JPH041748B2 - - Google Patents
Info
- Publication number
- JPH041748B2 JPH041748B2 JP59198245A JP19824584A JPH041748B2 JP H041748 B2 JPH041748 B2 JP H041748B2 JP 59198245 A JP59198245 A JP 59198245A JP 19824584 A JP19824584 A JP 19824584A JP H041748 B2 JPH041748 B2 JP H041748B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- japanese
- compound
- parts
- soil
- 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
- 230000002363 herbicidal effect Effects 0.000 claims description 15
- 239000004009 herbicide Substances 0.000 claims description 10
- 239000004480 active ingredient Substances 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 6
- SPAMRUYRVYMHPV-UHFFFAOYSA-N 3a,4,5,7a-tetrahydroisoindole-1,3-dione Chemical class C1=CCCC2C(=O)NC(=O)C21 SPAMRUYRVYMHPV-UHFFFAOYSA-N 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
- 125000005081 alkoxyalkoxyalkyl group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- HMMBJOWWRLZEMI-UHFFFAOYSA-N 4,5,6,7-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1CCCC2=C1C(=O)OC2=O HMMBJOWWRLZEMI-UHFFFAOYSA-N 0.000 claims description 2
- RYDRNBPXKNIEAP-UHFFFAOYSA-N 4-amino-4h-1,2-benzoxazin-3-one Chemical class C1=CC=C2C(N)C(=O)NOC2=C1 RYDRNBPXKNIEAP-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 32
- 239000002689 soil Substances 0.000 description 24
- 241000196324 Embryophyta Species 0.000 description 21
- 238000011282 treatment Methods 0.000 description 20
- 239000000203 mixture Substances 0.000 description 19
- 239000000839 emulsion Substances 0.000 description 15
- 238000009472 formulation Methods 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- -1 pyrofluorite Substances 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 244000058871 Echinochloa crus-galli Species 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 240000007594 Oryza sativa Species 0.000 description 6
- 235000007164 Oryza sativa Nutrition 0.000 description 6
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 6
- 235000009566 rice Nutrition 0.000 description 6
- 244000025254 Cannabis sativa Species 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 240000003173 Drymaria cordata Species 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 235000005733 Raphanus sativus var niger Nutrition 0.000 description 4
- 235000006140 Raphanus sativus var sativus Nutrition 0.000 description 4
- 240000001970 Raphanus sativus var. sativus Species 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000004927 clay Substances 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 4
- 238000003892 spreading Methods 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- 241001311476 Abies veitchii Species 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
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 3
- 241000234646 Cyperaceae Species 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 240000001549 Ipomoea eriocarpa Species 0.000 description 3
- 235000005146 Ipomoea eriocarpa Nutrition 0.000 description 3
- 240000007218 Ipomoea hederacea Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 235000021307 Triticum Nutrition 0.000 description 3
- 244000098338 Triticum aestivum Species 0.000 description 3
- 239000001768 carboxy methyl cellulose Substances 0.000 description 3
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 3
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 230000012010 growth Effects 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 229910052814 silicon oxide Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000004094 surface-active agent 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
- 240000004731 Acer pseudoplatanus Species 0.000 description 2
- 235000002754 Acer pseudoplatanus Nutrition 0.000 description 2
- 235000004405 Ageratum conyzoides Nutrition 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- 240000001592 Amaranthus caudatus Species 0.000 description 2
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 2
- 235000007319 Avena orientalis Nutrition 0.000 description 2
- 241000209763 Avena sativa Species 0.000 description 2
- 235000007558 Avena sp Nutrition 0.000 description 2
- 235000008495 Chrysanthemum leucanthemum Nutrition 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
- 235000010469 Glycine max Nutrition 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 240000000486 Lepidium draba Species 0.000 description 2
- 235000000391 Lepidium draba Nutrition 0.000 description 2
- 229920001732 Lignosulfonate Polymers 0.000 description 2
- 244000064622 Physalis edulis Species 0.000 description 2
- 235000006485 Platanus occidentalis Nutrition 0.000 description 2
- 240000001341 Reynoutria japonica Species 0.000 description 2
- 235000018167 Reynoutria japonica Nutrition 0.000 description 2
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 2
- 244000062793 Sorghum vulgare Species 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 244000172533 Viola sororia Species 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
