DE2224161A1 - Selektiv herbizide mittel - Google Patents
Selektiv herbizide mittelInfo
- Publication number
- DE2224161A1 DE2224161A1 DE2224161A DE2224161A DE2224161A1 DE 2224161 A1 DE2224161 A1 DE 2224161A1 DE 2224161 A DE2224161 A DE 2224161A DE 2224161 A DE2224161 A DE 2224161A DE 2224161 A1 DE2224161 A1 DE 2224161A1
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- phenyl
- triazin
- amino
- substituted
- 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.)
- Pending
Links
- 239000004009 herbicide Substances 0.000 title claims description 6
- 241000196324 Embryophyta Species 0.000 claims description 13
- 241000335053 Beta vulgaris Species 0.000 claims description 12
- 235000016068 Berberis vulgaris Nutrition 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000004606 Fillers/Extenders Substances 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000004970 halomethyl group Chemical group 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 239000002904 solvent Substances 0.000 description 12
- -1 3-methoxycarbonylaminophenyl Chemical group 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- 239000003995 emulsifying agent Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 230000006378 damage Effects 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 230000002363 herbicidal effect Effects 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 241000219422 Urtica Species 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 241000209761 Avena Species 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 244000042664 Matricaria chamomilla Species 0.000 description 3
- 235000007232 Matricaria chamomilla Nutrition 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 244000062793 Sorghum vulgare Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
- 239000006072 paste Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 235000005781 Avena Nutrition 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 235000007351 Eleusine Nutrition 0.000 description 2
- 241000209215 Eleusine Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 241000234642 Festuca Species 0.000 description 2
- 241000748465 Galinsoga Species 0.000 description 2
- 241000209082 Lolium Species 0.000 description 2
- 235000017945 Matricaria Nutrition 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- BFNNILAMSKQDRN-UHFFFAOYSA-N 2h-1,2,4-triazin-5-one Chemical compound O=C1C=NNC=N1 BFNNILAMSKQDRN-UHFFFAOYSA-N 0.000 description 1
- 240000002245 Acer pensylvanicum Species 0.000 description 1
- 235000006760 Acer pensylvanicum Nutrition 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 241000743985 Alopecurus Species 0.000 description 1
- 240000001592 Amaranthus caudatus Species 0.000 description 1
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 1
- 235000007320 Avena fatua Nutrition 0.000 description 1
- 241000209764 Avena fatua Species 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- 244000056139 Brassica cretica Species 0.000 description 1
- 235000003351 Brassica cretica Nutrition 0.000 description 1
- 235000003343 Brassica rupestris Nutrition 0.000 description 1
- 241000209200 Bromus Species 0.000 description 1
- 235000007866 Chamaemelum nobile Nutrition 0.000 description 1
- 241000219312 Chenopodium Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241000192043 Echinochloa Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 206010053759 Growth retardation Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241000801118 Lepidium Species 0.000 description 1
- 244000211187 Lepidium sativum Species 0.000 description 1
