Authority: WO
Inventors: James Timothy Bristow
Original assignee: Rotam Agrochem International Co., Ltd
Priority date: 2011-11-11
Filing date: 2011-11-11
Publication date: 2013-05-16
Also published as: CN103957708B; CN103957708A

Abstract

The invention relates to an herbicidal composition for weed control, particularly in corn, wherein the herbicidal composition comprises mesotrione and at least one second herbicidal agent selected from the group consisting of nicosulfuron, dicamba, imazaquin, their salts and any combination thereof. The invention also relates to the methods using the compositions for controlling undesirable vegetation.

Description

Herbicidal composition and method of using the same

FIELD OF INVENTION

The invention relates to an herbicidal composition for weed control, particularly in maize (corn), wherein the herbicidal composition comprises mesotrione and at least one second herbicidal agent selected from the group consisting of nicosulfuron, dicamba, imazaquin, their salts and any combination thereof. The invention also relates to a method of using the composition for controlling undesirable vegetation in crops, particularly in maize.

BACKGROUND OF THE INVENTION

The control of undesired vegetation is extremely important in achieving high crop yield. Achievement of selective control of the growth of weeds especially in such useful crops as rice, soybean, sugar beet, corn (maize), potato, wheat, barley, tomato and plantation crops such as sugar cane, among others, is very desirable. Unchecked weed growth in such useful crops can cause significant reduction in productivity and thereby result in increased costs to consumers. Protection of crops from weeds and other vegetation that inhibits crops growth is a constantly recurring problem in agriculture. To help combat this problem, researchers in the field of synthetic chemistry have produced an extensive variety of chemicals and chemical formulations effective in controlling of such unwanted growth. Many types of herbicides have been disclosed in the literatures and a large number are in commercial use. In some cases, herbicidal active ingredients have been shown to be more effective in combination than when applied individually, and this is referred to as "synergism". "Synergism" is an interaction of two or more factors such that the effect when combined is greater than the predicted effect based on the response to each factor applied separately. Combinations of herbicides are typically used to broaden the spectrum of plant control or enhance the control of any given species through additive effect. Furthermore, certain rare combinations unexpectedly give a greater-than-additive or synergistic effect on weeds or a less-than-additive or safening effect on crops.

Patent application WO 2002/100173 discloses a composition comprising mesotrione and a second herbicide selected from triazines, thiazolinones, imidazolinones, dicamba, flumetsulam, trifloxysulfuron, tritosulfuron, triasulfuron, pyriftalid, prosulfocarb, pretilachlor, and cinosulfuron. The specification did not provide field test data and efficacy for controlling undesirable vegetation, particularly in crops.

CN1326455 describes a process of controlling triazine-tolerant weeds by the application of a combination of mesotrione and a triazine to the locus of said weeds.

CN 101953354 describes a compound herbicide composition which comprises mesotrione, dicamba and diflufenzopyr. The compound herbicide composition has higher weeding effect than a single preparation, a very high synergistic effect, reduces medicament dosage, decreases medicament cost of farmers, and delays the generation and development of resistance to the single preparation.

The present invention is based on the discovery that mesotrione and certain other herbicides display a synergistic effect when applied in combination. The combination of the present invention is new and has not been reported.

SUMMARY OF THE INVENTION

The present invention relates to a composition which provides improved herbicidal properties, for example, improved biological properties, and/or synergistic properties, especially for controlling undesirable vegetation, particularly in crops.

Accordingly, in a first aspect, the present invention provides an herbicidal composition comprising mesotrione and at least one second herbicidal agent selected from the group consisting of nicosulfuron, dicamba, imazaquin, their salts and any combination thereof. According to the present invention, the combinations of mesotrione and nicosulfuron, mesotrione and dicamba are excluded. Optionally, the herbicidal composition of the present invention may further comprise an agriculturally acceptable adjuvant and/or carrier. For example, the adjuvant and/or carrier may include one or more selected from the group consisting of surfactants, safeners, solvents, solid diluents and liquid diluents.

The present invention also includes embodiments in which one or further active ingredient is included, in addition to the components mesotrione and the second herbicidal agent. In another aspect, this invention provides a method of controlling growth of undesirable vegetation in crops, particularly maize (corn), comprising applying to the locus of the undesirable vegetation, an herbicidally effective amount of mesotrione and at least one second herbicidal agent selected from the group consisting of nicosulfuron, dicamba, imazaquin, their salts and any combination thereof. The combinations of mesotrione and nicosulfuron, mesotrione and dicamba are excluded. Preferably, the herbicidal composition of the present invention may further comprise an agriculturally acceptable adjuvant and/or carrier. For example, the adjuvant and/or carrier may include one or more selected from the group consisting of surfactants, safeners, solvents, solid diluents and liquid diluents.

Accordingly, in a third aspect, the present invention provides a method of protecting a plant against undesirable vegetation in crops by applying to the plant a product comprising a composition as hereinbefore defined.

DESCRIPTION OF THE PREFERRED EMBODIMENTS

It has been surprisingly found that the combination of mesotrione and at least one second herbicidal agent selected from the group consisting of nicosulfuron, dicamba, imazaquin, their salts and any combination thereof results in unexpectedly enhanced action in controlling undesirable vegetation in crops. In particular, the combination exhibits surprisingly high activity in controlling undesirable vegetation in maize.

In one aspect, the present invention provides an herbicidal composition comprising an herbicidally effective amount of mesotrione and at least one second herbicidal agent selected from the group consisting of nicosulfuron, dicamba, imazaquin, their salts and any combination thereof. The combinations of mesotrione and nicosulfuron, mesotrione and dicamba are excluded.

