DE1240698B - - Google Patents
Info
- Publication number
- DE1240698B DE1240698B DE19601240698 DE1240698A DE1240698B DE 1240698 B DE1240698 B DE 1240698B DE 19601240698 DE19601240698 DE 19601240698 DE 1240698 A DE1240698 A DE 1240698A DE 1240698 B DE1240698 B DE 1240698B
- Authority
- DE
- Germany
- Prior art keywords
- radical
- methyl
- alkyl
- bromine
- bromo
- 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
- -1 alkynyl radical Chemical class 0.000 claims description 122
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 75
- 239000004480 active ingredient Substances 0.000 claims description 55
- 241000196324 Embryophyta Species 0.000 claims description 31
- 239000000460 chlorine Substances 0.000 claims description 31
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 21
- 229910052801 chlorine Inorganic materials 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- 150000003254 radicals Chemical class 0.000 claims description 16
- 229910052794 bromium Inorganic materials 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 11
- 229910052751 metal Inorganic materials 0.000 claims description 10
- 239000002184 metal Substances 0.000 claims description 10
- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical compound O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 claims description 10
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims description 9
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000004434 sulfur atom Chemical group 0.000 claims description 5
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- JEVCWSUVFOYBFI-UHFFFAOYSA-N cyanyl Chemical compound N#[C] JEVCWSUVFOYBFI-UHFFFAOYSA-N 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- RFMQOHXWHFHOJF-UHFFFAOYSA-N cyano thiocyanate Chemical compound N#CSC#N RFMQOHXWHFHOJF-UHFFFAOYSA-N 0.000 claims description 2
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- BLNWTAHYTCHDJH-UHFFFAOYSA-O hydroxy(oxo)azanium Chemical compound O[NH+]=O BLNWTAHYTCHDJH-UHFFFAOYSA-O 0.000 claims description 2
- LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical group O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 claims description 2
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 claims 1
- 229930002875 chlorophyll Natural products 0.000 claims 1
- 235000019804 chlorophyll Nutrition 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 63
- 229940035893 uracil Drugs 0.000 description 36
- 230000006378 damage Effects 0.000 description 16
- 235000017896 Digitaria Nutrition 0.000 description 15
- 241001303487 Digitaria <clam> Species 0.000 description 15
- 239000003921 oil Substances 0.000 description 15
- 238000000227 grinding Methods 0.000 description 12
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 12
- 241000219198 Brassica Species 0.000 description 10
- 239000008187 granular material Substances 0.000 description 10
- 239000008188 pellet Substances 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 9
- 239000002689 soil Substances 0.000 description 9
- 239000007921 spray Substances 0.000 description 8
