JPH03284678A - Benzothiazolone derivative and herbicide - Google Patents
Benzothiazolone derivative and herbicideInfo
- Publication number
- JPH03284678A JPH03284678A JP8312090A JP8312090A JPH03284678A JP H03284678 A JPH03284678 A JP H03284678A JP 8312090 A JP8312090 A JP 8312090A JP 8312090 A JP8312090 A JP 8312090A JP H03284678 A JPH03284678 A JP H03284678A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- japanese
- parts
- water
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 21
- 239000004009 herbicide Substances 0.000 title claims abstract description 8
- BXQNSPXDWSNUKE-UHFFFAOYSA-N 1,3-benzothiazole 1-oxide Chemical class C1=CC=C2S(=O)C=NC2=C1 BXQNSPXDWSNUKE-UHFFFAOYSA-N 0.000 title claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 4
- 239000004480 active ingredient Substances 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 abstract description 26
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract description 12
- 239000002904 solvent Substances 0.000 abstract description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 abstract description 6
- 238000009835 boiling Methods 0.000 abstract description 3
- 239000000463 material Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 239000000203 mixture Substances 0.000 description 19
- 239000002689 soil Substances 0.000 description 15
- 238000009472 formulation Methods 0.000 description 13
- 241000196324 Embryophyta Species 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 244000058871 Echinochloa crus-galli Species 0.000 description 9
- -1 acetonitrile Chemical compound 0.000 description 9
- 241000218691 Cupressaceae Species 0.000 description 8
- 239000004563 wettable powder Substances 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000004033 plastic Substances 0.000 description 5
- 229920003023 plastic Polymers 0.000 description 5
- 244000025254 Cannabis sativa Species 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 240000007594 Oryza sativa Species 0.000 description 4
- 235000007164 Oryza sativa Nutrition 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 235000004405 Ageratum conyzoides Nutrition 0.000 description 3
- 235000008495 Chrysanthemum leucanthemum Nutrition 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- 241000219146 Gossypium Species 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 240000000486 Lepidium draba Species 0.000 description 3
- 235000000391 Lepidium draba Nutrition 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 231100000674 Phytotoxicity Toxicity 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 235000021307 Triticum Nutrition 0.000 description 3
- 244000098338 Triticum aestivum Species 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 235000009566 rice Nutrition 0.000 description 3
- IHDKBHLTKNUCCW-UHFFFAOYSA-N 1,3-thiazole 1-oxide Chemical class O=S1C=CN=C1 IHDKBHLTKNUCCW-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- 241000234653 Cyperus Species 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 235000008247 Echinochloa frumentacea Nutrition 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 241000205407 Polygonum Species 0.000 description 2
- 244000292697 Polygonum aviculare Species 0.000 description 2
- 235000011158 Prunus mume Nutrition 0.000 description 2
- 244000018795 Prunus mume Species 0.000 description 2
- 240000001341 Reynoutria japonica Species 0.000 description 2
- 235000018167 Reynoutria japonica Nutrition 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 235000005324 Typha latifolia Nutrition 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 244000118869 coast club rush Species 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 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
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 235000002568 Capsicum frutescens Nutrition 0.000 description 1
- 240000008574 Capsicum frutescens Species 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 241000270722 Crocodylidae Species 0.000 description 1
- 241000234646 Cyperaceae Species 0.000 description 1
- 240000001879 Digitalis lutea Species 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
- 235000014716 Eleusine indica Nutrition 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 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 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical group O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 235000006386 Polygonum aviculare Nutrition 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 244000184734 Pyrus japonica Species 0.000 description 1
- 241000681978 Rhododendron japonicum Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 240000000851 Vaccinium corymbosum Species 0.000 description 1
- 235000003095 Vaccinium corymbosum Nutrition 0.000 description 1
- 235000017537 Vaccinium myrtillus Nutrition 0.000 description 1
- 241001148683 Zostera marina Species 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 235000021014 blueberries Nutrition 0.000 description 1
- 239000004067 bulking agent Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 235000011116 calcium hydroxide Nutrition 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 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
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- LNNWVNGFPYWNQE-GMIGKAJZSA-N desomorphine Chemical compound C1C2=CC=C(O)C3=C2[C@]24CCN(C)[C@H]1[C@@H]2CCC[C@@H]4O3 LNNWVNGFPYWNQE-GMIGKAJZSA-N 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 230000035784 germination Effects 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
- 230000000887 hydrating effect Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 1
- 230000002262 irrigation Effects 0.000 description 1
- 238000003973 irrigation Methods 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 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
Landscapes
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
【発明の詳細な説明】
(産業上の利用分野)
本発明は、新規なベンゾチアゾロン誘導体及びそれを有
効成分とする除草剤に関するものである。DETAILED DESCRIPTION OF THE INVENTION (Field of Industrial Application) The present invention relates to a novel benzothiazolone derivative and a herbicide containing the same as an active ingredient.
