AP35A - Pyrimidine derivatives. - Google Patents

Pyrimidine derivatives. Download PDF

Info

Publication number: AP35A
Authority: AP; ARIPO
Prior art keywords: pyrimidin; formula; methylbutyrate; compound; carbon atoms
Prior art date: 1985-12-23

Application number

APAP/P/1986/000051A

Other languages

English (en)

Other versions

AP8600051A0 (en

Inventor

Alan John Whittle

Roger Salmon

Edward Mcdonald

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.)

1985-12-23

Filing date

1986-12-18

Publication date

1989-02-15

1986-11-01 Publication of AP8600051A0 publication Critical patent/AP8600051A0/xx

1986-12-18 Application filed by Ici Plc filed Critical Ici Plc

1989-02-15 Application granted granted Critical

1989-02-15 Publication of AP35A publication Critical patent/AP35A/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 114
239000000203 mixture Substances 0.000 claims description 82
-1 3-phenoxybenzyl Chemical group 0.000 claims description 79
238000000034 method Methods 0.000 claims description 74
238000002360 preparation method Methods 0.000 claims description 70
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 50
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 38
241000607479 Yersinia pestis Species 0.000 claims description 33
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 31
125000004432 carbon atom Chemical group C* 0.000 claims description 28
239000002253 acid Substances 0.000 claims description 25
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
239000001257 hydrogen Substances 0.000 claims description 16
229910052739 hydrogen Inorganic materials 0.000 claims description 16
125000003545 alkoxy group Chemical group 0.000 claims description 15
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
229910052736 halogen Chemical group 0.000 claims description 12
150000002148 esters Chemical class 0.000 claims description 11
125000005843 halogen group Chemical group 0.000 claims description 10
229910052757 nitrogen Inorganic materials 0.000 claims description 10
241000238631 Hexapoda Species 0.000 claims description 9
JGFBQFKZKSSODQ-UHFFFAOYSA-N Isothiocyanatocyclopropane Chemical compound S=C=NC1CC1 JGFBQFKZKSSODQ-UHFFFAOYSA-N 0.000 claims description 9
150000002367 halogens Chemical group 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 8
PWLNAUNEAKQYLH-UHFFFAOYSA-N butyric acid octyl ester Natural products CCCCCCCCOC(=O)CCC PWLNAUNEAKQYLH-UHFFFAOYSA-N 0.000 claims description 7
UUIQMZJEGPQKFD-UHFFFAOYSA-N n-butyric acid methyl ester Natural products CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 claims description 7
125000001309 chloro group Chemical group Cl* 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
230000000749 insecticidal effect Effects 0.000 claims description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
150000004820 halides Chemical class 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
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
230000000895 acaricidal effect Effects 0.000 claims description 3
150000001409 amidines Chemical class 0.000 claims description 3
150000001805 chlorine compounds Chemical class 0.000 claims description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
239000005864 Sulphur Chemical group 0.000 claims description 2
125000003342 alkenyl group Chemical group 0.000 claims description 2
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
125000000304 alkynyl group Chemical group 0.000 claims description 2
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
150000001735 carboxylic acids Chemical class 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 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
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 2
125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
125000000262 haloalkenyl group Chemical group 0.000 claims description 2
229950000188 halopropane Drugs 0.000 claims description 2
239000003701 inert diluent Substances 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 claims 2
IFLZOCGQECCOCJ-UHFFFAOYSA-N 1-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)CC1(C=C(Cl)Cl)C(O)=O IFLZOCGQECCOCJ-UHFFFAOYSA-N 0.000 claims 1
