JPH0454168A - N-sulfonylamide derivative and herbicide therefrom - Google Patents
N-sulfonylamide derivative and herbicide therefromInfo
- Publication number
- JPH0454168A JPH0454168A JP16627190A JP16627190A JPH0454168A JP H0454168 A JPH0454168 A JP H0454168A JP 16627190 A JP16627190 A JP 16627190A JP 16627190 A JP16627190 A JP 16627190A JP H0454168 A JPH0454168 A JP H0454168A
- Authority
- JP
- Japan
- Prior art keywords
- group
- compound
- formula
- solvent
- solvents
- 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.)
- Pending
Links
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 16
- 239000004009 herbicide Substances 0.000 title claims abstract description 13
- QECVIPBZOPUTRD-UHFFFAOYSA-N N=S(=O)=O Chemical class N=S(=O)=O QECVIPBZOPUTRD-UHFFFAOYSA-N 0.000 title claims description 7
- 150000003839 salts Chemical class 0.000 claims abstract description 20
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 4
- 239000004480 active ingredient Substances 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 3
- 239000002904 solvent Substances 0.000 abstract description 80
- 150000001875 compounds Chemical class 0.000 abstract description 70
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract description 39
- -1 cyano, imidazolyl Chemical group 0.000 abstract description 23
- 241000196324 Embryophyta Species 0.000 abstract description 11
- 240000007594 Oryza sativa Species 0.000 abstract description 4
- 235000007164 Oryza sativa Nutrition 0.000 abstract description 4
- 235000009566 rice Nutrition 0.000 abstract description 4
- 244000068988 Glycine max Species 0.000 abstract description 3
- 235000010469 Glycine max Nutrition 0.000 abstract description 3
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 abstract description 3
- 239000003795 chemical substances by application Substances 0.000 abstract description 3
- 240000005979 Hordeum vulgare Species 0.000 abstract description 2
- 235000007340 Hordeum vulgare Nutrition 0.000 abstract description 2
- 235000021307 Triticum Nutrition 0.000 abstract description 2
- 244000098338 Triticum aestivum Species 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 244000055702 Amaranthus viridis Species 0.000 abstract 1
- 235000004135 Amaranthus viridis Nutrition 0.000 abstract 1
- 241000817048 Cyperus microiria Species 0.000 abstract 1
- 240000003176 Digitaria ciliaris Species 0.000 abstract 1
- 235000017898 Digitaria ciliaris Nutrition 0.000 abstract 1
- 241000192040 Echinochloa phyllopogon Species 0.000 abstract 1
- 244000085269 Scirpus juncoides Species 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 63
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 49
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
- 229910001868 water Inorganic materials 0.000 description 41
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 238000006243 chemical reaction Methods 0.000 description 33
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 26
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- 239000002585 base Substances 0.000 description 24
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 20
- 239000000203 mixture Substances 0.000 description 20
- 229910052783 alkali metal Inorganic materials 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 18
- 239000007788 liquid Substances 0.000 description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 17
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 14
- 238000001914 filtration Methods 0.000 description 14
- 229910000104 sodium hydride Inorganic materials 0.000 description 13
- 239000012312 sodium hydride Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- 239000013078 crystal Substances 0.000 description 12
- 239000002689 soil Substances 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 11
- 238000009835 boiling Methods 0.000 description 11
- 238000009472 formulation Methods 0.000 description 11
- 239000008096 xylene Substances 0.000 description 11
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 10
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- 239000004215 Carbon black (E152) Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 150000001340 alkali metals Chemical class 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 229930195733 hydrocarbon Natural products 0.000 description 9
- 150000002430 hydrocarbons Chemical class 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 description 9
- 235000011181 potassium carbonates Nutrition 0.000 description 9
- 238000010898 silica gel chromatography Methods 0.000 description 9
- 229910000029 sodium carbonate Inorganic materials 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 8
- 150000008041 alkali metal carbonates Chemical class 0.000 description 8
- 150000008282 halocarbons Chemical class 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 230000002378 acidificating effect Effects 0.000 description 7
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 7
- 150000008046 alkali metal hydrides Chemical class 0.000 description 7
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 7
- 150000001342 alkaline earth metals Chemical class 0.000 description 7
- 239000004210 ether based solvent Substances 0.000 description 7
- 239000005453 ketone based solvent Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000002798 polar solvent Substances 0.000 description 7
- 239000004563 wettable powder Substances 0.000 description 7
- FXZHRICSIMZBSC-UHFFFAOYSA-N 2-methyl-n-methylsulfonylbutanamide Chemical compound CCC(C)C(=O)NS(C)(=O)=O FXZHRICSIMZBSC-UHFFFAOYSA-N 0.000 description 6
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 6
- 239000005456 alcohol based solvent Substances 0.000 description 6
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 6
- 229910052700 potassium Inorganic materials 0.000 description 6
- 229960003975 potassium Drugs 0.000 description 6
- 239000011591 potassium Substances 0.000 description 6
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 6
- 229910000105 potassium hydride Inorganic materials 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 5
- 240000001341 Reynoutria japonica Species 0.000 description 5
- 235000018167 Reynoutria japonica Nutrition 0.000 description 5
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 5
- 239000003759 ester based solvent Substances 0.000 description 5
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- JHUUPUMBZGWODW-UHFFFAOYSA-N 3,6-dihydro-1,2-dioxine Chemical compound C1OOCC=C1 JHUUPUMBZGWODW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 241000254032 Acrididae Species 0.000 description 3
- 244000058871 Echinochloa crus-galli Species 0.000 description 3
- 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
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- CHWRSCGUEQEHOH-UHFFFAOYSA-N potassium oxide Chemical compound [O-2].[K+].[K+] CHWRSCGUEQEHOH-UHFFFAOYSA-N 0.000 description 3
- 229910001950 potassium oxide Inorganic materials 0.000 description 3
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 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
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-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
- 229920000742 Cotton Polymers 0.000 description 2
- 244000301850 Cupressus sempervirens Species 0.000 description 2
- 241000254158 Lampyridae Species 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000012456 homogeneous solution Substances 0.000 description 2
- 229910017053 inorganic salt Inorganic materials 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical class CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 229960005235 piperonyl butoxide Drugs 0.000 description 2
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 2
