JPS63238006A - Agent for controlling rice blast - Google Patents
Agent for controlling rice blastInfo
- Publication number
- JPS63238006A JPS63238006A JP7330087A JP7330087A JPS63238006A JP S63238006 A JPS63238006 A JP S63238006A JP 7330087 A JP7330087 A JP 7330087A JP 7330087 A JP7330087 A JP 7330087A JP S63238006 A JPS63238006 A JP S63238006A
- Authority
- JP
- Japan
- Prior art keywords
- group
- alkyl
- alkyl group
- hydrogen
- 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.)
- Pending
Links
- 235000007164 Oryza sativa Nutrition 0.000 title claims description 15
- 235000009566 rice Nutrition 0.000 title claims description 15
- 240000007594 Oryza sativa Species 0.000 title claims 2
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 44
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 26
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 18
- HFFXLYHRNRKAPM-UHFFFAOYSA-N 2,4,5-trichloro-n-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide Chemical compound O1C(C)=CC(NS(=O)(=O)C=2C(=CC(Cl)=C(Cl)C=2)Cl)=N1 HFFXLYHRNRKAPM-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 10
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 9
- 150000002367 halogens Chemical class 0.000 claims abstract description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims abstract description 3
- 229910052751 metal Inorganic materials 0.000 claims abstract description 3
- 239000002184 metal Substances 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 22
- 244000061456 Solanum tuberosum Species 0.000 claims description 14
- 235000002595 Solanum tuberosum Nutrition 0.000 claims description 14
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 239000004480 active ingredient Substances 0.000 claims description 11
- 239000000126 substance Substances 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 20
- 150000001875 compounds Chemical class 0.000 abstract description 18
- -1 alkoxycarbonylethoxy Chemical group 0.000 abstract description 8
- 239000002689 soil Substances 0.000 abstract description 7
- 241000196324 Embryophyta Species 0.000 abstract description 4
- 241001330975 Magnaporthe oryzae Species 0.000 abstract description 2
- 238000002156 mixing Methods 0.000 abstract description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 239000013078 crystal Substances 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 241000209094 Oryza Species 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 201000010099 disease Diseases 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
- 239000004615 ingredient Substances 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 239000008187 granular material Substances 0.000 description 5
- 229940124530 sulfonamide Drugs 0.000 description 5
- 150000003456 sulfonamides Chemical class 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- WHHIPMZEDGBUCC-UHFFFAOYSA-N probenazole Chemical compound C1=CC=C2C(OCC=C)=NS(=O)(=O)C2=C1 WHHIPMZEDGBUCC-UHFFFAOYSA-N 0.000 description 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 241000233866 Fungi Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 230000003902 lesion Effects 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 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 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- 230000000887 hydrating effect Effects 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 150000002545 isoxazoles Chemical class 0.000 description 2
- 125000000842 isoxazolyl group Chemical group 0.000 description 2
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 125000000565 sulfonamide group Chemical group 0.000 description 2
- JLKIGFTWXXRPMT-UHFFFAOYSA-N sulphamethoxazole Chemical compound O1C(C)=CC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 JLKIGFTWXXRPMT-UHFFFAOYSA-N 0.000 description 2
- COLOHWPRNRVWPI-UHFFFAOYSA-N 1,1,1-trifluoroethane Chemical compound [CH2]C(F)(F)F COLOHWPRNRVWPI-UHFFFAOYSA-N 0.000 description 1
- RHFWLPWDOYJEAL-UHFFFAOYSA-N 1,2-oxazol-3-amine Chemical compound NC=1C=CON=1 RHFWLPWDOYJEAL-UHFFFAOYSA-N 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- WVBFNSJUEUADMP-UHFFFAOYSA-N 4-acetyl-4-aminocyclohexa-1,5-diene-1-sulfonamide Chemical compound CC(=O)C1(N)CC=C(S(N)(=O)=O)C=C1 WVBFNSJUEUADMP-UHFFFAOYSA-N 0.000 description 1
- LNZJPSYNGYFWKE-UHFFFAOYSA-N 5-(trifluoromethyl)-1,2-oxazol-3-amine Chemical compound NC=1C=C(C(F)(F)F)ON=1 LNZJPSYNGYFWKE-UHFFFAOYSA-N 0.000 description 1
- GGXGVZJHUKEJHO-UHFFFAOYSA-N 5-tert-butyl-1,2-oxazol-3-amine Chemical compound CC(C)(C)C1=CC(N)=NO1 GGXGVZJHUKEJHO-UHFFFAOYSA-N 0.000 description 1
- LPEKGGXMPWTOCB-UHFFFAOYSA-N 8beta-(2,3-epoxy-2-methylbutyryloxy)-14-acetoxytithifolin Natural products COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 206010059866 Drug resistance Diseases 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 244000017020 Ipomoea batatas Species 0.000 description 1
- 235000002678 Ipomoea batatas Nutrition 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 240000008467 Oryza sativa Japonica Group Species 0.000 description 1
- 235000005043 Oryza sativa Japonica Group Nutrition 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- AXLOCHLTNQDFFS-BESJYZOMSA-N azastene Chemical class C([C@H]1[C@@H]2CC[C@@]([C@]2(CC[C@@H]1[C@@]1(C)C2)C)(O)C)C=C1C(C)(C)C1=C2C=NO1 AXLOCHLTNQDFFS-BESJYZOMSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 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
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 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
- 239000000969 carrier Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- WACQKHWOTAEEFS-UHFFFAOYSA-N cyclohexane;ethyl acetate Chemical compound CCOC(C)=O.C1CCCCC1 WACQKHWOTAEEFS-UHFFFAOYSA-N 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 description 1
- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000284 extract Substances 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
- 239000000706 filtrate Substances 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 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
- 239000010410 layer Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 229940057867 methyl lactate Drugs 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- JFCHSQDLLFJHOA-UHFFFAOYSA-N n,n-dimethylsulfamoyl chloride Chemical compound CN(C)S(Cl)(=O)=O JFCHSQDLLFJHOA-UHFFFAOYSA-N 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 229960005404 sulfamethoxazole Drugs 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
Abstract
Description
【発明の詳細な説明】 （産業上の利用分野） 本発明は、稲などのイモチ病の防除剤に関する。[Detailed description of the invention] (Industrial application field) TECHNICAL FIELD The present invention relates to a control agent for rice blast disease of rice and the like.
（従来の技術）
イネ科植物に多発するイモチ病は、不完全菌により発生
し、古くから稲作に多大な被害を与えている。このイモ
チ病に有効な薬剤として１種々の化合物が合成されてい
る。例えば１次に示すスルホンアミド骨格を有する化合
物やイソオキサゾール骨格を有する化合物が知られてい
る。(Prior Art) The rice blast disease, which frequently occurs in gramineous plants, is caused by Deuteromycosis fungi and has caused great damage to rice cultivation since ancient times. Various compounds have been synthesized as effective drugs for this rice blast disease. For example, compounds having a primary sulfonamide skeleton and compounds having an isoxazole skeleton are known.
