GB968661A - Herbicidal compositions containing 3-substituted uracils - Google Patents
Herbicidal compositions containing 3-substituted uracilsInfo
- Publication number
- GB968661A GB968661A GB28141/60A GB2814160A GB968661A GB 968661 A GB968661 A GB 968661A GB 28141/60 A GB28141/60 A GB 28141/60A GB 2814160 A GB2814160 A GB 2814160A GB 968661 A GB968661 A GB 968661A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- hydrogen
- compounds
- substituted
- methyl
- 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
- 239000000203 mixture Substances 0.000 title abstract 5
- 230000002363 herbicidal effect Effects 0.000 title abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 14
- 150000001875 compounds Chemical class 0.000 abstract 12
- 229910052739 hydrogen Inorganic materials 0.000 abstract 12
- 239000001257 hydrogen Substances 0.000 abstract 12
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract 9
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 9
- 150000003839 salts Chemical class 0.000 abstract 9
- 238000006243 chemical reaction Methods 0.000 abstract 7
- 150000002431 hydrogen Chemical group 0.000 abstract 6
- 229910052751 metal Inorganic materials 0.000 abstract 6
- 239000002184 metal Substances 0.000 abstract 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 4
- -1 alkali metal salts Chemical class 0.000 abstract 4
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 4
- 239000002585 base Substances 0.000 abstract 4
- 239000000460 chlorine Chemical group 0.000 abstract 4
- 229910052801 chlorine Inorganic materials 0.000 abstract 4
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 4
- 239000003085 diluting agent Substances 0.000 abstract 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 4
- 239000003921 oil Substances 0.000 abstract 4
- 235000019198 oils Nutrition 0.000 abstract 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 4
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 abstract 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 3
- 239000005864 Sulphur Chemical group 0.000 abstract 3
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 abstract 3
- 125000004849 alkoxymethyl group Chemical group 0.000 abstract 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 3
- 229910052794 bromium Chemical group 0.000 abstract 3
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 150000002367 halogens Chemical group 0.000 abstract 3
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 abstract 3
- 230000020477 pH reduction Effects 0.000 abstract 3
- 125000000858 thiocyanato group Chemical group *SC#N 0.000 abstract 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- 230000015572 biosynthetic process Effects 0.000 abstract 2
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 abstract 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 abstract 2
- 239000004202 carbamide Substances 0.000 abstract 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- 239000004009 herbicide Substances 0.000 abstract 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 abstract 2
- 239000007788 liquid Substances 0.000 abstract 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 2
- QYPPRTNMGCREIM-UHFFFAOYSA-N methylarsonic acid Chemical compound C[As](O)(O)=O QYPPRTNMGCREIM-UHFFFAOYSA-N 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- ISEUFVQQFVOBCY-UHFFFAOYSA-N prometon Chemical compound COC1=NC(NC(C)C)=NC(NC(C)C)=N1 ISEUFVQQFVOBCY-UHFFFAOYSA-N 0.000 abstract 2
- 150000003254 radicals Chemical class 0.000 abstract 2
- 238000006798 ring closing metathesis reaction Methods 0.000 abstract 2
- 239000007787 solid Substances 0.000 abstract 2
- 239000004094 surface-active agent Substances 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea group Chemical group NC(=S)N UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 abstract 2
- 229940035893 uracil Drugs 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- SMYMJHWAQXWPDB-UHFFFAOYSA-N (2,4,5-trichlorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC(Cl)=C(Cl)C=C1Cl SMYMJHWAQXWPDB-UHFFFAOYSA-N 0.000 abstract 1