- 235000015497 potassium bicarbonate Nutrition 0.000 description 2
- 239000011736 potassium bicarbonate Substances 0.000 description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 2
- CUQOHAYJWVTKDE-UHFFFAOYSA-N potassium;butan-1-olate Chemical compound [K+].CCCC[O-] CUQOHAYJWVTKDE-UHFFFAOYSA-N 0.000 description 2
- 239000003586 protic polar solvent Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 description 1
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 1
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
- JALHQZFIMJNYPT-UHFFFAOYSA-N 2-(3-methylbutyl)-1h-imidazole Chemical compound CC(C)CCC1=NC=CN1 JALHQZFIMJNYPT-UHFFFAOYSA-N 0.000 description 1
- TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 description 1
- 240000006995 Abutilon theophrasti Species 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 235000004405 Ageratum conyzoides Nutrition 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 240000001592 Amaranthus caudatus Species 0.000 description 1
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 1
- 235000007320 Avena fatua Nutrition 0.000 description 1
- 241001647031 Avena sterilis Species 0.000 description 1
- 235000004535 Avena sterilis Nutrition 0.000 description 1
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
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- 241000234646 Cyperaceae Species 0.000 description 1
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- 240000003173 Drymaria cordata Species 0.000 description 1
- 235000008247 Echinochloa frumentacea Nutrition 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
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- 241000237858 Gastropoda Species 0.000 description 1
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- 229920000084 Gum arabic Polymers 0.000 description 1
- 240000001549 Ipomoea eriocarpa Species 0.000 description 1
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- 239000005909 Kieselgur Substances 0.000 description 1
- 241001520921 Leersia virginica Species 0.000 description 1
- 240000000486 Lepidium draba Species 0.000 description 1
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- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 244000197975 Solidago virgaurea Species 0.000 description 1
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- 240000002439 Sorghum halepense Species 0.000 description 1
- 240000000851 Vaccinium corymbosum Species 0.000 description 1
- 235000003095 Vaccinium corymbosum Nutrition 0.000 description 1
- 235000017537 Vaccinium myrtillus Nutrition 0.000 description 1
- 241001148683 Zostera marina Species 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 235000021014 blueberries Nutrition 0.000 description 1
- BRTFVKHPEHKBQF-UHFFFAOYSA-N bromocyclopentane Chemical compound BrC1CCCC1 BRTFVKHPEHKBQF-UHFFFAOYSA-N 0.000 description 1
- 239000004067 bulking agent Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 235000011116 calcium hydroxide Nutrition 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-M carbonochloridate Chemical compound [O-]C(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-M 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007806 chemical reaction intermediate Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125851 compound 27 Drugs 0.000 description 1
- 229940125807 compound 37 Drugs 0.000 description 1
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- BYQFBFWERHXONI-UHFFFAOYSA-N diethyl 2-propan-2-ylpropanedioate Chemical compound CCOC(=O)C(C(C)C)C(=O)OCC BYQFBFWERHXONI-UHFFFAOYSA-N 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 230000000887 hydrating effect Effects 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000002955 isolation Methods 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
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- HVQWYKPSNHGIDD-UHFFFAOYSA-N methyl 2-isocyanatosulfonylbenzoate Chemical compound COC(=O)C1=CC=CC=C1S(=O)(=O)N=C=O HVQWYKPSNHGIDD-UHFFFAOYSA-N 0.000 description 1
- VOEYXMAFNDNNED-UHFFFAOYSA-N metolcarb Chemical compound CNC(=O)OC1=CC=CC(C)=C1 VOEYXMAFNDNNED-UHFFFAOYSA-N 0.000 description 1
- OUPLTJDZPQZRBW-UHFFFAOYSA-N n-(oxomethylidene)methanesulfonamide Chemical compound CS(=O)(=O)N=C=O OUPLTJDZPQZRBW-UHFFFAOYSA-N 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 231100000820 toxicity test Toxicity 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Abstract
Description
［産業上の利用分野］
本発明は、新規なＮ−スルホニルアミド誘導体及びその
塩と、それらを有効成分とする除草剤に関するものであ
る。
［従来の技術］
近年、数多くの除草剤が開発され、農作業の省力化、生
産性の向上に寄与しているが、これらの除草剤は、農作
物、雑草のそれぞれに対して特異的な作用を示すものが
多いため、適用地域、農作物の種類に応じて、効果的な
ものを適宜選んで用いることが必要になる。そのため除
草効果を示す新規な化合物を開発することが、この分野
においては常に重要な課題となっている。
［発明が解決しようとする課題］
本発明は、従来用いられている除草剤とは異なった化学
構造をもつ化合物を有効成分とし、種々の農作物の栽培
に多角的に使用しうる新規な＃草刑を提供することを目
的とする。
［課題を解決するための手段］
上記目的を達成するため鋭意研究を重ねた結果。
ピリミジン環をもつある種のＮ−スルホニルアミド誘導
体及びその塩が種々の雑草の防除に対して有効であり、
しかも農作物に対して無害であることを見出し１本発明
をなすに至った。
すなわち１本発明は一般式
（式中、Ｒはアルキル基、ハロアルキル基または任意に
置換されてもよいフェニル基を示し、Ｒは水素原子、ア
ルキル基、アルケニル基、ハロアルケニル基、シクロア
ルキル基、シクロアルケニル基、シクロアルキルアルキ
ル基または任意に置換されてもよいフェニル基を示し、
Ｘ及びＹは同一または相異なり、アルキル基、アルコキ
シ基、ハロアルコキシ基またはハロゲン原子を示す、）
にて表されるＮ−スルホニルアミド誘導体及びその塩、
ならびにそれらを有効成分として含有する除草剤を提供
するものである。
次に、一般式（１）で表される化合物の具体的な例を第
１表に示す、化合物番号は以後の記載において参照され
る。
第１表つづき
本発明化合物（１）は、例えば以下に示す反応式（１）
、（２）および（３）に従って製造することができる。
しかし、これらの方法に限定されるものではない。
（、Ｉ）
（式中、Ｚはハロゲン原子、シアノ基、イミダゾリル基
、置換アミジノオキシ基を示し、Ｒ，Ｒ’、ＸおよびＹ
は前記で定義したものと同じ意味を示す、）
一般式（ａ）で示される化合物を適当な溶媒中で等量以
上の縮合剤と、−１０℃から溶媒の沸点の範囲で０．５
時間〜２４時間反応することによって、一般式［ｂ）で
示される中間体化合物を得ることができる。これを単離
するか、または単離することなく一般式（ｃ）で示され
る化合物を等量以上の塩基の存在下、適当な溶媒中で一
１０℃から溶媒の沸点の範囲の温度で０，５時間〜２４
時間反応させることによって、一般式Ｅｌ）で示される
化合物を製造することができる。縮合剤としては塩化チ
オニル、シュウ酸ジクロライド、クロロ炭酸エステル、
カルボニルジイミダゾール、シアノリン酸エステル、カ
ルボジイミド類等が使用できる。溶媒としてはベンゼン
、トルエン、キシレン等の炭化水素系溶媒、塩化メチレ
ン、クロロホルム等のハロゲン化炭化水素系溶媒、ジエ
チルエーテル、エチレングリコールジメチルエーテル。
テトラヒドロフラン、１．４−ジオキサン等のエーテル
類、Ｎ、Ｎ−ジメチルホルムアミド、ジメチルスルホキ
シド等の非プロトン性極性溶媒、その他アセトニトリル
、ピリジン等が使用できる。塩基としては金属ナトリウ
ム、金属カリウム等のアルカリ金属類、水素化ナトリウ
ム、水素化カリウム、水素化カルシウム等の水素化アル
カリ金属及び水素化アルカリ土類金属類、カリウム ｔ
−ブトキシド等のアルカリ金属アルコキシド類、炭酸ナ
トリウム、炭酸カリウム等のアルカリ金属炭酸塩類、水
酸化ナトリウム、水酸化カリウム等の水酸化アルカリ金
属類、トリエチルアミン、ピリジン等の有機アミン類が
使用できる。
反応式（２）
（式中、Ｒ，Ｒ’、ＸおよびＹは前記で定義したものと
同じ意味を示す。）
一般式（１３で示される本発明化合物は、一般式（ａ）
で示される化合物と一般式（ｄ）で示される化合物を、
適当な溶媒中で室温から溶媒の沸点の温度範囲内で５分
〜１０時間反応させることによるか、または触媒量から
当モル以上の塩基の存在下で反応させることにより製造
することができる。ここで溶媒としてはベンゼン、トル
エン。
キシレン等の炭化水素系溶媒、塩化メチレン、りロロホ
ルム等のハロゲン化炭化水素系溶媒、ジエチルエーテル
、エチレングリコールジメチルエーテル、テトラヒドロ
フラン、１．４−ジオキサン等のエーテル系溶媒、アセ
トン、メチルエチルケトン等のケトン系溶媒、酢酸メチ
ル、酢酸エチル等のエステル系溶媒、Ｎ、Ｎ−ジメチル
ホルムアミド、ジメチルスルホキシド等の非プロトン性
極性溶媒、その他アセトニトリル等が使用できる。
塩基としては金属ナトリウム、金属カリウム等のアルカ
リ金属類、水素化ナトリウム、水素化カリウム、水素化
カルシウム等の水素化アルカリ金属及び水素化アルカリ
土類金属類、カリウム １−ブトキシド等のアルカリ金
属アルコキシド類、炭酸ナトリウム、炭酸カリウム、炭
酸カルシウム等の炭酸塩類、水酸化ナトリウム、水酸化
カリウム等の水酸化アルカリ金属類、その他トリエチル
アミン、ピリジン等の有機アミン類が使用できる。
塩基を使用したときは反応後に酸性にして、一般式（１
）で示される化合物を得ることができる。
反応式（３）
（式中、Ｒ，Ｒ’、ＸおよびＹは前記で定義したものと
同じ意味を示す、）
一般式（１）で示される本発明化合物は、一般式［ｅ）
で示される化合物と一般式（ｄ］で示される化合物とを
等量以上の塩基の存在下、適当な溶媒中で一２０℃から
溶媒の沸点の範囲の温度で０．５時間〜２４時間反応さ
せることによって製造することができる。溶−媒として
はベンゼン、トルエン、キシレン等の炭化水素系溶媒、
塩化メチレン、クロロホルム等のハロゲン化炭化水素系
溶媒、ジエチルエーテル、エチレングリコールジメチル
エーテル、テトラヒドロフラン等のエーテル類、Ｎ、Ｎ
−ジメチルホルムアミド、ジメチルスルホキシド等の非
プロトン性極性溶媒、その他アセトニトリル等が使用で
き、塩基としては金属ナトリウム、金属カリウム等のア
ルカリ金属類、ｎ−ブチルリチウム、リチウムジイソプ
ロピルアミド等の有機アルカリ金属類、水素化ナトリウ
ム。
水素化カリウム、水素化カルシウム等の水素化アルカリ
金属及び水素化アルカリ土類金属類、カリウム ｔ−ブ
トキシド等のアルカリ金属アルコキシド類、炭酸ナトリ
ウム、炭酸カリウム等のアルカリ金属炭酸塩類、水酸化
ナトリウム、水酸化カリウム等の水酸化アルカリ金属類
が使用できる。
以上のようにして得られる一般式（１）で示される本発
明化合物は、−船釣な方法により容易にその塩を製造す
ることができる。
次に実施例をあげて本発明化合物の製造法を具体的に説
明する。
実施例１
（Ａ）２−（４，６−シメトキシー２−ピリミジニル）
−３−メチルブチリルイミダゾールの製造法
２− （４，６−シメトキシー２−ピリミジニル）−３
−メチル酪酸５．Ｏｇ、カルボニルジイミダゾール３．
４ｇ、テトラヒドロフラン５０ｍＡを丸底フラスコに取
り、室温で１時間撹拌した。その後、この反応混合物を
氷水中に注ぎ・、５０ｍ１２のジエチルエーテルで２回
抽出した。この抽出液を水洗後、無水硫酸ナトリウムで
一夜乾燥させた。
無機塩を濾別した後、減圧下で溶媒を留去した。
得られた粗結晶をヘキサンで洗浄して無色針状結晶の目
的化合物５．２ｇを得た（収率８６７％）６融点７４〜
７８℃。
（Ｂ）２− （４，６−シメトキシー２−ピリミジニル
）−３−メチル−Ｎ−メチルスルホニル酪酸アミド（化