（ａｌスルホンアミド骨格を有する化合物ｚ 特公昭４５−１４３０１号公報 （一般名プロベナゾール） （式中、Ｒはメチル基またはイソプロピル基を示す。） （式中 １１はアルキル基、シクロアルキル基。(Compound z having an al sulfonamide skeleton Special Publication No. 45-14301 (generic name Probenazole) (In the formula, R represents a methyl group or an isopropyl group.) (In the formula, 11 is an alkyl group or a cycloalkyl group.
？ １Ｊ −ル基マタハ水ｆｉ ： Ｒ”バーＣｏ−Ｒ
’ ？ Ｒ″ハアルキル基アルケニル基、シクロアルキ
ルなどを示す。）
ｚ
（式中 Ｒ１およびＲ２はそれぞれ独立して低級アルキ
ル基、シクロアルキル基、アルコキシアルキル基、アル
コキシカルボニルアルキル基、ベンジル基またはフェニ
ル基を示す。）
（ｂ）イソオキサゾール骨格を有する化合物（式中 Ｒ
１は水素または低級アルキル基；Ｒ２は水素、低級アル
キル基、フェニル基。? 1J-ru group Mataha water fi: R” bar Co-R
' ? R'' represents an alkenyl group, a cycloalkyl group, etc.) z (In the formula, R1 and R2 each independently represent a lower alkyl group, a cycloalkyl group, an alkoxyalkyl group, an alkoxycarbonylalkyl group, a benzyl group, or a phenyl group) ) (b) Compound having an isoxazole skeleton (in the formula R
1 is hydrogen or a lower alkyl group; R2 is hydrogen, a lower alkyl group, or a phenyl group.
低級アルコキシ基またはカルボニル基；Ｒ３はハロゲン
原子を含むアルキル基を示す。）
イモチ病を引き起こす菌の薬剤耐性などの点を考慮する
と、上記化合物の他にも効果的にイモチ病を防除しうる
イモチ防除剤の開発が望まれる。Lower alkoxy group or carbonyl group; R3 represents an alkyl group containing a halogen atom. ) Considering the drug resistance of the fungi that cause blast disease, it is desired to develop a blast control agent that can effectively control blast blast in addition to the above-mentioned compounds.
（発明の目的）
本発明の目的は、稲などのイモチ病を効果的に防除しう
るイモチ防除剤を提供することにある。(Objective of the Invention) An object of the present invention is to provide a rice blast control agent that can effectively control rice blast disease.
（発明の要旨）
本発明のイモチ防除剤は、下記一般式（Ｉ）で示される
スルホンアミド誘導体またはその塩を有効成分として含
有し、そのことにより上記目的が達成される：
Ｘ、Ｎ−５ｏ□Ｚ （Ｉ）（式中、 Ｘは
ｌ？ｉ
Ｒ’は水素、アルキル基、ヒドロキシメチル基。(Summary of the Invention) The potato blast control agent of the present invention contains a sulfonamide derivative represented by the following general formula (I) or a salt thereof as an active ingredient, thereby achieving the above object: X, N-5o □Z (I) (wherein, X is l?i R' is hydrogen, an alkyl group, or a hydroxymethyl group.
トリフルオロメチル基、シクロアルキル基。Trifluoromethyl group, cycloalkyl group.
ハロアルキル基、フェニル基、 −０Ｒ５または−ＧＯ
ＯＲ’ ； Ｒ２は水素、ハロゲン、アルキル基。haloalkyl group, phenyl group, -0R5 or -GO
OR'; R2 is hydrogen, halogen, or alkyl group.
−ＣＯＯＨまたは一０Ｒ５； Ｒ”はアルキル基、アル
コキシ基、アミノ基、アルコキシカルボニルエトキシ基
、 ＣＩＩｚ＝ＣＨＣＨｚＯ−＋ ＨＣ＝Ｃ（ＣＨ
ｚ）＋＋Ｏ−。-COOH or 10R5; R" is an alkyl group, an alkoxy group, an amino group, an alkoxycarbonylethoxy group, CIIz=CHCHzO-+ HC=C(CH
z) ++O-.
Ｘ ’ Ｃｌｌ ｚｃｔｌ ｚｏ−またはＣＦ３ＣＨ２
０−； ｎは１または２；Ｒ５およびＲ６はそれぞれ
水素またはアルキル基；Ｘｏはハロゲンまたはアルコキ
シ基；
ｙは水素、造塩金属またはアルキル基；Ｚは
アルキル基、アルコキシ基、ハロゲン、トリフルオロメ
チル基またはＮＲ’Ｒ” 、Ｒ？は水素またはアルキ
ル基、Ｒ１１は水素、アルキル基またはＣ０Ｒ９基、Ｒ
９はアルキル基、アルコキシ基。X' Cll zctl zo- or CF3CH2
0-; n is 1 or 2; R5 and R6 are each hydrogen or an alkyl group; group or NR'R'', R? is hydrogen or an alkyl group, R11 is hydrogen, an alkyl group or a C0R9 group, R
9 is an alkyl group or an alkoxy group.
トリフルオロメチル基、アルコキシカルボニル基または
−ＣＨ２１？Ｉ’ ；Ｒ”は水素またはアルコキシ基
をそれぞれ示す）。Trifluoromethyl group, alkoxycarbonyl group or -CH21? I';R'' represents hydrogen or an alkoxy group, respectively).
上記式Ｙの造塩金属としては、ナトリウム、カリウム、
アルミニウム、カルシウム、マグネシウム、リチウムな
どが挙げられる。この他、酸またはアミン類により塩が
形成されていてもよい。このような塩を形成する酸とし
ては塩酸、硝酸、硫酸などの鉱酸、酢酸、メタンスルホ
ン酸などの有機酸が挙げられ、アミン類としてはアンモ
ニア。The salt-forming metal of the above formula Y includes sodium, potassium,
Examples include aluminum, calcium, magnesium, and lithium. In addition, salts may be formed with acids or amines. Examples of acids that form such salts include mineral acids such as hydrochloric acid, nitric acid, and sulfuric acid, and organic acids such as acetic acid and methanesulfonic acid; examples of amines include ammonia.
ジメチルアミン、トリエチルアミン、エタノールアミン
、ジェタノールアミン、Ｎ、Ｎ−ジエチルエタノールア
ミン、シクロヘキシルアミンなどが挙げられる。Examples include dimethylamine, triethylamine, ethanolamine, jetanolamine, N,N-diethylethanolamine, and cyclohexylamine.
