JPS6250444B2 - - Google Patents
Info
- Publication number
- JPS6250444B2 JPS6250444B2 JP53045766A JP4576678A JPS6250444B2 JP S6250444 B2 JPS6250444 B2 JP S6250444B2 JP 53045766 A JP53045766 A JP 53045766A JP 4576678 A JP4576678 A JP 4576678A JP S6250444 B2 JPS6250444 B2 JP S6250444B2
- Authority
- JP
- Japan
- Prior art keywords
- weight
- general formula
- parts
- water
- solvent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000004009 herbicide Substances 0.000 claims description 15
- 230000002363 herbicidal effect Effects 0.000 claims description 13
- FBOSKQVOIHEWAX-UHFFFAOYSA-N benzothiazine Chemical class C1=CC=C2N=CCSC2=C1 FBOSKQVOIHEWAX-UHFFFAOYSA-N 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- -1 halogenated acetyl halide Chemical class 0.000 description 27
- 241000196324 Embryophyta Species 0.000 description 23
- 150000001875 compounds Chemical class 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 239000000203 mixture Substances 0.000 description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 238000004519 manufacturing process Methods 0.000 description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- 239000002904 solvent Substances 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 239000013078 crystal Substances 0.000 description 10
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- VRVRGVPWCUEOGV-UHFFFAOYSA-N 2-aminothiophenol Chemical class NC1=CC=CC=C1S VRVRGVPWCUEOGV-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- 239000002689 soil Substances 0.000 description 7
- 244000301850 Cupressus sempervirens Species 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 6
- 239000008096 xylene Substances 0.000 description 6
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000004927 clay Substances 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 235000013312 flour Nutrition 0.000 description 4
- 239000012046 mixed solvent Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 3
- 235000004135 Amaranthus viridis Nutrition 0.000 description 3
- 244000025254 Cannabis sativa Species 0.000 description 3
- 235000009344 Chenopodium album Nutrition 0.000 description 3
- 240000000005 Chenopodium berlandieri Species 0.000 description 3
- 235000005484 Chenopodium berlandieri Nutrition 0.000 description 3
- 235000009332 Chenopodium rubrum Nutrition 0.000 description 3
- 241000234653 Cyperus Species 0.000 description 3
- 244000058871 Echinochloa crus-galli Species 0.000 description 3
- 229920001732 Lignosulfonate Polymers 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 244000078534 Vaccinium myrtillus Species 0.000 description 3
- 239000000440 bentonite Substances 0.000 description 3
- 229910000278 bentonite Inorganic materials 0.000 description 3
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 3
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- 235000013311 vegetables Nutrition 0.000 description 3
- 239000004563 wettable powder 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
- XERMPLQXCQQVGU-UHFFFAOYSA-N 2-amino-3-chlorobenzenethiol Chemical compound NC1=C(S)C=CC=C1Cl XERMPLQXCQQVGU-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
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 235000003222 Helianthus annuus Nutrition 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 244000234609 Portulaca oleracea Species 0.000 description 2
- 235000001855 Portulaca oleracea Nutrition 0.000 description 2
- 241000208422 Rhododendron Species 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 2
- 235000003095 Vaccinium corymbosum Nutrition 0.000 description 2
- 235000017537 Vaccinium myrtillus Nutrition 0.000 description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 235000021014 blueberries Nutrition 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 230000001629 suppression Effects 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- FXSNTBPVBODIRX-UHFFFAOYSA-N (2,5-dimethylpyrazol-3-yl) 4-methylbenzenesulfonate Chemical compound CN1N=C(C)C=C1OS(=O)(=O)C1=CC=C(C)C=C1 FXSNTBPVBODIRX-UHFFFAOYSA-N 0.000 description 1
- IXJJELULBDAIMY-UHFFFAOYSA-N 1,2,5,6-tetrahydrotriazine Chemical compound C1CC=NNN1 IXJJELULBDAIMY-UHFFFAOYSA-N 0.000 description 1
- LIVCNGIOYZNYHR-UHFFFAOYSA-N 1-[amino(hydroxy)phosphinothioyl]oxybutane Chemical group CCCCOP(N)(O)=S LIVCNGIOYZNYHR-UHFFFAOYSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 1
- HXKWSTRRCHTUEC-UHFFFAOYSA-N 2,4-Dichlorophenoxyaceticacid Chemical compound OC(=O)C(Cl)OC1=CC=C(Cl)C=C1 HXKWSTRRCHTUEC-UHFFFAOYSA-N 0.000 description 1
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 1
- IHCCLXNEEPMSIO-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical group C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 IHCCLXNEEPMSIO-UHFFFAOYSA-N 0.000 description 1
- QAKGZDFJIHWLST-UHFFFAOYSA-N 2-amino-3-bromobenzenethiol Chemical compound NC1=C(S)C=CC=C1Br QAKGZDFJIHWLST-UHFFFAOYSA-N 0.000 description 1
- OKHXTOSPFFCZOY-UHFFFAOYSA-N 2-chloro-n-(2-fluoro-6-sulfanylphenyl)acetamide Chemical compound FC1=CC=CC(S)=C1NC(=O)CCl OKHXTOSPFFCZOY-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- HXDLWJWIAHWIKI-UHFFFAOYSA-N 2-hydroxyethyl acetate Chemical compound CC(=O)OCCO HXDLWJWIAHWIKI-UHFFFAOYSA-N 0.000 description 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 description 1
- CTSLUCNDVMMDHG-UHFFFAOYSA-N 5-bromo-3-(butan-2-yl)-6-methylpyrimidine-2,4(1H,3H)-dione Chemical compound CCC(C)N1C(=O)NC(C)=C(Br)C1=O CTSLUCNDVMMDHG-UHFFFAOYSA-N 0.000 description 1
- VEECXNHIJFGTAK-UHFFFAOYSA-N 5-chloro-4h-1,4-benzothiazin-3-one Chemical compound S1CC(=O)NC2=C1C=CC=C2Cl VEECXNHIJFGTAK-UHFFFAOYSA-N 0.000 description 1
