DE1620169C3 - Uracilderivate und deren Verwendung als Herbicide - Google Patents
Uracilderivate und deren Verwendung als HerbicideInfo
- Publication number
- DE1620169C3 DE1620169C3 DE1620169A DE1620169A DE1620169C3 DE 1620169 C3 DE1620169 C3 DE 1620169C3 DE 1620169 A DE1620169 A DE 1620169A DE 1620169 A DE1620169 A DE 1620169A DE 1620169 C3 DE1620169 C3 DE 1620169C3
- Authority
- DE
- Germany
- Prior art keywords
- ioc
- methyluracil
- bromo
- butyl
- sec
- 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.)
- Expired
Links
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical class O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 title claims description 19
- 239000004009 herbicide Substances 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 description 17
- 229940035893 uracil Drugs 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- CTSLUCNDVMMDHG-UHFFFAOYSA-N 5-bromo-3-(butan-2-yl)-6-methylpyrimidine-2,4(1H,3H)-dione Chemical compound CCC(C)N1C(=O)NC(C)=C(Br)C1=O CTSLUCNDVMMDHG-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 150000003385 sodium Chemical class 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 230000002363 herbicidal effect Effects 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- SHVCSCWHWMSGTE-UHFFFAOYSA-N 6-methyluracil Chemical compound CC1=CC(=O)NC(=O)N1 SHVCSCWHWMSGTE-UHFFFAOYSA-N 0.000 description 3
- 230000001588 bifunctional effect Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 125000004956 cyclohexylene group Chemical group 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- OGGXGZAMXPVRFZ-UHFFFAOYSA-N dimethylarsinic acid Chemical compound C[As](C)(O)=O OGGXGZAMXPVRFZ-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- -1 haloacyl hydrocarbon Chemical class 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 125000003452 oxalyl group Chemical group *C(=O)C(*)=O 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- WFXAPWRTSJADQM-UHFFFAOYSA-N 3-tert-butyl-1-[2-(3-tert-butyl-5-chloro-6-methyl-2,4-dioxopyrimidin-1-yl)-2-oxoacetyl]-5-chloro-6-methylpyrimidine-2,4-dione Chemical compound C(C(=O)N1C(=O)N(C(=O)C(=C1C)Cl)C(C)(C)C)(=O)N1C(=O)N(C(=O)C(=C1C)Cl)C(C)(C)C WFXAPWRTSJADQM-UHFFFAOYSA-N 0.000 description 1
- SLJCQVHVNAIXQQ-UHFFFAOYSA-N 5-bromo-1-[2-(5-bromo-3-tert-butyl-6-methyl-2,4-dioxopyrimidin-1-yl)-2-oxoacetyl]-3-tert-butyl-6-methylpyrimidine-2,4-dione Chemical compound C(C(=O)N1C(=O)N(C(=O)C(=C1C)Br)C(C)(C)C)(=O)N1C(=O)N(C(=O)C(=C1C)Br)C(C)(C)C SLJCQVHVNAIXQQ-UHFFFAOYSA-N 0.000 description 1
- 235000011331 Brassica Nutrition 0.000 description 1
- 241000219198 Brassica Species 0.000 description 1
- 241000522254 Cassia Species 0.000 description 1
- 235000014489 Cinnamomum aromaticum Nutrition 0.000 description 1
- 241000234653 Cyperus Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000219053 Rumex Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 235000012308 Tagetes Nutrition 0.000 description 1
- 241000736851 Tagetes Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000004450 alkenylene group Chemical group 0.000 description 1
- 229950004243 cacodylic acid Drugs 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000002587 enol group Chemical group 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 208000006278 hypochromic anemia Diseases 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 244000045561 useful plants Species 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/553—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms with halogen atoms or nitro radicals directly attached to ring carbon atoms, e.g. fluorouracil
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US53967366A | 1966-04-04 | 1966-04-04 | |
| US62246967A | 1967-03-13 | 1967-03-13 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1620169A1 DE1620169A1 (de) | 1970-03-12 |
| DE1620169B2 DE1620169B2 (de) | 1974-10-10 |
| DE1620169C3 true DE1620169C3 (de) | 1975-06-05 |
Family
ID=27066167
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1620169A Expired DE1620169C3 (de) | 1966-04-04 | 1967-04-03 | Uracilderivate und deren Verwendung als Herbicide |
Country Status (13)
| Country | Link |
|---|---|
| BE (1) | BE696551A (ref) |
| BR (1) | BR6788225D0 (ref) |
| CH (2) | CH507256A (ref) |
| DE (1) | DE1620169C3 (ref) |
| DK (1) | DK128833B (ref) |
| ES (1) | ES338910A1 (ref) |
| GB (1) | GB1160028A (ref) |
| IL (1) | IL27610A (ref) |
| MY (1) | MY7200008A (ref) |
| NL (1) | NL6704755A (ref) |
| NO (1) | NO118770B (ref) |
| OA (1) | OA02404A (ref) |
| SE (1) | SE354864B (ref) |
-
1967
- 1967-03-15 IL IL27610A patent/IL27610A/en unknown
- 1967-03-30 NO NO167496A patent/NO118770B/no unknown
- 1967-03-31 DK DK191867AA patent/DK128833B/da unknown
- 1967-04-03 CH CH1430169A patent/CH507256A/de not_active IP Right Cessation
- 1967-04-03 SE SE04580/67A patent/SE354864B/xx unknown
- 1967-04-03 CH CH467667A patent/CH506947A/de not_active IP Right Cessation
- 1967-04-03 DE DE1620169A patent/DE1620169C3/de not_active Expired
- 1967-04-03 OA OA52890A patent/OA02404A/xx unknown
- 1967-04-04 GB GB15436/67A patent/GB1160028A/en not_active Expired
- 1967-04-04 NL NL6704755A patent/NL6704755A/xx unknown
- 1967-04-04 ES ES338910A patent/ES338910A1/es not_active Expired
- 1967-04-04 BE BE696551D patent/BE696551A/xx unknown
- 1967-05-31 BR BR188225/67A patent/BR6788225D0/pt unknown
-
1972
- 1972-12-31 MY MY19728A patent/MY7200008A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK128833B (da) | 1974-07-15 |
| CH507256A (de) | 1971-05-15 |
| MY7200008A (en) | 1972-12-31 |
| DE1620169A1 (de) | 1970-03-12 |
| DE1620169B2 (de) | 1974-10-10 |
| SE354864B (ref) | 1973-03-26 |
| BE696551A (ref) | 1967-09-18 |
| NO118770B (ref) | 1970-02-09 |
| ES338910A1 (es) | 1968-08-16 |
| NL6704755A (ref) | 1967-10-05 |
| OA02404A (fr) | 1970-05-05 |
| GB1160028A (en) | 1969-07-30 |
| BR6788225D0 (pt) | 1973-12-26 |
| IL27610A (en) | 1971-03-24 |
| CH506947A (de) | 1971-05-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| SH | Request for examination between 03.10.1968 and 22.04.1971 | ||
| C3 | Grant after two publication steps (3rd publication) |