- SHVCSCWHWMSGTE-UHFFFAOYSA-N 6-methyluracil Chemical compound CC1=CC(=O)NC(=O)N1 SHVCSCWHWMSGTE-UHFFFAOYSA-N 0.000 description 7
- 235000007320 Avena fatua Nutrition 0.000 description 7
- 241000209764 Avena fatua Species 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 7
- 239000004009 herbicide Substances 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- ZEMGGZBWXRYJHK-UHFFFAOYSA-N thiouracil Chemical compound O=C1C=CNC(=S)N1 ZEMGGZBWXRYJHK-UHFFFAOYSA-N 0.000 description 7
- 235000011331 Brassica Nutrition 0.000 description 6
- 238000005507 spraying Methods 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 240000002439 Sorghum halepense Species 0.000 description 5
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 5
- 230000002363 herbicidal effect Effects 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 5
- 150000002430 hydrocarbons Chemical class 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 235000012827 Digitaria sp Nutrition 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 229920005552 sodium lignosulfonate Polymers 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- 229950000329 thiouracil Drugs 0.000 description 4
- 241000339490 Brachyachne Species 0.000 description 3
- 241000508725 Elymus repens Species 0.000 description 3
- 240000000111 Saccharum officinarum Species 0.000 description 3
- 235000007201 Saccharum officinarum Nutrition 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 241000209072 Sorghum Species 0.000 description 3
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 3
- 241001506773 Xanthium sp. Species 0.000 description 3
- 239000011149 active material Substances 0.000 description 3
- 150000001447 alkali salts Chemical class 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 235000013339 cereals Nutrition 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000012053 oil suspension Substances 0.000 description 3
- 230000008635 plant growth Effects 0.000 description 3
- 239000004576 sand Substances 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 239000010455 vermiculite Substances 0.000 description 3
- 229910052902 vermiculite Inorganic materials 0.000 description 3
- 235000019354 vermiculite Nutrition 0.000 description 3
- DPVIABCMTHHTGB-UHFFFAOYSA-N 2,4,6-trichloropyrimidine Chemical compound ClC1=CC(Cl)=NC(Cl)=N1 DPVIABCMTHHTGB-UHFFFAOYSA-N 0.000 description 2
- 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 2
- FTPDTGDDXHRDAB-UHFFFAOYSA-N 5-bromo-3-phenyl-1H-pyrimidine-2,4-dione Chemical compound BrC=1C(N(C(NC1)=O)C1=CC=CC=C1)=O FTPDTGDDXHRDAB-UHFFFAOYSA-N 0.000 description 2
- 235000005340 Asparagus officinalis Nutrition 0.000 description 2
- 235000003351 Brassica cretica Nutrition 0.000 description 2
- 235000003343 Brassica rupestris Nutrition 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 244000020518 Carthamus tinctorius Species 0.000 description 2
- 235000003255 Carthamus tinctorius Nutrition 0.000 description 2
- 241000207892 Convolvulus Species 0.000 description 2
- 241000192043 Echinochloa Species 0.000 description 2
- 244000058871 Echinochloa crus-galli Species 0.000 description 2
