JPS6232760B2 - - Google Patents
Info
- Publication number
- JPS6232760B2 JPS6232760B2 JP54091112A JP9111279A JPS6232760B2 JP S6232760 B2 JPS6232760 B2 JP S6232760B2 JP 54091112 A JP54091112 A JP 54091112A JP 9111279 A JP9111279 A JP 9111279A JP S6232760 B2 JPS6232760 B2 JP S6232760B2
- Authority
- JP
- Japan
- Prior art keywords
- thionophosphate
- diethyl
- group
- methylquinazolin
- general formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 17
- 150000003246 quinazolines Chemical class 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- -1 methoxy, ethoxy, propoxy, isopropoxy, butoxy, tert-butoxy group Chemical group 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 239000002917 insecticide Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 230000000749 insecticidal effect Effects 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 235000011181 potassium carbonates Nutrition 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 241000607479 Yersinia pestis Species 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-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
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- KMJJJTCKNZYTEY-UHFFFAOYSA-N chloro-diethoxy-sulfanylidene-$l^{5}-phosphane Chemical compound CCOP(Cl)(=S)OCC KMJJJTCKNZYTEY-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 150000003222 pyridines Chemical class 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000375 suspending agent Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000336797 Eoeurysa flavocapitata Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 244000184734 Pyrus japonica Species 0.000 description 1
- 241000256248 Spodoptera Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 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 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012156 elution solvent Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-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
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
- WQYSXVGEZYESBR-UHFFFAOYSA-N thiophosphoryl chloride Chemical compound ClP(Cl)(Cl)=S WQYSXVGEZYESBR-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
本発明はキナゾリン誘導体に関する。
本発明のキナゾリン誘導体は新規化合物であ
り、下記一般式〔１〕で表わされる。
〔式中R1は水素原子、シクロアルキル基または置
換基としてハロゲン原子を有することのある低級
アルキル基、R2およびR3は低級アルキル基、R4
はハロゲン原子、ニトロ基、低級アルキル基、低
級アルコキシ基または低級アルキレンジオキシ
基、並びにｎは０または１〜４の整数を示す〕
上記一般式(1)中R1〜R4で表わされる各基を具
体的に示せば次の通りである。
低級アルキル基……炭素数１〜４の直鎖もしくは
分枝状アルキル基、例えばメチル、エチル、プ
ロピル、イソプロピル、ブチル、tert−ブチル
基等。
ハロゲン原子……弗素、塩素、臭素および沃素原
子。
シクロアルキル基……炭素数３〜８のシクロアル
キル基、例えばシクロプロピル、シクロブチ
ル、シクロペンチル、シクロヘキシル、シクロ
ヘプチルおよびシクロオクチル基等。
低級アルコキシ基……炭素数１〜４の直鎖もしく
は分枝状アルコキシ基、例えばメトキシ、エト
キシ、プロポキシ、イソプロポキシ、ブトキ
シ、tert−ブトキシ基等。
低級アルキレンジオキシ基……炭素数１〜４のア
ルキレン基を有するアルキレンジオキシ基、例
えばメチレンジオキシ、エチレンジオキシ、ト
リメチレンジオキシ基等。
置換基としてハロゲン原子を有することのある低
級アルキル基……上記炭素数１〜４の直鎖もしく
は分枝状アルキル基およびハロゲン原子が置換
された上記アルキル基、例えばトリフルオロメ
チル、トリクロルメチル、２・２・２−トリフ