- CZDACSGUEPPLAG-UHFFFAOYSA-N 5-fluoro-4h-1,4-benzothiazin-3-one Chemical compound S1CC(=O)NC2=C1C=CC=C2F CZDACSGUEPPLAG-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 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
- 244000105624 Arachis hypogaea Species 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- 229920002871 Dammar gum Polymers 0.000 description 1
- 239000004860 Dammar gum Substances 0.000 description 1
- 235000001602 Digitaria X umfolozi Nutrition 0.000 description 1
- 240000003176 Digitaria ciliaris Species 0.000 description 1
- 235000017898 Digitaria ciliaris Nutrition 0.000 description 1
- 235000005476 Digitaria cruciata Nutrition 0.000 description 1
- 235000006830 Digitaria didactyla Nutrition 0.000 description 1
- 235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 description 1
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 1
- 240000003173 Drymaria cordata Species 0.000 description 1
- 235000014716 Eleusine indica Nutrition 0.000 description 1
- 241000237858 Gastropoda Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 241000208818 Helianthus Species 0.000 description 1
- 244000020551 Helianthus annuus Species 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 240000008415 Lactuca sativa Species 0.000 description 1
- 235000003228 Lactuca sativa Nutrition 0.000 description 1
- 239000005574 MCPA Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 240000000249 Morus alba Species 0.000 description 1
- 235000008708 Morus alba Nutrition 0.000 description 1
- 240000009253 Morus australis Species 0.000 description 1
- XGEGHDBEHXKFPX-UHFFFAOYSA-N N-methylthiourea Natural products CNC(N)=O XGEGHDBEHXKFPX-UHFFFAOYSA-N 0.000 description 1
- LVKTWOXHRYGDMM-UHFFFAOYSA-N Naproanilide Chemical compound C=1C=C2C=CC=CC2=CC=1OC(C)C(=O)NC1=CC=CC=C1 LVKTWOXHRYGDMM-UHFFFAOYSA-N 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- CHNUNORXWHYHNE-UHFFFAOYSA-N Oxadiazon Chemical compound C1=C(Cl)C(OC(C)C)=CC(N2C(OC(=N2)C(C)(C)C)=O)=C1Cl CHNUNORXWHYHNE-UHFFFAOYSA-N 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- 241000209504 Poaceae Species 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 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
- 244000184734 Pyrus japonica Species 0.000 description 1
- 244000088415 Raphanus sativus Species 0.000 description 1
- 235000006140 Raphanus sativus var sativus Nutrition 0.000 description 1
- WOZQBERUBLYCEG-UHFFFAOYSA-N SWEP Chemical compound COC(=O)NC1=CC=C(Cl)C(Cl)=C1 WOZQBERUBLYCEG-UHFFFAOYSA-N 0.000 description 1
- 241000269796 Seriola quinqueradiata Species 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 229910052586 apatite Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 229910002114 biscuit porcelain Inorganic materials 0.000 description 1
- HKPHPIREJKHECO-UHFFFAOYSA-N butachlor Chemical compound CCCCOCN(C(=O)CCl)C1=C(CC)C=CC=C1CC HKPHPIREJKHECO-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- XQNAUQUKWRBODG-UHFFFAOYSA-N chlornitrofen Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=C(Cl)C=C(Cl)C=C1Cl XQNAUQUKWRBODG-UHFFFAOYSA-N 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- GQDAQMBBGHMTQX-UHFFFAOYSA-N dihydroxy-propylsulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound CCCSP(O)(O)=S GQDAQMBBGHMTQX-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 description 1
- 229940071161 dodecylbenzenesulfonate Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- OXHDYFKENBXUEM-UHFFFAOYSA-N glyphosine Chemical compound OC(=O)CN(CP(O)(O)=O)CP(O)(O)=O OXHDYFKENBXUEM-UHFFFAOYSA-N 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- QPPQHRDVPBTVEV-UHFFFAOYSA-N isopropyl dihydrogen phosphate Chemical compound CC(C)OP(O)(O)=O QPPQHRDVPBTVEV-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
- 238000004898 kneading Methods 0.000 description 1
- ZTMKADLOSYKWCA-UHFFFAOYSA-N lenacil Chemical compound O=C1NC=2CCCC=2C(=O)N1C1CCCCC1 ZTMKADLOSYKWCA-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 229910052751 metal Chemical class 0.000 description 1
- 239000002184 metal Chemical class 0.000 description 1
- XGEGHDBEHXKFPX-NJFSPNSNSA-N methylurea Chemical compound [14CH3]NC(N)=O XGEGHDBEHXKFPX-NJFSPNSNSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- VSIIXMUUUJUKCM-UHFFFAOYSA-D pentacalcium;fluoride;triphosphate Chemical compound [F-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O VSIIXMUUUJUKCM-UHFFFAOYSA-D 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 239000013459 phenoxy herbicide Substances 0.000 description 1
- 230000008654 plant damage Effects 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 206010039083 rhinitis Diseases 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- MGLWZSOBALDPEK-UHFFFAOYSA-N simetryn Chemical compound CCNC1=NC(NCC)=NC(SC)=N1 MGLWZSOBALDPEK-UHFFFAOYSA-N 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- 229940035893 uracil Drugs 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
- 229940007718 zinc hydroxide Drugs 0.000 description 1
- 229910021511 zinc hydroxide Inorganic materials 0.000 description 1
Landscapes
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
本発明は一般式
〔式中、Xはハロゲン原子を表わし、Yは酸素
原子またはイオウ原子を表わす。〕
で示される1,4―ベンゾチアジン誘導体を有効
成分として含有することを特徴とする除草剤(以
下、本発明組成物と称する。)に関するものであ
る。
一般式()で示される化合物は以下に示す製
造法A,B,CまたはDによつて製造される。す
なわち
(1) 一般式()
〔式中、Xはハロゲン原子を表わす。〕
で示されるアミノチオフエノール誘導体と一般
式()
UCH2COOH ()
〔式中、Uはハロゲン原子を表わす。〕
で示されるハロゲン化酢酸とを塩基の存在下反
応させることにより、一般式
〔式中、Xは前述のとおりである。〕
で示される1,4―ベンゾチアジン誘導体を製
造することができる(以後、製造法Aと称す
る)。
(2) 一般式()で示されるアミノチオフエノー
ル誘導体と