- 239000002253 acid Substances 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 2
- RYAGRZNBULDMBW-UHFFFAOYSA-L calcium;3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Ca+2].COC1=CC=CC(CC(CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O RYAGRZNBULDMBW-UHFFFAOYSA-L 0.000 description 2
- 229940125904 compound 1 Drugs 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
- 230000009931 harmful effect Effects 0.000 description 2
- 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 2
- 239000007788 liquid Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ZMESHQOXZMOOQQ-UHFFFAOYSA-N 1-(naphthalen-1-ylmethyl)naphthalene Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 ZMESHQOXZMOOQQ-UHFFFAOYSA-N 0.000 description 1
- SURCGQGDUADKBL-UHFFFAOYSA-N 2-(2-hydroxyethylamino)-5-nitrobenzo[de]isoquinoline-1,3-dione Chemical compound [O-][N+](=O)C1=CC(C(N(NCCO)C2=O)=O)=C3C2=CC=CC3=C1 SURCGQGDUADKBL-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-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
- VHRCRGJPHYNVGS-UHFFFAOYSA-N 6-amino-7-fluoro-4-prop-2-ynyl-1,4-benzoxazin-3-one Chemical compound C#CCN1C(=O)COC2=C1C=C(N)C(F)=C2 VHRCRGJPHYNVGS-UHFFFAOYSA-N 0.000 description 1
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 241000254032 Acrididae Species 0.000 description 1
- 241001621841 Alopecurus myosuroides Species 0.000 description 1
- 241000195967 Anthoceros Species 0.000 description 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
- 229910021532 Calcite Inorganic materials 0.000 description 1
- 241001335577 Ceratophyllum echinatum Species 0.000 description 1
- 241000282994 Cervidae Species 0.000 description 1
- 240000003538 Chamaemelum nobile Species 0.000 description 1
- 235000007866 Chamaemelum nobile Nutrition 0.000 description 1
- 235000005470 Chrysanthemum segetum Nutrition 0.000 description 1
- 244000144786 Chrysanthemum segetum Species 0.000 description 1
- 241000233838 Commelina Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 240000001879 Digitalis lutea Species 0.000 description 1
- 241000428981 Dyssodia Species 0.000 description 1
- 235000009419 Fagopyrum esculentum Nutrition 0.000 description 1
- 240000008620 Fagopyrum esculentum Species 0.000 description 1
- 235000014693 Fagopyrum tataricum Nutrition 0.000 description 1
- 241000219146 Gossypium Species 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 244000020551 Helianthus annuus Species 0.000 description 1
- 235000003222 Helianthus annuus Nutrition 0.000 description 1
- 241000258937 Hemiptera Species 0.000 description 1
- 240000007049 Juglans regia Species 0.000 description 1
- 235000009496 Juglans regia Nutrition 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 235000013939 Malva Nutrition 0.000 description 1
- 240000000982 Malva neglecta Species 0.000 description 1
- 235000000060 Malva neglecta Nutrition 0.000 description 1
- 235000007232 Matricaria chamomilla Nutrition 0.000 description 1
- 208000003351 Melanosis Diseases 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
- 244000234609 Portulaca oleracea Species 0.000 description 1
- 235000001855 Portulaca oleracea Nutrition 0.000 description 1
- 244000155437 Raphanus sativus var. niger Species 0.000 description 1
- 241000208422 Rhododendron Species 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical class OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- 235000005324 Typha latifolia Nutrition 0.000 description 1
- 240000000260 Typha latifolia Species 0.000 description 1
- 240000000851 Vaccinium corymbosum Species 0.000 description 1
- 235000003095 Vaccinium corymbosum Nutrition 0.000 description 1
- 235000017537 Vaccinium myrtillus Nutrition 0.000 description 1
- 244000225942 Viola tricolor Species 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
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 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
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 235000021014 blueberries Nutrition 0.000 description 1
- 229920005551 calcium lignosulfonate Polymers 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000034303 cell budding Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 230000005764 inhibitory process Effects 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
- 150000002576 ketones Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
本発明は、一般式
〔式中、R1はアルキル基、アルケニル基、ア
ルキニル基、アルコキシアルキル基またはアルコ
キシアルコキシアルキル基を表わし、R2は水素
原子またはメチル基を表わす。〕
で示されるテトラヒドロフタルイミド誘導体（以
下、本発明化合物と記す。）、その製造法およびそ
れを有効成分とする除草剤に関するものである。
ある種のテトラヒドロフタルイミド誘導体、例
えば、２−（４−メトキシフエニル）−４，５，
６，７−テトラヒドロ−2H−イソインドール−
１，３−ジオンが、除草剤の有効成分として用い
うることは、特公昭48−11940号公報に記載され
ている。しかしながら、これらの化合物は、除草
剤の有効成分として必ずしも常に充分なものであ
るとはいえない。
本発明化合物は畑地の茎葉処理および土壌処理
において、問題となる種々の雑草、例えば、ソバ
カズラ、サナエタデ、スベリヒユ、ハコベ、シロ
ザ、アオビユ（アオゲイトウ）、ダイコン、ノハ
ラガラシ、アメリカツノクサネム、エビスグサ、
イチビ、アメリカキンゴジカ、フイールドパンジ
ー、ヤエムグラ、アメリカアサガオ、マルバアサ
ガオ、ホトケノザ、ヨウシユチヨウセンアサガ
オ、イヌホオズキ、オオイヌノフグリ、オナモ
ミ、ヒマワリ、イヌカミツレ、コーンマリーゴー
ルド等の広葉雑草、ヒエ、イヌビエ、エノコログ
サ、メヒシバ、スズメノカタビラ、ノスズメノテ
ツポウ、エンバク、カラスムギ、セイバンモロコ
