MXPA04008769A - Compuestos de pirimidina y su uso como plaguicidas. - Google Patents
Compuestos de pirimidina y su uso como plaguicidas.Info
- Publication number
- MXPA04008769A MXPA04008769A MXPA04008769A MXPA04008769A MXPA04008769A MX PA04008769 A MXPA04008769 A MX PA04008769A MX PA04008769 A MXPA04008769 A MX PA04008769A MX PA04008769 A MXPA04008769 A MX PA04008769A MX PA04008769 A MXPA04008769 A MX PA04008769A
- Authority
- MX
- Mexico
- Prior art keywords
- tetrahydrofuran
- followed
- stirring
- saturated aqueous
- methyl
- Prior art date
Links
- 239000000575 pesticide Substances 0.000 title description 2
- 150000003230 pyrimidines Chemical class 0.000 title description 2
- -1 pyrimidine compound Chemical class 0.000 claims abstract description 509
- 239000000203 mixture Substances 0.000 claims abstract description 46
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 28
- 150000002367 halogens Chemical group 0.000 claims abstract description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 27
- 239000001257 hydrogen Substances 0.000 claims abstract description 27
- 241000607479 Yersinia pestis Species 0.000 claims abstract description 24
- 230000000361 pesticidal effect Effects 0.000 claims abstract description 17
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 14
- 239000004480 active ingredient Substances 0.000 claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims description 145
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract description 9
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract description 5
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 abstract description 4
- 150000002431 hydrogen Chemical group 0.000 abstract description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 306
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 153
- 239000000243 solution Substances 0.000 description 135
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 132
- 238000003756 stirring Methods 0.000 description 131
- 229920006395 saturated elastomer Polymers 0.000 description 129
- 239000007864 aqueous solution Substances 0.000 description 126
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 116
- 239000003921 oil Substances 0.000 description 76
- 235000019198 oils Nutrition 0.000 description 76
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 74
- 238000004519 manufacturing process Methods 0.000 description 74
- 239000012312 sodium hydride Substances 0.000 description 74
- 229910000104 sodium hydride Inorganic materials 0.000 description 74
- 239000012044 organic layer Substances 0.000 description 67
- 239000011541 reaction mixture Substances 0.000 description 67
- 239000011780 sodium chloride Substances 0.000 description 66
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 64
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 59
- 235000019270 ammonium chloride Nutrition 0.000 description 58
- 238000010898 silica gel chromatography Methods 0.000 description 58
- XJPZKYIHCLDXST-UHFFFAOYSA-N 4,6-dichloropyrimidine Chemical compound ClC1=CC(Cl)=NC=N1 XJPZKYIHCLDXST-UHFFFAOYSA-N 0.000 description 35
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 32
- 238000009472 formulation Methods 0.000 description 24
- 238000005481 NMR spectroscopy Methods 0.000 description 23
- NEEDEQSZOUAJMU-UHFFFAOYSA-N but-2-yn-1-ol Chemical compound CC#CCO NEEDEQSZOUAJMU-UHFFFAOYSA-N 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 238000005160 1H NMR spectroscopy Methods 0.000 description 19