一般式()
〔式中、VおよびWはそれぞれハロゲン原子
を表わす。〕
で示されるハロゲン化アセチルハライドとを反
応させることにより、一般式
〔式中、Xは前述のとおりである。〕
で示される1,4―ベンゾチアジン誘導体を製
造することができる(以後、製造法Bと称す
る)。
(3) 一般式()
〔式中、Xは前述のとおりであり、Zはハロ
ゲン原子を表わす。〕
で示されるアミノチオフエノール誘導体を好ま
しくは塩基の存在下、閉環させることにより一
般式
〔式中、Xは前述のとおりである。〕
で示される1,4―ベンゾチアジン誘導体を製
造することができる(以後、製造法Cと称す
る)。
(4) 一般式()
〔式中、Xは前述のとおりである。〕
で示されるベンゾチアジン誘導体と五硫化リン
とを反応させることにより一般式
〔式中、Xは前述のとおりである。〕
で示される1,4―ベンゾチアジン誘導体を製
造することができる(以後、製造法Dと称す
る)。
本発明組成物は、除草作用を有し、ヒエ、メヒ
シバ、エノコログサ、スズメノテツポウ等のイネ
科の畑地雑草、カヤツリグサ、アオビユ、シロ
ザ、スベリヒユ、ハコベ等の広葉畑地雑草に、ま
たタイヌビエ、コナギ、キカシグサ、アブノメ等
の水田一年生雑草に対しても強い作用をもつ。
本発明組成物は、近年問題となつている多年生
雑草のミズガヤツリ、ウリカワ、ホタルイ、クロ
グワイ、マツバイ等に対しても一年生雑草と同
様、発芽前および生育期処理で強い活性を示し、
幅広い殺草スペクトラムを有することが特長であ
る。
また、畑地用に使用する場合も畑地の主要雑草
に効力が強い上、雑草の発生前に行なう土壌処理
でも、生育初期に行なう茎葉処理でも効果をも
ち、しかもイネ、ダイズ、ワタ、トウモロコシ、
落花生、ヒマワリ等の各主要作物に害がなく、レ
タス、ダイイコン等の野菜にも安全に使用できる
という非常にすぐれた性質を有している。
本発明組成物は水稲用としてはもちろん各種穀
類、そ菜類、果樹園、芝生、牧草地、茶園、桑
園、ゴム園、森林地、非農耕地等の除草剤として
有用である。
つぎに本発明組成物の製造法についてさらに詳
しく説明する。
製造法Aにおいては、一般式()で示される
アミノチオフエノール誘導体を適当な溶媒、たと
えば水、エタノール、メタノール、ベンゼン、ト
ルエン、キシレン、テトラヒドロフラン、ジオキ
サン、エチルエーテル、クロロホルム、四塩化炭
素、酢酸エチル、DMF、DMSO等またはそれら
の混合溶媒中で適当な塩基剤、たとえばピリジ
ン、トリエチルアミン、トリメチルアミン等の三
級アミンまたは水酸化ナトリウム、水酸化カリウ
ム、水酸化亜鉛、水酸化マグネシウム、ナトリウ
ム、水素化ナトリウム、カリウムターシヤリーブ
トキシド、ナトリウムエトキシド、ナトリウムメ
トキシド、n―ブチルリチウム等の存在下、一般
式()で示されるハロゲン化酢酸を混和し、適
当な温度、たとえば0℃〜150℃で0.5〜24時間撹
拌し、水溶媒のときは目的とする化合物を結晶と
して得る。また、その他の有機溶媒を使用したと
きは、溶媒を留去し、残渣を水洗して目的とする
化合物を結晶として得る。
また、一般式()で示されるアミノチオフエ
ノール誘導体をあらかじめナトリウム、カリウム
等のアルカリ金属、カルシウム、バリウム等のア
ルカリ土類金属またはマグネシウム、亜鉛等の金
属塩とした後、塩基剤の存在なしで上記の反応を
行ない、目的化合物を得ることも可能である。こ
れらの目的化合物は再結晶、カラムクロマト等一
般的な精製手段でさらに純化することが可能であ
る。
製造法Bにおいては、一般式()で示される
アミノチオフエノール誘導体を適当な溶媒、たと
えば水、エタノール、メタノール、ベンゼン、ト
ルエン、キシレン、テトラヒドロフラン、ジオキ
サン、エチルエーテル、クロロホルム、四塩化炭
素、酢酸エチル、DMF、DMSO等またはそれら
の混合溶媒中で適当な塩基剤、たとえばピリジ
ン、トリエチルアミン、トリメチルアミン等の三
級アミンまたは水酸化ナトリウム、水酸化カリウ
ム、ナトリウム、水素化ナトリウム、カリウムタ
ーシヤリーブトキシド、ナトリウムエトキシド、
ナトリウムメトキシド、n―ブチルリチウム等の
存在下、一般式()で示されるハロゲン化アセ
チルハライドを混和し、適当な温度、たとえば0
℃〜150℃で0.5〜20時間撹拌した後、水中にあけ
結晶が析出する場合はろ過水洗し、乾燥して目的
物を得る。結晶化しない場合は適当な抽出溶媒で
抽出し、溶媒を乾燥後、留去して目的とする化合
物を結晶として得る。これらの目的化合物は再結
晶、カラムクロマト等一般的な精製手段でさらに
純化することが可能である。
製造法Cにおいては、一般式()で示される
アミノチオフエノール誘導体を適当な溶媒、たと
えば水、エタノール、メタノール、ベンゼン、ト
ルエン、キシレン、テトラヒドロフラン、ジオキ
サン、エチルエーテル、クロロホルム、四塩化炭
素、酢酸エチル、DMF、DMSO等またはそれら
の混合溶媒中で、好ましくは適当な塩基剤、たと
えばピリジン、トリエチルアミン、トリメチルア
ミン等の三級アミンまたは水酸化ナトリウム、水
酸化カリウム、ナトリウム、水素化ナトリウム、
カリウムターシヤリーブトキシド、ナトリウムエ
トキシド、ナトリウムメトキシド、n―ブチルリ
チウム等の存在下、適当な温度、たとえば0℃〜
150℃で0.5〜24時間撹拌した後、水溶媒のときは
目的とする化合物を結晶として得る。またその他
の有機溶媒を使用したときは、溶媒を留去し、残
渣を水洗して目的とする化合物を結晶として得
る。
これらの目的化合物は再結晶、カラムクロマト
等一般的な精製手段でさらに純化することが可能
である。
製造法Dにおいては、一般式()で示される
ベンゾチアジン誘導体を適当な溶媒、たとえばベ
ンゼン、トルエン、キシレン、クロロホルム、四
塩化炭素、ピリジン等またはそれらの混合溶媒中
で五硫化リンと共に適当な温度、たとえば60〜
140℃で適当な時間、たとえば1〜10時間加熱し
た後、熱時セライトろ過し、溶媒を留去後、また
は溶媒がピリジンのときは水中にあけて目的とす
る化合物を得る。これらの目的化合物は再結晶、
カラムクロマト等一般的な精製手段でさらに純化
することが可能である。
上記の方法で得た一般式()で示される化合
物の代表例を第1表に示すが、もちろん本発明は
これらのみに限定されるものではない。
The present invention is based on the general formula [In the formula, X represents a halogen atom, and Y represents an oxygen atom or a sulfur atom. ] The present invention relates to a herbicide (hereinafter referred to as the composition of the present invention) characterized by containing the 1,4-benzothiazine derivative shown below as an active ingredient. The compound represented by the general formula () is manufactured by the manufacturing method A, B, C or D shown below. That is, (1) General formula () [In the formula, X represents a halogen atom. ] An aminothiophenol derivative represented by the general formula () UCH 2 COOH () [wherein U represents a halogen atom. ] By reacting the halogenated acetic acid represented by the formula in the presence of a base, the general formula [In the formula, X is as described above.] ] A 1,4-benzothiazine derivative represented by the following can be produced (hereinafter referred to as production method A). (2) Aminothiophenol derivative represented by general formula () and general formula () [In the formula, V and W each represent a halogen atom. ] By reacting with a halogenated acetyl halide represented by the general formula [In the formula, X is as described above.] ] A 1,4-benzothiazine derivative represented by the following can be produced (hereinafter referred to as production method B). (3) General formula () [In the formula, X is as described above, and Z represents a halogen atom. ] By ring-closing the aminothiophenol derivative represented by, preferably in the presence of a base, the general formula [In the formula, X is as described above.] ] A 1,4-benzothiazine derivative represented by the following can be produced (hereinafter referred to as production method C). (4) General formula () [In the formula, X is as described above. ] By reacting the benzothiazine derivative represented by the formula with phosphorus pentasulfide, the general formula [In the formula, X is as described above. ] A 1,4-benzothiazine derivative represented by the following can be produced (hereinafter referred to as production method D). The composition of the present invention has a herbicidal effect, and is effective against field weeds of the Poaceae family, such as barnyard grass, blackberry, foxtail grass, and staghorn grass, as well as broad-leaved field weeds, such as cyperus, cyperus, purslane, purslane, and chickweed. It also has a strong effect on annual weeds in paddy fields such as snail. The composition of the present invention exhibits strong activity against perennial weeds that have become a problem in recent years, such as Japanese cypress, Japanese cypress, Japanese cypress, Japanese cypress, Japanese cypress, etc., as well as annual weeds, when treated before germination and during the growing season.
