PL176082B1 - Synergetic herbicide and method of fighting against growth of undersirable flora - Google Patents

Abstract

Synergistic herbicide agent, containing an active substance, typical supporting agents and a carrier allowed for agricultural use, characterised in that it contains herbicidally effective joint amount of dimetenamid and another herbicide chosen from triketone and dyon group, including 2- (2-chloro-4-methano-sulphonylobenzoilo)-1,3- cyclohexanedyone; 2-(4-methylosulphonyloksy-2-nitrobenzoilo)-4,4,6,6-tetramethylo-1,3-cyclohexanedyone; 3-(4-methylosulphonyloksy-2-nitrobenzoilo)-bicyclo [3.2.1]oktano-2,4-dyon; 3-(4-methylosulphonylo-2-ni-trobenzoilo)-bicyclo [3.2.1] oktano-2.4-dyon; 4-(4-chloro-2-nitrobenzoilo)-2.6.6-trimethylo-2H-1,2-oxasino-3,5(4H, 6H) dyon; 4-(4-methylotio-2-nitrobenzoilo)-2,6,6-trimethylo-2H-1,2-oxasino-3,5-(4H, 6H)-dyon; 3-(4-methylotio-2-nitrobenzoilo)-bicyclo [3.2.1] oktano-2,4-dyon; 4-(2-nitro-4-trifluorometoksybenzoilo)-2,6,6-trimethylo-2H-1,2-oxasino-3,5 (4H, 6H) - dyon; whereby the weight ratio of the herbicide chosen from triketone and dyon group to dimetenamid is 1:2-1:10 and the amount of active substances is 0.01-90 weight percent. 4. Method for fighting undesirable vegetation, characterised in that synergistic herbicide is applied where undesirable vegetation grows, characterised in that it contains herbicidally effective joint amount of dimetenamid and another herbicide chosen from triketone and dyon group, including 2- (2-chloro-4-methano-sulphonylobenzoilo)-1,3- cyclohexanedyone; 2-(4-methylosulphonyloksy-2-nitrobenzoilo)-4,4,6,6-tetramethylo-1,3-cylkohexanedyone; 3-(4-methylosulphonyloksy-2-nitrobenzoilo)-bicyclo [3.2.1]octano-2,4-dyon; 3-(4-methylosulphonylo-2-ni-trobenzoilo)-bicyclo [3.2.1] oktano-2.4-dyon; 4-(4-chloro-2-nitrobenzoilo)-2.6.6-trimethylo-2H-1,2-oxasino-3,5(4H, 6H) dyon; 4-(4-methylotio-2-nitrobenzoilo)-2,6,6-trimethylo-2H-1,2-oxasino-3,5-(4H, 6H)-dyon; 3-(4-methylotio-2-nitrobenzoilo)-bicyclo [3.2.1] oktano-2,4-dyon; 4-(2-nitro-4-trifluorometoksybenzoilo)-2,6,6-trimethylo-2H-1,2-oxasino-3,5 (4H, 6H) - dyon; whereby the weight ratio of the herbicide chosen from triketone and dyon group to dimetenamid is 1:2-1:10 and the amount of active substances is 0.01-90 weight percent, whereby dimetenamid present in the agent is used in the amount of 0.1-3 kg/hectare and triketone present in the agent is used in the amount of 0.01-2 kg/hectare.

Description

The present invention relates to a synergistic herbicide and a method for controlling undesirable vegetation.

Dimethhenamide (FRONTIER®) with a chemical name of 2-chloro-N- (2,4-dimethyl-3-thienyl) N- (2-methoxy-1-methylethyl) acetamide, a method of its preparation, containing herbicidal compositions and their use as agents herbicides are described in U.S. Patent No. 4,666,502, which is incorporated herein by reference. Dimethenamide consists of 4 stereoisomers due to two chiral elements and can also exist as individual isomers as well as diastereomeric mixtures (1S, aRS (known as

S-dimethhenamide) and 1R, aRS (known as R-dimethyleneamide) and as a racemic mixture (1RS, aRS). Reference herein to dimethhenamide applies to its various forms unless otherwise noted. Among the diastereoisomeric mixtures, mixtures of S-dimethenoamide are preferable.