- 241000132521 Erigeron Species 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- HWGBHCRJGXAGEU-UHFFFAOYSA-N Methylthiouracil Chemical compound CC1=CC(=O)NC(=S)N1 HWGBHCRJGXAGEU-UHFFFAOYSA-N 0.000 description 2
- 241000219925 Oenothera Species 0.000 description 2
- 241000282320 Panthera leo Species 0.000 description 2
- 240000007643 Phytolacca americana Species 0.000 description 2
- 235000009074 Phytolacca americana Nutrition 0.000 description 2
- 235000005775 Setaria Nutrition 0.000 description 2
- 241000232088 Setaria <nematode> Species 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 241000607059 Solidago Species 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000002283 diesel fuel Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 150000002540 isothiocyanates Chemical class 0.000 description 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 235000010460 mustard Nutrition 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000375 suspending agent Substances 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- UPLURGSDLNKCSU-UHFFFAOYSA-N 1,5,6,7-tetrahydrocyclopenta[d]pyrimidine-2,4-dione Chemical compound O=C1NC(=O)NC2=C1CCC2 UPLURGSDLNKCSU-UHFFFAOYSA-N 0.000 description 1
- PZNPLUBHRSSFHT-RRHRGVEJSA-N 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCCC(=O)O[C@@H](COP([O-])(=O)OCC[N+](C)(C)C)COC(=O)CCCCCCCCCCCCCCC PZNPLUBHRSSFHT-RRHRGVEJSA-N 0.000 description 1
- UTQNKKSJPHTPBS-UHFFFAOYSA-N 2,2,2-trichloroethanone Chemical group ClC(Cl)(Cl)[C]=O UTQNKKSJPHTPBS-UHFFFAOYSA-N 0.000 description 1
- WUZUCYIWIRRVSO-UHFFFAOYSA-N 2,4-dioxo-3-propan-2-yl-1H-pyrimidine-5-carbonitrile Chemical compound C(C)(C)N1C(NC=C(C1=O)C#N)=O WUZUCYIWIRRVSO-UHFFFAOYSA-N 0.000 description 1
- XFEOJAACMWUDIH-UHFFFAOYSA-N 2-[(3-cyclohexyl-6-methyl-2,4-dioxo-1H-pyrimidin-5-yl)methylsulfanyl]acetic acid Chemical compound C(=O)(O)CSCC=1C(N(C(NC=1C)=O)C1CCCCC1)=O XFEOJAACMWUDIH-UHFFFAOYSA-N 0.000 description 1
- 125000005999 2-bromoethyl group Chemical group 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- 125000004135 2-norbornyl group Chemical group [H]C1([H])C([H])([H])C2([H])C([H])([H])C1([H])C([H])([H])C2([H])* 0.000 description 1
- BZGYBSUEGJYNFT-UHFFFAOYSA-N 3-(3-bicyclo[2.2.1]heptanyl)-6-methyl-1h-pyrimidine-2,4-dione Chemical compound O=C1NC(C)=CC(=O)N1C1C(C2)CCC2C1 BZGYBSUEGJYNFT-UHFFFAOYSA-N 0.000 description 1
- IIYARLBKDOYRRB-UHFFFAOYSA-N 3-(3-bicyclo[2.2.1]heptanylmethyl)-5-bromo-6-methyl-1h-pyrimidine-2,4-dione Chemical compound O=C1C(Br)=C(C)NC(=O)N1CC1C(C2)CCC2C1 IIYARLBKDOYRRB-UHFFFAOYSA-N 0.000 description 1
- RPJIXRZLQYDQDS-UHFFFAOYSA-N 3-(5-bromo-6-methyl-2,4-dioxo-1H-pyrimidin-3-yl)propanenitrile Chemical compound C(#N)CCN1C(NC(=C(C1=O)Br)C)=O RPJIXRZLQYDQDS-UHFFFAOYSA-N 0.000 description 1
- QRGVGZWQHXGOFJ-UHFFFAOYSA-N 3-butyl-6-methyl-1h-pyrimidine-2,4-dione Chemical compound CCCCN1C(=O)C=C(C)NC1=O QRGVGZWQHXGOFJ-UHFFFAOYSA-N 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- YGEIANYXESJMGO-UHFFFAOYSA-N 3-cyclohexyl-5-(methoxymethyl)-6-methyl-1H-pyrimidine-2,4-dione Chemical compound C1(CCCCC1)N1C(NC(=C(C1=O)COC)C)=O YGEIANYXESJMGO-UHFFFAOYSA-N 0.000 description 1
