MXPA99010358A - Herbicidal compositions - Google Patents

Abstract

Herbicidal compositions comprising:(a) at least one arylthiadiazolone having general formula (I);(b) one or more known herbicides. The above herbicidal compositions are useful for controlling weeds in agricultural crops.

Description

HERBICIDAL COMPOSITIONS DESCRIPTION OF THE INVENTION The present invention relates to herbicidal compositions. More specifically, the present invention relates to herbicidal compositions comprising at least one arylthiadiazolone and one or more known herbicides, and their use as herbicides to control weeds in agricultural crops. The applicant has in fact found that herbicidal compositions containing one or more known herbicides and at least one compound belonging to the group of 3-aryl-1,3,4-thiadiazole-2 (3H) -ones have a surprisingly high herbicidal activity towards numerous weeds but, at the same time, they are not phytotoxic with respect to important agricultural crops. Therefore, the present invention relates to herbicidal compositions comprising: (a) at least one arylthiadiazolone having the general formula (I): wherein: R represents an alkyl or haloalkyl group of linear or branched Ci-Cg; or a C3-C6 cycloalkyl or halocycloalkyl group; the alkyl or haloalkyl, cycloalkyl or halocycloalkyl groups are optionally substituted with linear or branched alkyl groups; X represents a halogen atom such as chlorine or fluorine; Y represents a halogen atom such as chlorine, fluorine, bromine or iodine; an alkyl or haloalkyl group of linear or branched Cx-C4; a linear or branched C1-C4 alkoxy or haloalkoxy group; - Rx represents a hydrogen atom or a methyl group; (b) one or more herbicides that are selected from the following: chloramben, chlortal, dicamba, naptalam, 2,3,6-TBA, clopyralide, difluofenzopyr (SAN 835 H); dithiopyr, picloram, thiazopir (MO? 13200), quinclora, quinmerac, indanofan (MK-243), benazoline, chlorflurenol, dalapon, endotal, flamprop, flamprop M, flupropanate, flurenol, TCA-sodium, bromobutide, chlortiamide, diflufenican, diphenamide , etabenzanide (HW 52), isoxaben, mefenacet, monalide, pentanochlor, propanil, propizamide, 5 tebutam, flutiamide (BAY FOE 5043), clodinafop, clomeprop, cyalofop-butyl (XDE-537), 2,4-D, 2, 4-DB, dichlorprop, dichlorprop-P, diclofop, fenoxaprop, fenoxaprop-P, fluazifop, fluazifop-P, fluroxypir, haloxifop, haloxifop-P-methyl, isoxapirifop, MCPA, MCPA-thioethyl, MCPB, mecoprop, mecoprop-P, naproanilide, napropamide, propaquizafop, quizalofop, quizalofop-P, triclopyr, UBI-C4874, bromophenoxy, bromoxynil, diclobenil, yoxinil, dicuat, paraquat, asulam, butylate, carbetamide, chlorbufam, chlorprofam, cycloate, desmedipham, dimepiperate, EPTC, esprocarb , molinate, orbencarb, pebulate, fenmedifam, profam, prosulfocarb, pyributicarb, thiobencarb, thiocarbazil, tri-alato, vernolate, alloxydim, butroxydim, clethodim, cycloxydim, sethoxydim, sulcotrione, tralcoxydim, acetochlor, alachlor, butachlor, butenachlor, dietyl, dimethachlor, dimethenamid, metazachlor, metolachlor, pretilachlor, propachlor , propisoclor, tenilchlor (NSK-20 850), acifluorfen, aclonifen, bifenox, clometoxifen, clornitrofen, atoxifen-etil (HC-252), fluoroglycofen, fluoronitrofen, fomesafen, furiloxifen, lactofen, AKH-7088, oxyfluorfen, benfluralin, butralin, dinitramid, etalfluoralin, flucloralin, isopropalin, orizalin, pendimethalin, prodiamine, trifluralin, dinoseb, dinoseb acetate, dinoterb, amitrol, benfuresate, bentazone, benzophenap, cafenstrol (CH-900), carfentrazone-ethyl (F-8426), chloridazon, cinmatilin, clomazone, difenzoquat, etofumesato, pyraflufen-ethyl (ET- 751), flumiclora- pentyl, flumioxazin, flumipropin, flupoxam, fluridone, 5 fluorochloridone, flurtamone, flutiacet methyl (KIH-9201), isoxaflutone (RPA 201772), metazole, nipiraclofen, norflurazon, oxadiargil, oxadiazon, oxaziclomefona (MY-100) , pentoxazone (KPP-314), pyrazolinate, pyrazoxifen, pyridate, sulfentrazone (F6285), thidiazimin, anilofos, bensulide, bilanafos, butamifos, fosamina, glufosinate, glyphosate, LS830556, piperophos, azametabenz, imazemetipir (AC-263, 222), imazamox (AC-299, 263), imazapir, imazaquin, imazetapir, bispirabac-sodium (KHI-2023), piribenzoxim (LGC-40863), piriminobac-methyl (KIH-6127), piritiobac-sodium (KIH- 2031), thiochlorim, cloransulam-methyl (XDE-565), diclosulam (XDE-15 564), flumetsulam (DE-498), metosulam (DE-511), amidosulfuron, azimsulfuron (DPX-A8947), bensulfuron, chlorimuron, chlorsulfan, cinosulfuron, cyclosulfamuron (AC-322, 140), metsulfuron-methyl (DPX-A7881), ethoxysulfuron (HOE 095404), flazasulfuron, flupirasulfuron (DPX-KE459), halosulfuron (NC-319), imazosulfuron, metsulfuron, NC-330, nicosulfuron, oxasulfuron (CGA-277476), primisulfuron, prosulfuron (CGA-152005), pyrosulfuron, rimsulfuron, sulfometuron (DPX-5648), sulfosulfuron (MON-37500), thifensulfuron, triasulfuron (CGA-131036), tribenuron, triflusulfuron-methyl (DPX- 66037), ametrin, atrazine, azipothrine, cyanazine, desmethrin, dimetham-trin, dipropetrin, eglinazine, metoprotrin, proglinazine, prometon, prometryn, propazine, simazine, symmetry, terbumeton, terbutilazine, terbutrin, triaziflam (IDH-1105), trietazine, SMY-1500, hexazinone, metamitron, metribuzin, bromacil, lenacil, terbacil, benzthiazuron, chlorbromuron, chloroxuron, chlorotoluron, cumiluron (JC-940), daimuron, diphenoxuron, dimefuron, 1-diuron, etidimuron, fenuron, fluometuron, isoproturon, isouron, linuron, metabenzthiazuron , metildimron, methobenzuron, metobromuron, methoxuron, monolinuron, neburon, siduron, tebutiuron, thiazafluron, isopropazole (JV 485), KPP 300, KPP 421, BAY YRL 2388, DPXT 5975, azaphenidin. Specific examples of arylthiadiazolones having the general formula (I) which can be used for the purposes of the present invention are: 3- [2,4-dichloro-5- (2-propynyloxy) phenyl] -5- ( 1,1-dimethylethyl) -1,3,4-thiadiazol-2 (3H) -one (Compound No. 1); 3- [4-chloro-2-fluoro-5- (2-propynyloxy) phenyl] -5- (1,1-dimethylethyl) -1,4,4-thiadiazol-2 (3H) -one (Compound No. 2 ); 5-cyclopropyl-3- [2,4-dichloro-5- (2-propynyloxy) phenyl] -1,4,4-thiadiazol-2 (3H) -one (Compound No. 3); 5-cyclopropyl-3- [4-chloro-2-fluoro-5- (2-propynyloxy) phenyl] -1,4,4-thiadiazol-2 (3H) -one (Compound No. 4); 3- [2,4-dichloro-5- (2-propynyloxy) phenyl] -5- (1-methylethyl) -1,3,4-thiadiazol-2 (3H) -one (Compound No. 5); 3- [4-chloro-2-fluoro-5- (2-propynyloxy) phenyl] -5- (1-methylethyl) -1,4,4-thiadiazol-2 (3H) -one (Compound No. 6); 3- [2,4-dichloro-5- (2-propynyloxy) phenyl] -5-ethyl-1,3,4-thiadiazol-2 (3H) -one (Compound No. 7); 3- [4-chloro-2-f-luoro-5- (2-propynyloxy) f-enyl] -5-ethyl-1,3,4-thiadiazol-2 (3H) -one (Compound No. 8); 3- [2,4-dichloro-5- (2-propynyloxy) phenyl] -5- (1-methylcyclopropyl) -1,3-thiadiazol-2 (3 H) -one (Compound No. 9); 3- [4-chloro-2-f-luoro-5- (2-propynyloxy) phenyl] -5- (1-methylcyclopropyl) -1,4,4-thiadiazol-2 (3H) -one (Compound No. 10); (±) -3- [2,4-Dichlorophenyl-5- (1-methyl-2-propynyloxy) phenyl] -5- (1, 1-dimethylethyl) -1,3,4-thiadiazole-2 (3H) - ona (Compound No. ll); (±) -3- [4-Chloro-2-fluoro-5- (1-methyl-2-propynyloxy) phenyl] -5- (1, 1-dimethylethyl) -1,3,4-thiadiazole-2 (3H ) -one (Compound No. 12); (±) -5-Cyclopropyl-3- [2, -dichloro-5- (1-methyl-2-propynyloxy) phenyl] -1,4,4-thiadiazol-2 (3H) -one (Compound No. 13); (±) -5-Cyclopropyl-3- [4-chloro-2-f-luoro-5- (1-methyl-2-propynyloxy) phenyl] -1,3-thiadiazol-2 (3H) -one (Compound No 14); (±) -3- [2,4-Dichloro-5- (l-methyl-2-propynyloxy) phenyl] -5- (1-methylethyl) -1,4,4-thiadiazol-2 (3H) -one ( Compound No. 15); (±) -3- [4-Chloro-2-fluoro-5- (1-methyl-2-propynyloxy) phenyl] -5- (1-methylethyl) -l, 3,4-thiadiazole-2 (3H) - ona (Compound No. 16); (±) -3- [2,4-dichloro-S- (l-methyl-2-propynyloxy) phenyl] -5-ethyl-l, 3,4-thiadiazol-2 (3 H) -one (Compound No. 17 ); (±) -3- [4-chloro-2-fluoro-5- (l-methyl-2-propynyloxy) phenyl] -5-ethyl-l, 3,4-thiadiazol-2 (3H) -one (Compound No 18); - (+) - 3 - [2,4-dichloro-5- (l-methyl-2-propynyloxy) phenyl] -5- (1-methylcyclopropyl) -1,3,4-thiadiazole-2 (3H) -one (Compound No. 19); (±) -3- [4-Chloro-2-fluoro-5- (1-methyl-2-propynyloxy) phenyl] -5- (1-methylcyclopropyl) -1,3,4-thiadiazole-2 (3H) - ona (Compound No. 20). The arylthiadiazolones having the general formula (I) can be conveniently prepared by means of various processes. A process for the preparation of the arithiadiazolones having the general formula (I) comprises the reaction of a thiohydrazide having the general formula (II): wherein X, Y, R and Rx have the meanings described above, with phosgene, trichloromethyl chloroformate or bis (trichloromethyl) carbonate, in the presence of, or without, preferably in the presence of an inert organic solvent, at a temperature ranging from +20 ° C to the boiling temperature of the mixture itself, optionally in the presence of an organic or inorganic base. Inert organic solvents which can be used for this purpose are chlorinated hydrocarbons such as, for example, methylene chloride, chloroform, 1,2-dichloroethane, etc.; aromatic hydrocarbons such as, for example, benzene, toluene, xylene, chlorobenzene, etc .; ethers such as, for example, ethyl ether, tetrahydrofuran, dimethoxyethane, dioxane, etc .; esters such as, for example, ethyl acetate, etc.