シ等のイネ科雑草およびツユクサ等のツユクサ科
雑草、ハマスゲ等のカヤツリグサ科雑草等に対し
て除草効力を有し、しかも本発明化合物はトウモ
ロコシ、コムギ、イネ、ダイズ、ワタ等の主要作
物に対して問題となるような薬害を示さない。
また、本発明化合物は水田の湛水処理において
問題となる種々の雑草、例えば、タイヌビエ、等
のイネ科雑草、アゼナ、キカシグサ、ミゾハコベ
等の広葉雑草、ホタルイ、マツバイ等のカヤツリ
グサ科雑草、コナギ、ウリカワ等に対して除草効
力を有し、しかもイネに対して問題となるような
薬害を示さない。
本発明化合物は、一般式
〔式中、R1およびR2は前記と同じ意味を表わ
す。〕
で示されるアミノベンズオキサジノン誘導体と、
これに対して1.0〜1.1当量の３，４，５，６−テ
トラヒドロフタル酸無水物とを溶媒中、80℃〜
200℃、１時間〜24時間反応させることによつて
製造することができる。
溶媒としては、ベンゼン、トルエン、キシレン
等の芳香族炭化水素類、ジオキサン、エチレング
リコールジメチルエーテル等のエーテル類、蟻
酸、酢酸等の脂肪酸、水等あるいは、それらの混
合物があげられる。
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後処理を行い、必要なら
ば、クロマトグラフイー、再結晶等の操作によつ
て精製することにより、目的の本発明化合物を得
ることができる。
次に本発明化合物の製造例を示す。
製造例 （本発明化合物１の製造）
６−アミノ−７−フルオロ−４−プロパルギル
−2H−１，４−ベンズオキサジン−３（4H）−オ
ン0.31ｇ、３，４，５，６−テトラヒドロフタル
酸無水物0.28ｇ、酢酸３mlの混液を２時間加熱還
流した。放冷後水を加え、酢酸エチルで抽出し
た。有機層を水洗後、重曹水で中和し、乾燥、濃
縮した。（こうして得られた残渣をシリカゲル薄
層クロマトグラフイー（展開溶媒；酢酸エチル：
ヘキサン＝１：２）で精製し、２−（７−フルオ
ロ−４−プロパルギル−2H−１，４−ベンズオ
キサジン−３（4H）−オン−６−イル）−４，５，
６，７−テトラヒドロイソインドール−１，３−
ジオン0.12ｇを得た。
m.p.196.0℃
このような製造法によつて製造できる本発明化
合物のいくつかを、第１表に示す。
The present invention is based on the general formula [In the formula, R 1 represents an alkyl group, an alkenyl group, an alkynyl group, an alkoxyalkyl group, or an alkoxyalkoxyalkyl group, and R 2 represents a hydrogen atom or a methyl group. ] The present invention relates to a tetrahydrophthalimide derivative represented by (hereinafter referred to as the compound of the present invention), a method for producing the same, and a herbicide containing the same as an active ingredient. Certain tetrahydrophthalimide derivatives, such as 2-(4-methoxyphenyl)-4,5,
6,7-tetrahydro-2H-isoindole-
It is described in Japanese Patent Publication No. 11940/1983 that 1,3-dione can be used as an active ingredient of herbicides. However, these compounds cannot always be said to be sufficient as active ingredients for herbicides. The compounds of the present invention can be used to treat various weeds that are problematic in foliar and soil treatments in upland fields, such as freckle weeds, Japanese knotweed, purslane, chickweed, whiteweed, Japanese radish, Japanese daikon radish, Japanese hornwort, American hornwort, Ebisu grass, and other weeds.
Broad-leafed weeds such as common grass, golden deer, field pansies, Japanese grass, American morning glory, Malva morning glory, hotokenoza, Japanese morning glory, Japanese dogweed, Japanese whiteflies, Japanese fir, sunflower, Japanese chamomile, corn marigold, barnyard grass, Japanese barnyard grass, foxtail grass, and black grass. The compound of the present invention has a herbicidal effect on weeds of the grass family, such as sorghum, sycamore, oat, oat, and sorghum, as well as weeds of the cyperaceae family, such as dayflower, and cyperaceae, such as cyperus occidentalis. It does not cause any harmful effects on major crops such as wheat, rice, soybean, and cotton. In addition, the compound of the present invention can be applied to various weeds that are a problem in the waterlogging treatment of rice fields, such as grass weeds such as Japanese millet, broad-leaved weeds such as azalea, commonweed, and chickweed, cyperaceae weeds such as bulrushes, and cyperus spp. It has a herbicidal effect on grasshoppers, etc., and does not cause any harmful effects on rice. The compound of the present invention has the general formula [In the formula, R 1 and R 2 have the same meanings as above. ] An aminobenzoxazinone derivative represented by
To this, 1.0 to 1.1 equivalents of 3,4,5,6-tetrahydrophthalic anhydride was added in a solvent at 80°C to
It can be produced by reacting at 200°C for 1 to 24 hours. Examples of the solvent include aromatic hydrocarbons such as benzene, toluene, and xylene, ethers such as dioxane and ethylene glycol dimethyl ether, fatty acids such as formic acid and acetic acid, water, and mixtures thereof. After the reaction is completed, the reaction solution is added with water, subjected to standard post-treatments such as organic solvent extraction and concentration, and if necessary, purified by chromatography, recrystallization, etc. to obtain the desired product. Inventive compounds can be obtained. Next, production examples of the compounds of the present invention will be shown. Production example (Production of compound 1 of the present invention) 6-amino-7-fluoro-4-propargyl-2H-1,4-benzoxazin-3(4H)-one 0.31 g, 3,4,5,6-tetrahydrophthal A mixture of 0.28 g of acid anhydride and 3 ml of acetic acid was heated under reflux for 2 hours. After cooling, water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with water, neutralized with aqueous sodium bicarbonate, dried, and concentrated. (The residue thus obtained was subjected to silica gel thin layer chromatography (developing solvent: ethyl acetate:
2-(7-fluoro-4-propargyl-2H-1,4-benzoxazin-3(4H)-one-6-yl)-4,5,
6,7-tetrahydroisoindole-1,3-
0.12 g of dione was obtained. mp196.0°C Some of the compounds of the present invention that can be produced by such a production method are shown in Table 1.
