ES2364022T3 - HERBICIDE COMPOSITIONS. - Google Patents

Abstract

A method for controlling the growth of unwanted plants comprising the joint application to the site of said unwanted plants of dimethenamid and terbutylazine in a herbicidally effective aggregate amount.

Description

The present invention relates to a method for controlling the growth of unwanted plants using the joint application of herbicidal compositions of dimethenamid and terbutylazine comprising dimethenamid and terbutylazine and the use of said compositions in the control of the growth of unwanted plants.

In US Patent 4,666,502, the content of which is incorporated herein for reference purposes only, dimethenamid (FRONTIER®) whose chemical name is 2-chloro-N- (2,4-dimethyl-3-thienyl) -N- (2-Methoxy-1-methyl ethyl) acetamide, processes for its production, herbicidal compositions containing said compound and its use as a herbicide. The dimethenamid compound consists of 4 stereoisomers due to two chiral elements and, thus, can also exist in the form of individual isomers, such as diastereomeric mixtures (1S, aRS (known as S-dimethenamid) and 1R, aRS (known as R -dimethenamid) and as a racemic mixture (1RS, aRS) References to the dimethenamid compound, offered herein, refer to its various forms unless otherwise stated.Diastereomeric mixtures prefer S-dimethenamid.

The term herbicides, as used herein, refers to compounds that fight or control the growth of unwanted plants. This class of compounds can be divided into sub-classes according to the main type or mode of action that the herbicide performs on the plant. For example, according to G.F. Warren of Purdue University, Indiana, USA, herbicides can be classified as auxin transport inhibitors, growth regulating herbicides, photosynthesis inhibitors, pigment inhibitors, growth inhibitors, amino acid synthesis inhibitors, biosynthesis inhibitors of lipids, cell wall biosynthesis inhibitors, rapid cell membrane breakers, as well as miscellaneous herbicides that do not belong to one of the above categories.

EP 0 380 447 describes synergistic combinations comprising dimethenamid and methazol. A. Rahman et al. (Proc. 45th N.Z. Plant Protection Conf. 1992; 84-88), B.L. Wooley (Res. Rep Expert Comm. Weeds East Can; 36 Meet., Vol. 1, 211-212, 1991) and J.E. Shaw et al. (Res.Rep. Expert Comm. Weeds East.Can, 36 Meet., Vol. 1, 395397, 1991) report on weed control with combinations comprising dimethenamid with the active ingredients. atrazine, cyanazine and metribuzin.

It has now been surprisingly found that the joint application of dimethenamid and terbutylazine results in better control, and in some cases of longer duration, of the growth of unwanted plants. This synergistic effect manifests itself in a high degree of control in proportions of joint application that are significantly lower than the proportion of each individual compound required to obtain the same degree of control. In addition, at any given joint application rate, the degree of control is greater than the additive effect obtained for the individual components at the same rate. In some cases, both the speed of activity and the level of control are improved and / or weeds can be controlled that are not controlled by any of the components in economic proportions.

This synergistic effect allows satisfactory control at lower rates of application for each component and even at levels that, if applied to a single component in particular, would provide insufficient control. On the other hand, longer residual control can be achieved.

This gives rise to important economic and environmental advantages in the use of dimethenamid and the herbicide or herbicides used in combination with it.

The joint application can be achieved by using tank mixtures of the previously formulated individual active ingredients, simultaneous or sequential application (preferably 1-2 days) of said formulations or application of pre-formulated and pre-mixed combinations in fixed amounts of the individual active ingredients.

The herbicide used in combination with dimethenamid according to the invention is terbutylazine.

The present invention thus relates to a method to combat or control the growth of unwanted plants or to otherwise regulate the growth of such plants, which comprises the joint application, at a point where it is desired to perform said combat or control, of an aggregate amount, effective to perform a herbicidal or plant growth regulating action, of dimethenamid and terbutylazine.

Of course, the application rates for joint application will vary depending on weather conditions, season, soil ecology, weeds to fight and similar factors, but excellent results can be obtained, for example, with dimethenamid ratios of 0, 1 to 3.0 kg / ha, preferably 0.1 to 2.0 kg / ha, especially 0.25 to 1.5 kg / ha, for example, 0.9 to 1.5 kg / ha in the joint application with proportions for terbutylazine that correspond to or are significantly lower than those recommended for their individual use.