(従来の技術)
これまで、特開昭62−158276号公報等にベンゾ
チアゾロン誘導体が除Q゛剤の有効成分として用いうる
ことがば己軌さ才している、(発明が解決しようとする
課題)
しかし、これらの化合物は除草活性が不充分であったり
作物・雑草間の選択性に劣ったりすることから必ずしも
満足すべきものではない。(Prior Art) Until now, it has been reported in Japanese Unexamined Patent Publication No. 158276/1983 that benzothiazolone derivatives can be used as active ingredients of Q removers (Problems to be Solved by the Invention) ) However, these compounds are not necessarily satisfactory because their herbicidal activity is insufficient or their selectivity between crops and weeds is poor.
また近年、作物・雑草間の選択性、環境汚染を抑制する
ための高活性・低薬量化、農作業の省力化に必要な残効
性等を高次元でAmする除草剤が強く求められている、
これは、ベンゾチアゾロン3!!導体においても無関係
ではなく、より優れフニ薬剤の開発が望まれている。In addition, in recent years, there has been a strong demand for herbicides that have a high level of selectivity between crops and weeds, high activity and low dosage to suppress environmental pollution, and residual efficacy necessary for labor saving in agricultural work. ,
This is benzothiazolone 3! ! This is not unrelated to the field of conductors, and the development of better chemicals is desired.
(課題を解決するための手段)
本発明者らは上記の目的を達成するために数多くのベン
ゾチアゾロン誘導体を合成し、それらの有用性について
種々検討した。その結果、2H−イソインドール−1,
3−ジオン−2−イル基を5位の置換基としてもつベン
ゾチアゾロン誘導体が」二組の目的に適う優れた除草活
性と選択性を有すること詮見出し1本発明を完成するに
至った。(Means for Solving the Problems) In order to achieve the above object, the present inventors synthesized a number of benzothiazolone derivatives and conducted various studies on their usefulness. As a result, 2H-isoindole-1,
The present invention has been completed based on the finding that a benzothiazolone derivative having a 3-dione-2-yl group as a substituent at the 5-position has excellent herbicidal activity and selectivity that meet two objectives.
すなわち1本発明は一般式
一般式口〕で示される本発明化合物は、次の方法により
製造することができる。That is, the compound of the present invention represented by the general formula (1) can be produced by the following method.
(式中、Rはアルキル基、アルケニル基またはアルキニ
ル基を示す。)で示されるベンゾチアゾロン誘導体及び
それを有効成分とする除草剤を提供するものである。The present invention provides a benzothiazolone derivative represented by the formula (wherein R represents an alkyl group, an alkenyl group, or an alkynyl group) and a herbicide containing the derivative as an active ingredient.
次に2本発明化合物の具体的な例を第1表に示す、化合
物番号は以下の記載において参照される。Next, specific examples of the two compounds of the present invention are shown in Table 1, and the compound numbers are referred to in the following description.
第1表 〇
CD)[[[) 口〕
〔式中、Rは前記と同じ意味を示す、〕この方法は一数
式CI+)で表される化合物と一般式(III)で表さ
れる化合物とを反応させることにより行われる。Table 1 (CD) This is done by reacting.
溶媒としては、例えばヘキサン、ベンゼン、トルエンな
どの炭化水素類、ジオキサン、エチレングリコールジメ
チルエーテル、テトラヒドロフラン等のエーテル類、蟻
酸、酢酸等の脂肪酸類および水あるいはそれらの混合物
を使用することかできる。As the solvent, for example, hydrocarbons such as hexane, benzene and toluene, ethers such as dioxane, ethylene glycol dimethyl ether and tetrahydrofuran, fatty acids such as formic acid and acetic acid, water, or mixtures thereof can be used.