- 235000007849 Lepidium sativum Nutrition 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- 241000209510 Liliopsida Species 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 241000746981 Phleum Species 0.000 description 1
- 241000746983 Phleum pratense Species 0.000 description 1
- 241000205407 Polygonum Species 0.000 description 1
- 244000292697 Polygonum aviculare Species 0.000 description 1
- 235000006386 Polygonum aviculare Nutrition 0.000 description 1
- 241000780602 Senecio Species 0.000 description 1
- 235000005775 Setaria Nutrition 0.000 description 1
- 241000232088 Setaria <nematode> Species 0.000 description 1
- 240000006694 Stellaria media Species 0.000 description 1
- 244000152045 Themeda triandra Species 0.000 description 1
- 244000274883 Urtica dioica Species 0.000 description 1
- 235000009108 Urtica dioica Nutrition 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical class ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- OFLXLNCGODUUOT-UHFFFAOYSA-N acetohydrazide Chemical compound C\C(O)=N\N OFLXLNCGODUUOT-UHFFFAOYSA-N 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- LRDJLICCIZGMSB-UHFFFAOYSA-N ethenyldiazene Chemical compound C=CN=N LRDJLICCIZGMSB-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- QKLCQKPAECHXCQ-UHFFFAOYSA-N ethyl phenylglyoxylate Chemical compound CCOC(=O)C(=O)C1=CC=CC=C1 QKLCQKPAECHXCQ-UHFFFAOYSA-N 0.000 description 1
- 241001233957 eudicotyledons Species 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 244000230030 foxtail bristlegrass Species 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 208000037824 growth disorder Diseases 0.000 description 1
- 231100000001 growth retardation Toxicity 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- VHCNQEUWZYOAEV-UHFFFAOYSA-N metamitron Chemical compound O=C1N(N)C(C)=NN=C1C1=CC=CC=C1 VHCNQEUWZYOAEV-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- HTAKLAKDSQCGRF-UHFFFAOYSA-N n,n'-diaminoethanimidamide Chemical compound NNC(C)=NN HTAKLAKDSQCGRF-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000007530 organic bases Chemical group 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 230000009528 severe injury Effects 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000036435 stunted growth Effects 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
- C07C251/88—Hydrazones having also the other nitrogen atom doubly-bound to a carbon atom, e.g. azines
-
- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/707—1,2,3- or 1,2,4-triazines; Hydrogenated 1,2,3- or 1,2,4-triazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
- C07D253/06—1,2,4-Triazines
- C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
- C07D253/07—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members with hetero atoms, or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- 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)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (20)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2224161A DE2224161A1 (de) | 1972-05-18 | 1972-05-18 | Selektiv herbizide mittel |
| DD170729A DD104019A5 (enrdf_load_stackoverflow) | 1972-05-18 | 1973-05-09 | |
| IL42271A IL42271A (en) | 1972-05-18 | 1973-05-15 | 6-substituted phenyl-3-methyl-4-amino-5h-1,2,4-triazin-5-ones and method and compositions containing them for combating weeds in beet cultures |
| YU1283/75A YU39297B (en) | 1972-05-18 | 1973-05-15 | Process for preparing 6-phenyl-substituted 3-methyl-4-amino-5h-1,2,4-triazine-5-ones |
| TR17273A TR17273A (tr) | 1972-05-18 | 1973-05-15 | Secimli herbisid maddeler |
| SU731921921A SU728687A3 (ru) | 1972-05-18 | 1973-05-16 | Способ борьбы с сорной растительностью |