The suitability of specific joint applications for their uses before or after the outbreak and their selectivity will, of course, depend on terbutylazine.

5 The activity of dimethenamid has been described in the aforementioned patents and the activity of suitable herbicidal partners is described in the literature, as well as their commercially available forms (see also CROP PROTECTION CHEMICALS REFERENCE, 9th edition (1993) Chemical & Pharmaceutical Press, NY, NY; The Pesticide Manual, 9th edition (1991), British Crop Protection Council, London; Ag Chem New Product Review, Ag Chem Information Services, Indianapolis, Indiana; Farm Chemicals Handbook, 1993 edition,

10 Meister Publishing Company, Willoughby, Ohio and the like).

The invention also provides herbicidal or plant growth regulating compositions comprising a herbicidally effective aggregate amount of dimethenamid and terbutylazine.

Such compositions contain the active substances in association with agriculturally acceptable diluents. They can be used in solid or liquid forms, for example, in the form of a wettable powder or a concentrate

Emulsifiable, incorporating conventional diluents. Such compositions can be obtained in a conventional manner, for example, by mixing the active ingredient with a diluent and optionally with other formulation ingredients, such as surfactants and oils.

The term "diluents" as used herein represents any liquid or solid, agriculturally acceptable material that can be added to the active constituent to provide an easier or

20 improved, or to achieve a useful or convenient activity intensity. Examples of diluents are talc, kaolin, diatomaceous earth, xylene, non-phytotoxic oils or water.

Particular formulations, to be applied in sprayable forms, such as water dispersible concentrates or wettable powders, may contain surfactants such as wetting and dispersing agents, for example, the condensation product of formaldehyde with naphthalenesulfonate, an alkylarylsulfonate, a

25 ligninsulfonate, an alkyl (fatty) sulfate, an ethoxylated alkylphenol or an ethoxylated fatty alcohol.

In general, the formulations include 0.01 to 90% by weight of active agent or agents and 0 to 20% by weight of agriculturally acceptable surfactant, the active agent consisting of dimethenamid and at least terbutylazine. The concentrated forms of the compositions generally contain between about 2 and 90%, preferably between about 5 and 80% by weight of active agent. Formulation application forms can

30 contain, for example, from 0.01 to 20% by weight of active agent.

When simultaneous, immediately sequential or tank mixing applications are used, the herbicide associate or associates may be used in commercially available forms, if appropriate, and in proportions equivalent to or preferably below those recommended by the manufacturer or in the references cited previously. The dimethenamid compound can also be applied in a form

35 commercially available (for example, as the FRONTIER® herbicide) or as formulated, for example, as described in the aforementioned US 4,666,502.

In the joint application according to the present invention, other compounds having biological activity can also be included, for example, compounds having insecticidal or fungicidal activity.

The preferred mode of application is the prepared tank mix, for example, by adding dimethenamid to a

A tank containing the other herbicide associate and a suitable surfactant or vice versa, depending on the type of herbicide associate chosen. It is advisable to consult the labels of the partners to be mixed and perform compatibility tests before mixing.

Depending on the choice of partners for joint application, an activity can be achieved before the outbreak and after the outbreak in a wide variety of broadleaf weeds and grasses. Examples of such bad

45 herbs are:

Agropyron repens Grama Brachiaria platyphylla Gambutera Bromus spp. for example, hairy bromine Cenchrus spp. for example, cadillo cart, egyptian grass Digitaria spp. for example, summer grass, small garrachuelo, chicken foot

Echinochloa crus-galli

Cerreig

Eleusine indica

Foot of chicken

Eriochloa spp.

for example, malojilla

Leptochloa filiformis

salted avocado

Oryza sativa

Red rice

Panicum spp.

for example, American straw, surbana and Texas straw, common millet

Poa annua

Hairy

Setaria spp.

for example, giant clam, Italian panizo, glaucous clam, almo-

Verticillate fence, green clam

Sorghum almum

black sorghum

Sorizhum bicolor

common sorghum

Halepense Sweepstakes

Canota

Urochloa panicoides

nettle

Acanthospermum hispidum Cacharro

Amaranthus spp.