合物５）の製造法メタンスルホンアミド１．７ｇ、６０
％水素化ナトリウム０，７ｇおよびＮ、Ｎ−ジメチルホ
ルムアミド５０ｍｆｉを丸底フラスコに取り、室温にて
１時間撹拌した。さらに、この反応液中に室温にて（Ａ
）で得られた２−（４，６−シメトキシー２−ピリミジ
ニル）−３−メチルブチリルイミダゾール５．０ｇを加
え、室温にて１時間撹拌したにの反応混合物を氷水中に
注ぎ、希塩酸でｐＨを約３に調整した後、ＬｏｏｍＱの
酢酸エチルで２回抽出した。この抽出液を水洗後、無水
硫酸ナトリウムで一夜乾燥させた。無機塩を濾別した後
。
減圧下で溶媒を留去して、粗結晶４．５ｇを得た。
これをジエチルエーテルから再結晶して無色針状結晶の
目的化合物４．２ｇを得た（収率７６．８％）。融点９
９〜１０２℃。
実施例２
２− （４，６−シメトキシー２−ピリミジニル）−３
−メチル−Ｎ−メチルスルホニル吉草酸アミド（化合物
２７）の製造法
２− （４，６−シメトキシー２−ピリミジニル）−３
−メチル吉草酸５、Ｏｇ、カルボニルジイミダゾール３
．２ｇ、Ｎ、Ｎ−ジメチルホルムアミド３０ｍＡを丸底
フラスコに取り、室温にて１時間撹拌した。メタンスル
ホンアミド１．９ｇ、６０％水素化ナトリウム０．８
ｇおよびＮＮ−ジメチルホルムアミド２０ ｍ Ｑを丸
底フラスコに取り。
室温にて１時間撹拌後、これに上記のようにして調整し
た２−（４，６−シメトキシー２−ピリミジニル）−３
−メチルペンタノイルイミダゾールのＮ，Ｎ−ジメチル
ホルムアミド溶液を室温で滴下した。室温にて３時間撹
拌後、この反応混合物を氷水中に注ぎ，希塩酸でｐｔ＋
を約３に調整し。
１００ｍ１１の酢酸エチルで２回抽出した。この抽出液
を水洗後，無水硫酸ナトリウムで一夜乾燥させた．無機
塩を濾別した後、減圧下で溶媒を留去して、粗結晶５．
８ｇを得た。さらに、これをジエチルエーテルから再結
晶して無色針状結晶の目的化合物５．４ｇを得た（収率
８２，９％）。融点９７〜１０１℃。
実施例３
３−シクロプロピル−２− （４．６−シメトキシー２
−ピリミジニル）−Ｎ−メチルスルホニルプロピオンア
ミド（化合物１９）の製造法
３−シクロプロピル−２− （４．６−シメトキシー２
−ピリミジニル）プロピオン酸３．０ ｇ、メタンスル
ホンアミド１．２ｇおよびピリジン２０ｍｊｌを丸底フ
ラスコに取り、水冷下で撹拌しつつ塩化チオニル１．５
ｇを滴下した．室温にて３時間撹拌後，この反応混合物
を氷水中に注ぎ、希塩酸でｐＨを約３に調整し．１００
ｍ（１の酢酸エチルで２回抽出した。この抽出液を水洗
後、無水硫酸ナトリウムで一夜乾燥させた。無機塩を濾
別した後，減圧下で溶媒を留去して粘稠液体３５ｇを得
た．これをシリカゲルカラムクロマトグラフィー（展開
溶媒ヘキサン：酢酸エチル＝３：１）で精製して無色針
状結晶の目的化合物２．８ｇを得た（収率７１．５％）
、融点９２〜９４℃。
実施例４
２−（３−クロロフェニル） −２−（４．６−シメト
キシー２−ピリミジニル）−Ｎ−メチルスルホン酢酸ア
ミド（化合物１）の製造法
２−（３−クロロベンジル）−４．６−シメトキシー２
−ピリミジン２．６ｇ、６０％水素化ナトリウム０，４
ｇおよびジメチルスルホキシド２０ｍｌ＋を丸底フラス
コに取り、１００”Ｃで０５時間加熱撹拌した。反応液
を室温まで冷却した後、メチルスルホニルイソシアネー
ト１．２ｇを滴下し、そのままの温度で２時間反応させ
た。水５０ｍ１２を加え，希塩酸でｐＨ３〜４に調整し
た後．１００ｍｊｌの酢酸エチルで２回抽出した。この
抽出液を水洗後、無水硫酸ナトリウムで一夜乾燥させた
．無機塩を濾別後、減圧下で溶媒を留去し粘稠液体２．
２ ｇを得た。これをシリカゲルカラムクロマトグラフ
ィー（展開溶媒ヘキサン酢酸エチル＝３：ｌ）で精製し
て淡褐色ガラス状物質の目的化合物１．８ｇを得た（収
率４７，４％）。
屈折率：測定不可。
実施例５
２− （４．６−シメトキシー２−ピリミジニル）−Ｎ
− （２−メトキシカルボニルフェニルスルホニル）酢
酸アミド（化合物３７）の製造法
２− （４．６−シメトキシー２−ピリミジニル）酢酸
１．０ｇ、トリエチルアミン０．５ ｇ、塩化メチレン
５０ｍｆｉを丸底フラスコに取り、室温にて２−メトキ
シカルボニルベンゼンスルホニルイソシアナート１．８
ｇを滴下し、そのままの温度で２時間、さらに加熱ｉｌ
Ａ下で０．５時間反応させた。放冷後、反応液を塩酸で
洗浄し、次いで飽和食塩水で洗浄し、さらに無水硫酸ナ
トリウムで一夜乾燥させた。無機塩を濾別後、減圧下で
溶媒を留去し粘稠液体１．５ｇを得た。これをシリカゲ
ルカラムクロマトグラフィー（展開溶媒ヘキサン：酢酸
エチル＝ｌ：１）で精製して淡黄色粉末結晶の目的化合
物０．７ｇを得た（収率３５４％）。
融点１３１〜１３５℃。
実施例６
２− （４，６−シメトキシー２−ピリミジニル）−３
−メチル−Ｎ−メチルスルホニル酪酸アミドのイソプロ
ピルアミン塩（化合物７）の製造法
２− （４，６−シメトキシー２−ピリミジニル）−３
−メチル−Ｎ−メチルスルホニル酪酸アミド１．９ｇ、
イソプロピルアミン０．４ｇおよびテトラヒドロフラン
２０ｍｇを丸底フラスコに取り。
完全に均一溶液とした後、減圧下で溶媒を留去して淡黄
色ガラス状物質の目的化合物２．２ ｇを得た（収率９
７，６％）。屈折率（ｎ ２°）１．５７１２゜実施例
７
２− （４，６−シメトキシー２−ピリミジニル）−３
−メチル−Ｎ−メチルスルホニル酪酸アミドのナトリウ
ム塩（化合物６）の製造法
２− （４，６−シメトキシー２−ピリミジニル）−３
−メチル−Ｎ−メチルスルホニル酪酸アミド１．５ｇを
２０ｍＡのメタノールに溶解させ、この中に２８％ナト
リウムメトキシド０．９ ｇを加え、均一溶液とした。
減圧下で溶媒を留去し得られた粗結晶をジエチルエーテ
ルで洗浄して白色粉末の目的化合物１．５ｇを得た（収
率９３８％）。
融点１１７〜１２４℃（分解）。
また、本発明化合物［Ｉ］の合成に用いられた反応中間
体〔ａ〕は新規化合物であり、以下に示す合成スキーム
（イ）および（ロ）中の反応式（４）〜（１０）に従っ
て製造することができる。
尚、これらの製造法は、ここに示した方法に限られるも
のではない。
スキーム（イ）
反応式（４）
（式中、Ｒ２はアルキル基を示し２Ｌはハロゲン原子、
アルキルスルホニル基、ベンジルスルホニル基または置
換ベンジルスルホニル基を示し、Ｗはハロゲン原子を示
す。また Ｒ１、Ｘ、Ｙは前記で定義したものと同じ意
味を示す。）一般式（ｈ）で示される化合物は、反応式
（４）中の一般式（ｆ）で示される化合物と一般式［ｇ
］で示される化合物とを当量以上、好ましくは２等量以
上の塩基の存在下、適当な溶媒中で室温から溶媒の沸点
の範囲で、０．５時間〜２４時間反応させることにより
製造することができる。塩基としては金属ナトリウム、
金属カリウム等のアルカリ金属類、水素化ナトリウム、
水素化カリウム７水素化カルシウム等の水素化アルカリ
金属及び水素化アルカリ土類金属類、カリウム し−ブ
トキシド等のアルカリ金属アルコキシド類、炭酸ナトリ
ウム、炭酸カリウム等のアルカリ金属炭酸塩類、水酸化
ナトリウム、水酸化カリウム等の水酸化アルカリ金属類
が使用できる。２当量以上の塩基を使用した時は１反応
後に酸性にして一般式〔ｈ〕で示す化合物を得ることが
できる。また、溶媒としてはベンゼン、トルエン、キシ
レン等の炭化水素系溶媒、塩化メチレン、クロロホルム
等のハロゲン化炭化水素系溶媒、メタノール、エタノー
ル、２−プロパツール等のアルコール系溶媒、ジエチル
エーテル、テトラヒドロフラン、１４−ジオキサン等の
エーテル系溶媒、アセトン、メチルエチルケトン等のケ
トン系溶媒、酢酸メチル、酢酸エチル等のエステル系溶
媒、Ｎ、Ｎ−ジメチルホルムアミド、Ｎ、Ｎ−ジメチル
アセトアミド、ジメチルスルホキシド等の非プロトン性
極性溶媒、その他アセトニトリル等が使用できる。
参考例１
ジエチル ２−（４６−シメトキシー２−ピリミジニル
）マロネートの合成
マロン酸ジエチル５０ｇ、カリウム ｔ−ブトキシド５
２ｇ、Ｎ、Ｎ−ジメチルホルムアミド５００ｍ１！を丸
底フラスコに取り、室温にて撹拌しつつ４．６−シメト
キシー２−メチルスルホニルピリミジン６８ｇを加えた
。室温で５時間撹拌後、反応液に１ａの水を加え５００
ｍ １１のジエチルエーテルで２回抽出した。この抽
出液を水洗後、無水硫酸ナトリウムで一夜乾燥させた。
無機塩を濾別した後、減圧下で溶媒を留去して粘稠液体
８５ｇを得た。これをシリカゲルカラムクロマトグラフ
ィー（展開溶媒ヘキサン：酢酸エチル＝５１）で精製し
て淡黄色液体の目的化合物８０ｇを得た（収率８５．９
％）。屈折率（ｎ％’０．４８４１゜参考例２
ジエチル ２−（４，６−シメトキシー２−ピリミジニ
ル）−２−イソプロピルマロネートの合成
ジエチル２−イソプロピルマロネート６０ｇ。
６０％水素化ナトリウム１．２ｇおよびＮ、Ｎ−ジメチ
ルホルムアミド５０ｍＡを丸底フラスコに取り、６０℃
にて３０分撹拌した後、２−フルオロ−４，６−シメト
キシビリミジン４．７ｇを加えた。
さらに、５時間撹拌後、反応液に１００ｔｒ＋１の水を
加え１００ｍ１１のジエチルエーテルで２回抽出した。
この抽出液を水洗後、無水硫酸ナトリウムで一夜乾燥さ
せた。無機塩を濾別した後、減圧下で溶媒を留去して、
粘稠液体７．２ｇを得た。これをシリカゲルカラムクロ
マトグラフィー（展開溶媒ヘキサン：酢酸エチル＝５：
１）で精製して淡黄色液体の目的化合物６．６ｇを得た
（収率６４７％）、屈折率（ｎ ト０） １ ４８０８
−反応式（５）
（式中、Ｗ、Ｒ’、Ｒ２、ＸおよびＹは前記で定義され
たものと同じ意味を示す。）
一般式［ｈ］で示される化合物は反応式（５）中の一般
式〔ｈ″〕 （ここで、この化合物は反応式（４）の方
法で製造できる；参考例１）で示される化合物と一般式
（ｊ）で示される化合物を当量以上、好ましくは２等量
以上の塩基の存在下、適当な溶媒中で室温から溶媒の沸
点の範囲で、０５時間〜２４時間反応させることにより
製造することができる。塩基としては金属ナトリウム、
金属カリウム等のアルカリ金属類、水素化ナトリウム、
水素化カリウム、水素化カルシウム等の水素化アルカリ
金属及び水素化アルカリ土類金属類、カリウム ｔ−ブ
トキシド等のアルカリ金属アルコキシド類、炭酸ナトリ
ウム、炭酸カリウム等のアルカリ金属炭酸塩類、水酸化
ナトリウム、水酸化カリウム等の水酸化アルカリ金属類
が使用できる。２当量以上の塩基を使用した時は１反応
後に酸性にして一般式（ｈ）で示す化合物を得ることが
できる。また、溶媒としてはベンゼン、トルエン、キシ
レン等の炭化水素系溶媒、塩化メチレン、クロロホルム
等のハロゲン化度化水素系溶媒、メタノール、エタノー
ル、２−プロパツール等のアルコール系溶媒、ジエチル
エーテル、テトラヒドロフラン、１．４−ジオキサン等
のエーテル系溶媒、アセトン、メチルエチルケトン等の
ケトン系溶媒、酢酸メチル、酢酸エチル等のエステル系
溶媒、Ｎ、Ｎ−ジメチルホルムアミド、Ｎ、Ｎ−ジメチ
ルアセトアミド、ジメチルスルホキシド等の非プロトン
性極性溶媒、その他アセトニトリル等が使用できる。
参考例３
ジエチル２− （４，６−シメトキシー２−ピリミジニ
ル）２−ｓｅｃ−ブチルマロネートの合成
ジエチル２− （４，６−シメトキシー２−ピリミジニ
ル）マロネート１００ｇ、６０％水素化ナトリウム１．
５ｇおよびＮ、Ｎ〜ジメチルホルムアミド１００ｍ１２
を丸底フラスコに取り室温にて１時間撹拌した。この溶
液に臭化５ｅｅ−ブチル１７．Ｏｇを湾下し、室温にて
３時間撹拌した。
次いで１反応液に２００ｍｍの水を加えＬｏｏｍＱのジ
エチルエーテルで２回抽出した。この抽出液を水洗後、
無水硫酸ナトリウムで一夜乾燥させた。無機塩を濾別し
た後、減圧下で溶媒を留去して、粘Ｗ液体９．２ ｇ
ｔｒＷ＋た。これをシリカゲルカラムクロマトグラフィ
ー（展開溶媒ヘキサン：酢酸エチル＝１０：１）で精製
して無色粘稠液体の目的化合物８．４ｇを得た（収率７
３，６％）。
屈折率（ｎシ’）１．４７３４゜
反応式（６）
（式中、Ｒ−Ｒ’、Ｒ”、ＸおよびＹは前記で定義した
ものと同じ意味を示す。）
一般式（ａ）で示される化合物は反応式（６）の［ｈ）
で示される化合物を２等量以上、好ましくは４等量以上
塩基の存在下、水または水を含む適当な溶媒中で、室温
から溶媒の沸点の範囲で０５時間〜２４時間反応させた
後、酸性にすることにより製造することができる。塩基
としては水酸化ナトリウム、水酸化カリウム等の水酸化
アルカリ金属類、炭酸ナトリウム、炭酸カリウム等のア
ルカリ金属炭酸塩類、炭酸水素ナトリウム、炭酸水素カ
リウム等のアルカリ金属炭酸水素塩類等が使用できる。
また、溶媒としてはベンゼン、トルエン、キシレン等の
炭化水素系溶媒、塩化メチレン、クロロホルム等のハロ
ゲン化炭化水素系溶媒、メタノール、エタノール、２−
プロパツール等のアルコール系溶媒、ジエチルエーテル
、テトラヒドロフラン、１，４−ジオキサン等のエーテ
ル系溶媒、アセトン、メチルエチルケトン等のケトン系
溶媒、Ｎ、Ｎ−ジメチルホルムアミド、Ｎ、Ｎ−ジメチ
ルアセトアミド、ジメチルスルホキシド等の非プロトン
性極性溶媒、その他アセトニトリル等が使用できる。
参考例４
２− （４，６−シメトキシー２−ピリミジニル）−３
−メチル酪酸の合成
ジエチル２− （４，６−シメトキシー２−ピリミジニ
ル）−２−イソプロピルマロネート１ｏ。
Ｏｇ、水酸化ナトリウＡ５．０ｇ、 水２０ｍｍおよび
メタノール５０ｍｊ＋を丸底フラスコに取り。
加熱還流下６時間撹拌した０反応液を濃縮し１゜Ｏｍｊ
＋の水を加え、水冷下、希塩酸にてｐｉ（３〜４に調整
し、１００ｍＡのジエチルエーテルで２回抽出した。こ
の抽出液を水洗後、無水硫酸ナトリウムで一夜乾燥させ
た。無機塩を濾別した後、減圧下で溶媒を留去して、粗
結晶５．８ｇを得た。
これをジエチルエーテル−ヘキサンから再結晶して無色
針状結晶の目的化合物５．３ｇを得た（収率７５．１％
）、融点９９〜１０１℃。
スキーム（ロ）
［ａ）
反応式（７）
（式中、Ｒ１，Ｒ”、Ｘ及びＹは前記で定義したものと
同じ意味を示す。）
一般式Ｃｍ）で示される化合物は反応式（７）中の［ｈ
’）（ここで、この化合物は反応式（４）の方法で製造
できる；参考例１）で示される化合物を等量以上の塩基
の存在下、アルコール溶媒中で、室温から溶媒の沸点の
範囲で０．５時間〜２４時間反応させた後、酸性にする
ことにより製造することができる。塩基としては水酸化
ナトリウム、水酸化カリウム等の水酸化アルカリ金属類
、金属ナトリウム、金属カリウム等のアルカリ金属類、
水素化ナトリウム、水素化カリウム、水素化カルシウム
等の水素化アルカリ金属及び水素化アルカリ土類金属類
、カリウム ｔ−ブトキシド等のアルカリ金属アルコキ
シド類等が使用できる。
参考例５
メチル ２− （４，６−シメトキシー２−ピリミジニ
ル）アセテートの合成
ジエチル ２− （４，８−ジメトキシ−２−ピリミジ
ニル）マロネート１０．Ｏｇ、２８％ナトリウムメトキ
シドのメタノール溶液７．０ ｇおよびメタノール１０
０ ｍ ｆｔを丸底フラスコに取り、室温にて１０時間
撹拌した。反応液を濃縮し、１００ｍＭの水を加えた後
、希塩酸にてｐＨ３〜４として１００ｍＭのジエチルエ
ーテルで２回抽出した。この抽出液を水洗後、無水硫酸
ナトリウムで一夜乾燥させた。無機塩を濾別した後、減
圧下で溶媒を留去して６．８ｇの液体を得た。この液体
をシリカゲルカラムクロマトグラフィー（展開溶媒ヘキ
サン：酢酸エチル＝１０：１）で精製して無色液体の目
的化合物６．４ｇを得た（収率９０１％）、屈折率（ｎ
シ’Ｈ，４９５９゜反応式（８）
（式中 Ｒ１、Ｒ”、Ｗ、ＸおよびＹは前記で定義され
たものと同じ意味を示す、）
一般式（ｎ）で示される化合物は反応式（８）中の一般
式（ｍ）で示される化合物と一般式（ｊ）で示される化
合物を当量以上、好ましくは２等量以上の塩基の存在下
、適当な溶媒中で室温から溶媒の沸点の範囲で０５時間
〜２４時間反応させることにより製造することができる
。塩基としては金属ナトリウム、金属カリウム等のアル
カリ全属領、水素化ナトリウム、水素化カリウム、水素
化カルシウム等の水素化アルカリ金属及び水素化アルカ
リ土類金属類、カリウム し−ブトキシド等のアルカリ
金属アルコキシド類、炭酸ナトリウム、炭酸カリウム等
のアルカリ金属炭酸塩類、水酸化ナトリウム、水酸化カ
リウム等の水酸化アルカリ金属類が使用できる。２当量
以上の塩基を使用した時は１反応後酸性にして一般式（
ｎ）で示す化合物を得ることができる。また、溶媒とし
てはベンゼン、トルエン、キシレン等の炭化水素系溶媒
、塩化メチレン、クロロホルム等のハロゲン化炭化水素
系溶媒、メタノール、エタノール、２−プロパツール等
のアルコール系溶媒、ジエチルエーテル、テトラヒドロ
フラン、１．４−ジオキサン等のエーテル系溶媒、アセ
トン、メチルエチルケトン等のケトン系溶媒、酢酸メチ
ル、酢酸エチル等のエステル系溶媒、Ｎ、Ｎ−ジメチル
ホルムアミド、Ｎ、Ｎ−ジメチルアセトアミド、ジメチ
ルスルホキシド等の非プロトン性極性溶媒、その他アセ
トニトリル等が使用できる。
参考例６
メチル２− （４，６−シメトキシー２−ピリミジニル
）−２−シクロペンチルアセテートの合成
メチル２− （４，６−シメトキシー２−ピリミジニル
）アセテート１００ｇ、６０％水素化ナトリウム１．５
ｇおよびＮ、Ｎ−ジメチルホルムアミド１００ｍＲを丸
底フラスコに取り、室温にて１時間撹拌した。この溶液
に臭化シクロペンチル８．４ｇを滴下し、６０℃にて５
時間撹拌した。
次いで１反応液に２００ｍＭの水を加え、１００ｍｍの
ジエチルエーテルで２回抽出した。この抽出液を水洗後
、無水硫酸ナトリウムで一夜乾燥させた。無機塩を濾別