Its feature is that it has a wide herbicidal spectrum. In addition, when used in fields, it is highly effective against major weeds in fields, and is effective both in soil treatment before weeds emerge and in foliage treatment in the early stages of growth.
It has excellent properties such as being harmless to major crops such as peanuts and sunflowers, and can be safely used on vegetables such as lettuce and radish. The composition of the present invention is useful not only as a herbicide for paddy rice but also for various grains, vegetables, orchards, lawns, pastures, tea gardens, mulberry gardens, rubber gardens, forests, non-agricultural lands, and the like. Next, the method for producing the composition of the present invention will be explained in more detail. In production method A, the aminothiophenol derivative represented by the general formula () is dissolved in a suitable solvent such as water, ethanol, methanol, benzene, toluene, xylene, tetrahydrofuran, dioxane, ethyl ether, chloroform, carbon tetrachloride, ethyl acetate. , DMF, DMSO, etc., or a mixed solvent thereof, with a suitable base agent, such as a tertiary amine such as pyridine, triethylamine, trimethylamine, or sodium hydroxide, potassium hydroxide, zinc hydroxide, magnesium hydroxide, sodium, sodium hydride. , potassium tertiary butoxide, sodium ethoxide, sodium methoxide, n-butyl lithium, etc., are mixed with a halogenated acetic acid represented by the general formula (), and the mixture is heated to a temperature of 0.5 to 150°C at an appropriate temperature, for example, 0°C to 150°C. Stir for 24 hours, and when using water as a solvent, obtain the desired compound as crystals. When other organic solvents are used, the solvent is distilled off and the residue is washed with water to obtain the desired compound as crystals. In addition, after the aminothiophenol derivative represented by the general formula () is converted into a salt of an alkali metal such as sodium or potassium, an alkaline earth metal such as calcium or barium, or a metal salt such as magnesium or zinc, the aminothiophenol derivative may be prepared without the presence of a base agent. It is also possible to carry out the above reaction to obtain the target compound. These target compounds can be further purified by general purification methods such as recrystallization and column chromatography. In production method B, the aminothiophenol derivative represented by the general formula () is mixed with a suitable solvent such as water, ethanol, methanol, benzene, toluene, xylene, tetrahydrofuran, dioxane, ethyl ether, chloroform, carbon tetrachloride, ethyl acetate. , DMF, DMSO, etc., or a mixed solvent thereof, with a suitable base agent, such as tertiary amines such as pyridine, triethylamine, trimethylamine, or sodium hydroxide, potassium hydroxide, sodium, sodium hydride, potassium tertiary butoxide, sodium ethoxy. Do,
In the presence of sodium methoxide, n-butyllithium, etc., a halogenated acetyl halide represented by the general formula () is mixed and heated at an appropriate temperature, e.g.
After stirring at ℃~150℃ for 0.5~20 hours, pour into water and if crystals precipitate, filter, wash with water, and dry to obtain the desired product. If it does not crystallize, extract with a suitable extraction solvent, dry the solvent, and then evaporate to obtain the desired compound as crystals. These target compounds can be further purified by general purification methods such as recrystallization and column chromatography. In production method C, the aminothiophenol derivative represented by the general formula () is mixed with a suitable solvent such as water, ethanol, methanol, benzene, toluene, xylene, tetrahydrofuran, dioxane, ethyl ether, chloroform, carbon tetrachloride, ethyl acetate. , DMF, DMSO, etc. or a mixed solvent thereof, preferably a suitable base agent such as pyridine, a tertiary amine such as triethylamine, trimethylamine, or sodium hydroxide, potassium hydroxide, sodium, sodium hydride,
In the presence of potassium tertiary butoxide, sodium ethoxide, sodium methoxide, n-butyllithium, etc., at an appropriate temperature, e.g., 0°C to
After stirring at 150°C for 0.5 to 24 hours, the desired compound is obtained as crystals when the solvent is water. When other organic solvents are used, the solvent is distilled off and the residue is washed with water to obtain the desired compound as crystals. These target compounds can be further purified by general purification methods such as recrystallization and column chromatography. In production method D, a benzothiazine derivative represented by the general formula () is mixed with phosphorus pentasulfide in an appropriate solvent such as benzene, toluene, xylene, chloroform, carbon tetrachloride, pyridine, etc. or a mixed solvent thereof at an appropriate temperature, For example 60~
After heating at 140° C. for an appropriate time, for example 1 to 10 hours, the mixture is filtered through Celite while hot, and the solvent is distilled off, or when the solvent is pyridine, poured into water to obtain the desired compound. These target compounds are recrystallized,
It is possible to further purify using general purification means such as column chromatography. Representative examples of compounds represented by the general formula () obtained by the above method are shown in Table 1, but the present invention is of course not limited to these.