The organic bases which can be used for this purpose are, for example, triethylamine, pyridine, 4-dimethylaminopyridine, etc. The inorganic bases which can be used for this purpose are, for example, sodium bicarbonate, etc. The thiohydrazides having the general formula (II) can be prepared by treatment of the corresponding hydrazides with phosphorus pentasulfide or with the reagent Lawesson as described, for example, in "Journal of Fluorine Chemistry" (1978), Vol. 2, pages 1-21, or in "Chemistry Express" (1991), Vol. 6, pages 411-414. The herbicides (b) are all products which are known in the art and are commercially available. The herbicides (b) included above are indicated by their common name or code number as specified, for example, in "The Agrochemicals Handbook (1994)", third edition, Royal Society of Chemistry; or in "AG Chem New Compund Review", Vol. 13 (1995), Vol. 14 (1996) and Vol. 15 (1997), W. L. Hopkins, AG Chem Information Service; or in "Brighton Crop Protection Conference-Proceedings", (1991), (1993) and (1995). The use of the herbicidal compositions of the present invention has proven to be advantageous with respect to the use of the known herbicides (b) included above, by themselves, wherein the presence of at least one arylthiadiazolone having the general formula (I) allows the use of reduced doses of these herbicides which are often phytotoxic and / or extend the spectrum of action. The herbicidal compositions of the present invention have been shown to be particularly effective both in the pre-germination and post-germination treatment, in the control of various weeds, both monocotyledonous and dicotyledonous. At the same time, these herbicidal compositions have shown little or no phytotoxicity towards important agricultural crops, which makes it possible for them to be used in the agricultural field in the selective control of weeds. Examples of weeds which can be effectively controlled with the herbicidal compositions of the present invention are: Abutilon theofrasti. Alisma plantago. Alopecurus mvosuroides, Amaranthus spp. , Ambrosia artemisifolia, Amnimaius, Apera spica venti. Avena fatua. Bromus spp .. Capsella bursa pastoris, Cassia obtusifolia. Chenopodium album, Convolvulus sepium. Cyperus spp .. Datura stramonium. Digitaria sanguinalis, Echinochloa spp. Eleusine indica, Galium aperine. Geranium dissectum, Heleocharis avicularis. Heteranthera spp .. Ipomea spp. , Lolium spp. Matricaria spp. Monochoria vaginalis, Panicum spp. , Papaver rhoaes. Phaseolus aureus, Poa spp. , Polycfonum spp. , Portulaca olerácea. Rotala indica, Sagittaria pigmaea, Scirpus spp. , Sesbania exaltata. Setaria viridis. AIDS spinosa. Sorgum spp. , Solanum nigrum, Stellaria media. Veronica spp. , Vicia fabae, Viola arvensis, Xanthium spp. , etc. The doses used for agricultural applications, the herbicidal compositions of the present invention have no toxic effects with respect to one or more agriculturally important crops such as, for example, corn (Zea mais), wheat (Triticum spp.), Soybean (Glicine max. ), rice (Oryza sativa), etc. Arylthiadiazolones having the general formula (I) and the herbicides (b) included above, which form the above herbicidal compositions, can be combined in any proportion, depending on various factors such as, for example, the number and type of constituents of the mixture, the planting that will be protected, the weeds that are going to be eliminated, the degree of infestation, the method of application, the characteristics of the soil, etc. In the herbicidal compositions of the present invention, the amount by weight of the arylthiadiazolone having the general formula (I) can generally vary from 1 g / ha to 5 kg / ha, preferably from 10 g / ha to 500 g / ha. In the herbicidal compositions of the present invention, the ratio between the amount by weight of the arylthiadiazolone having the general formula (I) and the amount by weight of the product or products with herbicidal activity (b) included above, can generally vary from 99.9. : 0.1 to 0.1: 99.9, preferably from 99: 1 to 1:99.