−F貫己の反応は60℃から溶媒の沸点の温度の範囲で
行い、1〜24時間で終了する0反応終了後に水を加え
、有機溶媒で抽出後に水で水洗、乾燥、濃縮等の後処理
を行い、必要に応じて再結晶、りロマトヅラフイー等の
操作によって精製することによって目的の本発明化合物
を得ることができる。The -F reaction is carried out at a temperature range from 60°C to the boiling point of the solvent, and is completed in 1 to 24 hours. After the completion of the reaction, water is added, extracted with an organic solvent, washed with water, dried, concentrated, etc. The desired compound of the present invention can be obtained by treatment and, if necessary, purification by operations such as recrystallization and chromatography.
尚、原料である一般式(11)で表される化合物は、以
下の方法により製造することができる。In addition, the compound represented by general formula (11) which is a raw material can be manufactured by the following method.
〔■〕 〔口〕〔式中、丁くは
前記と同じ意味を示す、〕この方法は一般式[IV)で
表される化合物に還元剤を使用して還元することによっ
て行われる。[■] [In the formula, "C" has the same meaning as above] This method is carried out by reducing the compound represented by the general formula [IV] using a reducing agent.
還元剤としては、鉄、スズ2亜釦などの金属類を使用で
きる。As the reducing agent, metals such as iron and tin oxide can be used.
溶媒としては酢酸、塩酸などの酸類、酢酸エチル、酢酸
ブチルなどの脂肪族エステル類、トルエン、キシレン、
ベンゼンなどの芳香族炭化水素類。Examples of solvents include acids such as acetic acid and hydrochloric acid, aliphatic esters such as ethyl acetate and butyl acetate, toluene, xylene,
Aromatic hydrocarbons such as benzene.
メチルアルコール、エチルアルコールなどのアルコール
類またはそれらの混合物があげられる。Examples include alcohols such as methyl alcohol and ethyl alcohol, or mixtures thereof.
上記の反応は、0℃から溶媒の沸点の温度の範囲で行い
、1〜24時間で終rする。The above reaction is carried out at a temperature ranging from 0° C. to the boiling point of the solvent, and is completed in 1 to 24 hours.
尚、原料である一般式[IV)で表される化合物は、以
下の方法により製合することができる7(V〕(VI)
[I’%)]
〔式中、Rは前記と同し、意味を表す。〕この方法は一
般式EV)で表される化合物と線式〔■〕で表される化
合物とを塩基の存在下で反応させることによって行われ
る。In addition, the compound represented by the general formula [IV], which is a raw material, can be prepared by the following method: 7(V)(VI)
[I'%)] [In the formula, R has the same meaning as above. ] This method is carried out by reacting a compound represented by the general formula EV) with a compound represented by the linear formula [■] in the presence of a base.
この反応は、通常、無溶媒または溶媒中において説ハロ
ゲン水素化剤の存在下で行う。反応温度の範囲は一50
〜100℃、反応時間の範囲は10分〜24時間であり
、反応に供される試剤の量はチアゾロン誘導体〔v〕1
当量に対して化合物(Vl)は1〜1.5当量である。This reaction is usually carried out without a solvent or in a solvent in the presence of a halogenated hydrogenating agent. The reaction temperature range is -50
~100°C, the reaction time ranges from 10 minutes to 24 hours, and the amount of reagent used for the reaction is 1 ml of thiazolone derivative [v]
The amount of compound (Vl) is 1 to 1.5 equivalents.
溶媒としてはベンゼン、トルエン、キシレン。Benzene, toluene, and xylene are used as solvents.
等の芳香族炭化水素類、ジオキサン、テトラヒドロフラ
ン、ジエチレングリコールジメチルエーテル等のエーテ
ル類、アセトニトリル、インブチロニトリル等のニトリ
ル類、ホルムアミド、 N、N−ジメチルホルムアミド
、アセトアミド等の酸アミド、ジメチルスルホキシド、
スルホラン等の硫黄化合物および水など、あるいはそれ
らの混合物があげられる。Aromatic hydrocarbons such as dioxane, tetrahydrofuran, diethylene glycol dimethyl ether, nitriles such as acetonitrile, imbutyronitrile, acid amides such as formamide, N,N-dimethylformamide, acetamide, dimethyl sulfoxide,
Examples include sulfur compounds such as sulfolane, water, and mixtures thereof.
