DE2206861B2 - Herbizid auf Benzothiadiazinondioxid-Basis - Google Patents
Herbizid auf Benzothiadiazinondioxid-BasisInfo
- Publication number
- DE2206861B2 DE2206861B2 DE2206861A DE2206861A DE2206861B2 DE 2206861 B2 DE2206861 B2 DE 2206861B2 DE 2206861 A DE2206861 A DE 2206861A DE 2206861 A DE2206861 A DE 2206861A DE 2206861 B2 DE2206861 B2 DE 2206861B2
- Authority
- DE
- Germany
- Prior art keywords
- dioxide
- thiadiazinon
- benzo
- isopropyl
- salt
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 230000002363 herbicidal effect Effects 0.000 title claims description 7
- 239000004009 herbicide Substances 0.000 title claims description 6
- REEXLQXWNOSJKO-UHFFFAOYSA-N 2h-1$l^{4},2,3-benzothiadiazine 1-oxide Chemical compound C1=CC=C2S(=O)NN=CC2=C1 REEXLQXWNOSJKO-UHFFFAOYSA-N 0.000 title description 3
- 239000000203 mixture Substances 0.000 claims description 14
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 description 14
- 240000006694 Stellaria media Species 0.000 description 7
- 241000196324 Embryophyta Species 0.000 description 6
- 239000013543 active substance Substances 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 240000006122 Chenopodium album Species 0.000 description 5
- -1 isopropyl-3-methyl-4,6-dinitrophenol 2-ethoxymethyl-4,6-dinitrophenol Chemical compound 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- 235000014820 Galium aparine Nutrition 0.000 description 4
- 240000005702 Galium aparine Species 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 241000209140 Triticum Species 0.000 description 4
- 235000021307 Triticum Nutrition 0.000 description 4
- 241000219873 Vicia Species 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 241000894007 species Species 0.000 description 4
- 235000009344 Chenopodium album Nutrition 0.000 description 3
- 240000005979 Hordeum vulgare Species 0.000 description 3
- 235000007340 Hordeum vulgare Nutrition 0.000 description 3
- 241000520028 Lamium Species 0.000 description 3
- 235000009198 Lamium amplexicaule Nutrition 0.000 description 3
- 244000303225 Lamium amplexicaule Species 0.000 description 3
- 235000010582 Pisum sativum Nutrition 0.000 description 3
- 240000004713 Pisum sativum Species 0.000 description 3
- 244000098338 Triticum aestivum Species 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical compound CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 description 2
- 235000011305 Capsella bursa pastoris Nutrition 0.000 description 2
- 240000008867 Capsella bursa-pastoris Species 0.000 description 2
- 235000011498 Chenopodium album var missouriense Nutrition 0.000 description 2
- 235000013328 Chenopodium album var. album Nutrition 0.000 description 2
- 235000014052 Chenopodium album var. microphyllum Nutrition 0.000 description 2
- 235000014050 Chenopodium album var. stevensii Nutrition 0.000 description 2
- 235000013012 Chenopodium album var. striatum Nutrition 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 235000007846 Papaver rhoeas Nutrition 0.000 description 2
- 240000004674 Papaver rhoeas Species 0.000 description 2
- 241000219833 Phaseolus Species 0.000 description 2
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 2
- 244000046052 Phaseolus vulgaris Species 0.000 description 2
- 241000822966 Ranunculus arvensis Species 0.000 description 2
- 244000274883 Urtica dioica Species 0.000 description 2
- 235000009108 Urtica dioica Nutrition 0.000 description 2
- 240000005592 Veronica officinalis Species 0.000 description 2
- 125000005210 alkyl ammonium group Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 235000021374 legumes Nutrition 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- FCPJYWJEVFRRKH-UHFFFAOYSA-N 2,4-dinitro-6-pentylphenol Chemical compound CCCCCC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O FCPJYWJEVFRRKH-UHFFFAOYSA-N 0.000 description 1
- DSABESMCWFGGNQ-UHFFFAOYSA-N 2-(ethoxymethyl)-4,6-dinitrophenol Chemical compound CCOCC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O DSABESMCWFGGNQ-UHFFFAOYSA-N 0.000 description 1
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical class OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 1
- 241000244831 Agrimonia gryposepala Species 0.000 description 1
- 235000017300 Alisma plantago Nutrition 0.000 description 1
- 244000233890 Alisma plantago Species 0.000 description 1
- 244000291564 Allium cepa Species 0.000 description 1
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 1
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 1
- 240000001592 Amaranthus caudatus Species 0.000 description 1
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 1