- 238000013019 agitation Methods 0.000 description 18
- 125000001424 substituent group Chemical group 0.000 description 17
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 12
- 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 description 11
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 10
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 10
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 10
- 239000000843 powder Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 9
- 239000007921 spray Substances 0.000 description 8
- 125000005919 1,2,2-trimethylpropyl group Chemical group 0.000 description 7
- 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 239000004698 Polyethylene Substances 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 7
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 7
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- 229920000573 polyethylene Polymers 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 241000196324 Embryophyta Species 0.000 description 6
- 240000007594 Oryza sativa Species 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 6
- 239000004927 clay Substances 0.000 description 6
- CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 5
- 241001556089 Nilaparvata lugens Species 0.000 description 5
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 5
- 238000001238 wet grinding Methods 0.000 description 5
- QYLVSNORLOZDDL-UHFFFAOYSA-N 3-(6-but-2-ynoxypyrimidin-4-yl)oxy-2-methylbutan-2-ol Chemical compound CC#CCOC1=CC(OC(C)C(C)(C)O)=NC=N1 QYLVSNORLOZDDL-UHFFFAOYSA-N 0.000 description 4
- MXLMTQWGSQIYOW-UHFFFAOYSA-N 3-methyl-2-butanol Chemical compound CC(C)C(C)O MXLMTQWGSQIYOW-UHFFFAOYSA-N 0.000 description 4
- 240000007124 Brassica oleracea Species 0.000 description 4
- 240000008067 Cucumis sativus Species 0.000 description 4
- 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 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 150000005215 alkyl ethers Chemical class 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 150000001721 carbon Chemical group 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 244000038559 crop plants Species 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 239000004495 emulsifiable concentrate Substances 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 125000005918 1,2-dimethylbutyl group Chemical group 0.000 description 3
- FRGNSNIRGORREN-UHFFFAOYSA-N 1-(6-but-2-ynoxypyrimidin-4-yl)oxy-2-methylpropan-2-ol Chemical compound CC#CCOC1=CC(OCC(C)(C)O)=NC=N1 FRGNSNIRGORREN-UHFFFAOYSA-N 0.000 description 3
- CRYAMKQLOAQDHY-UHFFFAOYSA-N 1-(6-chloropyrimidin-4-yl)oxy-2-methylpropan-2-ol Chemical compound CC(C)(O)COC1=CC(Cl)=NC=N1 CRYAMKQLOAQDHY-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- SWFLKRFSIFAEIY-UHFFFAOYSA-N 2-methyl-3-(6-pent-2-ynoxypyrimidin-4-yl)oxybutan-2-ol Chemical compound CCC#CCOC1=CC(OC(C)C(C)(C)O)=NC=N1 SWFLKRFSIFAEIY-UHFFFAOYSA-N 0.000 description 3
- BYDRTKVGBRTTIT-UHFFFAOYSA-N 2-methylprop-2-en-1-ol Chemical compound CC(=C)CO BYDRTKVGBRTTIT-UHFFFAOYSA-N 0.000 description 3
- ALJQOLUWOXNOSY-UHFFFAOYSA-N 4-(3-bromo-2,2-dimethylpropoxy)-6-chloropyrimidine Chemical compound BrCC(C)(C)COC1=CC(Cl)=NC=N1 ALJQOLUWOXNOSY-UHFFFAOYSA-N 0.000 description 3