【表】【table】
【表】
本発明組成物を実際に使用する際は、原体その
ものを散布してもよいし、粒剤、水和剤、乳剤等
のいずれの製剤形態のものでも使用できる。これ
らの製剤品を作成するにあたつて、固体担体とし
ては、たとえば鉱物質粉末(カオリン、ベントナ
イト、クレー、モンモリロナイト、タルク、珪藻
土、雲母、バーミキユライト、石こう、炭酸カル
シウム、リン灰石など)、植物質粉末(大豆粉、
小麦粉、木粉、タバコ粉、でんぷん、結晶性セル
ロースなど)、高分子化合物(石油樹脂、ポリ塩
化ビニル、ダンマルガム、ケトン樹脂など)、さ
らにアルミナ、ワツクス類などがあげられる。
また液体担体としては、たとえばアルコール類
(メチルアルコールなど)、芳香族炭化水素類(ト
ルエン、ベンゼン、キシレン、メチルナフタレン
など)、塩素化炭化水素類(クロロホルム、四塩
化炭素、モノクロロベンゼンなど)、エーテル類
(ジオキサン、テトラハイドロフランなど)、ケト
ン類(アセトン、メチルエチルケトン、シクロヘ
キサノンなど)、エステル類(酢酸エチル、酢酸
ブチル、エチレングリコールアセテートなど)、
酸アミド類(ジメチルホルムアミドなど)、ニト
リル類(アセトニトリルなど)、エーテルアルコ
ール類(エチレングリコールエチルエーテルな
ど)、水などがあげられる。
乳化、分散、拡散等の目的で使用される界面活
性剤は非イオン性、陰イオン性、陽イオン性、両
性イオン性のいずれのものも使用できる。使用さ
れる界面活性剤の例をあげると、ポリオキシエチ
レンアルキルエーテル、ポリオキシエチレンアル
キルアリールエーテル、ポリオキシエチレン脂肪
酸エステル、ソルビタン脂肪酸エステル、ポリオ
キシエチレンソルビタン脂肪酸エステル、オキシ
エチレンオキシプロピレンポリマー、ポリオキシ
エチレンアルキルリン酸エステル、脂肪酸塩、ア
ルキル硫酸エステル塩、アルキルスルホン酸塩、
アルキルアリールスルホン酸塩、アルキルリン酸
エステル塩、ポリオキシエチレンアルキル硫酸エ
ステル、第4級アンモニウム塩、オキシルアルキ
ルアミン等であるが、もちろんこれらのみに限定
されるものではない。また、これらの目的には必
要に応じてゼラチン、カゼイン、アルギン酸ソー
ダ、澱粉、寒天、ポリビニルアルコールなどを補
助剤として用いることができる。
次に製剤例を示す。
製剤例 1
化合物(1)25重量部、ドデシルベンゼンスルホン
酸塩2.5重量部、リグニンスルホン酸塩2.5重量部
および珪藻土70重量部をよく粉砕混和して水和剤
を得る。
製剤例 2
化合物(2)30重量部、乳化剤ソルポールSM100
(東邦化学登録商標名)10重量部およびキシレン
60重量部をよく混合して乳剤を得る。
製剤例 3
化合物(1)5重量部、ホワイトカーボン1重量
部、リグニンスルホン酸塩5重量部およびクレー
89重量部をよく粉砕混合し、水を加えてよく練り
合わせた後、造粒乾燥して粒剤を得る。
製剤例 4
化合物(4)3重量部、リン酸イソプロピル1重量
部、クレー66重量部およびタルク30重量部をよく
粉砕混合して粉剤を得る。
製剤例 5
ベントナイト40重量部、リグニンスルホン酸塩
5重量部およびクレー55重量部を粉砕混合し、加
水、混練後、造粒乾燥し、活性成分を含まない粒
状物を作る。この粒状物95重量部に化合物(5)を5
重量部含浸させて粒剤を得る。
製剤例 6
16〜48メツシユに篩別したベントナイト95重量
部に化合物(1)5重量部を含浸させて粒剤を得る。
また、本発明組成物は除草剤としての効力向上
を目指し、他の除草剤との混用も可能であり、場
合によつては相乗効果を期待することもできる。
この例としては、たとえば2,4―ジクロルフエ
ノキシ酢酸;2―メチル―4―クロルフエノキシ
酢酸(エステル、塩類を含む)等のフエノキシ系
除草剤、2,4―ジクロルフエニル―4′―ニトロ
フエニルエーテル;2,4,6―トリクロレフエ
ニル―4′―ニトロフエニルエーテル;2―クロロ
―4―トリフルオロメチルフエニル―3′―エトキ
シ―4′―ニトロフエニルエール;2,4―ジクロ
ルフエニル―4′―ニトロ―3′―メトキシフエニル
エーテル;2,4―ジクロルフエニル―3′―メト
キシカルボニル―4′―ニトロフエニルエーテル等
のジフエニルエーテル系除草剤、2―クロル―
4,6―ビスエチルアミノー1,3,5―トリア
ジン;2―クロル―4―エチルアミノ―6―イソ
プロピルアミノー1,3,5―トリアジン;2―
メチルチオー4,6―ビスエチルアミノー1,
3,5―トリアジン;2―メチルチオー4,6―
ビスイソプロピルアミノ―1,3,5―トリアジ
ン等のトリアジン系除草剤、3―(3,4―ジク
ロルフエニル)―1,1―ジメチルウレア;3―
(3,4―ジクロルフエニル)―メトキシ―1―
メチルウレア、1―(2,2―ジメチルベンジ
ル)―3―P―トリルウレア等の尿素系除草剤、
イソプロピル―N―(3―クロルフエニルカーバ
メイト;メチル―N―(3,4―ジクロルフエニ
ル)カーバメイト等のカーバメイト系除草剤、S
―(4―クロルベンジル)―N,N―ジエチルチ
オールカーバメイト;S―エチル―N,N―ヘキ
サメチレンチオールカーバメイト等のチオールカ
ーバメイト系除草剤、3,4―ジクロルプロピオ
ンアニリド;N―メトキシメチル―2,6―ジエ
チル―α―クロルアセトアニリド;2―クロル―
2′,6′―ジエチル―N―(ブトキシメチル)―ア
セトアニリド;N―クロルアセチル―N―(2,
6―ジエチルフエニル)―グリシンエチルエステ
ル等の酸アニリド系除草剤、5―ブロム―3―セ
カンダリ―ブチル―6―メチルウラシル;3―シ
クロヘキシル―5,6―トリメチレンウラシル等
のウラシル系除草剤、1,1′―ジメチル―4,4
―ビスピリジニウムクロライド等のピリジニウム
塩素系除草剤、N,N―ビス(ホスホノメチル)
―グリシン、O―エチル―O―(2―ニトロ―5
―メチルフエニル)―N―セカンダリーブチルホ
スホロアミドチオエート、S―(2―メチル―1
―ピペリジルカルボニルメチル)―O,O―ジ―
n―プロピルジチオホスフエート等のリン系除草
剤、α,α,α―トリフルオロー2,6―ジニト
ロ―N,N―ジプロピル―P―トルイジン等のト
ルイジン系除草剤、5―ターシヤリーブチル―3
―(2,4―ジクロル―5―イソプロポキシフエ
ニル)―1,3,4―オキサジアゾリン―2―オ
ン;3―イソプロピル―1H―2,1,3―ベン
ゾチアジアジン―(4)―3H―オン―2,2―ジオ
キシド、α(β―ナフトキシ)―プロピオンアニ
ライド、4―(2,4―ジクロロベンゾイル)―
1,3―ジメチルピラゾール―5―イル p―ト
ルエンスルホネートなどがあげられるが、これら
に限られるものではない。
さらに本発明組成物は必要に応じて殺虫剤、殺
線虫剤、殺菌剤、植物生長調節剤および肥料等と
の混用も可能である。
次に一般式〔〕で示される化合物の製造例を
参考例として示す。
参考例1 (製造法A)
水40ml中に水酸化ナトリウム690mgを溶解した
後、2―アミノ―3―クロロチオフエノール2.5
gを溶解させ、撹拌しながらブロム酢酸2.4gを
加える。70℃で3時間撹拌した後、析出した結晶
をろ過し、水洗後乾燥して目的とする5―クロロ
―2,3―ジヒドロ―1,4―ベンゾチアジン―
3―オンm.p160〜161℃)2.98gを得た。[Table] When actually using the composition of the present invention, the raw material itself may be sprayed, or any formulation form such as granules, wettable powders, emulsions, etc. may be used. In preparing these pharmaceutical products, solid carriers include, for example, mineral powders (kaolin, bentonite, clay, montmorillonite, talc, diatomaceous earth, mica, vermiculite, gypsum, calcium carbonate, apatite, etc.). , vegetable powder (soybean flour,
Wheat flour, wood flour, tobacco flour, starch, crystalline cellulose, etc.), polymer compounds (petroleum resin, polyvinyl chloride, dammar gum, ketone resin, etc.), alumina, waxes, etc. Examples of liquid carriers include alcohols (methyl alcohol, etc.), aromatic hydrocarbons (toluene, benzene, xylene, methylnaphthalene, etc.), chlorinated hydrocarbons (chloroform, carbon tetrachloride, monochlorobenzene, etc.), and ether. (dioxane, tetrahydrofuran, etc.), ketones (acetone, methyl ethyl ketone, cyclohexanone, etc.), esters (ethyl acetate, butyl acetate, ethylene glycol acetate, etc.),
Examples include acid amides (such as dimethylformamide), nitriles (such as acetonitrile), ether alcohols (such as ethylene glycol ethyl ether), and water. The surfactant used for the purpose of emulsification, dispersion, diffusion, etc. may be nonionic, anionic, cationic, or amphoteric. Examples of surfactants used include polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether, polyoxyethylene fatty acid ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, oxyethylene oxypropylene polymer, polyoxy Ethylene alkyl phosphate, fatty acid salt, alkyl sulfate, alkyl sulfonate,