- 244000237956 Amaranthus retroflexus Species 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 241000208479 Anagallis arvensis Species 0.000 description 1
- 241001083841 Aquatica Species 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 241000654850 Aristolochia erecta Species 0.000 description 1
- 241000219305 Atriplex Species 0.000 description 1
- 244000075850 Avena orientalis Species 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- 235000008427 Brassica arvensis Nutrition 0.000 description 1
- 235000003351 Brassica cretica Nutrition 0.000 description 1
- 244000056139 Brassica cretica Species 0.000 description 1
- 244000024671 Brassica kaber Species 0.000 description 1
- 235000003343 Brassica rupestris Nutrition 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000722731 Carex Species 0.000 description 1
- 235000005940 Centaurea cyanus Nutrition 0.000 description 1
- 240000004385 Centaurea cyanus Species 0.000 description 1
- 244000144786 Chrysanthemum segetum Species 0.000 description 1
- 235000005470 Chrysanthemum segetum Nutrition 0.000 description 1
- 241000234653 Cyperus Species 0.000 description 1
- RDJTWDKSYLLHRW-UHFFFAOYSA-N Dinoseb acetate Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1OC(C)=O RDJTWDKSYLLHRW-UHFFFAOYSA-N 0.000 description 1
- 244000044980 Fumaria officinalis Species 0.000 description 1
- 235000006961 Fumaria officinalis Nutrition 0.000 description 1
- 241001488529 Fumaria vaillantii Species 0.000 description 1
- 241001508646 Galeopsis tetrahit Species 0.000 description 1
- 241001101998 Galium Species 0.000 description 1
- 241000209219 Hordeum Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 240000004658 Medicago sativa Species 0.000 description 1
- 235000017587 Medicago sativa ssp. sativa Nutrition 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 208000012868 Overgrowth Diseases 0.000 description 1
- 241000479842 Pella Species 0.000 description 1
- 241000219843 Pisum Species 0.000 description 1
- 244000292697 Polygonum aviculare Species 0.000 description 1
- 241000219000 Populus Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 244000286177 Raphanus raphanistrum Species 0.000 description 1
- 235000000241 Raphanus raphanistrum Nutrition 0.000 description 1
- 235000000245 Raphanus raphanistrum subsp raphanistrum Nutrition 0.000 description 1
- 244000088415 Raphanus sativus Species 0.000 description 1
- 235000011380 Raphanus sativus Nutrition 0.000 description 1
- 241000202758 Scirpus Species 0.000 description 1
- 240000003705 Senecio vulgaris Species 0.000 description 1
- 241000533293 Sesbania emerus Species 0.000 description 1
- 240000006410 Sida spinosa Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 240000003728 Spergula arvensis Species 0.000 description 1
- 241000219793 Trifolium Species 0.000 description 1
- 241001506766 Xanthium Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- GRTOGORTSDXSFK-XJTZBENFSA-N ajmalicine Chemical compound C1=CC=C2C(CCN3C[C@@H]4[C@H](C)OC=C([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 GRTOGORTSDXSFK-XJTZBENFSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 235000012735 amaranth Nutrition 0.000 description 1
- 239000004178 amaranth Substances 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000011280 coal tar Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- 229940043237 diethanolamine Drugs 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012972 dimethylethanolamine Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- RBXVOQPAMPBADW-UHFFFAOYSA-N nitrous acid;phenol Chemical class ON=O.OC1=CC=CC=C1 RBXVOQPAMPBADW-UHFFFAOYSA-N 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- 229940067157 phenylhydrazine Drugs 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- JQYJSVBNPUHHKB-UHFFFAOYSA-M sodium;2-methyl-4,6-dinitrophenolate Chemical compound [Na+].CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1[O-] JQYJSVBNPUHHKB-UHFFFAOYSA-M 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds containing nitrogen-to-oxygen bonds
- A01N33/18—Nitro compounds
- A01N33/20—Nitro compounds containing oxygen or sulfur attached to the carbon skeleton containing the nitro group
- A01N33/22—Nitro compounds containing oxygen or sulfur attached to the carbon skeleton containing the nitro group having at least one oxygen or sulfur atom and at least one nitro group directly attached to the same aromatic ring system
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/88—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with three ring hetero atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N2300/00—Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
b)
N-R
25
30
in der R einen niederen Alkylrest mit bis zu 4 C-Atomen bedeutet oder deren Salzen.