The term herbicides as used herein refers to compounds which combat or regulate undesirable growth in vegetation. This class of compounds can be subclassed according to the main type and mode of action that the herbicide has on plants. For example, according to G. F. Warren of Purdue University, Indiana, St. For example, herbicides can be classified as auxin transfer inhibitors, herbicides, growth regulators, photosynthesis inhibitors, pigment inhibitors, growth inhibitors, amino acid synthesis inhibitors, lipid biosynthesis inhibitors, cell wall biosynthesis inhibitors, rapid membrane disruptors, as well as mixed herbicides that are not they fall under one of the above categories.

It has now surprisingly been found that the joint application of dimethhenamide and at least one other herbicide results in better, and in some cases longer lasting, control of undesirable plant development. By itself, the synergistic effect shows a high degree of control at the co-administered doses which are significantly lower than the doses of each individual compound needed to obtain the same degree of control. Furthermore, for any given co-applied dose, the degree of control is greater than the added effect obtained with the individual components at the same doses. In some instances, both the speed of action and the level of damage are increased, and / or weeds that are not damaged by any of the components at economically reasonable doses may be destroyed.

This synergistic effect allows for satisfactory control with the use of reduced doses of each component and even in amounts which, if used for a particular component alone, would give unsatisfactory destruction. In addition, a longer residual control can be achieved. This provides significant economic and environmental benefits when using dimethhenamide and the herbicide (s) used in conjunction with it.

Co-application is achieved by mixing the individual active ingredients formulations in a tank or by consecutive (preferably 1-2 days) application of such formulations or by applying a pre-mix made from a predetermined combination of the individual active ingredients.

176 082

Examples of herbicides that can be used in combination with dimethhenamide are:

1. auxin transfer inhibitors, e.g. naptalam

2. growth regulators including 1) benzoic acids, e.g. dicamba; b) phenoxy acids i) acetic acid type e.g. 2,4-D, MCPA, ii) propionic acid type e.g. 2,4-DP, MCPP, iii) butyric acid type e.g. 2,4-DB, MCPB; c) picolinic acids and related compounds, e.g. picloram, triclopyr, fluoroxypyr, clopyralid,

3. photosynthesis inhibitors including a) s-triazines i) chloro substituted, e.g. atrazine, simazine, cyanazine, ii) methoxy substituted, e.g. prometone, iii) methylthio substituted e.g. amethrin; promethrin; b) other triazines, e.g. hexazinone, metribuzin; c) substituted ureas, e.g. diuron, fluometruon, linuron, tebuthiuron, thidiazuron, forchlorfenuron; d) uracils, e.g. bromacil, terbacil; e) others, e.g. bentazone, desmidefam, phenmedipham, propanil, pyrazone, pyridate,

4. pigment inhibitors including a) pyridazinones, e.g., norflurazone; b) isoxazolones, e.g. clomazone; c) others, e.g. amitrole, fluridone,

5. growth inhibitors including a) mitotic disruptors i) dinitroanilines, e.g. trifluralin, prodiamine, benefin, etalfluralin, isopropalin, oryzalin, pendimethalin, ii) others, e.g. DCPA, dithiopyr, thiazopyr, pronamide; b) inhibitors of sprouting from germinating seedlings i) thiocarbamates, e.g. EPTC, butylate, cyclohe, molinate, pebulate, thiobencarb, triallate, vemolat; c) seedling root inhibitors only, e.g. bensulite, napropamide, siduron; d) seedling root and shoot inhibitors, including chloroacetamides, e.g. alachlor, acetochlor, metolachlor, diethatyl, propachlor, butachlor, pretilachlor, metazachlor, dimethachlor and others, e.g. cinnmethylin,

6. amino acid synthesis inhibitors including a) glyphosate, glufosate; b) sulfonylureas, e.g. rimsulfuron, metsulfuron, nicosulfuron, triasulfuron, primisulfuron, bensulfuron, chlorimuron, chlorsulfuron, sulfometuron, thifensulfuron, tribenuron, etametsulfuron, trisulfuron, clopyrasulfonulfuron, chlorosulfuron, prosulfuron, clopyrazulfonulfuron, prosulfuron, pyrazimuronulfuron, pyrazimurulfuron; c) sulfonamides, e.g. flumetsulam (a.k.a. DE498); d) imidazolones, e.g. imazaquin, imazametabenz, imazapyr, imazethapyr,

7. lipid biosynthesis inhibitors including a) cyclohexanediones, e.g., sethoxydim, clethodim; b) aryloxyphenoxy compounds, e.g. butyl-P-fluazifop, clethodim, methyldiclofop, methyl-haloxyfop, quisalophop; c) others, e.g. ethyl-fenoxaprop,