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 abstract 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 abstract 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- PHMQAUXMGFUICG-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-1,3,3-trimethylurea Chemical compound CN(C)C(=O)N(C)C1=CC=C(Cl)C(Cl)=C1 PHMQAUXMGFUICG-UHFFFAOYSA-N 0.000 abstract 1
- NDUPDOJHUQKPAG-UHFFFAOYSA-M 2,2-Dichloropropanoate Chemical compound CC(Cl)(Cl)C([O-])=O NDUPDOJHUQKPAG-UHFFFAOYSA-M 0.000 abstract 1
- UYGUFXUBSNDUFA-UHFFFAOYSA-N 2,3,5,6-tetrachlorobenzoic acid Chemical compound OC(=O)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl UYGUFXUBSNDUFA-UHFFFAOYSA-N 0.000 abstract 1
- XZIDTOHMJBOSOX-UHFFFAOYSA-N 2,3,6-TBA Chemical compound OC(=O)C1=C(Cl)C=CC(Cl)=C1Cl XZIDTOHMJBOSOX-UHFFFAOYSA-N 0.000 abstract 1
- 239000003559 2,4,5-trichlorophenoxyacetic acid Substances 0.000 abstract 1
- YOYAIZYFCNQIRF-UHFFFAOYSA-N 2,6-dichlorobenzonitrile Chemical compound ClC1=CC=CC(Cl)=C1C#N YOYAIZYFCNQIRF-UHFFFAOYSA-N 0.000 abstract 1
- OVSKIKFHRZPJSS-DOMIDYPGSA-N 2-(2,4-dichlorophenoxy)acetic acid Chemical compound OC(=O)[14CH2]OC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-DOMIDYPGSA-N 0.000 abstract 1
- DUMPKRLSSRTFMY-UHFFFAOYSA-N 2-butan-2-yl-3,4-dinitrophenol Chemical compound CCC(C)C1=C(O)C=CC([N+]([O-])=O)=C1[N+]([O-])=O DUMPKRLSSRTFMY-UHFFFAOYSA-N 0.000 abstract 1
- XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 abstract 1
- UNTNYEOPFVVEBL-UHFFFAOYSA-N 3-cyclohexyl-2,4-dioxo-1H-pyrimidine-6-carboxylic acid Chemical compound C1(CCCCC1)N1C(NC(=CC1=O)C(=O)O)=O UNTNYEOPFVVEBL-UHFFFAOYSA-N 0.000 abstract 1
- MMFYIBXYRXSPMC-UHFFFAOYSA-N 3-cyclohexyl-5-methyl-2,4-dioxo-1H-pyrimidine-6-carboxylic acid Chemical compound C1(CCCCC1)N1C(NC(=C(C1=O)C)C(=O)O)=O MMFYIBXYRXSPMC-UHFFFAOYSA-N 0.000 abstract 1
- TYMRJKKKYZIDFH-UHFFFAOYSA-N 6-chloro-2-n,4-n-bis(3-methoxypropyl)-1,3,5-triazine-2,4-diamine Chemical compound COCCCNC1=NC(Cl)=NC(NCCCOC)=N1 TYMRJKKKYZIDFH-UHFFFAOYSA-N 0.000 abstract 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 abstract 1
- 240000005020 Acaciella glauca Species 0.000 abstract 1
- 102000009027 Albumins Human genes 0.000 abstract 1
- 108010088751 Albumins Proteins 0.000 abstract 1
- XKJMBINCVNINCA-UHFFFAOYSA-N Alfalone Chemical compound CON(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XKJMBINCVNINCA-UHFFFAOYSA-N 0.000 abstract 1
- MDBGGTQNNUOQRC-UHFFFAOYSA-N Allidochlor Chemical compound ClCC(=O)N(CC=C)CC=C MDBGGTQNNUOQRC-UHFFFAOYSA-N 0.000 abstract 1
- GEHMBYLTCISYNY-UHFFFAOYSA-N Ammonium sulfamate Chemical compound [NH4+].NS([O-])(=O)=O GEHMBYLTCISYNY-UHFFFAOYSA-N 0.000 abstract 1
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical class [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 abstract 1
- XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 abstract 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 abstract 1
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 abstract 1
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 abstract 1
- 229920001353 Dextrin Polymers 0.000 abstract 1
- 239000004375 Dextrin Substances 0.000 abstract 1
- 241000196324 Embryophyta Species 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 101100295738 Gallus gallus COR3 gene Proteins 0.000 abstract 1
- 108010010803 Gelatin Proteins 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 240000007049 Juglans regia Species 0.000 abstract 1
- 235000009496 Juglans regia Nutrition 0.000 abstract 1
- 239000005909 Kieselgur Substances 0.000 abstract 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 1
- 239000005983 Maleic hydrazide Substances 0.000 abstract 1
- BGRDGMRNKXEXQD-UHFFFAOYSA-N Maleic hydrazide Chemical compound OC1=CC=C(O)N=N1 BGRDGMRNKXEXQD-UHFFFAOYSA-N 0.000 abstract 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 abstract 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 abstract 1
