GB1035092A - Improvements relating to herbicides and novel 3-substituted uracils - Google Patents
Improvements relating to herbicides and novel 3-substituted uracilsInfo
- Publication number
- GB1035092A GB1035092A GB619166A GB619166A GB1035092A GB 1035092 A GB1035092 A GB 1035092A GB 619166 A GB619166 A GB 619166A GB 619166 A GB619166 A GB 619166A GB 1035092 A GB1035092 A GB 1035092A
- Authority
- GB
- United Kingdom
- Prior art keywords
- radical
- carbon atoms
- radical containing
- alkyl
- hydrogen
- 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
- 239000004009 herbicide Substances 0.000 title abstract 4
- -1 cycloalkyl alkyl radical Chemical group 0.000 abstract 28
- 125000004432 carbon atom Chemical group C* 0.000 abstract 24
- 239000001257 hydrogen Substances 0.000 abstract 8
- 229910052739 hydrogen Inorganic materials 0.000 abstract 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 7
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 4
- 239000000460 chlorine Chemical group 0.000 abstract 4
- 229910052801 chlorine Inorganic materials 0.000 abstract 4
- 150000003839 salts Chemical class 0.000 abstract 4
- 239000004094 surface-active agent Substances 0.000 abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 239000003085 diluting agent Substances 0.000 abstract 3
- VOLGAXAGEUPBDM-UHFFFAOYSA-N $l^{1}-oxidanylethane Chemical compound CC[O] VOLGAXAGEUPBDM-UHFFFAOYSA-N 0.000 abstract 2
- QOOQLKSEGVNYLA-UHFFFAOYSA-N 1-$l^{1}-oxidanylbutane Chemical compound CCCC[O] QOOQLKSEGVNYLA-UHFFFAOYSA-N 0.000 abstract 2
- JAVBBFXUGDCHLZ-UHFFFAOYSA-N 1-$l^{1}-oxidanylpropane Chemical compound CCC[O] JAVBBFXUGDCHLZ-UHFFFAOYSA-N 0.000 abstract 2
- WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 abstract 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical class [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 abstract 2
- HLVMZRXHDRXSJY-UHFFFAOYSA-N [CH2]SC Chemical compound [CH2]SC HLVMZRXHDRXSJY-UHFFFAOYSA-N 0.000 abstract 2
- 229910052794 bromium Inorganic materials 0.000 abstract 2
- AOJDZKCUAATBGE-UHFFFAOYSA-N bromomethane Chemical compound Br[CH2] AOJDZKCUAATBGE-UHFFFAOYSA-N 0.000 abstract 2
- WBLIXGSTEMXDSM-UHFFFAOYSA-N chloromethane Chemical compound Cl[CH2] WBLIXGSTEMXDSM-UHFFFAOYSA-N 0.000 abstract 2
- JEVCWSUVFOYBFI-UHFFFAOYSA-N cyanyl Chemical compound N#[C] JEVCWSUVFOYBFI-UHFFFAOYSA-N 0.000 abstract 2
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract 2
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 abstract 2
- 229910052731 fluorine Inorganic materials 0.000 abstract 2
- 239000011737 fluorine Chemical group 0.000 abstract 2
- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 abstract 2
- BLNWTAHYTCHDJH-UHFFFAOYSA-O hydroxy(oxo)azanium Chemical compound O[NH+]=O BLNWTAHYTCHDJH-UHFFFAOYSA-O 0.000 abstract 2
- 229910052740 iodine Chemical group 0.000 abstract 2
- 239000007788 liquid Substances 0.000 abstract 2
- YYOGAOHWUDJBLM-UHFFFAOYSA-N mercaptomethyl radical Chemical compound S[CH2] YYOGAOHWUDJBLM-UHFFFAOYSA-N 0.000 abstract 2
- 239000002184 metal Chemical class 0.000 abstract 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 abstract 2
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- NYAZXHASVIWIRJ-UHFFFAOYSA-N nitridosulfidocarbon(.) Chemical compound [S]C#N NYAZXHASVIWIRJ-UHFFFAOYSA-N 0.000 abstract 2