上記（Ｉ）弐で示される化合物は、さらに次の２種のタ
イプに分類される：
ａ）イソオキサゾールタイプ化合物：
（式中、Ｚはアルキル基。The compounds represented by (I) 2 above are further classified into the following two types: a) Isoxazole type compounds: (wherein, Z is an alkyl group.
を表し、 Ｒ’、 Ｒ”、 Ｙ、 Ｒ’は前記と同意義
を有する）。(R', R'', Y, R' have the same meanings as above).
ｂ）アシルタイプ化合物：
（式中 Ｒ３およびＹは前記と同意義を有し；Ｒ４は水
素、アルキル基、アルコキシ基、ハロゲン、トリフルオ
ロメチル基または−ＮＩ？’Ｒ’ 。b) Acyl type compound: (wherein R3 and Y have the same meanings as above; R4 is hydrogen, an alkyl group, an alkoxy group, a halogen, a trifluoromethyl group or -NI?'R'.
Ｒ７は水素またはアルキル基、Ｒ８は水素、アルキル基
またはＣ０Ｒ９基；Ｒ９はアルキル基またはアルコキシ
基をそれぞれ示す）。R7 represents hydrogen or an alkyl group; R8 represents hydrogen, an alkyl group, or a C0R9 group; R9 represents an alkyl group or an alkoxy group, respectively).
式（Ｉ）〜（ＩＩりにおけるアルキル基およびアルコキ
シ基は主として炭素数が１〜５の低級アルキル基および
低級アルコキシ基をそれぞれ示す。The alkyl group and alkoxy group in formulas (I) to (II) mainly represent a lower alkyl group and a lower alkoxy group having 1 to 5 carbon atoms, respectively.
これらスルホンアミド誘導体の合成法には既知の合成法
が適用され得、特に限定されない。例えば１次のように
合成される。Known synthetic methods can be applied to the method of synthesizing these sulfonamide derivatives, and there are no particular limitations. For example, they are synthesized in a first-order manner.
（Ｉ１イソオキサゾ一ルタイプ化合物（ＩＩ）の合成（
式中、Ｘ”はハロゲンを示しｌ Ｒ’ｌ Ｒ”ＩＹ、
Ｚは前記と同意義を有する。）
（２）カルボニルタイプ化合物（ＩＩＩ）の合成このよ
うなスルホンアミド誘導体のイソオキサゾールタイプ化
合物の例を表１に、アシルタイプ化合物の例を表２に示
す。表１および表２において、＊印は、新規化合物であ
ることを示す、ここで使用される略称は下記の意義を有
する。Ｍｅ （メチル”） 、 Ｅｔ （エチル） 、
Ｐｒ （プロピル） 、 Ｂｕ （ブチル） 、 Ａ
ｃ （アセチル）、Δ（シクロプロピル）。(I1 Synthesis of isoxazol type compound (II) (
In the formula, X" represents a halogen, l R'l R"IY,
Z has the same meaning as above. (2) Synthesis of carbonyl type compound (III) Examples of isoxazole type compounds of such sulfonamide derivatives are shown in Table 1, and examples of acyl type compounds are shown in Table 2. In Tables 1 and 2, the * mark indicates a new compound. The abbreviations used here have the following meanings. Me (methyl), Et (ethyl),
Pr (propyl), Bu (butyl), A
c (acetyl), Δ (cyclopropyl).
Ｃ，Ａ、 （ケミカル・アブストラクッ） 、 ＵＳＰ
（米国特許”） 、 ＤＤ （東独特許） 、 ＡＵ
（オーストラリア特許）。C, A, (Chemical Abstract), USP
(US patent), DD (East German patent), AU
(Australian patent).
ＣＩ （スイス特許） 、 ＢＰ （ヨーロッパ特許）
、 ＮＬ （オランダ特許） 、 ＰＲ（フランス特
許）（以下余白）
１、ｅＢｒ 、 ｃ、、、
Ｎ、。CI (Swiss patent), BP (European patent)
, NL (Dutch patent), PR (French patent) (the following margins) 1, eBr, c,,,
N.
上記表１および表２に示される化合物のうち。Among the compounds shown in Tables 1 and 2 above.
例えば次に示すタイプの化合物（ＩＩ）゛および（■）
゛は１次の各公報に記載された公知の化合物である。For example, the following types of compounds (II) and (■)
゛ is a known compound described in each of the following publications.
しかし、それらは、いずれもその用途が抗菌剤。However, all of them are used as antibacterial agents.
除草剤などに限られており、これらのタイプの化合物が
イモチ防除剤として有効なことは全く知られていない。They are limited to herbicides and the like, and it is completely unknown that these types of compounds are effective as blast control agents.
（以下余白）
本発明のイモチ防除剤は９式（Ｉ）のスルホン７ミド誘
導体の他に、必要に応じて各種賦形剤や容剤（固体担体
、液体担体）、各種添加剤（界面活性剤など）が含有さ
れる。固体担体としては。(Leaving space below) In addition to the sulfone 7-mide derivative of formula 9 (I), the blast control agent of the present invention may contain various excipients and containers (solid carrier, liquid carrier), various additives (surface-active agents, etc.). As a solid carrier.
タルク、クレー、カオリン、ケイ藻土、シリカなどが、
液体担体としては、水、メタノール、エタノール、アセ
トン、ジメチルホルムアミド、エーテルなどが挙げられ
る。添加剤としては、非イオン界面活性剤（例えば、ポ
リオキシエチレンアルキルフェニルエーテル、ポリオキ
シエチレン脂肪酸エステル）、陰イオン界面活性剤（例
えば、アルキルベンゼンスルホン酸塩、リグニンスルホ
ン酸塩、ジナフチルメタンスルホン酸塩）、ポリビニル
アルコール、カルボキシメチルセルロース。Talc, clay, kaolin, diatomaceous earth, silica, etc.
Liquid carriers include water, methanol, ethanol, acetone, dimethylformamide, ether, and the like. Additives include nonionic surfactants (e.g., polyoxyethylene alkylphenyl ether, polyoxyethylene fatty acid ester), anionic surfactants (e.g., alkylbenzenesulfonates, ligninsulfonates, dinaphthylmethanesulfonic acid). salt), polyvinyl alcohol, carboxymethylcellulose.
アラビアゴムなどが挙げられる。製剤形態としては、粉
剤２粒剤、微粒剤、水和剤、乳剤などがあり、常法によ
り製造される。製剤には、上記有効成分であるスルホン
アミド誘導体が０．１重量％以上、好ましくは２〜８０
重量％の割合で含有される。Examples include gum arabic. Preparation forms include two powders, fine granules, wettable powders, emulsions, etc., and are manufactured by conventional methods. The formulation contains 0.1% by weight or more of the sulfonamide derivative as the above active ingredient, preferably 2 to 80% by weight.