- DFVFWZYDEJOOAN-UHFFFAOYSA-N 4-chloro-6-(2,2-dichloropropoxy)pyrimidine Chemical compound CC(Cl)(Cl)COC1=CC(Cl)=NC=N1 DFVFWZYDEJOOAN-UHFFFAOYSA-N 0.000 description 3
- KQYRBAOBANZMQR-UHFFFAOYSA-N 4-chloro-6-(2,2-dimethylpentan-3-yloxy)pyrimidine Chemical compound CCC(C(C)(C)C)OC1=CC(Cl)=NC=N1 KQYRBAOBANZMQR-UHFFFAOYSA-N 0.000 description 3
- HNAGBXNLWIPKAZ-UHFFFAOYSA-N 4-chloro-6-(2,2-dimethylpropoxy)pyrimidine Chemical compound CC(C)(C)COC1=CC(Cl)=NC=N1 HNAGBXNLWIPKAZ-UHFFFAOYSA-N 0.000 description 3
- UGLXPLJOPDHSDR-UHFFFAOYSA-N 4-chloro-6-(3,3-dimethylbutan-2-yloxy)pyrimidine Chemical compound CC(C)(C)C(C)OC1=CC(Cl)=NC=N1 UGLXPLJOPDHSDR-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 241001600408 Aphis gossypii Species 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 3
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 3
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 3
- 239000005946 Cypermethrin Substances 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- 241000927584 Frankliniella occidentalis Species 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000000440 bentonite Substances 0.000 description 3
- 229910000278 bentonite Inorganic materials 0.000 description 3
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 3
- 229960005424 cypermethrin Drugs 0.000 description 3
- 235000013601 eggs Nutrition 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Chemical compound C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 description 3
- 239000000796 flavoring agent Substances 0.000 description 3
- 235000019634 flavors Nutrition 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000003071 parasitic effect Effects 0.000 description 3
- 230000003449 preventive effect Effects 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 229960001866 silicon dioxide Drugs 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 235000000346 sugar Nutrition 0.000 description 3
- 235000015112 vegetable and seed oil Nutrition 0.000 description 3
- 239000008158 vegetable oil Substances 0.000 description 3
- 125000005923 1,2-dimethylpropyloxy group Chemical group 0.000 description 2
- IVNPETZLWUIOQK-UHFFFAOYSA-N 4-(3-methylbut-3-en-2-yloxy)-6-pent-2-ynoxypyrimidine Chemical compound CCC#CCOC1=CC(OC(C)C(C)=C)=NC=N1 IVNPETZLWUIOQK-UHFFFAOYSA-N 0.000 description 2
- ZMRHMIQBJPZDSF-UHFFFAOYSA-N 4-chloro-6-(1,1-dimethoxypropan-2-yloxy)pyrimidine Chemical compound COC(OC)C(C)OC1=CC(Cl)=NC=N1 ZMRHMIQBJPZDSF-UHFFFAOYSA-N 0.000 description 2
- YCHVIVBAONFIDS-UHFFFAOYSA-N 4-chloro-6-(1-cyclopropylethoxy)pyrimidine Chemical compound C1CC1C(C)OC1=CC(Cl)=NC=N1 YCHVIVBAONFIDS-UHFFFAOYSA-N 0.000 description 2
- HVHPQIQRHHMAJB-UHFFFAOYSA-N 4-chloro-6-(3,3-dimethylbutoxy)pyrimidine Chemical compound CC(C)(C)CCOC1=CC(Cl)=NC=N1 HVHPQIQRHHMAJB-UHFFFAOYSA-N 0.000 description 2
- OKOAHZAFLIBPQZ-UHFFFAOYSA-N 4-chloro-6-(3-chloro-2,2-dimethylpropoxy)pyrimidine Chemical compound ClCC(C)(C)COC1=CC(Cl)=NC=N1 OKOAHZAFLIBPQZ-UHFFFAOYSA-N 0.000 description 2
- ZGHSYVHBNGLLPS-UHFFFAOYSA-N 4-chloro-6-(3-methylbutan-2-yloxy)pyrimidine Chemical compound CC(C)C(C)OC1=CC(Cl)=NC=N1 ZGHSYVHBNGLLPS-UHFFFAOYSA-N 0.000 description 2
- QVJTTYGAIYGSIJ-UHFFFAOYSA-N 4-chloro-6-(4-methylpentan-2-yloxy)pyrimidine Chemical compound CC(C)CC(C)OC1=CC(Cl)=NC=N1 QVJTTYGAIYGSIJ-UHFFFAOYSA-N 0.000 description 2
- ZEFJKJVIEYTKIW-UHFFFAOYSA-N 4-chloro-6-[(2,2-dichloro-1-methylcyclopropyl)methoxy]pyrimidine Chemical compound C=1C(Cl)=NC=NC=1OCC1(C)CC1(Cl)Cl ZEFJKJVIEYTKIW-UHFFFAOYSA-N 0.000 description 2
