GB968663A - 3-substituted uracils - Google Patents
3-substituted uracilsInfo
- Publication number
- GB968663A GB968663A GB17417/64A GB1741764A GB968663A GB 968663 A GB968663 A GB 968663A GB 17417/64 A GB17417/64 A GB 17417/64A GB 1741764 A GB1741764 A GB 1741764A GB 968663 A GB968663 A GB 968663A
- Authority
- GB
- United Kingdom
- Prior art keywords
- give
- methyl
- reaction
- salt
- ethyl
- 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
- 150000001875 compounds Chemical class 0.000 abstract 7
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 abstract 6
- 229910052700 potassium Inorganic materials 0.000 abstract 6
- 229910052708 sodium Inorganic materials 0.000 abstract 6
- 239000011734 sodium Substances 0.000 abstract 6
- 238000006243 chemical reaction Methods 0.000 abstract 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 5
- 150000003839 salts Chemical class 0.000 abstract 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 4
- 229910052744 lithium Inorganic materials 0.000 abstract 4
- 239000000203 mixture Substances 0.000 abstract 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- 239000002585 base Substances 0.000 abstract 3
- 229910052794 bromium Inorganic materials 0.000 abstract 3
- 239000000460 chlorine Chemical group 0.000 abstract 3
- 229910052801 chlorine Inorganic materials 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 abstract 3
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 abstract 3
- 229940035893 uracil Drugs 0.000 abstract 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 239000003085 diluting agent Substances 0.000 abstract 2
- 239000007788 liquid Substances 0.000 abstract 2
- 229910003002 lithium salt Inorganic materials 0.000 abstract 2
- 159000000002 lithium salts Chemical class 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 2
- 230000020477 pH reduction Effects 0.000 abstract 2
- 239000011591 potassium Substances 0.000 abstract 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 abstract 2
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 abstract 2
- ZGERASBLGZFFOY-UHFFFAOYSA-N 2-(cyclopentylcarbamoylamino)cyclopentene-1-carboxylic acid Chemical compound C1(CCCC1)NC(NC1=C(CCC1)C(=O)O)=O ZGERASBLGZFFOY-UHFFFAOYSA-N 0.000 abstract 1
- BQIRNRIZIZRGCN-UHFFFAOYSA-N 3-cyclohexyl-6-methyl-1h-pyrimidine-2,4-dione Chemical compound O=C1NC(C)=CC(=O)N1C1CCCCC1 BQIRNRIZIZRGCN-UHFFFAOYSA-N 0.000 abstract 1
- 241000196324 Embryophyta Species 0.000 abstract 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 1
- 239000000654 additive Substances 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- -1 alkali metal methoxide Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 230000031709 bromination Effects 0.000 abstract 1
- 238000005893 bromination reaction Methods 0.000 abstract 1
- 239000004202 carbamide Substances 0.000 abstract 1
- 238000005660 chlorination reaction Methods 0.000 abstract 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 abstract 1
- CBEYJGNJOCTQGW-UHFFFAOYSA-N cyclopentylurea Chemical compound NC(=O)NC1CCCC1 CBEYJGNJOCTQGW-UHFFFAOYSA-N 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 230000002363 herbicidal effect Effects 0.000 abstract 1
- 239000004009 herbicide Substances 0.000 abstract 1
- 239000004615 ingredient Substances 0.000 abstract 1
- 235000011007 phosphoric acid Nutrition 0.000 abstract 1
- 238000006798 ring closing metathesis reaction Methods 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000004094 surface-active agent Substances 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)
Abstract