【表】
本発明化合物を除草剤の有効成分として用いる
場合は、通常固体担体、液体担体、界面活性剤そ
の他の製剤用補助剤と混合して、乳剤、水和剤、
懸濁剤、粒剤等に製剤する。
これらの製剤には有効成分として本発明化合物
を、重量比で0.05〜90％、好ましくは0.1〜80％
含有する。
固体担体としては、カオリンクレー、アツタパ
ルジヤイトクレー、ベントナイト、酸性白土、パ
イロフイライト、タルク、珪藻土、方解石、クル
ミ粉、尿素、硫酸アンモニウム、合成含水酸化珪
素等の微粉末あるいは粒状物があげられ、液体担
体としては、キシレン、メチルナフタレン等の芳
香族炭化水素類、イソプロパノール、エチレング
リコール、セロソルブ等のアルコール類、アセト
ン、シクロヘキサノン、イソホロン等のケトン
類、大豆油、綿実油等の植物油、ジメチルスルホ
キシド、Ｎ，Ｎ−ジメチルホルムアミド、アセト
ニトリル、水等があげられる。
乳化、分散、湿展等のために用いられる界面活
性剤としては、アルキル硫酸エステル塩、アルキ
ルアリールスルホン酸塩、ジアルキルスルホコハ
ク酸塩、ポリオキシエチレンアルキルアリールエ
ーテルリン酸エステル塩等の陰イオン界面活性
剤、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
オキシエチレンポリオキシプロピレンブロツクコ
ポリマー、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等の非イオ
ン界面活性剤等があげられる。製剤用補助剤とし
ては、リグニンスルホン酸塩、アルギン酸塩、ポ
リビニルアルコール、アラビアガム、CMC（カル
ボキシメチルセルロース）、PAP（酸性リン酸イ
ソプロピル）等があげられる。
次に製剤例を示す。なお、本発明化合物は第１
表の化合物番号で示す。部は重量部を示す。
製剤例 １
本発明化合物１、50部、リグニンスルホン酸カ
ルシウム８部、ラウリル硫酸ナトリウム２部およ
び合成含水酸化珪素45部をよく粉砕混合して水和
剤を得る。
製剤例 ２
本発明化合物２，５部、ポリオキシエチレンス
チリルフエニルエーテル14部、ドデシルベンゼン
スルホン酸カルシウム６部、キシレン38部および
イソホロン45部をよく混合して乳剤を得る。
製剤例 ３
本発明化合物１，２部、合成含水酸化珪素１
部、リグニンスルホン酸カルシウム２部、ベント
ナイト30部およびカオリンクレー65部をよく粉砕
混合し、水を加えてよく練り合せた後、造粒乾燥
して粒剤を得る。
製剤例 ４
本発明化合物３，25部、ポリオキシエチレンソ
ルビタンモノオレエート３部、CMC3部、水69部
を混合し、粒度が５ミクロン以下になるまで湿式
粉砕して懸濁剤を得る。
製剤例 ５
本発明化合物３，５部、ポリキシエチレンスチ
リルフエニルエーテル14部、ドデシルベンゼンス
ルホン酸カルシウム６部、キシレン30部および
Ｎ，Ｎ−ジメチルホルムアミド45部をよく混合し
て乳剤を得る。
このようにして製剤された本発明化合物は、雑
草の出芽前または出芽後に土壌処理、茎葉処理ま
たは湛水処理する。土壌処理には、土壌表面処
理、土壌混和処理等があり、茎葉処理には、植物
体の上方からの処理のほか、作物に付着しないよ
う雑草に限つて処理する局部処理等がある。
また、他の除草剤と混合して用いることによ
り、除草効力の増強を期待できる。さらに、殺虫
剤、殺ダニ剤、殺線虫剤、殺菌剤、植物生長調節
剤、肥料、土壌改良剤等と混合して用いることも
できる。
なお、本発明化合物は、水田、畑地、果樹園、
牧草地、芝生地、森林あるいは非農耕地等の除草
剤の有効成分として用いることができる。
本発明化合物を除草剤の有効成分として用いる
場合、その処理量は、気象条件、製剤形態、施用
時期、方法、場所、対象雑草、対象作物等によつ
ても異なるが、通常１アールあたり0.02ｇ〜100
ｇ、好ましくは、0.05ｇ〜50ｇであり、乳剤、水
和剤、懸濁剤等は、通常その所定量を１アールあ
たり１リツトル〜10リツトルの（必要ならば、展
着剤等の補助剤を添加した）水で希釈して処理
し、粒剤等は、通常なんら希釈することなくその
まゝ処理する。
展着剤としては、前記の界面活性剤のほか、ポ
リオキシエチレン樹脂酸（エステル）、リグニン
スルホン酸塩、アビエチン酸塩、ジナフチルメタ
ンジスルホン酸塩、パラフイン等があげられる。
次に、本発明化合物が除草剤の有効成分として
有用であることを試験例で示す。なお、本発明化
合物は、第１表の化合物番号で示し、比較対照に
用いた化合物は第２表の化合物記号で示す。[Table] When the compound of the present invention is used as an active ingredient of a herbicide, it is usually mixed with a solid carrier, a liquid carrier, a surfactant, and other formulation auxiliaries to form an emulsion, a wettable powder, or a herbicide.