- ZJECIAISJSTMDJ-UHFFFAOYSA-N 4-chloro-6-[1-(1-methylcyclopropyl)ethoxy]pyrimidine Chemical compound C1CC1(C)C(C)OC1=CC(Cl)=NC=N1 ZJECIAISJSTMDJ-UHFFFAOYSA-N 0.000 description 2
- IGTXZTWBFAJKOS-UHFFFAOYSA-N 4-chloro-6-[3,3,3-trifluoro-2-methyl-2-(trifluoromethyl)propoxy]pyrimidine Chemical compound FC(F)(F)C(C(F)(F)F)(C)COC1=CC(Cl)=NC=N1 IGTXZTWBFAJKOS-UHFFFAOYSA-N 0.000 description 2
- RQWKDAIBLSRPIC-UHFFFAOYSA-N 4-chloro-6-propan-2-yloxypyrimidine Chemical compound CC(C)OC1=CC(Cl)=NC=N1 RQWKDAIBLSRPIC-UHFFFAOYSA-N 0.000 description 2
- 241000254032 Acrididae Species 0.000 description 2
- 241001302798 Bemisia argentifolii Species 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 241001279148 Cheyletus Species 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 241000244206 Nematoda Species 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 241001414989 Thysanoptera Species 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 230000000895 acaricidal effect Effects 0.000 description 2
- 239000000642 acaricide Substances 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 230000002547 anomalous effect Effects 0.000 description 2
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- ZLBGSRMUSVULIE-GSMJGMFJSA-N milbemycin A3 Chemical compound O1[C@H](C)[C@@H](C)CC[C@@]11O[C@H](C\C=C(C)\C[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 ZLBGSRMUSVULIE-GSMJGMFJSA-N 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- KRTSDMXIXPKRQR-AATRIKPKSA-N monocrotophos Chemical compound CNC(=O)\C=C(/C)OP(=O)(OC)OC KRTSDMXIXPKRQR-AATRIKPKSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- XYFMGGWVGACNEC-UHFFFAOYSA-N n-carbamoyl-n-phenylbenzamide Chemical class C=1C=CC=CC=1N(C(=O)N)C(=O)C1=CC=CC=C1 XYFMGGWVGACNEC-UHFFFAOYSA-N 0.000 description 1
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- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
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- 150000002825 nitriles Chemical class 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 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
- TWWDDFFHABKNMQ-UHFFFAOYSA-N oxosilicon;hydrate Chemical compound O.[Si]=O TWWDDFFHABKNMQ-UHFFFAOYSA-N 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 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 description 1
- XLMFDCKSFJWJTP-UHFFFAOYSA-N pentane-2,3-diol Chemical compound CCC(O)C(C)O XLMFDCKSFJWJTP-UHFFFAOYSA-N 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
- XAMUDJHXFNRLCY-UHFFFAOYSA-N phenthoate Chemical compound CCOC(=O)C(SP(=S)(OC)OC)C1=CC=CC=C1 XAMUDJHXFNRLCY-UHFFFAOYSA-N 0.000 description 1
- DOIRQSBPFJWKBE-UHFFFAOYSA-N phthalic acid di-n-butyl ester Natural products CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 1
- DFOXKPDFWGNLJU-UHFFFAOYSA-N pinacolyl alcohol Chemical compound CC(O)C(C)(C)C DFOXKPDFWGNLJU-UHFFFAOYSA-N 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
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- QYMMJNLHFKGANY-UHFFFAOYSA-N profenofos Chemical compound CCCSP(=O)(OCC)OC1=CC=C(Br)C=C1Cl QYMMJNLHFKGANY-UHFFFAOYSA-N 0.000 description 1
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- 239000001294 propane Substances 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
- QHMTXANCGGJZRX-WUXMJOGZSA-N pymetrozine Chemical compound C1C(C)=NNC(=O)N1\N=C\C1=CC=CN=C1 QHMTXANCGGJZRX-WUXMJOGZSA-N 0.000 description 1