Mesotrione is commercially available in herbicidal compositions sold by Syngenta (e.g. CALLISTO® Herbicide). Although mesotrione is most conveniently obtained as a commercial product, it can be prepared as described in U.S. Patent 5,006,158, while its salts or metal chelates can be prepared as described in U.S. Patent 5,912,207. The formula of mesotrione is as below:

Nicosulfuron

(2-(4,6-dimethoxypyrimidin-2-ylcarbamoylsulfamoyl)-N,N-dimethyl-nico tinamide), disclosed in U.S. Patent 4,789,393, is a herbicide for selective post-emergence control of annual grass weeds, broad-leaved weeds and perennials in maize. The structure of nicosulfuron is as below:

Dicamba (3,6-dichloro-o-anisic acid), was first disclosed in U.S. Patent 3,013,054 as a selective systemic herbicide for control of annual and perennial broad-leaved weeds and brush species in cereals, maize, sorghum, sugar cane, asparagus, perennial seed grasses, turf, pastures, rangeland, and non-crop land. The structure is as below:

Imazaquin

((RiS')-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-quinoline-3-carb oxylic acid) is a selective systemic herbicide and uses for pre-planting, pre-emergence or early post-emergence control of broad- leaved weeds in soybean.

The herbicidal composition comprises an herbicidally effective amount of mesotrione and at least one second herbicidal agent. The term "herbicide" as used herein denotes a compound which controls or modifies growth of undesired plants. The term "herbicidally effective amount" indicates the quantity of such a compound or combination of such compounds which is capable of producing a controlling or modifying effect on the growth of undesired plants. Controlling or modifying effects include all deviation from natural development, for example: killing, retardation, leaf burn, albinism, dwarfing and the like. The term "plants" refer to all physical parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, stalks, foliage and fruits.

In some embodiments of the invention, the ratio of mesotrione and the second herbicidal agent in the herbicidal composition is from about 1 :50 to about 50: 1 by weight, preferably from about 1 :25 to about 25: 1 by weight, more preferably from about 1 : 10 to about 10: 1 by weight, for example from about 1 :5 to about 5: 1 by weight, from about 1 :4 to about 5:1 by weight, from about 1:3 to about 5:1 by weight, from about 1:2 to about 5:1 by weight, from about 1:1 to about 5:1 by weight, from about 1:5 to about 3:1 by weight, from about 1:4 to about 3:1 by weight, from about 1:3 to about 3:1 by weight, from about 1:2 to about 3:1 by weight, from about 1:1 to about 3:1 by weight, from about 1:5 to about 2:1 by weight, from about 1:4 to about 2:1 by weight, from about 1:3 to about 2:1 by weight, from about 1:2 to about 2:1 by weight, and from about 1:1 to about 2:1 by weight.

In one embodiment of the invention, the second herbicidal agent in the herbicidal composition can be the combination of nicosulfuron and dicamba, preferably with a ratio of about 10:1 to about 1: 10 by weight, more preferably about 5:1 to about 1:5, most preferably about 2:1 to about 1:2, for example 1:1.

In another embodiment of the invention, the second herbicidal agent in the herbicidal composition is the combination of nicosulfuron and imazaquin, preferably with a ratio of about 10:1 to about 1: 10 by weight, more preferably about 5:1 to about 1:5, most preferably about 2:1 to about 1:2, for example 1:1.

In a further embodiment of the invention, the second herbicidal agent in the herbicidal composition is the combination of dicamba and imazaquin, preferably with a ratio of about 10:1 to about 1: 10 by weight, more preferably about 5:1 to about 1:5, most preferably about 2:1 to about 1:2, for example 1:1.

In another embodiment of the invention, the second herbicidal agent in the herbicidal composition is the combination of nicosulfuron, dicamba, and imazaquin, preferably with a ratio of about 1 : 1 : 1 by weight.

In some other embodiments, the herbicidal composition further comprises an agriculturally acceptable adjuvant and/or carrier. For example, the adjuvant and/or carrier may include one or more selected from the group consisting of surfactants, safeners, solvents, solid diluents and liquid diluents. More preferably the adjuvant and/or carrier may include one or more selected from the group consisting of alkylpolyglycosides, alkylbetaines, alkyl(amidoalkyl)betaines, alkylamidopropyl dialkylamine, ammonium sulfate, and any combination thereof. More preferably the content of the adjuvant in the herbicidal composition is between about 0.01% and about 90% by weight, further more preferably between about 0.05% and about 50%, for example between about 0.1% and about 30%, between about 1% and about 20%. Additional safeners which are useful in this invention comprise 1,8-Naphthalic anhydride (Naphthalene- 1,8-dicarboxylic anhydride), Dichlormid (N,N-diallyl-2,2-dichloroacetamide), Cyometrinil ((Z)-cyanomethoxyimino(phenyl)acetonitrile), Oxabetrinil ((Z)- 1 ,3-dioxolan-2-ylmethoxyimino-(phenyl)acetonitrile), Flurazole (Benzyl-2-chloro-4-trifluoromethyl- 1 ,3-thiazole-5-carboxylate, Fenclorim (4,6-Dichloro-2-phenylpyrimidine), Benoxacor ((R_lS')-4-dichloroacetyl-3,4-dihydro-3-methyl-2H-l,4-benzoxazine), Fluxofenim

(4-Chloro-2,2,2-trifluoroacetophenone-0-l,3-dioxolan-2-ylmethyloxime)

In another aspect, the invention provides a method of controlling growth of undesirable vegetation in crops, particularly maize (corn), comprising applying to the locus of the undesirable vegetation, a herbicidally effective amount of the herbicidal composition according to the invention.

In a further aspect, the invention provides a method of controlling growth of undesirable vegetation in crops, particularly maize (corn), comprising applying to the locus of the undesirable vegetation, an herbicidally effective amount of a mesotrione and at least one second herbicidal agent selected from the group consisting of nicosulfuron, dicamba, imazaquin, their salts and any combination thereof.

In some embodiments of this invention, the combined amount of mesotrione and the second herbicidal agent applied to the locus of the undesirable vegetation is between about 0.001 kg/ha and about 5 kg/ha, preferably between about 0.01 kg/ha and about 3 kg/ha, more preferably between about 0.02 kg/ha and about 2 kg/ha, for example between about 0.02 kg/ha and about 1 kg/ha, between about 0.02 kg/ha and about 0.5 kg/ha, between about 0.02 kg/ha and about 0.2 kg/ha, between about 0.02 kg/ha and about 0.1 kg/ha, between about 0.02 kg/ha and about 0.08 kg/ha, between about 0.04 kg/ha and about 2 kg/ha, for example between about 0.04 kg/ha and about 1 kg/ha, between about 0.04 kg/ha and about 0.5 kg/ha, between about 0.04 kg/ha and about 0.2 kg/ha, between about 0.04 kg/ha and about 0.1 kg/ha, between about 0.04 kg/ha and about 0.08 kg/ha, between about 0.2 kg/ha and about 2 kg/ha, between about 0.2 kg/ha and about 1.5 kg/ha, between about 0.2 kg/ha and about 1 kg/ha, between about 0.2 kg/ha and about 0.7 kg/ha, between about 0.4 kg/ha and about 2 kg/ha, between about 0.4 kg/ha and about 1.5 kg/ha, between about 0.4 kg/ha and about 1 kg/ha, and between about 0.4 kg/ha and about 0.7 kg/ha.

