AP57A - Pyrimidine derivatives. - Google Patents

Pyrimidine derivatives. Download PDF

Info

Publication number: AP57A
Authority: AP; ARIPO
Prior art keywords: formula; carbon atoms; acid; pyrimidin; benzyl
Prior art date: 1987-06-17

Application number

APAP/P/1988/000092A

Other languages

English (en)

Other versions

AP8800092A0 (en

Inventor

Edward Mcdonald

Roger Salmon

Alan John Whittle

Michael Gordon Hutchings

Original Assignee

Ici Plc

Priority date (The priority date 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 date listed.)

1987-06-17

Filing date

1988-06-15

Publication date

1989-10-06

1988-05-01 Publication of AP8800092A0 publication Critical patent/AP8800092A0/xx

1988-06-15 Application filed by Ici Plc filed Critical Ici Plc

1989-10-06 Application granted granted Critical

1989-10-06 Publication of AP57A publication Critical patent/AP57A/en

Links

229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title description 2
150000003230 pyrimidines Chemical class 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 216
-1 halophenoxy Chemical group 0.000 claims description 205
238000000034 method Methods 0.000 claims description 175
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 166
239000000203 mixture Substances 0.000 claims description 124
125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 113
238000002360 preparation method Methods 0.000 claims description 110
125000004432 carbon atom Chemical group C* 0.000 claims description 85
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 75
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 71
238000006243 chemical reaction Methods 0.000 claims description 60
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 51
239000002253 acid Substances 0.000 claims description 50
125000000217 alkyl group Chemical group 0.000 claims description 44
230000008569 process Effects 0.000 claims description 35
150000002367 halogens Chemical class 0.000 claims description 28
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 26
229910052739 hydrogen Inorganic materials 0.000 claims description 24
241000607479 Yersinia pestis Species 0.000 claims description 23
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 23
239000001257 hydrogen Substances 0.000 claims description 23
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 21
125000003545 alkoxy group Chemical group 0.000 claims description 20
239000000460 chlorine Substances 0.000 claims description 20
150000002148 esters Chemical class 0.000 claims description 20
229910052736 halogen Inorganic materials 0.000 claims description 20
VUAXHMVRKOTJKP-UHFFFAOYSA-N 2,2-dimethylbutyric acid Chemical compound CCC(C)(C)C(O)=O VUAXHMVRKOTJKP-UHFFFAOYSA-N 0.000 claims description 18
125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 claims description 17
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 17
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 15
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
230000000694 effects Effects 0.000 claims description 13
229910052757 nitrogen Inorganic materials 0.000 claims description 13
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
229910052799 carbon Inorganic materials 0.000 claims description 12
125000003342 alkenyl group Chemical group 0.000 claims description 11
125000004429 atom Chemical group 0.000 claims description 11
239000002585 base Substances 0.000 claims description 11
229910052801 chlorine Inorganic materials 0.000 claims description 11
239000011737 fluorine Chemical group 0.000 claims description 11
229910052731 fluorine Inorganic materials 0.000 claims description 11
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 9
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 9
125000001424 substituent group Chemical group 0.000 claims description 9
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
241000238631 Hexapoda Species 0.000 claims description 8
150000007513 acids Chemical class 0.000 claims description 8
125000000304 alkynyl group Chemical group 0.000 claims description 8
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
230000000749 insecticidal effect Effects 0.000 claims description 8
239000001301 oxygen Substances 0.000 claims description 8