- XXEOTIKQCHUFHS-UHFFFAOYSA-N 3-cyclohexyl-5-ethyl-6-methyl-1H-pyrimidine-2,4-dione Chemical compound C1(CCCCC1)N1C(NC(=C(C1=O)CC)C)=O XXEOTIKQCHUFHS-UHFFFAOYSA-N 0.000 description 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
- 125000006281 4-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Br)C([H])([H])* 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- JHNRTJRDRWKAIW-UHFFFAOYSA-N 4-chloro-2,6-dimethoxypyrimidine Chemical compound COC1=CC(Cl)=NC(OC)=N1 JHNRTJRDRWKAIW-UHFFFAOYSA-N 0.000 description 1
- 125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 description 1
- LTKWKNOHGYIWLK-UHFFFAOYSA-N 5,6-dichloro-3-methyl-1h-pyrimidine-2,4-dione Chemical compound CN1C(=O)NC(Cl)=C(Cl)C1=O LTKWKNOHGYIWLK-UHFFFAOYSA-N 0.000 description 1
- CUMDKCDRXVXPRO-UHFFFAOYSA-N 5-(chloromethyl)-6-methyl-3-propan-2-yl-1H-pyrimidine-2,4-dione Chemical compound ClCC=1C(N(C(NC1C)=O)C(C)C)=O CUMDKCDRXVXPRO-UHFFFAOYSA-N 0.000 description 1
- AKPATAVUEYOGRE-UHFFFAOYSA-N 5-bromo-3,6-dimethyl-1h-pyrimidine-2,4-dione Chemical compound CC=1NC(=O)N(C)C(=O)C=1Br AKPATAVUEYOGRE-UHFFFAOYSA-N 0.000 description 1
- XRFAQGSXBCLSCV-UHFFFAOYSA-N 5-bromo-3-(3,4-dimethylphenyl)-6-methyl-1H-pyrimidine-2,4-dione Chemical compound BrC=1C(N(C(NC1C)=O)C1=CC(=C(C=C1)C)C)=O XRFAQGSXBCLSCV-UHFFFAOYSA-N 0.000 description 1
- IPHQRMUQMXBNDQ-UHFFFAOYSA-N 5-bromo-3-(4-bromophenyl)-6-methyl-1H-pyrimidine-2,4-dione Chemical compound BrC1=CC=C(C=C1)N1C(NC(=C(C1=O)Br)C)=O IPHQRMUQMXBNDQ-UHFFFAOYSA-N 0.000 description 1
- JOTIEXKOYIPCPO-UHFFFAOYSA-N 5-bromo-3-[(4-chlorophenyl)methyl]-6-methyl-1H-pyrimidine-2,4-dione Chemical compound ClC1=CC=C(CN2C(NC(=C(C2=O)Br)C)=O)C=C1 JOTIEXKOYIPCPO-UHFFFAOYSA-N 0.000 description 1
- YRGXEJVDHNONRH-UHFFFAOYSA-N 5-bromo-6-(bromomethyl)-3-propan-2-yl-1H-pyrimidine-2,4-dione Chemical compound C(C)(C)N1C(NC(=C(C1=O)Br)CBr)=O YRGXEJVDHNONRH-UHFFFAOYSA-N 0.000 description 1
- LGTWEYMOUWQCMS-UHFFFAOYSA-N 5-bromo-6-methyl-3-pentan-3-yl-1h-pyrimidine-2,4-dione Chemical compound CCC(CC)N1C(=O)NC(C)=C(Br)C1=O LGTWEYMOUWQCMS-UHFFFAOYSA-N 0.000 description 1
- QMASYZYAMUINDL-UHFFFAOYSA-N 5-bromo-6-methyl-3-phenyl-1h-pyrimidine-2,4-dione Chemical compound O=C1C(Br)=C(C)NC(=O)N1C1=CC=CC=C1 QMASYZYAMUINDL-UHFFFAOYSA-N 0.000 description 1
- XIVHXZXOHDQSJG-UHFFFAOYSA-N 5-bromo-6-methyl-3-pyridin-3-yl-1H-pyrimidine-2,4-dione Chemical compound N1=CC(=CC=C1)N1C(NC(=C(C1=O)Br)C)=O XIVHXZXOHDQSJG-UHFFFAOYSA-N 0.000 description 1
- ZDDFKQAZGQHHMC-UHFFFAOYSA-N 5-chloro-6-(chloromethyl)-3-cyclohexyl-1H-pyrimidine-2,4-dione Chemical compound ClC=1C(N(C(NC1CCl)=O)C1CCCCC1)=O ZDDFKQAZGQHHMC-UHFFFAOYSA-N 0.000 description 1
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- VLJRRJCHGADELF-UHFFFAOYSA-N 5-chloro-6-methyl-3-propan-2-yl-1-(2,2,2-trichloroacetyl)pyrimidine-2,4-dione Chemical compound C(C)(C)N1C(N(C(=C(C1=O)Cl)C)C(C(Cl)(Cl)Cl)=O)=O VLJRRJCHGADELF-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
- C07D239/20—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D239/22—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to ring carbon atoms
