herbicidal composition and method for weed control in crops

专利摘要:
"herbicidal compositions comprising n- (tetrazol-5-yl) arylcarboxamides and n- (triazol-5-yl) arylcarboxamides". Herbicidal compositions comprising the active compounds of the group of n- (tetrazol-5-yl) - and n- (triazol-5-yl) arylcaboxamides and other herbicides and optionally protective agents are described. These herbicidal compositions are particularly suitable for use against harmful plants in useful plant crops.
公开号:BR112014028882B1
申请号:R112014028882
申请日:2013-05-22
公开日:2019-09-03
发明作者:Van Almsick Andreas；Waldraff Christian；Gatzweiler Elmar；Hacker Erwin；Menne Hubert；Trabold Klaus；Braun Ralf
申请人:Bayer Cropscience Ag；
IPC主号:

专利说明:

Described Report of the Invention Patent: HERBICIDE COMPOSITION AND METHOD FOR COMBATING WEEDS IN CROPS. DESCRIPTION [001] The present invention relates to agrochemically active herbicidal compositions, processes for their production and their use for the control of harmful plants.
[002] WO 2012/028579 A1 and previously unpublished EP11176378 document discloses certain N- (tetrazol-5-yl) and N- (triazol-5-yl) arylcaboxamides with herbicidal properties. However, these active compounds are not always sufficiently active against harmful plants and / or some of them are not sufficiently compatible with some important crops such as cereal, corn or rice species.
[003] It is therefore an object of the present invention to provide herbicidal compositions in which the activity against harmful plants and / or the selectivity of the herbicides mentioned above in relation to important crop plants is increased. This object is achieved by the herbicidal compositions according to the invention, which are described below and comprise certain N- (tetrazol-5-yl) - and N- (triazol-5-yl) arylcaboxamides, other herbicides and, optionally, agents of protection.
[004] The present invention provides herbicidal compositions comprising (A) one or more compounds of formula (I) (component A) or their salts
R
(I), in which the symbols and indices are each defined as follows: A represents N or CY,
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2/64
B represents N or CH, [005] X represents nitro, halogen, cyano, formyl, thiocyanate, (C1-C6) alkyl, halo- (C1-C6) -alkyl, (C2-C6) -alkenyl, halo- (C2 -C6) -alkenyl, (C2-C6) alkynyl, halo- (C3-C6) -alkynyl, (C3-C6) -cycloalkyl, halo- (C3-C6) -cycloalkyl, (C3-C6) -cycloalkyl- ( C1-C6) -alkyl, halo- (C3-C6) -cycloalkyl- (C1-C6) -alkyl, COR ¹ , COOR ¹ , OCOOR ¹ , NR ¹ COOR ¹ , C (O) N (R ¹ ) 2, NR ¹ C (O) N (R ¹ ) 2, OC (O) N (R ¹ ) 2, C (O) NR ¹ OR ¹ , OR ¹ , OCOR ¹ , OSO2R ² , S (O) nR ² , SO2OR ¹ , SO2N (R ¹ ) 2, NR ¹ SO2R ² , NR ¹ COR ¹ , (C1-C6) -alkyl-S (O) nR ² , (C1-C6) -alkyl-OR ¹ , (C1-C6) -alkyl-OCOR ¹ , (C1-C6) -alkyl-OSO2R ² , (C1-C6) -alkyl-CO2R ¹ , (C1-C6) -alkyl-SO2OR ¹ , (C1-C6) alkyl-CON (R ¹ ) 2, (C1-C6) -alkyl-SO2N (R ¹ ) 2, (C1-C6) -alkyl-NR ¹ COR ¹ , (C1-C6) alkyl-NR ¹ SO2R ² , NR ¹ R2, P (O ) (OR ⁵ ) 2, CH2P (O) (OR ⁵ ) 2, (C1-C6) -alkyletheroaryl, (C1-C6) -alkyleterocyclyl, where the last two radicals mentioned are each replaced by radicals from the group consisting of hal ogen, (C1C6) -alkyl, halo- (C1-C6) -alkyl, S (O) n- (C1-C6) -alkyl, (C1-C6) -alkoxy and halo (C1-C6) -alkoxy, and where heterocyclyl carries n oxo groups, [006] Y represents hydrogen, nitro, halogen, cyano, thiocyanate, (C1-C6) alkyl, halo- (C1-C6) -alkyl, (C2-C6) -alkenyl, halo- (C2-C6) -alkenyl, (C2-C6) alkynyl, halo- (C2-C6) -alkynyl, (C3-C6) -cycloalkyl, (C3-C6) -cycloalkenyl, halo (C3-C6) -cycloalkyl, (C3-C6) -cycloalkyl- (C1-C6) -alkyl, halo- (C3-C6) -cycloalkyl (C1-C6) -alkyl, COR ¹ , COOR ¹ , OCOOR ¹ , NR ¹ COOR ¹ , C (O ) N (R ¹ ) 2, NR ¹ C (O) N (R ¹ ) 2, OC (O) N (R ¹ ) 2, CO (NOR ¹ ) R ¹ , CHNOR ¹ , CH2ONC (R ¹ ) 2, NR ¹ SO2R ² , NR ¹ COR ¹ , OR ¹ , OSO2R ² , S (O) nR ² , SO2OR ¹ , SO2N (R ¹ ) 2 (C1-C6) alkyl-S (O) nR ² , (C1-C6 ) -alkyl-OR ¹ , (C1-C6) -alkyl-OCOR ¹ , (C1-C6) -alkylOSO2R ² , (C1-C6) -alkyl-CO2R ¹ , (C1-C6) -alkyl-CN, (C1 -C6) -alkyl-SO2OR ¹ , (C1C6) -alkyl-CON (R ¹ ) 2, (C1-C6) -alkyl-SO2N (R ¹ ) 2, (C1-C6) -alkyl-NR ¹ COR ¹ , (C1-C6) alkyl-NR ¹ SO2R ² , N (R ¹ ) 2, P (O) (OR ⁵ ) 2, CH2P (O) (OR ⁵ ) 1, (C1-C6) -alkylphenyl, (C1C6) -alkyletheroaryl, (C1-C6) -alkyletherocyclyl, phenyl, heteroaryl or heterocyclyl, where the last six radicals mentioned are each , replaced by radicals of the group consisting of halogen, nitro, cyano, (C1C6) -alkyl, halo- (C1-C6) -alkyl, (C3-C6) -cycloalkyl, S (O) n- (C1-C6 ) -alkyl, (C1
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C6) -alkoxy, halo- (C1-C6) -alkoxy, (C1-C6) -alkoxy- (C1-C4) -alkyl and cyanomethyl, and where heterocyclyl carries n oxo groups, [007] Z represents halogen, cyan , thiocyanate, halo- (C1-C6) -alkyl, (C2C6) -alkenyl, halo- (C2-C6) -alkenyl, (C2-C6) -alkynyl, halo- (C2-C6) -alquinyl, (C3- C6) -cycloalkyl, halo- (C3-C6) -cycloalkyl, (C3-C6) -cycloalkyl- (C1-C6) -alkyl, halo- (C3-C6) -cycloalkyl- (C1-C6) -alkyl, COLOR ¹ , COOR ¹ , OCOOR ¹ , NR ¹ COOR ¹ , C (O) N (R ¹ ) 2, NR ¹ C (O) N (R ¹ ) 2, OC (O) N (R ¹ ) 2, C ( O) NR ¹ OR ¹ , OSO2R ² , S (O) nR ² , SO2OR ¹ , SO2N (R ¹ ) 2, NR ¹ SO2R2, NR ¹ COR ¹ , (C1-C6) -alkyl-S (O) nR ² , (C1-C6) alkyl-OR ¹ , (C1-C6) -alkyl-OCOR ¹ , (C1-C6) -alkyl-OSO2R ² , (C1-C6) -alkyl-CO2R ¹ , (C1-C6) - alkyl-SO2OR ¹ , (C1-C6) -alkyl-CON (R ¹ ) 2, (C1-C6) -alkyl-SO2N (R ¹ ) 2, (C1C6) -alkyl-NR ¹ COR ¹ , (C1-C6 ) -alkyl-NR ¹ SO2R ² , N (R ¹ ) 2, P (O) (OR ⁵ ) 2, heteroaryl, heterocyclyl or phenyl, where the last three radicals mentioned are each replaced by radicals of the gr upo consisting of halogen, nitro, cyano, (C1-C6) -alkyl, halo- (C1-C6) -alkyl, (C3-C6) -cycloalkyl, S (O) n- (C1-C6) -alkyl, (C1-C6) -alkoxy and halo- (C1-C6) -alkoxy, and where heterocyclyl carries n oxo groups, or [008] Z may also represent hydrogen, (C1-C6) -alkyl or (C1-C6) alkoxy if Y represents the radical S (O) nR ² , [009] W represents hydrogen, (C1-C6) -alkyl, halo- (C1-C6) -alkyl, (C2C6) -alkenyl, halo- (C2-C6 ) -alkenyl, (C2-C6) -alkynyl, halo- (C2-C6) -alkynyl, (C3-C7) -cycloalkyl, (C3-C7) -halocycloalkyl, (C1-C6) -alkoxy, (C1-C6 ) -haloalkoxy, S (O) n- (C1-C6) -alkyl, S (O) n- (C1-C6) -haloalkyl, (C1-C6) -alkoxy- (C1-C4) -alkyl, (C1 -C6) -alkoxy- (C1-C4) -haloalkyl, halogen, nitro, NR ³ COR ³ or cyan, [010] R represents (C1-C8) -alkyl, halo- (C1-C8) -alkyl, (C2 -C8) -alkenyl, halo- (C2-C8) -alkenyl, (C2-C8) -alquinyl, halo- (C2-C8) -alquinyl, where these six radicals mentioned above are each replaced by radicals of the group consisting of hydrox i, nitro, cyano, SiR ⁵ 3, PO (OR ⁵ ) 2, S (O) n- (C1-C6) -alkyl, S (O) n- (C1-C6) -haloalkyl, (C1-C6) -alkoxy, halo- (C1-C6) -alkoxy, N (R ³ ) 2, COR ³ , COOR ³ , OCOR ³ , NR ³ COR ³ , NR ³ SO2R ⁴ , O (C1-C2) -alkyl- (C3 -C6) -cycloalkyl, (C3-C6) -cycloalkyl, heteroaryl, heterocyclyl, phenyl, Q-heteroaryl, Q
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4/64 heterocyclyl, Q-phenyl and Q-benzyl, where the last seven radicals mentioned are each replaced by radicals from the group consisting of methyl, ethyl, methoxy, trifluoromethyl, cyano and halogen, and where the heterocyclyl carries n oxo groups, or [011] R represents (C3-C7) -cycloalkyl, heteroaryl, heterocyclyl or phenyl, each of which is replaced by radicals of the group consisting of halogen, nitro, cyano, (C1-C6) - alkyl, halo- (C1-C6) -alkyl, (C3-C6) -cycloalkyl, S (O) n- (C1-C6) -alkyl, (C1-C6) -alkoxy, halo- (C1-C6) - alkoxy and (C1-C6) -alkoxy (C1-C4) -alkyl, where heterocyclyl carries n oxo groups,
Q represents O, S or NR ³ , [012] R ¹ represents hydrogen, (C1-C6) -alkyl, (C1-C6) -haloalkyl, (C2-C6) alkenyl, (C2-C6) -haloalkenyl, (C2 -C6) -alkynyl, (C2-C6) -haloalkynyl, (C3-C6) cycloalkyl, (C3-C6) -cycloalkenyl, (C3-C6) -halocycloalkyl, (C1-C6) -alkyl-O- (C1C6) -alkyl, (C3-C6) -cycloalkyl- (C1-C6) -alkyl, phenyl, phenyl- (C1-C6) -alkyl, heteroaryl, (C1-C6) -alkyletheroaryl, heterocyclyl, (C1-C6) -alkyleterocyclyl , (C1C6) -alkyl-O-heteroaryl, (C1-C6) -alkyl-O-heterocyclyl, (C1-C6) -alkyl-NR ³ heteroaryl or (C1-C6) -alkyl-NR ³ -heterocyclyl, where the the last twenty-one radicals mentioned are each replaced by radicals of the group consisting of cyan, halogen, nitro, thiocyanate, OR ³ , S (O) nR ⁴ , N (R ³ ) 2, NR ³ OR ³ , COR ³ , OCOR ³ , SCOR ⁴ , NR ³ COR ³ , NR ³ SO2R ⁴ , CO2R ³ , COSR ⁴ , CON (R ³ ) 2 and (C1C4) -alkoxy- (C2-C6) -alkoxycarbonyl, and where heterocyclyl carries n oxo groups, [013] R ² represents (C1-C6) -alkyl, (C1-C6) -haloalkyl, (C2-C 6) -alkenyl, (C2-C6) -haloalkenyl, (C2-C6) -alquinyl, (C2-C6) -haloalkynyl, (C3-C6) cycloalkyl, (C3-C6) -cycloalkenyl, (C3-C6) - halocycloalkyl, (C1-C6) -alkyl-O- (C1C6) -alkyl, (C3-C6) -cycloalkyl- (C1-C6) -alkyl, phenyl, phenyl- (C1-C6) -alkyl, heteroaryl, (C1 -C6) -alkyletheroaryl, heterocyclyl, (C1-C6) -alkyletherocyclyl, (C1C6) -alkyl-O-heteroaryl, (C1-C6) -alkyl-O-heterocyclyl, (C1-C6) -alkyl-NR ³ heteroaryl or (C1-C6) -alkyl-NR ³ -heterocyclyl, where the last 21 radicals mentioned are each replaced by radicals in the group consisting of cyano, halogen, nitro, thiocyanate, OR ³ , S (O) nR ⁴ , N (R ³ ) 2, NR ³ OR ³ , COR ³ ,
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OCOR ³ , SCOR ⁴ , NR ³ COR ³ , NR ³ SO2R ⁴ , CO2R3, COSR ⁴ , CON (R ³ ) 2 and (C1-C4) alkoxy- (C2-C6) -alkoxycarbonyl, and where heterocyclyl carries n groups oxo, [014] R ³ represents hydrogen, (C1-C6) -alkyl, (C2-C6) -alkenyl, (C2-C6) alkynyl, (C3-C6) -cycloalkyl, (C3-C6) -cycloalkyl- ( C1-C6) -alkyl or phenyl, [015] R ⁴ represents (C1-C6) -alkyl, (C2-C6) -alkenyl, (C2-C6) -alkynyl, (C3C6) -cycloalkyl, (C3-C6) -cycloalkyl- (C1-C6) -alkyl or phenyl,
R ⁵ represents (C1-C4) -alkyl, n represents 0, 1 or 2, s represents 0, 1, 2 or 3.
and [016] (B) one or more herbicides (component B) selected from groups B1 to B11
B1 1,3-diceto compounds comprising calcium prohexadione, ethyl trinexapac, [017] aloxidim, cletodim, cycloxidime, profoxidime, setoxidime, tepraloxidime, tralcoxidime, mesotrione, sulcotrione, tefuriltrione, tembotrione, bicyclone, bicyclone, bicyclone, bicyclopyrone,
B2 (sulfon) amides comprising [018] beflubutamide, bromobutide, dimethenamide, dimethenamide-P, diphenamide, napropamide, petoxamide, N- [3-chloro-4- (1-methylethyl) phenyl] -2methylpentanamide, naptalam, propizamide, [019 ] diflufenicão, etobenzanide, flufenacete, mefenacete, mefluidida, pentanochloro, picolinafeno, propanila, N-phenylftalâmico acid, [020] acetochloro, alachloro, butachloro, dimetachloro, metazachloro, metolachloro, propolachloro, propolachloro, 2 chloro-6'-ethylN-isopropoxymethylaceto-o-toluidide), tenylchlorine, [021] asulam, carbaryl, carbetamide, chlorprofam, demedipham, fenmedipham, profam,
Petition 870190063270, of 07/05/2019, p. 16/78
6/64 [022] butylate, cyclate, dimepiperate, EPTC, sprocarb, metasulfocarb, molinate, orbencarb, pebulate, prosulfocarb, pyributicarb, thiobencarb, trialate, vernolate, [023] amidosulfuron, azimsulfuron, chlorin sulfuron-chloro-sulfuron-methylsulfuron-methyl , cinosulfuron, cyclosulfamuron, etametsulfuron-methyl, ethoxysulfuron, flazassulfuron, flucethosulfuron, flupirsulfuron-methyl-sodium-sodium, foramsulfuron, halosulfuron-methyl, imazosulfuron, methanesulfon-methanesulfon-methanesulfon-metho-sulfuron, -methyl, prosulfuron, pyrazosulfuron-ethyl, rimsulfuron, sulfometuron-methyl, sulfosulfuron, tifensulfuron-methyl, triasulfuron, tribenuron-methyl, trifloxysulfuron (sodium), triflussulfuron-methyl, tritosl-[[benzylsulfuron] -methoxy-6- (methylthio) -2-pyrimidinyl] amino] carbonyl] amino] sulfonyl] methyl ester), [024] flucarbazone-sodium, prop oxycarbazone-sodium, thiencarbazonamethyl, [025] chloransulam-methyl, diclosulam, florasulam, flumetsulam, metosulam, penoxsulam, pyroxsulam,
B3 arylnitriles, comprising bromoxynil, diclobenyl, ioxynyl, pyraclonyl,
B4 azoles, comprising [026] benzofenap, pyrazolinate, pyrazoxifen, pyroxsulfone, topramezone, pyrasulfotole, 3- (3-chloro-5 - {[1-methyl-3- (trifluoromethyl) -1H-pyrazol-5-yl] oxy} phenoxy) -1 methyl-5- (trifluoromethyl) -1H-pyrazole, 3- (3-iodo-5 - {[1-methyl-3- (trifluoromethyl) -1Hpyrazol-5-yl] oxy} phenoxy) -1 - methyl-5- (trifluoromethyl) -1H-pyrazole, 1-ethyl-3- (3-fluoro-5 - {[1 methyl-3- (trifluoromethyl) -1H-pyrazol-5-yl] oxy} phenoxy) -5 - (trifluoromethyl) -1H-pyrazole, piraflufem-ethyl, fluazolate, isouron, isoxaben, isoxaflutol, [027] imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazetapir, metazol, oxadiargyl, oxadiargil
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7/64 amicarbazone, carfentrazone-ethyl, sulfentrazone, bencarbazone, amitrol, paclobutrazol, uniconazole, cafenstrol, fentrazamide,
B5 other herbicides, comprising [028] aminocyclopyrachlor, N-acetylthiazolidine-4-carboxylic acid, acrolein, aminopyralid, ammonium pelargonate, ammonium sulfamate, aviglycine, benazolin, benfluralin, benfuresate, bentazone, benzobicyclon, butyl benzine, 6-benzyl , carvone, catechin, chlorflurenol-methyl, chloridazon, chlormequate chloride, chloroacetic acid, chlorphtalim, chlortal-dimethyl, cinidon-ethyl, cinmetilin, clofencet, clomazone, cloxyfonac, cyanamide, cyclanilide, 6isopentinamine, dynesapentinamine, 6 dazomet, ndecanol, difenzoquat methyl sulfate, 2,6-diisopropylnaphthalene, dikegulac, dimethypine, dimethylarsenic acid, dinitraminea, dinoterb, diquat dibromide, dithiopir, DNOC, endothal, etafluralin, etofumesate, ethyl chloroate, sulfate-methylate, sulfate, propylate , flufenpir-ethyl, flumetralin, flumiclorac-pentyl, flumioxazin, flupropanate, flurenol, fluridone, flurochloridone, flurtamone, gibberyl acid , indanofan, isopropaline, isoprothiolan, maleic hydrazide, mepiquate chloride, metam, methylsonic acid, 1-methylcyclopropane, methyl isothiocyanate, nitrophenolate mixture, nonanoic acid, norflurazon, oleic acid, oryzalin, pentazyclohexate, dichloromethane , pentoxazone, petroleum oils, prodiamine, n-propyl dihydrojasmonate, pyridate, quinoclamine, sintofen, sodium chlorate, sulfuric acid, tar oils, sodium TCA, tecnazene, thiazopyr, triacontanol, trifluralin and urea sulfate,
B6 (het) arylcarboxylic acids, comprising dicamba, 2,3,6-TBA, clopyralid, fluroxypyr, inabenfide, picloram, triclopyr, quinclorac, quinmerac, indol-3-ylacetic acid, 4-indol-3-ylbutyric acid, 2- (1-naphthyl) acetamide, 1-naphthylacetic acid, 2-naphthyloxyacetic acid, B7 phosphorous organo compounds, comprising
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8/64 [029] anilophos, bensulide, bilanafos, butimafos, phosamine, glufosinate, glufosinate salts, ammonium glufosinate, sodium glufosinate, ammonium L-glufosinate, sodium l-glufosinate, glyphosate, glyphosate-amylophosphate ammonium glyphosate, glyphosate-trimesium (= sulfosate), diamonium glyphosate, glyphosatopotassium, piperophos, etefon and tribufos,
B8 phenyl ether, comprising [030] acifluorfen-sodium, aclonifen, fluoroglycophen-ethyl, fomesafen, lactofen, oxifluorfen, bifenox, ethoxyfen-ethyl, clomeprop, cloprop, dichorprop, dichorprop-P, mecoprop, mecoprop-P, mecoprop-P,