In the case of pre-germination treatment in corn, cereal or soybean crops, the herbicidal compositions of the present invention comprise, in addition to the arylthiadiazolone having the general formula (I), one or more of the following herbicides (b) to be selected from those included before, based on the planting in question and the weeds to be eliminated: acetochlor, acifluorfen, aclonifen, alachlor, ametrin, atrazine, bifenox, butralin, chloramben, clomazone, chlorbromuron, chlorotoluron, chlorsulfuron, cyanazine, cyclosulfamuron (AC-322, 140), dietyl, diflufenican, dimethenamid, diphenamid, eglinazine, flucloralin, flumioxazin, fluoroglyco- phen, flupoxam, flurocloridone, flurtamone, halosulfuron (NC-319), imazaquin, imazetapyr, isoproturon, isoxaben, isoxaflutol ( RPA 201772), linuron, metazachlor, metabenzthiazuron, metobromuron, metolachlor, methoxuron, metribuzin, metsulfuron, monolinuron, norflurazon, orbencarb, oxadiazon, oxyfluorfen, pendimethalin, prog linazine, propachlor, prosulfocarb, SMY1500, sulfentrazone, terbutrin, flutiamide (BAY FOE 5043), tri-alato, triasulfuron, trifluralin. In the case of treatment of rice crops, the herbicidal compositions of the present invention comprise, in addition to the arylthiadiazolone having the general formula (I), one or more of the following herbicides (b), which are selected from those included above , based on the method of use and the weeds to be eliminated: acifluorfen, anilofos, azimulsufuron (DPX-A8947), bensulfuron, bensulide, benzofenap, bifenox, bispyribac-sodium (KHI-2023), bromobutide, butachlor, butenachlor , butralin, cafenstrol (CH-900), clometoxifen, clornitrofen, chlorprofam, cinmetilin, cinosulfuron, clomeprop, cumiluron, cyclosulfamuron (AC-322, 140), daimuron, diclobenil, dietyl, dimethoperate, dimethamethrin, esprocarb, ethoxysulfuron (HOE 095404) , flucloralin, halosulfuron (NC-319), mefenacet, metildimiron, molinate, naproanilide, oxadiargil, oxadiazon, oxaziciclomefona (MY-100), pentoxazone, piperofos, pretilaclor, propanil, pyrazolinate, pirazosulfuron, pirazoxifen, piribenzoxim (LGC-40863 ), piributicarb, piriminobac-methyl (KIH-6127), quinclorac, symmetry, tenylchlor (NSK-850), thiobencarb, thiocarbazil. For practical use in agriculture, it is often advantageous to use the herbicidal compositions of the present invention in the form of suitable formulations. This can be obtained either by formulating an arylthiadiazolone having the general formula (I) with one or more herbicides (b) which are selected from those listed above, to provide the desired composition, or to form the composition at the time of use. by mixing suitable amounts of an arylthiadiazolone having the general formula (I) with one or more herbicides that are selected from those included above, formulated separately. The compositions can be used in the form of dry powders, wettable powders, emulsifiable concentrates, emulsions, microemulsions, suspoemulsions, gels, pastes, flakes, solutions, suspensions, granules, tablets, films, etc .: the selection of the type of composition depends on the specific use. The compositions are prepared according to known methods, for example, by diluting or dissolving the active substance or substances with a solvent medium and / or with a solid diluent, optionally in the presence of surfactants. The liquid diluents which can be used, in addition to water in a natural way, exist several solvents such as, for example, N, N-dimethylformamide; dimethyl sulfoxide; N-alkylpyrrolidones (N-methylpyrrolidone, etc.); aliphatic hydrocarbons (hexane, cyclohexane, etc.); aromatic hydrocarbons (xylols, mixtures of alkylbenzoles, alkylnaphthalenes, etc.); chloroaromatics (chlorobenzole); alcohols (methanol, propanol, butanol, octanol, cyclohexanol, decanol, tetrahydrofurfuryl alcohol, etc.); glycols (ethylene glycol, propylene glycol, etc.); ketones (acetone, cyclohexanone, 2-heptanone, acetophenone, isophorone, 4-hydroxy-4-methyl-2-pentanone, etc.); esters (isobutyl acetate, etc.); vegetable or mineral oils; or its mixtures. Solid inert diluents, or carriers, which can be used are kaolin, alumina, attapulgite, bentonite, kaolin, montmorillonite, calcite, dolomite, clay, pumice, quartz, sand, silica, talc, sepiolite, diatomaceous earth, starch , cellulose, sugars, urea, calcium carbonate, sodium carbonate, sodium bicarbonate, sodium sulfate, etc. The surfactants which may be used are emulsifying and wetting agents of the non-ionic type such as, for example, polyethoxylated aliphatic and cycloaliphatic alcohols, polyethoxylated alkylphenols, polyethoxylated sorbitan fatty acid esters, water-soluble polyethylene polyethylene oxide with polypropylene glycols or ethylene diaminopropylene glycols, or with alkyl polypropylene glycols, etc .; of the anionic type such as, for example, metal or ammonium salts of C 10 -C 22 fatty acids or of alkylarylsulfonates or of alkylsulfonates or of alkyl sulfates, benzimidazole sulfonate derivatives, etc .; of the cationic type, such as, for example, C8-C22 alkylammonium quaternary salts, etc. The above compositions may also contain dispersing agents (for example lignin and its salts, cellulose derivatives, alginates, etc.), stabilizers (for example antioxidants, UV-absorbing substances, etc.), anti-foaming agents (for example, silicone, etc.), thickeners. If desired, it is possible to add other compatible active principles to the herbicidal compositions of the present invention, such as, for example, other herbicides, fungicides, phytoregulators, antibiotics, insecticides and fertilizers.