229910052760 oxygen Inorganic materials 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
230000000895 acaricidal effect Effects 0.000 claims description 7
150000004820 halides Chemical class 0.000 claims description 7
125000001188 haloalkyl group Chemical group 0.000 claims description 7
125000005843 halogen group Chemical group 0.000 claims description 7
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 6
125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 claims description 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
239000005864 Sulphur Chemical group 0.000 claims description 6
125000005907 alkyl ester group Chemical group 0.000 claims description 6
125000004093 cyano group Chemical group *C#N 0.000 claims description 6
125000000753 cycloalkyl group Chemical group 0.000 claims description 6
125000004663 dialkyl amino group Chemical group 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
229910052794 bromium Inorganic materials 0.000 claims description 5
125000001309 chloro group Chemical group Cl* 0.000 claims description 5
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 5
125000000262 haloalkenyl group Chemical group 0.000 claims description 5
239000003701 inert diluent Substances 0.000 claims description 5
150000003839 salts Chemical class 0.000 claims description 5
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical group CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 4
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 4
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Chemical group C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 4
HRKQOINLCJTGBK-UHFFFAOYSA-N dihydroxidosulfur Chemical compound OSO HRKQOINLCJTGBK-UHFFFAOYSA-N 0.000 claims description 4
125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 4
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 4
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
125000006510 trifluorobenzyl group Chemical group 0.000 claims description 4
LLMLSUSAKZVFOA-UHFFFAOYSA-N 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(O)=O LLMLSUSAKZVFOA-UHFFFAOYSA-N 0.000 claims description 3
KKMIXVXSAHIDRK-UHFFFAOYSA-N 3-methyl-2-(2-methylpyrimidin-5-yl)butanoic acid Chemical compound CC(C)C(C(O)=O)C1=CN=C(C)N=C1 KKMIXVXSAHIDRK-UHFFFAOYSA-N 0.000 claims description 3
239000003377 acid catalyst Substances 0.000 claims description 3
229910052783 alkali metal Inorganic materials 0.000 claims description 3
230000029936 alkylation Effects 0.000 claims description 3
238000005804 alkylation reaction Methods 0.000 claims description 3
ZXQYGBMAQZUVMI-UNOMPAQXSA-N cyhalothrin Chemical compound CC1(C)C(\C=C(/Cl)C(F)(F)F)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-UNOMPAQXSA-N 0.000 claims description 3
125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
125000005490 tosylate group Chemical group 0.000 claims description 3
238000005809 transesterification reaction Methods 0.000 claims description 3
QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 claims description 2
IRSBUIRUPAZREL-UHFFFAOYSA-N 2-(2-tert-butylpyrimidin-5-yl)-3,3-dimethylpentanoic acid Chemical compound CCC(C)(C)C(C(O)=O)C1=CN=C(C(C)(C)C)N=C1 IRSBUIRUPAZREL-UHFFFAOYSA-N 0.000 claims description 2
VIFIYBNVYIKTCH-UHFFFAOYSA-N 2-[2-(2-chlorophenyl)pyrimidin-5-yl]-3,3-dimethylbutanoic acid Chemical compound N1=CC(C(C(O)=O)C(C)(C)C)=CN=C1C1=CC=CC=C1Cl VIFIYBNVYIKTCH-UHFFFAOYSA-N 0.000 claims description 2
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
LGRJDTZBUVBXRL-UHFFFAOYSA-N 3,3-dimethyl-2-[2-(1-methylcyclohexyl)pyrimidin-5-yl]butanoic acid Chemical compound N1=CC(C(C(O)=O)C(C)(C)C)=CN=C1C1(C)CCCCC1 LGRJDTZBUVBXRL-UHFFFAOYSA-N 0.000 claims description 2
XPAXTKKSTYIQDM-UHFFFAOYSA-N 3,3-dimethyl-2-[2-(2-methylbutan-2-yl)pyrimidin-5-yl]butanoic acid Chemical compound CCC(C)(C)C1=NC=C(C(C(O)=O)C(C)(C)C)C=N1 XPAXTKKSTYIQDM-UHFFFAOYSA-N 0.000 claims description 2
XLOPRKKSAJMMEW-SFYZADRCSA-N Chrysanthemic acid Natural products CC(C)=C[C@@H]1[C@@H](C(O)=O)C1(C)C XLOPRKKSAJMMEW-SFYZADRCSA-N 0.000 claims description 2
125000003302 alkenyloxy group Chemical group 0.000 claims description 2
125000003282 alkyl amino group Chemical group 0.000 claims description 2