In an embodiment, the second herbicidal agent applied to the locus of the undesirable vegetation is the combination of nicosulfuron and dicamba, preferably with a ratio of about 10: 1 to about 1 : 10 by weight, more preferably about 5: 1 to about 1 :5, most preferably about 2: 1 to about 1 :2, for example 1 : 1. In another embodiment, the second herbicidal agent applied to the locus of the undesirable vegetation is the combination of nicosulfuron and imazaquin, preferably with a ratio of about 10: 1 to about 1 : 10 by weight, more preferably about 5: 1 to about 1 :5, most preferably about 2: 1 to about 1 :2, for example 1 : 1. In another embodiment, the second herbicidal agent applied to the locus of the undesirable vegetation is the combination of dicamba and imazaquin, preferably with a ratio of about 10: 1 to about 1 : 10 by weight, more preferably about 5: 1 to about 1 :5, most preferably about 2: 1 to about 1 :2, for example 1 : 1. In another embodiment, the second herbicidal agent applied to the locus of the undesirable vegetation is the combination of nicosulfuron, dicamba, and imazaquin, preferably with a ratio of about 1 : 1 : 1 by weight.

In some other embodiments, mesotrione and the second herbicidal agent are applied at pre-emergence or post-emergence.

In some other embodiments, mesotrione and the second herbicidal agent are applied together with an adjuvant and/or carrier. Preferably, the adjuvant and/or carrier may include one or more surfactants and/or safeners. More preferably, the adjuvant may include one or more selected from the group consisting of alkylpolyglycosides, alkylbetaines, alkyl(amidoalkyl)betaines, alkylamidopropyl dialkylamine, ammonium sulfate, and any combination thereof. More preferably, the content of the adjuvant is between about 0.01% and about 50% by weight, further more preferably between about 0.05% and about 30%, for example between about 0.1 % and about 10%.

In another aspect, the invention also provides use of an herbicidal composition comprising an herbicidally effective amount of mesotrione and at least one second herbicidal agent selected from nicosulfuron, dicamba, imazaquin, their salts and any combination thereof in controlling growth of undesirable vegetation in crops, particularly maize.

For example, the invention may be used to control dicotyledonous weeds such as Abutilon spp., Ambrosia spp., Amaranthus spp., Chenopodium spp., Erysimum spp., Euphorbia spp., Fallopia spp., Galium spp., Hydrocotyle spp., Ipomoea spp., Lamium spp., Medicago spp., Oxalis spp., Plantago spp., Polygonum spp., Richardia spp., Sida spp., Sinapis spp., Solarium spp., Stellaria spp., Taraxacum spp., Trifolium spp., Veronica spp., Viola spp. and Xanthium spp.

The invention may also be used to control monocotyledonous weeds such as Agrostis spp., Alopecurus spp., Apera spp., Avena spp., Brachiaria spp., Bromus spp., Digitaria spp., Echinochloa spp., Eleusine spp., Eriochloa spp., Leptochloa spp., Lolium spp., Ottochloa spp., Panicum spp., Paspalum spp., Phalaris spp., Poa spp., Rottboellia spp., Setaria spp., Sorghum spp., both intrinsically sensitive as well as resistant (e.g. ACCase and/or ALS resistant) biotypes of any of these grass weeds, as well as broadleaf monocotyledonous weeds such as Commelina spp., Monochoria spp., Sagittaria spp. and sedges such as Cyperus spp. and Scirpus spp.

As used herein, the term "mesotrione" comprises mesotrione in the form of acid, salts, and metal chelates. Salts of mesotrione include those formed with organic bases (e.g. pyridine, ammonia, or triethylamine) or inorganic bases (e.g. hydrides, hydroxides, or carbonates of sodium, potassium, lithium, calcium, magnesium or barium). Besides containing metal cations such as alkali metal (e.g. sodium, potassium, lithium) and alkaline earth metal (e.g. calcium, magnesium, barium), salts of mesotrione can also include sulfonium, sulfoxonium and quaternary ammonium cations. Salts of mesotrione can be prepared in a number of ways known in the art for preparing salts of acidic organic compounds. For example, metal salts can be made by mixing mesotrione in its acid form with a solution of an alkali or alkaline earth metal salt having a sufficiently basic anion (e.g. hydroxide, alkoxide, carbonate or hydride). Quaternary ammonium salts can be made by similar techniques. Salts of mesotrione can also be prepared by exchange of one cation for another. Cationic exchange can be effected by direct contact on an aqueous solution of a salt of mesotrione (e.g. alkali or quaternary ammonium salt) with a solution containing the cation to be exchanged. The method is most effective when the desired salt containing the exchanged cation is insoluble in water and can be separated by filtration. Exchange may also be effected by passing an aqueous solution of a salt of a compound of mesotrione (e.g. an alkali metal or quaternary ammonium salt) through a column packed with a cation-exchange resin containing the cation to be exchanged for that of the original salt, and the desired product is eluted from the column. This method is particularly useful when the desired salt is water soluble (e.g. potassium, sodium or calcium salt) (examples see patent applications US 2009/0209426 and WO 2007133522). Mesotrione can also be used in the form of metal chelates, such as a copper chelate. Most preferably, the mesotrione is in the form of a copper chelate. Metal chelates of mesotrione and their preparation are known and described in U.S. Patent 5,912,207. As used herein, the term "locus" is intended to include soil, seeds, and seedlings as well as established vegetation.

