IL45060A - Herbicidal compositions containing a dinitroaniline derivative and a carbamate thiolcarbamate or dithiocarbamate and/or a pyridazone derivative - Google Patents
Herbicidal compositions containing a dinitroaniline derivative and a carbamate thiolcarbamate or dithiocarbamate and/or a pyridazone derivativeInfo
- Publication number
- IL45060A IL45060A IL45060A IL4506074A IL45060A IL 45060 A IL45060 A IL 45060A IL 45060 A IL45060 A IL 45060A IL 4506074 A IL4506074 A IL 4506074A IL 45060 A IL45060 A IL 45060A
- Authority
- IL
- Israel
- Prior art keywords
- spp
- per hectare
- substituted
- halogen
- dinitro
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 28
- 230000002363 herbicidal effect Effects 0.000 title claims description 11
- 239000012990 dithiocarbamate Substances 0.000 title description 2
- WLRLSNCGSKQYFH-UHFFFAOYSA-N carbamic acid thiophen-2-ylcarbamic acid Chemical compound S1C(=CC=C1)NC(=O)O.C(N)(O)=O WLRLSNCGSKQYFH-UHFFFAOYSA-N 0.000 title 1
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 title 1
- LZGUHMNOBNWABZ-UHFFFAOYSA-N n-nitro-n-phenylnitramide Chemical class [O-][N+](=O)N([N+]([O-])=O)C1=CC=CC=C1 LZGUHMNOBNWABZ-UHFFFAOYSA-N 0.000 title 1
- 229910052736 halogen Inorganic materials 0.000 claims description 26
- 125000005843 halogen group Chemical group 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- -1 tetrahydrofurfuryl Chemical group 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 14
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 125000001188 haloalkyl group Chemical group 0.000 claims description 6
- 239000004009 herbicide Substances 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
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- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
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- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 229910000148 ammonium phosphate Inorganic materials 0.000 description 1
- 235000019289 ammonium phosphates Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
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- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
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- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- SLFVYFOEHHLHDW-UHFFFAOYSA-N n-(trifluoromethyl)aniline Chemical compound FC(F)(F)NC1=CC=CC=C1 SLFVYFOEHHLHDW-UHFFFAOYSA-N 0.000 description 1
- HLLYDGVOMRCOFR-UHFFFAOYSA-N n-butyl-n-ethyl-2,6-dinitro-4-(trifluoromethyl)aniline;2,6-dinitro-n,n-dipropyl-4-(trifluoromethyl)aniline Chemical compound CCCCN(CC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O.CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O HLLYDGVOMRCOFR-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920000847 nonoxynol Polymers 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
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- 238000002360 preparation method Methods 0.000 description 1
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- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
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Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03H—HOLOGRAPHIC PROCESSES OR APPARATUS
- G03H1/00—Holographic processes or apparatus using light, infrared or ultraviolet waves for obtaining holograms or for obtaining an image from them; Details peculiar thereto
- G03H1/04—Processes or apparatus for producing holograms
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Herbicidal compositions containing a dinitroanilne derivative and a carbamate, thiolcarbamate or dit iocarbaiaate and/or a pyridatsoa© deriative BASF AEfIBHOESILiSCHAF 0/ 3162 The present invention relates to herbicides, especially selective herbicides.
It is known to use substituted dinitroanilines , carbamates, dithiocarbamates and pyridazones as herbicidal active ingredients . However, their action is not always satisfactory. I We have now found that herbicides comprising a composition of a) a compound of the formula 02 where X denotes lower alkyl, haloalkyl, alkylsul onyl, methoxy or aminosulfonyl, R^" denotes tetrahydrofurfuryl , cyclopropyl, cyclopropylmethyl , lower alkyl which may be substituted by halogen or alkoxy, alkenyl which may be substituted by halogen or alkoxy, or alkynyl which may be substituted by halogen or alkoxy, and R denotes alkoxy- alkyl, propionomethylamide, lower alkyl which may be substituted by halogen, alkenyl which may be substituted by halogen or alkynyl which may be substituted by halogen, and b) a compound of the formula where R denotes alkyl, alkenyl, alkynyl, bicycloalkyl, tricycloalkyl, phenyl which may be substituted by halogen or alkyl, or cycloalkyl which may be substituted by halogen or alkyl, R1 denotes hydrogen or an ; alkyl radical having a maximum of 4 carbon atoms, R2 denotes alkyl which may be substituted by halogen or alkoxy, alkenyl which may be substituted by halogen or alkoxy, alkynyl which may be substituted by halogen or alkoxy, phenyl which may be substituted by halogen, haloalkyl, alkyl or alkoxy, benzyl which may be substituted by halogen, haloalkyl, alkyl or alkoxy, 3-methoxycarbonylaminophenyl or the radical r, and X denotes oxy- gen or sulfur, with the proviso that R, R1 land R may not simultaneously be alkyl, and optionally ) a compound of the formula where X denotes amino or o^-hydroxy-B,S,B-trichloroethyl- amino and Y denotes chloro or bromo, 0 have a good herbicidal action.
The compositions may contain one or more compounds of the formula a and one or more compounds from groups b and optionally also one or more compounds from group c. o.z. 29,96 The ratio of the active ingredients to each other maybe varied at will; it is however preferred to use from to 10 parts by weight of a compound of the formula a to from 0.1 to 10 parts by weight of compounds of the formulas b and c. Application rates range from from 0.1 to 15, preferably from 0.1 to 5, kg per hectare of active ingredient.
The agents of the invention are selective in Beta spp., Alium cepa, Pisum sativum, Gladiolus spp., Soja hispida, Gos-sypium hirsutum, Phaseolus vulgaris, Arachis hypogaea, etc.
Application may be effected for instance in the form of directly sprayable solutions, powders, suspensions, dispersions, emulsions, oil dispersions, pastes, dusts, or granules by spraying, atomizing, dusting, broadcasting or watering. The form of application depends entirely on the purpose for which the agents are being used; in any case it should ensure a fine distribution of the active ingredient.
For the preparation of solutions, emulsions, pastes and oil dispersions to be sprayed direct, mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, further coal-tar oils and oils of vegetable or mineral origin, aliphatic, cyclic and aromatic hydrocarbons such as benzene, toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes, methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexan-one, chlorobenzene, isophorone, etc., and strongly polar solvents such as dimethyl ormamide, dimethyl sulfoxide, N-methyl pyrrolidone, water, etc. are suitable.
Aqueous formulations may be prepared from emulsion con-centrates, pastes, oil dispersions or wettable powders by O.Z. 29,964 adding water. To prepare emulsions, pastes and oil dispersions the ingredients as such or dissolved in an oil or0£&-vent may be homogenized in water by means of wetting or dispersing agents, adherents or emulsifiers. Concentrates which are suitable for dilution with water may be prepared from active ingredient, wetting agent, adherent, emulsifying or dispersing agent and possibly solvent or oil.
Examples of surfactants are: alkali metal, alkaline earth metal and ammonium salts of ligninsulfonic acid, naph-thalenesulfonic acid, phenolsulfonic acids, alkylaryl sulfonates, alkyl sulfates, and alkyl sulfonates, alkali metal and alkaline earth metal salts of dibutylnaphthalenesulfonic acid, lauryl ether sulfate, fatty alcohol sulfates, alkali metal and alkaline earth metal salts of fatty acids, salts of sulfated hexadecanols, heptadecanols, and octadecanols, salts of sulfated fatty alcohol glycol ether, condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, poly-oxyethylene octylphenol ethers, ethoxylated isooctylphenol, ethoxylated octylphenol and ethoxylated nonylphenol, alkyl-phenol polyglycol ethers, tributylphenyl polyglycol ethers, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxyproylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lig-nin, sulfite waste liquors and methyl cellulose.