8.inhibitors of cell wall biosynthesis, e.g. dichlobenil, isoxaben,

9. wall-membrane abrupt disruption means including a) bipyridiliums, e.g. paraquat, diquat; b) diphenyl ethers, e.g., acifluorfen, fomesafen, lactophen, oxyfluorfen; c) glutamine synthase inhibitors for example glufosinate; d) others, e.g. oxadiazone,

10. mixed ol ^^ erouj4 ^{ce a} ) carbamates, nn. azulam; b) nitriles e.g. bromoxynil, ioxynil; c) hydanthidisis and derivatives; d) various, e.g. paclobutrazole, etofumazate, quisoclsrak (akn BAS514), difenzoquat, endotal, fosamim, DSMa, MSMA,

11 others

a) triketones and diones of the type described in US Patent Nos. 4,695,673; 4,869,748; 4,921,526; 5,006,150; 5,089,046, in 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 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; which are provided herein by reference. Examples of such triketones and dions are sulcotrione (MIKADO®), which has the chemical name 2- (2-chloro-4-methanesulfosylbenzoyl) -1,3-cyclohexαnodisn; 2- (4-methylsulfonyloxy-2-nitrobezzooyl) -4,4,6,6-tetramethyl-1,3-cyclohexanedione; 3- (4-methylsulfonyloxy-2-nitrobenzoyl) -bicyclo [3.2.1] octane-2,4-dione; 3- (4-methylsulfosl-2-nitrobezzoyl) -0icyclo [3.2.1] octnzo-2,4-dione; 4- (4-chloro-2-nitrobenzoyl-2,6,6-trimethyl-2H-1,2-oxazzo-3,5- (4H, 6H) dione; 4- (4-methylthio-2-nitrobezzooylob-2) , 6,6-trimethyl-2H1,2-oxazzo-3,5- (4H, 6H) -dione; 3- (4-methylthio-2-zitrobezzsils) ^ bicyclo [3.2.1] octalone-2,4 -dione; 4- (2-nitro-4-trifluoromethoxybezzooyl) -2,6,6-trimethyl-H-1,2-oxazine-3,5 (4H, 6H) -dione.

b) compounds of the type described in US Patent Application Nos. 08/036 006 (and EP-A-461 079 and EP-A-549 524); EP-A-315,889; and PCT Application No. 91/10653, which are incorporated herein by reference including, for example, 3 - [(4,6-dimethoxy-2-pyrimidisyl) hydroxymethyl] -N-methyl-2-pyridinecarboxarmide; 4,7-dichioro-3- (4,6-dimethoxy-2-pyrimidisyl) -3-hexazooyloxyphthalid;

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3 - [(4,6-dimethoxy-2-pyrimidinyl) cy-bonyl] -N, N-dimethyl-2-pyridinecarboxamide; acid

3,6-dichloro-2 - [(4,6-dimethoxy-2-pyrimidinyl) carbonyl] benzoic; 6-chloro-2 [(4,6-dimethoxy-2-pyrimidinyl) thio] benzoic acid (a.k.a. DPX-PE350 or pyriobak) and its salts.

The invention thus relates to a method of combating or regulating undesirable vegetation growth or otherwise regulating the growth of vegetation, which comprises co-application to a site where such eradication or control is desired, herbicidally effective or growth-regulating amount of combined methyl amine with at least one other herbicide. .

The method of controlling undesirable vegetation according to the invention consists in applying an energetic herbicide to the site of the undesirable vegetation, characterized in that it comprises a herbicidally effective combined amount of dimethhenamide and another herbicide selected from the group of triketones and dions, including 2- (2). -chloro-4-methanesulfonylbenzoyl) -1,3-cyclohexanedione; 2-4-methylsulfonyloxy-2-nitrobozoyl) -4,4,6,6-tetramethyl-1,3-cyclohexanedione; 3- (4-methanesulfonyloxy-2-nitrobenzoyl) -bicyclo [3.2.1] oatane-2,4-dione; 3 ((4-methylsulίΌnyl-2-nitrobeozoyl) -bicn-clo [3.2.1] octane-2,4-dione; 4- (4-chloro-2-nitrobenzoyl) -2,6,6-trimethyl-2H- ], 2-oxychin-3,5 (4H, 6H) dione; 4 ((4-meth) r (o-2-yiΓrobenzoyl) -2,6,6-trimethyl-2H-1,2-oxazine-3, 5- (4H, 6H) yron; 3- (4-methylthio-2-ytrobeyzoyl) -brcyalo [3.2.1] octane-2,4-dione; 4 ((2-nirro-4-rrifluoromethoxybenzoyl) -2.6 , 6-trimethyl-2H-1,2-oxysine-3,5 (4H, 6H) -dione, the weight ratio of the herbicide selected from the group of triketones and diones to dimenosmeride is 1: 2-1: 10 and the substances the active substances are present in the amount of 0.01-90% by weight, but the dimethenesimide present in the agent is used in the amount of 0.1-3.0 kg / ha, and the riketone present in the agent in the amount of 0.01-2 .0 kg / ha.