- 150000003254 radicals Chemical class 0.000 abstract 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- LIEASXBWPXQISE-UHFFFAOYSA-N (4-methoxycyclohexyl)methylurea Chemical compound COC1CCC(CC1)CNC(=O)N LIEASXBWPXQISE-UHFFFAOYSA-N 0.000 abstract 1
- IKNMSBHVNMBGJR-UHFFFAOYSA-N 1-(1-bicyclo[2.2.1]hept-2-enylmethyl)-3-(2,2-dicyanoethenyl)urea Chemical compound C12(C=CC(CC1)C2)CNC(NC=C(C#N)C#N)=O IKNMSBHVNMBGJR-UHFFFAOYSA-N 0.000 abstract 1
- NAFAJFUPGSGMJP-UHFFFAOYSA-N 2-ethylcycloheptan-1-one Chemical compound CCC1CCCCCC1=O NAFAJFUPGSGMJP-UHFFFAOYSA-N 0.000 abstract 1
- QLQXAVYXVOOMCH-UHFFFAOYSA-N 3-[(4-methoxycyclohexyl)methyl]-5-methyl-2,4-dioxo-1H-pyrimidine-6-carboxylic acid Chemical compound C(=O)(O)C1=C(C(N(C(N1)=O)CC1CCC(CC1)OC)=O)C QLQXAVYXVOOMCH-UHFFFAOYSA-N 0.000 abstract 1
- WMEFJYJRLSVFGK-UHFFFAOYSA-N 6-amino-1-(1-bicyclo[2.2.1]hept-2-enylmethyl)-2-oxopyrimidine-5-carbonitrile Chemical compound C12(C=CC(CC1)C2)CN1C(N=CC(=C1N)C#N)=O WMEFJYJRLSVFGK-UHFFFAOYSA-N 0.000 abstract 1
- 239000001692 EU approved anti-caking agent Substances 0.000 abstract 1
- 241000196324 Embryophyta Species 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000005983 Maleic hydrazide Chemical class 0.000 abstract 1
- BGRDGMRNKXEXQD-UHFFFAOYSA-N Maleic hydrazide Chemical class OC1=CC=C(O)N=N1 BGRDGMRNKXEXQD-UHFFFAOYSA-N 0.000 abstract 1
- 239000000853 adhesive Substances 0.000 abstract 1
- 230000001070 adhesive effect Effects 0.000 abstract 1
- 239000002518 antifoaming agent Substances 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical class [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 abstract 1
- 235000013877 carbamide Nutrition 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 150000003982 chlorocarboxylic acids Chemical class 0.000 abstract 1
- 238000005260 corrosion Methods 0.000 abstract 1
- 230000007797 corrosion Effects 0.000 abstract 1
- IRQWLEOSDCDEHQ-UHFFFAOYSA-N cyclopropylmethylurea Chemical compound NC(=O)NCC1CC1 IRQWLEOSDCDEHQ-UHFFFAOYSA-N 0.000 abstract 1
- OQOCQBJWOCRPQY-UHFFFAOYSA-N diethyl 2-methyl-3-oxosuccinate Chemical compound CCOC(=O)C(C)C(=O)C(=O)OCC OQOCQBJWOCRPQY-UHFFFAOYSA-N 0.000 abstract 1
- 239000006185 dispersion Substances 0.000 abstract 1
- 239000000975 dye Substances 0.000 abstract 1
- 239000008187 granular material Substances 0.000 abstract 1
- 239000008233 hard water Substances 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000008188 pellet Substances 0.000 abstract 1
- 150000002989 phenols Chemical class 0.000 abstract 1
- 239000000049 pigment Substances 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000003381 stabilizer Substances 0.000 abstract 1
- 150000003918 triazines Chemical class 0.000 abstract 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 abstract 1
- 150000003672 ureas Chemical class 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Novel compounds of the general formula <FORM:1035092/C2/1> or the corresponding isomeric formula <FORM:1035092/C2/2> wherein R1 represents a cycloalkyl alkyl radical containing 4 to 13 carbon atoms, a cycloalkenyl alkyl radical containing 5 to 13 carbon atoms, a (substituted cycloalkyl)alkyl radical containing 5 to 14 carbon atoms or a (substituted cycloalkenyl)alkyl radical containing 5 to 14 carbon atoms; R2 represents a hydrogen, chlorine, fluorine, bromine or iodine atom, a methyl radical, an ethyl radical, a