125000004414 alkyl thio group Chemical group 0.000 claims description 2
125000005109 alkynylthio group Chemical group 0.000 claims description 2
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
XLOPRKKSAJMMEW-UHFFFAOYSA-N chrysanthemic acid Chemical compound CC(C)=CC1C(C(O)=O)C1(C)C XLOPRKKSAJMMEW-UHFFFAOYSA-N 0.000 claims description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
239000012024 dehydrating agents‎ Substances 0.000 claims description 2
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
150000003512 tertiary amines Chemical class 0.000 claims description 2
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 2
125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 3
125000001153 fluoro group Chemical group F* 0.000 claims 2
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 2
125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims 2
BGUAPYRHJPWVEM-UHFFFAOYSA-N 2,2-dimethyl-4-pentenoic acid Chemical compound OC(=O)C(C)(C)CC=C BGUAPYRHJPWVEM-UHFFFAOYSA-N 0.000 claims 1
HTHVOKUQFTYCBV-UHFFFAOYSA-N 2,2-dimethylbutanethioic s-acid Chemical compound CCC(C)(C)C(S)=O HTHVOKUQFTYCBV-UHFFFAOYSA-N 0.000 claims 1
OYBRQAFKDMEVAK-UHFFFAOYSA-N 2-(2-chloropyrimidin-5-yl)-3-methylbutanoic acid Chemical compound CC(C)C(C(O)=O)C1=CN=C(Cl)N=C1 OYBRQAFKDMEVAK-UHFFFAOYSA-N 0.000 claims 1
JPOYQIMIUNXWPI-UHFFFAOYSA-N 2-(2-tert-butylpyrimidin-5-yl)butanoic acid Chemical compound CCC(C(O)=O)C1=CN=C(C(C)(C)C)N=C1 JPOYQIMIUNXWPI-UHFFFAOYSA-N 0.000 claims 1
XLVUEDOQPWFPDZ-UHFFFAOYSA-N 2-(2-tert-butylpyrimidin-5-yl)pent-4-enoic acid Chemical compound CC(C)(C)C1=NC=C(C(CC=C)C(O)=O)C=N1 XLVUEDOQPWFPDZ-UHFFFAOYSA-N 0.000 claims 1
HRJGXGMRSPZLBU-UHFFFAOYSA-N 2-[2-(dimethylamino)pyrimidin-5-yl]-3,3-dimethylbutanoic acid Chemical compound CN(C)C1=NC=C(C(C(O)=O)C(C)(C)C)C=N1 HRJGXGMRSPZLBU-UHFFFAOYSA-N 0.000 claims 1
DLQRXIPFJVDJSX-UHFFFAOYSA-N 2-[2-(dimethylamino)pyrimidin-5-yl]-3-methylbutanoic acid Chemical compound CC(C)C(C(O)=O)C1=CN=C(N(C)C)N=C1 DLQRXIPFJVDJSX-UHFFFAOYSA-N 0.000 claims 1
KSNKQSPJFRQSEI-UHFFFAOYSA-N 3,3,3-trifluoropropanoic acid Chemical compound OC(=O)CC(F)(F)F KSNKQSPJFRQSEI-UHFFFAOYSA-N 0.000 claims 1
VDYBPBLQDTVBRT-UHFFFAOYSA-N [C+2] Chemical compound [C+2] VDYBPBLQDTVBRT-UHFFFAOYSA-N 0.000 claims 1
238000005903 acid hydrolysis reaction Methods 0.000 claims 1
125000005108 alkenylthio group Chemical group 0.000 claims 1
125000005133 alkynyloxy group Chemical group 0.000 claims 1
OKTJSMMVPCPJKN-YPZZEJLDSA-N carbon-10 atom Chemical group [10C] OKTJSMMVPCPJKN-YPZZEJLDSA-N 0.000 claims 1
238000005949 ozonolysis reaction Methods 0.000 claims 1
150000003242 quaternary ammonium salts Chemical class 0.000 claims 1
150000005376 secondary alkyl halides Chemical class 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 141
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 138
238000001030 gas--liquid chromatography Methods 0.000 description 135
230000014759 maintenance of location Effects 0.000 description 129
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 126
239000000243 solution Substances 0.000 description 111
238000005160 1H NMR spectroscopy Methods 0.000 description 88
238000005481 NMR spectroscopy Methods 0.000 description 86
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 82
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 76
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 73
239000002904 solvent Substances 0.000 description 70
239000007788 liquid Substances 0.000 description 56
239000011541 reaction mixture Substances 0.000 description 56
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VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 44
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 44
239000003921 oil Substances 0.000 description 43
235000019198 oils Nutrition 0.000 description 43
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 40
238000001704 evaporation Methods 0.000 description 38
230000008020 evaporation Effects 0.000 description 38
229910052943 magnesium sulfate Inorganic materials 0.000 description 38
235000019341 magnesium sulphate Nutrition 0.000 description 38
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 37
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 35
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