The herbicidal compositions of the present invention usually contain from 0.1% to 99% by weight, preferably from 1% to 95% by weight, of a combination of an arylthiadiazolone having the general formula (I) with one or more herbicides ( b) which are selected from above, from 1% to 99.9% by weight of a liquid or solid diluent, and from 0% to 25% by weight, preferably from 0.1% to 20% by weight of a surfactant . The following examples are illustrative only and do not limit the scope of the present invention.

EXAMPLE 1 Preparation of 3- [2, 4-dichloro-5- (2-propynyloxy) phenyl] -5- (1,1-dimethylethyl) -1,3, -thiadiazol-2 (3H) -one (Compound No. 1) 0.5 g (2.5 mmol) of trichloromethyl chloroformate are added to a solution of 1.65 g (5 mmol) of N '- [2,4-dichloro-5- (2-propynyloxy) phenyl] -N-thiopivaloyl-hydrazine in 25 g. ml of dioxane and kept in a nitrogen atmosphere. The mixture obtained in this way is kept under stirring, at room temperature, for 3 hours. The mixture is then poured into water (250 ml) and extracted with ethyl ether (3 x ml). The organic phase obtained is washed until it becomes neutral, with a saturated solution of sodium chloride, the water is extracted with sodium sulphate and concentrated by means of a rotary evaporator. The raw material obtained in this way is purified by means of a rotary evaporator. chromatography on silica gel eluting with n-hexane / ethyl acetate in a ratio of 9: 1. 1.4 g of a solid product having a melting point of 92 ° C, corresponding to Compound No. 1.

EXAMPLE 2 Using the same procedure described in Example 1, the following compounds are prepared: 3- [4-chloro-2-f-luoro-5- (2-propynyloxy) phenyl] -5- (1,1-dimethylethyl) -1, 3,4-thiadiazole-2 (3H) -one (Compound No. 2; mp 73 ° C-74 ° C); 5- cyclopropyl -3- [2,4-dichloro-5- (2-propynyloxy) -phenyl] -1,4,4-thiadiazole-2 (3H) -one (Compound No. 3, mp 99 ° C-101 ° C); 5-cyclopropyl-3- [4-chloro-2-fluoro-5- (2-propynyloxy) phenyl] -1,4,4-thiadiazol-2 (3H) -one (Compound No. 4, dense oil); 3- [2,4-di-chloro-5- (2-propynyloxy) phenyl] -5- (1-methylethyl) -1,4,4-thiadiazol-2 (3H) -one (Compound No.5; ° C-57 ° C); 3- [4-chloro-2-fluoro-5- (2-propynyloxy) phenyl] -5- (1-methylethyl) -1,4,4-thiadiazol-2 (3H) -one (Compound No. 6; dense); 3- [2, 4-dichloro-5- (2-propynyloxy) phenyl] -5-ethyl-l, 3,4-thiadiazol-2 (3H) -one (Compound No. 7; mp 100 ° C-101 ° C; 3- [4-chloro-2-fluoro-5- (2-propynyloxy) phenyl] -5-ethyl-l, 3,4-thiadiazol-2 (3H) -one (Compound No. 8; mp 93 ° C-94 ° C); 3- [2,4-dichloro-5- (2-propynyloxy) phenyl] -5- (1-methylcyclopropyl) -1,3,4-thiadiazol-2 (3H) -one (Compound No. 9; mp 117 ° C-119 ° C); 3- [4-chloro-2-fluoro-5- (2-propynyloxy) phenyl] -5- (1-methylcyclopropyl) -1,4,4-thiadiazole -2 (3H) -one (Compound No. 10; mp 95 ° C-97 ° C).

EXAMPLE 3 Determination of herbicidal activity prior to germination The herbicidal activity and the phytotoxicity of the compositions of the present invention are evaluated in a pre-germination treatment, according to the following operating procedures. Pots are prepared (10 cm in diameter, 10 cm in height) containing sandy soil. In each of them a weed or crop is sown.

The pots are divided into four groups, each containing 5 pots for each weed and harvest. Twenty-four hours after sowing, the pots are soaked with a light watering. One hour after soaking, the first group of pots is treated with a hydroacetone dispersion containing the composition under evaluation, acetone (10% by volume) and Tween 20 (0.5%). The second group of pots is treated with a hydroacetone dispersion containing the amount of arylthiadiazolone used in the composition, acetone (10% by volume) and Tween 20 (0.5%). The third group of pots is treated with a hydroacetone dispersion containing the amount of known herbicide used in the composition, acetone (10% by volume) and Tween 20 (0.5%). The fourth group of pots is treated with a hydroacetone solution containing acetone (10% by volume) and Tween 20 (0.5%), and used as a comparison (control). After the treatment, all the pots are moistened uniformly every two days and kept in a conditioned environment under the following conditions: temperature: 24 ° C; relative humidity: 60%; Lighting period: 16 hours; - luminous intensity: 10000 lux.

Twenty-eight days after the treatment, the herbicidal activity and the phytotoxity of the composition are determined in comparison with that of the components alone and the control. In Table 1 below, the composition of arylthiadiazolones of the general formula I (1st component) with known herbicides (2nd component) for which improved herbicidal activity and / or reduced phytotoxicity has been observed with respect to the effect is presented, divided by crops. Additive of single components.