4-CPA, 2,4-D, MCPA, MCPA-thioethyl,
2,4-DB, MCPB, [031] clodinafope-propargil, butyl cihalofope, methyl diclofope, diclofope-P-methyl, phenoxaprope-P-ethyl, fluazifop-butyl, fluazifop-Pbutyl, haloxifope, haloxifop-P, metamifop, propaquizafope , quizalafope, quizalafope-P,
B9 pyramidines, comprising ancimidol, flurprimidol, pyrimisulfan, [032] bispyribac-sodium, pyribenzoxim, pyriminobac-methyl, pyribambenzisopropyl, pyribambenz-propyl, pyriftalid, piritiobaque-sodium, benzfendizone, 2-, broach, 33 chloro-4-fluoro-5- [3-methyl-2,6-dioxo-4- (trifluoromethyl) -3,6 dihydropyrimidin-1 (2H) -yl] -N- [methyl (1-methylethyl) -sulfamoyl] benzamide ,
B10 (uncle) ureas, comprising cumiluron, [034] chlorobromuron, chlorotoluron, chloroxuron, daimuron, diflufenzopyr, dimefuron, diuron, fluometuron, forclorfenuron, isoproturon, karbutilate, linuron, metildimon, metobromuron, monobururon, metobromuron, monobururon, metobromuron,
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9/64 tidiazuron, metiuron, tebutiuron, metabenztiazuron,
B11 triazines, comprising triaziflam, indaziflam, atrazine, cyanazine, propazine, simazine, terbuthylazine, trietazine, prometon, ametrim, dimetamethrin, prometim, simetrim, terbutrim, hexazinon, metamitron, metribuzim.
[035] In another configuration, these herbicidal compositions comprise (C), one or more protective agents (component C) of the group consisting of benoxacor (C1), cloquintocet-mexila (C2), cyprosulfamide (C3), dichlormide (C4) ), fenclorim (C5), fenclorazol (C6), furilazol (C7), isoxadifen-ethyl (C8), mefenpir-diethyl (C9), [036] 4- (dichloroacetyl) -1-oxa-4-azaspiro [4.5] CAS 71526-07-3 (C10), 2,2,5-trimethyl-3- (decloroacetyl) -1,3-oxazolidine CAS 52836-31-4 (C11).
[037] The components B) and C) are known, for example, from The Pesticide Manual, 15th edition, The British Crop Protection Council and the Royal Soc. Of Chemistry, and the site http://www.alanwood.net/ pesticides /.
[038] The herbicidal compositions of the invention may contain or be used in conjunction with other additional components, for example, other types of crop protection active ingredients and / or additives and / or formulation aids usual in crop protection.
[039] Herbicides (A), (B) and, optionally, protective agents (C) can be applied in a known way, for example, together (for example, as a co-formulation or as a mixture for tank) or at different times in rapid succession (fractionation), for example to plants, parts of plants, plant seeds or in the area where the plants grow. It is possible, for example, to apply the individual active compounds or to
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10/64 herbicide-protective agent combination in multiple portions (sequential application), for example, pre-emergence applications, followed by post-emergence applications, or early post-emergence applications followed by post-emergence applications in a intermediate or final stage. Preference is given to the joint or immediately successive application of the active compounds in the respective combination. It is also possible to use the individual active compounds or the herbicide-protective agent combination for seed treatment.
[040] Preference is given to compositions according to the invention which comprise, as herbicide (A), the compounds of general formula (I) and their salts, in which
A represents N or CY,
B represents N or CH, [041] X represents nitro, halogen, cyano, thiocyanate, (C1-C6) -alkyl, halo (C1-C6) -alkyl, (C2-C6) -alkenyl, halo- (C2-C6 ) -alkenyl, (C2-C6) -alquinyl, halo (C3-C6) -alquinyl, (C3-C6) -cycloalkyl, halo- (C3-C6) -cycloalkyl, (C1-C6) -alkyl-O (C1 -C6) -alkyl, (C3-C6) -cycloalkyl- (C1-C6) -alkyl, halo- (C3-C6) -cycloalkyl- (C1C6) -alkyl, COR ¹ , OR ¹ , OCOR ¹ , OSO2R ² , S (O) nR ² , SO2OR ¹ , SO2N (R ¹ ) 2, NR ¹ SO2R ² , NR ¹ COR ¹ , (C1-C6) -alkyl-S (O) nR ² , (C1-C6) -alkyl- OR ¹ , (C1-Ce) -alkylOCOR ¹ , (C1-C6) -alkyl-OSO2R ² , (C1-C6) -alkyl-CO2R ¹ , (C1-C6) -alkyl-SO2OR ¹ , (C1-C6) -alkyl-CON (R ¹ ) 2, (C1-C6) -alkyl-SO2N (R ¹ ) 2, (C1-C6) -alkyl-NR ¹ COR ¹ or (C1-C6) -alkyl-NR ¹ SO2R ² , (C1-C6) -alkyl-heteroaryl, (C1-C6) -alkyl-heterocyclyl, where the last two radicals mentioned are each replaced by radicals from the group consisting of halogen, (C1-C6) -alkyl , halo- (C1-C6) alkyl, S (O) n- (C1-C6) -alkyl, (C1-C6) -alkoxy and halo- (C1-C6) -alkoxy, and where heterocyclyl carries n oxo groups, [042] Y represents hydrogen, nitro, halogen, cyano, thiocyanate, (C1-C6) alkyl, halo- (C1-C6) -alkyl, (C2-C6) -alkenyl, halo - (C2-C6) -alkenyl, (C2-C6) alkynyl, halo- (C3-C6) -alkynyl, (C3-C6) -cycloalkyl, (C3-C6) -cycloalkenyl, halo (C3-C6) -cycloalkyl , (C3-C6) -cycloalkyl- (C1-C6) -alkyl, halo- (C3-C6) -cycloalkyl
Petition 870190063270, of 07/05/2019, p. 21/78
11/64 (Ci-Ce) -alkyl, COR ¹ , OR ¹ , COOR ¹ , OSO2R ² , S (O) nR ² , SO2OR ¹ , SO2N (R ¹ ) 2, N (R ¹ ) 2, NR ¹ SO2R ² , NR ¹ COR ¹ , (C1-C6) -alkyl-S (O) nR ² , (C1-C6) -alkyl-OR ¹ , (C1C6) -alkyl-OCOR ¹ , (C1-C6) -alkyl- OSO2R ² , (C1-C6) -alkyl-CO2R ¹ , (C1-Ce) -alkylSO2OR ¹ , (C1-C6) -alkyl-CON (R ¹ ) 2, (C1-C6) -alkyl-SO2N (R ¹ ) 2, (C1-C6) -alkylNR ¹ COR ¹ , (C1-C6) -alkyl-NR ¹ SO2R ² , (C1-Ce) -alkyl-phenyl, (C1-Ce) -alkyletheroaryl, (C1-C6) -alkyl-heterocyclyl, phenyl, heteroaryl or heterocyclyl, where the last six radicals mentioned are each replaced by radicals in the group consisting of halogen, nitro, cyano, (C1-C6) -alkyl, halo- (C1- C6) alkyl, (C3-C6) -cycloalkyl, S (O) n- (C1-C6) -alkyl, (C1-C6) -alkoxy, halo- (C1-C6) alkoxy, (C1-C6) -alkoxy - (C1-C4) -alkyl and cyanomethyl, and where heterocyclyl carries n oxo groups, [043] Z represents halogen, cyano, nitro, thiocyanate, halo- (C1-C6) -alkyl, (C2-C6) -alkenyl , halo- (C2-C6) -alkenyl, (C2-C6) -alkynyl, halo- (C3-C6) alkynyl, (C3-C6) -cycloalkyl, halo- (C3-C6) -cycloalkyl, (C3-C6) -cycloalkyl- (C1C6) -alkyl, halo- (C3-C6) -cycloalkyl- ( C1-C6) -alkyl, COR ¹ , COOR ¹ , C (O) N (R ¹ ) 2, C (O) NR ¹ OR ¹ , OSO2R ² , S (O) nR ² , SO2OR ¹ , SO2N (R ¹ ) 2, NR ¹ SO2R ² , NR ¹ COR ¹ , (C1-C6) -alkyl-S (O) nR ² , (C1-C6) -alkyl-OR ¹ , (C1-C6) -alkyl-OCOR ¹ , (C1-C6) -alkylOSO2R ² , (C1-C6) -alkyl-CO2R ¹ , (C1-C6) -alkyl-SO2OR ¹ , (C1-C6) -alkyl-CON (R ¹ ) 2, (C1-C6 ) -alkyl-SO2N (R ¹ ) 2, (C1-C6) -alkyl-NR ¹ COR ¹ , (C1-C6) -alkyl-NR ¹ SO2R ² , 1,2,4-triazole-1-yl, or [044] Z can also represent hydrogen, (C1-C6) -alkyl or (C1-C6) alkoxyl if Y represents the radical S (O) nR ² , [045] W represents hydrogen, (C1-C6) -alkyl, halo- (C1-C6) -alkyl, (C1C6) -alkoxy, (C1-C6) -haloalkoxy, S (O) n- (C1-C6) -alkyl, S (O) n- (C1-C6) haloalkyl , (C1-C6) -alkoxy- (C1-C4) -alkyl, halogen, nitro or cyano, [046] R represents (C1-C8) -alkyl, halo- (C1-C8) -alkyl, (C2-C8 ) -alkenyl, halo- (C2-C8) -alkenyl, (C2-C8) -alkynyl a, halo- (C2-C8) -alkynyl, where these last six radicals mentioned are each replaced by radicals of the group consisting of nitro, cyano, SiR ⁵ 3, P (OR ⁵ ) 3, S (O ) n- (C1-C6) -alkyl, (C1-C6) alkoxy, halo- (C1-C6) -alkoxy, N (R ³ ) 2, COR ³ , COOR ³ , OCOR ³ , NR ³ COR ³ ,
Petition 870190063270, of 07/05/2019, p. 22/78
12/64
NR ³ SO2R ⁴ , (C3-C6) -cycloalkyl, heteroaryl, heterocyclyl, phenyl, Q-heteroaryl, Qheterocyclyl, Q-phenyl and Q-benzyl, where the last seven radicals mentioned are each replaced by radicals from the group consisting of methyl, ethyl, methoxy, trifluoromethyl, cyano and halogen, and where heterocyclyl carries n oxo groups, or [047] R represents (C3-C7) -cycloalkyl, heteroaryl, heterocyclyl or phenyl, each of which is substituted by radicals of the group consisting of halogen, nitro, cyano, (C1-C6) -alkyl, halo- (C1-C6) -alkyl, (C3-C6) -cycloalkyl, S (O) n- (C1-C6 ) -alkyl, (C1-C6) -alkoxy, halo- (C1-C6) -alkoxy and (C1-C6) -alkoxy (C1-C4) -alkyl,
Q represents O, S or NR ³ , [048] R ¹ represents hydrogen, (C1-C6) -alkyl, (C2-C6) -alkenyl, (C2-C6) alkynyl, (C3-C6) -cycloalkyl, (C3 -C6) -cycloalkyl- (C1-C6) -alkyl, (C1-C6) -alkyl-O (C1-C6) -alkyl, phenyl, phenyl- (C1-C6) -alkyl, heteroaryl, (C1-C6) -alkyletheroaryl, heterocyclyl, (C1-C6) -alkylethylocyclyl, (C1-C6) -alkyl-O-heteroaryl, (C1-C6) alkyl-O-heterocyclyl, (C1-C6) -alkyl-NR ³ -heteroaryl or ( C1-C6) -alkyl-NR ³ heterocyclyl, where the last sixteen radicals mentioned are each replaced by radicals of the group consisting of cyano, halogen, nitro, OR ³ , S (O) nR ⁴ , N (R ³ ) 2, NR ³ OR ³ , COR ³ , OCOR ³ , NR ³ COR ³ , NR ³ SO2R ⁴ , CO2R ³ , CON (R ³ ) 2 and (C1-C4) -alkoxy- (C2-C6) -alkoxyacarbonyl , and where heterocyclyl carries n oxo groups, [049] R ² represents (C1-C6) -alkyl, (C2-C6) -alkenyl, (C2-C6) -alkynyl, (C3C6) -cycloalkyl, (C3-C6 ) -cycloalkyl- (C1-C6) -alkyl, (C1-C6) -alkyl-O- (C1-C6) alkyl, phenyl, phenyl- (C1-C6) -alkyl, heteroaryl , (C1-C6) -alkyletheroaryl, heterocyclyl, (C1-C6) -alkyleterocyclyl, (C1-C6) -alkyl-O-heteroaryl, (C1-C6) alkyl-O-heterocyclyl, (C1-C6) -alkyl- NR3-heteroaryl or (C1-C6) -alkyl-NR ³ heterocyclyl, where these last sixteen radicals mentioned are each replaced by radicals of the group consisting of cyano, halogen, nitro, OR ³ , S (O) nR ⁴ , N (R ³ ) ² , NR ³ OR ³ , NR ³ SO ² R ⁴ , COR ³ , OCOR ³ , NR ³ COR ³ , CO ² R ³ , CON (R ³ ) ² and (C1-C4) - alkoxy- (C2-C6) -alkoxyacarbonyl, and where heterocyclyl
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13/64 carries n oxo groups, [050] R ³ represents hydrogen, (C1-C6) -alkyl, (C2-C6) -alkenyl, (C2-C6) alkynyl, (C3-C6) -cycloalkyl or (C3- C6) -cycloalkyl- (C1-C6) -alkyl,
R ⁴ represents (C1-C6) -alkyl, (C2-C6) -alkenyl or (C2-C6) -alkynyl, R ⁵ represents methyl or ethyl, n represents 0, 1 or 2, s represents 0, 1,2 or 3.
[051] Preference is given to compositions according to the invention that comprise, as herbicide (A), those compounds of general formula (I) and their salts in which
A represents N or CY,
B represents N or CH, [052] X represents nitro, halogen, cyano, (C1-C6) -alkyl, halo- (C1-C6) alkyl, (C3-C6) -cycloalkyl, OR ¹ , S (O) nR ² , (C1-C6) -alkyl-S (O) nR ² , (C1-C6) alkyl-OR ¹ , (C1-C6) -alkyl-CON (R ¹ ) ² , (C1-C6) -alkyl- SO ² N (R ¹ ) ² , (C1-C6) -alkylNR ¹ COR ¹ , (C1-C6) -alkyl-NR ¹ SO ² R ² , (C1-C6) -alkyl-heteroaryl, (C1-C6) alkyletherocyclyl, where the last two radicals mentioned are each replaced by radicals from the group consisting of halogen, (C1-C6) -alkyl, halo- (C1-C6) -alkyl, S (O) n- (C1 -C6) -alkyl, (C1-C6) -alkoxy and halo- (C1-C6) alkoxy, and where heterocyclyl carries n oxo groups, [053] Y represents hydrogen, nitro, halogen, cyano, (C1-C6) -alkyl, (C1C6) -haloalkyl, OR1, S (O) ⁿ R ² , SO2N (R ¹ ) ² , N (R ¹ ) ² , NR ¹ SO ² R ² , NR ¹ COR ¹ , (C1C6) -alkyl -S (O) nR ² , (C1-C6) -alkyl-OR ¹ , (C1-C6) -alkyl-CON (R ¹ ) ² , (C1-C6) -alkylSO ² N (R1) ² , (C1 -C6) -alkyl-NR ¹ COR ¹ , (C1-C6) -alkyl-NR ¹ SO ² R ² , (C1-Ce) -alkylphenyl, (C1-C6 ) -alkyl-heteroaryl, (C1-C6) -alkyl-heterocyclyl, phenyl, heteroaryl or heterocyclyl, where the last six radicals mentioned are each replaced by radicals in the group consisting of halogen, nitro, cyano, (C1C6 ) -alkyl, halo- (C1-C6) -alkyl, (C3-C6) -cycloalkyl, S (O) n- (C1-C6) -alkyl, (C1C6) -alkoxy, halo- (C1-C6) - alkoxy, (C1-C6) -alkoxy- (C1-C4) -alkyl and cyanomethyl, and where heterocyclyl carries n oxo groups,
Petition 870190063270, of 07/05/2019, p. 24/78
14/64 [054] Z represents halogen, cyano, halo- (C1-C6) -alkyl, (C3-C6) cycloalkyl, S (O) nR2, 1,2,4-triazole-1-yl, or [055 ] Z can also represent hydrogen, methyl, methoxy or ethoxy if Y represents the radical S (O) nR ² radical, [056] W represents hydrogen, methyl, ethyl, methoxymethyl, methoxy, fluorine, chlorine or S (O) nCH3, [057] R represents (C1-C8) -alkyl, halo- (C1-C8) -alkyl, (C2-C8) -alkenyl, halo- (C2-C8) -alkenyl, (C2-C8) -alquinyl, halo - (C2-C8) -alkynyl, where these six radicals mentioned above are each replaced by radicals of the group consisting of cyano, S (O) n- (C1-C6) -alkyl, (C1-C6) -alkoxy, halo- (C1-C6) alkoxy, COR ³ , COOR ³ , OCOR ³ , NR ³ COR ³ , NR ³ SO2R ⁴ , (C3-C6) -cycloalkyl, heteroaryl, heterocyclyl and phenyl, where the last three radicals mentioned are each replaced by radicals from the group consisting of methyl, ethyl, methoxy, trifluoromethyl, cyan and halogen, and where heterocyclyl carries 0 to 2 oxo groups, [ 058] R represents phenyl substituted by radicals of the group consisting of halogen, nitro, cyano, (C1-C6) -alkyl, halo- (C1-C6) -alkyl, (C3-C6) cycloalkyl, S (O) n - (C1-C6) -alkyl, (C1-C6) -alkoxy, halo- (C1-C6) -alkoxy and (C1C6) -alkoxy- (C1-C4) -alkyl, [059] R ¹ represents hydrogen, ( C1-C6) -alkyl, (C2-C6) -alkenyl, (C2-C6) alkynyl, (C3-C6) -cycloalkyl, (C3-C6) -cycloalkyl- (C1-C6) -alkyl, (C1-C6 ) -Alkyl-O (C1-C6) -alkyl, phenyl, phenyl- (C1-C6) -alkyl, heteroaryl, (C1-C6) -alkyletheroaryl, heterocyclyl, (C1-C6) -alkyleterocyclyl, (C1-C6) -alkyl-O-heteroaryl, (C1-C6) alkyl-O-heterocyclyl, (C1-C6) -alkyl-NR ³ -heteroaryl or (C1-C6) -alkyl-NR ³ heterocyclyl, where the last sixteen radicals mentioned are , each replaced by radicals in the group consisting of cyan, halogen, nitro, OR ³ , S (O) nR ⁴ , N (R ³ ) 2, NR ³ OR ³ , COR ³ , OCOR ³ , NR ³ COR ³ , NR ³ SO2R ⁴ , CO2R ³ , CON (R ³ ) 2 and (C1-C4) -alkoxy- (C2-C6) -alkoxyacarbonyl, and where the heterocycle it carries n oxo groups,
R ² represents (C1-C6) -alkyl, (C3-C6) -cycloalkyl or (C3-C6)
Petition 870190063270, of 07/05/2019, p. 25/78
15/64 cycloalkyl- (C1-C6) -alkyl, each replaced by radicals in the group consisting of halogen and OR ³ ,
R ³ represents hydrogen or (C1-C6) -alkyl,
R ⁴ represents (C1-C6) -alkyl,
R ⁵ represents methyl or ethyl, n represents 0, 1 or 2, s represents 0, 1,2 or 3.
[060] Particular preference is given to those compositions according to the invention which comprise, as herbicide (A), the compounds of general formula (I) and their salts in which
A represents CY,
B represents N, [061] X represents chlorine, methyl, ethyl, propyl, cyclopropyl, methoxy or SO2CH3, [062] Y represents hydrogen, CH2OCH3, CH2OCH2CF3, CH2OC2H4OCH3, 4,5-dihydro-1,2-oxazol-3- ila, 5-methoxymethyl-4,5-dihydro-1,2-oxazol-3-yl, pyrazol-1 ila, OMe, OEt, OPr, OiBu, OCH2cPr, OC2H4OCH3, SO2 CH3, S (O) CH3 or SCH3, SO2Et, S (O) Et or SEt,
Z represents trifluoromethyl, SO2CH3, SO2Et, chlorine or bromine,
W represents hydrogen, and
R represents methyl, ethyl, propyl or methoxyethyl.
[063] Particular preference is given to compositions according to the invention which comprise, as herbicide (A), the compounds of general formula (I) and their salts in which
A represents CY,
B represents N,
X represents chlorine,
Y represents SO2CH3, SOCH3 or SO2Et,
Z represents hydrogen or methyl,
W represents hydrogen, and
Petition 870190063270, of 07/05/2019, p. 26/78
16/64
R represents methyl.
[064] Particular preference is also given to compositions according to the invention which comprise, as herbicide (A), those compounds of general formula (I) and their salts in which