It is contained in a proportion of % by weight.
上記有効成分を含む各種製剤の処方を次に示す。The formulations of various preparations containing the above active ingredients are shown below.
裂」■汁上
（粉剤）
成 分 重量部上記
各成分を粉砕混合して粉剤とする。■Juice (powder) Ingredients Parts by weight Grind and mix the above ingredients to make a powder.
１剋班１
（粒剤）
成 分 重量部上記
各成分を混合粉砕し、水を加えて造粒し。1 batch 1 (granules) Ingredients Parts by weight The above ingredients are mixed and ground, and water is added to make granules.
乾燥する。dry.
（以下余白）
ｌｊ生例ユ
（乳剤）
成 分 重量部スルホン
アミド誘導体 ２５ポリオキシエチ
レンアルキルフヱニルエーテル上記各成分を混合し、乳
剤原液とする。(The following is a blank space) lj Raw example (emulsion) Ingredients Parts by weight Sulfonamide derivative 25 Polyoxyethylene alkyl phenyl ether The above components are mixed to form an emulsion stock solution.
１剋炭↓
（水和剤）
成 分 重量部上記各製
剤は、そのままで、あるいは水で希釈するなどして１通
常のイモチ防除剤と同様に使用される。他の殺菌剤、殺
虫剤、殺線虫剤９種子消毒剤、除草剤、肥料、土壌改良
剤などと混合して用いられてもよい。本発明のイモチ防
除剤は２例えば、育苗箱、水田、乾田などの水面あるい
は土壌表面に散布する方法、植物の根部を該防除剤溶液
に浸漬する方法、土壌に混合する方法などにより使用さ
れる。使用量は、イモチ病発生の程度。1. Charcoal↓ (hydrating powder) Ingredients Parts by weight Each of the above preparations is used as is or diluted with water in the same manner as a normal Japanese rice blast control agent. It may be used in combination with other fungicides, insecticides, nematicides, seed disinfectants, herbicides, fertilizers, soil conditioners, etc. The rice blast control agent of the present invention can be used by two methods, for example, by spraying it on the water surface or soil surface of seedling boxes, paddy fields, dry fields, etc., by immersing the roots of plants in the control agent solution, or by mixing it into soil. . The amount used depends on the degree of occurrence of rice blast disease.
製剤の形態、使用の時期、使用方法などにより異なる。It varies depending on the form of the preparation, timing of use, method of use, etc.
例えば、固形製剤（粒剤、有効成分１〜２０重量％）を
水田の水面または土壌表面に施用する場合には、１０ア
ールあたり２〜１０ｋｇの割合で使用される。この固形
製剤を育苗箱（３０ｃｆ１１×６０ｃＩ１１×３−；使
用土約５β）に施用する場合には、１箱あたり１０〜５
０ｇの割合で苗の上から均一に散布するのが好ましい。For example, when applying a solid preparation (granules, active ingredient 1 to 20% by weight) to the water surface or soil surface of a paddy field, it is used at a rate of 2 to 10 kg per 10 ares. When applying this solid preparation to seedling boxes (30cf11 x 60cI11 x 3-; soil used about 5β), 10 to 5
It is preferable to spray it evenly over the seedlings at a rate of 0g.
液剤（有効成分１０〜８０重量％）は。Liquid preparation (active ingredient 10-80% by weight).
１０アールあたり５０〜５００ｊｉ！ （Ｉ０〜１０１
０００ｐｐの割合で散布される。50-500 ji per 10 are! (I0~101
Sprayed at a rate of 000pp.
（作用）
このように、特定の構造式を有するスルホンアミド誘導
体を有効成分とするこれまでに知られていないタイプの
イモチ防除剤が提供される。このイモチ防除剤は、後述
の実施例に示されるように。(Function) In this way, a hitherto unknown type of blast control agent containing a sulfonamide derivative having a specific structural formula as an active ingredient is provided. This sweet potato control agent is used as shown in the Examples below.
例えば、既知イモチ防除剤であるプロベナゾール（−船
名）とほぼ同等の活性を有する。安全性についても１通
常の使用量の範囲であれば、生体に対する毒性や蓄積性
は認められず、従来のイモチ防除剤と同様に使用され得
る。For example, it has almost the same activity as Probenazole (-ship name), a known potato blast control agent. As for safety, 1. If the amount used is within the normal range, no toxicity or accumulation to living organisms is observed, and the product can be used in the same manner as conventional potato blast control agents.
（実施例） 以下に本発明を実施例につき説明する。(Example) The invention will be explained below with reference to examples.
尖隻■上
〔各種スルホンアミド誘導体の合成〕
（Ａ）イソオキサゾールタイプ化合物の合成チルスルフ
ァニルアミ゛イソオキサゾールのム３−アミノ−５−ト
リフルオロメチルイソオキサゾール３．５０ｇ （０，
０２３０モル）とＮ−アセチルスルファニルクロライド
６．４５ｇ （０，０２７６モル）とを乾燥ピリジン２
３＋ｄに溶解し、室温で１日放置した。3-Amino-5-trifluoromethylisoxazole 3.50 g (0,
0230 mol) and 6.45 g (0,0276 mol) of N-acetylsulfanyl chloride in dry pyridine 2
3+d and left at room temperature for 1 day.
こ９反応液に水を加え、１０％塩酸水溶液でｐ１１２に
調整し、析出した結晶を濾取し、水洗した。これを減圧
乾燥し、酢酸エチルによる再結晶を繰り返した。融点１
９３〜１９４℃の無色板状結晶２．ＯＯｇ （収率２４
．９％）が得られた。再結晶の母液を減圧濃縮し、 ４
．８４ｇ （６０，３％）の結晶を得た。この結晶はそ
のまま次工程に使用した。 、
ニルアミドイソオキサゾールのＡ
（Ａ）−１項で得られた５−トリフルオロメチル−３−
ｐ−アセチルスルファニルアミドイソオキサゾール５．
３４ｇ （０，０１５３モル）に５％Ｎａ１ｌ水溶液６
１．２０ｇ （０，０７６５モル）を加え、１００℃で
１．５時間攪拌した。反応液を冷却後、濃塩酸を加えて
ｐＨ５，２に調整し、析出結晶を濾取、水洗、減圧乾燥
した。Water was added to this 9 reaction solution, the pH was adjusted to 112 with 10% aqueous hydrochloric acid solution, and the precipitated crystals were collected by filtration and washed with water. This was dried under reduced pressure, and recrystallization from ethyl acetate was repeated. Melting point 1
Colorless plate-like crystals at 93-194°C 2. OOg (yield 24
．． 9%) was obtained. Concentrate the recrystallization mother liquor under reduced pressure, 4
．． 84 g (60.3%) of crystals were obtained. This crystal was used as it was in the next step. , A of nylamide isoxazole (A) 5-trifluoromethyl-3- obtained in section-1
p-acetylsulfanilamide isoxazole5.