ルオロエチル基等。
上記一般式(1)で表わされる本発明キナゾリン誘
導体の代表例を次に示す。
ΓＯ・Ｏ−ジエチル−Ｏ−（キナゾリン−４−イ
ル）チオノホスフエート
ΓＯ・Ｏ−ジエチル−Ｏ−（２−メチルキナゾリ
ン−４−イル）チオノホスフエート
ΓＯ・Ｏ−ジエチル−Ｏ−（２−エチルキナゾリ
ン−４−イル）チオノホスフエート
ΓＯ・Ｏ−ジエチル−Ｏ−（２−イソプロピルキ
ナゾリン−４−イル）チオノホスフエート
ΓＯ・Ｏ−ジエチル−Ｏ−（２・６−ジメチルキ
ナゾリン−４−イル）チオノホスフエート
ΓＯ・Ｏ−ジメチル−Ｏ−２−メチルキナゾリン
−４−イル）チオノホスフエート
ΓＯ・Ｏ−ジメチル−Ｏ−キナゾリン−４−イ
ル）チオノホスフエート
ΓＯ・Ｏ−ジエチル−Ｏ−（５−クロロキナゾリ
ン−４−イル）チオノホスフエート
ΓＯ・Ｏ−ジエチル−Ｏ−（６−クロロキナゾリ
ン−４−イル）チオノホスフエート
ΓＯ・Ｏ−ジエチル−Ｏ−（７−クロロキナゾリ
ン−４−イル）チオノホスフエート
ΓＯ・Ｏ−ジエチル−Ｏ−（５−クロロ−２−メ
チルキナゾリン−４−イル）チオノホスフエー
ト
ΓＯ・Ｏ−ジエチル−Ｏ−（６−クロロ−２−メ
チルキナゾリン−４−イル）チオノホスフエー
ト
ΓＯ・Ｏ−ジエチル−Ｏ−（６・７−ジクロロ−
２−メチルキナゾリン−４−イル）チオノホス
フエート
ΓＯ・Ｏ−ジエチル−Ｏ−（６−クロロ−８−ニ
トロ−２−メチルキナゾリン−４−イル）チオ
ノホスフエート
ΓＯ・Ｏ−ジエチル−Ｏ−（２−シクロヘキシル
キナゾリン−４−イル）チオノホスフエート
ΓＯ・Ｏ−ジエチル−Ｏ−（５−クロロ−８−ニ
トロ−２−メチルキナゾリン−４−イル）チオ
ノホスフエート
ΓＯ・Ｏ−ジエチル−Ｏ−（６−メトキシ−２−
メチルキナゾリン−４−イル）チオノホスフエ
ート
ΓＯ・Ｏ−ジエチル−Ｏ−（８−メトキシ−２−
メチルキナゾリン−４−イル）チオノホスフエ
ート
ΓＯ・Ｏ−ジエチル−Ｏ−（６・７−メチレンジ
オキシ−２−メチルキナゾリン−４−イル）チ
オノホスフエート
ΓＯ・Ｏ−ジエチル−Ｏ−（６−ニトロ−２−メ
チルキナゾリン−４−イル）チオノホスフエー
ト
ΓＯ・Ｏ−ジエチル−Ｏ−（２・８−ジメチルキ
ナゾリン−４−イル）チオノホスフエート
ΓＯ・Ｏ−ジエチル−Ｏ−（７−ニトロキナゾリ
ン−４−イル）チオノホスフエート
ΓＯ・Ｏ−ジエチル−Ｏ−（７−ニトロ−２−エ
チルキナゾリン−４−イル）チオノホスフエー
ト
ΓＯ・Ｏ−ジエチル−Ｏ−（８−ニトロ−２−イ
ソプロピルキナゾリン−４−イル）チオノホス
フエート
ΓＯ・Ｏ−ジエチル−Ｏ−（６−ニトロキナゾリ
ン−４−イル）チオノホスフエート
ΓＯ・Ｏ−ジエチル−Ｏ−（２−トリフルオロメ
チルキナゾリン−４−イル）チオノホスフエー
ト
ΓＯ・Ｏ−ジエチル−Ｏ−（６−メチル−２−ト
リフルオロメチルキナゾリン−４−イル）チオ
ノホスフエート
ΓＯ・Ｏ−ジエチル−Ｏ−（６・７−ジメトキシ
−２−メチルキナゾリン−４−イル）チオノホ
スフエート
ΓＯ・Ｏ−ジブチル−Ｏ−（キナゾリン−４−イ
ル）チオノホスフエート
ΓＯ・Ｏ−メチルエチル−Ｏ−（２−メチルキナ
ゾリン−４−イル）チオホスフエート
ΓＯ・Ｏ−ジエチル−Ｏ−（６−ブロモキナゾリ
ン−４−イル）チオノホスフエート
ΓＯ・Ｏ−ジメチル−Ｏ−２−シクロオクチルキ
ナゾリン−４−イル）チオノホスフエート
ΓＯ・Ｏ−ジエチル−Ｏ−（２−シクロプロピル
−６クロロキナゾリン−４−イル）チオノホス
フエート
ΓＯ・Ｏ−ジエチル−Ｏ−（２−メチル−５−フ
ルオロキナゾリン−４−イル）チオノホスフエ
ート
ΓＯ・Ｏ−ジエチル−Ｏ−（５・６・７・８−テ
トラクロルキナゾリン−４−イル）チオノホス
フエート
ΓＯ・Ｏ−ジエチル−Ｏ−（２−メチル−５・
６・８−トリブロモキナゾリン−４−イル）チ
オノホスフエート
ΓＯ・Ｏ−ジエチル−Ｏ−（５・６−エチレンジ
オキシキナゾリン−４−イル）チオノホスフエ
ート
ΓＯ・Ｏ−ジエチル−Ｏ−〔２−（２・２・２−ト
リフルオロエチル）キナゾリン−４−イル〕チ
オノホスフエート
ΓＯ・Ｏ−ジプロピル−Ｏ−（２−トリクロロメ
チルキナゾリン−４−イル）チオノホスフエー
ト
ΓＯ・Ｏ−ジエチル−Ｏ−（５−tert−ブトキシ
キナゾリン−４−イル）チオノホスフエート
ΓＯ・Ｏ−ジエチル−Ｏ−（７−tert−ブチルキ
ナゾリン−４−イル）チオノホスフエート
本発明の一般式(1)で表わされるキナゾリン誘導
体は、例えば下記一般式
又は一般式
〔両式中R1、R4及びｎは上記に同じ。Ｍはアルカ
リ金属を示す〕で表わされる公知のキナゾリン誘
導体(2)またはそのアルカリ金属塩(3)と下記一般式
〔式中R2及びR3は上記に同じ。Ｙは塩素原子また
は臭素原子を示す〕で表わされる公知のチオノリ
ン酸エステルハライド(4)とを、無溶媒又は不活性
溶媒中脱酸剤存在下又は不存在下に反応させるこ
とにより容易に製造できる。
上記において一方の出発原料とするキナゾリン
誘導体(2)またはそのアルカリ金属塩(3)は、例えば
アントラニル酸誘導体よりボーケツトおよびメイ
らの報告〔ジヤーナル オブ アメリカンケミカ
ル ソサイエテイ 第31巻 507頁（1969）〕に従
い容易に合成できる。また他方の原料であるチオ
ノリン酸エステルハライド(4)は、例えばチオ塩化
リン等とR2OH又はR3OH（R2及びR3は上記に同
じ）で表わされるアルコール類との反応によつて
得られる公知の化合物であり、該化合物中特にＹ
が塩素原子である化合物が有利に用い得る。
上記一般式(2)又は(3)で表わされる化合物と一般
式(4)で表わされる化合物との使用割合は、特に制
限はないが通常前者に対し後者を等モルないし大
過剰量好ましくは等モルないし1.5倍モル用いる
のがよい。反応は無溶媒でも行ない得るが、通常
アセトン、メチルエチルケトン等のケトン類、ク
ロロホルム、ジクロロエタン等のハロゲン化炭化
水素類、アセトニトリル、プロピオニトリル等の
ニトリル類、テトラヒドロフラン、ジグライム、
ジプロピルエーテル等のエーテル類、ベンゼン、
トルエン、キシレン等の芳香族炭化水素類等の適
当な溶媒を用いて有利に行なわれる。上記溶媒の
うちで特にアセトン、メチルエチルケトン等のケ
トン類やアセトニトリル等のニトリル類の使用は
好ましい。また上記反応において必要に応じ用い
られる脱酸剤としては、炭酸カリウム、炭酸ナト
リウム等のアルカリ金属炭酸塩類、重炭酸ソー
ダ、重炭酸カリ等のアルカリ金属重炭酸塩類、苛
性ソーダ、苛性カリ等のアルカリ金属水酸化物、
ピリジン、ピコリン、ルチジン等のピリジン類、