A represents CY,
B represents N,
X represents chlorine or bromine,
Y represents hydrogen, methyl, SO2CH3 or SCH3,
Y represents hydrogen, SO2CH3 or SCH3,
W represents methyl, and
R represents methyl or ethyl, [065] Particular preference is also given to those compositions according to the invention which comprise, as herbicide (A), compounds of general formula (I) and their salts in which
A represents CY,
B represents CH,
X represents chlorine or methyl, [066] Y represents 4,5-dihydro-1,2-oxazol-3-yl, pyrazol-1-yl, OC2H4OCH3 or SO2CH3,
Z represents trifluoromethyl, SO2CH3, SO2Et or chlorine,
W represents hydrogen, and
R represents methyl.
[067] Particular preference is also given to compositions according to the invention that comprise, as herbicide (A), those compounds of general formula (I) and their salts in which
A represents N,
B represents N, [068] X represents chlorine, bromine, SO2CH3, methoxymethyl, OCH2cPr, OC2H4OCH3 or methyl,
Z represents trifluoromethyl,
Petition 870190063270, of 07/05/2019, p. 27/78
17/64
W represents hydrogen, and
R represents methyl or ethyl, [069] In formula (I) and in all the formulas that follow, alkyl radicals that have more than two carbon atoms can be straight or branched. Alkyl radicals are, for example, methyl, ethyl, n- or isopropyl, n, iso-, tert- or 2-butyl, pentyls, hexyls, such as n-hexyl, isohexyl and 1,3dimethylbutyl. Similarly, alkenyl represents, for example, allyl, 1methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1- ila, 1methylbut-3-en-1-yl and 1-methylbut-2-en-1-yl. Alquinyl represents, for example, propargyl, but-2-in-1-yl, but-3-in-1-yl, 1-methylbut-3-in-1-yl. The multiple bond can, in each case, be in any position of the unsaturated radical. Cycloalkyl represents a saturated carbocyclic ring system with three to six carbon atoms, for example, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. Similarly, cycloalkenyl represents a monocyclic alkenyl group with 3 to 6 members on the carbon ring, for example, cyclopropenyl, cyclobutenyl, cyclopentenyl and cyclohexenyl, where the double bond can be in any position.
Halogen represents fluorine, chlorine, bromine or iodine.
[070] Heterocyclyl represents a saturated, semi-saturated or totally unsaturated cyclic radical containing 3 to 6 atoms in the ring, of which 1 to 4 are from the oxygen, nitrogen and sulfur group, and which can be additionally fused by a benzo ring. For example, heterocyclyl represents piperidinyl, pyrrolidinyl, tetrahydrofuranyl, dihydrofuranyl and oxetanil.
[071] Heteroaryl represents a cyclic aromatic radical containing 3 to 6 atoms in the ring, of which 1 to 4 are from the oxygen, nitrogen and sulfur group, and which can additionally be fused by a benzo ring. Heteroaryl represents, for example, benzimidazol-2-yl, furanyl, imidazolyl, isoxazolyl, isothiazolyl, oxazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyridinyl, benzisoxazolyl, thiazolyl, pyrrolyl, pyrazolyl, 1,2-thiozenyl 2,4oxadiazolyl, 1,2,5-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,4-triazolyl, 1,2,3
Petition 870190063270, of 07/05/2019, p. 28/78
18/64 triazolyl, 1,2,5-triazolyl, 1,3,4-triazolyl, 1,2,4-triazolyl, 1,2,4-thiadiazolyl, 1,3,4 thiadiazolyl, 1,2,3-thiadiazolyl , 1,2,5-thiadiazolyl, 2H-1,2,3,4-tetrazolyl, 1H-1,2,3,4tetrazolyl, 1,2,3,4-oxatriazolyl, 1,2,3,5-oxatriazolyl , 1,2,3,4-thiatriazolyl and 1,2,3,5-thiatriazolyl.
[072] When a group is polysubstituted by radicals, this means that that group is replaced by one or more identical or different radicals from those mentioned. This applies in a similar way to the formation of ring systems by several atoms and elements. At the same time, the scope of the claims does not include those compounds known to a person skilled in the art as being chemically unstable under standard conditions.
[073] The present invention also provides herbicidal compositions comprising stereoisomers and mixtures thereof, which are encompassed by formula (I) or by the formulas of component B. Such compounds of formula (I) or formulas of component B contain, for example, example, one or more asymmetrically substituted carbon atoms or sulfoxides. The possible stereoisomers defined by their specific three-dimensional shape, such as enantiomers and diastereoisomers, are all covered by formula (I), or by components B and C; especially racemic mixtures and when enantiomers are possible - both enantiomers and, especially, the respective biologically active enantiomer. Individual stereoisomers can be obtained by the usual methods from mixtures of stereoisomers or by stereoselective reactions in combination with the use of stereochemically pure or auxiliary starting materials.
[074] Examples of compounds used as herbicide (A) are listed in the following tables:
[075] In these tables, the abbreviations used mean:
Et = ethyl Me = methyl n-Pr = n-propyl i-Pr = isopropyl c-Pr = cyclopropyl Ph = phenyl Ac = acetyl i-Bu = isobutyl [076] Table 1: Compounds of general formula (I) in which A represents CY and
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19/64
B represents N and W represents hydrogen
Z
Ex. R X Y Z A1-1 Me Cl H SO2Me A1-2 Me SO2Me H CF3 A1-3 Me Me SMe CF3 A1-4 MeOC2H4 Me SMe CF3 A1-5 Me Me SOMe CF3 A1-6 Et Me SOMe CF3 A1-7 Me Me SO2Me CF3 A1-8 Et Me SO2Me CF3 A1-9 Pr Me SO2Me CF3 A1-10 MeOC2H4 Me SO2Me CF3 A1-11 Me Me SEt CF3 A1-12 Et Me SEt CF3 A1-13 Me Me SOEt CF3 A1-14 Et Me SOEt CF3 A1-15 Me Me SO2Et CF3 A1-16 Et Me SO2Et CF3 A1-17 Me Me SO2Me Cl A1-18 Me Me SEt Cl A1-19 Me Me SOEt Cl A1-20 Et Me SOEt Cl A1-21 Me Me SO2Et Cl A1-22 Me Me SMe Br A1-23 Me Me SEt Br A1-24 Me Me 4,5-dihydro-1,2-oxazol-3-yl SO2Me A1-25 Et Me 4,5-dihydro-1,2-oxazol-3-yl SO2Me A1-26 Me Me pyrazol-1-il SO2Me A1-27 Et Me pyrazol-1-il SO2Me
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20/64
A1-28 Me Me SMe SO2Me A1-29 Me Me SO2Me SO2Me A1-30 Et Me SO2Me SO2Me A1-31 Me Me SO2Et SO2Me A1-32 Et Me SO2Et SO2Me A1-33 Me Et SMe CF3 A1-34 Me Et SOMe CF3 A1-35 Me Et SO2Me CF3 A1-36 Me Et SMe Cl A1-37 Et Et SMe Cl A1-38 Me Et SOMe Cl A1-39 Me Et SMe Br A1-40 Me Et SO2Me Br A1-41 Me Pr SMe CF3 A1-42 Me Pr SOMe CF3 A1-43 Me c-Pr SMe CF3 A1-44 Me OMe SMe CF3 A1-45 Me OMe SOMe CF3 A1-46 Me OMe SO2Me CF3 A1-47 Me OMe SEt CF3 A1-48 Me Cl SMe H A1-49 Me Cl SO2Me Me A1-50 Me Cl SO2Et Me A1-51 Me Cl SO2Me CF3 A1-52 Me Cl OC2H4OMe Cl A1-53 Me Cl SMe Cl A1-54 Et Cl SMe Cl A1-55 Me Cl SOMe Cl A1-56 Et Cl SOMe Cl A1-57 Me Cl SO2Me Cl A1-58 Et Cl SO2Me Cl A1-59 Me Cl SO2Et Cl A1-60 Me Cl CH2OMe SO2Me
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21/64
A1-61 Me Cl CH2OCH2CF3 SO2Me A1-62 Et Cl CH2OCH2CF3 SO2Me A1-63 Me Cl OC2H4OMe SO2Me A1-64 Me Cl 4,5-dihydro-1,2-oxazol-3-yl SO2Me A1-65 Me Cl 4,5-dihydro-1,2-oxazol-3-yl SO2Et A1-66 Me Cl 5-methoxymethyl-4,5-dihydro-1,2-oxazol-3-yl SO2Et A1-67 Me Cl OMe SO2Me A1-68 Me Cl OMe SO2Et A1-69 Me Cl OEt SO2Me A1-70 Me Cl OEt SO2Et A1-71 Me Cl OPr SO2Me A1-72 Me Cl OPr SO2Et A1-73 Me Cl Hi-Bu SO2Me A1-74 Me Cl OCH2C-Pr SO2Me A1-75 Me Cl OCH2C-Pr SO2Et A1-76 Me Cl OC2H4OMe SO2Me A1-77 Me Cl SMe SO2Me A1-78 Me Me OMe SO2Me A1-79 Et OMe SMe CHF2 A1-80 Me OMe SO2Me CHF2 A1-81 Me OMe SMe CHF2 A1-82 Me OMe SOMe CHF2 A1-83 Me Cl O (CH2) 3OMe SO2Et A1-84 Et Cl SOMe Me A1-85 Me Cl SMe CF3
[077] Table 2: Compounds of general formula (I) in which A represents CY and
B represents CH and W represents hydrogen
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Ex. R X Y Z A2-1 Me Me SÜ2Me CF3 A2-2 Me Me 4,5-dihydro-1,2-oxazol-3-yl SO2Me A2-3 Me Me pyrazol-1-il SO2Me A2-4 Me Me SO2Me SO2Me A2-5 Me Cl SO2Me Cl A2-6 Me Cl 4,5-dihydro-1,2-oxazol-3-yl SO2Me A2-7 Me Cl 4,5-dihydro-1,2-oxazol-3-yl SO2Et A2-8 Me Cl OC2H4OMe SO2Me A2-9 Me Cl SÜ2Me CF3 A2-10 Me Cl SO2Et CF3
[078] Table 3: Compounds of general formula (I) in which A represents CY and
B represents N
N
R
O
X
H
Y
W
Z
Ex. R X Y Z W A3-1 Me Cl H SMe Me A3-2 Me Cl SMe H Me A3-3 Me Cl SO2Me H Me A3-4 Et Cl SO2Me H Me A3-5 Me Cl Me SMe Me A3-6 Et Cl Me SO2Me Me A3-7 Me Br SO2Me H Me
[079]
Table 4: Compounds of the general formula (I) in which A represents N and B represents N and W represents hydrogen
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23/64
Ex. No. R X Z A4-1 Me Me CF3 A4-2 Me CH2OMe CF3 A4-3 Et CH2OMe CF3 A4-4 Me OC2H ₄ OMe CF3 A4-5 Et OC2H ₄ OMe CF3 A4-6 Me CH2OCH2c-Pr CF3 A4-7 Me Cl CF3 A4-8 Me Br CF3 A4-9 Me SO2Me CF3
[080] Preferred group B1 herbicides are clethodim, setoxidim, tepraloxidim, mesotrione, sulcotrione, tefuriltrione, tembotrione, bicyclopyrone, pinoxaden, tralcoxidim.
[081] Particularly preferred group B1 herbicides are clethodim, sulcotrione, tefuriltrione, tembotrione, bicyclopyrone and pinoxaden.
[082] Herbicides preferred in the B2 group are dimethenamide, dimethenamideP, napropamide, petoxamide, propizamide, diflufenicon, flufenacet, mefenacet, picolinafen, propanyl, acetochlor, alachlor, butachlor, metazachlor, metolachlor, metolachlor, metolachlor, metolachloride, metolachloride, metholachloride, metolachloride, metolachloride, metolachloride, , desmedifam, fenmedifam, sprocarb, molinate, prosulfocarb, thiobencarb, amidosulfuron, chlorimuron-ethyl, cyclosulfamuron, ethoxysulfuron, flupirsulfuron-methyl-sodium, foramsulfuron, iodosulfuron-methyl-sulfonur, sulfonuronylsulfuron, sulfururon, , rimsulfuron, trifloxysulfuron (sodium), sodium flucarbazone, sodium propoxycarbazone, thiencarbazone-methyl, florassulam, metosulam penoxsulam, metsulfuron-methyl, sulfosulfuron, tifensulfuronmethyl, tribenuron-methyl, tritosulfuron.
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24/64 [083] Particularly preferred group B2 herbicides are dimethenamideP, napropamide, diflufenicon, flufenacet, mefenacet, acetochlor, metazachlor, S-metolachlor, asulam, demedipham, fenmedipham, molinate, prosulfocarbon, amidosulfuron, amidosulfuron, were -sodium, mesosulfuron-methyl, sodium flucarbazone, sodium propoxycarbazone, thiencarbazone-methyl, florassulam, metosulam, metsulfuron-methyl, sulfosulfuron, tifensulfuron-methyl, tribenuron-methyl, tritosulfuron, pyroxsulam,
Preferred herbicides of the B3 group are bromoxynil and ioxynil.
[084] Preferred herbicides in the B4 group are benzofenap, topramezone, pyrasulfotole, isoxaflutole, imazamox, imazetapyr, oxadiargyl, oxadiazon, amicarbazone, carfentrazone-ethyl, sulfentrazone, uniconazole, cafenstrol, 3-fentrazamide 1-methyl-3- (trifluoromethyl) -1H-pyrazol-5-yl] oxy} phenoxy) -1 methyl-5- (trifluoromethyl) -1H-pyrazole, 3- (3-iodo-5 - {[1-methyl -3- (trifluoromethyl) -1Hpyazol-5-yl] oxy} phenoxy) -1-methyl-5- (trifluoromethyl) -1H-pyrazole, 1-ethyl-3- (3-fluoro-5 - {[1 methyl- 3- (trifluoromethyl) -1H-pyrazol-5-yl] oxy} phenoxy) -5- (trifluoromethyl) -1H-pyrazole, piraflufen-ethyl.
[085] Particularly preferred group B4 herbicides are pyrasulfotole, isoxaflutole, oxadiargyl, amicarbazone, fentrazamide, 3- (3-chloro-5 - {[1-methyl-3 (trifluoromethyl) -1H-pyrazol-5-yl] oxy} phenoxy) -1-methyl-5- (trifluoromethyl) -1H-pyrazole, 3 (3-iodo-5 - {[1-methyl-3- (trifluoromethyl) -1H-pyrazol-5-yl] oxy} phenoxy) - 1-methyl-5 (trifluoromethyl) -1H-pyrazole, 1-ethyl-3- (3-fluoro-5 - {[1-methyl-3- (trifluoromethyl) -1Hpyrazol-5-yl] oxy} phenoxy) -5 - (trifluoromethyl) -1H-pyrazole, piraflufen-ethyl, imazamox. [086] Preferred herbicides of the B5 group are aminopyralide, benazolin, benfuresate, bentazone, cinidon-ethyl, clomazone, diquat dibromide, etofumesate, flumichlorac-pentyl, flumioxazin, flurtamone, oxaziclomefone, pendimetalin, pyridine and pyridate and pyridine.
[087] Particularly preferred group B5 herbicides are aminopyralide, benfuresate, etofumesate, flurtamone and oxaziclomefone.
[088] Preferred group B6 herbicides are dicamba, clopyralid, fluroxypyr,
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25/64 picloram, triclopir, quinclorac.
[089] Preferred herbicides of the B7 group are anilophos, ammonium glufosinate and ammonium L-glufosinate, glyphosate, glyphosate-isopropyl-ammonium, ammonium glyphosate, glyphosate-trimesium (= sulfosate), diamonium glyphosate, potassium glyphosate.
[090] Preferred herbicides of the B8 group are acifluorfen-sodium, aclonifen, fluoroglycophene-ethyl, oxyfluorfen, bifenox, dichlorprope-P, mecoprope-P, 2,4-D, MCPA, clodinafope-propargil, butylcyclopop, methyl diclofope, diclofope methyl, diclofope methyl, diclofope methyl, diclofope methyl, diclofope methyl, diclofope methyl, diclofope methyl, diclofope methyl, diclofope methyl, diclofope methyl. -Pmethyl, phenoxaprope-P-ethyl, fluazifop-P-butyl, quizalofop-P.
[091] Particularly preferred herbicides of the B8 group are aclonifen, methyl diclofope, diclofop-P-methyl, phenoxaprope-P-ethyl, MCPA, clodinafop-ethyl.
[092] Particularly preferred group B9 herbicides are bispiribac (sodium), pyriftalid, bromacila, lenacil, 2-chloro-4-fluoro-5- [3-methyl-2,6-dioxo-4 (trifluoromethyl) -3,6 -dihydropyrimidin-1 (2H) -yl] -N- [methyl (1-methylethyl) sulfamoyl] benzamide, [093] Preferred herbicides in the B9 group are bispiribac (sodium) and bromacila.
[094] Preferred group B10 herbicides are cumiluron, daimuron, diuron, isoproturon, diflufenzopyr.
[095] Preferred herbicides of the B11 group are atrazine, simazine, terbuthylazine, ametrine, terbutrine, metamitron, metribuzin.
[096] Particularly preferred group B11 herbicides are metamitron, metribuzin and terbuthylazine.
[097] In the herbicidal compositions according to the invention, the application rate of the herbicides of general formula (I) (component A) is generally 1 to 500 g of active ingredient (ia) per hectare, preferably from 2 to 300 g ai / ha, especially preferably from 3 to 200 g ai / ha. The application rate of component B herbicides is generally 1 to 5000 g of active ingredient (a.i.) per hectare, preferably 2 to 3000 g a.i./ha, especially preferably 3 to 2000 g a.i./ha. The application rate of protection agents
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26/64 of component C is generally 1 to 500 g of active ingredient (a.i.) per hectare, preferably 2 to 400 g a.i./ha, especially preferably 3 to 300 g a.i./ha.