した後、減圧下で溶媒を留去して粘稠液体１２．５ ｇ
を得た。これをシリカゲルカラムクロマトグラフィー（
展開溶媒へ・キサン：酢酸エチル＝１０：１）で精製し
て淡黄色液体の目的化合物９．８ｇを得た（収率７４．
２％）。
屈折率（ｎ’、、’）１．５０２０゜
反応式（９）
（式中、Ｒ’、Ｒ２，Ｌ、Ｘ、Ｙは前記で定義したもの
と同じ意味を示す。）
一般式（ｎ）で示される化合物は５反応式（９）中の一
般式（ｆ）で示される化合物と一般式[Industrial Application Field] The present invention relates to novel N-sulfonylamide derivatives and salts thereof, and herbicides containing them as active ingredients. [Prior art] In recent years, many herbicides have been developed, contributing to labor savings and improved productivity in agricultural work. However, these herbicides have specific effects on agricultural crops and weeds. Since there are many indicators, it is necessary to select and use the most effective one depending on the area of application and type of agricultural products. Therefore, developing new compounds that exhibit herbicidal effects has always been an important issue in this field. [Problems to be Solved by the Invention] The present invention is directed to a novel herbicide that contains a compound with a chemical structure different from that of conventionally used herbicides as an active ingredient and can be used in a variety of ways for the cultivation of various crops. The purpose is to provide punishment. [Means for solving the problem] The result of intensive research to achieve the above purpose. Certain N-sulfonylamide derivatives having a pyrimidine ring and their salts are effective in controlling various weeds,
Moreover, they discovered that it is harmless to agricultural crops, leading to the present invention. That is, 1 the present invention relates to the general formula (wherein R represents an alkyl group, a haloalkyl group, or an optionally substituted phenyl group, and R represents a hydrogen atom, an alkyl group, an alkenyl group, a haloalkenyl group, a cycloalkyl group, Represents a cycloalkenyl group, a cycloalkylalkyl group, or an optionally substituted phenyl group,
X and Y are the same or different and represent an alkyl group, an alkoxy group, a haloalkoxy group or a halogen atom)
N-sulfonylamide derivatives and salts thereof,
The present invention also provides herbicides containing these as active ingredients. Next, specific examples of compounds represented by general formula (1) are shown in Table 1, and the compound numbers will be referred to in the subsequent description. Table 1 (Continued) The compound (1) of the present invention can be expressed, for example, by the reaction formula (1) shown below.
, (2) and (3). However, the method is not limited to these methods. (, I) (wherein, Z represents a halogen atom, a cyano group, an imidazolyl group, a substituted amidinooxy group, and R, R', X and Y
has the same meaning as defined above,) The compound represented by general formula (a) is mixed with an equivalent or more amount of condensing agent in a suitable solvent at a temperature of 0.5° C. to 0.5° C. within the boiling point of the solvent.
By reacting for 24 hours to 24 hours, an intermediate compound represented by general formula [b) can be obtained. The compound represented by the general formula (c) can be isolated or without isolation in the presence of an equal or more amount of base in a suitable solvent at a temperature ranging from -10°C to the boiling point of the solvent. ,5 hours to 24
By reacting for a period of time, a compound represented by the general formula El) can be produced. As a condensing agent, thionyl chloride, oxalic acid dichloride, chlorocarbonate,
Carbonyldiimidazole, cyanophosphate, carbodiimides, etc. can be used. Examples of solvents include hydrocarbon solvents such as benzene, toluene and xylene, halogenated hydrocarbon solvents such as methylene chloride and chloroform, diethyl ether and ethylene glycol dimethyl ether. Ethers such as tetrahydrofuran and 1,4-dioxane, aprotic polar solvents such as N,N-dimethylformamide and dimethyl sulfoxide, and others such as acetonitrile and pyridine can be used. Examples of bases include alkali metals such as sodium metal and potassium metal, alkali metal hydrides and alkaline earth metal hydrides such as sodium hydride, potassium hydride, and calcium hydride, and potassium t.
- Alkali metal alkoxides such as butoxide, alkali metal carbonates such as sodium carbonate and potassium carbonate, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, and organic amines such as triethylamine and pyridine can be used. Reaction formula (2) (In the formula, R, R', X and Y have the same meanings as defined above.) The compound of the present invention represented by the general formula (13) has the general formula (a)
The compound represented by and the compound represented by general formula (d),
It can be produced by reacting in a suitable solvent at a temperature ranging from room temperature to the boiling point of the solvent for 5 minutes to 10 hours, or by reacting in the presence of a catalytic amount to an equimolar amount or more of a base. The solvent used here is benzene and toluene. Hydrocarbon solvents such as xylene, halogenated hydrocarbon solvents such as methylene chloride and dichloroform, ether solvents such as diethyl ether, ethylene glycol dimethyl ether, tetrahydrofuran, and 1,4-dioxane, and ketone solvents such as acetone and methyl ethyl ketone. , ester solvents such as methyl acetate and ethyl acetate, aprotic polar solvents such as N,N-dimethylformamide and dimethyl sulfoxide, and acetonitrile. Examples of bases include alkali metals such as sodium metal and potassium metal, alkali metal hydrides and alkaline earth metal hydrides such as sodium hydride, potassium hydride, and calcium hydride, and alkali metal alkoxides such as potassium 1-butoxide. , carbonates such as sodium carbonate, potassium carbonate, and calcium carbonate, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, and organic amines such as triethylamine and pyridine. When a base is used, it is made acidic after the reaction and the general formula (1
) can be obtained. Reaction formula (3) (In the formula, R, R', X and Y have the same meanings as defined above.) The compound of the present invention represented by the general formula (1) has the general formula [e]
A compound represented by formula (d) is reacted with a compound represented by general formula (d) in an appropriate solvent in the presence of an equal or more amount of base at a temperature ranging from -20°C to the boiling point of the solvent for 0.5 to 24 hours. The solvent can be a hydrocarbon solvent such as benzene, toluene, xylene, etc.
Halogenated hydrocarbon solvents such as methylene chloride and chloroform, ethers such as diethyl ether, ethylene glycol dimethyl ether, and tetrahydrofuran, N, N
- Aprotic polar solvents such as dimethylformamide and dimethyl sulfoxide, other acetonitrile, etc. can be used; bases include alkali metals such as sodium metal and potassium metal; organic alkali metals such as n-butyllithium and lithium diisopropylamide; Sodium hydride. Alkali metal hydrides and alkaline earth metal hydrides such as potassium hydride and calcium hydride, alkali metal alkoxides such as potassium t-butoxide, alkali metal carbonates such as sodium carbonate and potassium carbonate, sodium hydroxide, water Alkali metal hydroxides such as potassium oxide can be used. The salt of the compound of the present invention represented by the general formula (1) obtained as described above can be easily produced by a simple method. Next, the method for producing the compound of the present invention will be specifically explained with reference to Examples. Example 1 (A) 2-(4,6-simethoxy2-pyrimidinyl)
-Production method of 3-methylbutylimidazole 2- (4,6-simethoxy2-pyrimidinyl)-3
-Methylbutyric acid5. Og, carbonyldiimidazole3.