150000001793 charged compounds Chemical class 0.000 description 32
239000010408 film Substances 0.000 description 31
238000010992 reflux Methods 0.000 description 28
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 26
239000007787 solid Substances 0.000 description 26
239000000741 silica gel Substances 0.000 description 25
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239000004480 active ingredient Substances 0.000 description 23
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 21
238000002844 melting Methods 0.000 description 18
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238000009835 boiling Methods 0.000 description 17
239000000284 extract Substances 0.000 description 16
238000003756 stirring Methods 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 14
239000012044 organic layer Substances 0.000 description 14
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 14
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 13
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239000012141 concentrate Substances 0.000 description 13
238000001816 cooling Methods 0.000 description 13
239000000543 intermediate Substances 0.000 description 13
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 12
239000003054 catalyst Substances 0.000 description 11
238000004440 column chromatography Methods 0.000 description 11
238000010438 heat treatment Methods 0.000 description 11
239000002917 insecticide Substances 0.000 description 11
MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 10
239000012299 nitrogen atmosphere Substances 0.000 description 10
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
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QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 9
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238000010790 dilution Methods 0.000 description 9
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238000005361 D2 NMR spectroscopy Methods 0.000 description 8
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235000019502 Orange oil Nutrition 0.000 description 8
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239000012267 brine Substances 0.000 description 8
230000003197 catalytic effect Effects 0.000 description 8
239000000706 filtrate Substances 0.000 description 8
239000010502 orange oil Substances 0.000 description 8
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229920001983 poloxamer Polymers 0.000 description 8
229910052708 sodium Inorganic materials 0.000 description 8
239000011734 sodium Substances 0.000 description 8
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
HUHXLHLWASNVDB-UHFFFAOYSA-N 2-(oxan-2-yloxy)oxane Chemical compound O1CCCCC1OC1OCCCC1 HUHXLHLWASNVDB-UHFFFAOYSA-N 0.000 description 7
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238000004458 analytical method Methods 0.000 description 7
239000012298 atmosphere Substances 0.000 description 7
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
229910000041 hydrogen chloride Inorganic materials 0.000 description 7
238000000746 purification Methods 0.000 description 7
239000000377 silicon dioxide Substances 0.000 description 7
238000005507 spraying Methods 0.000 description 7
239000000725 suspension Substances 0.000 description 7
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239000000428 dust Substances 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
ZFGZWYURJBMCLR-UHFFFAOYSA-N ethyl 2-(2,2-diethoxyethyl)-3,3-dimethylbutanoate Chemical compound CCOC(OCC)CC(C(C)(C)C)C(=O)OCC ZFGZWYURJBMCLR-UHFFFAOYSA-N 0.000 description 2
IEMGWBMVQLVHEY-UHFFFAOYSA-N ethyl 2-(3-amino-6,7-dihydro-5h-cyclopenta[b]pyridin-7-yl)acetate Chemical compound NC1=CN=C2C(CC(=O)OCC)CCC2=C1 IEMGWBMVQLVHEY-UHFFFAOYSA-N 0.000 description 2
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BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
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239000012535 impurity Substances 0.000 description 2
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239000011630 iodine Substances 0.000 description 2
239000005910 lambda-Cyhalothrin Substances 0.000 description 2
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SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