[098] By applying the herbicidal compositions according to the invention, a very wide spectrum of harmful plants, for example, monocot or dicot weeds and unwanted crops, is controlled in pre-emergence and post-emergence methods. The herbicidal compositions according to the invention are particularly suitable for use in crops such as cereals, corn, rice, soybeans, rapeseed, sugar beet, cotton, sugar cane, and also for use in perennial crops, plantations and in uncultivated land . They are also highly suitable for use in transgenic crops of maize, cereals, sugar beet, rice, cotton and soy (Glycine max., For example, RR soy and LL soy and hybrids thereof), Phaseolus, Pisum, Vicia and Arachis , or vegetables from various botanical groups, such as potatoes, leeks, cabbage, carrots, tomatoes, onions, and also perennial crops and crops such as plants of the Pomoideae subfamily and stone fruits, soft fruits, wine, Hevea, bananas , sugar cane, coffee, tea, citrus, nut plantations, lawn, palm crops and forest crops. For the use of the herbicide-protective agent (A) + (B) combinations according to the invention, these crops are also preferred, with particular preference being given to use in cereals (for example, wheat, barley, rye, oats ), rice, maize, millet / sorghum, sugar beet, sugar cane, sunflower, rapeseed and cotton. Combinations of herbicide-protective agent (A) + (B) can also be used in tolerant and non-tolerant mutant crops and tolerant and non-tolerant transgenic crops, preferably maize, rice, cereals, cotton, sugar beet and soybeans , for example, those resistant to the herbicides of imidazolinone, atrazine, glufosinate, glyphosate, 2,4-D, dicamba and herbicides of the hydroxyphenylpyruvate dioxigenase group, such as sulcotrione, mesotrione, tembotrione, tefuriltrione, benzobicyclon, bicyclopyrone and bicyclopyrone.
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27/64 [099] An amount effective as a herbicide in the sense of the present invention is an amount of one or more herbicides suitable to have an adverse impact on plant growth. An active amount as an antidote in the context of the present invention means an amount of one or more protective agents suitable for reducing the phytotoxic effect of the active compounds of crop protection compositions (for example, herbicides) in crops.
[100] According to their properties, the protective agents (C) present in the herbicidal compositions according to the invention can also each be used for the pre-treatment of the seed of the plant (for example, for the treatment seeds) or introduced into the seed grooves before sowing or used in conjunction with the herbicide before or after the emergence of the plants. Pre-emergence treatment includes treating the growing area (including all the water present in the growing area, for example, in the case of rice applications) before sowing and treating the growing areas where the seeds have been sown but are not yet covered by growing plants. Preference is given to application in conjunction with the herbicide. For this purpose, it is possible to use tank mixes or ready-made formulations.
[101] In a preferred configuration, the seed (for example, grains, seeds or vegetative propagating organs, such as tubers or parts of shoots) or seedlings are pre-treated with protective agents (C), optionally in combination with other agrochemically active compounds. For seed pre-treatment, the active compounds can be applied to the seeds, for example, by treatment, or the active compounds and the seed can be added to water or other solvents, and the active compounds can be incorporated, for example, by adsorption or diffusion in an immersion process or by swelling or pre-germination. For pretreatment of seedlings, young plants can be placed in contact with protective agents, optionally in combination with other compounds
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28/64 active agrochemicals, for example, by spraying, immersion or irrigation, and then transplanted and optionally further treated with the herbicides (A) and (B).
[102] Seeds or seedlings can be treated with protective agents (C) alone or in conjunction with other active agrochemicals - such as fungicides, insecticides or plant fortifiers, fertilizers or swelling or germination accelerators. After the pretreatment application, the protective agents can subsequently be applied again, before, after or together with one or more herbicides of formula (I) (A) and herbicides (B), possibly also in combination with other herbicides known. The pretreatment of seeds or seedlings can achieve an improved long-term action of protective agents.
[103] The present invention therefore further provides a method for combating unwanted plants in crops, which is characterized by the fact that the components (A), (B) and optionally (C) of the herbicide compositions according to invention are used, for example, separately or together, in plants (for example, noxious plants such as monocots or dicots or unwanted crops), in seeds (for example, grains, seeds or vegetative propagating organs, such as tubers or grafted parts of shoots) or in the area where the plants grow (for example, the growing area). One or more protective agents (C) can be applied before, after or simultaneously with the herbicide (s) of general formula (I) (A) and herbicides (B) on the plants, seed or the area where the plants grow (for example, the growing area). In a preferred configuration, protective agents (C) are used for seed treatment.
[104] Undesirable plants are all plants that grow in places where they are not desired. These can, for example, be harmful plants (for example, monocot or dicot weeds, or unwanted crop plants), including, for example, those that are
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29/64 resistant to certain active herbicidal compounds, such as glyphosate, atrazine, glufosinate or imidazolinone herbicides.
[105] Monocotyledon weeds are classified, for example, in the genera Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Fescue, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera. Dicotyledonous weeds are classified, for example, in the genera Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosu, Cirsium, , Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum, Euphorbia.
[106] The invention also provides the use of the herbicidal compositions according to the invention for the control of unwanted vegetation, preferably in crops.
[107] The herbicidal compositions according to the invention can be prepared by known processes, for example, as mixed formulations of the individual components, if appropriate with other usual active compounds, additives and / or formulation aids, the combinations of which are then applied in a usual manner diluted with water, or as tank mixtures by jointly diluting the individual components, formulated separately or partially formulated separately, with water. It is also possible to divide the application of the individual components formulated separately or partially formulated separately. It is also possible to apply individual components or herbicidal compositions in a plurality of portions (sequential application), for example, pre-emergence applications, followed by post-emergence or early post-emergence applications, followed by applications in the middle post-emergence or late. Preference is given to the joint or immediately successive application of
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30/64 active compounds in the respective combination.
[108] The herbicidal compositions according to the invention can also be used for the control of harmful plants in crops of genetically modified plants that are known or are yet to be developed.
[109] In general, transgenic plants are notable for their special advantageous properties, for example, resistance to certain pesticides, in particular, certain herbicides, resistance to plant diseases or organisms that cause plant diseases, such as certain insects or microorganisms such as fungi , bacteria or viruses. Other particular properties refer, for example, to the material harvested in relation to quantity, quality, storage capacity, composition and specific constituents. For example, transgenic plants are known with a high starch content or altered starch quality, or with a different fatty acid composition in the harvested material. Other particular properties may be tolerance or resistance to abiotic stress agents, for example, heat, low temperatures, drought, salinity and ultraviolet radiation.
[110] Preference is given to the use of the herbicidal compositions according to the invention in economically important transgenic crops of useful and ornamental plants, for example, cereals such as wheat, barley, rye, oats, millet / sorghum, rice, cassava and corn, or sugar beet crops, cotton, soy, rapeseed, potatoes, tomatoes, peas and other vegetables.
[111] Conventional ways of producing new plants that have modified properties compared to plants that have occurred to date consist, for example, of traditional generation methods and the generation of mutants. Alternatively, new plants with modified properties can be generated with the help of recombinant methods (see, for example, EP-A-0221044, EP-A-0131624). For example, there have been several descriptions of:
- genetic modifications of crop plants for the purpose of
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31/64 modifying the starch synthesized in plants (for example, WO 92/011376, WO 92/014827, WO 91/019806);
- transgenic crop plants that are resistant to particular herbicides of the glufosinate type (see, for example, EPA-0242236, EP-A-242246) or the glyphosate type (WO 92/00377) or the sulfonylurea type (EP documents -A-0257993, US-A5013659);
- transgenic crop plants, for example, cotton, with the ability to produce Bacillus thuringiensis toxins (Bt toxins), which make plants resistant to specific pests (EP-A0142924, EP-A-0193259);
- transgenic cultures with a modified fatty acid composition (WO 91/13972);
- genetically modified crop plants with new constituents and secondary metabolites, such as new phytoalexins, which cause increased resistance to diseases (EPA 309862, EPA0464461);
- genetically modified plants with reduced photorespiration that have higher yields and greater tolerance to stress (EPA 0305398).
- transgenic crop plants that produce important pharmaceutical or diagnostic proteins (molecular pharming);
- transgenic crop plants with higher yields or better quality;
- transgenic crop plants that are distinguished by a combination, for example, of the new properties mentioned above (genetic stacking).
[112] In principle, a large number of molecular biology techniques are known, through which new transgenic plants with
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Modified 32/64 can be generated; see, for example, I. Potrykus and G. Spangenberg (eds.) Gene Transfer to Plants, Springer Lab Manual (1995), Springer Verlag Berlin, Heidelberg, or Christou, Trends in Plant Science 1 (1996) 423-431).
[113] For such recombinant manipulations, nucleic acid molecules that allow mutagenesis or sequence change by recombination of DNA sequences can be introduced into plasmids. With the help of standard methods it is possible, for example, to change bases, remove parts of strings or add natural or synthetic strings. For joining DNA fragments to each other, adapters or ligands can be attached to the fragments; see, e.g., Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd ed. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY; or Winnacker Gene und Klone [Genes and Clones], VCH Weinheim 2nd edition 1996.
[114] For example, the generation of plant cells with reduced activity of a genetic product can be achieved by the expression of at least one corresponding antisense RNA, a sense RNA to achieve a co-suppression effect, or by expression of at least less an appropriately constructed ribozyme, which specifically cleaves transcripts of the aforementioned gene product.
[115] For this it is possible, first, to use DNA molecules that cover the entire coding sequence of a genetic product, including any side sequences that may be present, and also DNA molecules that cover only parts of the coding sequence, being necessary that these portions are long enough to have an antisense effect in the cells. It is also possible to use DNA sequences that have a high degree of homology with the coding sequences of a genetic product, but that are not completely identical to them.
[116] When expressing nucleic acid molecules in plants, the protein
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The synthesized 33/64 can be located in any desired compartment of the plant cell. However, to achieve localization in a particular compartment, it is possible, for example, to join the coding region to the DNA sequences that ensure the location in a particular compartment. Such sequences are known to those skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106). Nucleic acid molecules can also be expressed in the organelles of plant cells.
[117] Cells from transgenic plants can be regenerated by known techniques to generate complete plants. In principle, transgenic plants can be plants of any desired species, that is, both monocotyledonous and dicotyledonous plants.
[118] For example, it is possible to obtain transgenic plants whose properties are altered by overexpression, suppression or inhibition of homologous (= natural) genes or gene sequences, or expression of heterologous (= foreign) genes or gene sequences.
[119] Preferably, the compounds according to the invention can be used in transgenic cultures that are resistant to growth regulators, for example, dicamba, or to herbicides that inhibit essential plant enzymes, for example, acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydroxyphenylpyruvate dioxigenases (HPPD), or to herbicides in the group of sulfonylureas, glyphosate, glufosinates or benzoylisoxazoles and similar active compounds.
[120] When using the compositions according to the invention in transgenic cultures, not only the weed effects observed in other cultures occur, but also the effects that are specific to the application in the transgenic culture in particular, for example, an altered or specifically expanded spectrum of weeds that can be controlled, changed application rates that can be used for
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34/64 application, preferably a good combination characteristic with the herbicides to which the transgenic crop is resistant, and influences the growth and yield of transgenic crop plants.
[121] The invention therefore provides the use of the herbicidal compositions according to the invention for the control of harmful plants in transgenic crops.
[122] Preference is given to the use of the herbicidal compositions according to the invention in economically important transgenic crops of useful and ornamental plants, for example, cereals (for example, wheat, barley, rye, oats), millet / sorghum, rice , cassava and corn, or sugar beet, cotton, soy, rapeseed, potatoes, tomatoes, peas and other vegetables.
[123] The invention therefore provides the use of the herbicidal compositions according to the invention for the control of harmful plants in transgenic crops or crops that have tolerance through selective breeding.
[124] Herbicides (A), (B) and protective agents (C) can be converted together or separately into usual formulations, for example, for spraying, watering, spraying and seed treatment, as well as solutions , emulsions, suspensions, powders, foams, pastes, granules, aerosols, synthetic or natural substances impregnated with the active ingredient, microencapsulation in polymeric substances. The formulations may comprise customary auxiliaries and additives.