-
- 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
-
- 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
-
- 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
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
- C07D239/96—Two oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6509—Six-membered rings
- C07F9/6512—Six-membered rings having the nitrogen atoms in positions 1 and 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (15)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US83370459A | 1959-08-14 | 1959-08-14 | |
| US83370559A | 1959-08-14 | 1959-08-14 | |
| US1295960A | 1960-03-07 | 1960-03-07 | |
| US1296860A | 1960-03-07 | 1960-03-07 | |
| US1295860A | 1960-03-07 | 1960-03-07 | |
| US1296760A | 1960-03-07 | 1960-03-07 | |
| US1295660A | 1960-03-07 | 1960-03-07 | |
| US1295760A | 1960-03-07 | 1960-03-07 | |
| US4883760A | 1960-08-11 | 1960-08-11 | |
| US8498061A | 1961-01-26 | 1961-01-26 | |
| US8967461A | 1961-02-16 | 1961-02-16 | |
| US12363661A | 1961-07-13 | 1961-07-13 | |
| US15974661A | 1961-12-15 | 1961-12-15 | |
| US232311A US3235360A (en) | 1959-08-14 | 1962-10-22 | Control of undesirable vegetation |
| US284835A US3254082A (en) | 1959-08-14 | 1963-06-03 | Process for preparing substituted uracils |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1240698C2 DE1240698C2 (de) | 1973-01-04 |
| DE1240698B true DE1240698B (US20110009641A1-20110113-C00116.png) | 1973-01-04 |
Family
ID=27585449
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19601240698 Expired DE1240698C2 (de) | 1959-08-14 | 1960-08-12 | Unkrautbekaempfungsmittel |
Country Status (12)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2177869A2 (US20110009641A1-20110113-C00116.png) * | 1972-03-24 | 1973-11-09 | American Cyanamid Co |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL272286A (US20110009641A1-20110113-C00116.png) * | 1960-12-27 | |||
| US3330640A (en) * | 1964-05-27 | 1967-07-11 | Du Pont | Method for the control of undesirable vegetation |
| US3436207A (en) * | 1965-02-23 | 1969-04-01 | Du Pont | Control of undesirable vegetation |
| US3462435A (en) * | 1966-11-15 | 1969-08-19 | United States Borax Chem | Alkyleneiminoquinazoline-2,4-diones |
| US3516816A (en) * | 1967-05-19 | 1970-06-23 | United States Borax Chem | Herbicidal compositions and methods utilizing alkyleneiminourea compounds |
| US3532699A (en) * | 1968-07-12 | 1970-10-06 | Du Pont | Herbicidal poly uracils |
| US3471282A (en) * | 1968-07-12 | 1969-10-07 | Du Pont | Herbicidal compositions containing poly uracils |
| US3539333A (en) * | 1968-08-21 | 1970-11-10 | Gulf Research Development Co | Combating weeds in sugar beets |
| US3931171A (en) * | 1970-02-05 | 1976-01-06 | Bayer Aktiengesellschaft | Process for the production of 2,3-dihydro-1,3-oxazinedione-(2,4)-compounds |
| US3869275A (en) * | 1970-12-04 | 1975-03-04 | Schering Ag | Herbicidal mixtures |
| US4111681A (en) * | 1976-09-09 | 1978-09-05 | E. I. Du Pont De Nemours And Company | Cycloalkanapyrazole-3-carbonitrile herbicides |