These include alkylaryl sulfonates, alkyl phosphate ester salts, polyoxyethylene alkyl sulfate esters, quaternary ammonium salts, oxylalkyl amines, and the like, but are of course not limited to these. Furthermore, for these purposes, gelatin, casein, sodium alginate, starch, agar, polyvinyl alcohol, and the like may be used as adjuvants, if necessary. Examples of formulations are shown below. Formulation Example 1 25 parts by weight of compound (1), 2.5 parts by weight of dodecylbenzenesulfonate, 2.5 parts by weight of lignosulfonate and 70 parts by weight of diatomaceous earth are thoroughly ground and mixed to obtain a wettable powder. Formulation example 2 Compound (2) 30 parts by weight, emulsifier Solpol SM100
(Toho Chemical registered trademark name) 10 parts by weight and xylene
Mix 60 parts by weight thoroughly to obtain an emulsion. Formulation Example 3 5 parts by weight of compound (1), 1 part by weight of white carbon, 5 parts by weight of lignin sulfonate and clay
After thoroughly grinding and mixing 89 parts by weight, adding water and kneading well, the mixture is granulated and dried to obtain granules. Formulation Example 4 3 parts by weight of compound (4), 1 part by weight of isopropyl phosphate, 66 parts by weight of clay and 30 parts by weight of talc are thoroughly ground and mixed to obtain a powder. Formulation Example 5 40 parts by weight of bentonite, 5 parts by weight of lignin sulfonate and 55 parts by weight of clay are pulverized and mixed, water is added and kneaded, followed by granulation and drying to produce granules containing no active ingredient. Add 5 parts of compound (5) to 95 parts by weight of this granule.
Granules are obtained by impregnating parts by weight. Formulation Example 6 Granules are obtained by impregnating 95 parts by weight of bentonite sieved to 16-48 mesh with 5 parts by weight of compound (1). Furthermore, the composition of the present invention can be used in combination with other herbicides in order to improve its effectiveness as a herbicide, and in some cases a synergistic effect can be expected.
Examples include phenoxy herbicides such as 2,4-dichlorophenoxyacetic acid; 2-methyl-4-chlorophenoxyacetic acid (including esters and salts), and 2,4-dichlorophenyl-4'-nitrophenyl. Ether; 2,4,6-trichlorophenyl-4'-nitrophenyl ether; 2-chloro-4-trifluoromethylphenyl-3'-ethoxy-4'-nitrophenyl ale; 2,4-dichlorophenyl -4'-nitro-3'-methoxyphenyl ether; diphenyl ether herbicides such as 2,4-dichlorophenyl-3'-methoxycarbonyl-4'-nitrophenyl ether, 2-chloro-
4,6-bisethylamino-1,3,5-triazine; 2-chloro-4-ethylamino-6-isopropylamino-1,3,5-triazine; 2-
Methylthio 4,6-bisethylamino 1,
3,5-triazine; 2-methylthio 4,6-
Triazine herbicides such as bisisopropylamino-1,3,5-triazine, 3-(3,4-dichlorophenyl)-1,1-dimethylurea; 3-
(3,4-dichlorophenyl)-methoxy-1-
Urea herbicides such as methylurea, 1-(2,2-dimethylbenzyl)-3-P-tolylurea,
Carbamate herbicides such as isopropyl-N-(3-chlorophenylcarbamate; methyl-N-(3,4-dichlorophenyl)carbamate, S
-(4-Chlorbenzyl)-N,N-diethylthiol carbamate; Thiol carbamate herbicides such as S-ethyl-N,N-hexamethylenethiol carbamate, 3,4-dichloropropionanilide; N-methoxymethyl- 2,6-diethyl-α-chloroacetanilide; 2-chloro-
2',6'-diethyl-N-(butoxymethyl)-acetanilide; N-chloroacetyl-N-(2,
Acid anilide herbicides such as 6-diethylphenyl)-glycine ethyl ester; uracil herbicides such as 5-bromo-3-secondary-butyl-6-methyluracil; 3-cyclohexyl-5,6-trimethyleneuracil; , 1,1'-dimethyl-4,4
- Pyridinium chlorine herbicides such as bispyridinium chloride, N,N-bis(phosphonomethyl)
-Glycine, O-ethyl-O-(2-nitro-5
-methylphenyl)-N-secondary butyl phosphoroamidothioate, S-(2-methyl-1
-Piperidylcarbonylmethyl)-O,O-di-
Phosphorous herbicides such as n-propyldithiophosphate, toluidine herbicides such as α,α,α-trifluoro-2,6-dinitro-N,N-dipropyl-P-toluidine, 5-tertiarybutyl-3
-(2,4-dichloro-5-isopropoxyphenyl)-1,3,4-oxadiazolin-2-one; 3-isopropyl-1H-2,1,3-benzothiadiazine-(4) -3H-one-2,2-dioxide, α(β-naphthoxy)-propionanilide, 4-(2,4-dichlorobenzoyl)-
Examples include, but are not limited to, 1,3-dimethylpyrazol-5-yl p-toluenesulfonate. Furthermore, the composition of the present invention can be used in combination with insecticides, nematicides, fungicides, plant growth regulators, fertilizers, etc., if necessary. Next, a production example of a compound represented by the general formula [] will be shown as a reference example. Reference example 1 (Production method A) After dissolving 690 mg of sodium hydroxide in 40 ml of water, 2.5 ml of 2-amino-3-chlorothiophenol
Dissolve g and add 2.4 g of bromoacetic acid while stirring. After stirring at 70°C for 3 hours, the precipitated crystals were filtered, washed with water, and dried to obtain the desired 5-chloro-2,3-dihydro-1,4-benzothiazine.