Preferably, an agent is applied characterized in that the active ingredients are dimethhenamide and sulfurione, the drmeosmrd in the center being 0.9-1.5 kg / ha and the sulfurion in the center using is at the rate of 0.15-0.45 kg / ha.

Preferably, an agent is applied characterized in that the dimethenesimide present in the agent is applied in an amount of 0.1-2.0 kg / ha, in particular 0.25-1.5 kg / ha.

Preferably, the agent is applied, characterized in that the aretone present in the agent is applied in an amount of 0.1-1.0 kg / ha, in particular 0.1-0.6 kg / ha.

Co-administered doses will of course depend on the climatic conditions, season, soil ecology, weeds to be controlled and the like, however effective results can be obtained, e.g. with dimeienosmry doses of 0.1 to 3.0 kg / ha, preferably 0.1 to 2 , 0 kg / ha, in particular 0.25 to 1.5 kg / ha, e.g. 0.9 to 1.5 kg / ha, when applied together with the corresponding herbicide application rates of the partner and are significantly lower than those recommended. individual use.

The suitability of a particular pre-emergence or post-emergence joint application and the selectivity will of course depend on the partner used.

The activity of yimethenoamide is described in the above-mentioned patents, and the respective herbicidal partners are described in the literature or in commercial forms (cf. 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 Reciew, Ag Chem Information Services, Indianapolis, Indiana; Farm Chemicals Hacdbook, 1993 Edition, Meister Publishing Company, Willoughby, Ohio and the like).

The invention also includes herbicidal or plant growth regulating compositions comprising herbicidally effective amounts of a combined yrmethene amide and at least one other herbicide.

A synergistic herbicide containing active ingredient, conventional adjuvants and an agriculturally acceptable carrier, according to the invention is characterized in that it comprises a herbicidally effective combined amount of yimienamide and another herbicide selected from the group of -rkeons and dions, including 2- (2-chloro -4-methanesulfonylbenzoyl) -1,3cnklohexsnodione; 2-4-me-y (sulfonyl (oxy-2-nitrobenzoyl) -4,4,6,6-thiramethyl-1,3-cyclohexanedione; 3- (4-methylsulfonyloxy-2-nitrobenzoyl) -bicyclo [3.2. 1] oxno-2,4-dione; 3- (4-methylsulfonyl-2-nitrobenzoyl) -bicyclo [3.2.1]] ^^ 1-ο ^ ο - ^, ^ζ ^ -0ϊο ^^; 4- (4- chlc) ΓΌ-2-niirobene), 6-6) -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-oxazine-3,5- (4H, 6H) -dione; 3 ((4-methylthio-2-nitrobenzoyl) -bicyclo [3.2.1] octane-2,4-dione; 4- (2snitro (4-triftuoloxybenzoyl) -2,6,6-trimethyl-2H-1,2- oxazine-3,5 (4H, 6H) -dione, wherein the weight ratio of the herbicide selected from the group of triketones and diones to dimethhenamide is 1: 2-1: 10 and the active ingredients are present in an amount of 0.01-90% by weight.

The active ingredients preferably contain sulcotrione and dimethhenamide.

Such compositions contain the active ingredients in combination with agriculturally acceptable diluents. They can be used either in solid or liquid form, e.g. in the form of a wettable powder or an emulsifiable concentrate containing conventional diluents. Such compositions may be prepared in a conventional manner, e.g. by mixing the active ingredient with a diluent and optionally other formulation ingredients such as surfactants and oils.