for example, white ash, white soup, amaranth, prostrate liver,

 spiny sludge

Ambrosia artemisiifolia

Ragweed

Bidens pilosa

Romerillo

Capsella bursa-pastoris

shepherd's bag

Chenopodium album

white ash

Cleome monophylla

larkspur

Commelina spp

for example, canutillo

Crotalaria sphaerocarpa

wild alfalfa

Datura stranionium

eggplant of the devil

Desmodium tortuosum

Florida canutillo

Euphorbia nutans

Milkweed

Euphorbia maculata

spotted milk

Galinsoga parviflora

gallant soldier

Ipomea spp.

for example, red trumpet, sigh

Lamium purpureum

Dead nettle, purpurea

Matricaria chamomilla

Niagarza

Mollugo verticillata

grass carpet

Papaver rhoeas

Poppy

Polygonum spp.

for example, polygon, annual polygon, climbing polygon, one hundred knots

Portulaca oleracea

common purslane

Richardia Scabra

White Ipecac

Schkuhria pinnata

bitter pichana

AIDS spinosa

Prickly mallow

Solanum spp.

for example, black solano, green solano, white solano

Middle stellaria

grass hen

Tagetes minuta

chinchilla (Khaki weed)

Cyperus esculentis

Common chufa

Cyperus iria

rice cipero

In addition, the following weeds can also be controlled when mixing partners are used.

adequate.

Abutilon theophrasti Hibiscus trionum

Jute of the China flower one hour

Avena fatua

crazy oatmeal

Sinapis alba

white mustard

Xanthium strumarium large abalone Cassia obtusifolia winter bean Apera spica-venti Apera Campsis radicans grass trumpet Rottboellia exaltata Treadmill Cynodon dactylon grass of Spain Lespedeza spp. for example, lespedezas Trifolium spp. for example, clovers Hippuris vulgaris aquatic horsetail Asclepias spp. for example, Spanish flag Salvia spp. for example, sage from the meadows Salsola iberica Russian thistle Convolvulus arvensis minor corgela Cirsium arvense thistle condidor Proboscidea louisianica shepherd needle Senecio spp. for example, common cane grass Chorispora tennela Blue mustard Alopecurus myosuroides foxtail Sisymbrium altissimum Female mustard Caperionia palustres grass Texas

Crop selectivity will also normally depend on the choice of partners. The dimethenamid compound exhibits excellent selectivity in crops of corn, soybeans and other various crops.

Examples of particular partners for joint application with dimetenamid include those selected from one or more of the types listed under a) to w) below.

to.

 benzoic acids, for example dicamba

b.

 picolinic acids and related compounds, for example picloram, triclopyr, fluroxypur, clopyralid

C.

 phenoxis, for example 2,4-D, 2,4-DB, triclopyr, MCPA, MCPP, 2,4-DP, MCPB

d.

 other chloroacetamides, for example alachlor, acetochlor, metolachlor, diethalyl, propachlor, butachlor, pretilachlor, 10 metazachlor, dimetachlor, especially metolachlor, alachlor, acetochlor

and.

 amides, for example propanil, naptalam

F.

 carbamates, for example asulam

g.

 thiocarbamates, for example EPTC, butylate, cycloate, molinate, pebulate, thiobencarb, trialate, vernolate

h.

 nitriles, for example bromoxynil, ioxynil 15 i. ureas, for example diuron, tidiazuron, fluometuron, linuron, tebutiuron, forchlorfenuron

j.

 triazines, for example atrazine, metribuzine, cyanazine, simazine, prometon, ametrine, promethine, hexazinone

k.

 diphenyl ethers, for example acifluorfen, phomesaphene, lactophen, oxyfluorfen

l.

 dinitroanilines, for example trifluralin, prodiamine, beneficin, etalfluralin, isopropalin, oxizaline, pendimethalin

m.

 sulfonylureas, for example rimsulfuron, metsulfuron, nicosulfuron, triasulfuron, primisulfuron, bensulfuron,

20 chlorimuron, chlorsulfuron, sulfometuron, tifensulfuron, tribenuron, etametsulfuron, triflusulfuron, clopirasulfuron, pyrazulfuron, prosulfuron (CGA-152005), halosulfuron, metsulfuron-methyl, chlorimuron-ethyl

n.

 imidazolinones, for example imazaquin, imazametabenz, imazapir, imazetapir

or.

 cyclohexanediones, for example setoxidim

p. aryloxyphenoxies, for example fluazifop 25 q. bipyridyls, for example paraquat, diquat

r.

 pyridazinones, for example norflurazone

s.

 uracils, for example bromacil, terbacil

t.