The benefits of the present invention are seen most when the pesticidal composition is applied to kill weeds in growing crops of useful plants: such as maize (corn) including field corn, pop corn and sweet corn; cotton, wheat, rice, oats, potato sugar beet, plantation crops (such as bananas, fruit trees, rubber trees, tree nurseries), vines, asparagus, bushberries (such as blueberries), caneberries, cranberries, flax, grain sorghum, okra, peppermint, rhubarb, spearmint and sugar cane.

As used herein, the term "crops" are to be understood to include those crops that have been made tolerant to pests and pesticides, including herbicides or classes of herbicides (and, suitably, the herbicides of the present invention), as a result of conventional methods of breeding or genetic engineering. Tolerance to herbicides means a reduced susceptibility to damage caused by a particular herbicide compared to conventional crop breeds. Crops can be modified or bred so as to be tolerant, for example, to HPPD inhibitors such as mesotrione, EPSPS inhibitors such as glyphosate or to glufosinate. It is noted that corn is naturally tolerant to mesotrione.

As used herein, the terms "comprises," "comprising," "includes," "including," "has," "having" or any other variation thereof, are intended to cover a non-exclusive inclusion. For example, a composition, process, method, article, or apparatus that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such composition, process, method, article, or apparatus. Further, unless expressly stated to the contrary, "or" refers to an inclusive or and not to an exclusive or. For example, a condition A or B is satisfied by any one of the following: A is true (or present) and B is false (or not present), A is false (or not present) and B is true (or present), and both A and B are true (or present). Also, the indefinite articles "a" and "an" preceding an element or component of the invention are intended to be nonrestrictive regarding the number of instances (i.e. occurrences) of the element or component. Therefore "a" or "an" should be read to include one or at least one, and the singular word form of the element or component also includes the plural unless the number is obviously meant to be singular. And, the content composition is given by weight, unless the context specifies otherwise.

Each of the foregoing patents, patent applications and references that are recited in this application are herein incorporated in their entirety by reference. The recitation of the references is not intended to be an admission that any of the references is a prior art reference. Having described the presently preferred embodiments, and in accordance with the present invention, it is believed that other modifications, variations and changes will be suggested to those skilled in the art in view of the teachings set forth herein. It is, therefore, to be understood that all such variations, modifications, and changes are believed to fall within the scope of the present invention as defined by the appended claims.

Formulation Examples

Example 1 Water-soluble concentrate (SL)

Mesotrione 25 g

Imazaquin 5 g

TWEEN 80 (sorbitan monooleate ethoxylate) 10 g Water balance to 100 g

Example 2 Emulsifiable concentrate (EC)

Mesotrione 50 g

Imazaquin 2.5 g

TWEEN 80 (sorbitan monooleate ethoxylate) 10 g 70B (calcium dodecylphenylsulfonate) 4 g

Solvesso 200 10 g

N-methyl pyrrolidone balance to 100 g

Example 3 Water- dispersible powder (WP)

Mesotrione 80 g

Imazaquin 1.6 g

Dispersogen 1494 (sodium salt from cresol-formaldehyde 5 g condensation)

Kaolin balance to 100 g Example 4 Water- dispersible granule (WG)

Mesotrione 60 g

Imazaquin 6 g

Poly vinyl alcohol 2 g

Dispersogen 1494 (sodium salt from cresol-formaldehyde 5 g condensation)

Kaolin balance to 100 g Example 5 Water-soluble concentrate (SL)

Mesotrione 2 g

Imazaquin 2 g

TWEEN 80 (sorbitan monooleate ethoxylate) 5 g Water balance to 100 g Example 6 Water-soluble concentrate (SL)

Mesotrione 1 g

Imazaquin 50 g

TWEEN 80 (sorbitan monooleate ethoxylate) 10 g

Water balance to 100 g

Example 7 Water- dispersible granule (WG)

Mesotrione 1 g

Imazaquin 20 g

Poly vinyl alcohol 2 g

Dispersogen 1494 (sodium salt from cresol-formaldehyde 5 g condensation)

Kaolin balance to 100 g Example 8 Water- dispersible powder (WP)

Mesotrione 5 g

Imazaquin 25 g

Dispersogen 4387 (anionic polymeric ester) 5 g

Kaolin balance to 100 g

Example 9 Water-soluble concentrate (SL)

Mesotrione 5g Imazaquin 10 g

TWEEN 80 (sorbitan monooleate ethoxylate) 10 g Water Balance to 100 g

Example 10 Suspoemulsion (SE)

Mesotrione l g

Imazaquin 10g

Solvesso 200 20 g

TWEEN 80 (sorbitan monooleate ethoxylate) 10 g Propylene glycol 5g Xanthan gum 2 g Water balance to 100 g

Example 11 Oil-in-water emulsion (EW)

Mesotrione 3 g

Imazaquin 9 g

Solvesso 200 20 g

EL360 (ethoxylated soybean oil) 5 g 70B (calcium dodecylphenylsulfonate) 3 g Water Balance to 100 g

Example 12 Water- dispersible powder (WP)

Mesotrione Nicosulfuron 2 g

Dicamba 20 g

Dispersogen 4387 (anionic polymeric ester) 4 g

Kaolin Balance to 100 g

Example 13 Water -dispersible granule (WG)

Mesotrione 10 g

Nicosulfuron 20 g

Dicamba 2 g

Poly vinyl alcohol 2 g

Dispersogen 1494 (sodium salt from cresol-formaldehyde 2 g condensation)

Silicon Balance to 100 g Example 14 Oil-in-water emulsion (EW)

Mesotrione 10 g

Nicosulfuron 5 g

Dicamba 1 g

Solvesso 200 20 g

EL360 (ethoxylated soybean oil) 5 g

70B (calcium dodecylphenylsulfonate) 3 g

Water Balance to 100 g

Example 15 Suspoemulsion (SE) Mesotrione 10 g Nicosulfuron i g Dicamba

Solvesso 200 20 g

TWEEN 80 (sorbitan monooleate ethoxylate) 5 g Propylene glycol 5 g Xanthan gum 2 g Water Balance to 100 g

Example 16 Emulsion concentrate (EC)