The term diluents as used herein means any agri-acceptable liquid or solid material that can be added to the active ingredient to provide easier or better forms of application, or to achieve a useful or desired potency. Examples of diluents are talc, kaolin, diatomaceous earth, xylene, non-phytotoxic oils or water.

Particular formulations for spray application, such as water-dispersible concentrates or wettable powders, may contain surfactants such as wetting and dispersing agents, e.g., formaldehyde condensation with naphthalenesulfonate, alkylarylsulfonate, lignin sulfonate, fatty alkyl sulfate, ethoxylated alkylphenol or ethoxylated alkylphenol fatty alcohol.

In general, the formulations contain from 0.01 to 90% by weight of active ingredient (s) and from 0 to 20% by weight of agriculturally acceptable surfactant. Concentrated forms of the compositions generally contain between about 2 and 90%, preferably between about 5 and 80% by weight of active ingredient. Formulations in application form may, for example, contain from 0.01 to 20% by weight of active ingredient.

When used simultaneously, in succession or in tank mixes, the herbicidal partner (s) may be used, where appropriate, in a commercially available form and at dosages equivalent or preferably lower than those recommended by the manufacturer or in the publications mentioned above.

Dimethhenamide can also be used in its commercial form (e.g. as FRONT1ER® herbicide or prepared e.g. as described in the above-mentioned USP 4,666,502.

Other compounds having a biological effect, for example compounds having an insecticidal or fungicidal activity, can also be included in the common use according to the invention.

The preferred method of application is to prepare a tank mixture, e.g. by adding dimethanamide to a tank containing another partner herbicide and a suitable surfactant or vice versa depending on the type of partner herbicide selected. It is recommended to analyze the indicated uses on their packaging and to conduct a compatibility test before mixing partners.

Depending on the choice of co-used partners, pre-emergence and post-emergence effects can be achieved against a wide range of broadleaf and grass weeds. Examples of such weeds are:

- proper peiz

- turf grass

- stokłosa, e.g. s ^^ c ^ k.łc ^ s ^ a roof

- turf grass - spark

- stickman, e.g. bloody scabbard, threadlike scabbard

- one-sided weed

- crouch

- Coffee maker

- e ^ jto ^ t ^ łlk ^ a

Agropyron repens Btpchiaria platyipliin Bromus spp Cenchtui spp

Daciylocieniam aegyptium Digitaria spp Echinochloa crus-galli Ele ^ ine indica Eriochloa spp Leptochloa filifotmis

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Oryza sativa - red rice

Panicum spp - millet, e.g.

Poa annua - annual panicle

Setaria spp - trichinella, e.g. Trichinella beetle, blue trichinosis, trichinella trichinella, green trichinosis

Sorghum almum Sorghum bicolor Sorghum halepense - Aleppo sorghum

Urochloa panicoides Acanthospermum hispidum Amaranthus spp - szŁadat, e.g. l ^ l ^ i <^ (^^, s ^ zalat szonstiti, small-flowered shark

Ambrosia artemisiifolia - haughty idol

Bidens pilosa - hairy clutch

Capsella bursa-pastoris - common steak

Chenopodium album - white quinoa

Cleome monophylla Commelina spp Crotalaria sphaerocarpa Datura stramonium - Datura

Desmodium tortuosum Euphorbia nutans Euphorbia maculata Galinsoga parnilom - Japanese yellow-flower

Ipomea spp - wolf, e.g. bindweed

Lamium purpureum - its purity

Matricaria chamomilla - common chamomile

Mollugo verticillata Papaver rhoeas - poppy seed

Polygonum spp - Trieste e.g. sorrel knotweed, knotweed, bird knotweed

Portulaca oleracea - common purslane

Richardia scabra Schkuhria pinnata Sida spinosa - thorny syd

Solanum spp - nightshade, e.g. black nightshade, hairy nightshade, silver-leaved nightshade

Stellaria media - common starfish

Tagetes minuta Cyperus esculentis - yellow tiger

Cyperus iria Furthermore, by mixing the appropriate partners, the following weeds can also be controlled:

Abutilon theophrasti - clone (velvetleaf)

Hibiscus trionum - southern ketmja

Avena fatua - deaf oats

Sinapis alba - light mustard

Xanthium strumarium - common turnip

Cassia obtusifolia Apera spica-venti - grain broom

Campsis radicans Rottboellia exaltata - Rottboellia scabies

Cynodon dactylon - canine proper tooth

Lespedeza spp - Japanese clover

Trifolium spp - clover

Hippuris vulgaris - common spread

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- sage

- barbed brine

- morning glory

- caution po ^ y

- old man. e.g. the common old man

- blue mustard

- sniff after ^ y

- shllisz [^; ^ inK ^ ńslii

Asclepias spp Salvia spp Salsola iberica Convolvulus arvensis Crisium arvense Proboscidea louisianica Senecio spp.