塩基としてはナトリウム、カリウム、水酸化ナトリウム
、水酸化カリウム、炭酸ナトリウム、炭酸カリウム、水
素化ナトリウム等の無機塩基があげられる0反応終了後
の反応液は、水を加え、有機溶媒抽出および濃縮等の通
常の操作を行い、必要ならばグロマトグラフィー、再結
晶等の操作で精製することによって製造できる。Examples of the base include inorganic bases such as sodium, potassium, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, and sodium hydride. After the reaction is complete, water is added to the reaction solution, and the reaction solution is extracted with an organic solvent, concentrated, etc. It can be produced by carrying out the usual operations and, if necessary, purifying it by operations such as chromatography and recrystallization.
尚、原料である一般式(V)で表される化合物はゴジシ
ニク バソフィスキャユニバシテートキミゲスキ ファ
クルテート (God、 5ofij、 []niv。In addition, the compound represented by the general formula (V) which is a raw material is God, 5ofij, []niv.
、Whit Fak、)67.287−293 (
1976)等に記載の方法により製造することができる
。, Whit Fak, ) 67.287-293 (
1976) and others.
実施例 2−(3−(2−プロピニル)−2(3H)−
ベンゾチアゾロン−5−イル〕
4.5.6.7−チトラヒドロインインドールー1,3
−ジオン(化合物5)の製法ジムロートを付した反応フ
ラスコに5−アミノ−3(2−プロピニル)−2(3H
)−ベンゾチアゾロン0.30g (1,5mmo 1
)、4.5゜6.7−テトラヒドロ無水フタル酸 0.
22 g(1,5mmol)、酢酸1.0mΩを入れ、
2時間加熱還流を行い1反応を終了とした。その後。Example 2-(3-(2-propynyl)-2(3H)-
Benzothiazolone-5-yl] 4.5.6.7-thitrahydroinindole 1,3
-Production of Dione (Compound 5) 5-Amino-3(2-propynyl)-2(3H) was added to a reaction flask equipped with a Dimroth.
)-benzothiazolone 0.30g (1.5mmo 1
), 4.5°6.7-tetrahydrophthalic anhydride 0.
Add 22 g (1.5 mmol) and 1.0 mΩ of acetic acid,
One reaction was completed by heating under reflux for 2 hours. after that.
反応液に水を加え、酢酸エチルで抽出後に水洗、乾燥、
濃縮を行って組成物を得た。この組成物にシリカゲルク
ロマトグラフィーで精製して目的化合物である2−[3
−(2−プロピニル)−2(3H)−ベンゾチアゾロン
−5−イル)−4、56,7−チトラヒドロイソインド
ール0.25 g(収率=49%)を得た。Add water to the reaction solution, extract with ethyl acetate, wash with water, dry,
Concentration was performed to obtain a composition. This composition was purified by silica gel chromatography to obtain the target compound 2-[3
0.25 g (yield = 49%) of -(2-propynyl)-2(3H)-benzothiazolon-5-yl)-4,56,7-titrahydroisoindole was obtained.
融点 206〜209℃。Melting point: 206-209°C.
本発明の除草剤は一般式([)で示されるベンゾチアゾ
ロン誘導体を有効成分としてなる。The herbicide of the present invention contains a benzothiazolone derivative represented by the general formula ([) as an active ingredient.
本発明化合物を除草剤として水田、畑地、4!!園地、
非農耕地等に使用する場合、その目的に応じて有効成分
を適当な剤型で用いることができる。Use the compound of the present invention as a herbicide in paddy fields, upland fields, 4! ! garden,
When used on non-agricultural land, the active ingredient can be used in an appropriate dosage form depending on the purpose.