34g (0,0153mol) of 5% Na1l aqueous solution 6
1.20 g (0,0765 mol) was added and stirred at 100° C. for 1.5 hours. After cooling the reaction solution, concentrated hydrochloric acid was added to adjust the pH to 5.2, and the precipitated crystals were collected by filtration, washed with water, and dried under reduced pressure.
濾液と洗液は合わせて酢酸エチルで抽出した。得られた
結晶および酢酸エチル抽出液をそれぞれシリカゲルによ
るクロマトグラフィーに付して精製し、 ２．５５ｇ
（収率５４．３％）の結晶を得た。この結晶を酢酸エチ
ルを用いて再結晶し、融点１８５〜１８６℃の無色プリ
ズム状結晶を得た。再結晶の母液についても濃縮して再
結晶を繰り返し９合計２．３３ｇ（収率４９．６％）の
精製結晶を得た。The filtrate and washings were combined and extracted with ethyl acetate. The obtained crystals and ethyl acetate extract were each purified by chromatography on silica gel, and 2.55 g
(yield 54.3%) crystals were obtained. These crystals were recrystallized using ethyl acetate to obtain colorless prismatic crystals with a melting point of 185-186°C. The recrystallization mother liquor was also concentrated and recrystallization was repeated to obtain a total of 2.33 g (yield: 49.6%) of purified crystals.
サシミル メ ンスルホンアミドの人
３−アミノ−５ｔｅｒｔ−ブチルイソオキサゾール２１
．０３ｇ （０，１５０モル）を乾燥ピリジン６０ｗ１
に溶解し、塩化メタンスルホニル１８．９０ｇ （０，
１６５モル）を水冷下にて滴下した。水冷下で４５分間
。Sasimil mensulfonamide person 3-amino-5tert-butyl isoxazole 21
．． 03g (0,150 mol) of dry pyridine 60w1
18.90 g of methanesulfonyl chloride (0,
165 mol) was added dropwise under water cooling. 45 minutes under water cooling.
室温で１時間撹拌後、室温で１夜放置した。反応液に水
を添加し、濃塩酸でｐＨ１に調整し、塩化メチレンで抽
出した。有機層を水洗し、乾燥し、減圧濃縮した。得ら
れた結晶をｎ−ヘキサン−ベンゼンより再結晶し、融点
１１８．５〜１２０．０℃の微褐色鱗片状結晶２４．６
１ｇ （収率７５．２％）を得た。再結晶の母液はシリ
カゲルによるクロマトグラフィーに付して精製し、再結
晶して融点１１８．５〜Ｌ１９．５℃の無色結晶５．１
３ｇ （収率１５．７％）を得た。After stirring at room temperature for 1 hour, the mixture was left at room temperature overnight. Water was added to the reaction solution, the pH was adjusted to 1 with concentrated hydrochloric acid, and the mixture was extracted with methylene chloride. The organic layer was washed with water, dried, and concentrated under reduced pressure. The obtained crystals were recrystallized from n-hexane-benzene to give slightly brown scaly crystals with a melting point of 118.5 to 120.0°C.
1 g (yield 75.2%) was obtained. The recrystallized mother liquor was purified by chromatography on silica gel and recrystallized to give colorless crystals with a melting point of 118.5 to 19.5°C.
3 g (yield 15.7%) was obtained.
（以下余白）
Ｈ３
５−ｔｅｒｔ−ブチル−３−Ｎ−メチルアミノイソオキ
サゾール２．００ｇ （’０．０１３モル）を乾燥ピリ
ジン３．００ｇ （０，０３８モル）に溶解し、塩化メ
タンスルホニル１．４９ｇ （０，０１３モル）を滴下
し、室温で５時間攪拌した。反応液に５％塩酸水溶液を
加え。(Left below) H3 2.00 g (0.013 mol) of 5-tert-butyl-3-N-methylaminoisoxazole was dissolved in 3.00 g (0,038 mol) of dry pyridine, and 1.0 g (0.038 mol) of methanesulfonyl chloride was dissolved. 49 g (0,013 mol) was added dropwise and stirred at room temperature for 5 hours. Add 5% aqueous hydrochloric acid solution to the reaction solution.
エーテルで抽出し、有機層を無水芒硝で乾燥し。Extract with ether and dry the organic layer with anhydrous sodium sulfate.
減圧濃縮した。これをｎ−ヘキサン−ベンゼンより再結
晶し、融点５１．５〜５３．０℃の淡黄色鱗片状結晶０
．５６ｇ （収率１８．５％）を得た。It was concentrated under reduced pressure. This was recrystallized from n-hexane-benzene to produce pale yellow scaly crystals with a melting point of 51.5-53.0°C.
．． 56 g (yield 18.5%) was obtained.
（Ａ）−５ソジウムＮ−（５−ｔｅｒｔ−ブチル−３−
イソオキサソ゛鵞ル）メ ンスルホンアミドの人Ｎ
（５−ｔｅｒｔ−ブチル−３−イソオキサシリル）メタ
ンスルホンアミド１５．４０ ｇ （０，０７０６モル
）をメタノール１０５顎に溶解し、２８％ナトリウムメ
チラートメタノール溶液１３．３１ ｇ （０，０６９
０モル）を加え、室温で５分間攪拌した。反応液を減圧
濃縮し、・アセトン７０ｄを加えて室温攪拌後、結晶を
濾取、アセトンで洗浄して無色の目的物結晶１６．８６
ｇ（収率９９．５％）を得た。融点２７０℃以上。(A)-5 Sodium N-(5-tert-butyl-3-
Mensulfonamide person N
15.40 g (0,0706 mol) of (5-tert-butyl-3-isoxacylyl)methanesulfonamide are dissolved in 105 liters of methanol and 13.31 g (0,069 mol) of 28% sodium methylate in methanol are dissolved.
0 mol) was added thereto, and the mixture was stirred at room temperature for 5 minutes. The reaction solution was concentrated under reduced pressure, and after adding 70 d of acetone and stirring at room temperature, the crystals were collected by filtration and washed with acetone to give 16.86 g of colorless target crystals.
g (yield 99.5%) was obtained. Melting point: 270℃ or higher.
（以下余白）
３−アミノイソオキサゾール４．２０ｇ （０，０５０
モル）を乾燥ピリジン１０−に溶解し、ジメチルスルフ
ァモイルクロライド７．９０ｇ （０，０５５モル）を
加え、 ６０℃で１時間攪拌した。冷却後、氷水を加え
。(Left below) 3-aminoisoxazole 4.20g (0,050
mol) was dissolved in dry pyridine 10-, 7.90 g (0,055 mol) of dimethylsulfamoyl chloride was added, and the mixture was stirred at 60°C for 1 hour. After cooling, add ice water.