Chorispora tennela Alopecurus myosuroides Sisymbrium altissimum

Caperionia palustris Crop selectivity will usually depend on partner selection. Dimethenamide shows excellent selectivity in grain (maize), soybeans and several other crops.

Specific examples of co-use partners with dimethhenamide are products selected from one or more of the types listed below from a) to w):

a.benzoic acids, e.g. dicamba,

b.Picolinic acids and related compounds, e.g. picloram, triclopyr, fluroxypur, clopyralid,

c. phenoxy derivatives, e.g. 2,4-D, 2,4-DB, triclopyr, MCPA, MCpP, 2,4-dP, MCPB,

d. other chloroacetamides, e.g. alachlor, acetochlor, metolachlor, diethatyl, propachlor, butachlor, pretilachlor, metazachlor, dimethachlor, especially metolachlor, alachlor, acetochlor,

e. amides, e.g. propanil, naptalam,

f. carbamates, e.g. asulam,

g. thiocarbamates, e.g. EPTC, butylate, cycloth, molinate, pebulate, thiobencarb, triallate, wemolat,

h. nitriles, e.g. bromoxynil, ioxynil,

i. ureas, e.g. diuron, thidiazuron, fluometuron, linuron, tebuthiuron, forchlorfenuron,

j. triazines, e.g. atrazine, methribuzin, cyanazine, simazine, prometone, amethrin, promethrin, hexazinone,

k. diphenyl ethers, e.g. acifluorfen, fomesafen, lactophen, oxyfluorfen,

l. dinitroanilines, e.g. trifluralin, prodiamine, benefiben etaHaueahna, isopaopidine, oxisalin, pepdimetalipa,

m. sulfonylureas, e.g. rimsulnurop, measulnuron, picosulfuron, triasulfuron, primisulfuron, bepsulfurop, chlorsulfuron, sulnomethuran, thifensulfurop, trlbepuran, etametsulfuron, triflusulfuron, clopyrasulfuron, etametsulfuron, triflusulfuron, clopyrasulfuron, chlorosulfuron, methylpyrasulfuron, chloroprosulfuron, methylthrosulfuron, methylchlorosulfuron, chlorosulfuron, methyl-sulfur2005

n. imidazolinones, e.g. imazaquin, imazametabenz, imazapyr, imazethapyr,

o. cyclohexanediones, e.g. ietaksyaym,

p. aryloxypepokyl derivatives, e.g. fluazifop,

q. bipyridyl derivatives, e.g. paraquat, diquat,

pyridazinones, e.g. nortlurazop,

s. uracils, e.g. bromacil, terbacil,

t. isokiazolopes, e.g. clomazone,

u. Różner e.g. glnfo say olufosinac metazml, pacloPuSrazole, bzola ^ ten, desmedifbm, tenmnaifham, pyrazone, pyridate, amitrol, fluridone, DCPA, aitlapyr, propamia, bensulide, naprofamia, siduron, flumetsulam, methyl-clethhodim ethyl-tepakiaprop, methyl-haloxyfor, quisalophopiclobenil, isoxabenz, oxaaiazop, paclobutrazole, ethofumesate, quinclorac, aifenzoquat, entotall, phosphine, DSMA, MSMA,

v. group 11a other as described above,

v. group 11b others described above.

Particularly preferred partners from groups a) to w) are the herbicides of groups m) and v), i.e. iulfopyluria, triketones and dions. '

The co-use of a combination of almetepoamld and triketage (s) according to the invention is particularly suitable in blackberry crops such as cereals, maize and rice. However, it is most preferred to use weed corn in crops

176 082 monocotyledonous and dicotyledonous weeds, as the harmful effect on crops is not increased. It is possible to use this preferred combination before and after emergence of the undesirable weeds. However, the preferred application time in maize is after the maize seedlings have emerged.