BFNMOMYTTGHNGJ-UHFFFAOYSA-N 2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)CC1C(O)=O BFNMOMYTTGHNGJ-UHFFFAOYSA-N 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 107
239000007788 liquid Substances 0.000 description 79
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 71
238000005481 NMR spectroscopy Methods 0.000 description 65
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 60
239000000243 solution Substances 0.000 description 53
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 52
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 40
239000002904 solvent Substances 0.000 description 36
238000001030 gas--liquid chromatography Methods 0.000 description 32
239000000047 product Substances 0.000 description 32
239000011541 reaction mixture Substances 0.000 description 32
238000005160 1H NMR spectroscopy Methods 0.000 description 30
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 27
238000006243 chemical reaction Methods 0.000 description 27
230000014759 maintenance of location Effects 0.000 description 25
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
238000001704 evaporation Methods 0.000 description 23
230000008020 evaporation Effects 0.000 description 23
239000003921 oil Substances 0.000 description 23
235000019198 oils Nutrition 0.000 description 23
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
238000009835 boiling Methods 0.000 description 21
229910052943 magnesium sulfate Inorganic materials 0.000 description 20
235000019341 magnesium sulphate Nutrition 0.000 description 20
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
150000001793 charged compounds Chemical class 0.000 description 19
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
239000004480 active ingredient Substances 0.000 description 18
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
239000000543 intermediate Substances 0.000 description 17
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 16
239000007787 solid Substances 0.000 description 16
239000012044 organic layer Substances 0.000 description 15
239000003208 petroleum Substances 0.000 description 14
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
239000012267 brine Substances 0.000 description 12
239000002917 insecticide Substances 0.000 description 12
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
239000000460 chlorine Substances 0.000 description 11
238000001816 cooling Methods 0.000 description 11
230000000694 effects Effects 0.000 description 11
FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 10
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 10
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
238000004440 column chromatography Methods 0.000 description 10
238000010992 reflux Methods 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
150000007513 acids Chemical class 0.000 description 9
GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 9
239000000725 suspension Substances 0.000 description 9
101150052863 THY1 gene Proteins 0.000 description 8
238000001914 filtration Methods 0.000 description 8
239000000741 silica gel Substances 0.000 description 8
229910002027 silica gel Inorganic materials 0.000 description 8
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 7
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 7
239000012298 atmosphere Substances 0.000 description 7
239000000284 extract 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
YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
229910021529 ammonia Inorganic materials 0.000 description 6
239000003480 eluent Substances 0.000 description 6
229940057995 liquid paraffin Drugs 0.000 description 6
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 6
239000012188 paraffin wax Substances 0.000 description 6
238000000746 purification Methods 0.000 description 6
230000035484 reaction time Effects 0.000 description 6
238000004293 19F NMR spectroscopy Methods 0.000 description 5
IOWIZOHVIJNOGZ-UHFFFAOYSA-N 2-(2-tert-butylpyrimidin-5-yl)-3-methylbutanoic acid Chemical compound CC(C)C(C(O)=O)C1=CN=C(C(C)(C)C)N=C1 IOWIZOHVIJNOGZ-UHFFFAOYSA-N 0.000 description 5
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