濃塩酸を加えてｐＨ２に調整し、塩化メチレンで抽出し
た。有機層を水洗し、無水芒硝で乾燥し、残渣をシリカ
ゲルクロマトグラフィーに付して精製し、目的物質の結
晶６．１９ｇ （６４，２％）を得た。これを酢酸エチ
ル−シクロヘキサンより再結晶し。The pH was adjusted to 2 by adding concentrated hydrochloric acid, and the mixture was extracted with methylene chloride. The organic layer was washed with water, dried over anhydrous sodium sulfate, and the residue was purified by silica gel chromatography to obtain 6.19 g (64.2%) of crystals of the desired substance. This was recrystallized from ethyl acetate-cyclohexane.
融点９５〜９６℃の無色針状結晶５．１０ｇ （収率５
３．３％）を得た。5.10 g of colorless needle crystals with a melting point of 95-96°C (yield: 5
3.3%).
（Ｂ）スルホンアミド誘導体くアシルタイプ化合物）の
合成
１−メトキシカルボニルエチル−１−イル−−ＣＨ３
ＣＨ３
ＣＨ３−Ｃ６Ｈ４−３ｏ□ＮｌＩＣ０ＯＣＨＣＯＯＣＩ
Ｉ３ｐ−メチルベンゼンスルホニルイソシアナート０．
９９ｇ （０，００５モル）を乾燥塩化メチレン１０−
に溶解し、乳酸メチル０．５７ｇ （０，００５５モル
）を水冷下にて滴下した。水冷下で５分、室温で４時間
攪拌後１反応液を５％炭酸ナトリウム水溶液と振盪した
。炭酸ナトリウム水溶液層に濃塩酸を加え。(B) Synthesis of sulfonamide derivative acyl type compound) 1-methoxycarbonylethyl-1-yl--CH3 CH3 CH3-C6H4-3o□NlIC0OCHCOOCI
I3p-methylbenzenesulfonyl isocyanate 0.
99 g (0,005 mol) of dry methylene chloride 10-
0.57 g (0,0055 mol) of methyl lactate was added dropwise under water cooling. After stirring for 5 minutes under water cooling and 4 hours at room temperature, one reaction solution was shaken with a 5% aqueous sodium carbonate solution. Add concentrated hydrochloric acid to the sodium carbonate aqueous solution layer.
ｐＨ１に調整し、塩化メチレンで抽出した。有機層を無
水芒硝で乾燥し、：＄ｊ、圧留去し、残渣をシリカゲル
にてクロマトグラフィーに付し精製して淡黄色粘稠液体
１．２２ｇ （８０，８％）を得た。ｎ ｉ ０・５１
．５２５０災見尉ｌ
〔スルホンアミド誘導体塩の調製〕
Ｎ−（５−ｔｅｒｔ−ブチル−３−イソオキサシリル）
メタンスルホンアミド０．８７３ｇ （４，０ミリモル
）にｎ−プロピルアミン０．７１ｇ （Ｉ２，０ミリ
モル）を室温で添加し、１５分間加熱還流を行った後、
室温で一夜放置した。過剰のｎ−プロピルアミンを減圧
留去し、無色結晶１．１１ｇ （収率１００．０％）を
得た。この結晶をベンゼンで再結晶し、融点１０５．５
〜１０９．０℃の無色針状結晶０．６５ｇ （収率５８
．６％）を得た。The pH was adjusted to 1 and extracted with methylene chloride. The organic layer was dried over anhydrous sodium sulfate, evaporated under pressure, and the residue was purified by chromatography on silica gel to obtain 1.22 g (80.8%) of a pale yellow viscous liquid. n i 0・51
．． 5250 Osamijol [Preparation of sulfonamide derivative salt] N-(5-tert-butyl-3-isoxasilyl)
0.71 g (I2.0 mmol) of n-propylamine was added to 0.873 g (4.0 mmol) of methanesulfonamide at room temperature, and after heating under reflux for 15 minutes,
It was left at room temperature overnight. Excess n-propylamine was distilled off under reduced pressure to obtain 1.11 g (yield: 100.0%) of colorless crystals. This crystal was recrystallized with benzene, and the melting point was 105.5.
~109.0°C colorless needle crystals 0.65g (yield 58
．． 6%).
上記方法および実施例１ （Ａ）−４の方法に準じて。According to the above method and the method of Example 1 (A)-4.
各種スルホンアミド誘導体の塩を得た。各化合物（塩）
と、その融点を表３に示す。Salts of various sulfonamide derivatives were obtained. Each compound (salt)
and its melting point are shown in Table 3.
、、 ４Ｊ
−囲ゾ
ス１１１１
各種スルホンアミド誘導体を含む本発明のイモチ防除剤
を用いたイモチ防除試験を行った。表４〜６に示すスル
ホンアミド誘導体（実施例１で合成した化合物を含む）
を３２頁の方法により水和剤に調製した。この水和剤を
用い、下記の方法によりイモチ防除試験を行った。その
結果を表４〜６に示す。,, 4J
- Izos 1111 A rice blast control test was conducted using the potato blast control agent of the present invention containing various sulfonamide derivatives. Sulfonamide derivatives shown in Tables 4 to 6 (including the compound synthesized in Example 1)
was prepared into a wettable powder according to the method on page 32. Using this hydrating powder, a potato blast control test was conducted according to the method described below. The results are shown in Tables 4-6.
イモチ防除試験法：温室内で２葉期に生育させたイネの
幼苗に、イモチ防除剤をその有効成分が、ポット（３０
０ｍ）当り１．７■（Ｉ０ｐｐ＋ｎ濃度）となるように
水面施用する。１週間後にイモチ病菌（」■旦魁肛植肛
Ｕ並）胞子懸濁をイネ葉面に噴霧接種し、温度２８℃、
湿度９８％の接種室に２４時間保つ、その後５２８℃、
湿度９０％の温室に１週間置いて発病病斑数を調べ、防
除率（％）を下記式により算出する・。別に、必要に応
じて有効成分量を０．３４■（２ｐｐａ＋）および１７
■（Ｉ００ｐｐａ＋）として同様の試験を行う。Potato rootlet control test method: Rice seedlings grown at the two-leaf stage in a greenhouse were treated with a poter (30
Apply to the water surface so that the concentration is 1.7 (I0pp+n concentration) per 0m). One week later, a suspension of spores of the rice blast fungus (``■Dankai-an-an-U'') was spray-inoculated on the rice leaf surface, and the temperature was set at 28°C.
Keep in an inoculation room with a humidity of 98% for 24 hours, then 528°C.