- 239000002728 pyrethroid Chemical class 0.000 description 1
- DWFZBUWUXWZWKD-UHFFFAOYSA-N pyridaben Chemical compound C1=CC(C(C)(C)C)=CC=C1CSC1=C(Cl)C(=O)N(C(C)(C)C)N=C1 DWFZBUWUXWZWKD-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- HPYNBECUCCGGPA-UHFFFAOYSA-N silafluofen Chemical compound C1=CC(OCC)=CC=C1[Si](C)(C)CCCC1=CC=C(F)C(OC=2C=CC=CC=2)=C1 HPYNBECUCCGGPA-UHFFFAOYSA-N 0.000 description 1
- 229960004029 silicic acid Drugs 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 229940014213 spinosad Drugs 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 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
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- CJDWRQLODFKPEL-UHFFFAOYSA-N teflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(Cl)=C(F)C(Cl)=C1F CJDWRQLODFKPEL-UHFFFAOYSA-N 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
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 150000008334 thiadiazines Chemical class 0.000 description 1
- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical class CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- DFQMKYUSAALDDY-MQEBUAKTSA-N trinactin Chemical compound C[C@@H]([C@@H]1CC[C@@H](O1)C[C@H](OC(=O)[C@H](C)[C@H]1CC[C@H](O1)C[C@H](CC)OC(=O)[C@@H](C)[C@@H]1CC[C@@H](O1)C[C@@H](CC)OC(=O)[C@@H]1C)CC)C(=O)O[C@@H](C)C[C@@H]2CC[C@H]1O2 DFQMKYUSAALDDY-MQEBUAKTSA-N 0.000 description 1
- DFQMKYUSAALDDY-UHFFFAOYSA-N trinactin Natural products CC1C(=O)OC(CC)CC(O2)CCC2C(C)C(=O)OC(CC)CC(O2)CCC2C(C)C(=O)OC(CC)CC(O2)CCC2C(C)C(=O)OC(C)CC2CCC1O2 DFQMKYUSAALDDY-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
- C07D239/28—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
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2002066612A JP4186484B2 (ja) | 2002-03-12 | 2002-03-12 | ピリミジン化合物およびその用途 |
| PCT/JP2003/002464 WO2003076415A1 (en) | 2002-03-12 | 2003-03-04 | Pyrimidine compounds and their use as pesticides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA04008769A true MXPA04008769A (es) | 2004-12-06 |
Family
ID=27800257
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MXPA04008769A MXPA04008769A (es) | 2002-03-12 | 2003-03-04 | Compuestos de pirimidina y su uso como plaguicidas. |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US7223769B2 (enExample) |
| EP (1) | EP1483249B1 (enExample) |
| JP (1) | JP4186484B2 (enExample) |
| KR (1) | KR100936652B1 (enExample) |
| CN (1) | CN100335466C (enExample) |
| AT (1) | ATE338752T1 (enExample) |
| AU (1) | AU2003210010B2 (enExample) |
| BR (1) | BR0307581A (enExample) |
| DE (1) | DE60308154T2 (enExample) |
| EG (1) | EG24831A (enExample) |
| ES (1) | ES2271619T3 (enExample) |
| IL (2) | IL162855A0 (enExample) |
| MX (1) | MXPA04008769A (enExample) |
| TW (1) | TWI322804B (enExample) |
| WO (1) | WO2003076415A1 (enExample) |
| ZA (1) | ZA200405371B (enExample) |
Families Citing this family (66)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004085407A1 (ja) * | 2003-03-27 | 2004-10-07 | Sumitomo Chemical Company, Limited | ピリミジン化合物及びこれを含有する節足動物防除組成物 |
| JP4894225B2 (ja) * | 2004-11-12 | 2012-03-14 | 住友化学株式会社 | ４−フルオロ−６−アルキニルオキシピリミジン化合物とその製造方法 |
| TWI367208B (en) * | 2004-11-12 | 2012-07-01 | Sumitomo Chemical Co | Production method of pyrimidine compounds |
| DE102005000747A1 (de) * | 2005-01-05 | 2006-07-13 | Bayer Cropscience Ag | Substituierte Pyrimidine |