トリエチルアミン、ジメチルアニリン等のアミン
類等の各種塩基性化合物を例示できる。通常炭酸
カリウム、炭酸ナトリウム等のアルカリ金属炭塩
類が有利に用いられる。上記脱酸剤は一般式(3)で
表わされる化合物を用いる場合は用いる必要はな
く、またピリジン類は溶媒としても利用できる。
該脱酸剤は例えば一般式(2)で表わされる化合物に
対して等モルないし大過剰量好ましくは等モルな
いし1.5倍モルの範囲で用い得る。また上記反応
は室温ないし100℃程度好ましくは50〜70℃程度
で約１〜48時間加熱撹拌することにより行なわれ
る。
上記反応終了後は通常の分離手段例えば溶媒抽
出法、溶媒希釈法、蒸留法、再結晶法、シリカゲ
ルカラムクロマトグラフイー等を採用して目的と
する一般式(1)で表わされるキナゾリン誘導体を単
離精製できる。
かくして得られる本発明のキナゾリン誘導体
は、温血動物に対して低毒性であり、しかも優れ
た殺虫活性を有している。殊に該誘導体は農作物
害虫や衛生害虫に対して優れた殺虫効果を発揮
し、之等害虫の殺虫剤として極めて有効である。
本発明キナゾリン誘導体を有効成分として含有
する殺虫剤は、通常公知の殺虫剤と同様に、必要
に応じて適当な固体担体、液体担体、懸濁化剤、
展着剤等を用いて、一般式(1)で示される有効成分
化合物を粒剤、粉剤、分散剤、水和剤、錠剤、油
剤、噴霧剤、煙霧剤等の任意の形態に調製でき
る。用いられる担体としては、クレー、カオリ
ン、ベントナイト、タルク、酸性白土、硅藻土、
炭酸カルシウム、ニトロセルローズ、デンプン、
アラビアゴム、炭酸ガス、フレオン、水、ベンゼ
ン、ケロシン、アルコール、アセトン、キシレ
ン、メチルナフタレン、シクロヘキサノン、動植
物脂肪酸エステル等を例示できる。また懸濁化
剤、展着剤等としては、通常の界面活性剤例えば
石鹸、高級アルコールの硫酸エステル、アルキル
スルホン酸塩、第４級アンモニウム塩、ポリアル
キレンオキシド等を例示できる。
上記により調製される殺虫剤中の一般式(1)で表
わされる化合物の配合量は、その使用形態等に応
じて適宜に決定できる。例えば分散剤や水和剤等
の形態とするには、0.1〜90重量％の範囲とする
のが好ましく、また粉剤や油剤等の形態では0.1
〜10重量％程度の範囲とするのが適当であり、こ
れはそのままあるいは目的に合わせて0.00001〜
100重量％の範囲で担体もしくは水で希釈して用
いることができる。
本発明殺虫剤は、その使用に当つては公知の殺
虫剤と同様に殺虫効果を必要とする箇所に散布、
噴霧、塗布等により適用できる。その適用量は必
要とする効果に応じて適宜に決定できる。例えば
本発明薬剤を農園芸用として利用する場合通常１
ヘクタール当り有効成分量が0.1〜10Kg好ましく
は0.1〜５Kg程度となる量を目安とすればよく、
勿論これは植物やその被害の程度に応じて適宜増
減できる。またこれは例えば他の殺菌剤や殺虫剤
又は除草剤、肥料物質、土壤改良剤等と併用する
ことも可能である。
以下本発明キナゾリン誘導体につひ行なつた殺
虫試験結果を挙げる。
＜殺虫試験＞
(a) 供試化合物の２％アセトン溶液をイネの葉に
散布し風乾後ツマグロヨコバイ（３〜４令幼
虫）をおき、24時間後の致死率を求めた。結果
を下記第１表に示す。
The present invention relates to quinazoline derivatives. The quinazoline derivative of the present invention is a new compound and is represented by the following general formula [1]. [In the formula, R 1 is a hydrogen atom, a cycloalkyl group, or a lower alkyl group that may have a halogen atom as a substituent, R 2 and R 3 are lower alkyl groups, R 4
represents a halogen atom, a nitro group, a lower alkyl group, a lower alkoxy group, or a lower alkylenedioxy group, and n represents 0 or an integer of 1 to 4] Each of R 1 to R 4 in the above general formula (1) The specific groups are as follows. Lower alkyl group: a linear or branched alkyl group having 1 to 4 carbon atoms, such as methyl, ethyl, propyl, isopropyl, butyl, tert-butyl group, etc. Halogen atoms: fluorine, chlorine, bromine and iodine atoms. Cycloalkyl group: A cycloalkyl group having 3 to 8 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl groups. Lower alkoxy group: a linear or branched alkoxy group having 1 to 4 carbon atoms, such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, tert-butoxy group, etc. Lower alkylenedioxy group: an alkylenedioxy group having an alkylene group having 1 to 4 carbon atoms, such as methylenedioxy, ethylenedioxy, trimethylenedioxy group, etc. A lower alkyl group that may have a halogen atom as a substituent: the above linear or branched alkyl group having 1 to 4 carbon atoms and the above alkyl group substituted