3-on m.p 160-161°C) 2.98 g was obtained.
【表】
参考例2 (製造法A)
2―アミノ―3―クロロチオフエノールの亜鉛
塩2.0gを水30mlに懸濁した中ヘブロム酢酸1.6g
を加え、70℃で3時間撹拌した。析出した結晶を
ろ過後、水洗し、乾燥して目的とする5―クロロ
―2,3―ジヒドロ―1,4―ベンゾチアジン―
3―オン(m.p160〜161℃)1.8gを得た。[Table] Reference Example 2 (Production method A) 1.6 g of hebromoacetic acid in which 2.0 g of zinc salt of 2-amino-3-chlorothiophenol was suspended in 30 ml of water.
was added and stirred at 70°C for 3 hours. After filtering the precipitated crystals, they are washed with water and dried to obtain the desired 5-chloro-2,3-dihydro-1,4-benzothiazine-
1.8 g of 3-one (m.p 160-161°C) was obtained.
【表】
参考例3 (製造法B)
2―アミノ―3―ブロモチオフエノール2.0g
とピリジン1.7gとを20mlのベンゼンに溶解し、
撹拌しながら室温(25℃)でクロロアセチルクロ
ライド1.2gを徐々に滴下した。滴下後加熱し、
80℃で5時間撹拌した後、冷時ろ過し、溶媒を留
去して得られた残渣をクロロホルムから再結晶し
て目的とする5―ブロモ―2,3―ジヒドロ―
1,4―ベンゾチアジン―3―オン(mp.146〜
147℃)2.0gを得た。[Table] Reference example 3 (Production method B) 2-amino-3-bromothiophenol 2.0g
and 1.7 g of pyridine are dissolved in 20 ml of benzene,
While stirring, 1.2 g of chloroacetyl chloride was gradually added dropwise at room temperature (25°C). After dropping, heat
After stirring at 80°C for 5 hours, it was filtered while cold, and the solvent was distilled off. The resulting residue was recrystallized from chloroform to obtain the desired 5-bromo-2,3-dihydro-
1,4-Benzothiazin-3-one (mp.146~
147°C) 2.0g was obtained.
【表】
参考例4 (製造法C)
2規定の水酸化ナトリウム水溶液中に2―クロ
ロアセチルアミノ―3―フルオロチオフエノール
2.0gを加え、室温(25℃)で3時間撹拌した
後、析出した結晶をろ過し、水洗後、乾燥して目
的とする5―フルオロ―2,3―ジヒドロ―1,
4―ベンゾチアジン―3―オン(mp.190〜191
℃)1.5gを得た。[Table] Reference Example 4 (Production method C) 2-chloroacetylamino-3-fluorothiophenol in 2N aqueous sodium hydroxide solution
After adding 2.0 g and stirring at room temperature (25°C) for 3 hours, the precipitated crystals were filtered, washed with water, and dried to obtain the desired 5-fluoro-2,3-dihydro-1,
4-Benzothiazin-3-one (mp.190-191
℃) 1.5g was obtained.
【表】
参考例5 (製造法D)
ピリジン5ml中に5―クロロ―2,3―ジヒド
ロ―1,4―ベンゾチアジン―3―オン2.0gと
五硫化リン2.0gを加え、120℃で20分間撹拌した
後50mlのの希塩酸中にあけ、析出する結晶をろ
過、水洗し、乾燥後エタノールから再結晶して目
的とする5―クロロ―2,3―ジヒドロ―1,4
―ベンゾチアジン―3―チオン(mp.138〜140
℃)1.9gを得た。[Table] Reference Example 5 (Production method D) Add 2.0 g of 5-chloro-2,3-dihydro-1,4-benzothiazin-3-one and 2.0 g of phosphorus pentasulfide to 5 ml of pyridine and heat at 120°C for 20 minutes. After stirring, pour into 50ml of diluted hydrochloric acid, filter the precipitated crystals, wash with water, dry and recrystallize from ethanol to obtain the desired 5-chloro-2,3-dihydro-1,4.
-Benzothiazine-3-thione (mp.138-140
℃) 1.9g was obtained.
【表】
次に実施例をあげ本発明をさらに詳細に説明す
る。なお、化合物名は前記例示の番号によつて示
す。
実施例1 畑地播種後土壌処理試験
3寸素焼植木鉢にメヒシバ、アオビユ、アカザ
の雑草種子とダイズ、ヒマワリの作物種子を播種
し、覆土後、所定量の原体を乳剤にし、水で希釈
し、ハンドスプレーヤーにて土壌処理した。その
後、温室内にて育成し、処理後20日目に除草効
力、作物薬害を観察し、その結果を第2表に示
す。除草効力の評価は下記のように0〜5の数字
で表わした。ただし、作物の薬害も除草効力と同
じ基準で示してある。
0……抑草率 0〜 9%
1…… 〃 10〜29%
2…… 〃 30〜49%
3…… 〃 50〜69%
4…… 〃 70〜89%
5…… 〃 90〜100%[Table] Next, the present invention will be explained in more detail with reference to Examples. In addition, the compound name is shown by the number of the said example. Example 1 Soil treatment test after sowing in upland field Weed seeds of crabgrass, blueberry, and pigweed and crop seeds of soybean and sunflower were sown in 3-dimensional bisque pots, and after covering with soil, a predetermined amount of the raw material was made into an emulsion, diluted with water, The soil was treated with a hand sprayer. Thereafter, the plants were grown in a greenhouse, and 20 days after treatment, the herbicidal efficacy and crop damage were observed. The results are shown in Table 2. Evaluation of herbicidal efficacy was expressed as a number from 0 to 5 as shown below. However, phytotoxicity of crops is also shown using the same criteria as herbicidal efficacy. 0... Weed suppression rate 0-9% 1... 10-29% 2... 30-49% 3... 50-69% 4... 70-89% 5... 90-100%
【表】
実施例 2
水田土壌1.5Kgずつ詰めた直径14cmのワグネル
ポツトを水田状態にし、3葉期の稲苗を移植し、
さらに稗種子を播種し、ウリカワ、ミズガヤツリ
の塊茎を植え付け、これに所定量の薬剤を湛水土
壌処理した。薬剤処理後25日目に前記移植または
播種植付けした植物および自然発生したコナギ、
アゼナ、キカシグサなどの広葉雑草について除草
効力、薬害の程度を調査した。その結果を第3表
に示す。
なお、処理方法については、所定量の薬剤を水
和剤の型でポツト当り15c.c.処理した。処理に際し
てはピペツトにて滴下した。除草効力の評価は下
記のように0〜5の数字で表わした。
0……抑草率 0〜 9%
1…… 〃 10〜29%
2…… 〃 30〜49%
3…… 〃 50〜69%
4…… 〃 70〜89%
5…… 〃 90〜100%
薬害に関しては、草丈、分げつ数、全量(風乾
重)の対無処理区比を出し、3つの要因のもつと
も値の悪いものをとつて0〜5で評価した。
0……対無処理区比 100%
1…… 〃 90〜99%
2…… 〃 80〜89%
3…… 〃 60〜79%
4…… 〃 40〜59%
5…… 〃 0〜39%[Table] Example 2 A Wagner pot with a diameter of 14 cm filled with 1.5 kg of paddy soil was turned into a paddy field, and rice seedlings at the 3-leaf stage were transplanted.