TABLE 1 Harvest Compound No. Known herbicide (1st component) (2nd component) Corn 1 * acetochlor; aclonifen; alachlor ametrin atrazine; BAY FOE 5043; benfuresate bifenox; butylate; clomazone; cyanazine dietylethyl; dimethenamid; EPTC etalfluralon; flumetsulam halosul furonme t ilo; indanofan isoxaflutole; lunoron, - metabenzthiazuron methobromuron; metolachlor; metosulam monolinuron; orbencarb; oxyfluorfen pendimethalin; propachlor; terbuthylazine - trialate - vernolate Wheat / barley aclonifen; BAY FOE 5043, bifenox; ciclosul f amuron; Clorsulfuron; clortoluron; diflufenican; ethoxysulfuron,, fluoroglycofen; flupoxam; flurtamone, - indanofan; isopropazole; isoproturon; isoxaben; KPP 300; KPP 421; linuron; metabenzthiazuron; methoxuron; MON 375-00; monolinuron; neburon; orbencarb; oxyfluorfen; pendimetalin; prosulfocarb; siduron, - trialate; trifluralin; UCC 4243; Anilofos rice; phentrazamide (BAY YRC 2388); BAY FOE 5043; benfuresate; bifenox; cafenstrol; clometoxifen; clornitrofen; chlorprofam, - cinmethilin; cyclosulfamuron; daimuron; dimethoperate; dimethamethrin, - esprocarb; etabenzanid; ethoxysulfuron; fluoroglyphon; indanofan; mefenacet; molinate; Oxadiargyl; oxadiazon; oxaziclomene, - pentoxazone; piperophos; pretilachlor; pyrazolinate; pirazoxifen; pyributicarb; pyrazosulfuron ethyl; quinclorac; symmetry; thiobencarb; thiocarbazil; Soybean l1 BAY FOE 5043; bifenox; Chlorbromuron Chlorimuron; chlorprofam; clortal clomazone; dimethenamid; etalfluralin flumetsulam; flumioxazin, - fluoroglycofen fomesafen; imazaquin; imazethapyr indanofan; linoron; metolachlor; naptalam norflurazon; orbencarb; orizalin oxyfluorfen; propachlor; sulfentrazone thiazopyr; trifluralin; vernolate, - Cotton chlorprofam; chlortal; dimefuron; DPXT 5975; etalfluralin; fluometuron; indanofan; linuron; metolachlor; norflurazon; orbencarb; orizalin; oxyfluorfen; prometrin; propachlor; thiazopyr; Sunflower aclonifen; chlorbromuron; chlorprofam; etalfluralin; flurocloridone; flurtamone; linuron; metolachlor; trialate; Sugarcane 1 * acetochlor; bromacil; cyanazine dime ametrin; ethoxysulfuron; fluometuron isoxaflutole; linuron; metolachlor oxadiargyl; propachlor; sulfentrazone tebutiuron; terbacil; thiazopyr.

* Compound described in Example 1

Claims (11)