J5
40
Die vorliegende Erfindung betrifft ein Herbizid, das eine Mischung aus einem Nitrophenolderivat mit einem
Benzothiadiazinondioxidderivat enthält
Es ist bekannt, substituierte Nitrophenole oder Benzothiadiazinondioxide als Herbizide zu verwenden.
Ihre herbizide Wirkung ist jedoch schlecht, weshalb bereits diverse synergistische Mischungen jedes dieser
Wirkstoffe mit anderen Verbindungen beschrieben wurden, die jedoch ebenfalls nicht überall befriedigen.
Es wurde gefunden, daß eine Mischung einer Verbindung der Formel
a)
NO2
• V
OR
bO
R,
in der R Wasserstoff, Actyl, Chloracetyl, Ri e>
niederes Alkyl bis Ch, Alkoxyalkyl, Chlor, R2
Wasserstoff oder niederes Alkyl bis O, R3 Nitro
oder Chlor. R4 Wasserstoff, Chlor oder Methyl
bedeutet, mit einer Verbindung der Formel
b)
15
20
in der R einen niederen Alkylrest mit bis zu 4 C-Atomen bedeutet, oder deren Salzen eine
bessere herbizide Wirkung als die Einzelwirkstoffe hat und in vielen Fällen mit überraschendem
Vorteil eingesetzt werden kann in Jenen die bekannten Mischungen versagen.
Als Salze nennen wir die Alkali-, Erdalkali-. Ammonium-, Hydroxyalkyl-ammonium- oder Alkylammonium-, Hydrazin-, Fettalkylammonium-, Pyridin-
oder Anilinsalze, Cycloalkylaminsdze, beispielsweise Salz von Natrium, Lithium, Kalium, Calcium, Eisen,
Methylamin, Trimethylamin, Äthylamin, Diäthanolamin, Äthanolamin, Dimethylamin, Dimethyläthanolamin, Hydrazin, Phenylhydrazin, Pyridin, Äthanolamin, Cyclohexylamin.
Mischungen im Gewichtsverhältnis a : b wie 1 :10 bis
5:1 werden bevorzugt Die Aufwandmengen der Wirkstoffe betragen a) 0,1 bis 3 kg/ha, b) 0,5 bis
10 kg/ha. Die Mischungen werden angewendet, nachdem die Pflanzen Blätter entwickelt haben.
Die Herbizide können in Form von Lösungen, Emulsionen, Suspensionen, Stäubemitteln oder Granulaten angewende werden. Die Anwendungsformen
richten sich ganz nach den Verwendungszwecken; sie sollen in jedem Fall eine feine Verteilung der wirksamen
Substanz gewährleisten.
Zur Herstellung von direkt versprühbaren Lösungen kommen Mineralölfraktionen von mittlerem bis hohem
Siedepunkt, wie Kerosin oder Dieselöl, ferner Kohlenteeröle sowie Öle pflanzlichen oder tierischen Ursprungs, außerdem cyclische Kohlenwasserstoffe, wie
Tetrahydronaphthalin, und alkylierte Napthaline in Betracht.
Wäßrige Anwendungsformen können aus Emulsionskonzentraten, Pasten oder netzbaren Pulvern (Spritzpulvern) durch Zusatz von Wasser bereitet werden. Zur
Herstellung von Emulsionen können die Substanzen als solche oder in einem Lösungsmittel gelöst, mittels Netzoder Dispergiermitteln in Wasser homogenisiert werden. Es können aber auch aus wirksamer Substanz,
Emulgier· oder Dispergiermittel und eventuell Lösungsmittel bestehende Konzentrate hergestellt werden, die
zur Verdünnung mit Wasser geeignet sind. Zu fertigen Spritzbrühen können öle verschiedenen Typs zugesetzt
werden.
Stäubemittel können durch Mischen oder gemeinsames Vermählen der wirksamen Substanzen mit einem
festen Trägerstoff hergestellt werden.