with a halogen atom, such as trifluoromethyl, trichloromethyl, 2・2,2-trifluoroethyl group, etc. Representative examples of the quinazoline derivative of the present invention represented by the above general formula (1) are shown below. ΓO・O-diethyl-O-(quinazolin-4-yl)thionophosphate ΓO・O-diethyl-O-(2-methylquinazolin-4-yl)thionophosphate ΓO・O-diethyl-O-( 2-ethylquinazolin-4-yl)thionophosphate ΓO.O-diethyl-O-(2-isopropylquinazolin-4-yl)thionophosphate ΓO.O-diethyl-O-(2,6-dimethylquinazoline) -4-yl)thionophosphate ΓO.O-dimethyl-O-2-methylquinazolin-4-yl)thionophosphate ΓO.O-dimethyl-O-quinazolin-4-yl)thionophosphate ΓO. O-diethyl-O-(5-chloroquinazolin-4-yl)thionophosphate ΓO・O-diethyl-O-(6-chloroquinazolin-4-yl)thionophosphate ΓO・O-diethyl-O- (7-chloroquinazolin-4-yl)thionophosphate ΓO.O-diethyl-O-(5-chloro-2-methylquinazolin-4-yl)thionophosphate ΓO.O-diethyl-O-(6 -Chloro-2-methylquinazolin-4-yl)thionophosphate ΓO.O-diethyl-O-(6,7-dichloro-
2-Methylquinazolin-4-yl)thionophosphate ΓO・O-diethyl-O-(6-chloro-8-nitro-2-methylquinazolin-4-yl)thionophosphate ΓO・O-diethyl-O -(2-cyclohexylquinazolin-4-yl)thionophosphate ΓO.O-diethyl-O-(5-chloro-8-nitro-2-methylquinazolin-4-yl)thionophosphate ΓO.O-diethyl -O-(6-methoxy-2-
Methylquinazolin-4-yl)thionophosphate ΓO.O-diethyl-O-(8-methoxy-2-
Methylquinazolin-4-yl)thionophosphate ΓO.O-diethyl-O-(6,7-methylenedioxy-2-methylquinazolin-4-yl)thionophosphate ΓO.O-diethyl-O-( 6-Nitro-2-methylquinazolin-4-yl)thionophosphate ΓO.O-diethyl-O-(2,8-dimethylquinazolin-4-yl)thionophosphate ΓO.O-diethyl-O-( 7-nitroquinazolin-4-yl)thionophosphate ΓO.O-diethyl-O-(7-nitro-2-ethylquinazolin-4-yl)thionophosphate ΓO.O-diethyl-O-(8- Nitro-2-isopropylquinazolin-4-yl)thionophosphate ΓO.O-diethyl-O-(6-nitroquinazolin-4-yl)thionophosphate ΓO.O-diethyl-O-(2-trifluoro Methylquinazolin-4-yl)thionophosphate ΓO.O-diethyl-O-(6-methyl-2-trifluoromethylquinazolin-4-yl)thionophosphate ΓO.O-diethyl-O-(6. 7-dimethoxy-2-methylquinazolin-4-yl)thionophosphate ΓO.O-dibutyl-O-(quinazolin-4-yl)thionophosphate ΓO.O-methylethyl-O-(2-methylquinazoline -4-yl) thiophosphate ΓO.O-diethyl-O-(6-bromoquinazolin-4-yl)thionophosphate ΓO.O-dimethyl-O-2-cyclooctylquinazolin-4-yl)thionophosphate ΓO・O-diethyl-O-(2-cyclopropyl-6chloroquinazolin-4-yl)thionophosphate ΓO・O-diethyl-O-(2-methyl-5-fluoroquinazolin-4-yl)thiono Phosphate ΓO.O-diethyl-O-(5,6.7.8-tetrachloroquinazolin-4-yl)Thionophosphate ΓO.O-diethyl-O-(2-methyl-5.