- LKJPSUCKSLORMF-UHFFFAOYSA-N Monolinuron Chemical compound CON(C)C(=O)NC1=CC=C(Cl)C=C1 LKJPSUCKSLORMF-UHFFFAOYSA-N 0.000 abstract 1
- 239000007832 Na2SO4 Substances 0.000 abstract 1
- CCGPUGMWYLICGL-UHFFFAOYSA-N Neburon Chemical compound CCCCN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 CCGPUGMWYLICGL-UHFFFAOYSA-N 0.000 abstract 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical group O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 abstract 1
- 239000004372 Polyvinyl alcohol Substances 0.000 abstract 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 abstract 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 abstract 1
- 229920002472 Starch Polymers 0.000 abstract 1
- 235000011941 Tilia x europaea Nutrition 0.000 abstract 1
- 241000209140 Triticum Species 0.000 abstract 1
- 235000021307 Triticum Nutrition 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 239000000654 additive Substances 0.000 abstract 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 abstract 1
- 150000004703 alkoxides Chemical class 0.000 abstract 1
- 229920000180 alkyd Polymers 0.000 abstract 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 abstract 1
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 abstract 1
- 239000011230 binding agent Substances 0.000 abstract 1
- 239000008280 blood Substances 0.000 abstract 1
- 210000004369 blood Anatomy 0.000 abstract 1
- 150000001642 boronic acid derivatives Chemical class 0.000 abstract 1
- 235000010216 calcium carbonate Nutrition 0.000 abstract 1
- 239000001506 calcium phosphate Substances 0.000 abstract 1
- 235000011010 calcium phosphates Nutrition 0.000 abstract 1
- 239000000378 calcium silicate Substances 0.000 abstract 1
- 229910052918 calcium silicate Inorganic materials 0.000 abstract 1
- 235000012241 calcium silicate Nutrition 0.000 abstract 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 abstract 1
- QZXCCPZJCKEPSA-UHFFFAOYSA-N chlorfenac Chemical compound OC(=O)CC1=C(Cl)C=CC(Cl)=C1Cl QZXCCPZJCKEPSA-UHFFFAOYSA-N 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 229940061627 chloromethyl methyl ether Drugs 0.000 abstract 1
- CWJSHJJYOPWUGX-UHFFFAOYSA-N chlorpropham Chemical compound CC(C)OC(=O)NC1=CC=CC(Cl)=C1 CWJSHJJYOPWUGX-UHFFFAOYSA-N 0.000 abstract 1
- 239000004927 clay Substances 0.000 abstract 1
- 235000012343 cottonseed oil Nutrition 0.000 abstract 1
- 238000006114 decarboxylation reaction Methods 0.000 abstract 1
- 235000019425 dextrin Nutrition 0.000 abstract 1
- JDXYSCUOABNLIR-UHFFFAOYSA-N diethyl 2-oxobutanedioate Chemical compound CCOC(=O)CC(=O)C(=O)OCC JDXYSCUOABNLIR-UHFFFAOYSA-N 0.000 abstract 1
- 229940071094 diethyl oxalacetate Drugs 0.000 abstract 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 abstract 1
- 229910000397 disodium phosphate Inorganic materials 0.000 abstract 1
- 235000019800 disodium phosphate Nutrition 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- YKOADJNIZPPKRY-UHFFFAOYSA-N ethyl 2-(methylcarbamoylamino)cyclopentene-1-carboxylate Chemical compound C(C)OC(=O)C1=C(CCC1)NC(=O)NC YKOADJNIZPPKRY-UHFFFAOYSA-N 0.000 abstract 1
- 125000004494 ethyl ester group Chemical group 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- XXOYNJXVWVNOOJ-UHFFFAOYSA-N fenuron Chemical compound CN(C)C(=O)NC1=CC=CC=C1 XXOYNJXVWVNOOJ-UHFFFAOYSA-N 0.000 abstract 1
- 235000013312 flour Nutrition 0.000 abstract 1
- 229920000159 gelatin Polymers 0.000 abstract 1
- 239000008273 gelatin Substances 0.000 abstract 1
- 235000019322 gelatine Nutrition 0.000 abstract 1
- 235000011852 gelatine desserts Nutrition 0.000 abstract 1
- 239000003292 glue Substances 0.000 abstract 1
- 230000026030 halogenation Effects 0.000 abstract 1
- 238000005658 halogenation reaction Methods 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- VRNINGUKUJWZTH-UHFFFAOYSA-L lead(2+);dithiocyanate Chemical compound [Pb+2].[S-]C#N.[S-]C#N VRNINGUKUJWZTH-UHFFFAOYSA-L 0.000 abstract 1
- 239000004571 lime Substances 0.000 abstract 1