| US8541431B2 (en) | 2008-05-19 | 2013-09-24 | The University Of Tennessee Research Foundation | Pyrimidine non-classical cannabinoid compounds and related methods of use |
| US8389534B2 (en) | 2008-05-19 | 2013-03-05 | The University Of Tennessee Research Foundation | Pyrimidine non-classical cannabinoid compounds and related methods of use |
| WO2010045377A2 (en) * | 2008-10-14 | 2010-04-22 | University Of Tennessee Research Foundation, The | Pyrimidine non-classical cannabinoid compounds and related methods of use |
| WO2010119878A1 (en) * | 2009-04-16 | 2010-10-21 | Sumitomo Chemical Company, Limited | Pyrimidine compound and its use for pest control |
| WO2010119879A1 (en) * | 2009-04-16 | 2010-10-21 | Sumitomo Chemical Company, Limited | Pyrimidine compound and its use for pest control |
| TWI485138B (zh) * | 2009-07-16 | 2015-05-21 | Sds Biotech Corp | 4- (3-butynyl) aminopyrimidine derivatives as a pest control agent for agricultural and horticulture |
| JP5902100B2 (ja) * | 2011-01-14 | 2016-04-13 | 株式会社エス・ディー・エス バイオテック | ４−（３−ブチニル）アミノピリミジン誘導体を含む農園芸用有害生物防除剤組成物 |
| WO2014005982A1 (de) | 2012-07-05 | 2014-01-09 | Bayer Cropscience Ag | Insektizide und fungizide wirkstoffkombinationen |
| WO2015055554A1 (de) | 2013-10-14 | 2015-04-23 | Bayer Cropscience Ag | Wirkstoff für die saatgut- und bodenbehandlung |
| UY35772A (es) | 2013-10-14 | 2015-05-29 | Bayer Cropscience Ag | Nuevos compuestos plaguicidas |
| EP3060557A1 (de) | 2013-10-23 | 2016-08-31 | Bayer CropScience Aktiengesellschaft | Substituierte chinoxalin-derivate als schädlingsbekämpfungsmittel |
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| JPS6013769A (ja) | 1983-07-06 | 1985-01-24 | Mitsui Toatsu Chem Inc | ピリミジン誘導体、その製造法および農園芸用殺菌剤 |
| JPS6339875A (ja) * | 1986-08-05 | 1988-02-20 | Nissin Food Prod Co Ltd | ピリミジン誘導体 |
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| JPH04327578A (ja) * | 1991-04-30 | 1992-11-17 | Mitsubishi Petrochem Co Ltd | フェノキシメチルピリミジン誘導体およびそれを有効成分とする除草剤 |
| DE4131924A1 (de) * | 1991-09-25 | 1993-07-08 | Hoechst Ag | Substituierte 4-alkoxypyrimidine, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel |
| AU6111000A (en) | 1999-07-22 | 2001-02-13 | Vertex Pharmaceuticals Incorporated | Inhibitors of viral helcase |
| CN100415725C (zh) * | 2000-09-19 | 2008-09-03 | 住友化学工业株式会社 | 嘧啶类化合物及其用途 |
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- 2003-03-04 DE DE60308154T patent/DE60308154T2/de not_active Expired - Lifetime
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| EG24831A (en) | 2010-09-28 |
| EP1483249A1 (en) | 2004-12-08 |
| KR20040099322A (ko) | 2004-11-26 |
| CN100335466C (zh) | 2007-09-05 |
| WO2003076415A1 (en) | 2003-09-18 |
| BR0307581A (pt) | 2005-01-11 |
| AU2003210010A1 (en) | 2003-09-22 |
| AU2003210010B2 (en) | 2009-08-27 |
| JP4186484B2 (ja) | 2008-11-26 |
| DE60308154D1 (de) | 2006-10-19 |
| US7223769B2 (en) | 2007-05-29 |
| ES2271619T3 (es) | 2007-04-16 |
| EP1483249B1 (en) | 2006-09-06 |
| US20050171130A1 (en) | 2005-08-04 |
| ATE338752T1 (de) | 2006-09-15 |
| ZA200405371B (en) | 2005-07-06 |
| IL162855A (en) | 2010-02-17 |
| DE60308154T2 (de) | 2007-08-23 |
| TW200400181A (en) | 2004-01-01 |
| IL162855A0 (en) | 2005-11-20 |
| TWI322804B (en) | 2010-04-01 |
| CN1639131A (zh) | 2005-07-13 |
| KR100936652B1 (ko) | 2010-01-14 |
| JP2003267957A (ja) | 2003-09-25 |
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