Granulate können durch Bindung der Wirkstoffe an feste Trägerstoffe (Ton, Talkum, Kieselgur oder
Düngemittel) hergestellt werden.
Außerdem können mit ölen direkt versprühbare Dispersionen hergestellt werden.
spielsweise zur Bekämpfung der folgenden Unkräuter,
wobei die Nutzpflanzen nicht geschädigt werden.
Unkrluter;
Abamaplantago-aquatica
Anagallis arvensis
Amaranthus retroflexus
Anthemisspp.
Ammaniaspp.
Atriplex spp.
Butonius umbella tus
Capsella bursa pastoris
Centauri cyanis
Chenopodium album
Chrysanthemum segetum
Cyperus spp.
Fumaria officinalis
Galeopsis tetrahit
Galium aparine
Papaver rhoeas
Polygonuin spp.
Raphanus raphanistrum
Ranunculus arvensis
Scirpus spp.
Senecio vulgaris
Sesbania exaltata
Sida spinosa
Sinapis arvensis
Spergula arvensis
Stellaria media
Urtica urens
Veronica spp.
Vicia spp.
Xanthium spp.
Anagallis arvensis
Amaranthus retroflexus
Anthemisspp.
Ammaniaspp.
Atriplex spp.
Butonius umbella tus
Capsella bursa pastoris
Centauri cyanis
Chenopodium album
Chrysanthemum segetum
Cyperus spp.
Fumaria officinalis
Galeopsis tetrahit
Galium aparine
Papaver rhoeas
Polygonuin spp.
Raphanus raphanistrum
Ranunculus arvensis
Scirpus spp.
Senecio vulgaris
Sesbania exaltata
Sida spinosa
Sinapis arvensis
Spergula arvensis
Stellaria media
Urtica urens
Veronica spp.
Vicia spp.
Xanthium spp.
Kulturpflanzen:
Bohnen
Erbsen
Erdnüsse
Getreide
Gerste
Hafer
Roggen
Weizen
gemeiner Froschlöffel
roter Gauchheil
rauhhaariger Amarant
HundskamBle-Arten
scharlachroter Ammania
Melde-Arten
Schwanenblume
Hirtentäschel
Kornblume
weißer Gänsefuß
Saatwucherblume
Zypergras-Arten
gemeiner Erdrauch
gemeiner Hohlzahn
Klebkraut
Klatschmohn
Knöterich-Arten
Hederich
Ackerhahnenfuß
Binsen-Arten
gemeines Kreuzkraut
Leguminosen-Art
dornige Sammetpappel
Ackersenf
Feldspörgel
Vogelmiere
kleine Brennessel
Ehrenpreis-Arten
V» icke-A; ten
Sptizklee- Arten
Kartoffeln
Leguminosen
Luzerne
Klee
Mais
Reis
Zwiebein
Im Gewächshaus wurden die Pflanzen Gerste (Hordeum vulgäre), Weizen (Triticum aestivum), Klebkraut
(Galium aparine), Taubnessel (Lamium amplexicaule), Wicke-Arten {Vicia spp.) und Vogelmiere
(Stellaria media) bei einer Wuchshöhe von 3 bis 18 cm mit den nachfolgenden Einzelkomponenten und deren
Mischung, jeweils dispergiert in 500 Liter Wasser je Hektar.behandelt:
I 3-lsopropyl-2,1,3-benzo-thiadiazinon-(4)-
2,2-dioxid (13 bzw. 2 kg/ha Wirkstoff) II 2-sec.-Butyl-4,6-dinitro-phenylacetat,
(0,5 bzw. 2 kg/ha Wirkstoff)
I + Il 1,5 + 0,5 kg/ha Wirkstoff
Aus dem Versuchsergebnis ist zu entnehmen, daß gegenüber den Einzelkomponenten die Mischung 8 bis
12 Tage nach der Behandlung eine synergistisch gesteigerte herbizide Wirkung bei günstiger Getieideverträglichkeit
zeigte.
Wirkstoff
I U 1 + U
1,5 2 0,5 2 1,5 + 0,5
Hordeum vulgäre | 0 | 0 | 0 | 20 | 0 |
Triticum aestivum | 0 | 0 | 0 | 15 | 0 |
Galium aparine | 50 | 80 | 30 | 60 | 100 |
Lamium amplexicaule | 15 | 45 | 50 | 90 | 95 |
Vicia spp. | 20 | 30 | 30 | 60 | 90 |
Ste:!aria media | 45 | 80 | 40 | 80 | 100 |
0 = ohne Schädigung.