| BE131153A BE799584A (fr) | 1972-05-18 | 1973-05-16 | Nouvelles compositions herbicides selectives |
| CH700473A CH581951A5 (enrdf_load_stackoverflow) | 1972-05-18 | 1973-05-16 | |
| IT24202/73A IT987656B (it) | 1972-05-18 | 1973-05-16 | Materiali erbicidi selettivi |
| PL1973162625A PL89244B1 (enrdf_load_stackoverflow) | 1972-05-18 | 1973-05-17 | |
| ES414824A ES414824A1 (es) | 1972-05-18 | 1973-05-17 | Procedimiento para la lucha selectiva contra malezas en cultivos de remolacha. |
| IE788/73A IE37643B1 (en) | 1972-05-18 | 1973-05-17 | Selectively herbicidal agents |
| CS3539A CS174882B2 (enrdf_load_stackoverflow) | 1972-05-18 | 1973-05-17 | |
| GB2355273A GB1368416A (en) | 1972-05-18 | 1973-05-17 | Selectively herbicidal agents |
| HUBA2929A HU166183B (enrdf_load_stackoverflow) | 1972-05-18 | 1973-05-18 | |
| AT438673A AT325341B (de) | 1972-05-18 | 1973-05-18 | Herbizide wirkstoffe für rübenkulturen |
| NLAANVRAGE7307004,A NL177461C (nl) | 1972-05-18 | 1973-05-18 | Werkwijze voor de bereiding van een herbicide preparaat, zo verkregen gevormd preparaat alsmede werkwijze voor de selectieve onkruidbestrijding in cultures van bieten. |
| AT820174*7A AT327607B (de) | 1972-05-18 | 1973-05-18 | Selektives rubenherbizid |
| FR7318105A FR2185034B1 (enrdf_load_stackoverflow) | 1972-05-18 | 1973-05-18 | |
| JP5481173A JPS5626644B2 (enrdf_load_stackoverflow) | 1972-05-18 | 1973-05-18 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2224161A DE2224161A1 (de) | 1972-05-18 | 1972-05-18 | Selektiv herbizide mittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2224161A1 true DE2224161A1 (de) | 1973-11-29 |
Family
ID=5845170
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2224161A Pending DE2224161A1 (de) | 1972-05-18 | 1972-05-18 | Selektiv herbizide mittel |
Country Status (19)
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS50154428A (enrdf_load_stackoverflow) * | 1973-09-18 | 1975-12-12 | ||
| US4047929A (en) * | 1975-08-21 | 1977-09-13 | Bayer Aktiengesellschaft | Synergistic herbicidal compositions |
| US5292949A (en) * | 1991-12-20 | 1994-03-08 | Saurefabrik Schweizerhall | Process for the preparation of acid anhydrides |
| EP0620971A1 (de) * | 1993-04-22 | 1994-10-26 | Stefes Pflanzenschutz GmbH | Metamitron enthaltende wässrige Formulierungen |
| EP0641516A2 (de) | 1993-09-04 | 1995-03-08 | Stefes Pflanzenschutz GmbH | Wässrige herbizide Suspensionskonzentrate |
| WO2003020034A1 (de) * | 2001-09-03 | 2003-03-13 | Bayer Cropscience Ag | Verfahren zur fruchtausdünnung |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2482421B1 (fr) * | 1980-05-19 | 1985-08-02 | Slovenska Akademia Vied | Agent permettant d'augmenter la recolte de produits agricoles |
| DE3102318A1 (de) | 1981-01-24 | 1982-08-26 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von 3,6-disubstituierten 4-amino-1,2,4-triazin-5-onen |
| DE3206234A1 (de) * | 1982-02-20 | 1983-09-29 | Bayer Ag, 5090 Leverkusen | Selektives ruebenherbizid enthaltend metamitron in kombination mit einem naphthochinonderivat |
| JPS6076640U (ja) * | 1983-10-31 | 1985-05-29 | 中央パツケージング工業株式会社 | 洗濯物収納袋 |
| JPS60120908U (ja) * | 1984-01-26 | 1985-08-15 | 株式会社 サンアイ | 袋体吸着兼用吊下げ具 |
| DE19605786A1 (de) | 1996-02-16 | 1997-08-21 | Hoechst Schering Agrevo Gmbh | Ölsuspensionskonzentrate |
| EP2052610A1 (de) | 2007-10-24 | 2009-04-29 | Bayer CropScience AG | Herbizid-Kombination |
| DE102008037630A1 (de) | 2008-08-14 | 2010-02-18 | Bayer Cropscience Ag | Herbizid-Kombination mit Dimethoxytriazinyl-substituierten Difluormethansulfonylaniliden |