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SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 2
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KJRCEJOSASVSRA-UHFFFAOYSA-N propane-2-thiol Chemical compound CC(C)S KJRCEJOSASVSRA-UHFFFAOYSA-N 0.000 description 2
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235000003270 potassium fluoride Nutrition 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
SMKRKQBMYOFFMU-UHFFFAOYSA-N prallethrin Chemical compound CC1(C)C(C=C(C)C)C1C(=O)OC1C(C)=C(CC#C)C(=O)C1 SMKRKQBMYOFFMU-UHFFFAOYSA-N 0.000 description 1
238000012746 preparative thin layer chromatography Methods 0.000 description 1
BHLUERUPCAAQGF-UHFFFAOYSA-N prop-2-yne-1-thiol Chemical compound SCC#C BHLUERUPCAAQGF-UHFFFAOYSA-N 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
YSAXXSKRBQEJOY-UHFFFAOYSA-N propan-2-yl 2,3,5,6-tetrafluoro-4-(methoxymethyl)benzoate Chemical compound COCC1=C(F)C(F)=C(C(=O)OC(C)C)C(F)=C1F YSAXXSKRBQEJOY-UHFFFAOYSA-N 0.000 description 1
239000001294 propane Substances 0.000 description 1
LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 description 1
ZYHMJXZULPZUED-UHFFFAOYSA-N propargite Chemical compound C1=CC(C(C)(C)C)=CC=C1OC1C(OS(=O)OCC#C)CCCC1 ZYHMJXZULPZUED-UHFFFAOYSA-N 0.000 description 1
239000008262 pumice Substances 0.000 description 1
HYJYGLGUBUDSLJ-UHFFFAOYSA-N pyrethrin Natural products CCC(=O)OC1CC(=C)C2CC3OC3(C)C2C2OC(=O)C(=C)C12 HYJYGLGUBUDSLJ-UHFFFAOYSA-N 0.000 description 1
229940070846 pyrethrins Drugs 0.000 description 1
239000002728 pyrethroid Substances 0.000 description 1
150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000004064 recycling Methods 0.000 description 1
230000008929 regeneration Effects 0.000 description 1
238000011069 regeneration method Methods 0.000 description 1
238000012216 screening Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000000526 short-path distillation Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000000344 soap Substances 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
229910001379 sodium hypophosphite Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
HFQQZARZPUDIFP-UHFFFAOYSA-M sodium;2-dodecylbenzenesulfonate Chemical compound [Na+].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O HFQQZARZPUDIFP-UHFFFAOYSA-M 0.000 description 1
239000011343 solid material Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
235000015096 spirit Nutrition 0.000 description 1
125000005017 substituted alkenyl group Chemical group 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
JXHJNEJVUNHLKO-UHFFFAOYSA-N sulprofos Chemical compound CCCSP(=S)(OCC)OC1=CC=C(SC)C=C1 JXHJNEJVUNHLKO-UHFFFAOYSA-N 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
WMXCDAVJEZZYLT-UHFFFAOYSA-N tert-butylthiol Chemical compound CC(C)(C)S WMXCDAVJEZZYLT-UHFFFAOYSA-N 0.000 description 1
238000010998 test method Methods 0.000 description 1
MLGCXEBRWGEOQX-UHFFFAOYSA-N tetradifon Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl MLGCXEBRWGEOQX-UHFFFAOYSA-N 0.000 description 1
229960005199 tetramethrin Drugs 0.000 description 1
OPASCBHCTNRLRM-UHFFFAOYSA-N thiometon Chemical compound CCSCCSP(=S)(OC)OC OPASCBHCTNRLRM-UHFFFAOYSA-N 0.000 description 1
101150068774 thyX gene Proteins 0.000 description 1
150000003606 tin compounds Chemical class 0.000 description 1
150000003608 titanium Chemical class 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
HHBXWXJLQYJJBW-UHFFFAOYSA-M triphenyl(propan-2-yl)phosphanium;iodide Chemical compound [I-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C(C)C)C1=CC=CC=C1 HHBXWXJLQYJJBW-UHFFFAOYSA-M 0.000 description 1
238000002604 ultrasonography Methods 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
231100000925 very toxic Toxicity 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
- 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
- C07D239/30—Halogen atoms or nitro radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
- 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
- C07D401/12—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 linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Agronomy & Crop Science (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pyridine Compounds (AREA)