通常の場合は有効成分を不活性な液体または固体の担体
で希釈し、必要に応じて界面活性剤、分散剤、補助剤等
を配合して、粉剤、水和剤、乳剤、粒剤等の各種形態に
製剤して使用することができる。製剤化に際して用いら
れる担体としては、例°えばジ−クライト、タルク、ベ
ン1−ナイト、クレー、カオリン、珪藻土、ホワイトカ
ーボン、バーミキュライト、消石灰、珪砂、硫安5尿素
等の固体担体、イソプロピルアルコール、キシレン、シ
クロヘキサノン、メチルナフタレン等の液体担体等があ
げられる。界面活性剤及び分散剤としては、例えばアル
コール硫酸エステル塩、アルキルアリールスルホン酸塩
、リグニンスルホン酸塩、ポリオキシエチレングリコー
ルエーテル、ポリオキシエチレンアルキルアリールエー
テル、ポリオキシエチレンソルビタンモノアルキレート
等があげられる。補助剤としては1例えばカルボキシメ
チルセルロース、ポリエチレングリコール、アラビアゴ
ム等があげられる。使用に際しては、適当な濃度に希釈
して散布するかまたは直接施用する。その施用量は適用
の場面と時期、施用方法、栽培作物笠により差異がある
が一般には本発明化合物の有効成分で10アール当り0
.1g−IKg、施用する。In normal cases, the active ingredient is diluted with an inert liquid or solid carrier, and if necessary, surfactants, dispersants, adjuvants, etc. are added to form powders, wettable powders, emulsions, granules, etc. It can be formulated and used in various forms. Examples of carriers used in formulation include solid carriers such as gicrite, talc, ben-1-night, clay, kaolin, diatomaceous earth, white carbon, vermiculite, slaked lime, silica sand, ammonium sulfate pentaurea, isopropyl alcohol, and xylene. , cyclohexanone, methylnaphthalene, and the like. Examples of surfactants and dispersants include alcohol sulfate salts, alkylaryl sulfonates, lignin sulfonates, polyoxyethylene glycol ethers, polyoxyethylene alkylaryl ethers, and polyoxyethylene sorbitan monoalkylates. . Examples of adjuvants include carboxymethylcellulose, polyethylene glycol, gum arabic, and the like. When used, it can be diluted to an appropriate concentration and sprayed, or applied directly. The amount of application varies depending on the occasion and timing of application, application method, and cultivated crop shade, but in general, the active ingredient of the compound of the present invention is 0 per 10 ares.
.. 1 g-IKg, apply.
次に代表的な製剤例をあげて製剤方法を具体的に説明す
る。以下の説明において1部」は重量部を意味する。Next, the formulation method will be specifically explained using typical formulation examples. In the following description, "1 part" means part by weight.
製剤例1 水和剤
化合物(3)の10部にエマルゲン810(花王株式会
社の登録商標)の0 、5 !g、デ干−ルN(花王株
式会社の登録商標)の05部、クニライト201 (ク
ニミネ工業株式会社の登録商標)の20部、ジ−クライ
トCA(ジ−クライト株式会社の登録商標)の69部を
混合粉砕し、水和剤を得る。Formulation Example 1 10 parts of wettable powder compound (3) and 0.5 parts of Emulgen 810 (registered trademark of Kao Corporation)! g, 05 parts of De-Hanru N (registered trademark of Kao Corporation), 20 parts of Kunilite 201 (registered trademark of Kunimine Industries Co., Ltd.), 69 parts of Zeekrite CA (registered trademark of Zeekrite Co., Ltd.) Mix and grind the parts to obtain a wettable powder.
製剤例2 水和剤
化合物(2)の】0部にエマルゲン810の0゜5部、
デモールNの0.5部、ダニライト20ユの20部、カ
ープレックス80の5部、ジ−クライトCAの64部を
混合粉砕し、水和剤を得る。Formulation Example 2 0 parts of wettable powder compound (2), 5 parts of Emulgen 810,
0.5 parts of Demol N, 20 parts of Danilite 20 U, 5 parts of Carplex 80, and 64 parts of Zeekrite CA are mixed and ground to obtain a wettable powder.