Powders, broadcasting agents and dusts may be prepared by mixing or grinding the active ingredients with a solid carrier.
O.Z. 29, 964 solid carriers. Examples of solid carriers are mineral earths such as silica gel, silicic acid, silicates, talc, kaolin, Attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, and ureas, and vegetable products such as grain flours, bark meal, wood meal, and nutshell meal, cellulosic powders, etc.
The formulations contain from 0. 1 to 95» and preferably from 0.5 to 90, by weight of active ingredient.
There may be added (if desired, immediately before use) to the compositions or individual active ingredients oils of various types, herbicides, fungicides, nematocides, insecticides, bactericides, trace elements, fertilizers, antifoams (e.g. silicones), growth regulators, antidotes and other herbicidally effective compounds.
These agents may be added to the herbicides according to the invention in a ratio by weight of from 1 : 10 to 10 : 1 . The same applies to oils, fungicides, nematocides, insecticides, bactericides, antidotes and growth regulators.
The agents may be used once or several times before or after planting, before sowing, preemergence, postemergence or during emergence of the crop plants or unwanted plants. The amount used varies and depends in essence on the effect desired.
The agents have a strong herbicidal action and may therefore be used as weedkillers or for controlling the growth of unwanted plants. Whether the agents are used as total or selective agents depends in essence on the amount of ingredient used per unit area. f By weeds and unwanted plant growth are meant all mono-cotyledonous and dicotyledonous plants which grow in loci where they are not desired.
The agents according to the invention may therefore be used for controlling for instance Gramineae, such as Cynodon spp. Dactylis spp.
Digitaria spp. Avena spp.
Echinochloa spp. Bromus spp.
Setaria spp. Uniola spp.
Panicum spp. Poa spp.
Alopecurus spp. Leptochloa spp.
Lolium spp. Brachiaria spp.
Sorghum spp. Eleusine spp.
Agropyron spp. Cenchrus spp.
Phalaris spp. Eragrostis spp.
Apera spp. Phragmites communis etc . ; Cyperaceae, such as Carex spp. Eleocharis spp.
Cyper s spp. Scirpus spp. etc . ; dicotyledonous weeds, such as Malvaceae, e.g.
Abutilon theoprasti Hibiscus spp.
Sida spp. Malva spp.
O.z. 29,96 Compositae, such as Ambrosia spp. Centaurea spp.
Lactuca spp. Tussilago spp.
Senecio spp. Lapsana communis Sonchus spp. Tagetes spp.
Xanthium spp. Erigeron spp.
Iva spp. Anthemis spp.
Galinsoga spp. Matricaria spp.
Taraxacum spp. Artemisia spp.
Chrysanthemum spp. Bidens spp.
Cirisum spp. etc . ; Convolvulaceae, such as Convoluvulus spp. Cuscuta spp.
Ipomoea spp. Jaquemontia tamnifolia etc . ; Cruciferae, such as Barbarea vulgaris Arabidopsis thaliana Brassica spp. Descurainia spp.
Capsella spp. Draba spp.
Sisymbrium spp. Coronopus didymus Thlaspi spp. Lepidium spp.
Sinapis arvensis Raphanus spp. etc.; Geranicaceae, such as Erodium spp. Geranium spp. etc . j Portulacaceae, such as Portulaca spp. etc . ; Primulaceae, such as Anagallis arvensis Lysimachia spp. etc . j Ο.Ζ. 29,9β½ Rubiaceae, such as Richardia spp. Diodia spp.
Galium spp. etc . ; Scrophularlaceae, such as Linaria spp. Digitalis spp.
Veronica spp. etc . ; Solanaceae, such as Physalis spp. Nicandra spp.
Solanum spp. Datura spp. etc . j Urticaceae, such as Urtica spp. etc . j Violaceae, such as Viola spp. etc . ; Zygophyllaceae, such as Tribulus terrestis etc . ; Euphorbiaceae, such as Mercurialis annua Euphorbia spp.
Umbelliferae, such as Daucus earota Ammi majus Aethusa cynapium etc . ; Commelinaeae, such as Commelina spp. etc . ; Labiatae, such as Lamium spp. Galeopsis spp. etc . ; Leguminosae, such as edicago spp. Sesbania exaltata Trifollum spp. Cassia spp.
Vicia spp. Lathyrus spp. etc . ; O.z. 29,96 Plantaginaceae, such as Plantago spp. etc. ; Polygonaceae, such as Polygonum spp. Pagopyrura spp.
Rumex spp. etc . ; Aizoaceae, such as Mollugo vertlcillata etc .
Amaranthaceae, such as Amaranthus spp. etc . ; Boraginaceae, such as Amslnckia spp. Anchusa spp.
Myostis spp. Lithospermum spp. etc . ; Caryophyllaceae, such as Stellaria spp. Silene spp.
Spergula spp. Cerastium spp.
Saponaria spp. Agrosterama githago Scleranthus annuus etc . ; Chenopodiaceae, such as Chenopodium spp. Atriplex spp.
Kochia spp. Monolepsis nuttaliana Salsola Kali etc. j Lythraceae, such as Cuphea spp. etc . j Oxalidaceae, such as Oxalis spp. etc. ; Ranunculaceae, such as Ranunculus spp. Adonis spp.
Delphinium spp. etc. ; o.z. 29,96 Papaveraceae, such as Papaver spp. Pumaria officinalis etc . ; Onagraceae, such as Jussiacea spp. etc . ; Rosaceae, such as Alchemillia spp. Potentilla spp. etc . ; Potamogetonaceae, such as Potamogeton spp. etc . ; Najadaceae, such as Najas spp. etc . j Marsileaceae, such as Marsilea quadrifolia etc .