The application rates for co-used dimethenamide and triketone or dione will of course depend on climatic conditions, season, soil ecology, weed control and the like, however, positive results may be obtained, e.g. with co-used triketone dosages which are significantly lower. than recommended for use on its own, e.g. 0.01 to 2 kg / ha, preferably 0.1 to 1 kg / ha, especially 0.1 to 0.6 kg / ha.

Combinations in which the triketone or the dione are selected from among this group are preferred

4- (4-chloro-2-nitrobenzoyl) -2,6,6-trimethyl-2H-1,2-oxazine-3,5- (4H, 6H) dionuisulcotrione, with sulcotrione being preferred.

The most preferred combination of this type is that of sulcotrione and dimethhenamide. The ratio of the mixture will be determined according to the specificity of the soil, the cultivation used and the climatic conditions. Exemplary rates of co-application would be the range of 0.9 to 1.5 kg / ha of dimethhenamide and 0.15 to 0.45 kg / ha of sulcotrione. The weight ratio of the active ingredient in the sulcotrione and dimethhenamide composition is between 1: 2 and 1:10.

Examples of individual mixing partners may be selected from the following: sulcotrione (e.g. MiKADO®) and 4- (4-chloro-2-nitrobenzoyl) -2,6,6-trimethyl-2H-1,2-oxazine 3,5- ( 4H, 6H) dione (Group VI compound).

According to the desired weed spectrum, time of application and the like, individual examples of suitable mixing partners are different, individual herbicides listed in groups a) to w).

Example I.

The active ingredients are weighed and dissolved in a stock solution consisting of acetone and deionized water, 1: 1 and 0.5% of a mixture of surfactants consisting of SPAN® 20: TWEEN® 20: TWENN® 85, 1: 1: 1 surfactants . Dilution with this stock solution was performed by allowing spray solutions to be prepared as single doses of the individual or combined active ingredients. Each dose was applied simultaneously with a linear track sprayer unit delivering 600 liters / ha of spray volume both to the foliage of the seedlings of the selected weed species for post-emergence application and to the surface of the soil previously seeded for pre-emergence application. Seedlings were grown until the plant had developed to the second or early third leaf stage. The development stage of each seedling was recorded at the time of application. After application, the treated plants are transferred to a greenhouse and kept until the end of the experiment within four weeks. Injury symptoms were recorded two and ten days after post-emergence application and fourteen days after pre-emergence application. A visual assessment of% crop damage and weed control was performed ten and twenty-eight days after pre-emergence application and fourteen and twenty-eight days after pre-emergence application.

Co-application of dimethhenamide with the other individual active ingredients indicated above results in improved herbicidal activity compared to the use of each active ingredient alone.

Example II.

Small plots of field maize infested with one-sided weed and black nightshade were dusted with a suspension of dimethhenamide and sulcotrione prepared in a tank. The weeds were in the full set single-sided weed stage and the 8-leaf black thrush stage. The plots were 8 meters long by 3 meters wide. The doses used were 1.1 kg / ha of dimethhenamide and 0.15 kg / ha of sulcotrione. Seven days after treatment, efficacy for both weed control and tolerance in the crop was assessed.

In the trial, the destruction of the weed was between 93 and 98% and the destruction of the nightshade between 91 and 93% in triplicate, while the damage to maize cultivation was always below 10%.

176 082

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Claims (9)