Mesotrione 10 g

Nicosulfuron 20 g

Dicamba 10 g

N-methyl pyrrolidione 20 g

EL360 (ethoxylated soybean oil) 8 g

70B (calcium dodecylphenylsulfonate) 4 g

Solvesso 200 Balance to 100 g

Example 17 Emulsion concentrate (EC)

Mesotrione 10 g

Nicosulfuron 3 g

Imazaquin 6 g

N-methyl pyrrolidione 20 g EL360 (ethoxylated soybean oil) 5 g 70B (calcium dodecylphenylsulfonate) 3 g Solvesso 200 Balance to 100 g

Example 18 Emulsion concentrate (EC)

Mesotrione 20 g

Nicosulfuron 5 g

Imazaquin 1

EL360 (ethoxylated soybean oil) σ o

70B (calcium dodecylphenylsulfonate) 3 g Solvesso 200 Balance to 100 g

Example 19 Water-dispersible granule (WG)

Mesotrione 20 g

Nicosulfuron 20 g

Imazaquin 2 g

Poly vinyl alcohol 2 g

Dispersogen 1494 (sodium salt from cresol-formaldehyde 4 g condensation)

Kaolin Balance to 100 g

Example 20 Water-dispersible powder (WP)

Mesotrione 20 g Nicosulfuron 2 g

Imazaquin 20 g

Dispersogen 1494 (sodium salt from cresol-formaldehyde 4 g condensation)

Silicon Balance to 100 g Example 21 Emulsion concentrate (EC)

Mesotrione 10 g

Nicosulfuron 3 g

Imazaquin 15 g

N-methyl pyrrolidine 20 g

EL360 (ethoxylated soybean oil) 5 g

70B (calcium dodecylphenylsulfonate) 3 g

Solvesso 200 Balance to 100 g

Example 22 Water- dispersible powder (WP)

Mesotrione 20 g

Nicosulfuron 10 g

Imazaquin 5 g

Dispersogen 1494 (sodium salt from cresol-formaldehyde 4 g condensation)

Silicon Balance to 100 g

Example 23 Emulsion concentrate (EC) Mesotrione 10 g

Dicamba 3 g

Imazaquin 6 g

N-methyl pyrrolidione 20 g

EL360 (ethoxylated soybean oil) 5 g

70B (calcium dodecylphenylsulfonate) 3 g Solvesso 200 Balance to 100 g

Example 24 Emulsion concentrate (EC)

Mesotrione 20 g

Dicamba 5 g

Imazaquin 1 g

EL360 (ethoxylated soybean oil) 5 g

70B (calcium dodecylphenylsulfonate) 3 g Solvesso 200 Balance to 100 g

Example 25 Water- dispersible granule (WG)

Mesotrione 20 g

Dicamba 20 g

Imazaquin 2 g

Poly vinyl alcohol 2 g

Dispersogen 1494 (sodium salt from cresol-formaldehyde 4 g condensation) Kaolin Balance to 100 g

Example 26 Water- dispersible powder (WP)

Mesotrione 20 g

Dicamba 2 g

Imazaquin 20 g

Dispersogen 1494 (sodium salt from cresol-formaldehyde 4 g condensation)

Silicon Balance to 100 g

Example 27 Emulsion concentrate (EC)

Mesotrione 10 g

Dicamba 3 g

Imazaquin 15 g

N-methyl pyrrolidione 20 g EL360 (ethoxylated soybean oil) 5 g 70B (calcium dodecylphenylsulfonate) σ o Solvesso 200 Balance to 100 g

Example 28 Water- dispersible powder (WP)

Mesotrione 20 g

Dicamba 10 g

Imazaquin σ o Dispersogen 1494 (sodium salt from cresol-formaldehyde 4 g condensation)

Silicon Balance to 100 g

Example 29 Water- dispersible granule (WG)

Mesotrione 20 g

Nicosulfuron 10 g

Dicamba 10 g

Imazaquin 10 g

Poly vinyl alcohol 2 g

Dispersogen 1494 (sodium salt from cresol-formaldehyde 4 g condensation)

Kaolin Balance to 100 g

Biological Examples

Field evaluation 1

The samples according to Examples 1 to 29 were applied (at the rates listed in Table 1 below) at pre-emergence to aluminum flats

(measuring 16 x 23 x 7 cm deep) containing loam soil in which the following species had been sown: Abutilon, Ambrosia, Amaranthus,

Chenopodium, Agrostis, Alopecurus, Apera, Avena and corn. The soil was fortified with fertilizer and treated with a fungicide, Captan 80W, prior to seeding. All of the herbicides were applied at pre-emergence with the carrier volume of 234 L/ha.

After application of the compositions according to the present invention, the flats were placed in a greenhouse. Injury to plants was rated at 8 and 27 days after treatment ("DAT"). Injury was evaluated as percent control, with percent control being the total injury to the plants due to all factors including inhibited emergence, stunting, malformation, albinism, chlorosis, and other types of plant injury. The control ratings range from 0 to 100 percent, where 0% represents no effect with growth b_l A_ituon

compared with the untreated control and where 100% represents complete kill.