238000004458 analytical method Methods 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
229910052744 lithium Inorganic materials 0.000 description 5
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
239000000377 silicon dioxide Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
UCATVXQYVHFHHA-UHFFFAOYSA-N (2,3,5,6-tetrafluoro-4-prop-2-ynylphenyl)methyl 3-methyl-2-(2-propan-2-ylpyrimidin-5-yl)butanoate Chemical compound C=1N=C(C(C)C)N=CC=1C(C(C)C)C(=O)OCC1=C(F)C(F)=C(CC#C)C(F)=C1F UCATVXQYVHFHHA-UHFFFAOYSA-N 0.000 description 4
241001124076 Aphididae Species 0.000 description 4
241000196324 Embryophyta Species 0.000 description 4
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
235000019502 Orange oil Nutrition 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 4
AJLZNSWERKUGPQ-UHFFFAOYSA-N [2,3,5,6-tetrafluoro-4-(methoxymethyl)phenyl]methyl 3-methyl-2-[2-(2-methylbutan-2-yl)pyrimidin-5-yl]butanoate Chemical compound C1=NC(C(C)(C)CC)=NC=C1C(C(C)C)C(=O)OCC1=C(F)C(F)=C(COC)C(F)=C1F AJLZNSWERKUGPQ-UHFFFAOYSA-N 0.000 description 4
239000002585 base Substances 0.000 description 4
239000012141 concentrate Substances 0.000 description 4
SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 4
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
238000004821 distillation Methods 0.000 description 4
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239000000417 fungicide Substances 0.000 description 4
239000004009 herbicide Substances 0.000 description 4
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BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
238000004611 spectroscopical analysis Methods 0.000 description 4
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XZEPAJJCUPKLKW-UHFFFAOYSA-N (4-fluoro-3-phenoxyphenyl)methyl 2-(2-tert-butyl-4-fluoropyrimidin-5-yl)-3-methylbutanoate Chemical compound C=1N=C(C(C)(C)C)N=C(F)C=1C(C(C)C)C(=O)OCC(C=1)=CC=C(F)C=1OC1=CC=CC=C1 XZEPAJJCUPKLKW-UHFFFAOYSA-N 0.000 description 3
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
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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 description 3
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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 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
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230000003197 catalytic effect Effects 0.000 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 description 3
LHHLYOVYBZWIGM-UHFFFAOYSA-N diethyl 2-formylbutanedioate Chemical compound CCOC(=O)CC(C=O)C(=O)OCC LHHLYOVYBZWIGM-UHFFFAOYSA-N 0.000 description 3
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150000002500 ions Chemical class 0.000 description 3
FMKOJHQHASLBPH-UHFFFAOYSA-N isopropyl iodide Chemical compound CC(C)I FMKOJHQHASLBPH-UHFFFAOYSA-N 0.000 description 3
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
235000009566 rice Nutrition 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
239000001117 sulphuric acid Substances 0.000 description 3
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FMCAFXHLMUOIGG-IWFBPKFRSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2r)-2-formamido-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,5-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoic acid Chemical compound O=CN[C@@H](CS)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](C(=O)N[C@@H](CCSC)C(O)=O)CC1=CC(C)=C(O)C=C1C FMCAFXHLMUOIGG-IWFBPKFRSA-N 0.000 description 2
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FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 2
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QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-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 1
229940055577 oleyl alcohol Drugs 0.000 description 1
XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
LMAZKPOSWVOFGY-FBAUPLQOSA-N orine Natural products CO[C@H]1C[C@H](O[C@H]2CC[C@]3(C)[C@H]4C[C@@H](OC(=O)C=Cc5ccccc5)[C@]6(C)[C@@](O)(CC[C@]6(O)[C@]4(O)CC=C3C2)[C@H](C)OC(=O)C=Cc7ccccc7)O[C@H](C)[C@H]1O LMAZKPOSWVOFGY-FBAUPLQOSA-N 0.000 description 1
230000003151 ovacidal effect Effects 0.000 description 1