In the greenhouse and in the open, the action of compositions of the following compounds on the abovementioned plants was investigated: N-ethyl-N-butyl-2,6-dinitro-4--trifluoromethylaniline N,N-di-(n-propyl)-2,6-dinitro-4-trifluoromethylaniline N-propyl-N-S-chloroethyl-2,6-dinitro-4-trifluoromethylaniline N-allyl-N-S-chloroethyl-2,6-dinitro-4-trifluoromethylaniline N-ethyl-N-B-chloroethyl-2,6-dinitro-4-tri luoromethylaniline N-ethyl-N-fi-bromoethyl-2,6-dinitro-4-trifluoromethylaniline N-propyl-N-13-bromoethyl-2,6-dinitro-4-trifluoromethylaniline N-J3-methoxyethyl-N-13-chloroethyl-2,6-dinitro-4-trifluoromethylaniline N-isopropyl-N-propargyl-2,6-dinitro-4-trifluoromethylaniline N-propyl-N-allyl-2,6-dinitro-4-trifluoromethylaniline N-propyi-N-propargyl-2,6-dinitro-4-trifluoromethylaniline N,N-bis-(B-chloroethyl) -2,6-dinitro-4-trifluoromethylaniline N,N-bis-(B-methoxyethyl)-2,6-dinitro-4-trifluoromethylaniline N-propyl-N-cyclopropyl-2,6-dinitro-4-trifluoromethylanilin^ N-propyl-N-tetrahydrofurfuryl-2,6-dinitro-4-trifluoromethyl-aniline N-ethyl-N-tetrahydrofurfuryl-2,0-dinitro-4-trifluoromethyl-aniline N-propyl-N-cyclopropylmethyl-2,6-dinitro-4-trifluoromethyl-> aniline N-propyl-N-allyl-2,6-dinitro-4-methylsulfonylaniline Ν,Ν-bis- (n-propyl) -2,6-dinitro-4-methylsulfonylaniline Ν,Ν-bis- (n-propyl) -2,6-dinitro-4-aminosulfonylaniline Ν,Ν-bis- (n-propyl) -2,6-dinitro-4-methylaniline Ν,Ν-bis-(sec-butyl)-2,6-dinitro-4-tert-butylaniline Ν,Ν-bis-(n-propyl)-2,6-dinitro-4-isopropylaniline N-methyl-N-fl-chloroethyl-2,6-dinitro-4-methylaniline Ν,Ν-bis- (n-propyl) -2,6-dinitro-4-methoxyaniline Ν,Ν-bis- (β-chloroe hyl)-2,6-dinitro-4-methylaniline 2,j5-dichloroallyl N,N-diisopropylthiolcarbamate 2-(2,6-dinitro-4-toluidine)-N-propionomethylamide 2,3,3-trichloroallyl N,N-diisopropylthiolcarbamate n-propyl N-ethyl-N-butylthiolcarbamate ethyl N,N-di- (n-propyl)-thiolcarbamate n-propyl N,N-di- (n-propyl)-thiolcarbamate tert-butyl N,N-di- (n-propyl )-thiolcarbamate ethyl N,N-diisobutylthiolcarbamate ethyl N,N-di- (n-butyl) -thiolcarbamate butyl N,N-diethylthiolcarbamate 2-chloroallyl N,N-diethyldithiocarbamate ethyl N-ethyl-N-cyclohexylthiolcarbamate O.Z. 29,9 4 ethyl N-bicyclo- (2, 2, 1 ) -heptyl-N-ethylthlolcarbaraate ethyl N-l- or -2-bicyclo- (3,3, 0)-octyl-N-ethylthiolcarb^j|jfbe p-chlorobenzyl N,N-diethylthiolcarbamate ethyl N-bicyclo- ( 2, , 1 ) -heptyl-N-e h ldithiocarbamate isopropyl N-l- or -2-bicyclo- (3,3 , 0) -N-ethylthiolcarbamate ethyl N-propargyl-N-cyclohexylthiolcarbamate ethyl N-ethyl-N-o-methylcyclohexylthiolcarbamate isopropyl N-phenylcarbamate isopropyl N-ra-chlorophenylcarbamate butyn-l-yl-3 N-m-chlorophenylcarbamate 4-chlorobutyn-2-yl-l N-m-chlorophenylcarbamate methyl N-3,4-dichlorophenylcarbamate 3,4-dichlorobenzyl N-methylcarbamate 2, 6-di-(tert-butyl)-p-tolyl N-methylcarbamate 0- (N-phenylcarbamoyl ) -propanonoxime 3-methoxycarbonylaminophenyl-N- ( ' -methylphenyl ) -carbamate 1 -phenyl-4-amino-5-chloropyridazone- (6 ) l-phenyl-4-oG-hydroxy-B, -3, i3-trichloroethylamino-5-bromo-pyridazone- (6 ) .
These investigations showed that compositions of the abovementioned compounds have an action corresponding to that of the compositions in Examples 1 to 10.
EXAMPLE 1 An agricultural plot was treated with the following amounts of the following individual active ingredients and compositions thereof as granules: I N,N-di-n-propyl-2, 6-dinitro-4-trifluoromethylaniline, 0. 15, 0.25, 0.5, 1 , 1 .5 and 1 .8 kg per hectare; II N-n-propyl-N-B-chloroethyl-2, 6-dinitro-4-trifluoro- methylaniline, 0. 15, 0.25, 0.5, 1 , 1 .5 and 1 .8 kg per hectare; . . , III N-allyl-N-B-chloroethyl-2,6-dinitro-4~trifluoromethyl- aniline, 0.15, 0.25, 0.5, 1, 1.5 and 1.8 kg per heo ¾re; IV N,N-di-n-propyl-2,6-dinitro-4-aminosulfonylanlllne, 0.15, 0.25, 0.5, 1, 1.5 and 1.8. kg per hectare; V 2,3-dichloroallyl N,N-diisopropylthiolcarbamate, 0.15, 0.25, 0.5, 1, 1.5 and 1.8 kg per hectare; VI 2,3,3-trichloroallyl N,N-diisopropylthiolcarbamate, 0.15, 0.25, 0.5, 1, 1.5 and 1.8 kg per hectare; II l-phenyl-4-amino-5-chloropyrldazone- (6) , 0.15, 0.25, 0.5, 1, 1.5 and 1.8 kg per hectare; I + VI + VII: 1.5+0.15+0.25, 0.25+0.25+1.5, 0.15+1.5+0.15, 0.5+0.5+0.5, 0.25+0.25+0.5, 0.25+0.5+0.25, and Ο.5+Ο.25+Ο.25 kg per hectare; II+VI + VII: I.5+O.15+O.25, O.25+O.25+I.5, O.15+I.5+O.I5, 0.5+0.5+0.5, Ο.25+Ο.25+Ο.5, Ο.25+Ο.5+Ο.25, and Ο.5+Ο.25+Ο.25 kg per hectare; III+VI + VII: I.5+O.15+O.25, O.25+O.25+I.5, O.15+I.5+O.I5, 0.5+0.5+0.5, Ο.25+Ο.25+Ο.5, Ο.25+Ο.5+Ο.25, and Ο.5+Ο.25+Ο.25 kg per hectare; IV + VI + VII: 1.5+0.15+0.25, 0.25+0.25+1.5, 0.15+1.5+0.15, 0.5+0.5+0.5, Ο.25+Ο.25+Ο.5, Ο.25+Ο.5+Ο.25, and Ο.5+Ο.25+Ο.25 kg per hectare; I + V + VII: I.5+O.15+O.25, O.25+O.25+I.5, O.I5+I.5+O.15, Ο.5+Ο.5+Ο.5, Ο.25+Ο.25+Ο.5, Ο.25+Ο.5+Ο.25, and Ο.5+Ο.25+Ο.25 kg per hectare; II + V + VII: I.5+O.I5+O.25, Ο.25+Ο.25+I.5* 0.15+I. +0.15, Ο.5+Ο.5+Ο.5, Ο.25+Ο.25+Ο.5, Ο.25+Ο.5+Ο.25, and Ο.5+Ο.25+Ο.25 kg per hectare.
Seeds of various plants were then sown in the soil pre-pared in this manner.
O.Z. 29,964 After 3 to weeks it was ascertained that the compo itions had a better herbicidal action than their comport^ ombined with the same good crop plant compatibility.