6,8-Tribromoquinazolin-4-yl)thionophosphate ΓO.O-diethyl-O-(5,6-ethylenedioxyquinazolin-4-yl)thionophosphate ΓO.O-diethyl-O- [2-(2.2.2-trifluoroethyl)quinazolin-4-yl]thionophosphate ΓO.O-dipropyl-O-(2-trichloromethylquinazolin-4-yl)thionophosphate ΓO.O -Diethyl-O-(5-tert-butoxyquinazolin-4-yl)thionophosphate ΓO.O-diethyl-O-(7-tert-butylquinazolin-4-yl)thionophosphate General formula of the present invention The quinazoline derivative represented by (1) is, for example, the following general formula: or general formula [In both formulas, R 1 , R 4 and n are the same as above. M represents an alkali metal] known quinazoline derivative (2) or its alkali metal salt (3) and the following general formula [In the formula, R 2 and R 3 are the same as above. It can be easily produced by reacting a known thionophosphate halide (4) represented by [Y represents a chlorine atom or a bromine atom] in the presence or absence of a deoxidizing agent without a solvent or in an inert solvent. . The quinazoline derivative (2) or its alkali metal salt (3) used as one of the starting materials in the above is, for example, an anthranilic acid derivative according to the report by Bokett and May et al. [Journal of American Chemical Society Vol. 31, p. 507 (1969)]. Can be easily synthesized. The other raw material, thionophosphate halide (4), can be obtained by, for example, reacting phosphorus thiochloride with an alcohol represented by R 2 OH or R 3 OH (R 2 and R 3 are the same as above). It is a known compound obtained, and among these compounds, Y
Compounds in which is a chlorine atom can be advantageously used. The ratio of the compound represented by the above general formula (2) or (3) and the compound represented by the general formula (4) is not particularly limited, but the latter is usually used in an equimolar amount to a large excess of the former, preferably in an equal molar amount. It is preferable to use molar to 1.5 times the molar amount. Although the reaction can be carried out without a solvent, it is usually carried out using ketones such as acetone and methyl ethyl ketone, halogenated hydrocarbons such as chloroform and dichloroethane, nitriles such as acetonitrile and propionitrile, tetrahydrofuran, diglyme,
Ethers such as dipropyl ether, benzene,
This is advantageously carried out using a suitable solvent such as aromatic hydrocarbons such as toluene and xylene. Among the above solvents, it is particularly preferable to use ketones such as acetone and methyl ethyl ketone, and nitriles such as acetonitrile. In addition, deoxidizing agents used as necessary in the above reaction include alkali metal carbonates such as potassium carbonate and sodium carbonate, alkali metal bicarbonates such as sodium bicarbonate and potassium bicarbonate, and alkali metal hydroxides such as caustic soda and caustic potassium. ,
Pyridines such as pyridine, picoline, and lutidine;
Examples include various basic compounds such as amines such as triethylamine and dimethylaniline. Usually, alkali metal carbonates such as potassium carbonate and sodium carbonate are advantageously used. The above deoxidizing agent does not need to be used when the compound represented by general formula (3) is used, and pyridines can also be used as a solvent.