The invention comprises compounds of the isomeric formulae: <FORM:0968663/C1/1> or <FORM:0968663/C1/2> where R1 is C5-8 cycloalkyl, R2 is hydrogen, bromine, chlorine, methyl, ethyl, hydroxymethyl, methoxymethyl or methoxy and R3 is methyl or ethyl, or R2 and R3 together represent a trimethylene or tetramethylene group, and the sodium, potassium and lithium salts thereof. 3-Cyclohexyl-6-methyluracil and its salts are disclaimed. The compounds of the invention are herbicides (see Division A5). Exemplified methods of producing such compounds are chlorination or bromination of compounds in which R2 is hydrogen to give R2 as Cl or Br; reaction of a urea R1NHCONH2 with an ester R1OCOCHR2COR3, where R1 is C1-6\t alkyl, to give R1NHCONHCR3=CH2COOR1, and heating this under substantially anhydrous conditions in the presence of a base to give the Na, K or Li salt of the uracil, followed by acidification if required; reaction of a compound with R2 as H with formaldehyde to give R2 as hydroxymethyl; reaction of a compound with R2 as chloromethyl with an alkali metal methoxide to give R2 as methoxymethyl; reaction of R1NCO with R3C(NH2)=CHCOOC2H5 followed by ring closure with a base and acidification; and reaction of a uracil as defined with a suitable base to give the Na, K or Li salt. 2-(3-Cyclopentylureido)-1-cyclopentene carboxylic acidmethyl ester is obtained from cyclopentylurea and methyl 2-cyclopentanone-1-carboxylate with H3PO4. Specifications 492,742, 968,662, 968,664, 968,665 and 968,666 also are referred to.ALSO:The invention comprises herbicidal compositions comprising at least one compound of the isomeric formul <FORM:0968663/A5-A6/1> or <FORM:0968663/A5-A6/2> where R1 is C5-8 cycloalkyl, R2 is hydrogen, bromine, chlorine, methyl, ethyl, hydroxymethyl, methoxymethyl or methoxy and R3 is methyl or ethyl, or R2 and R3 together represent a trimethylene or tetramethylene group, or a sodium, potassium or lithium salt thereof (see Division C2), associated with a compatible diluent, which may be (i) at least in part a liquid other than an oil, e.g. water; (ii) at least in part an oil (see below); (iii) at least in part a solid; or (iv) a surface-active agent (which may also be present in (i)-(iii)). Compositions consisting of (i.e. with no other ingredients) 3-cyclocohexyl-6-methyluracil or a Na, K or Li salt thereof and water and/or methanol are disclaimed. The invention also comprises a method of controlling the growth of weeds at a locus by applying to the locus a herbicidally effective quantity of at least one uracil as defined above or a Na, K or Li salt thereof, if desired in the form of a composition as defined. An oil is defined as a liquid immiscible with water and soluble in ether, and which boils at not below 125 DEG C. Specified diluents and additives are those referred to in the parent Specification. The compositions may also contain one of the 3-substituted uracils disclosed in Specifications 968,662, 968,665 and 968,666. Specification 492,742 also is referred to.
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 | |
| US1295660A | 1960-03-07 | 1960-03-07 | |
| US1295760A | 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 | |
| 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 |
|---|---|
| GB968663A true GB968663A (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 Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB28141/60A Expired GB968661A (en) | 1959-08-14 | 1960-08-15 | Herbicidal compositions containing 3-substituted uracils |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US3235360A (en) |
| BE (1) | BE594076A (en) |
| BR (1) | BR6571453D0 (en) |
| CA (1) | CA731651A (en) |
| CH (1) | CH482402A (en) |
| DE (1) | DE1240698C2 (en) |
| DK (1) | DK106253A (en) |
| GB (2) | GB968661A (en) |
| IT (1) | IT635567A (en) |
| MY (4) | MY6500115A (en) |
| NL (1) | NL254838A (en) |