 isoxazolones, for example clomazone

or.

several, for example glyphosate, glufosinate, methazole, paclobutrazol, bentazone, desmedifam, fenmedifam, pyrazone,

30 pyridate, amitrole, fluridone, DCPA, dithiopyr, pronamide, bensulide, napropamide, sidurone, flumetsulam, cletodim, diclofopmethyl, phenoxaprop-ethyl, haloxyfor-methyl, quizalofop, diclobenyl, isoxabenz, pathochlorazone, oxadiazonazorazate, quadotolotholzoazorazate, quadiazonazozone , phosamine, DSMA, MSMA

v. tricetons and diones of the type described in US Patents 4,695,673, 4,869,748, 4,921,526, 5,006,150, 5,089,046, US Patent Applications 07 / 411,086 (and EP-A 338 992); and 07 / 994,048 (and EP-A 394 889 and EP-A 506 907), as well

35 as EP-A 137 963; EP-A 186 118; EP-A 186 119, EP-A 186 120; EP-A 249 150; EP-A 336 898; the contents of each of which are incorporated herein by reference. Examples of such tricetonas and diones are sulcotrione (MIKADO®), whose chemical name is 2- (2-chloro-4-methanesulfonylbenzoyl) -1,3cyclohexanedione; 2- (4-Methylsulfonyloxy-2-nitrobenzoyl) -4,4,6,6-tetramethyl-1,3-cyclohexanedione; 3- (4-Methylsulfonyloxy-2-nitrobenzoyl) -bicyclo [3,2,1] octane-2,4-dione; 3- (4-Methylsulfonyl-2-nitrobenzoyl) -bicyclo [3,2,1] octane-2,4-dione; 4- (4-Chloro-2-nitrobenzoyl) -2,6,6-trimethyl-2H-1,2-oxazine-3,5 (4H, 6H) dione; 4- (4-methylthio-2-nitrobenzoyl) -2,6,6-trimethyl-2H-1,2

5 oxazine-3,5 (4H, 6H) -dione; 3- (4-methylthio-2-nitrobenzoyl) -bicyclo [3,2,1] octane-2,4-dione; 4- (2-Nitro-4trifluoromethoxybenzoyl) -2,6,6-trimethyl-2H-1,2-oxazine-3,5 (4H, 6H) -dione

w. Compounds of the type described in US Patent Applications 08 / 036,006 (and EP-A 461 079 and EP-A 549 524); EPA 315 889; and PCT Application No. 91/10653, the contents of each of which are incorporated herein by reference, including, for example, 3 - [(4,6-dimethoxy-2-pyrimidinyl) hydroxymethyl] -N- methyl-2-pyridinecarboxamide; 4,7-dichloro-3- (4,6-dimethoxy-2-pyrimidinyl) -3-hexanoyloxyphthalide; 3 - [(4,6-di-methoxy-2-pyrimidinyl) carbonyl] -N, N-dimethyl-2-pyridinecarboxamide; 3,6-Dichloro-2 - [(4,6-dimethoxy-2-pyrimidinyl) carbonyl] benzoic acid; 6-Chloro-2 - [(4,6-dimethoxy-2-pyrimidinyl) thio] benzoic acid (also known as DPX-PE350 or pyrithiobac) and its salts.

It will be appreciated that mixtures of dimethenamid with more than one herbicide, for example three-way mixtures 15 are also included within the scope of the invention.

The mixing partner is terbutylazine.

According to the desired spectrum of weeds, the timing of application and similar factors, terbutylazine and a suitable mixing partner.

Example 1

The active ingredients are weighed and dissolved in a stock solution consisting of acetone: 1: 1 deionized water, and 0.5% adjuvant mixture consisting of SPAN® 20: TWEEN® 20: TWEEN® 85, 1: 1: 1 surfactants . Dilutions are made from this stock solution in order to prepare spray solutions consisting of single doses of the individual or combined active ingredients. Each dose is applied simultaneously by means of a regulated linear track sprayer to deliver a spray volume of

25 600 liters / ha to the foliage of the selected weed seedling species, application after the sprout, and to the soil surface that has previously been sown with seeds, application before the sprout. The seedlings used are grown to develop plants in the phase that goes from two leaves to the beginning of the three leaves. The development phase of each seedling is noted at the time of application. After application, the treated plants are transferred to the greenhouse and kept there until the end of the experiment within four weeks. Damage symptoms are noted after two and ten days after application after the outbreak and fourteen days after application before the outbreak. Visual classifications in percentage of crop damage and weed control are made after twenty-eight days after application after the outbreak and fourteen and twenty-eight days from application before the outbreak.