[125] These formulations are produced in a known way, for example, by mixing the active compounds with diluents, that is, liquid solvents, liquefied gases under pressure and / or solid vehicles, optionally with the use of surfactants (surfactants), ie , emulsifying and / or dispersing agents and / or foaming agents.
[126] If the diluent used is water, it is also possible to use, for example, organic solvents as auxiliary solvents. Useful liquid solvents are essentially: aromatics such as xylene, toluene or alkylnaphthalenes,
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35/64 chlorinated aromatic compounds or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example, fractions of mineral oils, mineral and vegetable oils, alcohols, such as butanol or glycol and the ethers and esters thereof, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide or dimethylsulfoxide and water.
[127] Useful solid vehicles include: for example, ammonium salts and ground natural minerals, such as kaolin, clays, talc, chalk, quartz, atapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as finely divided silica, alumina and silicates; solid vehicles useful for granules include: for example, crushed and fractionated natural rocks, such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic flours, and granules of organic materials such as sawdust, bark coconut, corn cobs and tobacco stems; Useful emulsifiers and / or foaming agents include: for example, nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example, alkylaryl polyglycol ethers, alkylsulfonates, alkylsulphates, arylsulfonates and hydrolysates of protein; Useful dispersants include: for example, residual lignosulfite and methylcellulose liquors.
[128] In formulations, it is possible to use adhesion agents, such as carboxymethylcellulose, natural and synthetic polymers in the form of powders, granules or latexes, such as arabic gum, polyvinyl alcohol and polyvinyl acetate, or else natural phospholipids such as cephalins and synthetic lecithins and phospholipids. Other additives can be mineral and vegetable oils.
[129] It is possible to use dyes, such as inorganic pigments, for example, iron oxide, titanium oxide and Prussian Blue, and organic dyes such as alizarin dyes, azo dyes and metallic phthalocyanine dyes, and micronutrients such as salts iron, manganese, boron, copper, cobalt,
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36/64 molybdenum and zinc.
[130] Formulations generally contain between 0.1 and 95 weight percent of active ingredient, preferably between 0.5 and 90 weight percent.
[131] As such or in their formulations, herbicides (A), (B) and protective agents (C) can also be used as a mixture with other agrochemically active compounds to control unwanted vegetation, for example, to the control of weeds or to combat unwanted crop plants, with ready-made formulations or tank mixes, for example, being possible.
[132] Mixtures with other active compounds known as fungicides, insecticides, acaricides, nematicides, bird repellents, plant nutrients and soil improvers are also possible, as well as with additives and formulation aids commonly used in crop protection.
[133] Herbicides (A), (B) and protective agents (C) can be used as such, in the form of their formulations or in the forms of use prepared from them by further dilution, such as ready-to-use solutions , suspensions, emulsions, powders, pastes and granules. The application is usually carried out, for example, by watering, spraying, spraying, or diffusing.
[134] The active compounds can be used in plants, in parts of plants, in seeds or in the cultivated area (land), preferably on the seed or in green plants and parts of plants and, optionally, additionally on land. One means of application is the co-use of active compounds in the form of tank mixtures, by mixing the ideally formulated concentrated formulations of the individual active substances together in the tank with water and using the spray liquor obtained.
[135] A co-formulation of the combination according to the invention of the active compounds (A), (B) and (C) has the advantage of being easily applicable, because the quantities of the components can already be defined in the ideal proportion in relation to each other. In addition, formulation aids can be optimized with respect to each other.
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37/64 [136] For application, formulations present in their commercial form are, if necessary, diluted in the usual way, for example, in the case of wettable powders, emulsifiable concentrates, dispersions and granules dispersible in water, with water. Preparations in the form of powder, granules for application to the soil or granules for sowing and spray solutions are generally no longer diluted with other inert substances before application.
Biological Examples:
- Test conditions in the greenhouse test [137] The weed seeds were sown in pots (8 cm in diameter) with sandy-clay soil and germinated under ideal conditions. The herbicides were applied by the post-emergence method in the pots with the cultures, in a syrup volume of 300 l / ha. The herbicides were applied alone and in combination. The test was conducted in a greenhouse under ideal growing conditions. The effects of herbicides were evaluated visually by comparing untreated and treated plants. The percentages mean: 0% = no effect, 100% = the plants die completely. The percentages are used to calculate the interactions between the individual treatments and the combination treatments according to S.R. Colby, Weeds 15, pages 20 to 22 (1967).
The results are shown in the tables below.
- Test conditions in the field test [138] The tests were carried out outdoors (batch tests, 10 m ² per batch, 2 repetitions, spray application with 200 to 300 liters of water per hectare). Broadleaf / weed crops and weeds were sown under usual field conditions. In addition, a natural weed flora also appeared. The application was made using the post-emergence method. Application rates for herbicidal active compounds applied alone or in combinations are also shown in the tables below. The evaluations were by visual score (using a scale from 0 to 100%) after
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38/64 the application, by comparing treated and untreated test variants. The results (as an average of all plants / lot and for two repetitions) are shown in the table below.
Seed treatment [139] Seed grains from cultivated plants were mixed and shaken in bottles with protective agents formulated as concentrates for suspension or emulsion and water, such that the seed grains were coated homogeneously with the formulation of the respective protective agent. Seed grains or plants after emergence were then treated with herbicides by pre-emergence or post-emergence methods. Here, numerous herbicide / protective agent compositions according to the invention have shown good compatibility with crop plants and, at the same time, good herbicidal activity against a wide spectrum of harmful plants.
Abbreviations mean:
a.i. = active ingredient
EC = expected value according to Colby (E ^C = A + B - AxB / 100)
Δ = difference (%) from the measured value to the expected value (%) (measured value minus the expected value)
Evaluation:
- measured value E is greater than E ^C : -> synergism (+ Δ)
- measured value E is equal to E ^C : -> additive effect
- measured value E is less than E ^C : -> antagonism (-Δ) [140] Table 5-01: Greenhouse
Active compound Dosage[g of i.a / ha] Activity (%) againstAvena fatua A1-2 2 0 phenoxaprop-P-ethyl 25 0 A1 -2 + phenoxaprop-P-ethyl 2 + 25 15 (E ^C = 0, Δ = 15)
[141] Table 5-02: Greenhouse
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Active compound Dosage[g of i.a / ha] Activity (%) againstViola tricolor A1-2 2 60 phenoxaprop-P-ethyl 25 0 A1-2 + phenoxaprop-P-ethyl 2 + 25 80 (E ^C = 60, Δ = 20)
[142] Table 5-03: Greenhouse
Active compound Dosage[g of i.a / ha] Activity (%) againstPhalaris minor A1-2 2 0 phenoxaprop-P-ethyl 25 15 A1-2 + phenoxaprop-P-ethyl 2 + 25 30 (E ^C = 15, Δ = 15)
[143] Table 5-04: Field
Active compound Dosage[g of i.a / ha] Activity (%) againstGalium aparine A1-2 25 70 bromoxynil 210 1325 + 210 100 (E ^C = 74, Δ = 26)
[144] Table 5-05: Greenhouse
Active compound Dosage[g of i.a / ha] Activity (%) againstAvena fatua A1-7 3 0 phenoxaprop-P-ethyl 12.5 0 A1-7 + phenoxaprop-P-ethyl 3 + 12.5 20 (E ^C = 0, Δ = 20)
[145] Table 5-06: Greenhouse
Active compound Dosage[g of i.a / ha] Activity (%) againstPapaver rhoeas A1-7 3 60 phenoxaprop-P-ethyl 12.5 20 A1-7 + phenoxaprop-P-ethyl 3 + 25 85 (E ^C = 68, Δ = 17)
[146] Table 5-07: Greenhouse
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Active compound Dosage[g of i.a / ha] Activity (%) againstAvena fatua A1-7 3 0 phenoxaprop-P-ethyl 12.5 0 A1-7 + phenoxaprop-P-ethyl 3 + 25 10 (E ^C = 0, Δ = 10)
[147] Table 5-08: Greenhouse
Active compound Dosage[g of i.a / ha] Activity (%) against Polygonum convolvulus A1-7 3 10 phenoxaprop-P-ethyl 25 0 A1-7 + phenoxaprop-Petil 3 + 25 20 (E ^C = 10, Δ = 10)
[148] Table 5-09: Greenhouse
Active compound Dosage[g of i.a / ha] Activity (%) againstViola tricolor A1-7 3 50 phenoxaprop-P-ethyl 12.5 15 A1-7 + phenoxaprop-P-ethyl 3 + 12.5 85 (E ^C = 58, Δ = 28)
[149] Table 5-10: Field
Active compound Dosage[g of i.a / ha] Activity (%) againstSpinosa AIDS A1-9 10 60 glufosinate-ammonium 125 50 A1-9 + glufosinate-ammonium 10 + 125 95 (E ^C = 80, Δ = 15)
[150] Table 5-11: Field
Active compound Dosage[g of i.a / ha] Activity (%) againstSpinosa AIDS
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A1-9 10 60 glyphosate-potassium 200 30 A1-9 + glyphosate-potassium 10 + 200 85 (E ^C = 72, Δ = 13)
[151] Table 5-12: Field
Active compound Dosage[g of i.a / ha] Activity (%) againstCassia obtusifolia A1-9 20 0 glyphosate 200 65 A1-9 + glyphosate 20 + 200 85 (E ^C = 65, Δ = 20)
[152] Table 5-13: Field
Active compound Dosage[g of i.a / ha] Activity (%) againstPortulaca oleracea A1-9 20 43 atrazine 250 25 A1-9 + atrazine 20 + 250 100 (E ^C = 57, Δ = 43)
[153] Table 5-14: Field
Active compound Dosage[g of i.a / ha] Activity (%) againstPortulaca oleracea A1-9 20 43 foramsulfuron 16 0 A1-9 + foramsulfuron 20 + 16 85 (E ^C = 43, Δ = 42)
[154] Table 5-15: Field
Active compound Dosage[g of i.a / ha] Activity (%) againstPortulaca oleracea A1-9 20 43 mesotrione 25 0 A1-9 + mesotrione 20 + 25 70 (EC = 43, Δ = 27)
[155] Table 5-16: Field
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Active compound Dosage[g of i.a / ha] Activity (%) againstPortulaca oleracea A1-9 20 43 metribuzin 50 0 A1-9 + metribuzin 20 + 50 75 (E ^C = 43, Δ = 32)
[156] Table 5-17: Field
Active compound Dosage[g of i.a / ha] Activity (%)againstAbutilon theophrasti A1-9 20 78 dimethenamide-P 500 25 A1-9 +dimethenamide-P 20 + 500 85 (E ^C = 79, Δ = 6)
[157] Table 5-18: Field
Active compound Dosage[g of i.a / ha] Activity (%) againstPortulaca oleracea A1-9 20 43 bicyclopyrone 25 23 A1-9 + bicyclopyrone 20 + 25 90 (E ^C = 56, Δ = 34)
[158] Table 5-19: Field
Active compound Dosage[g of i.a / ha] Activity (%) againstPortulaca oleracea A1-9 20 43 nicosulfuron 20 30 A1-9 + nicosulfuron 20 + 20 68 (E ^C = 60, Δ = 8)
[159] Table 5-20: Field
Active compound Dosage[g of i.a / ha] Activity (%) againstPortulaca oleracea
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A1-9 20 43 rimsulfuron 6 0 A1-9 + rimsulfuron 20 + 6 68 (E ^C = 43, Δ = 25)
[160] Table 5-21: Field
Active compound Dosage[g of i.a / ha] Activity (%) againstSpinosa AIDS A1-9 10 60 metribuzin 50 25 A1-9 + metribuzin 10 + 50 79 (E ^C = 60, Δ = 19)
[161] Table 5-22: Field
Active compound Dosage[g of i.a / ha] Activity (%) againstPortulaca oleracea A1-9 10 38 aclonifen 1200 0 A1-9 + aclonifen 10 + 1200 83 (E ^C = 38, Δ = 45)
[162] Table 5-23: Field
Active compound Dosage[g of i.a / ha] Activity (%) againstSetaria viridis A1-9 10 15 topramezone 9 30 A1-9 +topramezone 10 + 9 75 (E ^C = 40, Δ = 35)
[163] Table 5-24: Field
Active compound Dosage[g of i.a / ha] Activity (%) againstCassia obtusifolia A1-9 20 0 indaziflam 25 65 A1-9 + indaziflam 20 + 25 83 (E ^C = 65, Δ = 18)
[164] Table 5-25: Field
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Active compound Dosage[g of i.a / ha] Activity (%) againstCassia obtusifolia A1-9 25 65 bromoxynil 210 10 A1-9 + bromoxynil 25 + 210 90 (E ^C = 69, Δ = 22)
[165] Table 5-26: Field
Active compound Dosage[g of i.a / ha] Activity (%) againstSetaria viridis A1-9 25 7 MCPA 280 0 A1-9 + MCPA 25 + 280 95 (E ^C = 75, Δ = 20)
[166] Table 5-27: Greenhouse
Active compound Dosage[g of i.a / ha] Activity (%) againstSetaria viridis A1-23 2 50 lenacil 8 0 A1-23 + lenacil 2 + 8 60 (E ^C = 50, Δ = 10)
[167] Table 5-28: Greenhouse
Active compound Dosage[g of i.a / ha] Activity (%) againstHairy bidens A1-23 2 45 lenacil 4 0 A1-23 + lenacil 2 + 4 70 (E ^C = 45, Δ = 25)
[168] Table 5-29: Greenhouse
Active compound Dosage[g of i.a / ha] Activity (%) againstAmbrosia artemisiifolia A1-23 1 10 lenacil 16 0 A1-23 + lenacil 1 + 16 45 (E ^C = 10, Δ = 35)
[169] Table 5-30: Greenhouse
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Active compound Dosage[g of i.a / ha] Activity (%) againstPharbitis purpurea A1-23 1 45 lenacil 4 0 A1-23 + lenacil 1 + 4 75 (E ^C = 45, Δ = 30)
[170] Table 5-31: Greenhouse
Active compound Dosage[g of i.a / ha] Activity (%) againstSetaria viridis A1-23 2 50 lenacil 8 0 A1-23 + lenacil 2 + 8 70 (E ^C = 50, Δ = 20)
[171] Table 5-32: Greenhouse
Active compound Dosage[g of i.a / ha] Activity (%) againstAmbrosiaartemisiifolia A1-23 1 0 lenacil 4 0 A1-23 + lenacil 1 + 4 25 (E ^C = 0, Δ = 25)
[172] Table 5-33: Greenhouse
Active compound Dosage[g of i.a / ha] Activity (%) againstHairy bidens A1-23 1 35 lenacil 4 0 A1-23 + lenacil 1 + 4 65 (E ^C = 35, Δ = 30)
[173] Table 5-34: Greenhouse
Active compound Dosage[g of i.a / ha] Activity (%) againstPharbitis purpurea A1-23 2 45 lenacil 4 0
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A1-23 + lenacil 2 + 4 75 (E ^C = 45, Δ = 30)
[174] Table 5-35: Greenhouse
Active compound Dosage[g of i.a / ha] Activity (%) againstDigitaria sanguinalis A1-23 1 10 lenacil 4 0 A1-23 + lenacil 1 + 4 40 (E ^C = 10, Δ = 30)
[175] Table 5-36: Greenhouse
Active compound Dosage[g of i.a / ha] Activity (%)againstDigitaria sanguinalis A1-24 6 50 pendimetalin 50 0 A1-24 +pendimetalin 6 + 50 80 (E ^C = 50, Δ = 30)
[176] Table 5-37: Greenhouse
Active compound Dosage[g of i.a / ha] Activity (%) against Polygonum convolvulus A1-24 6 0 pendimetalin 100 0 A1-24 +pendimetalin 6 + 100 30 (E ^C = 0, Δ = 30)
[177] Table 5-38: Greenhouse
Active compound Dosage[g of i.a / ha] Activity (%) againstCentaurea cyanis A1-26 3 40 pinoxaden 5 0
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A1-26 + pinoxaden 3 + 5 60 (EC = 40, Δ = 20) beautiful 5-39: Greenhouse