- 229910052749 magnesium Inorganic materials 0.000 abstract 1
- 239000001095 magnesium carbonate Substances 0.000 abstract 1
- 235000011160 magnesium carbonates Nutrition 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 238000005649 metathesis reaction Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- BMLIZLVNXIYGCK-UHFFFAOYSA-N monuron Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C=C1 BMLIZLVNXIYGCK-UHFFFAOYSA-N 0.000 abstract 1
- 238000006396 nitration reaction Methods 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- WSGCRAOTEDLMFQ-UHFFFAOYSA-N nonan-5-one Chemical compound CCCCC(=O)CCCC WSGCRAOTEDLMFQ-UHFFFAOYSA-N 0.000 abstract 1
- KHPXUQMNIQBQEV-UHFFFAOYSA-L oxaloacetate(2-) Chemical class [O-]C(=O)CC(=O)C([O-])=O KHPXUQMNIQBQEV-UHFFFAOYSA-L 0.000 abstract 1
- 239000008188 pellet Substances 0.000 abstract 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 abstract 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 abstract 1
- 239000003208 petroleum Substances 0.000 abstract 1
- 229920002451 polyvinyl alcohol Polymers 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- VXPLXMJHHKHSOA-UHFFFAOYSA-N propham Chemical compound CC(C)OC(=O)NC1=CC=CC=C1 VXPLXMJHHKHSOA-UHFFFAOYSA-N 0.000 abstract 1
- 235000003499 redwood Nutrition 0.000 abstract 1
- 239000000377 silicon dioxide Substances 0.000 abstract 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 abstract 1
- 229910052938 sodium sulfate Inorganic materials 0.000 abstract 1
- 235000011152 sodium sulphate Nutrition 0.000 abstract 1
- HCJLVWUMMKIQIM-UHFFFAOYSA-M sodium;2,3,4,5,6-pentachlorophenolate Chemical compound [Na+].[O-]C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl HCJLVWUMMKIQIM-UHFFFAOYSA-M 0.000 abstract 1
- 239000008107 starch Substances 0.000 abstract 1
- 235000019698 starch Nutrition 0.000 abstract 1
- 239000000454 talc Substances 0.000 abstract 1
- 229910052623 talc Inorganic materials 0.000 abstract 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 abstract 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical class [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 abstract 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 abstract 1
- 235000020234 walnut Nutrition 0.000 abstract 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
- C07D239/20—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)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB17418/64A GB968664A (en) | 1959-08-14 | 1960-08-15 | 3-substituted uracils |
| GB17419/64A GB968665A (en) | 1959-08-14 | 1960-08-15 | 3-substituted uracils |
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 | |
| US1295760A | 1960-03-07 | 1960-03-07 | |
| US1295660A | 1960-03-07 | 1960-03-07 | |
| US1295860A | 1960-03-07 | 1960-03-07 | |
| US1296860A | 1960-03-07 | 1960-03-07 | |
| US1296760A | 1960-03-07 | 1960-03-07 | |
| US1295960A | 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 (1)
| Publication Number | Publication Date |
|---|---|
| GB968661A true GB968661A (en) | 1964-09-02 |
Family
ID=27585449
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB28141/60A Expired GB968661A (en) | 1959-08-14 | 1960-08-15 | Herbicidal compositions containing 3-substituted uracils |
| GB17417/64A Expired GB968663A (en) | 1959-08-14 | 1960-08-15 | 3-substituted uracils |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB17417/64A Expired GB968663A (en) | 1959-08-14 | 1960-08-15 | 3-substituted uracils |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US3235360A (no) |
| BE (1) | BE594076A (no) |
| BR (1) | BR6571453D0 (no) |
| CA (1) | CA731651A (no) |
| CH (1) | CH482402A (no) |
| DE (1) | DE1240698C2 (no) |
| DK (1) | DK106253A (no) |
| GB (2) | GB968661A (no) |
| IT (1) | IT635567A (no) |
| MY (4) | MY6500116A (no) |
| NL (1) | NL254838A (no) |
| SE (1) | SE305770B (no) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4812164A (en) * | 1986-09-18 | 1989-03-14 | Hoffmann-La Roche Inc. | Herbicidal heterocyclic compounds |