Formulate into suspensions, granules, etc. These preparations contain the compound of the present invention as an active ingredient in a weight ratio of 0.05 to 90%, preferably 0.1 to 80%.
contains. Examples of the solid carrier include fine powders or granules such as kaolin clay, attapalgite clay, bentonite, acid clay, pyrofluorite, talc, diatomaceous earth, calcite, walnut powder, urea, ammonium sulfate, and synthetic hydrous silicon oxide. Examples of liquid carriers include aromatic hydrocarbons such as xylene and methylnaphthalene, alcohols such as isopropanol, ethylene glycol, and cellosolve, ketones such as acetone, cyclohexanone, and isophorone, vegetable oils such as soybean oil and cottonseed oil, dimethyl sulfoxide, Examples include N,N-dimethylformamide, acetonitrile, water and the like. Surfactants used for emulsification, dispersion, wetting, etc. include anionic surfactants such as alkyl sulfate salts, alkylaryl sulfonate salts, dialkyl sulfosuccinate salts, and polyoxyethylene alkylaryl ether phosphate salts. Examples include nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether, polyoxyethylene polyoxypropylene block copolymer, sorbitan fatty acid ester, and polyoxyethylene sorbitan fatty acid ester. Examples of formulation adjuvants include lignin sulfonate, alginate, polyvinyl alcohol, gum arabic, CMC (carboxymethyl cellulose), PAP (isopropyl acid phosphate), and the like. Examples of formulations are shown below. In addition, the compound of the present invention is the first
Indicated by compound number in the table. Parts indicate parts by weight. Formulation Example 1 50 parts of Compound 1 of the present invention, 8 parts of calcium lignosulfonate, 2 parts of sodium lauryl sulfate, and 45 parts of synthetic hydrous silicon oxide are thoroughly ground and mixed to obtain a wettable powder. Formulation Example 2 2.5 parts of the compound of the present invention, 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate, 38 parts of xylene and 45 parts of isophorone are thoroughly mixed to obtain an emulsion. Formulation Example 3 1.2 parts of the compound of the present invention, 1 part of synthetic hydrated silicon oxide
1 part, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 65 parts of kaolin clay are thoroughly ground and mixed, water is added and the mixture is thoroughly kneaded, followed by granulation and drying to obtain granules. Formulation Example 4 3.25 parts of the compound of the present invention, 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC, and 69 parts of water are mixed and wet-pulverized until the particle size becomes 5 microns or less to obtain a suspension. Formulation Example 5 3.5 parts of the compound of the present invention, 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate, 30 parts of xylene and 45 parts of N,N-dimethylformamide are thoroughly mixed to obtain an emulsion. The compound of the present invention thus formulated is treated with soil, foliage, or flooding before or after the emergence of weeds. Soil treatment includes soil surface treatment, soil mixing treatment, etc., and foliage treatment includes treatment from above the plant body, as well as local treatment that treats only weeds so that they do not attach to crops. Furthermore, by mixing it with other herbicides, it can be expected to increase the herbicidal efficacy. Furthermore, it can be used in combination with insecticides, acaricides, nematicides, fungicides, plant growth regulators, fertilizers, soil conditioners, and the like. The compound of the present invention can be used in rice fields, fields, orchards,
It can be used as an active ingredient in herbicides for pastures, lawns, forests, non-agricultural lands, etc. When the compound of the present invention is used as an active ingredient of a herbicide, the amount to be treated will vary depending on weather conditions, formulation form, application time, method, location, target weeds, target crops, etc., but is usually 0.02 g per are. ~100
g, preferably 0.05 g to 50 g, and emulsions, wetting agents, suspending agents, etc. are usually used in a specified amount of 1 liter to 10 liters per are (if necessary, auxiliary agents such as spreading agents etc.) Granules, etc. are usually treated as they are without any dilution. Examples of the spreading agent include, in addition to the above-mentioned surfactants, polyoxyethylene resin acids (esters), lignin sulfonates, abietates, dinaphthylmethane disulfonates, paraffin, and the like. Next, test examples will show that the compounds of the present invention are useful as active ingredients of herbicides. The compounds of the present invention are indicated by the compound numbers in Table 1, and the compounds used for comparison are indicated by the compound symbols in Table 2.
【表】
また、除草効力は、調査時の供試植物の出芽お
よび生育阻害の程度を肉眼観察し、化合物を供試
していない場合と全くないしほとんど違いがない
ものを「０」とし、供試植物が枯死ないし生育が
完全に阻害されているものを「５」として、０〜
５の６段階に評価し、０，１，２，３，４，５で
示す。
試験例１ 畑地土壌処理試験
直径10cm、深さ10cmの円筒型プラスチツクポツ
トに畑地土壌を詰め、ヒエ、マルバアサガオ、イ
チビを播種し、覆土した。製剤例２または５に準
じて供試化合物を乳剤にし、その所定量を、１ア
ールあたり10リツトル相当の水で希釈し、小型噴
霧器で土壌表面に処理した。処理後20日間温室内
で育成し、除草効力を調査した。その結果を第３
表に示す。[Table] In addition, the herbicidal efficacy is determined by visually observing the degree of inhibition of budding and growth of the test plants during the survey, and ``0'' indicates that there is no or almost no difference from when no compound is tested. A rating of 0 to 5 indicates that the plant is withering or its growth is completely inhibited.