| US4189366A (en) * | 1979-01-15 | 1980-02-19 | Eastman Kodak Company | Radiation curable compositions containing 5-halo-6-halomethyluracil derivatives as photoinitiators |
| FR2498894A1 (fr) * | 1981-02-04 | 1982-08-06 | Lecalvez Robert | Desherbant selectif a base de lenacile et de neburon |
| DK366887A (da) * | 1986-07-31 | 1988-05-13 | Hoffmann La Roche | Pyrimidinderivater |
| EP0260621A3 (de) * | 1986-09-18 | 1989-03-15 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | 3-Aryluracil-enoläther und deren Verwendung zur Unkrautbekämpfung |
| HU203542B (en) * | 1987-09-23 | 1991-08-28 | Hoffmann La Roche | Herbicide compositions containing pyrimidinyl-benzamide derivatives and process for producing the active components |
| US5149810A (en) * | 1988-04-22 | 1992-09-22 | Imperial Chemical Industries Plc | Pyrimidine compounds |
| DE68916315T2 (de) * | 1988-04-22 | 1994-10-06 | Zeneca Ltd | Pyrimidinon-Derivate. |
| EP0354179B1 (de) * | 1988-07-29 | 1994-08-17 | Ciba-Geigy Ag | Thiouracile als Stabilisatoren für chlorhaltige Polymerisate |
| GB8908638D0 (en) * | 1989-04-17 | 1989-06-01 | Ici Plc | Novel compounds |
| DK0436680T3 (da) * | 1989-06-29 | 1994-10-10 | Ciba Geigy Ag | Heterocycliske forbindelser |
| US5310723A (en) * | 1993-08-05 | 1994-05-10 | Fmc Corporation | Herbicidal 3-(1-substituted-quinolin-2-on-7-yl)-1-substituted-6-trifluoromethyluracils |
| US5391541A (en) * | 1993-08-11 | 1995-02-21 | Fmc Corporation | Herbicidal 3-(substituted-benzyl)-1-methyl-6-trifluoromethyluracils |
| US6344460B1 (en) | 1999-03-19 | 2002-02-05 | Lonza Inc. | Propynyl uracils |
| US6409988B1 (en) | 1999-07-01 | 2002-06-25 | 3-Dimensional Pharmaceuticals, Inc. | Radiolabeled 1-aryl pyrazoles, the synthesis thereof and the use thereof as pest GABA receptor ligands |
| US6506784B1 (en) | 1999-07-01 | 2003-01-14 | 3-Dimensional Pharmaceuticals, Inc. | Use of 1,3-substituted pyrazol-5-yl sulfonates as pesticides |
| AU6116800A (en) | 1999-07-22 | 2001-02-13 | 3-Dimensional Pharmaceuticals, Inc. | 1-aryl-3-thioalkyl pyrazoles, the synthesis thereof and the use thereof as insecticides |
| WO2001025241A2 (en) | 1999-10-06 | 2001-04-12 | 3-Dimensional Pharmaceuticals, Inc. | Fused 1-(2,6-dichloro-4-trifluoromethylphenyl)-pyrazoles, the synthesis thereof and the use thereof as pesticides |
| EP2052608A1 (de) | 2007-10-24 | 2009-04-29 | Bayer CropScience AG | Herbizid-Kombination |
| EP2090166A1 (de) | 2008-02-14 | 2009-08-19 | Bayer CropScience AG | Flüssige herbizide Zubereitungen |
| DE102008037631A1 (de) | 2008-08-14 | 2010-02-18 | Bayer Cropscience Ag | Herbizid-Kombination mit Dimethoxytriazinyl-substituierten Difluormethansulfonylaniliden |
| CN114656408A (zh) * | 2022-04-12 | 2022-06-24 | 药源药物化学（上海）有限公司 | 一种植物保护剂中间体的合成工艺 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE815192C (de) * | 1949-04-01 | 1951-10-01 | Us Rubber Co | Das Pflanzenwachstum regulierende und phytocide Mittel |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2937175A (en) * | 1960-05-17 | Preparation of orotic acid | ||
| US2567651A (en) * | 1951-09-11 | J-dialkyl-g-amino-l | ||
| US2444024A (en) * | 1948-06-29 | Sydney archer | ||