4 g and 50 mA of tetrahydrofuran were placed in a round bottom flask and stirred at room temperature for 1 hour. The reaction mixture was then poured into ice water and extracted twice with 50 ml of diethyl ether. This extract was washed with water and then dried over anhydrous sodium sulfate overnight. After filtering off the inorganic salts, the solvent was distilled off under reduced pressure. The obtained crude crystals were washed with hexane to obtain 5.2 g of the target compound in the form of colorless needle-like crystals (yield 867%) 6 Melting point 74~
78℃. (B) Method for producing 2-(4,6-simethoxy2-pyrimidinyl)-3-methyl-N-methylsulfonylbutyric acid amide (compound 5) Methanesulfonamide 1.7 g, 60
% sodium hydride and 50 mfi of N,N-dimethylformamide were placed in a round bottom flask and stirred at room temperature for 1 hour. Furthermore, (A
) was added to 5.0 g of 2-(4,6-simethoxy2-pyrimidinyl)-3-methylbutyrimidazole and stirred at room temperature for 1 hour. The reaction mixture was poured into ice water and adjusted to pH with dilute hydrochloric acid. was adjusted to about 3, and then extracted twice with LoomQ ethyl acetate. This extract was washed with water and then dried over anhydrous sodium sulfate overnight. After filtering off the inorganic salts. The solvent was distilled off under reduced pressure to obtain 4.5 g of crude crystals. This was recrystallized from diethyl ether to obtain 4.2 g of the target compound in the form of colorless needle crystals (yield 76.8%). Melting point 9
9-102℃. Example 2 2-(4,6-simethoxy2-pyrimidinyl)-3
-Methyl-N-methylsulfonylvaleramide (compound 27) production method 2- (4,6-simethoxy2-pyrimidinyl)-3
-Methylvaleric acid 5, Og, carbonyldiimidazole 3
．． 2g, N,N-dimethylformamide (30mA) was placed in a round bottom flask and stirred at room temperature for 1 hour. Methanesulfonamide 1.9g, 60% sodium hydride 0.8
g and 20 m Q of NN-dimethylformamide were placed in a round bottom flask. After stirring at room temperature for 1 hour, 2-(4,6-simethoxy-2-pyrimidinyl)-3 prepared as above was added to this.
- A solution of methylpentanoylimidazole in N,N-dimethylformamide was added dropwise at room temperature. After stirring at room temperature for 3 hours, the reaction mixture was poured into ice water and diluted with dilute hydrochloric acid.
Adjust to about 3. Extracted twice with 100ml of ethyl acetate. This extract was washed with water and dried over anhydrous sodium sulfate overnight. After filtering off the inorganic salt, the solvent was distilled off under reduced pressure to obtain crude crystals.5.
8g was obtained. Further, this was recrystallized from diethyl ether to obtain 5.4 g of the target compound in the form of colorless needle-like crystals (yield: 82.9%). Melting point: 97-101°C. Example 3 3-cyclopropyl-2- (4,6-cymethoxy2
-pyrimidinyl)-N-methylsulfonylpropionamide (compound 19) 3-Cyclopropyl-2- (4.6-cymethoxy2
-Pyrimidinyl)propionic acid (3.0 g), methanesulfonamide (1.2 g) and pyridine (20 mjl) were placed in a round bottom flask, and while stirring under water cooling, 1.5 g of thionyl chloride was added.
g was added dropwise. After stirring at room temperature for 3 hours, the reaction mixture was poured into ice water and the pH was adjusted to about 3 with dilute hydrochloric acid. 100
M (1) was extracted twice with ethyl acetate. This extract was washed with water and dried over anhydrous sodium sulfate overnight. After filtering off the inorganic salts, the solvent was distilled off under reduced pressure to obtain 35 g of a viscous liquid. This was purified by silica gel column chromatography (developing solvent: hexane: ethyl acetate = 3:1) to obtain 2.8 g of the target compound in the form of colorless needle crystals (yield: 71.5%).
, melting point 92-94°C. Example 4 Method for producing 2-(3-chlorophenyl)-2-(4.6-simethoxy-2-pyrimidinyl)-N-methylsulfonic acetamide (compound 1) 2-(3-chlorobenzyl)-4.6- Cymethoxy 2
- 2.6 g of pyrimidine, 60% sodium hydride 0.4
g and 20 ml+ of dimethyl sulfoxide were placed in a round bottom flask and heated and stirred at 100"C for 05 hours. After the reaction solution was cooled to room temperature, 1.2 g of methyl sulfonyl isocyanate was added dropwise, and the reaction was allowed to continue at that temperature for 2 hours. After adding 50 ml of water and adjusting the pH to 3 to 4 with dilute hydrochloric acid, it was extracted twice with 100 mjl of ethyl acetate. The extract was washed with water and dried over anhydrous sodium sulfate overnight. After filtering off the inorganic salts, the mixture was dried under reduced pressure. The solvent is distilled off to form a viscous liquid under 2.
2 g was obtained. This was purified by silica gel column chromatography (developing solvent: hexane ethyl acetate = 3:1) to obtain 1.8 g of the target compound as a pale brown glassy substance (yield: 47.4%). Refractive index: Not measurable. Example 5 2-(4,6-Simethoxy2-pyrimidinyl)-N
- Method for producing (2-methoxycarbonylphenylsulfonyl)acetic acid amide (compound 37) 2- 1.0 g of (4.6-simethoxy2-pyrimidinyl)acetic acid, 0.5 g of triethylamine, and 50 mfi of methylene chloride were placed in a round bottom flask. , 2-methoxycarbonylbenzenesulfonyl isocyanate 1.8 at room temperature
g was added dropwise and heated at the same temperature for 2 hours.
The reaction was carried out under A for 0.5 hours. After cooling, the reaction solution was washed with hydrochloric acid, then with saturated brine, and further dried over anhydrous sodium sulfate overnight. After filtering off the inorganic salts, the solvent was distilled off under reduced pressure to obtain 1.5 g of a viscous liquid. This was purified by silica gel column chromatography (developing solvent: hexane:ethyl acetate = 1:1) to obtain 0.7 g of the target compound as pale yellow powder crystals (yield: 354%). Melting point: 131-135°C. Example 6 2-(4,6-simethoxy2-pyrimidinyl)-3
-Production method of isopropylamine salt of methyl-N-methylsulfonylbutyric acid amide (compound 7) 2- (4,6-Simethoxy2-pyrimidinyl)-3
-Methyl-N-methylsulfonylbutyric acid amide 1.9 g,
Take 0.4 g of isopropylamine and 20 mg of tetrahydrofuran into a round bottom flask. After making a completely homogeneous solution, the solvent was distilled off under reduced pressure to obtain 2.2 g of the target compound as a pale yellow glassy substance (yield: 9
7.6%). Refractive index (n 2°) 1.5712° Example 7 2-(4,6-Simethoxy2-pyrimidinyl)-3
-Production method of sodium salt of methyl-N-methylsulfonylbutyric acid amide (compound 6) 2- (4,6-Simethoxy2-pyrimidinyl)-3
1.5 g of -methyl-N-methylsulfonylbutyric acid amide was dissolved in methanol at 20 mA, and 0.9 g of 28% sodium methoxide was added thereto to form a homogeneous solution. The solvent was distilled off under reduced pressure, and the resulting crude crystals were washed with diethyl ether to obtain 1.5 g of the desired compound as a white powder (yield: 938%). Melting point 117-124°C (decomposed). Furthermore, the reaction intermediate [a] used in the synthesis of the compound [I] of the present invention is a new compound, and according to reaction formulas (4) to (10) in the synthesis schemes (a) and (b) shown below, can be manufactured. Note that these manufacturing methods are not limited to the methods shown here. Scheme (a) Reaction formula (4) (In the formula, R2 represents an alkyl group and 2L is a halogen atom,
It represents an alkylsulfonyl group, a benzylsulfonyl group or a substituted benzylsulfonyl group, and W represents a halogen atom. Furthermore, R1, X, and Y have the same meanings as defined above. ) The compound represented by the general formula (h) is a compound represented by the general formula (f) in the reaction formula (4) and the general formula [g
] in the presence of an equivalent or more, preferably 2 or more equivalents of a base in a suitable solvent in the range from room temperature to the boiling point of the solvent for 0.5 to 24 hours. I can do it. As a base, metallic sodium,
Alkali metals such as metallic potassium, sodium hydride,
Alkali metal hydrides and alkaline earth metal hydrides such as potassium 7-calcium hydride, alkali metal alkoxides such as potassium butoxide, alkali metal carbonates such as sodium carbonate and potassium carbonate, sodium hydroxide, water Alkali metal hydroxides such as potassium oxide can be used. When a base of 2 equivalents or more is used, the compound represented by the general formula [h] can be obtained by making it acidic after one reaction. Examples of solvents include hydrocarbon solvents such as benzene, toluene and xylene, halogenated hydrocarbon solvents such as methylene chloride and chloroform, alcohol solvents such as methanol, ethanol and 2-propanol, diethyl ether, tetrahydrofuran, etc. -Ether solvents such as dioxane, ketone solvents such as acetone and methyl ethyl ketone, ester solvents such as methyl acetate and ethyl acetate, aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, etc. Solvents such as acetonitrile can be used. Reference Example 1 Synthesis of diethyl 2-(46-simethoxy-2-pyrimidinyl)malonate 50 g of diethyl malonate, 5 g of potassium t-butoxide
2g, N,N-dimethylformamide 500ml! was placed in a round bottom flask, and 68 g of 4,6-simethoxy-2-methylsulfonylpyrimidine was added thereto while stirring at room temperature. After stirring at room temperature for 5 hours, water from 1a was added to the reaction solution and the mixture was heated to 500 ml.
Extracted twice with m 11 diethyl ether. This extract was washed with water and then dried over anhydrous sodium sulfate overnight. After filtering off the inorganic salts, the solvent was distilled off under reduced pressure to obtain 85 g of a viscous liquid. This was purified by silica gel column chromatography (developing solvent: hexane: ethyl acetate = 51) to obtain 80 g of the target compound as a pale yellow liquid (yield: 85.9
%). Refractive index (n%'0.4841° Reference Example 2 Synthesis of diethyl 2-(4,6-simethoxy-2-pyrimidinyl)-2-isopropylmalonate Diethyl 2-isopropylmalonate 60g. 60% sodium hydride 1.2g and 50 mA of N,N-dimethylformamide in a round bottom flask and heated to 60°C.
After stirring for 30 minutes, 4.7 g of 2-fluoro-4,6-cymethoxypyrimidine was added. Furthermore, after stirring for 5 hours, 100 tr+1 of water was added to the reaction solution, and the mixture was extracted twice with 100 ml of diethyl ether. This extract was washed with water and then dried over anhydrous sodium sulfate overnight. After filtering off the inorganic salts, the solvent was distilled off under reduced pressure.
7.2 g of viscous liquid was obtained. This was subjected to silica gel column chromatography (developing solvent: hexane: ethyl acetate = 5:
1) to obtain 6.6 g of the target compound as a pale yellow liquid (yield 647%), refractive index (n 0) 1 4808
- Reaction formula (5) (In the formula, W, R', R2, X and Y have the same meanings as defined above.) The compound represented by the general formula [h] is The compound represented by the general formula [h''] (where this compound can be produced by the method of reaction formula (4); Reference Example 1) and the compound represented by the general formula (j) are mixed in equal or more equivalent amounts, preferably 2 It can be produced by reacting in a suitable solvent in a range from room temperature to the boiling point of the solvent for 05 to 24 hours in the presence of an equal or more amount of base.The base includes metallic sodium,
Alkali metals such as metallic potassium, sodium hydride,
Alkali metal hydrides and alkaline earth metal hydrides such as potassium hydride and calcium hydride, alkali metal alkoxides such as potassium t-butoxide, alkali metal carbonates such as sodium carbonate and potassium carbonate, sodium hydroxide, water Alkali metal hydroxides such as potassium oxide can be used. When a base of 2 equivalents or more is used, the compound represented by the general formula (h) can be obtained by making it acidic after one reaction. In addition, as a solvent, hydrocarbon solvents such as benzene, toluene, and xylene, halogenated hydrogen dihydride solvents such as methylene chloride and chloroform, alcohol solvents such as methanol, ethanol, and 2-propanol, diethyl ether, tetrahydrofuran, 1. Ether solvents such as 4-dioxane, ketone solvents such as acetone and methyl ethyl ketone, ester solvents such as methyl acetate and ethyl acetate, and non-containing solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and dimethyl sulfoxide. Protic polar solvents and other solvents such as acetonitrile can be used. Reference Example 3 Synthesis of diethyl 2- (4,6-simethoxy 2-pyrimidinyl) 2-sec-butyl malonate 100 g of diethyl 2- (4,6-simethoxy 2-pyrimidinyl) malonate, 60% sodium hydride 1.