100 - totale Schädigung.
Entsprechend biologisch wirksam wie die Mischung I + II sind Mischungen von:
3-Isopropyl-2,l 3-benzo-thiadiazinon-(4)-
2,2-dioxid-diäthanol-aminsalz
3-Isopropyl-2,13-benzo-thiadiazinon-(4)-
2,2-dioxid-dimethylaminsalz
3-Isopropyl-2,13-benzo-thiadiazinon-(4)-2,2-dioxid-natriumsalz
3-Isopropyl-2,l,3-beitzo-thiadiazinon-(4)-
2,2-dioxid-kaliumsalz
3-Isopropyl-2,13-benzo-thiadiazinon-(4)-2,2-dioxid-äthanolaminsalz 3-Isopropyl-2,l 3-benzo-thiadiazinon-(4)-
3-Isopropyl-2,13-benzo-thiadiazinon-(4)-2,2-dioxid-äthanolaminsalz 3-Isopropyl-2,l 3-benzo-thiadiazinon-(4)-
2^-dioxid-pyridinsalz
3-Isopropyl-2,l,3-benzo-thiadiazinon-(4)-2^-dioxid-anilinsaIz
3-Isopropyl-2,l,3-benzo-thiadiazinon-(4)-2^-dioxid-anilinsaIz
3-IsopropyI-2,13-benzo-thiadiazinon-(4)-2^-dioxid-phenyIhydrazinsalz
3-Isopropyl-2,13-benzo-thiadiazinon-(4)-
2,2-dioxid-dimethyläthanoIaminsalz
3-Isopropyl-2,13-benzo-thiadiazinon-(4)-2i-dioxid-cyclohexyl-aminsalz
3-sek. Butyl-2,13-benzo-thiadiazinon-(4)-2^-dioxid-dodecylhexamethyleniminsalz
mit
2*Isopropyl-3-methyl-4,6-dinitrophenol
2-ÄthoxymethyI-4,6-dinitrophenol 2-Methyl-4,6-dinitrophenol 2-sek.Butyl-4,6-dinitrophenol
2-tert.-Butyl-4,6-dinitro-phenylacetat 2-tert-Butyl-5-methyl-4,6-dinitrophenylacetat
2-sek.-Butyl-4,6-dinitro-phenylacetat 2-sek.Amyl-4,6-dinitrophenol
2'(1-Methylbutyl)-4,6-dinitrophenol und Mischungen von 3-IsopropyI-2,l3-benzothiadiazinon-(4)-2,2-dioxid
mit 2-Methyl-4,6-dinitrophenol 2-sek.ßutyl4,6-dinitrophenol
2-tert.Butyl-4,6-dinitro-phenylacetat 2-tert.Butyl-5-methyl-4,6-dinitrophenylacetat
2-sek.Amyl-4,6-dinitrophenol 2-Äthoxymethyl-4,6-dinitrophenoI 2-lsopropyl-3-methyl-4,6-dinitrophenol
2-(l-Methylbutyl)-4,6-dinitrophenol
Im Gewächshaus wurden die Pflanzen Weizen
(Triticum aestivum), Erbsen (Pisum sativum). Bohnen
(Phaseolus spp,), Klebkraut (Galium aparine), stengelumfassende
Taubnessel (Lamium amplexicaule), Vogelmiere (Stellaria media) und weißer Gänsefuß (Chenopodium
album) bei einer Wuchshöhe von 2 bis 18 cm mit den nachfolgenden Einzelwirkstoffen und deren Mischungen,
jeweils emulgiert oder dispergiert in 500 Liter Wasser je Hektar, behandelt:
I 3-IsopropyI-2,l ß-benzo-thiadiazinon-(4)-2£-dioxid
(1,5 bzw. 2 kg/ha Wirkstoff)
II 3-Isopropyl-2,l,3-benzo-thiadiazinon-(4)-Ji^-djoxid-dimethylaminosalz
(1,7 bzw. 2 kg/ha Wirkstoff)
(1,7 bzw. 2 kg/ha Wirkstoff)
HI 3-sek,Butyl-2,l,3-benzo-thiadiazmon-(4)-
^-dioxid (0,5 bzw, 1,5 kg/ha Wirkstoff)
IV 2-Methyl-4,6-dinitro-phenoI-natriumsaIz
(0,3, 0,5 bzw, 2 kg/ha Wirkstoff)
V 2-sek,Butyl-4,6-dinitrophenoI
(1 bzw. iß kg/ha Wirkstoff)
IflVli + Oi kg/ha Wirkstoff
II + IV 1,7 + O^ kg/ha Wirkstoff III +VOi+ 1,0 kg/ha Wirkstoff
Aus dem Versuchsergebnis ist zu entnehmen, daß gegenüber den Einzelkomponenten die Mischungen
is eine synergistisch, gesteigerte herbizide Wirkung
zeigen.