製剤例3 乳剤
化合物(1)の30部にキシレンとイソホロンの等景況
合物60部、界面活性剤ツルポール800A(東邦化学
工業株式会社の登録部l1l)の10部を加え、これら
kよくかきまぜることによって乳剤を得る。Formulation Example 3 To 30 parts of emulsion compound (1), add 60 parts of a compound of xylene and isophorone and 10 parts of the surfactant Tsurupol 800A (registered part of Toho Chemical Industry Co., Ltd.), and stir these thoroughly. An emulsion is obtained by
製剤例4 粒剤
化合物(4)の10部、タルクとベントナイトを】=3
の割合の混合した増量剤の80部、ホワイトカーボンの
5部2界面活性剤ツルポール800Aのの5部に水10
部を加え、よく練ってペースト状としたものを直径0
、7 amのふるい穴から押し出して乾燥した後に05
〜1■の長さに切断し、粒剤を得る。Formulation Example 4 10 parts of granule compound (4), talc and bentonite]=3
80 parts of bulking agent, 5 parts of white carbon, 2 parts of surfactant Tsurupol 800A, 10 parts of water
Add 100% of
, 05 after extruding through the sieve hole at 7 am and drying.
Cut into ~1 inch length to obtain granules.
(発明の効果)
一般式(1)で表される本発明の化合物は、水田に発生
するヒエ、タマガヤツリ、コナギ、キカシグサ、アゼナ
等の一年生雑草及びホタルイ、ヘラオモダカ、ミズガヤ
ツリ等の多年生雑草の発芽時から生育期の広い範囲にわ
たって、極めて低い薬量で優れた除草効果な発揮すると
同時に、水稲に対しては高い安全性を有するものである
。また、畑地においても問題となる種々の雑草、例えば
タデ、アオビユ、シロザ、イチビ等の広葉雑草をはじめ
、カヤツリグサ、コゴメガヤツリ等のカヤツリグサ科雑
草、ヒエ、メヒシバ、エノコログサ2ジヨンソングラス
、ノスズメノテッポウ等のイネ科雑草に対して、土壌処
理あるいは茎葉処理で高い除草効果を示すと同時に、大
豆、棉5 トウモロコシ2陸稲、小麦等に対しては高い
安全性を示すという特徴を有するものである。また、樹
園地、牧草地、芝生地及び非農耕地等に用いることもで
きる。(Effects of the Invention) The compound of the present invention represented by the general formula (1) can be used during the germination of annual weeds such as Japanese barnyard grass, Japanese cypress, Japanese cypress, Japanese cypress, Japanese azalea, etc., and perennial weeds such as bulrush, Japanese cypress, and Japanese cypress, which occur in rice fields. It exhibits excellent herbicidal effects at extremely low dosages over a wide range of the growing season, and at the same time is highly safe for paddy rice. In addition, various weeds that can be a problem in fields, such as broad-leaved weeds such as polygonum, Japanese apricot, whiteweed, and Japanese crocodile, as well as weeds of the Cyperaceae family such as cyperus cyperus and cyperus japonica, Japanese barnyard grass, red foxtail grass, foxglove grass, and staghorn grass, etc. It exhibits a high herbicidal effect against grass weeds when treated with soil or foliage, and at the same time is highly safe against soybeans, cotton, corn, upland rice, wheat, etc. It can also be used in orchards, pastures, lawns, non-agricultural lands, etc.
次に試験例をあげて本発明化合物の奏する効果を説明す
る。Next, the effects of the compounds of the present invention will be explained by giving test examples.
試験例】、(水田土壌処理による除草効果試験)100
rm’のプラスチックポットに水田土壌シ充填し、代掻
後、タイヌビエ、タマガヤツリ、コナギ及びホタルイの
各種子を播種し、水深3cmに湛水した。翌日、製剤例
1に準じてtil製した水和剤を水で希釈し、水面に滴
下処理した。施用量は、有効成分咎】0アール当り10
0gとした。その後、温室内で育成し、処理21日1に
第2表の基準に従い、除草効果を調査した。その結果を
第3表に示した、
第2表
第3表
試験例2(畑地茎葉処理による除草効果試験)120
cm2プラスチックポットに畑地土壌を充填し、タデ、
アオビユ、シロザ、コゴメガヤッリの各種子を播種し、
ヒエが3葉期になるまで温室内で育成した。ヒエの3葉
期に製剤例1に辛しでgl!II2シた水和剤を水に希
釈し、joアール当り有効成分が400gになる様に、
10アール当り100flを小型噴霧器で植物体の上方
から全体に茎葉散布処理した。その後、温室内で育成し
、処理21日1に第2表の基準に従って、除草効果を調
査した。その結果を第4表Lコ示す。Test example], (herbicidal effect test by paddy soil treatment) 100
rm' plastic pots were filled with paddy soil, and after puddling, seeds of Japanese millet, Japanese cypress, Japanese cypress, and bulrush were sown, and the pots were submerged in water to a depth of 3 cm. The next day, a wettable powder prepared in a til format according to Formulation Example 1 was diluted with water and dropped onto the water surface. The application amount is 10 per active ingredient
It was set to 0g. Thereafter, the plants were grown in a greenhouse, and the herbicidal effect was investigated on the 21st day of treatment according to the standards in Table 2. The results are shown in Table 3, Table 2 Table 3 Test Example 2 (Herbicidal effect test by field soil foliage treatment) 120
Fill a cm2 plastic pot with field soil and plant knotweed,
Seeds of Aobiyu, Shiroza, and Kogomegayari were sown.