5g and N,N~dimethylformamide 100m12
The mixture was placed in a round bottom flask and stirred at room temperature for 1 hour. Add 17.5ee-butyl bromide to this solution. Og was added and stirred at room temperature for 3 hours. Next, 200 mm of water was added to one reaction solution, and the mixture was extracted twice with LoomQ diethyl ether. After washing this extract with water,
It was dried over anhydrous sodium sulfate overnight. After filtering off the inorganic salts, the solvent was distilled off under reduced pressure to obtain 9.2 g of viscous W liquid.
trW+ta. This was purified by silica gel column chromatography (developing solvent: hexane: ethyl acetate = 10:1) to obtain 8.4 g of the target compound as a colorless viscous liquid (yield: 7
3.6%). Refractive index (n') 1.4734° Reaction formula (6) (In the formula, R-R', R", X and Y have the same meanings as defined above.) In the general formula (a) The compound shown is [h] in reaction formula (6)
After reacting the compound represented by 2 equivalents or more, preferably 4 equivalents or more of a base in water or a suitable solvent containing water for 05 to 24 hours in the range from room temperature to the boiling point of the solvent, It can be produced by making it acidic. As the base, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, alkali metal carbonates such as sodium carbonate and potassium carbonate, and alkali metal hydrogen carbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate can be used. In addition, as a solvent, hydrocarbon solvents such as benzene, toluene and xylene, halogenated hydrocarbon solvents such as methylene chloride and chloroform, methanol, ethanol, 2-
Alcohol solvents such as propatool, ether solvents such as diethyl ether, tetrahydrofuran, and 1,4-dioxane, ketone solvents such as acetone and methyl ethyl ketone, N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, etc. Other aprotic polar solvents such as acetonitrile can be used. Reference example 4 2-(4,6-simethoxy2-pyrimidinyl)-3
-Synthesis of methylbutyric acid Diethyl 2- (4,6-simethoxy 2-pyrimidinyl)-2-isopropylmalonate 1o. Take Og, 5.0 g of sodium hydroxide A, 20 mm of water, and 50 mj+ of methanol in a round bottom flask. The reaction solution was stirred for 6 hours under heating under reflux and concentrated to 1゜Omj.
+ water was added, the pi was adjusted to 3 to 4 with dilute hydrochloric acid under water cooling, and extracted twice with 100 mA of diethyl ether. After washing this extract with water, it was dried overnight with anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure to obtain 5.8 g of crude crystals. This was recrystallized from diethyl ether-hexane to obtain 5.3 g of the target compound in the form of colorless needle-like crystals. Rate 75.1%
), melting point 99-101°C. Scheme (b) [a) Reaction formula (7) (In the formula, R1, R'', X and Y have the same meanings as defined above.) The compound represented by general formula Cm) is represented by reaction formula (7). ) in [h
') (Here, this compound can be produced by the method of reaction formula (4); Reference Example 1) in an alcoholic solvent in the presence of an equal or more amount of base, in a range from room temperature to the boiling point of the solvent. It can be produced by reacting for 0.5 to 24 hours and then making it acidic. As a base, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, alkali metals such as metallic sodium and metallic potassium,
Alkali metal hydrides and alkaline earth metal hydrides such as sodium hydride, potassium hydride, and calcium hydride, alkali metal alkoxides such as potassium t-butoxide, and the like can be used. Reference Example 5 Synthesis of methyl 2-(4,6-simethoxy-2-pyrimidinyl)acetate Diethyl 2-(4,8-dimethoxy-2-pyrimidinyl)malonate 10. Og, 7.0 g of 28% sodium methoxide in methanol and 10 g of methanol
0 m ft was placed in a round bottom flask and stirred at room temperature for 10 hours. The reaction solution was concentrated, 100 mM water was added, the pH was adjusted to 3 to 4 with diluted hydrochloric acid, and the mixture was extracted twice with 100 mM diethyl ether. This extract was washed with water and then dried over anhydrous sodium sulfate overnight. After filtering off the inorganic salts, the solvent was distilled off under reduced pressure to obtain 6.8 g of liquid. This liquid was purified by silica gel column chromatography (developing solvent: hexane: ethyl acetate = 10:1) to obtain 6.4 g of the target compound as a colorless liquid (yield 901%), refractive index (n
shi'H,4959゜Reaction formula (8) (In the formula, R1, R", W, X and Y have the same meanings as defined above.) The compound represented by the general formula (m) in (8) and the compound represented by the general formula (j) are mixed in an appropriate solvent from room temperature to the boiling point of the solvent in the presence of an equivalent or more, preferably two or more equivalents of a base. It can be produced by reacting for 05 to 24 hours within the range of Alkaline earth metal hydrides, alkali metal alkoxides such as potassium butoxide, alkali metal carbonates such as sodium carbonate and potassium carbonate, and alkali metal hydroxides such as sodium hydroxide and potassium hydroxide can be used.2 When an equivalent or more base is used, it is acidified after one reaction and the general formula (
A compound represented by n) can be obtained. Examples of solvents include hydrocarbon solvents such as benzene, toluene and xylene, halogenated hydrocarbon solvents such as methylene chloride and chloroform, alcohol solvents such as methanol, ethanol and 2-propanol, diethyl ether, tetrahydrofuran, etc. Ether solvents such as 4-dioxane, ketone solvents such as acetone and methyl ethyl ketone, ester solvents such as methyl acetate and ethyl acetate, aprotons such as N,N-dimethylformamide, N,N-dimethylacetamide, and dimethylsulfoxide. Other polar solvents such as acetonitrile can be used. Reference Example 6 Synthesis of methyl 2- (4,6-simethoxy 2-pyrimidinyl)-2-cyclopentyl acetate 100 g of methyl 2- (4,6-simethoxy 2-pyrimidinyl) acetate, 1.5 g of 60% sodium hydride
100 mR of N,N-dimethylformamide were placed in a round bottom flask and stirred at room temperature for 1 hour. 8.4 g of cyclopentyl bromide was added dropwise to this solution, and
Stir for hours. Next, 200 mM water was added to one reaction solution, and the mixture was extracted twice with 100 mm diethyl ether. This extract was washed with water and then dried over anhydrous sodium sulfate overnight. After filtering off the inorganic salts, the solvent was distilled off under reduced pressure to obtain 12.5 g of viscous liquid.
I got it. This was carried out using silica gel column chromatography (