The results are given below: Active ingredient I kg/ha 0. 15 0.25 0.5 1 1 .5 1 .8 Crop plant : Beta vulgaris 0 0 0 0 0 5 Unwanted plants : Alopecurus myosuroides 3 23 41 63 75 87 Avena fatua 7 18 54 51 73 78 Digitaria sanguinalis 16 25 45 70 80 100 Echinochloa crus-galli 15 32 50 70 30 88 Setaria faberii 20 37 45 65 90 100 Stellaria media 2 5 7 16 20 25 Active ingredient III Beta vulgaris 0 0 0 0 0 0 Alopecurus myosuroides 8 17 55 55 71 83 Avena fatua 7 14 26 44 63 71 Digitaria sanguinalis 15 25 45 70 76 80 Echinochloa crus-galli 15 25 40 70 80 87 Setaria faberii 10 20 35 50 55 65 Stellaria media 2 8 17 20 24 Active ingredient V kg/ha 0. 15 0.25 1 .5 1 .8 Crop plant: Beta vulgaris 0 0 0 0 0 0 Unwanted plants : Alopecurus myosuroldes 7 1 1 26 58 85 94 Avena fatua 6 10 20 50 63 78 Digitaria sanguinalis 0 0 3 9 12 15 Echlnochloa crus-galli 0 0 6 16 19 21 Setaria faberii 0 2 5 10 15 20 Stellaria media 2 6 7 13 15 19 Active ingredient VII Beta vulgaris 0 0 0 0 0 0 Alopecurus myosuroides 0 0 2 15 19 20 Avena fatua 0 0 2 6 15 19 Digitaria sanguinalis 0 2 5 10 25 30 Echinochloa crus-galli 0 5 10 20 25 29 Setaria faberii 0 10 20 30 35 35 Stellaria media 6 10 20 5 60 75 0 = no damage 100 = complete destruction Active ingredient I + V k /ha 1 .5+ 0. 15+ 0. 15+ 0. 15+ 0. 15+ 1 .5+ O. 15 1 .5 0. 15 Crop plant: Beta vulgaris 0 0 0 Unwanted plants : Alopecurus myosuroides 100 69 100 Avena fatua 100 65 100 Digitaria sanguinalis 100 74 63 Echinochloa crus-galli 100 80 88 Setaria faberil 100 34 Si Stellaria media 64 100 60 Active ingredient II + Beta vulgaris 0 0 0 Alopecurus myosuroides 100 75 100 Avena fatua 100 72 100 Digitaria sanguinalis 100 77 70 Echinochloa crus-galli 100 85 8 Setaria faberii 100 95 87 Stellaria media 58 100 63 Active ingredient III Crop plant: Beta vulgaris 0 0 0 Unwanted plants : Alopecurus myosuroides 97 72 100 Avena fatua 95 69 100 Digitaria sanguinalis 100 75 70 Echinochloa crus-galli 100 85 8 Setarla faberil 96 76 73 Stellaria media 68 97 57 Active ingredient I Beta vulgaris 0 0 0 Alopecurus myosuroides 100 65 100 Avena fatua 100 63 100 Digitaria sanguinalis 100 70 60 Echinochloa crus-galli 100 78 35 Setaria faberii 100 83 80 Stellaria media 64 100 5<- Active ingredient II kg /ha' 1 .5+ 0.15+ 0. 15+ 0. 15+ 0. 15+ 1 .5+ 0. 15 1 .5 0.15 Crop plant : Beta vulgaris 0 0 0 Unwanted plants : Alopecurus myosuroides 100 73 100 Avena fatua 100 70 100 Digitaria sanguinalis 100 78 68 I Echinochloa crus-galli 100 85 . 85 Setaria faberii 100 93 85 VO I Stellaria media 55 100 65 Active ingredient TV Beta vulgaris 0 0 0 Alopecurus myosuroides 100 7 100 Avena fatua 100 72 100 Digitaria sanguinalis 100 70 Crj Echinochloa crus-galli 100 84 82 Setaria faberii 100 93 95 Stellaria media 65 92 73 0 = no damage 100 = complete destruction O.Z. 29,9 EXAMPLE 2 In the greenhouse, loamy sandy soil was filled into 8 s and sown with the seeds of various plants. The soil prepared in this manner was then treated with the following amounts of the following individual active ingredients and compositions thereof as dispersions, the dispersions being incorporated into the soil: I N,N-di-n-propyl-2,6-dinitro-4-trifluoromethylaniline, 0.15, 0.25, 0.5, 1, 1.5 and 1.8 kg per hectare; II N-n-propyl-N-B-chloroethyl-2,6-dinitro-4-trifluoro- methylaniline, 0.15, 0.25, 0.5, 1, 1.5 and 1.8 kg per hectare; IV N,N-di-n-propyl-2,6-dinitro- -aminosul onylaniline, 0.15, 0.25, 0.5, 1, 1.5 and 1.8 kg per hectare; VII l-phenyl-4-amino-5-chloropyridazone- (6) , 0.15, 0.25, 0.5, 1, 1.5 and 1.8 kg per hectare; VIII ethyl N-ethyl-N-cyclohexylthiolcarbamate, 0.15, 0.25, 0.5, 1, 1.5 and 1.8 kg per hectare; I + VII + VIII: 1.5+0.15+0.15, 0.15+0.15+1.5, 0.15+1.5+0.15, 0.5+0.5+0.5, 0.5+0.25+0.25, 0.25+0.5+0.25 and 0.25+0.25+0.5 kg per hectare; II + VII + VIII: 1.5+0.15+0.15, 0.15+0.15+1. , 0.15+1. +0.15, 0.5+0.5+0.5, 0.5+0.25+0.25, 0.25+0.5+0.25 and Ο.25+Ο.25+Ο.5 k per hectare; IV+VII + VIII: 1.5+0.15+0.15, 0.15+0.15+1.5, 0.15+1.5+0.15, 0.5+0.5+0.5, Ο.5+Ο.25+Ο.25, Ο.25+Ο.5+Ο.25 and Ο.25+Ο.25+Ο.5 kg per hectare.
After 3 to weeks it was ascertained that the compositions had a better herbidlcal action than their components, combined with the same good crop plant compatibility.