KZAUOCCYDRDERY-UHFFFAOYSA-N oxamyl Chemical compound CNC(=O)ON=C(SC)C(=O)N(C)C KZAUOCCYDRDERY-UHFFFAOYSA-N 0.000 description 1
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
RLBIQVVOMOPOHC-UHFFFAOYSA-N parathion-methyl Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C=C1 RLBIQVVOMOPOHC-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
229960000490 permethrin Drugs 0.000 description 1
RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 description 1
230000002688 persistence Effects 0.000 description 1
230000000361 pesticidal effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
239000003444 phase transfer catalyst Substances 0.000 description 1
239000003016 pheromone Substances 0.000 description 1
BULVZWIRKLYCBC-UHFFFAOYSA-N phorate Chemical compound CCOP(=S)(OCC)SCSCC BULVZWIRKLYCBC-UHFFFAOYSA-N 0.000 description 1
IOUNQDKNJZEDEP-UHFFFAOYSA-N phosalone Chemical compound C1=C(Cl)C=C2OC(=O)N(CSP(=S)(OCC)OCC)C2=C1 IOUNQDKNJZEDEP-UHFFFAOYSA-N 0.000 description 1
RGCLLPNLLBQHPF-HJWRWDBZSA-N phosphamidon Chemical compound CCN(CC)C(=O)C(\Cl)=C(/C)OP(=O)(OC)OC RGCLLPNLLBQHPF-HJWRWDBZSA-N 0.000 description 1
ATROHALUCMTWTB-OWBHPGMISA-N phoxim Chemical compound CCOP(=S)(OCC)O\N=C(\C#N)C1=CC=CC=C1 ATROHALUCMTWTB-OWBHPGMISA-N 0.000 description 1
229950001664 phoxim Drugs 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
229960005235 piperonyl butoxide Drugs 0.000 description 1
YFGYUFNIOHWBOB-UHFFFAOYSA-N pirimicarb Chemical compound CN(C)C(=O)OC1=NC(N(C)C)=NC(C)=C1C YFGYUFNIOHWBOB-UHFFFAOYSA-N 0.000 description 1
QHOQHJPRIBSPCY-UHFFFAOYSA-N pirimiphos-methyl Chemical group CCN(CC)C1=NC(C)=CC(OP(=S)(OC)OC)=N1 QHOQHJPRIBSPCY-UHFFFAOYSA-N 0.000 description 1
230000008635 plant growth Effects 0.000 description 1
235000011056 potassium acetate Nutrition 0.000 description 1
239000011698 potassium fluoride Substances 0.000 description 1
235000003270 potassium fluoride Nutrition 0.000 description 1
239000000843 powder Substances 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
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
LJZPPWWHKPGCHS-UHFFFAOYSA-N propargyl chloride Chemical compound ClCC#C LJZPPWWHKPGCHS-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 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
VJFUPGQZSXIULQ-XIGJTORUSA-N pyrethrin II Chemical compound CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 VJFUPGQZSXIULQ-XIGJTORUSA-N 0.000 description 1
150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000008929 regeneration Effects 0.000 description 1
238000011069 regeneration method Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000000344 soap Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical class [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
229920005552 sodium lignosulfonate Polymers 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
239000002689 soil Substances 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000005507 spraying Methods 0.000 description 1
125000005017 substituted alkenyl group Chemical group 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 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
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
150000003512 tertiary amines Chemical class 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
150000003606 tin compounds Chemical class 0.000 description 1
150000003608 titanium Chemical class 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
238000005809 transesterification reaction Methods 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
238000001665 trituration 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
JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 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
- 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
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
- 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
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Health & Medical Sciences (AREA)
Plant Pathology (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Pest Control & Pesticides (AREA)
Agronomy & Crop Science (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