The deoxidizing agent may be used, for example, in an amount of equimolar to a large excess, preferably equimolar to 1.5 times the molar amount, relative to the compound represented by general formula (2). Further, the above reaction is carried out by heating and stirring at room temperature to about 100°C, preferably about 50 to 70°C, for about 1 to 48 hours. After the completion of the above reaction, the desired quinazoline derivative represented by the general formula (1) can be isolated using conventional separation methods such as solvent extraction, solvent dilution, distillation, recrystallization, silica gel column chromatography, etc. Can be separated and purified. The quinazoline derivative of the present invention thus obtained has low toxicity to warm-blooded animals and has excellent insecticidal activity. In particular, the derivatives exhibit excellent insecticidal effects against agricultural pests and sanitary pests, and are extremely effective as insecticides for these pests. The insecticide containing the quinazoline derivative of the present invention as an active ingredient can be prepared using a suitable solid carrier, liquid carrier, suspending agent,
Using a spreading agent or the like, the active ingredient compound represented by general formula (1) can be prepared into any form such as granules, powders, dispersants, wettable powders, tablets, oils, sprays, and atomizers. The carriers used include clay, kaolin, bentonite, talc, acid clay, diatomaceous earth,
Calcium carbonate, nitrocellulose, starch,
Examples include gum arabic, carbon dioxide, freon, water, benzene, kerosene, alcohol, acetone, xylene, methylnaphthalene, cyclohexanone, and animal and plant fatty acid esters. Examples of suspending agents, spreading agents, etc. include common surfactants such as soaps, sulfuric acid esters of higher alcohols, alkyl sulfonates, quaternary ammonium salts, and polyalkylene oxides. The amount of the compound represented by general formula (1) in the insecticide prepared as described above can be determined as appropriate depending on the form of use and the like. For example, in the form of dispersants and wettable powders, it is preferably in the range of 0.1 to 90% by weight, and in the form of powders, oils, etc., it is preferably 0.1% by weight.
It is appropriate to set the range to about 10% by weight, and this can be changed as is or according to the purpose from 0.00001 to 10% by weight.
It can be used by diluting it with a carrier or water in a range of 100% by weight. When using the insecticide of the present invention, as with known insecticides, the insecticide is sprayed on areas where the insecticidal effect is required.
It can be applied by spraying, coating, etc. The amount to be applied can be determined as appropriate depending on the desired effect. For example, when using the drug of the present invention for agricultural and horticultural purposes, usually 1
The amount of active ingredient per hectare may be 0.1 to 10 kg, preferably 0.1 to 5 kg.
Of course, this can be increased or decreased as appropriate depending on the plant and the degree of damage to it. It can also be used in combination with, for example, other fungicides, insecticides or herbicides, fertilizer substances, soil improvers, etc. The results of insecticidal tests conducted on the quinazoline derivatives of the present invention are listed below. <Insecticidal test> (a) A 2% acetone solution of the test compound was sprayed on rice leaves, air-dried, and then black leafhoppers (3rd to 4th instar larvae) were placed on the leaves, and the mortality rate after 24 hours was determined. The results are shown in Table 1 below.
【表】
(b) ハスモシヨトウの４令幼虫の後期に供試化合
物の２％アセトン溶液１μ塗布し、１時間後
の致死率を求めた。
結果を第２表に示す。[Table] (b) 1μ of a 2% acetone solution of the test compound was applied to the late stage of the 4th instar larva of Spodoptera japonica, and the mortality rate was determined after 1 hour. The results are shown in Table 2.