Active compound Dosage[g of i.a / ha] Activity (%) againstPapaver rhoeas A1-26 6 50 pinoxaden 5 0 A1-26 + pinoxaden 6 + 5 70 (EC = 50, Δ = 20)
Table 5-40: Greenhouse [179]
Active compound Dosage[g of i.a / ha] Activity (%) againstCentaurea cyanis A1-26 6 60 pinoxaden 5 15 A1-26 + pinoxaden 6 + 5 85 (EC = 66, Δ = 19)
Table 5-41: Greenhouse [180]
Active compound Dosage[g of i.a / ha] Activity (%) againstPapaver rhoeas A1-26 3 30 pinoxaden 10 10 A1-26 + pinoxaden 3 + 10 60 (EC = 37, Δ = 23)
Table 5-42: Greenhouse [181]
Active compound Dosage[g of i.a / ha] Activity (%) againstViola tricolor A1-26 3 50 pinoxaden 10 0 A1-26 + pinoxaden 3 + 10 70 (EC = 50, Δ = 15)
Table 5-43: Greenhouse [182]
Active compound Dosage[g of i.a / ha] Activity (%) againstSetaria viridis A1-33 2 75
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isoproturon 200 10 A1 -33 + isoproturon 2 + 200 95 (E ^C = 78, Δ = 18)
[183] Table 5-44: Greenhouse
Active compound Dosage[g of i.a / ha] Activity (%) against Polygonum convolvulus A1-33 4 0 isoproturon 200 0 A1-33 +isoproturon 4 + 200 20 (E ^C = 0, Δ = 20)
[184] Table 5-45: Greenhouse
Active compound Dosage[g of i.a / ha] Activity (%) against Brachiaria platyphylla A1-36 2 25 imazamox 2 10 A1-36 + imazamox 2 + 2 65 (E ^C = 33, Δ = 32)
[185] Table 5-46: Greenhouse
Active compound Dosage[g of i.a / ha] Activity (%) againstHairy bidens A1-36 2 45 imazamox 1 10 A1-36 + imazamox 2 + 1 70 (E ^C = 51, Δ = 19)
[186] Table 5-47: Greenhouse
Active compound Dosage[g of i.a / ha] Activity (%) againstHairy bidens A1-36 4 30 imazamox 2 20 A1-36 + imazamox 4 + 2 65 (E ^C = 44, Δ = 21)
[187] Table 5-48: Field
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Active compound Dosage[g of i.a / ha] Activity (%) againstAmaranthusretroflexus A1-36 50 0 atrazine 560 60 A1 -36 + atrazine 50 + 560 92 (E ^C = 60, Δ = 32)
[188] Table 5-49: Greenhouse
Active compound Dosage[g of i.a / ha] Activity (%)againstAvena fatua A1-44 4 0 phenoxaprop-P-ethyl 25 0 A1 -44 + phenoxaprop-Petil 4 + 25 15 (E ^C = 0, Δ = 15)
[189] Table 5-50: Greenhouse
Active compound Dosage[g of i.a / ha] Activity (%)againstCentaurea cyanis A1-44 8 50 phenoxaprop-P-ethyl 25 0 A1 -44 + phenoxaprop-Petil 8 + 25 65 (E ^C = 50, Δ = 15)
[190] Table 5-51: Field
Active compound Dosage[g of i.a / ha] Activity (%) againstEuphorbia heterophylla A1-44 25 58 atrazine 1000 49 A1 -44 + atrazine 25 + 1000 94 (E ^C = 70, Δ = 15)
[191] Table 5-52: Greenhouse
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Active compound Dosage[g of i.a / ha] Activity (%)againstAmbrosia artemisiifolia A1-49 4 80 thiencarbazone-methyl 0.25 0 A1-49 +thiencarbazone-methyl 4 + 0.25 98 (E ^C = 80, Δ = 18)
[192] Table 5-53: Field
Active compound Dosage[g of i.a / ha] Activity (%) againstPolygunum convolvulus A1-49 25 35 bromoxynil 210 30 A1-49 + bromoxynil 25 + 210 78 (E ^C = 55, Δ = 24)
[193] Table 5-54: Field
Active compound Dosage[g of i.a / ha] Activity (%) againstLolium multiflorum A1-49 25 40 MCPA 280 0 A1-49 + MCPA 25 + 280 60 (E ^C = 40, Δ = 20)
[194] Table 5-55: Greenhouse
Active compound Dosage[g of i.a / ha] Activity (%) againstBrachiaria platyphylla A1-60 1 0 lenacil 4 0 A1-60 + lenacil 1 + 4 15 (E ^C = 0, Δ = 15)
[195] Table 5-56: Greenhouse
Active compound Dosage[g of i.a / ha] Activity (%) againstXanthium strumarium
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A1-60 1 25 lenacil 4 0 A1-60 + lenacil 1 + 4 55 (E ^C = 25, Δ = 30)
[196] Table 5-57: Greenhouse
Active compound Dosage[g of i.a / ha] Activity (%) againstBrachiaria platyphylla A1-60 2 40 lenacil 4 0 A1-60 + lenacil 2 + 4 65 (E ^C = 40, Δ = 25)
[197] Table 5-58: Field
Active compound Dosage[g of i.a / ha] Activity (%) againstLolium multiflorum A1-60 25 15 diflufenican 120 10 A1-60 + diflufenican 25 + 120 50 (E ^C = 24, Δ = 27)
[198] Table 5-59: Field
Active compound Dosage[g of i.a / ha] Activity (%) againstCentaurea cyanis A1-60 25 45 flufenacet 240 0 A1 -60 + flufenacet 25 + 240 63 (E ^C = 45, Δ = 18)
[199] Table 5-60: Field
Active compound Dosage[g of i.a / ha] Activity (%) againstAlopecurus myosuroides A1-60 25 15 phenoxaprop-P-ethyl 83 30 A1-60 + 25 + 83 60 (E ^C = 41, Δ = 20)
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phenoxaprop-P-ethyl
[200] Table 5-61: Field
Active compound Dosage[g of i.a / ha] Activity (%) againstGalium aparine A1-60 25 30 MCPA 280 0 A1-60 + MCPA 25 +280 65 (E ^C = 30, Δ = 35)
[201] Table 5-62: Field
Active compound Dosage[g of i.a / ha] Activity (%) againstGalium aparine A1-60 25 73 bromoxynil 210 13 A1-60 + bromoxynil 25 +210 100 (E ^C = 77, Δ = 23)
[202] Table 5-63: Field
Active compound Dosage[g of i.a / ha] Activity (%) againstEuphorbia heterophylla A1-60 25 30 atrazine 1000 49 A1 -60 + atrazine 25 +1000 91 (E ^C = 64, Δ = 27)
[203] Table 5-64: Greenhouse
Active compound Dosage[g of i.a / ha] Activity (%) againstBrachiaria platyphylla A1-61 6 0 dicamba 25 10 A1-61 + dicamba 6 + 25 30 (E ^C = 10, Δ = 20)
[204] Table 5-65: Greenhouse
Active compound Dosage[g of i.a / ha] Activity (%) againstSetaria viridis
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A1-61 3 0 dicamba 25 0 A1-61 + dicamba 3 + 25 15 (E ^C = 0, Δ = 15)
[205] Table 5-66: Field
Active compound Dosage[g of i.a / ha] Activity (%) againstVeronica hederifolia A1-61 25 68 bromoxynil 210 5 A1-61 + bromoxynil 25 +210 99 (E ^C = 70, Δ = 29)
[206] Table 5-67: Greenhouse
Active compound Dosage[g of i.a / ha] Activity (%) againstBrachiaria platyphylla A1-63 8 10 lenacil 800 0 A1-63 + lenacil 8 + 800 35 (E ^C = 10, Δ = 25)
[207] Table 5-68: Greenhouse
Active compound Dosage[g of i.a / ha] Activity (%) againstDigitaria sanguinalis A1-63 8 45 lenacil 400 0 A1-63 + lenacil 8 + 400 80 (E ^C = 45, Δ = 35)
[208] Table 5-69: Greenhouse
Active compound Dosage[g of i.a / ha] Activity (%) againstEchinochloa crus-galli A1-63 8 85 lenacil 400 0 A1-63 + lenacil 8 + 400 98 (E ^C = 85, Δ = 13)
[209] Table 5-70: Greenhouse
Active compound Dosage Activity (%) against
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[g of i.a / ha] Setaria viridis A1-63 4 50 lenacil 100 0 A1-63 + lenacil 4 + 100 75 (E ^C = 50, Δ = 25)
[210] Table 5-71: Greenhouse
Active compound Dosage[g of i.a / ha] Activity (%) againstHairy bidens A1-63 8 50 lenacil 400 0 A1-63 + lenacil 8 + 400 85 (E ^C = 50, Δ = 35)
[211] Table 5-72: Greenhouse
Active compound Dosage[g of i.a / ha] Activity (%) againstPharbitis purpurea A1-63 4 35 lenacil 100 0 A1-63 + lenacil 4 + 100 55 (E ^C = 35, Δ = 20)
[212] Table 5-73: Greenhouse
Active compound Dosage[g of i.a / ha] Activity (%) againstXanthium strumarium A1-63 8 80 lenacil 400 0 A1-63 + lenacil 8 + 400 95 (E ^C = 80, Δ = 15)
[213] Table 5-74: Field
Active compound Dosage[g of i.a / ha] Activity (%) againstVeronica hederifolia A1-63 25 68 bromoxynil 210 5 A1-63 + bromoxynil 25 +210 93 (E ^C = 70, Δ = 23)
[214] Table 5-75: Greenhouse
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Active compound Dosage[g of i.a / ha] Activity (%)againstAmbrosia artemisiifolia A1-66 6 35 thiencarbazone-methyl 0.25 0 A1-66 +thiencarbazone-methyl 6 + 0.25 80 (E ^C = 35, Δ = 45)
[215] Table 5-76: Field
Active compound Dosage[g of i.a / ha] Activity (%) againstVeronica hederifolia A1-66 25 75 bromoxynil 210 0 A1-66 + bromoxynil 25 +210 100 (E ^C = 75, Δ = 25)
[216] Table 5-77: Greenhouse
Active compound Dosage[g of i.a / ha] Activity (%) against Xanthium strumarium A1-67 4 0 pendimetalin 100 0 A1-67 +pendimetalin 4 + 100 20 (E ^C = 0, Δ = 20)
[217] Table 5-78: Greenhouse
Active compound Dosage[g of i.a / ha] Activity (%) against Polygonum convolvulus A1-67 4 10 pendimetalin 100 0 A1-67 + 4 + 100 30 (E ^C = 10, Δ = 20)
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pendimetalin
[218] Table 5-79: Field
Active compound Dosage[g of i.a / ha] Activity (%) againstVeronica hederifolia A1-67 25 75 bromoxynil 210 5 A1-67 + bromoxynil 25 +210 100 (E ^C = 76, Δ = 24)
[219] Table 5-80: Field
Active compound Dosage[g of i.a / ha] Activity (%) againstSetaria viridis A1-67 25 65 MCPA 280 0 A1-67 + MCPA 25 +280 83 (E ^C = 65, Δ = 18)
[220] Table 5-81: Greenhouse
Active compound Dosage[g of i.a / ha] Activity (%) againstCentaurea cyanis A1-69 4 65 isoproturon 100 0 A1 -69 + isoproturon 4 + 100 85 (E ^C = 65, Δ = 20)
[221] Table 5-82: Greenhouse
Active compound Dosage[g of i.a / ha] Activity (%) againstPapaver rhoeas A1-69 4 10 isoproturon 200 40 A1 -69 + isoproturon 4 + 200 80 (E ^C = 46, Δ = 34)
[222] Table 5-83: Greenhouse
Active compound Dosage[g of i.a / ha] Activity (%) againstPapaver rhoeas A1-69 4 10
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isoproturon 200 40 A1 -69 + isoproturon 4 + 200 80 (E ^C = 46, Δ = 34)
[223] Table 5-84: Greenhouse
Active compound Dosage[g of i.a / ha] Activity (%) against Polygonum convolvulus A1-69 4 0 isoproturon 200 0 A1-69 +isoproturon 4 + 200 30 (E ^C = 0, Δ = 30)
[224] Table 5-85: Field
Active compound Dosage[g of i.a / ha] Activity (%) againstEuphorbia heterophylla A1-69 25 20 atrazine 1000 49 A1 -69 + atrazine 25 +1000 89 (E ^C = 59, Δ = 30)
[225] Table 5-86: Greenhouse
Active compound Dosage[g of i.a / ha] Activity (%) againstPapaver rhoeas A1-74 3 30 pinoxaden 10 0 A1-74 + pinoxaden 3 + 10 60 (E ^C = 30, Δ = 30)
[226] Table 5-87: Greenhouse
Active compound Dosage[g of i.a / ha] Activity (%) againstPapaver rhoeas A1-74 3 40 pinoxaden 10 50 A1-74 + pinoxaden 3 + 10 90 (E ^C = 70, Δ = 20)
[227] Table 5-88: Greenhouse
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Active compound Dosage[g of i.a / ha] Activity (%) against Polygonum convolvulus A1-74 3 0 pinoxaden 10 0 A1-74 + pinoxaden 3 + 10 30 (E ^C = 0, Δ = 30)
[228] Table 5-89: Greenhouse
Active compound Dosage[g of i.a / ha] Activity (%) againstVeronica hederifolia A1-74 3 40 pinoxaden 10 20 A1-74 + pinoxaden 3 + 10 60 (E ^C = 52, Δ = 8)
[229] Table 5-90: Greenhouse
Active compound Dosage[g of i.a / ha] Activity (%) againstHairy bidens A1-79 2 20 imazamox 1 10 A1-79 + imazamox 2 + 1 55 (E ^C = 28, Δ = 27)
[230] Table 5-91: Greenhouse
Active compound Dosage[g of i.a / ha] Activity (%) againstAmbrosia artemisiifolia A1-79 2 30 imazamox 2 10 A1-79 + imazamox 2 + 2 70 (E ^C = 37, Δ = 33)
[231] Table 5-92: Field
Active compound Dosage[g of i.a / ha] Activity (%) againstGalium aparine A1-79 25 70 bromoxynil 210 25
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A1-79 + bromoxynil 25 +210 90 (EC = 78, Δ = 12)
[232] Table 5-93: Greenhouse
Active compound Dosage[g of i.a / ha] Activity (%) againstAmbrosia artemisiifolia A1-80 1 25 diflufenzopyr 25 50 A1-80 +diflufenzopyr 1 + 25 85 (EC = 63, Δ = 23)
[233] Table 5-94: Greenhouse
Active compound Dosage[g of i.a / ha] Activity (%) against Brachiaria platyphylla A1-81 1 10 dicamba 12.5 0 A1-81 + dicamba 1 + 12.5 40 (E ^C = 10, Δ = 30)
[234] Table 5-95: Greenhouse
Active compound Dosage[g of i.a / ha] Activity (%) againstEchinochloa crus-galli A1-81 1 10 dicamba 12.5 0 A1-81 + dicamba 1 + 12.5 40 (E ^C = 10, Δ = 30)
[235] Table 5-96: Greenhouse
Active compound Dosage[g of i.a / ha] Activity (%)againstHairy bidens A1-83 1 35 thiencarbazone-methyl 0.5 40 A1-83 + tiencarbazonamethyl 1 + 0.5 75 (E ^C = 61, Δ = 14)
[236] Table 5-97: Greenhouse
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Active compound Dosage[g of i.a / ha] Activity (%)againstBrachiaria platyphylla A1-83 0.5 0 thiencarbazone-methyl 0.5 75 A1-83 + tiencarbazonamethyl 0.5 + 0.5 85 (E ^C = 75, Δ = 10)
[237] Table 5-98: Greenhouse
Active compound Dosage[g of i.a / ha] Activity (%) againstPharbitis purpurea A1-84 2 30 imazamox 1 15 A1-84 + imazamox 2 + 1 70 (E ^C = 41, Δ = 30)
[238] Table 5-99: Greenhouse
Active compound Dosage[g of i.a / ha] Activity (%) againstXanthium strumarium A1-84 1 10 imazamox 1 0 A1-84 + imazamox 1 + 1 40 (E ^C = 10, Δ = 30)
[239] Table 5-100: Greenhouse
Active compound Dosage[g of i.a / ha] Activity (%) againstAmbrosia artemisiifolia A1-85 1 50 imazamox 1 0 A1-85 + imazamox 1 + 1 70 (E ^C = 50, Δ = 20)
[240] Table 5-101: Greenhouse
Active compound Dosage[g of i.a / ha] Activity (%) againstXanthium strumarium
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A1-85 1 25 imazamox 1 10 A1-85 + imazamox 1 + 1 50 (E ^C = 33, Δ = 18)
[241] Table 5-102: Greenhouse
Active compound Dosage[g of i.a / ha] Activity (%) againstAmbrosia artemisiifolia A2-4 1 40 imazamox 2 0 A2-4 + imazamox 1 + 2 60 (E ^C = 40, Δ = 20)
[242] Table 5-103: Greenhouse
Active compound Dosage[g of i.a / ha] Activity (%) againstXanthium strumarium A2-4 2 10 imazamox 2 0 A2-4 + imazamox 2 + 2 35 (E ^C = 10, Δ = 25)
[243] Table 5-104: Field
Active compound Dosage[g of i.a / ha] Activity (%) againstEuphorbia heterophylla A2-4 25 50 atrazine 1000 55 A2-4 + atrazine 25 +1000 93 (E ^C = 78, Δ = 16)
[244] Table 5-105: Greenhouse
Active compound Dosage[g of i.a / ha] Activity (%) againstBrachiaria platyphylla A2-9 1 0 dicamba 12.5 0 A2-4 + imazamox 1 + 12.5 15 (E ^C = 0, Δ = 15)
[245] Table 5-106: Greenhouse
Petition 870190063270, of 07/05/2019, p. 72/78
62/64
Active compound Dosage[g of i.a / ha] Activity (%) against Digitaria sanguinalis A2-9 2 65 dicamba 12.5 0 A2-9 + dicamba 2 + 12.5 85 (E ^C = 65, Δ = 20)
[246] Table 5-108: Greenhouse
Active compound Dosage[g of i.a / ha] Activity (%) againstEchinochloa crus-galli A2-9 1 0 dicamba 12.5 0 A2-9 + dicamba 1 + 12.5 15 (E ^C = 0, Δ = 15)
[247] Table 5-109: Greenhouse
Active compound Dosage[g of i.a / ha] Activity (%) againstBrachiaria platyphylla A2-10 2 0 lenacil 4 0 A2-10 + lenacil 2 + 4 25 (E ^C = 0, Δ = 25)
[248] Table 5-110: Greenhouse
Active compound Dosage[g of i.a / ha] Activity (%) againstBrachiaria platyphylla A2-10 1 35 lenacil 4 0 A2-10 + lenacil 1 + 4 65 (E ^C = 35, Δ = 30)
[249] Table 5-111: Greenhouse
Active compound Dosage[g of i.a / ha] Activity (%) againstHairy bidens A2-10 2 50 lenacil 4 0 A2-10 + lenacil 2 + 4 80 (E ^C = 50, Δ = 30)
[250] Table 5-112: Greenhouse
Petition 870190063270, of 07/05/2019, p. 73/78
63/64
Active compound Dosage[g of i.a / ha] Activity (%) againstSetaria viridis A3-7 2 0 diflufenzopyr 12.5 50 A3-7 +diflufenzopyr 2 + 12.5 70 (E ^C = 50, Δ = 20)
[251] Table 5-113: Greenhouse
Compoundactive Dosage[g of i.a / ha] Activity (%) againstBrachiaria platyphylla A4-2 1 0 diflufenzopyr 25 60 A4-2 +diflufenzopyr 1 + 25 75 (E ^C = 60, Δ = 15)
[252] Table 5-114: Field
Active compound Dosage[g of i.a / ha] Activity (%) againstStellaria media A4-2 25 63 bromoxynil 210 10 A4-2 + bromoxynil 25 +210 90 (E ^C = 67, Δ = 23)
[253] Table 5-115: Greenhouse
Active compound Dosage[g of i.a / ha] Activity (%) againstEchinochloa crus-galli A4-7 3 50 dicamba 12.5 0 A4-7 + dicamba 3 + 12.5 65 (E ^C = 50, Δ = 15)
[254] Table 5-116: Field
Active compound Dosage[g of i.a / ha] Activity (%) againstStellaria media A4-7 25 60
Petition 870190063270, of 07/05/2019, p. 74/78
64/64
bromoxynil 210 5 A4-7 + bromoxynil 25 +210 88 (EC = 62, Δ = 26)
Petition 870190063270, of 07/05/2019, p. 75/78