APAP/P/1986/000051A 1985-12-23 1986-12-18 Pyrimidine derivatives. AP35A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB858531637A GB8531637D0 (en)	1985-12-23	1985-12-23	Pyrimidine derivatives

Publications (2)

Publication Number	Publication Date
AP8600051A0 AP8600051A0 (en)	1986-11-01
AP35A true AP35A (en)	1989-02-15

Family

ID=10590192

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
APAP/P/1986/000051A AP35A (en)	1985-12-23	1986-12-18	Pyrimidine derivatives.

Country Status (17)

Country	Link
US (1)	US4762835A (pt)
EP (1)	EP0227415A3 (pt)
JP (1)	JPS62158262A (pt)
KR (1)	KR870006015A (pt)
CN (1)	CN1014061B (pt)
AP (1)	AP35A (pt)
AR (1)	AR242785A1 (pt)
AU (1)	AU604663B2 (pt)
BR (1)	BR8606428A (pt)
CA (1)	CA1269662A (pt)
CS (1)	CS269991B2 (pt)
GB (2)	GB8531637D0 (pt)
HU (2)	HU206202B (pt)
IL (1)	IL81016A (pt)
OA (1)	OA08565A (pt)
PT (1)	PT84010B (pt)
ZA (1)	ZA869480B (pt)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB2157288B (en) *	1984-03-26	1988-10-26	Ici Plc	Cyclopropane derivatives
GB8714233D0 (en) *	1987-06-17	1987-07-22	Ici Plc	Pyrimidine derivatives
US4962109A (en) *	1985-12-23	1990-10-09	Imperial Chemical Industries Plc	Insecticidally and acaricidally active pyrimidine esters and intermediates therefor
GB8626520D0 (en) *	1986-11-06	1986-12-10	Ici Plc	Halogenated esters
GB8629806D0 (en) *	1986-12-12	1987-01-21	Ici Plc	Fluorobenzyl esters
US5601098A (en) *	1995-06-02	1997-02-11	Dimon Incorporated	Method and apparatus for applying methoprene to oriental tobacco
US5932736A (en) *	1997-04-07	1999-08-03	Reilly Industries, Inc.	Preparation of heterocycles using 1,3-dihalopropenes
AR029489A1 (es) *	2000-03-10	2003-07-02	Euro Celtique Sa	Piridinas, pirimidinas, pirazinas, triazinas sustituidas por arilo, composiciones farmaceuticas y el uso de las mismas para la manufactura de un medicamento
AR037233A1 (es) *	2001-09-07	2004-11-03	Euro Celtique Sa	Piridinas aril sustituidas, composiciones farmaceuticas y el uso de dichos compuestos para la elaboracion de un medicamento
AU2002953128A0 (en) *	2002-12-05	2002-12-19	Osmose (Australia) Pty Ltd	Surface treatment for wood and wood products
US8293753B2 (en)	2009-07-02	2012-10-23	Novartis Ag	Substituted 2-carboxamide cycloamino ureas
WO2012150206A2 (de)	2011-05-04	2012-11-08	Bayer Cropscience Ag	Neue cyclopropansäureeesterderivate als schädlingsbekämpfungsmittel
WO2012150207A1 (de)	2011-05-04	2012-11-08	Bayer Cropscience Ag	Verwendung von cyclopropancarbonsäureeesterderivaten zur bekämpfung von insektizid-resistenten insekten
JP7220954B2 (ja) *	2019-06-07	2023-02-13	大日本除蟲菊株式会社	エステル化合物及びその用途
CN114605335A (zh) *	2022-04-11	2022-06-10	青岛科技大学	一种嘧啶硫醚胺酯类杀虫剂
CN118339139B (zh) *	2023-12-22	2025-02-07	住友化学株式会社	酯化合物及其用途
CN118339138B (zh) *	2023-12-22	2025-02-11	住友化学株式会社	酯化合物及其用途

Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3887708A (en) *	1972-03-13	1975-06-03	Lilly Co Eli	Alpha, alpha-disubstituted-5-pyrimidinemethanes used as fungicides
GB2157288A (en) *	1984-03-26	1985-10-23	Ici Plc	Cyclopropane carboxylic acid derivatives

1985
- 1985-12-23 GB GB858531637A patent/GB8531637D0/en active Pending
1986
- 1986-12-16 US US06/942,436 patent/US4762835A/en not_active Expired - Fee Related
- 1986-12-16 EP EP86309808A patent/EP0227415A3/en not_active Ceased
- 1986-12-16 GB GB8630011A patent/GB2184441B/en not_active Expired - Fee Related
- 1986-12-17 ZA ZA869480A patent/ZA869480B/xx unknown
- 1986-12-18 AP APAP/P/1986/000051A patent/AP35A/en active
- 1986-12-18 CA CA000525745A patent/CA1269662A/en not_active Expired - Fee Related
- 1986-12-18 IL IL81016A patent/IL81016A/xx unknown
- 1986-12-19 HU HU904110A patent/HU206202B/hu not_active IP Right Cessation
- 1986-12-19 AU AU66809/86A patent/AU604663B2/en not_active Ceased
- 1986-12-19 HU HU865339A patent/HU201529B/hu unknown
- 1986-12-22 OA OA59029A patent/OA08565A/xx unknown
- 1986-12-22 CS CS869701A patent/CS269991B2/cs unknown
- 1986-12-23 JP JP61305568A patent/JPS62158262A/ja active Pending
- 1986-12-23 KR KR860011272A patent/KR870006015A/ko not_active Application Discontinuation
- 1986-12-23 BR BR8606428A patent/BR8606428A/pt unknown
- 1986-12-23 PT PT84010A patent/PT84010B/pt not_active IP Right Cessation
- 1986-12-23 CN CN86108825A patent/CN1014061B/zh not_active Expired
- 1986-12-23 AR AR86306315A patent/AR242785A1/es active