| US2899435A (en) * | 1959-08-11 | S-neopentyl s-aixyl barbituric acid | ||
| US2688020A (en) * | 1952-01-17 | 1954-08-31 | American Cyanamid Co | Preparation of dihydrouracils |
| US2820035A (en) * | 1953-10-07 | 1958-01-14 | Boehringer Sohn Ingelheim | Barbituric acid derivatives |
| BE553585A (US20110009641A1-20110113-C00116.png) * | 1955-12-21 | |||
| NL99656C (US20110009641A1-20110113-C00116.png) * | 1956-04-04 | |||
| US3078154A (en) * | 1956-11-07 | 1963-02-19 | Geigy Ag J R | Method for inhibiting the growth of plants |
| US2969364A (en) * | 1957-12-26 | 1961-01-24 | Upjohn Co | Derivatives of 5-amino uracil |
| US3002975A (en) * | 1958-08-25 | 1961-10-03 | Diamond Alkali Co | Process for the preparation of 1,3-dihalo-uracils |
| US3086854A (en) * | 1959-02-05 | 1963-04-23 | Du Pont | Method for the control of plant growth |
-
0
- CA CA731651A patent/CA731651A/en not_active Expired
- IT IT635567D patent/IT635567A/it unknown
- NL NL254838D patent/NL254838A/xx unknown
- BE BE594076D patent/BE594076A/xx unknown
- DK DK106253D patent/DK106253A/da unknown
-
1960
- 1960-08-12 SE SE7792/60A patent/SE305770B/xx unknown
- 1960-08-12 DE DE19601240698 patent/DE1240698C2/de not_active Expired
- 1960-08-13 CH CH921360A patent/CH482402A/de not_active IP Right Cessation
- 1960-08-15 GB GB28141/60A patent/GB968661A/en not_active Expired
- 1960-08-15 GB GB17417/64A patent/GB968663A/en not_active Expired
-
1962
- 1962-10-22 US US232311A patent/US3235360A/en not_active Expired - Lifetime
-
1963
- 1963-06-03 US US284835A patent/US3254082A/en not_active Expired - Lifetime
-
1965
- 1965-07-20 BR BR171453/65A patent/BR6571453D0/pt unknown
- 1965-12-31 MY MY1965102A patent/MY6500102A/xx unknown
- 1965-12-31 MY MY1965116A patent/MY6500116A/xx unknown
- 1965-12-31 MY MY1965103A patent/MY6500103A/xx unknown
- 1965-12-31 MY MY1965115A patent/MY6500115A/xx unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE815192C (de) * | 1949-04-01 | 1951-10-01 | Us Rubber Co | Das Pflanzenwachstum regulierende und phytocide Mittel |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2177869A2 (US20110009641A1-20110113-C00116.png) * | 1972-03-24 | 1973-11-09 | American Cyanamid Co |
Also Published As
| Publication number | Publication date |
|---|---|
| GB968663A (en) | 1964-09-02 |
| GB968661A (en) | 1964-09-02 |
| US3254082A (en) | 1966-05-31 |
| BE594076A (US20110009641A1-20110113-C00116.png) | 1900-01-01 |
| NL254838A (US20110009641A1-20110113-C00116.png) | 1900-01-01 |
| DK106253A (US20110009641A1-20110113-C00116.png) | 1900-01-01 |
| CH482402A (de) | 1969-12-15 |
| CA731651A (en) | 1966-04-05 |
| US3235360A (en) | 1966-02-15 |
| MY6500115A (en) | 1965-12-31 |
| SE305770B (US20110009641A1-20110113-C00116.png) | 1968-11-04 |
| BR6571453D0 (pt) | 1973-05-10 |
| MY6500102A (en) | 1965-12-31 |
| IT635567A (US20110009641A1-20110113-C00116.png) | 1900-01-01 |
| DE1240698C2 (de) | 1973-01-04 |
| MY6500103A (en) | 1965-12-31 |
| MY6500116A (en) | 1965-12-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| E77 | Valid patent as to the heymanns-index 1977 |