It is evaluated in 6 stages of 5, and is shown as 0, 1, 2, 3, 4, and 5. Test Example 1 Upland Soil Treatment Test A cylindrical plastic pot with a diameter of 10 cm and a depth of 10 cm was filled with upland soil, sown with Japanese barnyard grass, Japanese morning glory, and Japanese staghorn, and covered with soil. The test compound was made into an emulsion according to Formulation Example 2 or 5, a predetermined amount of the emulsion was diluted with water equivalent to 10 liters per are, and the emulsion was applied to the soil surface using a small sprayer. After treatment, they were grown in a greenhouse for 20 days and their herbicidal efficacy was investigated. The result is the third
Shown in the table.
【表】
試験例２ 畑地茎葉処理試験
直径10cm、深さ10cmの円筒型プラスチツクポツ
トに畑地土壌を詰め、ヒエ、ダイコン、イチビを
播種し、温室内で10日間育成した。その後、製剤
例２または５に準じて供試化合物を乳剤にし、そ
の所定量を、１アールあたり10リツトル相当の展
着剤を含む水で希釈し、小型噴霧器で植物体の上
方から茎葉処理した。処理後20日間温室内で育成
し、除草効力を調査した。その結果を第４表に示
す。[Table] Test Example 2 Field soil treatment test A cylindrical plastic pot with a diameter of 10 cm and a depth of 10 cm was filled with field soil, and barnyard grass, Japanese radish, and Japanese radish were sown and grown in a greenhouse for 10 days. Thereafter, the test compound was made into an emulsion according to Formulation Example 2 or 5, a predetermined amount of the emulsion was diluted with water containing a spreading agent equivalent to 10 liters per are, and the foliage was treated from above the plant using a small sprayer. . After treatment, they were grown in a greenhouse for 20 days and their herbicidal efficacy was investigated. The results are shown in Table 4.
【表】【table】
【表】
試験例３ 水田湛水処理試験
直径８cm、深さ12cmの円筒型プラスチツクポツ
トに水田土壌を詰め、タイヌビエ、広葉雑草（ア
ゼナ、キカシグサ、ミゾハコベ）の種子を１〜２
cmの深さに混ぜ込んだ。湛水して水田状態にした
後、２葉期のイネを移植し、温室内で育成した。
６日後（各雑草の発生初期）に製剤例２または５
に準じて供試化合物を乳剤にし、その所定量を５
ミリリツトルの水で希釈し、水面に処理した。処
理後20日間温室内で育成し、除草効力を調査し
た。その結果を第５表に示す。[Table] Test Example 3 Paddy field flooding treatment test A cylindrical plastic pot with a diameter of 8 cm and a depth of 12 cm was filled with paddy soil, and 1 to 2 seeds of Japanese millet and broad-leaved weeds (Azaena, Kikashigusa, Chickweed) were added to the pot.
Mixed to a depth of cm. After flooding the rice field to create a paddy field, two-leaf stage rice was transplanted and grown in a greenhouse.
Formulation Example 2 or 5 after 6 days (early stage of each weed's emergence)
Make the test compound into an emulsion according to
It was diluted with milliliters of water and applied to the water surface. After treatment, they were grown in a greenhouse for 20 days and their herbicidal efficacy was investigated. The results are shown in Table 5.
【表】
試験例４ 畑地土壌処理試験
面積33×23cm3、深さ11cmのバツトに畑地土壌を
詰め、ダイズ、トウモロコシ、オナモミ、マルバ
アサガオ、イチビ、アオビユ、イヌホオズキ、イ
ヌビエ、エノコログサを播種し、１〜２cmの厚さ
に覆土した。製剤例２または５に準じて供試化合
物を乳剤にし、その所定量を、１アールあたり10
リツトル相当の水で希釈し、小型噴霧器で土壌表
面に処理した。処理後20日間温室内で育成し、除
草効力を調査した。その結果を第６表に示す。[Table] Test Example 4 Upland Soil Treatment Test Field soil was filled into a pot with an area of 33 x 23 cm 3 and a depth of 11 cm, and soybeans, corn, Japanese fir, Japanese morning glory, Japanese velvet, blueberry, Japanese Physalis, Japanese commonweed, and foxglove were sown. The soil was covered with soil to a thickness of ~2 cm. The test compound was made into an emulsion according to Formulation Example 2 or 5, and the prescribed amount was 10
It was diluted with a liter of water and applied to the soil surface using a small sprayer. After treatment, they were grown in a greenhouse for 20 days and their herbicidal efficacy was investigated. The results are shown in Table 6.