Leave it in a greenhouse with 90% humidity for one week, check the number of diseased lesions, and calculate the control rate (%) using the formula below. Separately, if necessary, adjust the amount of active ingredients to 0.34■ (2ppa+) and 17
A similar test is conducted as (I00ppa+).
防除率（％）＝
防除率（％）を下記のように６段階に分けて評価し、こ
れを防除指数とする。Control rate (%) = Control rate (%) is evaluated in six stages as shown below, and this is used as a control index.
防除率（％） 防除指数
９９〜９５９７
９４〜８５９０
８４〜６５７０
６４〜４５５０
４４〜００
（以下余白）
表６
Ｒ”Ｃ０ＮＨＳＯ□Ｃ６Ｈ＃−Ｒ’ （ｐ）圃場水田の
１区画内に径４９（至）のポットをうめ込み、これに４
株の水稲苗（品種コシヒカリ）を定植した。出穂１３日
前に所定量の薬剤を水面施用した。薬剤としては、水で
希釈して４５．１■／ １００ｃｃとしたスルファメト
キサゾールナトリウム（シノミン（商品名）のナトリウ
ム塩）および粒剤のプロベナゾール（−船名）を用い、
いずれも２４０ ｇ ／１０ａとなるように使用した。Control rate (%) Control index 99-9597 94-8590 84-6570 64-4550 44-00 (Left below) Table 6 R”C0NHSO□C6H#-R' (p) Diameter 49 ( ) and fill it with 4
Paddy rice seedlings (variety Koshihikari) were planted. A predetermined amount of the chemical was applied to the water surface 13 days before heading. As drugs, sulfamethoxazole sodium (sodium salt of Shinomin (trade name)) diluted with water to a volume of 45.1 cm/100 cc and granules of probenazole (-ship name) were used.
Both were used at a weight of 240 g/10a.
処理直後、各ポットにイモチ病菌の接種源としてイモチ
病感染葉を散布し、感染させた。薬剤処理３１日目に株
あたりの病斑数を調べ２次に、薬剤処理後４９日目に株
あたりの穂首病斑数を調べた。防除価は下記の式で算出
し５その結果を表６に示す。Immediately after the treatment, each pot was infected by spraying leaves infected with the potato blast fungus as an inoculum. The number of lesions per plant was examined on the 31st day of drug treatment, and then the number of lesions on the ear neck was examined on the 49th day after drug treatment. The control value was calculated using the following formula5 and the results are shown in Table 6.
防除価（％）
（以下余白）
表６から、スルファメトキサゾールを有効成分とする本
発明のイモチ防除剤は、圃場試験において市販のイモチ
防除剤であるプロベナゾールとほぼ同等の効果を有する
ことが明らかである。Control value (%) (blank below) From Table 6, it can be seen that the potato blast control agent of the present invention containing sulfamethoxazole as an active ingredient has almost the same effect as Probenazole, a commercially available potato blast control agent, in field tests. is clear.
（発明の効果）
本発明によれば、新規化合物を含む特定のタイプのスル
ホンアミド誘導体を有効成分とするイモチ防除剤が提供
される。このイモチ防除剤は、従来の防除剤とほぼ同等
の効果を示し、安全性においても問題は認められない。(Effects of the Invention) According to the present invention, there is provided a potato blast control agent containing a specific type of sulfonamide derivative including a novel compound as an active ingredient. This potato blast control agent exhibits almost the same effect as conventional control agents, and no safety problems are observed.
有効成分のスルホンアミド誘導体の製造方法も容易であ
り、汎用の化合物を用いて合成されるため、イモチ防除
剤が安価に提供される。The method for producing the sulfonamide derivative, which is an active ingredient, is also easy and can be synthesized using a general-purpose compound, so the potato blast control agent can be provided at a low cost.
以上that's all
Claims (1)
体またはその塩を有効成分として含有するイモチ防除剤
： ▲数式、化学式、表等があります▼（ I ） （式中、Ｘは ▲数式、化学式、表等があります▼またはＲ＾３ＣＯ−
； Ｒ＾１は水素、アルキル基、ヒドロキシメチル基、トリ
フルオロメチル基、シクロアルキル基、ハロアルキル基
、フェニル基、−ＯＲ＾５または−ＣＯＯＲ＾６；Ｒ＾
２は水素、ハロゲン、アルキル基、−ＣＯＯＨまたは−
ＯＲ＾５；Ｒ＾３はアルキル基、アルコキシ基、アミノ
基、アルコキシカルボニルエトキシ基、ＣＨ＿２＝ＣＨ
ＣＨ＿２Ｏ−、ＨＣ≡Ｃ（ＣＨ＿２）＿ｎＯ−、Ｘ′Ｃ
Ｈ＿２ＣＨ＿２Ｏ−またはＣＦ＿３ＣＨ＿２Ｏ−；ｎは
１または２；Ｒ＾５およびＲ＾６はそれぞれ水素または
アルキル基；Ｘ′はハロゲンまたはアルコキシ基； Ｙは水素、造塩金属またはアルキル基； Ｚは ▲数式、化学式、表等があります▼またはアルキル基；
Ｒ＾４は水素、 アルキル基、アルコキシ基、ハロゲン、トリフルオロメ
チル基またはＮＲ＾７Ｒ＾８；Ｒ＾７は水素またはアル
キル基；Ｒ＾８は水素、アルキル基またはＣＯＲ＾９基
；Ｒ＾９はアルキル基、アルコキシ基、トリフルオロメ
チル基、アルコキシカルボニル基または−ＣＨ＿２Ｒ＾
１＾０；Ｒ＾１＾０は水素またはアルコキシ基をそれぞ
れ示す）。 ２、前記スルホンアミド誘導体が下記一般式（II）で示
される、特許請求の範囲第１項に記載のイモチ防除剤： ▲数式、化学式、表等があります▼（II） （式中、Ｚはアルキル基、 ▲数式、化学式、表等があります▼または▲数式、化学
式、表等があります▼ を示し、Ｒ＾１、Ｒ＾２、Ｙ、Ｒ＾９は前記と同意義を
有する）。 ３、前記スルホンアミド誘導体が下記一般式（III）で
示される、特許請求の範囲第１項に記載のイモチ防除剤
： ▲数式、化学式、表等があります▼（III） （式中、Ｒ＾３およびＹは前記と同意義を有し；Ｒ＾４
は水素、アルキル基、アルコキシ基、ハロゲン、トリフ
ルオロメチル基または−ＮＲ＾７Ｒ＾８；Ｒ＾７は水素
またはアルキル基；Ｒ＾８は水素、アルキル基またはＣ
ＯＲ＾９基；Ｒ＾９は、アルキル基またはアルコキシ基
をそれぞれ示す）。[Scope of Claims] 1. A rice blast control agent containing a sulfonamide derivative or its salt represented by the following general formula (I) as an active ingredient: ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) (wherein, X is ▲There is a mathematical formula, chemical formula, table, etc.▼ or R^3CO-
; R^1 is hydrogen, an alkyl group, a hydroxymethyl group, a trifluoromethyl group, a cycloalkyl group, a haloalkyl group, a phenyl group, -OR^5 or -COOR^6; R^
2 is hydrogen, halogen, alkyl group, -COOH or -
OR^5; R^3 is an alkyl group, alkoxy group, amino group, alkoxycarbonylethoxy group, CH_2=CH
CH_2O-, HC≡C(CH_2)_nO-, X'C
H_2CH_2O- or CF_3CH_2O-; n is 1 or 2; R^5 and R^6 are each hydrogen or an alkyl group; X' is a halogen or alkoxy group; Y is hydrogen, a salt-forming metal, or an alkyl group; There are chemical formulas, tables, etc. ▼ or alkyl groups;
R^4 is hydrogen, alkyl group, alkoxy group, halogen, trifluoromethyl group, or NR^7R^8; R^7 is hydrogen or alkyl group; R^8 is hydrogen, alkyl group, or COR^9 group; R^ 9 is an alkyl group, an alkoxy group, a trifluoromethyl group, an alkoxycarbonyl group or -CH_2R^