propyl radical, a butyl radical, a methoxy radical, an ethoxy radical, a propoxy radical, a butoxy radical, a nitro radical, an alkoxymethyl radical containing 2 to 6 carbon atoms, a hydroxy alkyl radical containing 1 to 6 carbon atoms, an alkenyl radical containing 3 to 6 carbon atoms, a thiocyanato radical, a cyano radical, a mercaptomethyl radical, a methylthiomethyl radical, a phenylthiomethyl radical, an alkylthio radical containing 1 to 4 carbon atoms, a bromomethyl radical, a fluoromethyl radical, a chloromethyl radical or a carboxymethylthiomethyl radical; R3 represents a hydrogen, chlorine or bromine atom, an alkyl radical containing 1 to 5 carbon atoms, a chloroalkyl radical containing 1 to 4 carbon atoms, a bromoalkyl radical containing 1 to 4 carbon atoms, or an alkoxy radical containing 1 to 5 carbon atoms; or R2 and R3 together represent a divalent alkylene radical of formula (CH2)n, where n is 3, 4 or 5; with the proviso that if R2 represents hydrogen, R3 represents hydrogen or C1- 5 alkyl; and X represents an oxygen or sulphur atom or a metal salt thereof, are prepared by methods known for the production of uracils, e.g. those disclosed in 968,661. These compounds are herbicides (see Division A5). Intermediates. - Ethyl 2 - (3 - cyclopropylmethylureido) - 1 - cycloheptene - 1 - carboxylate is prepared from cyclopropylmethyl urea and ethyl 2 - cycloheptanone - 1 - carboxylate. 6 - Carboxy -3 - (4 - methoxycyclohexylmethyl)-5-methyluracil is prepared from 1-(4-methoxycyclohexylmethyl) urea and diethyl 2-methyloxalacetate. [(3 - Norbornenylmethylureido)-methylene]malononitrile is prepared from norbornenylmethylurea, malononitrile and triethyl orthoformate; with methanolic NaOMe, followed by acetic acid, it gives 3-norbornenylmethyl-5-cyanocytosine.ALSO:Compounds of the general formula: <FORM:1035092/A5-A6/1> or the corresponding isomeric formula: <FORM:1035092/A5-A6/2> wherein R1 represents a cycloalkyl alkyl radical containing 4 to 13 carbon atoms, a cycloalkenyl alkyl radical containing 5 to 13 carbon atoms, a (substituted cycloalkyl)alkyl radical containing 5 to 14 carbon atoms or a (substituted cycloalkenyl) alkyl radical containing 5 to 14 carbon atoms; R2 represents a hydrogen, chlorine, fluorine, bromine or iodine atom, a methyl radical, an ethyl radical, a propyl radical, a butyl radical, a methoxy radical, an ethoxy radical, a propoxy radical, a butoxy radical, a nitro radical, an alkoxymethyl radical containing 2 to 6 carbon atoms, a hydroxy alkyl radical containing 1 to 6 carbon atoms, an alkenyl radical containing 3 to 6 carbon atoms, a thiocyanato radical, a cyano radical, a mercaptomethyl radical, a methylthiomethyl radical, a phenylthiomethyl radical, an alkylthio radical containing 1 to 4 carbon atoms, a bromomethyl radical, a fluoromethyl radical, a chloromethyl radical or a carboxymethylthiomethyl radical; R3 represents a hydrogen, chlorine or bromine atom, an alkyl radical containing 1 to 5 carbon atoms, a chloroalkyl radical containing 1 to 4 carbon atoms a bromoalkyl radical containing 1 to 4 carbon atoms, or an alkoxy radical containing 1 to 5 carbon atoms; or R2 and R3 together represent a divalent alkylene radical of formula (CH2)n, where n is 3, 4 or 5; with the proviso that if R2 represents hydrogen, R3 represent hydrogen or C1-5 alkyl; and X represents an