Purification was performed using a developing solvent (xane:ethyl acetate = 10:1) to obtain 9.8 g of the target compound as a pale yellow liquid (yield: 74.
2%). Refractive index (n',,') 1.5020° Reaction formula (9) (In the formula, R', R2, L, X, and Y have the same meanings as defined above.) General formula (n) The compound represented by the general formula (f) in 5 reaction formula (9) and the general formula
〔０〕で示される
化合物とを当量以上、好ましくは２等量以上の塩基の存
在下、適当な溶媒中で一２０℃から溶媒の沸点の範囲で
、０．５時間〜２４時間反応させることにより製造する
ことができる。塩基としては金属ナトリウム、金属カリ
ウム等のアルカリ金属類、ｎ−ブチルリチウム、リチウ
ムジイソプロピルアミド等の有機アルカリ金属類、水素
化ナトリウム、水素化カリウム、水素化カルシウム等の
水素化アルカリ金属及び水素化アルカリ土類金属類、カ
リウム ｔ−ブトキシド等のアルカリ金属アルコキシド
類、炭酸ナトリウム、炭酸カリウム等のアルカリ金属炭
酸塩類、水酸化ナトリウム、水酸化カリウム等の水酸化
アルカリ金属類が使用できる。２当量以上の塩基を使用
した時は、反応後に酸性にして、一般式［ｎ］で示す化
合物を得ることができる。また、溶媒としてはベンゼン
、トルエン、キシレン等の炭化水素系溶媒、塩化メチレ
ン、クロロホルム等のハロゲン化炭化水素系溶媒、メタ
ノール、エタノール、２−プロパツール等のアルコール
系溶媒、ジエチルエーテル、テトラヒドロフラン、１．
４−ジオキサン等のエーテル系溶媒、アセトン、メチル
エチルケトン等のケトン系溶媒、酢酸メチル、酢酸エチ
ル等の工′ステル系溶媒、Ｎ、Ｎ−ジメチルホルムアミ
ド、Ｎ、Ｎ−ジメチルアセトアミド、ジメチルスルホキ
シド等の非プロトン性極性溶媒、その他７セトニトリル
等が使用できる。
参考例７
エチル ２− （４，６−シメトキシー２−ピリミジニ
ル）−２−ｔ−ブチルアセテートの合成
エチル ｔ−ブチルアセテート１８．０ｇ、テトラヒド
ロフラン１００ ｍ Ｑを丸底フラスコに取り、２０℃
にて撹拌しつつリチウムジイソプロピルアミドの１．５
Ｍシクロヘキサン溶液１００ｍ１ｌを１時間で滴下した
。−２０℃で１時間撹拌後。
４．６−シメトキシー２−メチルスルホニルピリミジン
２７．０ ｇを加え一１０℃〜０℃で５時間撹拌後、反
応液にＩＱの水を加え２００ ｍ ｌのジエチルエーテ
ルで２回抽出した。この抽出液を水洗後、無水硫酸ナト
リウムで一夜乾燥させた。無機塩を濾別した後、減圧下
で溶媒を留去して粘稠液体３６．２ｇを得た。これをシ
リカゲルカラムクロマトグラフィー（展開溶媒ヘキサン
、酢酸エチル＝１０：１）で精製して淡黄色液体の目的
化合物１２．３ ｇを得た（収率３１．４％）。屈折率
（ｎ”） １．４７５８
ア
反応式（１０）
（式中 Ｒ１、Ｒ″、ＸおよびＹは前記で定義したもの
と同じ意味を示す、）
一般式（ａｌで示される化合物は反応式（９）中の（ｎ
）で示される化合物を等量以上、好ましくは２等量以上
塩基の存在下、水または水を含む適当な溶媒中で、室温
から溶媒の沸点の範囲で０５時間〜２４時間反応させた
後、酸性にすることにより製造することができる。塩基
としては水酸化ナトリウム、水酸化カリウム等の水酸化
アルカリ金属類、炭酸ナトリウム、炭酸カリウム等のア
ルカリ金属炭酸塩類、炭酸水素ナトリウム、炭酸水素カ
リウム等のアルカリ金属炭酸水素塩類が使用できる。ま
た、溶媒としてはベンゼン、トルエン、キシレン等の炭
化水素系溶媒、塩化メチレン、クロロホルム等のハロゲ
ン化炭化水素系溶媒、メタノール、エタノール、２−プ
ロパツール等のアルコール系溶媒、ジエチルエーテル、
テトラヒドロフラン、１．４−ジオキサン等のエーテル
系溶媒、アセトン、メチルエチルケトン等のケトン系溶
媒、Ｎ、Ｎ−ジメチルホルムアミド、Ｎ、Ｎ−ジメチル
アセトアミド、ジメチルスルホキシド等の非プロトン性
極性溶媒、その他アセトニトリル等が使用できる。
参考例８
２− （４，６−シメトキシー２−ピリミジニル）−２
−ｔ−ブチル酢酸の合成
エチル ２− （４，６−シメトキシー２−ピリミジニ
ル）−２−ｔ−ブチルアセテート１０．０ ｇ、水酸化
ナトリウム５．０ｇ、水２０ｍＭおよびメタノール１０
０ｍＭを丸底フラスコに取り、加熱還流下６時間撹拌し
た。反応液を濃縮し、１００ｍ１１の水を加え、水冷下
、希塩酸にてｐＨ３〜４に調整し、１００ｍ１１のジエ
チルエーテルで２回抽出した。この抽出液を水洗後２無
水硫酸ナトリウムで一夜乾燥させた。無機塩を濾別した
後、減圧下で溶媒を留去して、粗結晶７．８ ｇを得た
。
これをジエチルエーテル−ヘキサンから再結晶して目的
化合物７．３ｇを得た（収率８１．１％）。
融点７６〜７７℃。
上記のようにして得られた中間体［ａ）的な具体例を第
２表に示す。
の代表
第１表つづき
（以下余白）
本発明の除草剤は、一般式（１）で示されるＮ−スルホ
ニルアミド誘導体及びその塩を有効成分としてなる。
本発明化合物を除草剤として水田、畑地、樹園地、非農
耕地等に使用する場合、その目的に応じて有効成分を適
当な剤型で用いることができる。
通常の場合は有効成分を不活性な液体または固体の担体
で希釈し、必要に応じて界面活性剤１分散剤、補助剤等
を配合して、粉剤、水和剤、乳剤。
粒剤等の各種形態に製剤して使用することができる。製
剤化に際して用いられる担体としては１例えばジ−クラ
イト、タルク、ベントナイト、クレー、カオリン、珪藻
土、ホワイトカーボン５バーミキユライト、消石灰、珪
砂、硫安、尿素等の固体担体、イソプロピルアルコール
、キシレン、シクロヘキサノン、メチルナフタレン等の
液体担体等があげられる。界面活性剤及び分散剤として
は、例えばアルコール硫酸エステル塩、アルキルアリー
ルスルホン酸塩、リグニンスルホン酸塩、ポリオキシエ
チレングリコールエーテル、ポリオキシエチレンアルキ
ルアリールエーテル、ポリオキンエチレンソルビタンモ
ノアルキレート等があげられる。補助剤としては、例え
ばカルボキシメチルセルロース、ポリエチレングリコー
ル、アラビアゴム等があげられる。使用に際しては、適
当な濃度に希釈して散布するかまたは直接施用する。本
発明化合物は有効成分で１０アール当り０．１ｇ〜ＩＫ
ｇ施用する。
また、本発明の化合物は必要に応じて殺虫剤、殺菌剤、
他の除草剤、植物生長調節剤、肥料等と混用してもよい
。
次に代表的な製剤例をあげて製剤方法を具体的に説明す
る。以下の説明において「部」は重量部を意味する。
製剤例１ 水和剤
化合物（５）の１０部にエマルゲン８１０（花王株式会
社の登録商標）の０．５部、デモールＮ（花王株式会社
の登録商標）の０．５部、クニライト２０１（クニミネ
工業株式会社の登録商標）の２０部、ジ−クライトＣＡ
（ジ−クライト株式会社の登録商標）の６９部を混合粉
砕し、水和剤を得る。
製剤例２ 水和剤
化合物（１１）の１０部にエマルゲン８１０の０．５部
、デモールＮの０５部、クニライト２０１の２０部、カ
ープレックス８０の５部、ジ−クライトＣＡの６４部を
混合粉砕し、水和剤を得る。
製剤例３ 乳剤
化合物（１４）の３０部にキシレンとイソホロンの等景
況合物６０部、界面活性剤ツルポール８００Ａ （東邦
化学工業株式会社の登録商標）の１０部を加え、これら
をよくかきまぜることによって乳剤を得る。
製剤例４ 粒剤
化合物（２７）の１０部、タルクとベントナイトを１＝
３の割合の混合した増量剤の８０部、ホワイトカーボン
の５部、界面活性剤ツルポール８００Ａの５部に水１０
部を加え、よく練ってペースト状としたものを直径０．
７１のふるい穴から押し出して乾燥した後に０．５〜１
１諷の長さに切断し１粒剤を得る。
［発明の効果］
一般式（１）で表される本発明の化合物及びその塩は、
水田に発生するタイヌビエ、タマガヤツリ、コナギ等の
一年生雑草及びウリカワ、ミズガヤツリ、クログワイ、
ホタルイ、ヘラオモダカ等の多年生雑草の発芽時から生
育期の広い範囲にわたって、極めて低い薬量で優れた除
草効果を発揮する。また、畑地においても問題となる種
々の雑草、例えばオオイヌタデ、アオビユ、シロザ、ハ
コベ、イチビ、アメリカキンゴジカ、アサガオ。
オナモミ等の広葉雑草をはじめ、ハマスゲ、キハマスゲ
、ヒメクグ、カヤツリグサ、コゴメガヤツリ等の多年生
および１年生カヤツリグサ科雑草。
ヒエ、メヒシバ、エノコログサ、スズメノカタビラ、ジ
ョンソングラス、ノスズメノテッポウ、野生エンバク等
のイネ科雑草を有効に防除することができる。一方、本
発明の除草剤は作物に対する安全性が高く、中でも稲、
小麦、大麦、大豆及び棉等に対して高い安全性を示す。
次に試験例をあげて本発明化合物の奏する効果を説明す
る６
試験例１（水田土壌処理による除草効果試験）１００
ｃｍ’のプラスチックポットに水田土壌を充填し１代掻
後、タイヌビエ（Ｅｃ）、コナギ（ＭＯ）及びホタルイ
（Ｓｃ）の各種子を播種し、水深３Ｃ■に湛水した。翌
日、製剤例１に準じて調製した水和剤を水で希釈し、水
面滴下処理した。施用量は、有効成分を１０アール当り
１００ｇとした。その後、温室内で育成し、処理２１日
目に第３表の基準に従い、除草効果を調査した。その結
果を第４表に示した。
第３表
第４表
５表に示す。
第５表
第４表つづき
試験例２（畑地土壌処理による除草効果試験）１２０
ｃｍ”プラスチックポットに畑地土壌を充填し１食用ビ
ニ（Ｅｃ）、オオイヌタデ（Ｐｏ）、アオビユ（Ａ鳳）
、シロザ（Ｃｈ）、コゴメガヤッリ（ＣＤの各種子を播
種して覆土した。製剤例１に準じて調製した水和剤を水
で希釈し、１０アール当り有効成分が１００ｇになる様
に、１０アール当りＬｏｏＱを小型噴霧器で土壌表面に
均一に散布した。その後、温室内で育成し、処理２１日
目抜第３表の基準に従って、除草効果を調査した。その
結果を第第５表つづき
試験例３（畑地茎葉処理による除草効果試験）１２０
ｃｍ”プラスチックポットに畑地土壌を充填し、食用ビ
ニ（Ｅｃ）、オオイヌタデ（Ｐｏ）、アオビユ（ＡＩ）
、シロザ（Ｃｈ）、コゴメガヤッリの（Ｃｉ）各種子を
播種し、温室内で２週間育成後、製剤例１に準じて調製
した水和剤を水に希釈し、１０アール当り有効成分が１
００ｇになる様に、１０アール当り１００Ｑを小型噴霧
器で植物体の上方から全体に茎葉散布処理した。その後
、温室内で育成し。
処理１４日１に第３表の基準に従って、除草効果を調査
した。その結果を第６表に示す。
第６表
第６表のつづき
試験例４（畑地土壌処理における薬効・薬害試験）６０
０ ｃｍ”プラスチックポット各々に畑地土壌を充填し
、大豆（Ｇ ｌ ＞ 、棉（Ｇｏ）、ヒエ（Ｅｃ）、オ
オイヌタデ（Ｐｏ）、アオビユ（Ａ議）、シロザ（Ｃｈ
）、イチビ（＾ｂ）及びノアサガオ（Ｉｐ）を播種し、
ハマスゲ（Ｃｒ）の塊茎を置床して覆土した６ポツト底
部より吸水させた後、製剤例１に準じて調製した水和剤
を所定有効成分量（２５ｇ／１．（！ａ）となるように
、１０アール当り１００１ｍの水で希釈し、小型噴霧器
で土壌表面に散布処理した。処理後再び温室内で育成し
。
処理２０日０に第３表の基準に従って、除草効果及び薬
害を調査した。その結果を第７表に示す。
第７表
特許出原人
クミアイ化学工業株式会社
イハラケミカル工業株式会社Reacting the compound represented by [0] in the presence of an equivalent or more, preferably 2 or more equivalents of a base in a suitable solvent at a temperature ranging from -20°C to the boiling point of the solvent for 0.5 to 24 hours. It can be manufactured by Examples of bases include alkali metals such as sodium metal and potassium metal, organic alkali metals such as n-butyllithium and lithium diisopropylamide, alkali metal hydrides and alkali hydrides such as sodium hydride, potassium hydride, and calcium hydride. Earth metals, alkali metal alkoxides such as potassium t-butoxide, alkali metal carbonates such as sodium carbonate and potassium carbonate, and alkali metal hydroxides such as sodium hydroxide and potassium hydroxide can be used. When a base of 2 equivalents or more is used, the compound represented by the general formula [n] can be obtained by making it acidic after the reaction. Examples of solvents include hydrocarbon solvents such as benzene, toluene and xylene, halogenated hydrocarbon solvents such as methylene chloride and chloroform, alcohol solvents such as methanol, ethanol and 2-propanol, diethyl ether, tetrahydrofuran, etc. ．．
Ether solvents such as 4-dioxane, ketone solvents such as acetone and methyl ethyl ketone, ester solvents such as methyl acetate and ethyl acetate, non-carbon solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and dimethyl sulfoxide. Protic polar solvents and other solvents such as 7cetonitrile can be used. Reference Example 7 Synthesis of ethyl 2-(4,6-simethoxy-2-pyrimidinyl)-2-t-butyl acetate 18.0 g of ethyl t-butyl acetate and 100 m of tetrahydrofuran were placed in a round bottom flask and heated at 20°C.