1. CLAIMS 1. Herbicidal compositions, comprising: (a) at least one arylthiadiazolone having the general formula (I): wherein: R represents a straight or branched C1-C6 alkyl or haloalkyl group; or a C3-C6 cycloalkyl or halocycloalkyl group; the alkyl or haloalkyl, cycloalkyl or halocycloalkyl groups are optionally substituted with linear or branched alkyl groups; X represents a halogen atom such as chlorine or fluorine; - Y represents a halogen atom such as chlorine, fluorine, bromine or iodine; an alkyl or haloalkyl group of linear or branched Cx-C4; a linear or branched Cx-C4 alkoxy or haloalkoxy group; Rj. represents a hydrogen atom or a methyl group; (b) one or more herbicides that are selected from the following: chloramben, chlortal, dicamba, naphthalam, 2,3,6-TBA, clopyralide, diflufenzopyr (SAN 835 H); dithiopyr, picloram, thiazopir (MON 13200), quinclora, quinmerac, indanofan (MK-243), benazoline, chlorflurenol, dalapon, endotal, flamprop, flamprop M, flupropanate, flurenol, TCA-sodium, bromobutide, chlortiamide, diflufenican, diphenamide, etabenzanida (HW 52), isoxaben, mefenacet, monalide, pentanochlor, propanil, propyzamide, tebutam, fluthiamide (BAY FOE 5043), clodinafop, clomeprop, cyalofop-butyl (XDE-537), 2,4-D, 2,4- DB, dichlorprop-P, diclofop, fenoxaprop, fenoxaprop-P, fluazifop, fluazifop-P, fluroxypyr, haloxyfop, haloxyfop-P-methyl, isoxapyrifop, MCPA, MCAP-thioethyl, MCPB, mecoprop, mecoprop-P, naproanilide, napropamide, propaquizafop, quizalofop, quizalofop-P, triclopyr, UBI-C4874, bromophenoxy, bromoxynil, diclobenil, yoxinil, dicuat, paraquat, asulam, butylate, carbetamide, chlorbufam, chlorprofam, cycloate, desmedipham, dimepiperate, EPTC, esprocarb, molinate, orbencarb, pebulate, fenmedifam, prfam, prosulfocarb, pyributicarb, thiobencarb, thiocarbazil, tri-alato, ve rnolato, alloxydim, butroxydim, clethodim, cycloxydim, sethoxydim, sulcotrione, tralkoxydim, acetochlor, alachlor, butachlor, butenachlor, diethatyl, dimethachlor, dimethenamid, metazachlor, metolachlor, pretilachlor, propachlor, propisochlor, thenylchlor (NSK-850), acifluorfen, aclonifen , bifenox, clometoxifen, clornitrofen, atoxifen-etil (HC-252), fluoroglycofen, fluoronitrofen, fomesafen, furiloxifen, lactofen, AKH-7088, oxyfluorfen, benfluralin, butralin, dinitramid, etalfluoralin, flucloralin, isopropalin, orizalin, pendimethalin, prodiamine, trifluralin, dinoseb, dinoseb acetate, dinoterb, amitrole, benfuresate, bentazone, benzofenap, cafenstrole (CH-900), carfentrazone-ethyl (F-8426), chloridazon, cinmatilin, clomazone, difenzoquat, ethofumesate, pyraflufen-ethyl (ET-751 ), flumiclora-pentyl, flumioxazin, flumipropin, flupoxam, fluridone, fluorochloridone, flurtamone, flutiacet methyl (KIH-9201), isoxaflutone (RPA 201772), metazole, nipiraclofen, norflurazon, oxadiargyl, oxadiazon, oxaziclomefone (M Y-100), pentoxazone (KPP-314), pyrazolinate, pyrazoxifen, pyridate, sulfentrazone (F6285), thidiazimin, anilophos, bensulide, bilanafos, butamiphos, fosaminate, glufosinate, glyphosate, LS830556, piperophos, imazametabenz, imazemetipir (AC-263) , 222), imazamox (AC-299, 263), imazapyr, imazaquin, imazethapyr, bispirabac-sodium (KHI-2023), pyribenzoxim (LGC-40863), pyriminobac-methyl (KIH-6127), pyrithiobac-sodium (KIH- 2031), tioclorim, cloransulam-methyl (XDE-565), diclosulam (XDE-564), flumetsulam (DE-498), metosulam (DE-511), amidosulfuron, azimsulfuron (DPX-A8947), bensulfuron, chlorimuron, clorsulfaron, cyclosulfuron, cyclosulfamuron (AC-322, 140), eta-metsulfuron-methyl (DPX-A7881), ethoxysulfuron (HOE 095404), flazasulfuron, flupirasulfuron (DPX-KE459), halosulfuron (NC-319), imizosulfuron, metsulfuron, NC- 300, nicosulfuron, oxasulfuron (CGA-277476), primisulfuron, prosulfuron (CGA-152005), pyrosulfuron, rimsulfuron, sulfometuron (DPX-5648), sulfosulfuron (MON-37500), fensulfuron, triasulfuron (CGA-131036), tribenuron, triflusulfuron-methyl (DPX-66037), ametryn, atrazine, azyprotrine, cyanazine, desmethrin, dimetham-trin, 5 dipropetrin, eglinazine, metoproprine, proglinazine, prometon, prometryn, propazine, simazine , simetryn, terbumeton, terbuthylazine, terbutryn, triaziflam (IDH-1105), trietazine, SMY- 1500, hexazinone, metamitron, metribuzin, bromacil, lenacil, terbacil, benzthiazuron, chlorbromuron, chloroxuron, chlorotoluron, 10 cumiluron (JC-940), daimuron, difenoxuron, dimefuron, 1-diuron, etidimuron, fenuron, fluometuron, isoproturon, isouron, linuron, metabenzthiazuron, metildimron, metobenzuron, metobromuron, methoxuron, monolinuron, neburon, siduron, tebutiuron, thiazafluron, isopropazole (JV 485), KPP 300, KPP 421, BAY YRL 15 2388, DPXT 5975, azafenidin.