The barnyard grass was grown in a greenhouse until it reached the three-leaf stage. At the 3-leaf stage of Japanese barnyard grass, add hot pepper to Formulation Example 1! Dilute the wettable powder with water so that the active ingredient is 400g per cup.
A small sprayer was used to spray 100 fl/10 are over the entire plant from above. Thereafter, the plants were grown in a greenhouse, and the herbicidal effect was investigated on the 21st day of treatment according to the standards in Table 2. The results are shown in Table 4.
第4表
第5表
試験例3(畑地土壌処理による除草効果試験)120c
謹2プラスチツクポツトに畑地土壌を充填し、ヒエ、メ
ヒシバ、タデ、アオビユ、シロザ、コゴメガヤツリの各
種子を播種して覆土した。製剤例1に準じて調製した水
和剤を水で希釈し。Table 4 Table 5 Test Example 3 (Herbicidal effect test by field soil treatment) 120c
Two plastic pots were filled with upland soil, and seeds of Japanese millet, Japanese knotweed, Japanese knotweed, Japanese violet, Japanese whiteberry, and Japanese cypress were sown and covered with soil. A wettable powder prepared according to Formulation Example 1 was diluted with water.
10アール当り有効成分が100gになる様に、10ア
ール当り1oOQを小型噴霧器で土壌表面に均一に散布
した。その後、温室内で育成し、処理21日l1第2表
の基準に従って、除草効果を調査した、その結果を第5
表に示す。1oOQ per 10 ares was uniformly sprayed on the soil surface using a small sprayer so that the active ingredient was 100 g per 10 ares. After that, it was grown in a greenhouse, and the herbicidal effect was investigated according to the standards in Table 2 after 21 days of treatment.
Shown in the table.
試験例4(水田土壌処理による薬効、薬害試験)1 /
5000 aワグネルボソトに水田土壌を充填し、入
水、代掻後、ヒエ、コナギ、ホタルイ及びタマガヤツリ
の種子を播種し、さらに25葉期の水稲を移植深度2c
mで、2本2株移植して水深311に湛水した。!!日
、製剤例1に準じてrRsi!した水和剤の所定有効成
分量を水で希釈し、水面に滴下処理した。その後、温室
内で育成し、処理30日1に第2表の基準に従い、除草
効果及び薬害を調査した。その結果4第6表に示す。Test example 4 (medicinal efficacy and phytotoxicity test by paddy soil treatment) 1 /
Paddy soil was filled in a 5,000 a.
2 m, 2 plants were transplanted and submerged in water at a depth of 311 m. ! ! rRsi! according to Formulation Example 1. A predetermined amount of the active ingredient of the wettable powder was diluted with water and dropped onto the water surface. Thereafter, they were grown in a greenhouse, and on day 30 of treatment, their herbicidal effects and phytotoxicity were investigated according to the standards in Table 2. The results are shown in Table 6.
第6表
害を調査した。その結果を第7−A表及び第7−B表に
示す。We investigated Table 6 harm. The results are shown in Table 7-A and Table 7-B.
第7−A表
試験例5(畑地茎葉処理における作物選択性試験)60
0 cm”プラスチックポット各々に畑地土壌を充填し
、A:トウモロコシ、ツルガム、イチビ。Table 7-A Test Example 5 (Crop selectivity test in field stem and foliage treatment) 60
Fill each 0 cm" plastic pot with upland soil.