b A_imro_sa

8 DAT observation Table 1

h A_tmaranu_s

Rate h^d Cⁱenopoum (g AI/ha) A^itgro^ss

31 95 98 100 100 98 95 97 100 0 l Aopecuru^s

Example 1 63 98 98 100 100 98 97 100 100 0

Apera

125 100 100 100 100 100 100 100 100 0

31 95 94 96 92 96 97 98 9 Avena8 0

Example 2 63 98 95 97 98 98 98 100 100 C 0o^rn

125 100 100 100 100 100 100 100 100 0

31 92 93 94 96 97 95 95 96 0

Example 3 63 95 95 96 96 97 98 98 98 0

125 98 98 98 98 100 100 100 100 0

31 96 96 96 96 97 96 96 96 0

Example 4 63 98 98 98 98 98 98 98 98 0

125 100 100 100 100 100 100 100 100 0 31 94 94 95 92 95 94 96 95 0

Example 5 63 96 98 98 98 96 98 98 97 0

125 98 98 100 100 100 100 100 100 0

31 92 93 94 95 95 96 96 96 0

Example 6 63 97 97 96 97 97 97 97 98 0

125 98 98 98 100 100 100 100 100 0

31 91 90 96 94 93 92 90 91 0

Example 7 63 93 93 96 97 95 96 95 97 0

125 98 98 98 98 97 96 95 94 0

31 94 94 90 91 93 92 90 94 0

Example 8 63 95 95 96 95 94 93 93 94 0

125 98 96 97 98 96 97 98 98 0

31 91 91 92 91 92 93 93 93 0

Example 9 63 93 93 94 93 95 96 94 94 0

125 95 95 95 95 95 95 95 95 0

31 91 91 91 91 92 93 93 94 0

Example

63 93 95 94 96 92 94 95 95 0 10

125 98 98 97 98 98 96 98 98 0

31 90 90 91 92 93 93 94 94 0

Example

63 95 95 95 95 95 95 96 95 0 11

125 98 98 98 100 100 100 100 100 0 31 90 91 92 93 93 91 94 95

Example

63 93 90 95 95 96 94 96 96 12

125 98 97 98 96 100 98 98 98

31 91 91 92 91 92 93 93 93

Example

63 93 90 95 95 96 94 96 96 13

125 98 98 97 98 98 96 98 98

31 91 91 92 91 92 93 93 93

Example

63 93 90 95 95 96 94 96 96 14

125 98 98 97 98 98 96 98 98

31 94 94 95 92 95 94 96 95

Example

63 93 95 94 96 92 94 95 95 15

125 98 98 98 100 100 100 100 100

31 90 90 91 92 93 93 94 94

Example

63 93 93 94 93 95 96 94 94 16

125 98 96 97 98 96 97 98 98

31 95 94 96 92 96 97 98 98

Example

63 98 95 97 98 98 98 100 100 17

125 100 100 100 100 100 100 100 100

31 95 94 96 92 96 97 98 98

Example 18 63 98 95 97 98 98 98 100 100

125 98 98 97 98 98 96 98 98 31 95 94 96 92 96 97 98 98 0

Example

63 93 90 95 95 96 94 96 96 0 19

125 98 98 98 100 100 100 100 100 0

31 94 94 95 92 95 94 96 95 0

Example

63 93 90 95 95 96 94 96 96 0 20

125 98 98 98 100 100 100 100 100 0

31 95 94 96 92 96 97 98 98 0

Example

63 93 90 95 95 96 94 96 96 0 21

125 98 96 97 98 96 97 98 98 0

31 92 93 94 95 95 96 96 96 0

Example

63 93 93 94 93 95 96 94 94 0 22

125 98 98 98 100 100 100 100 100 0

31 92 90 95 90 93 95 97 96 0

Example23 63 93 94 96 95 96 94 96 96 0

125 98 98 98 100 100 100 100 100 0

Example 31 92 93 91 96 92 91 94 93 0 24 63 93 95 94 96 92 94 95 95 0

125 100 100 100 100 100 100 100 100 0

31 94 94 90 91 93 92 90 94 0

Example

63 97 97 96 97 97 97 97 98 0 25

125 98 96 97 98 96 97 98 98 0 31 94 94 95 92 95 94 96 95 0

Example

63 96 98 98 98 96 98 98 97 0 26

125 98 98 100 100 100 100 100 100 0

31 31 90 90 91 92 93 93 94 94

Example

63 63 95 95 95 95 95 95 96 95 27

125 125 98 98 98 100 100 100 100 100

31 91 90 96 94 93 92 90 91 0

Example

63 93 93 96 97 95 96 95 97 0 28

125 98 98 98 98 97 96 95 94 0

31 91 91 92 91 92 93 93 93 0

Example

63 93 93 94 93 95 96 94 94 0 29

125 95 95 95 95 95 95 95 95 0

100 g/L 31 65 70 63 67 73 68 69 68 0 mesotrione 63 70 75 74 79 71 70 70 70 0 SC 125 80 84 85 84 83 82 84 85 0

40 g/L 31 60 68 60 65 64 65 65 64 0 Nicosulfur 63 63 63 64 65 63 62 64 63 0 on OD (Ishihara

125 70 72 74 73 70 70 70 70 0 Sangyo Kaisha) 480 g/L 31 54 52 51 54 50 53 52 50 0 Dicamba 63 67 65 64 64 67 64 63 60 0

SL

125 76 77 79 75 74 70 76 75 0 (Syngenta)

10 % 31 45 46 42 41 43 46 45 45 0 Imazaquin 63 65 63 63 62 60 60 63 62 0

SL (Hangzhou 125 76 77 78 75 73 74 75 76 0 Yilong)

Untreated - 0 0 0 0 0 0 0 0 0

The above results indicated unexpected corn selectivity of the premix and high efficacy to dicotyledonous and monocotyledonous weeds.