【表】
以下本発明化合物の製造例を実施例として挙げ
る。
実施例 １
４（3H）−キナゾリン7.3ｇ（0.05M）及び微粉
砕した炭酸カリ6.9ｇ（0.05M）をアセトニトリ
ル300ml中で１時間レフラツクスする。室温まで
冷却した後、ジエチルクロロチオノホスフエート
9.42ｇを少量づつ加え、４時間レフラツクスを行
なう。反応終了後熱時過し、液を減圧下乾固
する。残留物をクロロホルム100mlに溶解し不溶
部を別し、再度減圧下で乾固する。残渣を石油
エーテルから再結晶して無色針状結晶のＯ・Ｏ−
ジエチル−Ｏ−（キナゾリン−４−イル）チオノ
ホスフエートを1.2ｇ得る。
融点 57〜58℃
元素分析 C12H15N2O3SP 分子量298として
計算値 Ｃ；48.32 Ｈ；5.03 Ｎ；9.40％
実測値 Ｃ；48.23 Ｈ；5.14 Ｎ；9.60％
実施例 ２
６−クロロ−２−メチル−４（3H）キナゾリ
ン４ｇ及び微粉砕した炭酸カリウム４ｇをアセト
ン200ml中で１時間レフラツクスする。その後室
温まで冷却した後ジエチルクロロチオノホスフエ
ート４ｇを加え、８時間レフラツクスする。反応
終了後熱時過し、液を減圧下濃縮乾固する。
残渣を少量のクロロホルムに溶解し、シリカゲル
（和光Ｃ−200）を充填したカラムを通し、クロロ
ホルムを溶出溶媒として用い第２溶出部を分取す
る。減圧下クロロホルムを留去し、残渣をｎ−ヘ
キサンから再結晶して無色針状結晶のＯ・Ｏ−ジ
エチル−Ｏ−（６−クロロ−２−メチルキナゾリ
ン−４−イル）チオノホスフエートを2.8ｇ得
る。
融点 82.5〜83.5℃
元素分析 C13H16N2O3PSCl
分子量346.5として
計算値 Ｃ；45.02 Ｈ；4.62 Ｎ；8.08％
実測値 Ｃ；44.72 Ｈ；4.77 Ｎ；8.05％
実施例 ３〜16
上記実施例１及び２と同様にして下式で表わさ
れる本発明キナゾリン誘導体を得る。得られた各
化合物を下式のR1及びR4で第２表に示す。また
第２表には各化合物の融点（℃）又は屈折率を併
記する。
[Table] Production examples of the compounds of the present invention are listed below as Examples. Example 1 7.3 g (0.05 M) of 4(3H)-quinazoline and 6.9 g (0.05 M) of finely ground potassium carbonate are refluxed in 300 ml of acetonitrile for 1 hour. After cooling to room temperature, diethylchlorothionophosphate
Add 9.42g little by little and reflux for 4 hours. After the reaction is completed, the mixture is heated and the liquid is dried under reduced pressure. Dissolve the residue in 100 ml of chloroform, separate the insoluble portion, and dry again under reduced pressure. The residue was recrystallized from petroleum ether to give colorless needle-like crystals of O.O-
1.2 g of diethyl-O-(quinazolin-4-yl)thionophosphate are obtained. Melting point 57-58℃ Elemental analysis C 12 H 15 N 2 O 3 SP Molecular weight 298 Calculated value C; 48.32 H; 5.03 N; 9.40% Actual value C; 48.23 H; 5.14 N; 9.60% Example 2 6-chloro- 4 g of 2-methyl-4(3H) quinazoline and 4 g of finely ground potassium carbonate are refluxed in 200 ml of acetone for 1 hour. After cooling to room temperature, 4 g of diethyl chlorothionophosphate was added and refluxed for 8 hours. After the reaction is completed, the mixture is heated and the solution is concentrated to dryness under reduced pressure.
The residue is dissolved in a small amount of chloroform, passed through a column filled with silica gel (Wako C-200), and the second eluate is fractionated using chloroform as an elution solvent. Chloroform was distilled off under reduced pressure, and the residue was recrystallized from n-hexane to obtain colorless needle-like crystals of O.O-diethyl-O-(6-chloro-2-methylquinazolin-4-yl)thionophosphate. Obtain 2.8g. Melting point 82.5-83.5℃ Elemental analysis C 13 H 16 N 2 O 3 PSCl Molecular weight 346.5 Calculated value C; 45.02 H; 4.62 N; 8.08% Actual value C; 44.72 H; 4.77 N; 8.05% Examples 3 to 16 Above implementation A quinazoline derivative of the present invention represented by the following formula is obtained in the same manner as in Examples 1 and 2. The obtained compounds are shown in Table 2 as R 1 and R 4 of the following formula. Table 2 also lists the melting point (°C) or refractive index of each compound.
【表】【table】
【表】
以下製剤例を挙げる。
製剤例 １
Ｏ・Ｏ−ジエチル−Ｏ−（キナゾリン−４−イ
ル）チオノホスフエート 20ｇタルク 980ｇ
上記化合物及びタルクを混合研摩して粉剤を得
る。
製造例 ２
Ｏ・Ｏ−ジエチル−Ｏ−（６−クロロ−２−メチ
ルキナゾリン−４−イル）チオノホスフエート
200ｇ
ホワイトカーボン 20ｇ
リグニンスルホン酸ナトリウム 20ｇ
ポリオキシエチレンアルキルエーテル 40ｇクレ− 720ｇ
上記化合物を混合研摩して水和剤を得る。[Table] Examples of formulations are listed below. Formulation Example 1 O.O-diethyl-O-(quinazolin-4-yl)thionophosphate 20g Talc 980g The above compound and talc are mixed and polished to obtain a powder. Production example 2 O.O-diethyl-O-(6-chloro-2-methylquinazolin-4-yl)thionophosphate
200g white carbon 20g sodium ligninsulfonate 20g polyoxyethylene alkyl ether 40g clay 720g The above compounds are mixed and polished to obtain a wettable powder.