The results are given below: Active ingredient kg/ha 0.15 0.25 0.5 1 1 .5 1.8 Crop plant : Beta vulgaris 0 0 0 0 0 5 Unwanted plants: Alopecurus myosuroides 8 23 41 63 75 87 Avena fatua 7 18 34 51 73 78 Digttaria sanguinalis 16 25 45 70 80 100 Echinochloa crus-galli 15 32 50 70 80 88 Setaria faberii 20 37 46 65 90 100 Stellaria media 2 5 7 16 20 25 Active ingredient IV Beta vulgaris 0 0 0 0 0 5 Alopecurus myosuroides 9 20 36 58 70 80 Avena fatua 10 14 30 48 65 70 Digitaria sanguinalis 15 28 55 84 95 100 Echinochloa crus-galli 20 3 50 76 87 94 Setaria faberii 25 33 58 87 95 100 Stellaria media 3 5 8 15 18 22 O.Z. 29,9 Active ingredient VIII kg/ha 0.15 0.25 0.5 1 1.5 1.8 Crop plant: Beta vulgaris 0 0 0 0 0 0 Unwanted plants : Alopecurus myosuroides 5 10 15 68 80 87 Avena fatua 3 5 10 27 40 46 Digitaria sanguinalis 5 15 32 50 70 75 Echinochloa crus-galli 7 15 25 48 70 78 Setaria faberii 5 12 27 5 67 80 Stellaria media 0 5 12 20 28 40 Active ingredient I + VII kg 'ha 11 ..55++ 0O.. 1155++ 0O.. 1155++ 00..55++ 0 O.. 1155++ 0O.. 1155++ 11 ..55++ 00..55++ 0. 15 1 .5 0. 15 0.5 Crop plant : Beta vulgaris 0 0 0 0 Unwanted plants : Alopecurus myosuroides 100 100 70 100 Avena fatua 100 86 63 80 Digitaria sanguinalis 100 100 8 100 Echinochloa crus-galli 100 100 85 100 Setaria faberii 100 98 96 100 Steliaria media 62 73 98 76 Active ingredient ; II + VII Beta vulgaris 0 0 0 0 Alopecurus myosuroides 100 100 72 96 Avena fatua 98 8 66 80 Digitaria sanguinalis 100 100 92 100 Echinochloa crus-galli 100 100 90 100 Setaria faberii 100 100 95 100 Stellaria media 58 75 97 80 Active ingredient IV + V kg/ha 1.5+ 0.15+ 0.15+ 0 0.15+ 0.15+ 1.5+ 0 O.15 1.5 0.15 0 Crop plant; Beta vulgaris 0 0 0 Unwanted plants : Alopecurus myosuroides 100 100 70 1 Avena fatua 100 87 68 Digitaria sanguinalis 100 100 84 1 Echinochloa crus-galli 100 100 90 1 Setaria faberii 100 100 92 1 Stellaria media 68 73 100 0 = no damage 100 = complete destruction o.z. 29,964 EXAMPLE 3 An agricultural plot was treated with the following ^ amounts of the following individual active ingredients and compositions thereof as granules: I N,N-di-n-propyl-2 , 6-dinitro-4-trifluoromethylaniline, Ο.25, 0. 5 and 1 kg per hectare; II N,N-propyl-N-B-chloroethyl-2, 6-dinitro-4-trifluoro- methylaniline , Ο.25, 0.5 and 1 kg per hectare; V 2 ,3-dichloroallyl N,N-diisopropylthiolcarbamate, Ο.25, 0.5 and 1 kg per hectare; VI 2,3,3-trichloroallyl N,N-diisopropylthiolcarbamate, Ο.25, 0. 5 and 1 kg per hectare; VIII ethyl N-ethyl-N-cyclohexylthiolcarbamate, Ο. 25, 0. 5 and 1 kg per hectare; I + V + VIII: Ο.25+Ο.25+Ο.5, Ο.25+Ο. 5+Ο.25 and 0.5+0.25+ Ο.25 kg per hectare; I + VI + VIII: Ο. 25+Ο.25+Ο.5, Ο.25+Ο. 5+Ο.25 and 0.5+0.25+ Ο.25 kg per hectare; II + V + VIII: Ο.25+Ο.25+Ο.5 , Ο.25+Ο.5+Ο.25 and 0. 5+0.25+ Ο.25 kg per hectare; 11 + VI + VIII: Ο. 25+Ο.25+Ο.5, Ο.25+Ο.5+Ο.25 and 0.5+0.25+ Ο.25 kg per hectare.
Subsequently, seeds of various plants were sown in the soil prepared in this manner.
After 3 to 4 weeks it was ascertained that the compositions had a better herbicldal action than their components, combined with the same good crop plant compatibility.
The results are given below: Active ingredient I kg/ha 0.25 0.5 1 0.2 Crop plant: Beta vulgaris 0 0 0 0 Unwanted plants : Alopecurus myosuroides 3 41 63 20 Ave a fatua 18 34 51 15 Echinochloa crus-galli 32 50 70 30 Setaria faberii 37 46 65 35 Active ingredient VI Beta vulgaris 0 0 0 0 Alopecurus myosuroides 15 30 60 10 Avena fatua 15 25 60 5 Echinochloa crus-galli 5 10 20 15 Setaria faberii 4 7 15 12 Active ingredient I + V + VIII I + VI kg/ha 0.25+ 0.25+ 0.5+ 0.25+ 0. 0.25+ 0.5+ 0.25+ 0.25+ 0. 0.5 0.25 0.25 0.5 0.
Crop plant: Beta vulgaris 0 0 0 0 Unwanted plants : Alopecurus myosuroides 90 96 87 95 ■ Avena fatua 72 78 70 80 Echinochloa crus-galli 95 90 92 97 Setaria faberii 97 90- 96 100 Active ingredient II + VI + VIII Beta vulgaris 0 0 0 Alopecurus myosuroides 90 95 100 Avena fatua 84 79 86 Echinochloa crus-galli 97 92 100 Setaria faberii 98 90 100 0 = no damage 100 = complete destruction i EXAMPLE 4 j An agricultural plot was sown with various seeds. Tfc^ soil prepared in this manner was then treated with the following amounts of the following individual active ingredients and compositions thereof as pastes: I N,N-di-n-propyl-2, 6-dinitro- -trifluromethylaniline, 0.25, 0.5, 0.75 and 1 kg per hectare; II N-n-propyl-N-B-chloroethyl~2, 6-dinitro-4-trifluoro- methylaniline, 0.25, 0.5, 0.75 and 1 kg per hectare; IV N,N-di- (n-propyl ) -2, 6-dinitro-4-aminosulfonylaniline , 0.25, 0.5, 0.75 and 1 kg per hectare; V 2,j5-dichloroallyl N,N-diisopropylthiolcarbamate, 0.25, 0.5, 0.75 and 1 kg per hectare; VI 2,3,3-trichloroallyl N,N-diisopropylthiolcarbamate, 0.25, 0.5, 0.75 and 1 kg per hectare; VIII ethyl N-ethyl-N-cyclohexylthiolcarbamate, 0.25, 0.5, 0.75 and 1 kg per hectare; I + VIII: 0.75+0.2$, 0.25+0.25 and 0.25+0.75 kg per hectare; II + VIII: 0.75+0.25, 0.25+0.25 and 0.25+0.75 kg per hectare; IV + VIII: 0.75+0.25, 0.25+0.25 and 0.25+0.75 kg per hectare; II + V: 0.75+0. 25, 0.25+0.25 and 0.25+0.75 kg per hectare; II + VI: 0.75+0.25, 0.25+0.25 and 0.25+0.75 kg per hectare; IV + V: 0.75+0.25, 0.25+0.25 and 0.25+0.75 kg per hectare; IV + VI: 0.75+0.25, 0.25+0.25 and 0.25+0.75 kg per hectare.
After 3 to 4 weeks it was ascertained that the compositions had a better herbicidal action than their components, combined with the same good crop plant compatibility.
The results are given below: Active ingredient kg /ha 0.25 0.5 0.75 1 0.25 0.
Crop plant: Beta vulgaris 0 0 0 0 0 Unwanted plants : Alopecurus myosuroides 3 41 50 63 20 Avena fatua 13 45 51 15 Digitaria sanguinalis 25 5 56 70 30 Echinochloa crus-galli 32 50 58 70 30 Setaria faberii 37 46 55 65 35 Stellaria media 5 7 10 16 3 Active ingredient V Beta vulgaris 0 0 0 0 0 Alopecurus myosuroides 1 1 26 45 58 15 Avena fatua 10 20 35 50 15 Digitaria sanguinalis 0 3 5 9 3 Echinochloa crus-galli 0 6 10 16 5 1 Setaria faberii 2 5 8 10 4 Stellaria media 6 7 10 13 3 Active ingredient I + VIII II kg/ha 0.75+ 0. 25+ 0.2 + 0.75+ · Ο. 0.25 0. 5 0.75 0.25 0.