63 94 92 92 93 94 93 95 95 0

125 98 98 98 98 98 98 98 98 0

31 86 87 89 90 92 90 90 92 0

Example 3 63 95 95 96 96 97 98 98 98 0

125 95 95 95 95 95 96 96 96 0

31 87 88 87 88 84 87 88 89 0

Example 4 63 90 94 94 94 95 95 97 94 0

125 98 98 100 100 100 98 98 98 0

31 90 90 90 90 90 90 90 90 0

Example 5 63 95 95 95 95 95 95 95 94 0

125 95 95 100 100 100 100 98 98 0

31 84 86 84 84 86 88 88 88 0

Example 6 63 89 90 90 93 91 91 90 93 0

125 98 98 98 100 100 100 100 100 0

31 85 88 88 90 88 86 86 88 0

Example 7 63 90 90 90 90 90 95 94 93 0

125 98 98 98 98 97 96 95 94 0

31 87 88 88 89 88 87 88 89 0

Example 8 63 93 94 93 92 93 92 90 90 0

125 95 94 93 93 93 93 98 98 0

Example 9 31 89 88 85 84 86 83 84 93 0 63 90 90 94 92 91 93 90 90 0

125 95 94 95 95 95 96 95 95 0

31 85 88 88 90 88 86 86 88 0

Example

63 93 95 94 90 92 94 95 90 0

10

125 98 96 97 98 98 96 96 98 0

31 90 90 91 92 93 90 90 90 0

Example

63 93 95 95 93 95 92 91 93 0

11

125 98 98 98 100 100 100 100 100 0

31 90 91 92 93 88 91 89 87 0

Example

63 93 90 91 93 90 94 92 91 0

12

125 95 95 95 95 90 93 92 90 0

31 90 90 90 90 90 90 90 90 0

Example

63 93 90 92 92 96 94 91 91 0

13

125 93 93 96 98 98 96 98 98 0

31 91 91 92 91 92 90 93 90 0

Example

63 93 90 95 95 93 94 95 95 0

14

125 98 98 97 98 98 96 98 98 0

31 90 90 90 92 91 92 94 90 0

Example

63 93 95 94 94 92 94 95 95 0

15

125 98 98 98 100 100 100 100 100 0

Example 31 90 90 91 92 93 90 89 89 0 16 63 93 93 94 93 95 96 94 94 0

125 96 95 93 92 93 92 93 94 0

31 88 85 84 86 85 85 87 86 0

Example

63 90 90 90 90 90 90 90 90 0 17

125 98 96 95 95 94 95 94 95 0

31 90 91 92 90 91 90 91 92 0

Example 18 63 94 91 90 93 93 92 94 94 0

125 98 98 97 98 98 96 98 98 0

31 89 88 89 90 92 93 91 92 0

Example

63 94 93 96 97 95 95 95 95 0 19

125 91 90 90 90 94 95 93 92 0

31 90 90 90 89 88 89 88 85 0

Example

63 93 90 95 86 88 94 87 87 0 20

125 99 97 97 100 100 98 100 98 0

31 90 83 84 84 88 90 86 85 0

Example

63 90 90 90 91 90 93 90 90 0 21

125 95 95 95 94 95 93 94 95 0

31 90 90 90 90 93 93 93 92 0

Example22 63 92 91 93 89 90 89 88 85 0

125 93 90 94 89 89 94 87 87 0

Example 31 85 89 80 84 85 85 87 88 0 23 63 90 90 94 93 95 96 94 94 0

125 92 93 92 92 92 93 93 92 0

Example 31 92 93 91 96 92 91 94 93 0 24 63 93 95 94 96 92 94 95 95 0

125 94 94 94 93 93 92 93 100 0

31 87 88 85 87 87 88 87 88 0

Example

63 90 90 90 90 90 90 93 93 0 25

125 93 93 91 93 94 92 93 93 0

31 90 90 91 91 90 91 90 91 0

Example

63 90 90 92 92 91 93 92 90 0 26

125 94 93 93 92 91 92 93 93 0

31 31 84 83 84 87 90 88 89 0

Example

63 63 90 90 90 90 91 91 92 0 27

125 125 92 93 93 94 92 94 95 0

31 89 90 89 90 90 90 90 90 0

Example

63 91 92 92 93 93 94 92 93 0 28

125 98 98 98 98 97 96 95 94 0

31 90 90 92 91 90 90 90 90 0

Example

63 93 92 92 93 92 93 94 92 0 29

125 94 94 93 94 94 93 94 94 0

100 g/L 31 31 43 23 43 45 45 45 47 0 mesotrione 63 54 54 55 53 544 55 58 57 0 SC 125 74 76 75 76 73 74 70 70 0

40 g/L 31 34 35 35 36 37 38 34 35 0 Nicosulfur 63 35 36 35 45 47 45 45 48 0 on OD (Ishihara

125 65 65 67 64 63 65 65 63 0 Sangyo Kaisha)

480 g/L 31 23 26 34 35 43 42 32 45 0 Dicamba 63 45 54 43 45 54 46 47 48 0

SL

125 88 87 76 75 74 70 76 75 0 (Syngenta)

10 % 31 12 15 15 16 15 23 23 25 0 Imazaquin 63 43 45 46 45 54 46 47 46 0

SL (Hangzhou 125 54 56 46 56 56 55 54 65 0 Yilong)

Untreated - 0 0 0 0 0 0 0 0 0

The above results indicated unexpected corn selectivity of the premix, high efficacy to dicotyledonous and monocotyledonous weeds and long pesticide duration.

Field evaluation 2 Seeds of plant species Abutilon, Ambrosia, Amaranthus, Chenopodium, Agrostis, Alopecurus, Apera, Avena and corn were sown in aluminum flats containing soil comprising of 2 parts sandy loam and 1 part peat. Twelve days after seeding, the samples according to Examples 1 to 29 were applied (at the rates listed in Table 3) at post-emergence. The flats were placed in a greenhouse and injury to plants evaluated at 17 days after treatment. 7 DAT observation Table 3