【表】
試験例５ 畑地土壌処理試験
面積33×23cm3、深さ11cmのバツトに畑地土壌を
詰め、コムギ、ヤエムグラ、オオイヌノフグリ、
ハコベ、シロザ、サナエタデ、ソバカズラ、スズ
メノカタビラを播種し、１〜２cmの厚さに覆土し
た。製剤例２または５に準じて供試化合物を乳剤
にし、その所定量を、１アールあたり10リツトル
相当の水で希釈し、小型噴霧器で土壌表面に処理
した。処理後27日間温室内で育成し、除草効力を
調査した。その結果を第７表に示す。[Table] Test Example 5 Upland Soil Treatment Test Upland soil was filled into a vat with an area of 33 x 23 cm 3 and a depth of 11 cm, and wheat, Japanese violet, Japanese violet,
Chickweed, whiteweed, Japanese knotweed, buckwheat, and sycamore were sown and covered with soil to a thickness of 1 to 2 cm. The test compound was made into an emulsion according to Formulation Example 2 or 5, a predetermined amount of the emulsion was diluted with water equivalent to 10 liters per are, and the emulsion was applied to the soil surface using a small sprayer. After treatment, the plants were grown in a greenhouse for 27 days and their herbicidal efficacy was investigated. The results are shown in Table 7.
【表】
試験例６ 畑地茎葉処理試験
面積33×23cm3、深さ11cmのバツトに畑地土壌を
詰め、トウモロコシ、コムギ、テンサイ、オナモ
ミ、イチビ、イヌホオズキ、マルバアサガオ、シ
ロザ、エノコログサを播種し、18日間育成した。
その後、製剤例２または５に準じて供試化合物を
乳剤にし、その所定量を、展着剤を含む１アール
あたり５リツトル相当の水で希釈し、小型噴霧器
で植物体の上方から茎葉部全面に均一に処理し
た。このとき雑草および作物の生育状況は草種に
より異なるが、１〜４葉期で、草丈は２〜12cmで
あつた。処理20日後に除草効力を調査した。その
結果を第８表に示す。なお、本試験は、全期間を
通して温室内で行つた。[Table] Test Example 6 Field soil stem and leaf treatment test Field soil was filled into a vat with an area of 33 x 23 cm 3 and a depth of 11 cm, and corn, wheat, sugar beet, Japanese fir, Japanese radish, Japanese Physalis, Maruba morning glory, Shiroza, and Japanese foxtail were sown. It was grown for days.
Thereafter, make the test compound into an emulsion according to Formulation Example 2 or 5, dilute the specified amount with water equivalent to 5 liters per are containing a spreading agent, and use a small sprayer to spray the entire stem and leaf area from above the plant body. was uniformly processed. At this time, the growth conditions of weeds and crops varied depending on the grass species, but they were in the 1-4 leaf stage and the plant height was 2-12 cm. Herbicidal efficacy was investigated 20 days after treatment. The results are shown in Table 8. This test was conducted in a greenhouse throughout the entire period.
Claims (1)
ルキニル基、アルコキシアルキル基またはアルコ
キシアルコキシアルキル基を表わし、R2は水素
原子またはメチル基を表わす。〕 で示されるテトラヒドロフタルイミド誘導体。 ２ 一般式 〔式中、R1はアルキル基、アルケニル基、ア
ルキニル基、アルコキシアルキル基またはアルコ
キシアルコキシアルキル基を表わし、R2は水素
原子またはメチル基を表わす。〕 で示されるアミノベンズオキサジノン誘導体と
３，４，５，６−テトラヒドロフタル酸無水物と
を反応させることを特徴とする一般式 〔式中、R1およびR2は前記と同じ意味を表わ
す。〕 で示されるテトラヒドロフタルイミド誘導体の製
造法。 ３ 一般式 〔式中、R1はアルキル基、アルケニル基、ア
ルキニル基、アルコキシアルキル基またはアルコ
キシアルコキシアルキル基を表わし、R2は水素
原子またはメチル基を表わす。〕 で示されるテトラヒドロフタルイミド誘導体を有
効成分とすることを特徴とする除草剤。[Claims] 1. General formula [In the formula, R 1 represents an alkyl group, an alkenyl group, an alkynyl group, an alkoxyalkyl group, or an alkoxyalkoxyalkyl group, and R 2 represents a hydrogen atom or a methyl group. ] A tetrahydrophthalimide derivative represented by 2 General formula [In the formula, R 1 represents an alkyl group, an alkenyl group, an alkynyl group, an alkoxyalkyl group, or an alkoxyalkoxyalkyl group, and R 2 represents a hydrogen atom or a methyl group. ] A general formula characterized by reacting an aminobenzoxazinone derivative represented by the formula with 3,4,5,6-tetrahydrophthalic anhydride. [In the formula, R 1 and R 2 have the same meanings as above. ] A method for producing a tetrahydrophthalimide derivative represented by 3 General formula [In the formula, R 1 represents an alkyl group, an alkenyl group, an alkynyl group, an alkoxyalkyl group, or an alkoxyalkoxyalkyl group, and R 2 represents a hydrogen atom or a methyl group. ] A herbicide characterized by containing a tetrahydrophthalimide derivative represented by the following as an active ingredient.