| EP2238834A1 (de) * | 2009-04-07 | 2010-10-13 | Bayer CropScience Aktiengesellschaft | Defoliant auf Basis von Thidiazuron und 1,2,4-Triazinonen |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2107757C3 (de) * | 1971-02-18 | 1980-02-28 | Bayer Ag, 5090 Leverkusen | 4-Amino-1,2,4-triazin-5-one, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide |
| BE786840A (fr) * | 1971-07-29 | 1973-01-29 | Bayer Ag | Procede de preparation de 1,2,4-triazine -5-ones |
-
1972
- 1972-05-18 DE DE2224161A patent/DE2224161A1/de active Pending
-
1973
- 1973-05-09 DD DD170729A patent/DD104019A5/xx unknown
- 1973-05-15 YU YU1283/75A patent/YU39297B/xx unknown
- 1973-05-15 IL IL42271A patent/IL42271A/en unknown
- 1973-05-15 TR TR17273A patent/TR17273A/xx unknown
- 1973-05-16 SU SU731921921A patent/SU728687A3/ru active
- 1973-05-16 BE BE131153A patent/BE799584A/xx not_active IP Right Cessation
- 1973-05-16 CH CH700473A patent/CH581951A5/xx not_active IP Right Cessation
- 1973-05-16 IT IT24202/73A patent/IT987656B/it active
- 1973-05-17 CS CS3539A patent/CS174882B2/cs unknown
- 1973-05-17 ES ES414824A patent/ES414824A1/es not_active Expired
- 1973-05-17 GB GB2355273A patent/GB1368416A/en not_active Expired
- 1973-05-17 IE IE788/73A patent/IE37643B1/xx unknown
- 1973-05-17 PL PL1973162625A patent/PL89244B1/pl unknown
- 1973-05-18 HU HUBA2929A patent/HU166183B/hu unknown
- 1973-05-18 FR FR7318105A patent/FR2185034B1/fr not_active Expired
- 1973-05-18 AT AT820174*7A patent/AT327607B/de not_active IP Right Cessation
- 1973-05-18 AT AT438673A patent/AT325341B/de not_active IP Right Cessation
- 1973-05-18 NL NLAANVRAGE7307004,A patent/NL177461C/xx not_active IP Right Cessation
- 1973-05-18 JP JP5481173A patent/JPS5626644B2/ja not_active Expired
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS50154428A (enrdf_load_stackoverflow) * | 1973-09-18 | 1975-12-12 | ||
| US4047929A (en) * | 1975-08-21 | 1977-09-13 | Bayer Aktiengesellschaft | Synergistic herbicidal compositions |
| US5292949A (en) * | 1991-12-20 | 1994-03-08 | Saurefabrik Schweizerhall | Process for the preparation of acid anhydrides |
| EP0620971A1 (de) * | 1993-04-22 | 1994-10-26 | Stefes Pflanzenschutz GmbH | Metamitron enthaltende wässrige Formulierungen |
| EP0641516A2 (de) | 1993-09-04 | 1995-03-08 | Stefes Pflanzenschutz GmbH | Wässrige herbizide Suspensionskonzentrate |
| WO2003020034A1 (de) * | 2001-09-03 | 2003-03-13 | Bayer Cropscience Ag | Verfahren zur fruchtausdünnung |
| US9232802B2 (en) | 2001-09-03 | 2016-01-12 | Adama Fahrenheit B.V | Method for thinning fruit |
Also Published As
| Publication number | Publication date |
|---|---|
| SU728687A3 (ru) | 1980-04-15 |
| YU39297B (en) | 1984-10-31 |
| IE37643L (en) | 1973-11-18 |
| FR2185034A1 (enrdf_load_stackoverflow) | 1973-12-28 |
| IE37643B1 (en) | 1977-09-14 |
| CS174882B2 (enrdf_load_stackoverflow) | 1977-04-29 |
| PL89244B1 (enrdf_load_stackoverflow) | 1976-11-30 |
| AT327607B (de) | 1976-02-10 |
| ES414824A1 (es) | 1976-02-01 |
| NL177461B (nl) | 1985-05-01 |
| YU128373A (en) | 1982-05-31 |
| DD104019A5 (enrdf_load_stackoverflow) | 1974-02-20 |
| GB1368416A (en) | 1974-09-25 |
| ATA820174A (de) | 1975-04-15 |
| BE799584A (fr) | 1973-11-16 |
| NL177461C (nl) | 1985-10-01 |
| IT987656B (it) | 1975-03-20 |
| IL42271A0 (en) | 1973-07-30 |
| CH581951A5 (enrdf_load_stackoverflow) | 1976-11-30 |
| NL7307004A (enrdf_load_stackoverflow) | 1973-11-20 |
| TR17273A (tr) | 1975-03-24 |
| IL42271A (en) | 1976-10-31 |
| HU166183B (enrdf_load_stackoverflow) | 1975-02-28 |
| AT325341B (de) | 1975-10-10 |
| FR2185034B1 (enrdf_load_stackoverflow) | 1977-02-11 |
| JPS4954537A (enrdf_load_stackoverflow) | 1974-05-27 |
| JPS5626644B2 (enrdf_load_stackoverflow) | 1981-06-19 |
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