权利要求:
Claims (6)
[1]
1. Herbicidal composition characterized by comprising (A) an N- (tetrazol-4-yl) - or N- (triazol-3-yl) arylcarboxamides of formula (I) or their salts
R (I), where the symbols and indices are each defined as follows:
A represents N or CY,
B represents N or CH,
X represents halogen, (C1-C2) -alkyl, methoxy, methoxymethyl or SO2CH3,
Y represents hydrogen, (C1-C2) -alkyl, O (C1-C2) -alkyl, S (O) n- (C1C6) -alkyl, CH2OMe, OCH2-c-Pr, O (CH2) 3OMe, pyrazolyl or dihydrooxazolyl ,
Z represents methyl, bromine, difluoromethyl, trifluoromethyl or S (O) n- (C1C2) -alkyl,
W represents hydrogen or methyl,
R represents (C1-C3) -alkyl,
N represents 0, 1 or 2, (B) a herbicide (component B) selected from the group consisting of aclonifen, atrazine, bicyclopyrone, bromoxynil, dicamba, diflufenicon, diflufenzopyr, dimethenamide-P, phenoxaprope-P-ethyl, flufenacet, foramsulfuron, ammonium glufosinate, glyphosate, glyphosate-potassium, indaziflam, isoproturon, imazamox, lenacil, MCPA, mesotrione, metribuzin, nicosulfuron, pendimetalin, pinoxaden, rimsulfuron, tiencarbazone-methyl and toprazone.
Petition 870190063270, of 07/05/2019, p. 76/78
[2]
2/2
2. Herbicidal composition according to claim 1, characterized by
Representing CY,
B represents N,
X represents chlorine, methyl, ethyl or methoxy,
Y represents hydrogen, CH2OMe, 4,5-dihydro-1,2-oxazol-3-yl, pyrazol-1-yl, OMe, OEt, OCH2-c-Pr, SO2CH3, S (O) CHa, SCH3, SO2Et, S (O) Et or SEt,
Z represents trifluoromethyl or bromine,
W represents hydrogen, and
R represents methyl or propyl.
[3]
Herbicidal composition according to claim 1 or 2, characterized in that it further comprises, as component C, a protecting agent of the group consisting of benoxacor, cloquintocete-mexilo, cyprosulfamide, diclormide, fenclorim, fenclorazol, furilazol, isoxadifen- ethyl, mefenpir-diethyl, 4- (dichloroacetyl) -1-oxa-4-azaspiro [4,5] decane, 2,2,5-trimethyl-3 (decloroacetyl) -1,3-oxazolidine.
[4]
4. A method for combating weeds in crops, characterized in that a herbicidally effective amount of a herbicidal composition, as defined in claim 1 or 2, is applied to harmful plants, plants, plant seeds or in the area where the plants grow .
[5]
Method according to claim 4, characterized in that the plants belong to the group of sugar cane, corn, wheat, rye, barley, oats, rice, sorghum, cotton and soy.
[6]
Method according to claim 4 or 5, characterized in that the plants are genetically modified.