ノアサガオ、オナモミを、B:イネ、コムギ、タデ、ア
オビユ、シロザを播種した。ポット底部より吸水させ、
ヒエが3葉期になるまで温室内で育成した。ヒエの3葉
期に製剤例1に準じてg製した水利剤の所定有効成分量
を10アール当り100Qの水で希釈し、小型噴霧器で
土壌表面に散布処理した。その後、再び温室内で育成し
、処理21日l1第2表の基準に従って、除草効果及び
薬筒7
B表
試験N6(畑地土壌処理における作物選択性試験)60
0 cH’プラスチックポット各々に畑地土壌を充填し
、A:トウモロコシ、ダイズ、ワタ、ヒエ、メヒシバ、
ゴノコログザ、ジョンソングラスを、B:コムギ、ツル
ガム、ワタ、タデ、アオビユ、シロザ、イチビを播種し
た、ポット底部より吸水させた後、製剤例コに準じて調
製した水和剤の所定有効成分量を]0アール当り1OO
Qの水で希釈し、小型噴霧器で土壌表面に均一に散布し
た、その後再び温室内で育成し、処理2コ日目に第2表
の基準に従って除草効果及び薬害を調査した。その結果
を第8−A表及び第8−B表に示す。B: Rice, wheat, knotweed, blueberry, and whiteweed were sown. Absorb water from the bottom of the pot,
The barnyard grass was grown in a greenhouse until it reached the three-leaf stage. A predetermined amount of the active ingredient of an irrigation agent prepared in g according to Formulation Example 1 at the third leaf stage of Japanese barnyard grass was diluted with 100 Q of water per 10 are, and sprayed onto the soil surface using a small sprayer. After that, it was grown again in the greenhouse, and the herbicidal effect was determined according to the standards in Table 2 after 21 days of treatment.
0 cH' Fill each plastic pot with upland soil, A: corn, soybean, cotton, barnyard grass, crabgrass,
After absorbing water from the bottom of a pot in which B: wheat, turgsum, cotton, polygonum, Japanese apricot, whiteweed, and Japanese grass were sown, the predetermined amount of the active ingredient of the hydrating powder prepared according to Formulation Example C was added. ] 1OO per 0 are
It was diluted with water from Q and uniformly sprayed on the soil surface using a small sprayer. After that, it was grown again in the greenhouse, and on the second day of treatment, the herbicidal effect and phytotoxicity were investigated according to the standards in Table 2. The results are shown in Table 8-A and Table 8-B.
第8−A表 第8−B表Table 8-A Table 8-B
Claims (2)
ル基を示す。)で表されるベンゾチアゾロン誘導体。(1) A benzothiazolone derivative represented by the general formula ▲ Numerical formula, chemical formula, table, etc. ▼ (In the formula, R represents an alkyl group, an alkenyl group, or an alkynyl group.)
ル基を示す。)で表されるベンゾチアゾロン誘導体を有
効成分として含有する除草剤。(2) A herbicide containing as an active ingredient a benzothiazolone derivative represented by the general formula ▲ Numerical formula, chemical formula, table, etc. ▼ (In the formula, R represents an alkyl group, an alkenyl group, or an alkynyl group.)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP8312090A JPH03284678A (en) | 1990-03-30 | 1990-03-30 | Benzothiazolone derivative and herbicide |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP8312090A JPH03284678A (en) | 1990-03-30 | 1990-03-30 | Benzothiazolone derivative and herbicide |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH03284678A true JPH03284678A (en) | 1991-12-16 |
Family
ID=13793346
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP8312090A Pending JPH03284678A (en) | 1990-03-30 | 1990-03-30 | Benzothiazolone derivative and herbicide |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH03284678A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5719104A (en) * | 1994-04-08 | 1998-02-17 | E. I. Du Pont De Nemours And Company | Herbicidal bicyclic and tricyclic imides |
CN103664918A (en) * | 2013-12-20 | 2014-03-26 | 中国农业大学 | Tetralin isobenzazole-1,3-diketone substituent benzoxazolinone derivative |
-
1990
- 1990-03-30 JP JP8312090A patent/JPH03284678A/en active Pending
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5719104A (en) * | 1994-04-08 | 1998-02-17 | E. I. Du Pont De Nemours And Company | Herbicidal bicyclic and tricyclic imides |
CN103664918A (en) * | 2013-12-20 | 2014-03-26 | 中国农业大学 | Tetralin isobenzazole-1,3-diketone substituent benzoxazolinone derivative |
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