| SE (1) | SE305770B (en) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE611920A (en) * | 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 |
| 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 |
| ZA731789B (en) * | 1972-03-24 | 1973-12-19 | 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 (en) * | 1981-02-04 | 1982-08-06 | Lecalvez Robert | Herbicidal compsns. contg. lenacil and a urea (deriv.) - esp. for treatment of ornamental shrubs and conifers |
| DK366887A (en) * | 1986-07-31 | 1988-05-13 | Hoffmann La Roche | pyrimidine |
| EP0260621A3 (en) * | 1986-09-18 | 1989-03-15 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | 3-aryl uracil-enol ethers and their use as herbicides |
| AU2328188A (en) * | 1987-09-23 | 1989-04-18 | Ciba-Geigy Ag | Heterocyclic compounds |
| US5149810A (en) * | 1988-04-22 | 1992-09-22 | Imperial Chemical Industries Plc | Pyrimidine compounds |
| GB8906946D0 (en) * | 1988-04-22 | 1989-05-10 | Ici Plc | Novel compounds |
| DE58908208D1 (en) * | 1988-07-29 | 1994-09-22 | Ciba Geigy Ag | Thiouracile as stabilizers for chlorine-containing polymers. |
| GB8908638D0 (en) * | 1989-04-17 | 1989-06-01 | Ici Plc | Novel compounds |
| WO1991000278A1 (en) * | 1989-06-29 | 1991-01-10 | Ciba-Geigy Ag | Heterocyclic 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 |
| 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 |
| AU7865000A (en) | 1999-10-06 | 2001-05-10 | 3-Dimensional Pharmaceuticals, Inc. | Fused 1-(2,6-dichloro-4-trifluoromethylphenyl)-pyrazoles, the synthesis thereof and the use thereof as pesticides |
| EP2052608A1 (en) | 2007-10-24 | 2009-04-29 | Bayer CropScience AG | Herbicide combination |
| EP2090166A1 (en) | 2008-02-14 | 2009-08-19 | Bayer CropScience AG | Liquid herbicidal preparations |
| DE102008037631A1 (en) | 2008-08-14 | 2010-02-18 | Bayer Cropscience Ag | Herbicide combination with dimethoxytriazinyl-substituted difluoromethanesulfonylanilides |
| CN114656408B (en) * | 2022-04-12 | 2024-09-06 | 药源药物化学（上海）有限公司 | Synthesis process of plant protective agent intermediate |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2899435A (en) * | 1959-08-11 | S-neopentyl s-aixyl barbituric acid | ||
| US2444024A (en) * | 1948-06-29 | Sydney archer | ||
| US2937175A (en) * | 1960-05-17 | Preparation of orotic acid | ||
| US2567651A (en) * | 1951-09-11 | J-dialkyl-g-amino-l | ||
| 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 (en) * | 1955-12-21 | |||
| NL99656C (en) * | 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
- BE BE594076D patent/BE594076A/xx unknown
- CA CA731651A patent/CA731651A/en not_active Expired
- IT IT635567D patent/IT635567A/it unknown
- NL NL254838D patent/NL254838A/xx unknown
-
1960
- 1960-08-12 DE DE19601240698 patent/DE1240698C2/en not_active Expired
- 1960-08-12 SE SE7792/60A patent/SE305770B/xx unknown
- 1960-08-13 CH CH921360A patent/CH482402A/en 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/en unknown
- 1965-12-31 MY MY1965115A patent/MY6500115A/en unknown
- 1965-12-31 MY MY1965116A patent/MY6500116A/en unknown
- 1965-12-31 MY MY1965102A patent/MY6500102A/en unknown
- 1965-12-31 MY MY1965103A patent/MY6500103A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US3235360A (en) | 1966-02-15 |
| GB968661A (en) | 1964-09-02 |
| CH482402A (en) | 1969-12-15 |
| DE1240698B (en) | 1973-01-04 |
| US3254082A (en) | 1966-05-31 |
| MY6500102A (en) | 1965-12-31 |
| BR6571453D0 (en) | 1973-05-10 |
| CA731651A (en) | 1966-04-05 |
| MY6500115A (en) | 1965-12-31 |
| MY6500116A (en) | 1965-12-31 |
| BE594076A (en) | 1900-01-01 |
| IT635567A (en) | 1900-01-01 |
| SE305770B (en) | 1968-11-04 |
| NL254838A (en) | 1900-01-01 |
| DE1240698C2 (en) | 1973-01-04 |
| DK106253A (en) | 1900-01-01 |
| MY6500103A (en) | 1965-12-31 |
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