| US4859229A (en) * | 1986-07-31 | 1989-08-22 | Hoffmann-La Roche Inc. | 3-Aryluracils having an ether (thio) carbomyloxy or sulphomyloxy substituent on the aromatic moiety |
| US5017211A (en) * | 1987-09-23 | 1991-05-21 | Ciba-Geigy Corporation | Heterocyclic compounds |
| US5183492A (en) * | 1989-06-29 | 1993-02-02 | Ciba-Geigy Corporation | Herbicidal 3-aryluracils |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE611920A (no) * | 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 |
| US3532686A (en) * | 1967-05-19 | 1970-10-06 | United States Borax Chem | Alkyleneiminourea compounds |
| US3471282A (en) * | 1968-07-12 | 1969-10-07 | Du Pont | Herbicidal compositions containing poly uracils |
| US3532699A (en) * | 1968-07-12 | 1970-10-06 | Du Pont | Herbicidal 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 |
| GB1384506A (en) * | 1972-03-24 | 1975-02-19 | American Cyanamid Co | 2,3,5-substituted-6-trifluoromethyl-1,3-diazin-4-ones |
| 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 |
| DE68916315T2 (de) * | 1988-04-22 | 1994-10-06 | Zeneca Ltd | Pyrimidinon-Derivate. |
| US5149810A (en) * | 1988-04-22 | 1992-09-22 | Imperial Chemical Industries Plc | Pyrimidine compounds |
| DE58908208D1 (de) * | 1988-07-29 | 1994-09-22 | Ciba Geigy Ag | Thiouracile als Stabilisatoren für chlorhaltige Polymerisate. |
| GB8908638D0 (en) * | 1989-04-17 | 1989-06-01 | Ici Plc | Novel compounds |
| 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 |
| US6506784B1 (en) | 1999-07-01 | 2003-01-14 | 3-Dimensional Pharmaceuticals, Inc. | Use of 1,3-substituted pyrazol-5-yl sulfonates as pesticides |
| 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 |
| US6518266B1 (en) | 1999-07-22 | 2003-02-11 | 3-Dimensional Pharmaceuticals | 1- Aryl-3-thioalkyl pyrazoles, the synthesis thereof and the use thereof as insecticides |
| US6545033B1 (en) | 1999-10-06 | 2003-04-08 | 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 |
Family Cites Families (13)
| 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 | ||
| GB693912A (en) * | 1949-04-01 | 1953-07-08 | Us Rubber Co | Plant growth regulants and phytocides |
| 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 (no) * | 1955-12-21 | |||
| NL216005A (no) * | 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
- DK DK106253D patent/DK106253A/da unknown
- IT IT635567D patent/IT635567A/it unknown
- CA CA731651A patent/CA731651A/en not_active Expired
- NL NL254838D patent/NL254838A/xx unknown
- BE BE594076D patent/BE594076A/xx 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 MY1965116A patent/MY6500116A/xx unknown
- 1965-12-31 MY MY1965103A patent/MY6500103A/xx unknown
- 1965-12-31 MY MY1965102A patent/MY6500102A/xx unknown
- 1965-12-31 MY MY1965115A patent/MY6500115A/xx unknown
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4859229A (en) * | 1986-07-31 | 1989-08-22 | Hoffmann-La Roche Inc. | 3-Aryluracils having an ether (thio) carbomyloxy or sulphomyloxy substituent on the aromatic moiety |
| US4812164A (en) * | 1986-09-18 | 1989-03-14 | Hoffmann-La Roche Inc. | Herbicidal heterocyclic compounds |
| US5017211A (en) * | 1987-09-23 | 1991-05-21 | Ciba-Geigy Corporation | Heterocyclic compounds |
| US5183492A (en) * | 1989-06-29 | 1993-02-02 | Ciba-Geigy Corporation | Herbicidal 3-aryluracils |
Also Published As
| Publication number | Publication date |
|---|---|
| IT635567A (no) | 1900-01-01 |
| BR6571453D0 (pt) | 1973-05-10 |
| MY6500116A (en) | 1965-12-31 |
| DE1240698C2 (de) | 1973-01-04 |
| GB968663A (en) | 1964-09-02 |
| NL254838A (no) | 1900-01-01 |
| BE594076A (no) | 1900-01-01 |
| CA731651A (en) | 1966-04-05 |
| DE1240698B (no) | 1973-01-04 |
| MY6500115A (en) | 1965-12-31 |
| DK106253A (no) | 1900-01-01 |
| US3254082A (en) | 1966-05-31 |
| SE305770B (no) | 1968-11-04 |
| MY6500103A (en) | 1965-12-31 |
| MY6500102A (en) | 1965-12-31 |
| CH482402A (de) | 1969-12-15 |
| US3235360A (en) | 1966-02-15 |
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