31 90 94 90 92 95 90 94 92 0

Example 5 63 90 98 95 92 92 93 94 95 0

125 95 92 100 100 100 100 100 100 0

31 92 93 94 95 95 94 94 96 0

Example 6 63 97 97 96 97 98 96 97 98 0

125 98 98 96 100 100 100 100 100 0

31 91 90 94 91 93 92 90 91 0

Example 7 63 93 93 95 97 95 96 95 97 0

125 98 98 98 98 98 96 98 94 0

31 89 90 90 91 93 92 90 94 0

Example 8 63 95 95 96 96 94 93 95 94 0

125 98 96 100 98 96 97 100 98 0

31 85 84 92 91 92 90 93 93 0

Example 9 63 93 93 94 93 95 95 94 94 0

125 95 95 95 94 95 95 95 95 0

31 90 89 91 88 92 93 90 94 0

Example

63 93 95 90 96 92 90 95 95 0 10

125 98 100 97 98 100 96 98 98 0

31 90 90 91 92 93 93 97 94 0

Example

63 95 95 95 96 95 96 96 95 0 11

125 98 98 98 100 98 100 98 100 0 31 90 83 92 93 86 91 94 89

Example

63 93 90 95 95 90 94 96 96 12

125 98 97 98 96 95 98 96 97

31 85 91 86 91 92 85 88 90

Example

63 93 90 95 95 95 94 96 95 13

125 94 94 96 98 95 96 94 98

31 91 91 92 91 92 93 93 93

Example

63 93 90 95 95 95 94 96 96 14

125 98 98 97 98 95 96 95 95

31 90 90 91 92 92 93 95 95

Example

63 93 93 94 95 92 94 95 95 15

125 98 98 98 97 98 97 94 94

31 83 82 88 84 83 86 85 87

Example

63 90 90 92 90 95 93 92 90 16

125 91 93 90 94 96 97 98 98

31 90 90 90 92 90 90 90 90

Example

63 94 95 95 95 98 96 100 100 17

125 100 100 100 100 100 100 100 100

31 87 89 88 89 90 95 94 92

Example 18 63 91 90 94 92 90 93 95 92

125 94 98 97 98 98 96 98 98 31 90 90 94 90 93 92 92 91

Example

63 93 95 95 95 96 94 92 93 19

125 98 98 98 100 100 100 100 100

31 83 85 86 88 86 87 86 87

Example

63 93 90 95 95 96 94 96 96 20

125 98 98 98 100 100 100 100 100

31 90 89 92 91 90 91 90 91

Example

63 93 91 94 94 95 96 93 95 21

125 94 93 96 95 98 98 98 100

31 80 84 85 88 87 87 86 88

63 93 90 95 95 94 94 93 94

Example22

125 95 94 93 100 100 100 100 100

31 91 94 91 87 83 87 85 85

Example

63 90 92 93 95 93 93 92 93 23

125 95 96 98 96 100 98 95 98

31 90 91 90 92 87 90 87 92

Example

63 90 91 93 92 92 93 91 93 24

125 96 96 97 98 98 98 96 96

31 92 93 94 95 95 94 94 96

Example

63 97 97 96 97 98 96 97 98 25

125 98 98 96 100 100 100 100 100 31 91 90 94 91 93 92 90 91 0

Example

63 93 93 95 97 95 96 95 97 0 26

125 98 98 98 98 98 96 98 94 0

31 89 90 90 91 93 92 90 94 0

Example

63 91 90 90 90 90 90 90 90 0 27

125 96 96 97 98 97 96 96 97 0

31 84 85 86 84 85 83 84 84 0

Example

63 90 90 90 90 90 90 90 90 0 28

125 95 96 97 98 97 96 96 97 0

31 80 83 83 84 85 83 84 84 0

Example

63 91 90 91 90 90 90 90 90 0 29

125 95 96 97 98 97 96 96 97 0 lOOg/L 23 65 44 56 65 70 65 65 61 0 Mesotrione 63 60 65 64 70 61 60 60 60 0 SC 125 81 84 82 85 83 82 84 85 0

40g/L 31 34 35 43 32 44 46 48 47 0 Nicosulfur 63 62 61 60 62 60 61 60 62 0 on OD (Ishihara

125 65 66 70 73 70 70 70 70 0 Sangyo Kaisha) 480g/L 23 45 43 54 44 46 45 43 46 0 Dicamba 63 43 32 45 56 63 61 64 54 0

SL

125 86 56 45 67 65 53 54 56 0 (Syngenta)

10% 31 45 46 42 41 43 46 45 45 0 Imazaquin 63 65 63 63 62 60 60 63 62 0 SL

( Hangzhou 125 79 77 76 75 73 74 77 71 0 Yilong)

Untreated - 0 0 0 0 0 0 0 0 0

Claims

1. Herbicidal composition comprising an herbicidally effective amount of mesotrione and at least one second herbicidal agent selected from the group consisting of nicosulfuron, dicamba, imazaquin, their salts and any combination thereof. The combinations of mesotrione and nicosulfuron, mesotrione and dicamba are excluded.

2. The herbicidal composition according to claim 1, wherein the ratio of mesotrione and the second herbicidal agent is from about 1 :50 to about 50: 1 by weight, preferably from about 1 :20 to about 20: 1, more preferably from about 1 : 10 to about 10: 1.

3. The herbicidal composition according to any one of claims 1 to 2, wherein the second herbicidal agent is the combination of nicosulfuron and dicamba, preferably with a ratio of about 10: 1 to about 1 : 10 by weight, more preferably about 5: 1 to about 1 :5, most preferably about 2: 1 to about 1 :2.

4. The herbicidal composition according to claim 1 or 2, wherein the second herbicidal agent is the combination of nicosulfuron and imazaquin, preferably with a ratio of about 10: 1 to about 1 : 10 by weight, more preferably about 5: 1 to about 1 :5, most preferably about 2: 1 to about 1 :2.

5. The herbicidal composition according to claim 1 or 2, wherein the second herbicidal agent is the combination of dicamba and imazaquin, preferably with a ratio of about 10: 1 to about 1 : 10 by weight, more preferably about 5: 1 to about 1 :5, most preferably about 2: 1 to about 1 :2.

6. The herbicidal composition according to claim 1 or 2, wherein the second herbicidal agent is the combination of nicosulfuron, dicamba, and imazaquin, preferably with a ratio of about 1 : 1 : 1 by weight.

7. The herbicidal composition according to any one of claims 1 to 6, wherein the herbicidal composition further comprises an adjuvant and/or carrier, preferably the adjuvant and/or carrier may include one or more surfactants and/or safeners, more preferably the adjuvant and/or carrier may include one or more selected from the group consisting of alkylpolyglycosides, alkylbetaines, alkyl(amidoalkyl)betaines, alkylamidopropyl dialkylamine, ammonium sulfate, and any combination thereof, more preferably the content of the adjuvant is between about 0.01% and about 90% by weight, further more preferably between about 0.05% and about 50%, for example between about 0.1% and about 30%.

8. A method of controlling growth of undesirable vegetation in crops, particularly maize (corn), comprising applying to the locus of the undesirable vegetation, a herbicidally effective amount of the herbicidal composition according to any one of claims 1 to 6.

9. A method of controlling growth of undesirable vegetation in crops, particularly maize (corn), comprising applying to the locus of the undesirable vegetation, an herbicidally effective amount of mesotrione and at least one second herbicidal agent selected from the group consisting of nicosulfuron, dicamba, imazaquin, their salts and any combination thereof. The combinations of mesotrione and nicosulfuron, mesotrione and dicamba are excluded.

10. Use of mesotrione and at least one second herbicidal agent selected from nicosulfuron, dicamba, imazaquin, their salts and any combination thereof in controlling growth of undesirable vegetation in crops, particularly maize.