Claims (1)
換基としてハロゲン原子を有することのある低級
アルキル基、R2およびR3は低級アルキル基、R4
はハロゲン原子、ニトロ基、低級アルキル基、低
級アルコキシ基または低級アルキレンジオキシ
基、並びにｎは０または１〜４の整数を示す〕 で表わされるキナゾリン誘導体。[Claims] 1. General formula [In the formula, R 1 is a hydrogen atom, a cycloalkyl group, or a lower alkyl group that may have a halogen atom as a substituent, R 2 and R 3 are lower alkyl groups, R 4
is a halogen atom, a nitro group, a lower alkyl group, a lower alkoxy group, or a lower alkylenedioxy group, and n is 0 or an integer of 1 to 4.] A quinazoline derivative represented by the following.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9111279A JPS5615296A (en) | 1979-07-17 | 1979-07-17 | Quinazoline derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9111279A JPS5615296A (en) | 1979-07-17 | 1979-07-17 | Quinazoline derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5615296A JPS5615296A (en) | 1981-02-14 |
| JPS6232760B2 true JPS6232760B2 (en) | 1987-07-16 |
Family
ID=14017426
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9111279A Granted JPS5615296A (en) | 1979-07-17 | 1979-07-17 | Quinazoline derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5615296A (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4558039A (en) * | 1982-11-22 | 1985-12-10 | The Dow Chemical Company | Phosphorus derivatives of 2-fluoroalkyl-5-pyrimidinols useful as insecticides |
| US4575499A (en) * | 1982-11-22 | 1986-03-11 | The Dow Chemical Company | Phosphorus derivatives of 4-pyrimidinols |
| JPS59127609A (en) * | 1983-01-07 | 1984-07-23 | Kubota Ltd | Method for supplying sludge of press dehydrator |
| JPS6090014A (en) * | 1983-10-24 | 1985-05-21 | Kurita Mach Mfg Co Ltd | Operation control method of filter press |
| SU1286247A1 (en) * | 1984-06-21 | 1987-01-30 | Предприятие П/Я Р-6273 | Apparatus for automatic control of filter press operation |
| KR970064298A (en) * | 1996-02-12 | 1997-09-12 | 성재갑 | Substituted quinazoline derivatives, methods for their preparation and their use as herbicides |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5049431A (en) * | 1973-08-31 | 1975-05-02 |
-
1979
- 1979-07-17 JP JP9111279A patent/JPS5615296A/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5049431A (en) * | 1973-08-31 | 1975-05-02 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5615296A (en) | 1981-02-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3894078A (en) | 5-Acetamido-2,4-dimethyltrifluoromethanesulfonanilide | |
| US4684398A (en) | Herbicidal cyanoguanidines and cyanoisothioureas | |
| JPH0640813A (en) | Herbicidal 2,6-substituted pyridine | |
| JP2921047B2 (en) | Substituted bicycloheptadione derivatives, their production method and herbicides | |
| JPS6232760B2 (en) | ||
| US4444764A (en) | Phosphorus esters of alkylcycloalkyl-5-pyrimidinols and control of corn rootworm and western spotted cucumber beetle with them | |
| GB2043643A (en) | Phosphorus containing pyrimidine compounds | |
| JPS61129172A (en) | Heterocyclic herbicide | |
| JPS59137480A (en) | Noxious organism repellent composition | |
| US3803148A (en) | Isoxazolopyrimidine herbicides and method of controlling plant growth | |
| JPS6210997B2 (en) | ||
| JPH03148265A (en) | 5,7-diphenyl-4,6-diazaindane derivative, production thereof and herbicide containing the same as active ingredient | |
| JPH0678339B2 (en) | Fused heterocycle derivative | |
| JP2810544B2 (en) | N-acyl-N-phenyltetrahydrophthalamic acid derivative, method for producing the same, and herbicide containing the same as an active ingredient | |
| US4352806A (en) | Selected 2-trichloromethyl-4-pyrimidinyl carboxylic esters and their use as fungicides | |
| US3860646A (en) | Halogenoalkanesulfonic acid amides | |
| JP3228612B2 (en) | Cyanoketone derivative | |
| JPH0625133B2 (en) | Pyrazole derivative, its production method and selective herbicide | |
| US4382087A (en) | Selected O-(2-trichloromethyl-4-pyrimidinyl)-O,O-dialkyl phosphorothionates and O-(2-trichloromethyl-4-pyrimidinyl)-O,O-dialkyl phosphoronates and their use as insecticides | |
| US4859233A (en) | 2,3,6-trichlorobenzohydroxamic acid derivatives | |
| US3275647A (en) | Phosphorus esters of hydroxy-1, 2, 3-benzothiadiazoles | |
| US4929268A (en) | Substituted oxirane compounds | |
| CA2003481A1 (en) | Herbicidal compounds | |
| JPS6041687A (en) | (2-nitro-5-aryloxy-phenylamino)-alkylphosphine oxide derivative, manufacture, herbicide and plant growth regulator | |
| US5006151A (en) | Substituted oxirane compounds |