DE1695502A1 - Herbizide - Google Patents
HerbizideInfo
- Publication number
- DE1695502A1 DE1695502A1 DE19671695502 DE1695502A DE1695502A1 DE 1695502 A1 DE1695502 A1 DE 1695502A1 DE 19671695502 DE19671695502 DE 19671695502 DE 1695502 A DE1695502 A DE 1695502A DE 1695502 A1 DE1695502 A1 DE 1695502A1
- Authority
- DE
- Germany
- Prior art keywords
- oxadiazolidine
- methyl
- dione
- phenyl
- hydroxy
- 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
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 6
- -1 aliphatic radical Chemical class 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 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
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Chemical group 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 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
- 150000003254 radicals Chemical class 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 244000292693 Poa annua Species 0.000 description 10
- 240000006694 Stellaria media Species 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 240000006122 Chenopodium album Species 0.000 description 9
- 239000004480 active ingredient Substances 0.000 description 9
- 240000005979 Hordeum vulgare Species 0.000 description 8
- 235000007340 Hordeum vulgare Nutrition 0.000 description 8
- 235000009108 Urtica dioica Nutrition 0.000 description 8
- 244000042664 Matricaria chamomilla Species 0.000 description 7
- 235000007232 Matricaria chamomilla Nutrition 0.000 description 7
- 244000274883 Urtica dioica Species 0.000 description 7
- 244000056139 Brassica cretica Species 0.000 description 6
- 235000003351 Brassica cretica Nutrition 0.000 description 6
- 235000003343 Brassica rupestris Nutrition 0.000 description 6
- 241000196324 Embryophyta Species 0.000 description 6
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 6
- 235000010460 mustard Nutrition 0.000 description 6
- 235000008427 Brassica arvensis Nutrition 0.000 description 5
- 244000024671 Brassica kaber Species 0.000 description 5
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 5
- 235000011498 Chenopodium album var missouriense Nutrition 0.000 description 5
- 235000013328 Chenopodium album var. album Nutrition 0.000 description 5
- 235000014052 Chenopodium album var. microphyllum Nutrition 0.000 description 5
- 235000014050 Chenopodium album var. stevensii Nutrition 0.000 description 5
- 235000013012 Chenopodium album var. striatum Nutrition 0.000 description 5
- 241000209140 Triticum Species 0.000 description 5
- 235000021307 Triticum Nutrition 0.000 description 5
- 241000219873 Vicia Species 0.000 description 5
- 240000008042 Zea mays Species 0.000 description 5
- 235000013877 carbamide Nutrition 0.000 description 5
- 240000001592 Amaranthus caudatus Species 0.000 description 4
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 4
- 235000007866 Chamaemelum nobile Nutrition 0.000 description 4
- 240000007594 Oryza sativa Species 0.000 description 4
- 235000007164 Oryza sativa Nutrition 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 235000009344 Chenopodium album Nutrition 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- 241000219146 Gossypium Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 230000002363 herbicidal effect Effects 0.000 description 3
- 235000009566 rice Nutrition 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 241001621841 Alopecurus myosuroides Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000287828 Gallus gallus Species 0.000 description 2
- XGEGHDBEHXKFPX-UHFFFAOYSA-N N-methyl urea Chemical compound CNC(N)=O XGEGHDBEHXKFPX-UHFFFAOYSA-N 0.000 description 2
- 244000088461 Panicum crus-galli Species 0.000 description 2
- 235000011999 Panicum crusgalli Nutrition 0.000 description 2
- 244000062793 Sorghum vulgare Species 0.000 description 2
- 244000098338 Triticum aestivum Species 0.000 description 2
- 235000007244 Zea mays Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 235000011655 cotton Nutrition 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 235000019713 millet Nutrition 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- UTFARDXIQZNFGA-UHFFFAOYSA-N 2-phenyl-1,2,4-oxadiazolidine-3,5-dione Chemical class O1C(=O)NC(=O)N1C1=CC=CC=C1 UTFARDXIQZNFGA-UHFFFAOYSA-N 0.000 description 1