1^0; R^1^0 represents hydrogen or an alkoxy group, respectively). 2. The potato blast control agent according to claim 1, wherein the sulfonamide derivative is represented by the following general formula (II): ▲There are mathematical formulas, chemical formulas, tables, etc.▼(II) (In the formula, Z is Indicates an alkyl group, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ or ▲There are mathematical formulas, chemical formulas, tables, etc.▼, and R^1, R^2, Y, and R^9 have the same meanings as above). 3. The potato blast control agent according to claim 1, wherein the sulfonamide derivative is represented by the following general formula (III): ▲There are mathematical formulas, chemical formulas, tables, etc.▼(III) (In the formula, R^ 3 and Y have the same meanings as above; R^4
is hydrogen, alkyl group, alkoxy group, halogen, trifluoromethyl group or -NR^7R^8; R^7 is hydrogen or alkyl group; R^8 is hydrogen, alkyl group or C
OR^9 group; R^9 represents an alkyl group or an alkoxy group, respectively).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7330087A JPS63238006A (en) | 1987-03-26 | 1987-03-26 | Agent for controlling rice blast |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7330087A JPS63238006A (en) | 1987-03-26 | 1987-03-26 | Agent for controlling rice blast |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS63238006A true JPS63238006A (en) | 1988-10-04 |
Family
ID=13514174
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7330087A Pending JPS63238006A (en) | 1987-03-26 | 1987-03-26 | Agent for controlling rice blast |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63238006A (en) |
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|---|---|---|---|---|
| WO1997011942A1 (en) * | 1995-09-26 | 1997-04-03 | Shionogi & Co., Ltd. | Novel sulfonamide compounds and medicinal composition |
| US6030991A (en) * | 1993-05-20 | 2000-02-29 | Texas Biotechnology Corp. | Benzenesulfonamides and the use thereof to modulate the activity of endothelin |
| JP2001026506A (en) * | 1999-04-28 | 2001-01-30 | Takeda Chem Ind Ltd | Sulfonamide derivative |
| US6248767B1 (en) | 1997-04-28 | 2001-06-19 | Texas Biotechnology Corp. | Formulation of sulfonamides for treatment of endothelin-mediated disorders |
| US6331637B1 (en) | 1993-10-21 | 2001-12-18 | Texas Biotechnology Corporation | N-Alkyl, N-Alkenyl, N-Alkynyl, N-Aryl and N-fused bicyclo or tricyclo thienyl-, furyl-,and Pyrrolyl-sulfonamides and derivatives thereof that modulate the activity of endothelin |
| US6376523B1 (en) | 1994-05-20 | 2002-04-23 | Texas Biotechnology Corporation | Benzenesulfonamides and the use thereof to modulate the activity of endothelin |
| US6541498B2 (en) | 1993-05-20 | 2003-04-01 | Texas Biotechnology | Benzenesulfonamides and the use thereof to modulate the activity of endothelin |
| US6586617B1 (en) | 1999-04-28 | 2003-07-01 | Sumitomo Chemical Takeda Agro Company, Limited | Sulfonamide derivatives |
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|---|---|---|---|---|
| US6030991A (en) * | 1993-05-20 | 2000-02-29 | Texas Biotechnology Corp. | Benzenesulfonamides and the use thereof to modulate the activity of endothelin |
| US6541498B2 (en) | 1993-05-20 | 2003-04-01 | Texas Biotechnology | Benzenesulfonamides and the use thereof to modulate the activity of endothelin |
| US6331637B1 (en) | 1993-10-21 | 2001-12-18 | Texas Biotechnology Corporation | N-Alkyl, N-Alkenyl, N-Alkynyl, N-Aryl and N-fused bicyclo or tricyclo thienyl-, furyl-,and Pyrrolyl-sulfonamides and derivatives thereof that modulate the activity of endothelin |
| US6376523B1 (en) | 1994-05-20 | 2002-04-23 | Texas Biotechnology Corporation | Benzenesulfonamides and the use thereof to modulate the activity of endothelin |
| WO1997011942A1 (en) * | 1995-09-26 | 1997-04-03 | Shionogi & Co., Ltd. | Novel sulfonamide compounds and medicinal composition |
| US6420567B1 (en) | 1996-09-27 | 2002-07-16 | Texas Biotechnology Corporation | N-heteroaryl aryl-substituted thienyl-furyl-and pyrrolyl-sulfonamides and derviatives thereof that modulate the activity of endothelin |
| US6248767B1 (en) | 1997-04-28 | 2001-06-19 | Texas Biotechnology Corp. | Formulation of sulfonamides for treatment of endothelin-mediated disorders |
| JP2001026506A (en) * | 1999-04-28 | 2001-01-30 | Takeda Chem Ind Ltd | Sulfonamide derivative |
| US6586617B1 (en) | 1999-04-28 | 2003-07-01 | Sumitomo Chemical Takeda Agro Company, Limited | Sulfonamide derivatives |
| EP3482964A1 (en) * | 2017-11-13 | 2019-05-15 | Mitsubishi HiTec Paper Europe GmbH | Heat-sensitive recording medium based on pla |
| WO2019091813A1 (en) * | 2017-11-13 | 2019-05-16 | Mitsubishi Hitec Paper Europe Gmbh | Heat-sensitive pla-based recording material |
| US11911372B2 (en) | 2018-06-28 | 2024-02-27 | Ctxt Pty Ltd | Compounds |
| US11492346B2 (en) | 2019-06-18 | 2022-11-08 | Pfizer Inc. | Benzisoxazole sulfonamide derivatives |
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