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3887708A (en) *	1972-03-13	1975-06-03	Lilly Co Eli	Alpha, alpha-disubstituted-5-pyrimidinemethanes used as fungicides
GB2157288A (en) *	1984-03-26	1985-10-23	Ici Plc	Cyclopropane carboxylic acid derivatives

Also Published As

Publication number	Publication date
CS269991B2 (en)	1990-05-14
EP0227415A3 (en)	1988-03-23
AP8600051A0 (en)	1986-11-01
KR870006015A (ko)	1987-07-08
ZA869480B (en)	1987-08-26
CA1269662A (en)	1990-05-29
JPS62158262A (ja)	1987-07-14
CS970186A2 (en)	1989-09-12
HU206202B (en)	1992-09-28
EP0227415A2 (en)	1987-07-01
GB2184441B (en)	1990-05-09
PT84010B (pt)	1989-07-31
IL81016A (en)	1992-03-29
PT84010A (en)	1987-01-01
BR8606428A (pt)	1987-10-20
HU904110D0 (en)	1990-12-28
CN1014061B (zh)	1991-09-25
IL81016A0 (en)	1987-03-31
HUT42453A (en)	1987-07-28
AR242785A1 (es)	1993-05-31
GB8531637D0 (en)	1986-02-05
CN86108825A (zh)	1987-07-22
HU201529B (en)	1990-11-28
OA08565A (en)	1988-09-30
AU6680986A (en)	1987-06-25
GB8630011D0 (en)	1987-01-28
GB2184441A (en)	1987-06-24
US4762835A (en)	1988-08-09
HUT45290A (en)	1988-06-28
AU604663B2 (en)	1991-01-03

Publication	Publication Date	Title
AP35A (en)	1989-02-15	Pyrimidine derivatives.
CA1278576C (en)	1991-01-02	2-chloro-4,5'-bis(trifluoromethyl)pyridine
US5077297A (en)	1991-12-31	Novel compounds
EP0271240B1 (en)	1994-01-19	Fluorobenzyl esters
US4962109A (en)	1990-10-09	Insecticidally and acaricidally active pyrimidine esters and intermediates therefor
US4812483A (en)	1989-03-14	Insecticidal alkenes
EP0381317B1 (en)	1994-02-23	Insecticidal compounds
US4902814A (en)	1990-02-20	Fluorobenzyl esters
AU610184B2 (en)	1991-05-16	Pyrimidine derivatives
EP0302626A2 (en)	1989-02-08	Insecticidal compounds
US5049585A (en)	1991-09-17	Certain 3,3-bis-(difluoro methyl)2,2-dimethyl-cyclopropane carboxylates having insecticidal activity
US4853414A (en)	1989-08-01	Halogenated esters
EP0276558B1 (en)	1992-07-08	Insecticidal ethers
CA1300159C (en)	1992-05-05	Insecticidal ethers
EP0298590B1 (en)	1991-12-11	Halogenated esters
US5225607A (en)	1993-07-06	Insecticidal ethers
EP0361695A2 (en)	1990-04-04	Insecticidal compounds