Crop plant : Beta vulgaris 0 0 0 0 Unwanted plants : Alopecurus rr^osuroides 90 60 92 96 Avena fatua 85 6 66 75 Digitaria sanguinalis 98 70 9 100 Echinochloa crus-galli 96 75 98 100 Setaria faberii 95 78 98 100 Stella ia media 46 40 50 45 Active ingredient II + V II Beta vulgaris 0 0 0 0 Alopecurus myosuroldes 93 63 90 98 Avena fatua 8 50 80 92 Digitaria sanguinalis 98 6o 68 98 Echinochloa crus-galli 92 61 68 90 Setaria faberii 97 65 75 100 Stellaria media 50 40 3 40 O . z .29 , 964 Active ingredient IV + VI kg/ha 0.75+ 0.25+ 0.25+ 0.25 0.25 0.75 Crop plant : Beta vulgaris 0 0 0 Unwanted plants : Alopecurus rayosuroides 92 60 90 Avena fatua 80 65 84 Digltaria sanguinalis 98 64 66 Echinochloa crus-galli 98 70 74 Setaria faberii 100 60 65 Stellaria media 43 40 45 0 = no damage 100 = complete destruction -3* - EXAMPLE 5 ' i J In the greenhouse, various plants were treated at a growth height of from 2 to 15 cm with the following amounts of the following individual .active ingredients and compositions thereof as emulsions: I N,N-di-n-propyl-2, 6-dinitro- -trifluoromethylaniline, 0.25, 0.5 and 1 kg per hectare; II N-n-propyl-N-fi-chloroethyl-2, 6-dinitro- -trifluoro- methylaniline, 0.25, 0.5 and 1 kg per hectare; IV N,N-di-(n-propyl) -2, 6-dinitro-4-aminosulfonylaniline, 0.25, 0.5 and 1 kg per hectare; VII l-phenyl-4-amino-5-chloropyridazone- (6 ) , 0.25, 0.5 and 1 kg per hectare; VIII ethyl N-ethyl-N-cyclohexylthiolcarbamate, 0.25, 0.5 and 1 kg per hectare; I + VII + VIII: 0.25+0.25+0.5, 0.25+0.5+0.25 and 0.5+0.25+ 0.25 kg per hectare; II + VII + VIII: 0.25+0.25+0.5, 0.25+0.5+0.25 and 0.5+0.25+ 0.25 kg per hectare; IV + VII + VIII: 0.25+0.25+0.5, 0.25+0.5+0.25 and 0.5+0.25+ i 0.25 kg per hectare.
After 2 to 3 weeks it was ascertained that the compositions had a better herbicidal action than their components, combined with the same good crop plant compatibility.
The results are given below: Active ingredient I II k /ha 0.25 0. 5 1 0.25 0.5 Crop plan : Beta vulgaris 0 0 0 0 0 Unwanted plants : Alopecurus rnyosuroides 15 25 8 13 2 Avena fatua 10 18 35 6 14 Echinochloa crus-galli 10 5 2 1 20 Stellaria media 5 12 30 6 10 Raphanus raphanistrum 6 10 20 4 10 Active ingredient VII VII Beta vulgaris 0 0 0 0 0 Alopecurus rnyosuroides 2 5 35 D 7 Avena fatua 3 5 10 4 5 Echinochloa crus-galli 10 25 7 Stellaria media 10 20 40 0 5 Raphanus raphanistrum 10 16 32 0 2 Active ingredient I + VII + VIII II + VII + kg ha 0.25+ 0.25+ 0.5+ 0.25+ 0.25+ 0.25+ 0.5+ 0.25+ 0.25+ 0.5+ 0.5 0.25 0.25 0.5 0.25 Crop plant : Beta vulgaris 0 0 0 0 0 Unwanted plants : Alopecurus myosuroldes 63 64 70 60 62 Avena fatua 62 60 63 52 5 Echlnochloa crus-galli 71 70 68 75 70 Stellaria media 60 63 60 59 65 Raphanus raphanistrum 55 6+ 58 56 59 no damage complete destruction EXAMPLE 6 In the greenhouse, various plants were treated at a growth height of from 2 to 12 cm with the following amounts of the following individual active ingredients and compositions thereof as oil dispersions: I N,N-di-n-propyl-2,6-dinitro-4-trifluoromethylaniline, 0.25, 0.5, 0.75 and 1 kg per hectare; II N-n-propyl-N-B-chloroethyl-2, 6-dinitro- -trifluoro- methylaniline, 0.25, 0.5, 0.75 and 1 kg per hectare; IV N,N-di-(n-propyl) -2,6-dinitro- -aminosulfonylaniline, 0.25, 0.5, 0.75 and 1 kg per hectare; V 2,3-dichloroallyl N,N-diisopropylthiolcarbamate, 0.25, 0.5, 0.75 and 1 kg per hectare; VI 2,3,3-trichloroallyl N,N-diisopropylthiolcarbamate, 0.25, 0.5, 0.75 and 1 kg per hectare; VIII ethyl N-ethyl-N-cyclohexylthiolcarbamate, 0.25, 0.5» 0.75 and 1 kg per hectare; I + VIII: .0.25+0.75, 0.25+0.25 and 0.75+0.25 kg per hectare; II + VIII: 0.25+0.75, 0.25+0.25 and 0.75+0.25 kg per hectare; IV + VIII: 0,25+0.75, 0.25+0.25 and 0.75+0.25 kg per hectare; II + V: 0.25+0.75, 0.25+0.25 and 0.75+0.25 kg per hectare; IV + V: 0.25+0.75, 0.25+0.25 and 0.75+0.25 kg per hectare; After 2 to 3 weeks it was ascertained that the compositions had a better herbicldal action than their components, O.z. 29,96 combined with the same good crop plant compatibility. The results are given below: - 59" - Active ingredient I kg/ha 0.25 0.5 0.75 1 0.25 0.
Crop plant; Beta vulgaris 0 0 0 0 0 0 Unwanted plants : Alopecurus myosuroides 15 25 30 8 13 24 Avena fatua 10 18 25 3 6 14 Echinochloa crus-galli 10 15 19 25 15 20 Stellaria media 5 12 22 0 6 10 Active ingredient Beta vulgaris 0 0 0 0 0 0 Alopecurus myosuroides 10 20 25 35 7 13 Avena fatua 10 15 24 35 10 18 Echinochloa crus-galli 5 10 18 25 5 15 Stellaria media 1 3 5 7 2 3 Active ingredient VIII Beta vulgaris 0 0 0 0 Alopecurus myosuroides 7 10 18 Avena fatua 4 5 12 20 Echinochloa crus-galli 7 12 15 20 Stellaria media 0 5 7 10 Active ingredient + VIII II + V k /ha 0.25+ 0.25+ 0.75+ 0.25+ 0.2 0.75 0.25 0.25 0.75 0.2 Crop plant : Beta vulgaris 0 0 0 0 Unv/anted plants : Alopecurus myosuroides 50 47 62 55 4 Avena fatua 48 44 58 45 4 Echinochloa crus-galli 45 52 62 51 Stellaria media 42 50 50 45 2 Active ingredient II + V IV + Beta vulgaris 0 0 0 0 Alopecurus myosuroides 66 46 70 60 4 Avena fatua 57 5 56 57 4 Echinochloa crus-galli 60 50 65 62 4 Stellaria media 40 55 46 45 5 EXAMPLE 7 In the greenhouse, loamy sandy soil was filled into-^bts and sown with the seeds of various plants. The soil prepared in this manner was then treated with the following amounts of the following individual active ingredients and compositions thereof as dispersions or dusts: I N,N-di-n-propyl-2,6-dinitro-4-trifluoromethylaniline, 0.6, 6 and 6.6 kg per hectare; II N-n-propyl-N-B-chloroethyl-2,6-dinitro-4-trifluoro- methylaniline, 0.6, 6 and 6.6 kg per hectare; III N-allyl-N-B-chloroethyl-2,6-dinitro-4-trifluoromethyl- aniline, 0.6, 6 and 6.6 kg per hectare; IV N,N-di- (n-propyl ) -2,6-dinitro-4-aminosulfonylaniline , 0.6, 6 and 6.6 kg per hectare; V 2,3-dichloroallyl N,N-diisopropylthiolcarbamate, ί 0.6, 6 and 6.6 kg per hectare; VI 2,5,5-trichloroallyl N,N-diisopropylthiolcarbamate, 0.6, 6 and 6.6 kg per hectare; VII l-phenyl-4-amino-5-chloropyridazone-(6) , 0.6, 6 and 6.6 kg per hectare; I + VI + VII: 0.6+0.6+6, 0.6+6+0.6 and 6+0.6+0.6 kg per hectare; II + VI + VII: 0.6+0.6+6, 0.6+6+0.6 and 6+0.6+0.6 kg per hectare; III + VI + VII: 0.6+0.6+6, 0.6+6+0.6 and 6+0.6+0.6 kg per hectare; IV + VI + VII: 0.6+0.6+6, 0.6+6+0.6 and 6+0.6+0.6 kg per hectare; I + V + VII: 0.6+0.6+6, 0.6+6+0.6 and 6+0.6+0."6 kg per hectare; O.z. 29,964 II + V + VII: 0.6+0.6+6, Ο.β+β+Ο.β and 6+0.6+0.β kg per hectare; and, for comparison, IX N-p-chlorophenyl-N' ,Ν' -dimeth lurea, 0.6, 6 and 6.6 kg per hectare; IX + V + II: 0.6+0.6+6, 0.6+6+0.6 and 6+0.6+0.6 kg per hectare .