Furthermore, Japanese mulberry seeds were sown, and tubers of Japanese cypress and Cyperus japonica were planted, and a predetermined amount of the chemical was applied to the flooded soil. 25 days after drug treatment, the transplanted or sown plants and naturally occurring coryza;
We investigated the herbicidal efficacy and degree of chemical damage for broad-leaved weeds such as azalea and azalea. The results are shown in Table 3. Regarding the treatment method, a predetermined amount of the drug was treated in the form of a wettable powder at a rate of 15 c.c. per pot. During the treatment, the solution was added dropwise using a pipette. Evaluation of herbicidal efficacy was expressed as a number from 0 to 5 as shown below. 0... Weed suppression rate 0-9% 1... 10-29% 2... 30-49% 3... 50-69% 4... 70-89% 5... 90-100% Plant damage Regarding plant height, number of tillers, and total amount (air-dry weight), the ratio of plant height to the untreated plot was calculated, and the worst value among the three factors was taken and evaluated on a scale of 0 to 5. 0... Ratio to untreated area 100% 1... 〃 90-99% 2... 〃 80-89% 3... 〃 60-79% 4... 〃 40-59% 5... 〃 0-39%
【表】【table】
【表】
実施例 3
たて35cm、よこ25cm、高さ10cmのプラスチツク
トレーに畑地土壌を詰め、アオビユ、アカザ、メ
ヒシバおよびヒエを播種し、温室内で14日間育生
したあと所定量の薬剤を植物体の上方から小型噴
霧器で茎葉処理した。処理時における各植物の生
育状況は、アオビユ、アカザは草丈2〜6cm、メ
ヒシバ、ヒエは草丈4〜10cmであつた。
薬剤処理後さらに20日間温室内に置き、各植物
について除草効力を調査した。その結果を第4表
に示す。調査時に枯れ残つた植物の地上部を刈り
取つて生産量をはかり、無処理区の重量を100%
として残草率を計算して下記の基準により除草効
力を評価した。なお、処理薬剤は水和剤に製剤し
た所定量の薬剤を1アールあたり3の水に分散
させ、展着剤を加えて供試した。[Table] Example 3 A plastic tray measuring 35 cm in length, 25 cm in width, and 10 cm in height was filled with field soil, and seeds of blueberry, pigweed, red-winged grass, and barnyard grass were sown, and after growing in a greenhouse for 14 days, a prescribed amount of chemicals were applied to the plants. The leaves were treated with a small sprayer from above the body. The growth status of each plant at the time of treatment was 2 to 6 cm in plant height for the Japanese amberjack and pigweed, and 4 to 10 cm in plant height for the Japanese barley and Japanese barnyard grass. After the chemical treatment, the plants were kept in a greenhouse for another 20 days, and the herbicidal efficacy of each plant was investigated. The results are shown in Table 4. At the time of the survey, the above-ground parts of the plants that remained withered were harvested to measure the production volume, and the weight of the untreated area was 100%.
The herbicidal efficacy was evaluated according to the following criteria by calculating the remaining weed percentage. The processing agent was prepared by dispersing a predetermined amount of the agent in a wettable powder in 3 parts of water per are, and adding a spreading agent.
【表】【table】
Claims (1)
原子またはイオウ原子を表わす。〕 で示される1,4―ベンゾチアジン誘導体を有効
成分として含有することを特徴とする除草剤。[Claims] 1. General formula [In the formula, X represents a halogen atom, and Y represents an oxygen atom or a sulfur atom. ] A herbicide characterized by containing a 1,4-benzothiazine derivative represented by the following as an active ingredient.
Priority Applications (9)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP4576678A JPS54145678A (en) | 1978-04-17 | 1978-04-17 | Benzothiadiazine derivative, its preparation, and herbicides comprising it |
US06/028,801 US4268301A (en) | 1978-04-17 | 1979-04-10 | 1,4-Benzothiazines |
GB7912969A GB2018754B (en) | 1978-04-17 | 1979-04-12 | 1,4-benzothiazine derivatives and aminothiophenol derivatives and aminothiopehnol derivatives and their production and use |
NL7902937A NL7902937A (en) | 1978-04-17 | 1979-04-12 | BENZOTHIAZINE DERIVATIVES. |
FR7909477A FR2434160A1 (en) | 1978-04-17 | 1979-04-13 | PROCESS FOR THE PRODUCTION OF NOVEL 1,4-BENZOTHIAZINE DERIVATIVES AND THEIR INTERMEDIATES, AND HERBICIDES CONTAINING SUCH COMPOUNDS |
IN382/CAL/79A IN150554B (en) | 1978-04-17 | 1979-04-17 | |
DE19792915406 DE2915406A1 (en) | 1978-04-17 | 1979-04-17 | ACTIVE SUBSTANCES AND PROCESS FOR THEIR PRODUCTION |
PH22392A PH15954A (en) | 1978-04-17 | 1979-04-17 | 1,4-benzothiazine derivatives and their composition and method of use |
US06/200,339 US4337357A (en) | 1978-04-17 | 1980-10-24 | Herbicidal dithio-bis(haloacetanilides) |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP4576678A JPS54145678A (en) | 1978-04-17 | 1978-04-17 | Benzothiadiazine derivative, its preparation, and herbicides comprising it |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP10133186A Division JPS6248673A (en) | 1986-04-30 | 1986-04-30 | Benzothiazine derivative and production thereof |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS54145678A JPS54145678A (en) | 1979-11-14 |
JPS6250444B2 true JPS6250444B2 (en) | 1987-10-24 |
Family
ID=12728405
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP4576678A Granted JPS54145678A (en) | 1978-04-17 | 1978-04-17 | Benzothiadiazine derivative, its preparation, and herbicides comprising it |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS54145678A (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106795318B (en) | 2014-08-12 | 2020-07-14 | 飞利斯有限公司 | Molecular and polymeric semiconductors and related devices |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS4910671A (en) * | 1972-05-24 | 1974-01-30 |
-
1978
- 1978-04-17 JP JP4576678A patent/JPS54145678A/en active Granted
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS4910671A (en) * | 1972-05-24 | 1974-01-30 |
Also Published As
Publication number | Publication date |
---|---|
JPS54145678A (en) | 1979-11-14 |
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