Priority Applications (20)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59198245A JPS6176486A (en) | 1984-09-20 | 1984-09-20 | Tetrahydrophthalimide derivative, its production, and herbicide containing same as active ingredient |
| US06/756,251 US4640707A (en) | 1984-07-23 | 1985-07-18 | Tetrahydrophthalimides and their herbicidal use |
| HU852792A HU199250B (en) | 1984-07-23 | 1985-07-22 | Herbicide and process for production of the tetrahydroftalimid active substance derivative |
| ES545464A ES8609313A1 (en) | 1984-07-23 | 1985-07-22 | Tetrahydrophtalimides, and their production and use. |
| AU45230/85A AU570812B2 (en) | 1984-07-23 | 1985-07-22 | Tetrahydrophthalimides |
| DK333885A DK171351B1 (en) | 1984-07-23 | 1985-07-22 | Tetrahydrophthalimide derivatives, process for their preparation, herbicidal compositions containing the compounds, use of the compounds and intermediates for use in the preparation. |
| CA000487286A CA1253863A (en) | 1984-07-23 | 1985-07-23 | Tetrahydrophthalimides, and their production and use |
| DE8585109201T DE3574379D1 (en) | 1984-07-23 | 1985-07-23 | Tetrahydrophtalimides, and their production and use |
| PL1985254653A PL145919B1 (en) | 1984-07-23 | 1985-07-23 | Herbicide |
| EP85109201A EP0170191B1 (en) | 1984-07-23 | 1985-07-23 | Tetrahydrophtalimides, and their production and use |
| BR8503490A BR8503490A (en) | 1984-07-23 | 1985-07-23 | COMPOUND, PROCESS TO PREPARE COMPOUND, COMPOSITION, PROCESS TO EXTERMINE WEEDS AND USE OF A COMPOUND |
| CS855440A CS261227B2 (en) | 1984-07-23 | 1985-07-23 | Herbicide and method of its efficient component production |
| KR1019850005260A KR920003558B1 (en) | 1984-07-23 | 1985-07-23 | Process for the preparation of tetrahydro phthalimides |
| US06/914,496 US4792605A (en) | 1984-07-23 | 1986-10-02 | 1,4-benzoxazin-3-one-6-(amino or nitro) intermediates |
| MYPI87000998A MY100731A (en) | 1984-07-23 | 1987-07-14 | Tetrahydrophthalimides, and their production and use |
| AU11177/88A AU581823B2 (en) | 1984-07-23 | 1988-02-01 | Benzoxazone derivatives |
| CA000575317A CA1264323A (en) | 1984-07-23 | 1988-08-19 | Amino or nitro derivatives of benzoxazole-2-one and benzoxazin-3-one |
| US07/246,783 US4880925A (en) | 1984-07-23 | 1988-09-20 | Intermediates for the production of tetrahydrophthalimides |
| CA000601059A CA1273339A (en) | 1984-07-23 | 1989-05-29 | Compounds useful as starting compounds in the preparation of tetrahydrophthalimides |
| DK049095A DK171725B1 (en) | 1984-07-23 | 1995-04-25 | Benzoxazine and benzoxazole derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59198245A JPS6176486A (en) | 1984-09-20 | 1984-09-20 | Tetrahydrophthalimide derivative, its production, and herbicide containing same as active ingredient |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6176486A JPS6176486A (en) | 1986-04-18 |
| JPH041748B2 true JPH041748B2 (en) | 1992-01-14 |
Family
ID=16387917
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59198245A Granted JPS6176486A (en) | 1984-07-23 | 1984-09-20 | Tetrahydrophthalimide derivative, its production, and herbicide containing same as active ingredient |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6176486A (en) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4877444A (en) * | 1987-08-27 | 1989-10-31 | Sumitomo Chemical Company, Limited | Tetrahydroindazolyl-benzoxazines and use |
| JP2727588B2 (en) * | 1988-10-05 | 1998-03-11 | 住友化学工業株式会社 | Herbicidal composition |
| AU627906B2 (en) | 1989-07-14 | 1992-09-03 | Nissan Chemical Industries Ltd. | Uracil derivatives and herbicides containing the same as active ingredient |
| BRPI0722192A2 (en) | 2007-10-30 | 2014-06-24 | Sumitomo Chemical Co | HERBICIDE COMPOSITION. |
| JP2013166724A (en) * | 2012-02-16 | 2013-08-29 | Sumitomo Chemical Co Ltd | Crystalline form of flumioxazin |
| JP2013256478A (en) * | 2012-06-14 | 2013-12-26 | Sumitomo Chemical Co Ltd | Crystal form of flumioxazin |
| WO2014142308A1 (en) * | 2013-03-15 | 2014-09-18 | 公益財団法人相模中央化学研究所 | Bicyclic pyrazolinone derivative and herbicide comprising same as effective component thereof |
| US9580444B2 (en) | 2013-03-15 | 2017-02-28 | Sagami Chemical Research Institute | Polycyclic pyrazolinone derivative and herbicide comprising same as effective component thereof |
| JP6156074B2 (en) * | 2013-11-08 | 2017-07-05 | 住友化学株式会社 | Succinimide compounds and uses thereof |
| WO2019020987A1 (en) * | 2017-07-24 | 2019-01-31 | Redag Crop Protection Ltd. | Benzoxazinone derivatives useful as herbicides |
| BR102018075132A2 (en) | 2018-12-04 | 2020-06-16 | UPL Corporation Limited | WIDE SPECTRUM SYNERGISTIC HERBICIDE COMPOSITION FOR THE CONTROL OF WEEDS IN AGRICULTURAL CROPS, USE OF THESE COMPOSITION FOR PREPARATION OF PRODUCT, PRODUCT AND APPLICATION METHOD |
-
1984
- 1984-09-20 JP JP59198245A patent/JPS6176486A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6176486A (en) | 1986-04-18 |
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