Wirkstoff | 2 | 0 | II | 2 | 0 | III | 1,5 | IV | 0,5 | 2 | V | 0 | 1,5 | I - IV | H + IV | III + V | |
1 | 0 | 5 | 0 | 0 | 20 | 0 | 10 | ||||||||||
5 | 1,7 | 5 | 0,5 | 0 | 0,3 | 0 | 10 | 1 | 5 | 5 | 1,5+0,5 | 1,7tO,3 | 05+1 | ||||
kg/ha a. S. | 70 | 0 | 65 | 0 | 0 | 0 | 0 | 15 | 55 | 10 | |||||||
1,5 | 35 | 0 | 25 | 0 | 50 | 0 | 35 | 70 | 60 | 85 | 0 | 0 | 0 | ||||
Triticum aest. | 0 | 75 | 0 | 60 | 0 | 20 | 0 | 45 | 90 | 60 | 85 | 0 | 0 | 0 | |||
Pisum sativ. | 0 | 80 | 50 | 70 | 20 | 65 | 25 | 40 | 80 | 60 | 85 | 0 | 0 | 5 | |||
Phaseolus spp. | 0 | 20 | 5 | 60 | 30 | 40 | 90 | 90 | 100 | 100 | 95 | ||||||
Galium apar. | 40 | 50 | 20 | 30 | 90 | 90 | 90 | ||||||||||
Lamium amp]. | 10 | 50 | 20 | 35 | 100 | 100 | 100 | ||||||||||
Stellaria media | 40 | 100 | 100 | 100 | |||||||||||||
Chenopodium album | 40 | ||||||||||||||||
0 = ohne Schädigung.
100 = totale Schädigung.
Claims (1)
- Patentanspruch:Herbizid, enthaltend eine Mischung einer Verbindung der Formela)toin der R Wasserstoff, Acetyl, Chloracetyl, niederes Alkyl bis C6, Alkoxyalkyl, Chlor, R2 Wasserstoff oder niederes Alkyl bis Q, R3 Nitro oder Chlor, R4 Wasserstoff, Chlor oder Methyl bedeutet, mit einer Verbindung der Formel
Priority Applications (27)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2206861A DE2206861C3 (de) | 1972-02-14 | 1972-02-14 | Herbizid auf Benzothiadiazinondioxid-Basis |
IL41432A IL41432A (en) | 1972-02-14 | 1973-01-30 | Herbicidal compositions comprising a nitrophenol derivative and a 3-alkyl-1h-2,1,3-benzothiadiazin-4(3h)-one 2,2-dioxide derivative |
US328470A US3871864A (en) | 1972-02-14 | 1973-01-31 | Herbicide |
BG022578A BG20271A3 (bg) | 1972-02-14 | 1973-01-31 | Хербициден състав |
ZA730729A ZA73729B (en) | 1972-02-14 | 1973-02-01 | Herbicide |
AU51635/73A AU472465B2 (en) | 1972-02-14 | 1973-02-01 | Herbicide |
IT48011/73A IT977157B (it) | 1972-02-14 | 1973-02-01 | Erbicida |
CA162,936A CA1010256A (en) | 1972-02-14 | 1973-02-05 | Herbicidal compositions containing a nitrophenol derivative and a benzothiadiazinone dioxide derivative |
NLAANVRAGE7301665,A NL176041C (nl) | 1972-02-14 | 1973-02-06 | Werkwijze ter bereiding van herbicide preparaten. |
TR17147A TR17147A (tr) | 1972-02-14 | 1973-02-06 | Herbisid |
SU1878467A SU504449A3 (ru) | 1972-02-14 | 1973-02-08 | Гербицидный состав |
PH14333*A PH10131A (en) | 1972-02-14 | 1973-02-09 | Herbicide |
ES411519A ES411519A1 (es) | 1972-02-14 | 1973-02-11 | Procedimiento para la obtencion de herbicidas a base de de-rivados de nitrofenol. |
PL1973160710A PL84551B1 (de) | 1972-02-14 | 1973-02-12 | |
DD168813A DD101532A5 (de) | 1972-02-14 | 1973-02-12 | |