After 5 to 4 weeks it was ascertained that the compositions of the invention had, compared with comparative product IX and the composition IX + V + II, better crop plant compatibility.
The results are given below: Active ingredient I II kg/ha 0.6 6.0 6.6 6.0 6.6 Crop plant: Beta vulgaris 0 50 55 Unwanted plants : Alopecurus myosuroldes 48 100 100 45 100 100 Avena fatua 40 100 100 35 100 100 Digitaria sanguinalis 52 100 100 63 100 100 Echinochloa crus-galli 53 100 100 49 100 100 Setaria faberii 54 100 100 70 100 100 Stellaria media 7 67 70 10 65 70 Active ingredient V VI Beta vulgaris 0 23 28 0 25 30 Alopecurus myosuroldes 33 100 100 35 100 100 Avena fatua 28 100 100 30 100 100 Digitaria sanguinalis 5 48 50 7 54 59 Echinochloa crus-galli 10 60 62 12 68 75 Setaria faberii 7 50 54 10 58 60 Stellaria media 8 60 63 9 65 68 Active ingredient I+VI+VII II+VI+VII kg/ha Crop plant : Beta vulgaris 20 25 55 20 25 50 Unwanted plants : Alopecurus myosuroides 100 100 100 100 100 100 Avena fatua 100 IOC 100 100 100 100 Digitaria sanguinalis 100 100 100 100 100 100 Echlnochloa crus-galli 100 100 100 100 100 100 Setaria faberii 100 100 100 100 100 100 Stella ia media 100 100 100 100 100 100 Active ingredient I+V+VII II+V+VII Beta vulgaris 20 23 55 20 23 50 Alopecurus myosuroides 100 100 100 100 100 100 Digitaria sanguinalis 100 100 100 100 100 100 Avena fatua 100 100 100 100 100 100 Echlnochloa crus-galli 100 100 100 100 100 100 Setaria faberii 100 100 100 100 100 100 Stelaria media 100 100 100 100 100 100 EXAMPLE 8 In the greenhouse, loamy sandy soil was filled into^ p ts and sown with various seeds. The soil prepared in this manner was subsequently treated with the following amounts of the following individual active ingredients and compositions thereof as emulsions or dispersions: I N,N-di-n-propyl-2,6-dinitro- -trifluoromethylaniline, 0.5, 1 and 2 kg per hectare; II N-n-propyl-N-B-chloroethyl-2,6-dinitro-!l-trifluoromethyl- aniline, 0.5> 1 and 2 kg per hectare; II 1-phenyl- -amino-5-chloropyridazone- (6) , 0.5, 1 and 2 kg per hectare; IX isopropyl N-phenylcarbamate, 0.5, 1 and 2 kg per hectare; I + VII + IX: 1+0.5+0.5, 0.5+1+0.5 and 0.5+0.5+1 kg per hectare; 11+ VII + IX: 1+0.5+0.5, 0.5+1+0.5 and 0.5+0.5+1 k per hectare .
After 5 to 4 weeks it was ascertained that the composi-tions had a better herbicidal action than their components, combined with the same good crop plant compatibility.
The results are given below: Active ingredient I II kg/ha 0.5 1 2 0.5 1 2 Crop plant : Beta vulgaris 0 0 0 0 0 0 Unwanted plants : Alopecurus myosuroides 1 63 95 40 60 100 Echinochloa crus-galli 50 70 90 45 75 80 Matricaria chamomilla 0 0 0 0 0 0 Stellaria media 7 16 30 6 13 25 Active ingredient I + VII + IX kg/ha 1 + 0.5+ 0.5+ 0.5+ 1 + 0.5+ 0.5 0.5 1 Beta vulgaris 0 0 0 Alopecurus myosuroides 100 100 100 Echinochloa crus-galli 100 100 100 Matricaria chamomilla 90 100 100 Stellaria media 75 96 8o 0 = no damage 100 = complete destruction EXAMPLE 9 In the greenhouse, various plants were treated at <Γ growth height of from 2 to 8 cm with the following amounts of the following individual active 'ingredients and compositions thereof as emulsions or dispersions: II N-n-propyl-N-B-chloroethyl-2,6-dinitro-4-trifluoromethyl aniline, 0.5, 1 and 2 kg per hectare; VII l-phenyl- -amino-5-chloropyridazone-(6) , 0.5, 1 and 2 kg per hectare; X -chlorobutyn-2-yl-l N-3-chlorophenylcarbamate, 0.5, 1 and 2 kg per, hectare; XI 3-methoxycarbon.ylaminophenyl-N-(5' -methylphenyl) -carbamate, 0.5, 1 and 2 kg per hectare; II + VII + X: 1+0.5+0.5, 0.5+1+0.5 and 1+0.5+0.5 kg per hectare; XI + VII + II: 1+0.5+0.5, 0.5+1+0.5 and 1+0.5+0.5 kg per hectare.
After 10 to 1 days it was ascertained that the com-positions had a better herbicidal action than their components, combined with the same good crop plant compatibility.
The results are given below: Active ingredient II VII kg/ha 0.5 1 2 0.5 1 2 Crop plant: Beta vulgaris 0 0 0 0 0 0 Unwanted plants : Avena fatua 10 30 5 10 12 22 Matricaria chamomilla 7 25 7 5 45 60 Stellaria media 8 25 50 30 40 80 Active ingredient II + VII + X kg/ha 1 + 0.5+ 0.5+ 1 0.5+ 1 + 0.5+ 0. 0.5 0.5 1 0.