The joint application of dimethenamid with other specific active ingredients, such as those indicated

35 above, it results in improved herbicidal effects compared to the individual application of each active ingredient.

Example 2 (Comparative example, which is not part of the invention)

A field test is carried out using FRONTIER® 7.5 EC and ACCENT® 75 WDG in the control of large cereal cereal. The application is as a combination mixed in the same tank in an early posemergence of weeds (phases of 3 and 4 leaves). The application rates of i.a. they are 1.5 and 0.75 kg / ha for dimetenamide and 37.2 and 19.2 g / ha for nicosulfuron. The combined application of 0.75 kg / ha of dimetenamide and 19.2 g / ha of nicosulfuron gave 85% control with insignificant damage to cereal compared to 35% of nicosulfuron applied only at 19.2 g / ha and 72 % for dimetenamide at a higher rate of 1.25 g / ha. The combined application at the higher rate of dimetenamide with 37.2 g / ha of nicosulfuron gave an even more drastic effect with

45 95% control compared to 72% for dimetenamide and only 45% for nicosulfuron, each alone.

Example 3 (Comparative example, which is not part of the invention)

Small field units in a cornfield, infested with echinochloa crus galli and solanum nigrum, are sprayed with a mixed suspension in the same dimetenamide and sulcotrione tank. The weed phase is "total stifling" for echinochloa crus galli and "8 leaf phase" for solanum nigrum. The size of the land is 8 meters long and 3 meters wide. The application rates are 1.1 kg / ha of dimetenamide and 0.15 kg / ha of sulcotrione. Seven days after treatment, the efficacy is evaluated, both as control of weeds and tolerance of crop plants.

In this test the control of echinochloa was between 93 and 98%, and the control of solanum was between 91 and 93% in three repetitions, while the damage of the corn plants was always below 10%.

Example 4 (Comparative example, which is not part of the invention)

Small field units in a cornfield, infested with echinochloa crus galli, solanum nigrum and

5 chenopodium album, are sprayed with a suspension mixed in the same tank of dimetenamide, sulcotrione and atrazine. The weed phase is "total choking" of echinochloa and "6-8 leaf phase" for solanum and chenopodium. The size of the land is 8 meters long and 3 meters wide. The application rates are 1.08 kg / ha of dimetenamide, 150 or 210 g / ha of sulcotrione and 750 g / ha of atrazine. 14 days after treatment the efficacy is evaluated.

10 The results (as a percentage of control) were as follows:

image 1

The synergistic effect is clearly visible at lower rates of sulcotrione, resulting in an almost double degree of control, compared to the expected additive efficiencies. For higher rates of sulcotrione (> 300 g / ha), only the additive effect is visible since the total control is 100%.

Example 5 (Comparative example, which is not part of the invention)

A field test is carried out on plots (2 x 20 m) planted with sugarcane and infested with cyperus rotundus in the first or second phase of growth and sprayed with a backpack sprayer in different concentrations in a mixture in it tank. The quantity of liquid spray broth is 400 l / ha.

The application rates are 2.7 kg / ha of dimethenamid with 60 g / ha of chlorimuron or with 1.6 kg / ha of a fixed ratio mixture of chlorimuron and diuron (1:19) that is commercially available as FRONT® . Visual evaluation is done 30 or 60 days after treatment (DDT) in percentage of control. The expected additive effect value is calculated according to the Colby method:

image2

The results obtained indicate that synergistic effects are obtained with the double mixture (dimetenamide / chlorimuron), as well as the triple mixture (dimetenamide / chlorimuron / diuron).

Claims (4)

1. A method to control the growth of unwanted plants comprising the joint application to location of said unwanted dimethenamid and terbutylazine plants in an herbicidally effective aggregate amount.

2.

A method according to claim 1, wherein the amount of dimethenamid is 0.1 to 3.0 kg / ha.

3.

A herbicidal composition comprising a herbicidally effective amount of dimethenamid and terbutylazine and an agriculturally acceptable carrier.

4. A composition according to claim 3, characterized in that it contains dimethenamid and terbutylazine in an amount that produces a synergistic herbicidal effect.