APAP/P/1988/000092A 1987-06-17 1988-06-15 Pyrimidine derivatives. AP57A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB878714233A GB8714233D0 (en)	1987-06-17	1987-06-17	Pyrimidine derivatives

Publications (2)

Publication Number	Publication Date
AP8800092A0 AP8800092A0 (en)	1988-05-01
AP57A true AP57A (en)	1989-10-06

Family

ID=10619103

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
APAP/P/1988/000092A AP57A (en)	1987-06-17	1988-06-15	Pyrimidine derivatives.

Country Status (17)

Country	Link
EP (1)	EP0295839A3 (cs)
JP (1)	JPS6416769A (cs)
KR (1)	KR890000437A (cs)
CN (1)	CN1019574B (cs)
AP (1)	AP57A (cs)
AU (1)	AU610184B2 (cs)
BR (1)	BR8802952A (cs)
CS (1)	CS421088A2 (cs)
DK (1)	DK334888A (cs)
GB (3)	GB8714233D0 (cs)
HU (2)	HU203644B (cs)
IL (1)	IL86560A0 (cs)
NZ (1)	NZ224836A (cs)
OA (1)	OA08742A (cs)
PT (1)	PT87743B (cs)
RU (1)	RU1801108C (cs)
ZA (1)	ZA883862B (cs)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8902688D0 (en) *	1989-02-07	1989-03-30	Ici Plc	Pyrimidine derivatives
GB9005223D0 (en) *	1990-03-08	1990-05-02	Mead Corp	Wrap-around carton with end closure panels
CN105295951B (zh) *	2014-12-12	2018-04-24	石家庄诚志永华显示材料有限公司	含有环丙基的液晶化合物以及液晶混合物

Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0162538A2 (en) *	1984-03-26	1985-11-27	Imperial Chemical Industries Plc	Cyclopropane derivates
EP0227415A2 (en) *	1985-12-23	1987-07-01	Imperial Chemical Industries Plc	Pyrimidine derivatives

1987
- 1987-06-17 GB GB878714233A patent/GB8714233D0/en active Pending
1988
- 1988-05-25 GB GB888812344A patent/GB8812344D0/en active Pending
- 1988-05-30 ZA ZA883862A patent/ZA883862B/xx unknown
- 1988-05-30 IL IL86560A patent/IL86560A0/xx unknown
- 1988-05-30 NZ NZ224836A patent/NZ224836A/en unknown
- 1988-06-03 AU AU17389/88A patent/AU610184B2/en not_active Ceased
- 1988-06-10 GB GB8813780A patent/GB2209525B/en not_active Expired - Lifetime
- 1988-06-10 EP EP19880305337 patent/EP0295839A3/en not_active Withdrawn
- 1988-06-15 HU HU883052A patent/HU203644B/hu unknown
- 1988-06-15 AP APAP/P/1988/000092A patent/AP57A/en active
- 1988-06-15 OA OA59374A patent/OA08742A/xx unknown
- 1988-06-15 HU HU908470A patent/HU908470D0/hu unknown
- 1988-06-16 BR BR8802952A patent/BR8802952A/pt not_active Application Discontinuation
- 1988-06-16 CS CS884210A patent/CS421088A2/cs unknown
- 1988-06-16 PT PT87743A patent/PT87743B/pt not_active IP Right Cessation
- 1988-06-17 CN CN88103836A patent/CN1019574B/zh not_active Expired
- 1988-06-17 DK DK334888A patent/DK334888A/da not_active Application Discontinuation
- 1988-06-17 JP JP63148425A patent/JPS6416769A/ja active Pending
- 1988-06-17 KR KR1019880007305A patent/KR890000437A/ko not_active Withdrawn
- 1988-12-12 RU SU884613066A patent/RU1801108C/ru active