Beta vulgaris 0 0 0 Avena fatua 100 95 100 8 Matricaria chamomilla 100 100 90 10 Stellaria media 98 97 90 10 0 = no damage 100 = complete destruction
Claims (1)
1. 45060/2 What we claim is:- A herbicide comprising a composition of ' a) a compound of the formula N02 where X denotes lower alkyl, haloalkyl, alkylsulfonyl, methoxy or aminosulfonyl, R1 denotes tetrahydrofurfuryl , cyclopropyl, cyclopropylmethyl , lower alkyl which may be substituted by halogen or alkoxy, alkenyl which may be substituted by halogen or alkoxy, or alkynyl which may be substituted by halogen or alkoxy, and R denotes alkoxyalkyl, propionomethylamide, lower alkyl which may be substituted by halogen, alkenyl which may be substituted by halogen, or alkynyl which may be substituted by halogen, and b) a compound of the formula where R denotes alkyl, alkenyl, alkynyl, bicycloalkyl, tricycloalkyl, phenyl which may be substituted by halogen or alkyl, or cycloalkyl which may be substituted by halogen or alkyl, R1 denotes hydrogen or an alkyl radical' having a maximum of carbon atoms, R2 denotes alkyl which may be substituted by halogen or alkoxy, alkenyl which may be substituted by halogen or alkoxy, alkynyl which may be substituted by halogen or alkoxy, phenyl which may be substituted by halogen, haloalkyl, alkyl or alkoxy, benzyl which may be substituted by halogen, haloalkyl, alkyl or alkoxy, 3-methoxycarbonylaminophenyl or the ra- dical -N^ > , A denotes oxygen or sulfur, and X denotes Civ oxygen or sulfur, with the proviso that. R, R1 and R2 may not simultaneously be alkyl, and optionally c) a compound of the formula A where X denotes amino or o-hydroxy-fi,B,S-trichloroethyl- amino and Y denotes chloro or bromo.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732334563 DE2334563A1 (en) | 1973-07-07 | 1973-07-07 | HERBICIDE |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL45060A0 IL45060A0 (en) | 1974-09-10 |
| IL45060A true IL45060A (en) | 1977-10-31 |
Family
ID=5886189
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL45060A IL45060A (en) | 1973-07-07 | 1974-06-18 | Herbicidal compositions containing a dinitroaniline derivative and a carbamate thiolcarbamate or dithiocarbamate and/or a pyridazone derivative |
Country Status (24)
| Country | Link |
|---|---|
| JP (1) | JPS5036636A (en) |
| AR (1) | AR217032A1 (en) |
| BE (1) | BE817305A (en) |
| BG (2) | BG22056A3 (en) |
| BR (1) | BR7405534D0 (en) |
| CH (1) | CH585005A5 (en) |
| CS (1) | CS189658B2 (en) |
| DD (1) | DD111778A5 (en) |
| DE (1) | DE2334563A1 (en) |
| DK (1) | DK137742C (en) |
| ES (1) | ES428035A1 (en) |
| FR (1) | FR2235645B1 (en) |
| GB (1) | GB1471772A (en) |
| HU (1) | HU169820B (en) |
| IL (1) | IL45060A (en) |
| IT (1) | IT1049296B (en) |
| LU (1) | LU70472A1 (en) |
| NL (1) | NL7409071A (en) |
| NO (1) | NO742394L (en) |
| PL (1) | PL94007B1 (en) |
| RO (1) | RO69333A (en) |
| SE (1) | SE7408882L (en) |
| SU (1) | SU579844A3 (en) |
| ZA (1) | ZA744217B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5520919A (en) * | 1978-07-31 | 1980-02-14 | Nihon Radiator Co | Parts connecting method to aluminium pipe |
| DE2909158A1 (en) * | 1979-03-08 | 1980-09-11 | Basf Ag | HERBICIDAL MIXTURES |
| PT82293B (en) * | 1985-04-08 | 1988-01-11 | Stauffer Chemical Co | Process for the preparation of synergetic herbicide compositions containing a tiolcarbamate and a by product with benzene |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3449111A (en) * | 1966-12-08 | 1969-06-10 | Lilly Co Eli | Method of eliminating weeds |
| US3518076A (en) * | 1967-05-17 | 1970-06-30 | Lilly Co Eli | Method of fliminating weed species with herbicidal combination |
-
1973
- 1973-07-07 DE DE19732334563 patent/DE2334563A1/en not_active Withdrawn
-
1974
- 1974-06-17 BG BG26996A patent/BG22056A3/xx unknown
- 1974-06-17 BG BG7400028827A patent/BG25636A3/xx unknown
- 1974-06-17 AR AR254225A patent/AR217032A1/en active
- 1974-06-18 IL IL45060A patent/IL45060A/en unknown
- 1974-06-25 JP JP49071970A patent/JPS5036636A/ja active Pending
- 1974-06-28 RO RO7479338A patent/RO69333A/en unknown
- 1974-07-01 ZA ZA00744217A patent/ZA744217B/en unknown
- 1974-07-01 NO NO742394A patent/NO742394L/no unknown
- 1974-07-04 FR FR7423307A patent/FR2235645B1/fr not_active Expired
- 1974-07-04 BR BR5534/74A patent/BR7405534D0/en unknown
- 1974-07-04 NL NL7409071A patent/NL7409071A/en not_active Application Discontinuation
- 1974-07-05 SU SU7402042434A patent/SU579844A3/en active
- 1974-07-05 PL PL1974172460A patent/PL94007B1/pl unknown
- 1974-07-05 HU HUBA3109A patent/HU169820B/hu unknown
- 1974-07-05 DK DK361174A patent/DK137742C/en not_active IP Right Cessation
- 1974-07-05 GB GB2987074A patent/GB1471772A/en not_active Expired
- 1974-07-05 IT IT51942/74A patent/IT1049296B/en active
- 1974-07-05 DD DD179738A patent/DD111778A5/xx unknown
- 1974-07-05 CS CS744807A patent/CS189658B2/en unknown
- 1974-07-05 BE BE146264A patent/BE817305A/en unknown
- 1974-07-05 CH CH926774A patent/CH585005A5/xx not_active IP Right Cessation
- 1974-07-05 SE SE7408882A patent/SE7408882L/xx unknown
- 1974-07-05 LU LU70472A patent/LU70472A1/xx unknown
- 1974-07-06 ES ES428035A patent/ES428035A1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL7409071A (en) | 1975-01-09 |
| BG22056A3 (en) | 1976-11-25 |
| LU70472A1 (en) | 1974-11-28 |
| IL45060A0 (en) | 1974-09-10 |
| JPS5036636A (en) | 1975-04-05 |
| AU7028774A (en) | 1976-01-08 |
| DK361174A (en) | 1975-02-24 |
| ES428035A1 (en) | 1977-02-01 |
| BE817305A (en) | 1975-01-06 |
| CH585005A5 (en) | 1977-02-28 |
| DK137742C (en) | 1978-10-09 |
| PL94007B1 (en) | 1977-07-30 |
| GB1471772A (en) | 1977-04-27 |
| DD111778A5 (en) | 1975-03-12 |
| DE2334563A1 (en) | 1975-01-30 |
| BG25636A3 (en) | 1978-11-10 |
| NO742394L (en) | 1975-02-03 |
| HU169820B (en) | 1977-02-28 |
| FR2235645B1 (en) | 1978-07-07 |
| CS189658B2 (en) | 1979-04-30 |
| SU579844A3 (en) | 1977-11-05 |
| ZA744217B (en) | 1975-08-27 |
| AR217032A1 (en) | 1980-02-29 |
| RO69333A (en) | 1980-06-15 |
| SE7408882L (en) | 1975-01-08 |
| IT1049296B (en) | 1981-01-20 |
| DK137742B (en) | 1978-05-01 |
| FR2235645A1 (en) | 1975-01-31 |
| BR7405534D0 (en) | 1975-05-06 |
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