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法律状态:
2018-06-12| B06F| Objections, documents and/or translations needed after an examination request according art. 34 industrial property law|

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2019-02-19| B07A| Technical examination (opinion): publication of technical examination (opinion)|

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2019-03-26| B07B| Technical examination (opinion): publication cancelled|Free format text: ANULADA A PUBLICACAO CODIGO 7.1 NA RPI NO 2511 DE 19/02/2019 POR TER SIDO INDEVIDA. |

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2019-04-09| B07A| Technical examination (opinion): publication of technical examination (opinion)|

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2019-08-13| B09A| Decision: intention to grant|

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2019-09-03| B16A| Patent or certificate of addition of invention granted|Free format text: PRAZO DE VALIDADE: 20 (VINTE) ANOS CONTADOS A PARTIR DE 22/05/2013, OBSERVADAS AS CONDICOES LEGAIS. (CO) 20 (VINTE) ANOS CONTADOS A PARTIR DE 22/05/2013, OBSERVADAS AS CONDICOES LEGAIS |

优先权:

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申请号 | 申请日 | 专利标题

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EP12169189.3|2012-05-24|

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EP12169189|2012-05-24|

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PCT/EP2013/060468|WO2013174845A1|2012-05-24|2013-05-22|Herbicidal compositions comprising n-- or n-arylcarboxamides|

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