HU73BA2868A HU166806B (en) | 1972-02-14 | 1973-02-12 | Herbicide comprising one nitrophenol derivative and one benzothiadiazinone dioxide derivative |
CH197573A CH576742A5 (de) | 1972-02-14 | 1973-02-12 | |
FR7304819A FR2172140B1 (de) | 1972-02-14 | 1973-02-12 | |
AR246539A AR193686A1 (es) | 1972-02-14 | 1973-02-12 | Herbicida a base de nitrofenoles substituidos y benzotiazindionas |
GB692073A GB1411856A (en) | 1972-02-14 | 1973-02-13 | Herbicide |
AT126273A AT320344B (de) | 1972-02-14 | 1973-02-13 | Herbizid |
OA54835A OA04334A (fr) | 1972-02-14 | 1973-02-13 | Herbicide. |
DK76373*#A DK132365C (da) | 1972-02-14 | 1973-02-13 | Herbicid |
BR731094A BR7301094D0 (pt) | 1972-02-14 | 1973-02-14 | Composicoes herbicidas |
BE795402D BE795402A (fr) | 1972-02-14 | 1973-02-14 | Herbicide |
CS731085A CS192460B2 (en) | 1972-02-14 | 1973-02-14 | Herbicide means |
SE7302086A SE384438B (sv) | 1972-02-14 | 1973-02-14 | Herbicid innehallande en blandning av ett nitrofenolderivat och ett bensotiazinondioxidderivat |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2206861A DE2206861C3 (de) | 1972-02-14 | 1972-02-14 | Herbizid auf Benzothiadiazinondioxid-Basis |
Publications (3)
Publication Number | Publication Date |
---|---|
DE2206861A1 DE2206861A1 (de) | 1973-08-23 |
DE2206861B2 true DE2206861B2 (de) | 1980-09-11 |
DE2206861C3 DE2206861C3 (de) | 1981-07-02 |
Family
ID=5835911
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE2206861A Expired DE2206861C3 (de) | 1972-02-14 | 1972-02-14 | Herbizid auf Benzothiadiazinondioxid-Basis |
Country Status (27)
Country | Link |
---|---|
US (1) | US3871864A (de) |
AR (1) | AR193686A1 (de) |
AT (1) | AT320344B (de) |
AU (1) | AU472465B2 (de) |
BE (1) | BE795402A (de) |
BG (1) | BG20271A3 (de) |
BR (1) | BR7301094D0 (de) |
CA (1) | CA1010256A (de) |
CH (1) | CH576742A5 (de) |
CS (1) | CS192460B2 (de) |
DD (1) | DD101532A5 (de) |
DE (1) | DE2206861C3 (de) |
DK (1) | DK132365C (de) |
ES (1) | ES411519A1 (de) |
FR (1) | FR2172140B1 (de) |
GB (1) | GB1411856A (de) |
HU (1) | HU166806B (de) |
IL (1) | IL41432A (de) |
IT (1) | IT977157B (de) |
NL (1) | NL176041C (de) |
OA (1) | OA04334A (de) |
PH (1) | PH10131A (de) |
PL (1) | PL84551B1 (de) |
SE (1) | SE384438B (de) |
SU (1) | SU504449A3 (de) |
TR (1) | TR17147A (de) |
ZA (1) | ZA73729B (de) |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2841483A (en) * | 1953-03-05 | 1958-07-01 | Dow Chemical Co | Herbicidal chemical compositions |
DE1088757B (de) * | 1957-12-27 | 1960-09-08 | Hoechst Ag | Mittel zur selektiven Unkrautbekaempfung |
US3708277A (en) * | 1966-08-30 | 1973-01-02 | Basf Ag | Herbicidal method |
-
1972
- 1972-02-14 DE DE2206861A patent/DE2206861C3/de not_active Expired
-
1973
- 1973-01-30 IL IL41432A patent/IL41432A/xx unknown