Patent claims A synergistic herbicide comprising the active ingredient, conventional adjuvants and an agriculturally acceptable carrier, characterized in that it comprises a herbicidally effective combined amount of dimethhenamide and another herbicide selected from the group of triketones and diones, including 2- (2-chloro-4-methane-) sulfonylbenzoyl) -1,3-cyclohexanedione; 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-2H1,2- oxazine-3,5 (4H, 6H) dione; 4- (4-methylthio-2-thiObenzoyl) -2,6,6-trimethyl-2H-1,2-oxazine-3,5- (4H, 6H) - dione; 3- (4-methyl-2-nitribenzoyl-bicyclo [3.2.1 ca.tano-2,4-dione; 4- (2-nitro-4-tril'luoromethoxybenzoyl) -2,6,6-trimethyl- 2H-1,2-oxazine-3,5 (4H, 6H) -dione, the weight ratio of the herbicide selected from the group of triketones and diones to dimethenamide is 1 :: 2-1: 10, and the active substances are present in the amount of 0, 01-90% by weight. 2. The agent according to claim The process of claim 1, comprising a combined amount of dimethyleneamide and another herbicide selected from the group of triketones and diones, including 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; S - 6 -methylsulfonyl-nitrobenzoyl) -bicyclo [3.2.1] octane-2,4-dione; 4t (4t - <^ 3c ^ i ^ c ^ - ^ 2 ^ -n ^: ^ t ^ and ^^ t ^^ nzooyl) -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-oxazine-3,5- (4H, 6H) -dione; 3- (4-methylthio-2-nitrobenzoyl) -bicyclo [3.2.1] octane-2,4-dione; 4- (2-nitr9-4-tril'luoromethoxybenzoyl) -2,6,6-trimethyl-2H-1,2-oxazine-3,5 (4H, 6H) -dione. 3. The agent according to claim A process as claimed in claim 1, characterized in that the active ingredients are sulcotrione and dimethhenamide. 4. A method for controlling undesirable vegetation, characterized in that a synergistic herbicide is applied to the sites of undesirable vegetation, characterized in that it comprises a herbicidally effective combined amount of dimethenamide and another herbicide selected from the group of triketones and diones, including 2- (2-chloro). -4-methanesulfonylbenzoyl) -1,3-cyclohexanedione; 2-44-nee ^ ^ k) sulkni ^ O ^ ^ ^ ^ ^ ^ ^ <^ <^ ^ ^ <^ ^ ^ ^ ^ <^ ^ nzoyl) -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. ^ octane2.4-dione; 4- (4-chloro-2-trobenzoyl) -2,6,6-trimethyl-2H-1,2-oxazine-3,5 (4] H 6H) dione; - (4-methylthio-2-nitrobenzoyl) -2,6,6-trimethyl-2H-1,2-oxazine-3,5- (4H, 6H) -dione; 3- (4-methyloyl-2-mtrobenzoyl) -bicyclo [3.2.1] cktane-2,4-dione; 4- (2-nitro-4-trifluoromethoxybenzoyl) -2,6,6-trimethyl-2H-1,2-oxazine-3,5- (4H, 6H) -dione, the weight ratio of the herbicide selected from the group of triketones and of diones to dimethhenamide is 1: 2-1: 10, and the active substances are present in the amount of 0.01-90% by weight, except that the dimethhenamide inside is used in the amount of 0.1-3.0 kg / ha the triketone inside is applied at a rate of 0.01-2.0 kg / ha. 5. The method according to p. The method of claim 4, wherein the synergistic herbicide is applied, characterized in that it comprises a herbicidally effective combined amount of dimethenamide and another herbicide selected from the group of triketones and dions, including 2- (4-methylsulfonyloxy-2-nitrobenzoyl) -4,4,6,6-tetramethyl-1,3-cyclohexanedione; 3- (4-meiylsulfonyloxy-2-nitrobenzoyl) -bicyclo [3.2.11-octane-2,4-dione; 3- (4-methylsulfonyl-2-nitrobenzoylph-bicycloS ©. 1] octane-2,4-dione; 4- (4-chloro-2-nitrobenzoyl) -2,6,6-ir "methyln-dl-1,2- ox &lt; yano-3.5-4H, 6H) dione; 4- (4-methylthi2-2-nitcobnnzollo - 2,6,6-ιrϊmethyl2H-1,2-oxazine-3,5- (4H, 6H) -dione; 3- (4-methylthio-2-nitrobenzoyl) - bicyclo [3.2.1] octane 2.4-dione; 4 ((2-nitro-4-trifluoromethoxybenzcilo) -2,6,6-trimethyl-2H-1,2-oxazine-3,5 (4H, 6H) -dione . 176 082 6. The method according to p. 4. The process of claim 4, characterized in that the agent is applied, characterized in that the active ingredients are dimethhenamide and sulcotrione, the dimethhenamide present in the center being used in an amount of 0.9-1.5 kg / ha and the sulcotrione present in the center being used in the amount of 0.15-0.45 kg / ha. 7. The method according to p. 4. The process as claimed in claim 4, characterized in that the dimethhenamide present in the center is applied in an amount of 0.1-2.0 kg / ha, in particular 0.25-1.5 kg / ha. 8. The method according to p. The method according to claim 5, characterized in that the dimethhenamide present in the center is applied in an amount of 0.1-2.0 kg / ha, in particular 0.25-1.5 kg / ha. 9. The method according to p. The method of claim 4, characterized in that the triketone present in the center is applied in an amount of 0.1-1.0 kg / ha, in particular 0.1-0.6 kg / ha.