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0162538A2 (en) *	1984-03-26	1985-11-27	Imperial Chemical Industries Plc	Cyclopropane derivates
EP0227415A2 (en) *	1985-12-23	1987-07-01	Imperial Chemical Industries Plc	Pyrimidine derivatives

Also Published As

Publication number	Publication date
AP8800092A0 (en)	1988-05-01
AU1738988A (en)	1988-12-22
PT87743B (pt)	1992-10-30
GB8812344D0 (en)	1988-06-29
JPS6416769A (en)	1989-01-20
CN1019574B (zh)	1992-12-23
GB2209525B (en)	1991-04-03
KR890000437A (ko)	1989-03-14
NZ224836A (en)	1991-03-26
OA08742A (fr)	1989-03-31
ZA883862B (en)	1988-12-19
DK334888D0 (da)	1988-06-17
EP0295839A3 (en)	1991-07-31
GB2209525A (en)	1989-05-17
AU610184B2 (en)	1991-05-16
EP0295839A2 (en)	1988-12-21
IL86560A0 (en)	1988-11-15
CN1030412A (zh)	1989-01-18
HUT47384A (en)	1989-03-28
HU908470D0 (en)	1991-07-29
GB8813780D0 (en)	1988-07-13
GB8714233D0 (en)	1987-07-22
BR8802952A (pt)	1989-01-10
CS421088A2 (en)	1991-02-12
DK334888A (da)	1988-12-18
HU203644B (en)	1991-09-30
RU1801108C (ru)	1993-03-07
PT87743A (pt)	1988-07-01

Publication	Publication Date	Title
AP35A (en)	1989-02-15	Pyrimidine derivatives.
EP0660827B1 (en)	1997-04-16	Heterocyclic compounds with parasitical activity
CA1278576C (en)	1991-01-02	2-chloro-4,5'-bis(trifluoromethyl)pyridine
US5010200A (en)	1991-04-23	Pyrimidine derivatives
EP0338686A2 (en)	1989-10-25	Pyrimidinone derivatives
EP0302612B1 (en)	1992-03-04	Insecticidal compounds characterised by enhanced knockdown effect
AP57A (en)	1989-10-06	Pyrimidine derivatives.
EP0271240B1 (en)	1994-01-19	Fluorobenzyl esters
EP0302626A2 (en)	1989-02-08	Insecticidal compounds
EP0381317B1 (en)	1994-02-23	Insecticidal compounds
EP0221635A1 (en)	1987-05-13	Fluoro alcohols and insecticidal esters thereof
AP97A (en)	1990-09-12	Fluorobenzyl esters.
EP0220810B1 (en)	1990-05-02	Insecticidal ethers
GB2157288A (en)	1985-10-23	Cyclopropane carboxylic acid derivatives
EP0276558B1 (en)	1992-07-08	Insecticidal ethers
EP0266947B1 (en)	1991-12-04	Halogenated esters
EP0364116A1 (en)	1990-04-18	Insecticidal compounds
EP0280383A1 (en)	1988-08-31	Process for intermediates for insecticidal compounds
EP0266891A1 (en)	1988-05-11	Insecticidal ethers
EP0298590B1 (en)	1991-12-11	Halogenated esters