- 1973-01-31 BG BG022578A patent/BG20271A3/xx unknown
- 1973-01-31 US US328470A patent/US3871864A/en not_active Expired - Lifetime
- 1973-02-01 ZA ZA730729A patent/ZA73729B/xx unknown
- 1973-02-01 AU AU51635/73A patent/AU472465B2/en not_active Expired
- 1973-02-01 IT IT48011/73A patent/IT977157B/it active
- 1973-02-05 CA CA162,936A patent/CA1010256A/en not_active Expired
- 1973-02-06 NL NLAANVRAGE7301665,A patent/NL176041C/xx not_active IP Right Cessation
- 1973-02-06 TR TR17147A patent/TR17147A/xx unknown
- 1973-02-08 SU SU1878467A patent/SU504449A3/ru active
- 1973-02-09 PH PH14333*A patent/PH10131A/en unknown
- 1973-02-11 ES ES411519A patent/ES411519A1/es not_active Expired
- 1973-02-12 DD DD168813A patent/DD101532A5/xx unknown
- 1973-02-12 CH CH197573A patent/CH576742A5/xx not_active IP Right Cessation
- 1973-02-12 PL PL1973160710A patent/PL84551B1/pl unknown
- 1973-02-12 HU HU73BA2868A patent/HU166806B/hu unknown
- 1973-02-12 AR AR246539A patent/AR193686A1/es active
- 1973-02-12 FR FR7304819A patent/FR2172140B1/fr not_active Expired
- 1973-02-13 GB GB692073A patent/GB1411856A/en not_active Expired
- 1973-02-13 DK DK76373*#A patent/DK132365C/da not_active IP Right Cessation
- 1973-02-13 AT AT126273A patent/AT320344B/de not_active IP Right Cessation
- 1973-02-13 OA OA54835A patent/OA04334A/xx unknown
- 1973-02-14 SE SE7302086A patent/SE384438B/xx unknown
- 1973-02-14 CS CS731085A patent/CS192460B2/cs unknown
- 1973-02-14 BE BE795402D patent/BE795402A/xx not_active IP Right Cessation
- 1973-02-14 BR BR731094A patent/BR7301094D0/pt unknown
Also Published As
Publication number | Publication date |
---|---|
PL84551B1 (de) | 1976-04-30 |
IL41432A0 (en) | 1973-03-30 |
AU5163573A (en) | 1974-08-01 |
CS192460B2 (en) | 1979-08-31 |
OA04334A (fr) | 1980-01-31 |
GB1411856A (en) | 1975-10-29 |
SE384438B (sv) | 1976-05-10 |
US3871864A (en) | 1975-03-18 |
IL41432A (en) | 1975-04-25 |
PH10131A (en) | 1976-09-02 |
BG20271A3 (bg) | 1975-11-05 |
DK132365C (da) | 1976-05-10 |
FR2172140A1 (de) | 1973-09-28 |
BE795402A (fr) | 1973-08-14 |
HU166806B (en) | 1975-06-28 |
AT320344B (de) | 1975-02-10 |
TR17147A (tr) | 1974-04-25 |
SU504449A3 (ru) | 1976-02-25 |
AU472465B2 (en) | 1976-05-27 |
ES411519A1 (es) | 1976-09-01 |
DK132365B (da) | 1975-12-01 |
ZA73729B (en) | 1973-11-28 |
NL7301665A (de) | 1973-08-16 |
BR7301094D0 (pt) | 1973-09-20 |
NL176041B (nl) | 1984-09-17 |
DD101532A5 (de) | 1973-11-12 |
CH576742A5 (de) | 1976-06-30 |
AR193686A1 (es) | 1973-05-11 |
NL176041C (nl) | 1985-02-18 |
FR2172140B1 (de) | 1978-03-03 |
DE2206861A1 (de) | 1973-08-23 |
DE2206861C3 (de) | 1981-07-02 |
IT977157B (it) | 1974-09-10 |
CA1010256A (en) | 1977-05-17 |
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