2. 2. The herbicidal compositions, as described in claim 1, wherein the arylthiadiazolone having the general formula (I) are: 20 -3- [2,4-dichloro-5- (2-propynyloxy) phenyl] -5- ( 1, 1- dimethylethyl) -1,3,4-thiadiazol-2 (3H) -one; 3- [4-chloro-2-fluoro-5- (2-propynyloxy) phenyl] -5- (1,1-dimethylethyl) -1,4,4-thiadiazol-2 (3H) -one; 5-cyclopropyl-3- [2,4-dichloro-5- (2 -25 propynyloxy) phenyl] -1,3,4-thiadiazol-2 (3 H) -one; 5-cyclopropyl-3- [4-chloro-2-fluoro-5- (2-propynyloxy) phenyl] -1,3,4-thiadiazol-2 (3H) -one; 3- [2,4-dichloro-5- (2-propynyloxy) phenyl] -5- (1-methylethyl) -1,3,4-thiadiazol-2 (3H) -one; 3- [4-chloro-2-fluoro-5- (2-propynyloxy) phenyl] -5- (1-methylethyl) -1,3,4-thiadiazol-2 (3H) -one; 3- [2, 4 -di chloro-5- (2-propynyloxy) phenyl] -5-ethyl-1,3,4-thiadiazol-2 (3H) -one; 3- [4-chloro-2-f-luoro-5- (2-propynyloxy) phenyl] -5-ethyl-1,3,4-thiadiazol-2 (3H) -one; 3- [2,4-dichloro-5- (2-propynyloxy) phenyl] -5- (1-methylcyclopropyl) -1,3,4-thiadiazol-2 (3 H) -one; 3- [4-chloro-2-fluoro-5- (2-propynyloxy) phenyl] -5- (1-methylcyclopropyl) -1,3,4-thiadiazol-2 (3H) -one; - (±) - 3 - [2, 4-di-chloroform-5 - (1-methyl-2-propynyloxy) phenyl] -5- (1,1-dimethylethyl) -1,4,4-thiadiazole -2 (3H) -one; (±) -3- [4-Chloro-2-fluoro-5- (1-methyl-2-propynyloxy) phenyl] -5- (1, 1-dimethylethyl) -1, 3, 4-thiadiazole-2 (3H ) -one; (±) -5-cyclopropyl-3- [2, 4-di chloro-5- (l-methyl-2-propynyloxy) phenyl] -1,3,4-thiadiazol-2 (3 H) -one; (±) -5-Cyclopropyl-3- [4-chloro-2-f-luoro-5- (1-methyl-2-propynyloxy) phenyl] -1,3,4-thiadiazol-2 (3H) -one; (±) -3 - [2,4-dichloro-5- (l-methyl-2-propynyloxy) phenyl] -5- (1-methylethyl) -1,3,4-thiadiazol-2 (3 H) -one; (±) -3- [4-Chloro-2-fluoro-5- (1-methyl-2-propynyloxy) phenyl] -5- (1-methylethyl) -1,3,4-thiadiazole-2 (3H) - ona; (±) -3- [2,4-dichloro-5- (1-methyl-2-propynyloxy) phenyl] -5-ethyl-1,3,4-thiadiazol-2 (3H) -one; - (±) - 3 - [4-Chloro-2-f-loro-5- (1-methyl-2-propynyloxy) phenyl] -5-ethyl-1,3,4-thiadiazole-2 (3H) -one; (±) -3- [2,4-dichloro-5- (l-methyl-2-propynyloxy) phenyl] -5- (1-methylcyclopropyl) -1,3,4-thiadiazol-2 (3 H) -one; - (±) - 3 - [4-Chloro-2-f-loro-5- (1-methyl-2-propynyloxy) phenyl] -5- (1-methylcyclopropyl) -1,3,4-thiadiazole-2 ( 3H) -one.
3. 3. The herbicidal compositions as described in claim 1 or 2, wherein the amount by weight of the arylthiadiazolone having the general formula (I) is between 1 g / ha and 5 kg / ha.
4. 4. The herbicidal compositions as described in claim 3, wherein the amount by weight of the arylthiadiazolone having the general formula (I) is between 10 g / ha and 500 g / ha.
5. 5. The herbicidal compositions as described in any of the previous claims, wherein the ratio between the amount by weight of the arylthiadiazolone having the general formula (I) and the amount by weight of the products with herbicidal activity (b), varies from 99: 9.01 to 0.1: 99.9.
6. 6. The herbicidal compositions as described in claim 5, wherein the ratio between the amount by weight of the arylthiadiazolone having the general formula (I) and the amount by weight of the products with a herbicidal activity (b), varies from 99 : 1 to 1:99.
7. 7. The herbicidal compositions as described in any of the previous claims, useful in the pre-germination treatment of corn, cereals and soybeans, wherein the herbicides (b) are selected from: acetochlor, acifluorfen, aclonifen, alachlor, ametrin, atrazine , bifenox, butralin, chloramben, clomazone, chlorbromuron, chlorotoluron, chlorsulfuron, cyanazine, cyclosulfamuron (AC-322, 140), dietyl, diflufenican, dimethenamid, diphenamid, eglinazine, flucloralin, flumioxazin, fluoroglycofen, flupoxam, flurochloride, flurtamone, halosulfuron (NC-319), imazaquin, imazetapyr, isoproturon, isoxaben, isoxaflutol (RPA 201772), linuron, metazachlor , metabenzthiazuron, metobromuron, metolachlor, methoxuron, metribuzin, metsulfuron, monolinuron, norflurazon, orbencarb, oxadiazon, oxyfluorfen, pendimethalin, proglinazine, propachlor, prosulfocarb, SMY 1500, sulfentrazone, terbutrin, flutiamide (BAY FOE 5043), tri-alato, triasulfuron , trifluralin.
8. 8. The herbicidal compositions as described in any of the previous claims, useful in the treatment of rice crops, in which the herbicides (b) are selected from: acifluorfen, anilofos, azimulsufuron (DPX-A8947), bensulfuron, bensulide, benzofenap , bifenox, bispyribac-sodium (KHI-2023), bromobutide, butachlor, butenachlor, butralin, cafenstrol (CH-900), clometoxifen, clornitrofen, chlorprofam, cinmethilin, cinosulfuron, clomeprop, cumiluron, cyclosulfamuron (AC-322, 140), daimuron, diclobenil, dietyl, dimepiperate, dimethamethrin, esprocarb, ethoxysulfuron (HOE 095404), flucloralin, halosulfuron (NC-319), mefenacet, metildimiron, molinate, naproanilide, oxadiargyl, oxadiazon, oxaziciclomefona (MY-100), pentoxazone, piperofos, pretilaclor, propanil, pyrazolinate, pyrazulfuron, pyrazoxifen, piribenzoxim (LGC-40863), pyributicarb, pyriminobac-methyl (KIH-6127), quinclorac, symmetry, tenylchlor (NSK-850), thiobencarb, thiocarbazil.
9. 9. The herbicidal compositions as described in any of the previous claims, comprising liquid diluents, solid diluents, surfactants, dispersing agents, stabilizers, antifoaming agents and thickeners.
10. 10. The herbicidal compositions as described in any of the previous claims, wherein other herbicides, fungicides, phytoregulators, antibiotics, insecticides and fertilizers are present.
11. 11. The herbicidal compositions as described in any of the previous claims, which contain from 0.1% to 99% by weight of a combination of arylthiadiazolone having the general formula (I) with one or more herbicides (b) which are selected from those included above, from 1% to 99% by weight of a liquid or solid diluent, and from 0% to 25% by weight of a surfactant.