- GJWSLXUABYMWRZ-UHFFFAOYSA-N 4-methyl-2-(3-nitrophenyl)-1,2,4-oxadiazolidine-3,5-dione Chemical compound O=C1N(C)C(=O)ON1C1=CC=CC([N+]([O-])=O)=C1 GJWSLXUABYMWRZ-UHFFFAOYSA-N 0.000 description 1
- 235000016626 Agrimonia eupatoria Nutrition 0.000 description 1
- 241000244831 Agrimonia gryposepala Species 0.000 description 1
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 1
- 244000239348 Echinochloa crus galli var. praticola Species 0.000 description 1
- 244000058871 Echinochloa crus-galli Species 0.000 description 1
- 240000005702 Galium aparine Species 0.000 description 1
- 235000014820 Galium aparine Nutrition 0.000 description 1
- 241001456088 Hesperocnide Species 0.000 description 1
- 235000017945 Matricaria Nutrition 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000209117 Panicum Species 0.000 description 1
- 235000006443 Panicum miliaceum subsp. miliaceum Nutrition 0.000 description 1
- 235000009037 Panicum miliaceum subsp. ruderale Nutrition 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 240000007641 Spergula rubra Species 0.000 description 1
- 244000152045 Themeda triandra Species 0.000 description 1
- 241000405217 Viola <butterfly> Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 241001148683 Zostera marina Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 241001233037 catfish Species 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
- 239000002283 diesel fuel Substances 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009528 severe injury Effects 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
- C07D271/07—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US723919A US3632599A (en) | 1967-04-28 | 1968-04-24 | Substituted 1 2 4-oxadiazolidine-3 5-diones |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB0092295 | 1967-04-28 | ||
| DE1968B0096442 DE1670312C3 (de) | 1967-04-28 | 1968-01-31 | Substituierte 2-Carbamoyloxyphenyl-4-methyl-1,2,4-oxadiazolidin-33-dione |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1695502A1 true DE1695502A1 (de) | 1971-04-01 |
Family
ID=25968313
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19671695502 Pending DE1695502A1 (de) | 1967-04-28 | 1967-04-28 | Herbizide |
| DE1968B0096442 Expired DE1670312C3 (de) | 1967-04-28 | 1968-01-31 | Substituierte 2-Carbamoyloxyphenyl-4-methyl-1,2,4-oxadiazolidin-33-dione |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1968B0096442 Expired DE1670312C3 (de) | 1967-04-28 | 1968-01-31 | Substituierte 2-Carbamoyloxyphenyl-4-methyl-1,2,4-oxadiazolidin-33-dione |
Country Status (9)
| Country | Link |
|---|---|
| AT (1) | AT280689B (en:Method) |
| BE (1) | BE714355A (en:Method) |
| DE (2) | DE1695502A1 (en:Method) |
| DK (1) | DK127031B (en:Method) |
| ES (1) | ES353259A1 (en:Method) |
| FR (1) | FR1560971A (en:Method) |
| GB (1) | GB1215496A (en:Method) |
| NL (1) | NL6805893A (en:Method) |
| SE (1) | SE347001B (en:Method) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE757484A (fr) * | 1969-10-15 | 1971-04-14 | Basf Ag | 1,2,4,-oxadiazolidin-3,5-dione substituee |
-
1967
- 1967-04-28 DE DE19671695502 patent/DE1695502A1/de active Pending
-
1968
- 1968-01-31 DE DE1968B0096442 patent/DE1670312C3/de not_active Expired
- 1968-04-25 NL NL6805893A patent/NL6805893A/xx unknown
- 1968-04-25 SE SE562168A patent/SE347001B/xx unknown
- 1968-04-26 GB GB1982468A patent/GB1215496A/en not_active Expired
- 1968-04-26 DK DK191668A patent/DK127031B/da unknown
- 1968-04-26 BE BE714355D patent/BE714355A/xx unknown
- 1968-04-26 AT AT410468A patent/AT280689B/de not_active IP Right Cessation
- 1968-04-26 FR FR1560971D patent/FR1560971A/fr not_active Expired
- 1968-04-27 ES ES353259A patent/ES353259A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE1670312C3 (de) | 1980-09-18 |
| DK127031B (da) | 1973-09-17 |
| GB1215496A (en) | 1970-12-09 |
| DE1670312B2 (de) | 1980-01-10 |
| SE347001B (en:Method) | 1972-07-24 |
| AT280689B (de) | 1970-04-27 |
| BE714355A (en:Method) | 1968-10-28 |
| FR1560971A (en:Method) | 1969-03-21 |
| ES353259A1 (es) | 1970-12-01 |
| NL6805893A (en:Method) | 1968-10-29 |
| DE1670312A1 (de) | 1972-04-06 |
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