1.5 of lithium diisopropylamide while stirring at
100ml of M cyclohexane solution was added dropwise over 1 hour. After stirring for 1 hour at -20°C. After adding 27.0 g of 4.6-simethoxy-2-methylsulfonylpyrimidine and stirring at -10°C to 0°C for 5 hours, IQ water was added to the reaction mixture and extracted twice with 200 ml of diethyl ether. This extract was washed with water and then dried over anhydrous sodium sulfate overnight. After filtering off the inorganic salts, the solvent was distilled off under reduced pressure to obtain 36.2 g of a viscous liquid. This was purified by silica gel column chromatography (developing solvent: hexane, ethyl acetate = 10:1) to obtain 12.3 g of the target compound as a pale yellow liquid (yield: 31.4%). Refractive index (n'') 1.4758 A Reaction formula (10) (In the formula, R1, R'', X and Y have the same meanings as defined above.) General formula (The compound represented by al is the reaction formula (9) inside (n
) in the presence of an equivalent or more, preferably 2 or more equivalents of a base in water or a suitable solvent containing water in a range from room temperature to the boiling point of the solvent for 05 to 24 hours, and then It can be produced by making it acidic. As the base, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, alkali metal carbonates such as sodium carbonate and potassium carbonate, and alkali metal hydrogen carbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate can be used. Examples of solvents include hydrocarbon solvents such as benzene, toluene, and xylene, halogenated hydrocarbon solvents such as methylene chloride and chloroform, alcohol solvents such as methanol, ethanol, and 2-propanol, diethyl ether,
Ether solvents such as tetrahydrofuran and 1,4-dioxane, ketone solvents such as acetone and methyl ethyl ketone, aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and dimethyl sulfoxide, and other acetonitrile. Can be used. Reference example 8 2-(4,6-simethoxy2-pyrimidinyl)-2
Synthesis of -t-butylacetic acid Ethyl 2-(4,6-simethoxy-2-pyrimidinyl)-2-t-butylacetate 10.0 g, sodium hydroxide 5.0 g, water 20 mM and methanol 10
0mM was placed in a round bottom flask and stirred under heating under reflux for 6 hours. The reaction solution was concentrated, 100 ml of water was added, the pH was adjusted to 3 to 4 with dilute hydrochloric acid under water cooling, and the mixture was extracted twice with 100 ml of diethyl ether. This extract was washed with water and dried over dianhydrous sodium sulfate overnight. After filtering off the inorganic salt, the solvent was distilled off under reduced pressure to obtain 7.8 g of crude crystals. This was recrystallized from diethyl ether-hexane to obtain 7.3 g of the target compound (yield: 81.1%). Melting point 76-77°C. Specific examples of the intermediate [a) obtained as described above are shown in Table 2. Representative Table 1 (Continued below) The herbicide of the present invention contains an N-sulfonylamide derivative represented by the general formula (1) and a salt thereof as an active ingredient. When the compound of the present invention is used as a herbicide in rice fields, fields, orchards, non-agricultural lands, etc., the active ingredient can be used in an appropriate dosage form depending on the purpose. Usually, the active ingredient is diluted with an inert liquid or solid carrier, and if necessary, surfactants, dispersants, adjuvants, etc. are added to form powders, wettable powders, and emulsions. It can be formulated and used in various forms such as granules. Examples of carriers used in formulation include solid carriers such as dicrite, talc, bentonite, clay, kaolin, diatomaceous earth, white carbon 5 vermiculite, slaked lime, silica sand, ammonium sulfate, urea, isopropyl alcohol, xylene, cyclohexanone, Examples include liquid carriers such as methylnaphthalene. Examples of surfactants and dispersants include alcohol sulfate ester salts, alkylaryl sulfonates, lignin sulfonates, polyoxyethylene glycol ethers, polyoxyethylene alkylaryl ethers, and polyquine ethylene sorbitan monoalkylates. . Examples of the adjuvant include carboxymethyl cellulose, polyethylene glycol, and gum arabic. When used, it can be diluted to an appropriate concentration and sprayed, or applied directly. The compound of the present invention is an active ingredient of 0.1 g to IK per 10 ares.
g Apply. In addition, the compound of the present invention may be used as an insecticide, fungicide, or
It may be used in combination with other herbicides, plant growth regulators, fertilizers, etc. Next, the formulation method will be specifically explained using typical formulation examples. In the following description, "part" means part by weight. Formulation Example 1 10 parts of wettable powder compound (5), 0.5 part of Emulgen 810 (registered trademark of Kao Corporation), 0.5 part of Demol N (registered trademark of Kao Corporation), Kunilite 201 (Kunimine 20 copies of Zeekrite CA (registered trademark of Kogyo Co., Ltd.)
(registered trademark of Zeeklite Co., Ltd.) were mixed and ground to obtain a wettable powder. Formulation Example 2 Mix 0.5 parts of Emulgen 810, 0.5 parts of Demol N, 20 parts of Kunilite 201, 5 parts of Carplex 80, and 64 parts of Zikrite CA to 10 parts of wettable powder compound (11). Grind to obtain a wettable powder. Formulation Example 3 By adding 60 parts of a compound of xylene and isophorone and 10 parts of the surfactant Tsurupol 800A (registered trademark of Toho Chemical Industry Co., Ltd.) to 30 parts of emulsion compound (14) and stirring these thoroughly. Obtain emulsion. Formulation Example 4 10 parts of granule compound (27), 1 = talc and bentonite
80 parts of bulking agent mixed in a ratio of 3 parts, 5 parts of white carbon, 5 parts of surfactant Tsurupol 800A, and 10 parts of water.
0.0 mm, knead well to make a paste, and make a paste with a diameter of 0.
After extruding through the 71 sieve holes and drying, the
Cut into 1 length to obtain 1 tablet. [Effect of the invention] The compound of the present invention represented by general formula (1) and its salt are:
Annual weeds that occur in rice fields, such as Japanese grasshopper, Japanese cypress, and Japanese cypress;
It exhibits excellent herbicidal effects at extremely low dosages over a wide range of perennial weeds, such as firefly and grasshopper, from the time of germination to the growing season. In addition, various weeds that are problematic in upland fields, such as Japanese knotweed, Japanese knotweed, whiteweed, chickweed, Japanese velvet weed, goldenrod, and morning glory. Including broad-leaved weeds such as Ona fir, perennial and annual Cyperaceae weeds such as Cyperus spp. It is possible to effectively control grass weeds such as barnyard grass, silver grass, foxtail grass, grasshopper, johnson grass, grasshopper, and wild oat. On the other hand, the herbicide of the present invention is highly safe for crops, especially rice,
Shows high safety against wheat, barley, soybeans, cotton, etc. Next, the effects of the compounds of the present invention will be explained by giving test examples.6 Test Example 1 (herbicidal effect test by paddy soil treatment)100
A cm' plastic pot was filled with paddy soil, and after raking for one generation, seeds of Japanese millet (Ec), Japanese snail (MO), and firefly (Sc) were sown, and the pots were flooded to a depth of 3C. The next day, the wettable powder prepared according to Formulation Example 1 was diluted with water and dropped onto the water surface. The application amount was 100 g of active ingredient per 10 ares. Thereafter, they were grown in a greenhouse, and on the 21st day of treatment, the herbicidal effect was investigated according to the standards in Table 3. The results are shown in Table 4. It is shown in Table 3, Table 4, and Table 5. Table 5 Table 4 continued Test example 2 (herbicidal effect test by field soil treatment) 120
cm'' Plastic pots were filled with field soil and 1 edible vinyl (Ec), Japanese knotweed (Po), and bluetail (Aho) were grown.
Seeds of , Shiroza (Ch), and Kogomegayari (CD) were sown and covered with soil. A wettable powder prepared according to Formulation Example 1 was diluted with water, and 10 ares were added so that the active ingredient was 100 g per 10 ares. LooQ was uniformly sprayed on the soil surface with a small sprayer.Then, it was grown in a greenhouse and the herbicidal effect was investigated according to the standards in Table 3, after the 21st day of treatment.The results are shown in Table 5. 3 (Herbicidal effect test by field soil stem and leaf treatment) 120
cm'' plastic pots were filled with field soil and planted with edible cottontail (Ec), Japanese knotweed (Po), and bluetail (AI).
, Shiroza (Ch), and Kogomegayari (Ci) seeds were sown, and after growing in a greenhouse for two weeks, a wettable powder prepared according to Formulation Example 1 was diluted with water, and the active ingredient was 1 per 10 ares.
A small sprayer was used to spray 100Q per 10 are over the entire plant body from above to the foliage so that the total weight was 0.00g. Then, grow it in a greenhouse. On day 14 of treatment, the herbicidal effect was investigated according to the criteria in Table 3. The results are shown in Table 6. Table 6 Continuation of Table 6 Test Example 4 (Medical efficacy/toxicity test in field soil treatment) 60
Fill each 0 cm" plastic pot with upland soil, and add soybean (G l >, cotton (Go), Japanese barnyard grass (Ec), Japanese knotweed (Po), blueberry (A), and white grass (Ch.
), sowing Ichibi (^b) and Noassagao (Ip),
After absorbing water from the bottom of 6 pots where tubers of Japanese perilla (Cr) were placed and covered with soil, a hydrating powder prepared according to Formulation Example 1 was added to the predetermined amount of active ingredient (25g/1.(!a)). , diluted with 1001 m of water per 10 are, and sprayed on the soil surface using a small sprayer. After treatment, the plants were grown again in the greenhouse. On the 20th day after treatment, the herbicidal effect and phytotoxicity were investigated according to the standards in Table 3. The results are shown in Table 7. Table 7 Patent Source: Kumiai Chemical Industry Co., Ltd. Ihara Chemical Industry Co., Ltd.
Claims (1)
置換されてもよいフェニル基を示し、Ｒ＾１は水素原子
、アルキル基、アルケニル基、ハロアルケニル基、シク
ロアルキル基、シクロアルケニル基、シクロアルキルア
ルキル基または任意に置換されてもよいフェニル基を示
し、Ｘ及びＹは同一または相異なり、アルキル基、アル
コキシ基、ハロアルコキシ基またはハロゲン原子を示す
。）にて表されるＮ−スルホニルアミド誘導体及びその
塩。 ▲数式、化学式、表等があります▼ （式中、Ｒはアルキル基、ハロアルキル基または任意に
置換されてもよいフェニル基を示し、Ｒ＾１は水素原子
、アルキル基、アルケニル基、ハロアルケニル基、シク
ロアルキル基、シクロアルケニル基、シクロアルキルア
ルキル基または任意に置換されてもよいフェニル基を示
し、Ｘ及びＹは同一または相異なり、アルキル基、アル
コキシ基、ハロアルコキシ基またはハロゲン原子を示す
。）にて表されるＮ−スルホニルアミド誘導体及びその
塩を有効成分として含有する除草剤。(1) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (In the formula, R represents an alkyl group, a haloalkyl group, or an optionally substituted phenyl group, and R^1 represents a hydrogen atom, an alkyl group, or an alkenyl group. group, haloalkenyl group, cycloalkyl group, cycloalkenyl group, cycloalkylalkyl group, or optionally substituted phenyl group, X and Y are the same or different, and alkyl group, alkoxy group, haloalkoxy group or N-sulfonylamide derivatives and salts thereof represented by (representing a halogen atom). ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, R represents an alkyl group, a haloalkyl group, or an optionally substituted phenyl group, and R^1 represents a hydrogen atom, an alkyl group, an alkenyl group, or a haloalkenyl group. , represents a cycloalkyl group, a cycloalkenyl group, a cycloalkylalkyl group, or an optionally substituted phenyl group, and X and Y are the same or different and represent an alkyl group, an alkoxy group, a haloalkoxy group, or a halogen atom. ) A herbicide containing an N-sulfonylamide derivative and its salt as an active ingredient.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16627190A JPH0454168A (en) | 1990-06-25 | 1990-06-25 | N-sulfonylamide derivative and herbicide therefrom |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16627190A JPH0454168A (en) | 1990-06-25 | 1990-06-25 | N-sulfonylamide derivative and herbicide therefrom |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0454168A true JPH0454168A (en) | 1992-02-21 |
Family
ID=15828290
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16627190A Pending JPH0454168A (en) | 1990-06-25 | 1990-06-25 | N-sulfonylamide derivative and herbicide therefrom |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0454168A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0514551A1 (en) * | 1990-11-30 | 1992-11-25 | Kumiai Chemical Industry Co., Ltd. | Alkanamide derivative, its salt, production thereof, and herbicide |
| WO2004072066A1 (en) * | 2003-02-11 | 2004-08-26 | Prosidion Limited | Tri(cyclo) substituted amide glucokinase activator compounds |
| JP2019519598A (en) * | 2016-04-18 | 2019-07-11 | アイエフエム セラピューティクス インコーポレイテッド | Compounds and compositions for treating conditions associated with NLRP activity |
-
1990
- 1990-06-25 JP JP16627190A patent/JPH0454168A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0514551A1 (en) * | 1990-11-30 | 1992-11-25 | Kumiai Chemical Industry Co., Ltd. | Alkanamide derivative, its salt, production thereof, and herbicide |
| WO2004072066A1 (en) * | 2003-02-11 | 2004-08-26 | Prosidion Limited | Tri(cyclo) substituted amide glucokinase activator compounds |
| JP2007524577A (en) * | 2003-02-11 | 2007-08-30 | プロシディオン・リミテッド | Tri (cyclo) substituted amide glucokinase activating compound |
| JP2019519598A (en) * | 2016-04-18 | 2019-07-11 | アイエフエム セラピューティクス インコーポレイテッド | Compounds and compositions for treating conditions associated with NLRP activity |
| US11447460B2 (en) | 2016-04-18 | 2022-09-20 | Novartis Ag | Compounds and compositions for treating conditions associated with NLRP activity |
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