oxyten or sulphur atom or a metal salt thereof, are used to control the growth of weeds, e.g. in a composition containing additionally (i) a diluent which is at least in part an oil (defined as a liquid immiscible with water and soluble in ether, and boiling at not below 125 DEG C), with or without a surface-active agent; (ii) a diluent which is at least in part a solid, with or without a surface-active agent; (iii) a surface-active agent and a diluent which is a liquid other than an oil, e.g. water; or (iv) a surface-active agent. The compositions may be in the form of solutions, dispersions, powders or dusts, granules or pellets, and may contain adhesives, corrosion inhibitors, antifoam agents, dyes, pigments, anticaking agents, hard water stabilizers and other herbicides, e.g. those of Specifications 1,035,091, 1,035,093, 1,035,094, 1,035,095, 1,035,096, 1,035,097 or 1,035,098, or substituted ureas, substituted triazines, phenols, chloro-carboxylic acids and their derivatives, substituted carbamic acid derivatives, maleic hydrazide, inorganic salts, mixed inorganic-organic salts, or other specified herbicides.
Applications Claiming Priority (19)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US83370459A | 1959-08-14 | 1959-08-14 | |
| US83370559A | 1959-08-14 | 1959-08-14 | |
| US1295660A | 1960-03-07 | 1960-03-07 | |
| US1295860A | 1960-03-07 | 1960-03-07 | |
| US1295760A | 1960-03-07 | 1960-03-07 | |
| US1295960A | 1960-03-07 | 1960-03-07 | |
| US1296760A | 1960-03-07 | 1960-03-07 | |
| US1296860A | 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 | |
| US16743462A | 1962-01-19 | 1962-01-19 | |
| US217521A US3235357A (en) | 1959-08-14 | 1962-08-17 | Method for the control of undesirable vegetation |
| US221890A US3235358A (en) | 1962-09-06 | 1962-09-06 | Control of undesirable vegetation |
| US232311A US3235360A (en) | 1959-08-14 | 1962-10-22 | Control of undesirable vegetation |
| US233952A US3235361A (en) | 1962-10-29 | 1962-10-29 | Method for the control of undesirable vegetation |
| US284835A US3254082A (en) | 1959-08-14 | 1963-06-03 | Process for preparing substituted uracils |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1035092A true GB1035092A (en) | 1966-07-06 |
Family
ID=27586287
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB619166A Expired GB1035092A (en) | 1959-08-14 | 1962-12-07 | Improvements relating to herbicides and novel 3-substituted uracils |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1035092A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5077297A (en) * | 1988-04-22 | 1991-12-31 | Imperial Chemical Industries Plc | Novel compounds |
| US5104878A (en) * | 1989-04-17 | 1992-04-14 | Imperial Chemical Industries Plc | 1-phenyl-6-one-pyrimidine derivatives |
| US5149810A (en) * | 1988-04-22 | 1992-09-22 | Imperial Chemical Industries Plc | Pyrimidine compounds |
-
1962
- 1962-12-07 GB GB619166A patent/GB1035092A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5077297A (en) * | 1988-04-22 | 1991-12-31 | Imperial Chemical Industries Plc | Novel compounds |
| US5149810A (en) * | 1988-04-22 | 1992-09-22 | Imperial Chemical Industries Plc | Pyrimidine compounds |
| US5104878A (en) * | 1989-04-17 | 1992-04-14 | Imperial Chemical Industries Plc | 1-phenyl-6-one-pyrimidine derivatives |
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