JPH01180870A - Cyclohexane derivative, its production, herbicide containing it, and method combating weeds using it - Google Patents
Cyclohexane derivative, its production, herbicide containing it, and method combating weeds using itInfo
- Publication number
- JPH01180870A JPH01180870A JP164988A JP164988A JPH01180870A JP H01180870 A JPH01180870 A JP H01180870A JP 164988 A JP164988 A JP 164988A JP 164988 A JP164988 A JP 164988A JP H01180870 A JPH01180870 A JP H01180870A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- present
- weeds
- treatment
- 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 24
- 239000004009 herbicide Substances 0.000 title claims abstract description 12
- 238000004519 manufacturing process Methods 0.000 title claims description 12
- 238000000034 method Methods 0.000 title claims description 8
- 125000000113 cyclohexyl group Chemical class [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 title claims 5
- 241000196324 Embryophyta Species 0.000 title abstract description 34
- -1 inorganic acid salt Chemical class 0.000 claims abstract description 20
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 7
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000004480 active ingredient Substances 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000001475 halogen functional group Chemical group 0.000 claims description 2
- 238000009333 weeding Methods 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 40
- 238000011282 treatment Methods 0.000 abstract description 26
- 239000002689 soil Substances 0.000 abstract description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 21
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract description 9
- 240000007594 Oryza sativa Species 0.000 abstract description 6
- 235000007164 Oryza sativa Nutrition 0.000 abstract description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract description 6
- 235000009566 rice Nutrition 0.000 abstract description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract description 3
- 238000002360 preparation method Methods 0.000 abstract description 2
- 125000006193 alkinyl group Chemical group 0.000 abstract 1
- HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical compound O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000000262 haloalkenyl group Chemical group 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 19
- 239000000839 emulsion Substances 0.000 description 18
- 238000009472 formulation Methods 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 244000062793 Sorghum vulgare Species 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-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
- 244000025254 Cannabis sativa Species 0.000 description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 5
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000003892 spreading Methods 0.000 description 5
- 244000075850 Avena orientalis Species 0.000 description 4
- 235000007319 Avena orientalis Nutrition 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 244000058871 Echinochloa crus-galli Species 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 235000006140 Raphanus sativus var sativus Nutrition 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 239000004927 clay Substances 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 230000012010 growth Effects 0.000 description 4
- 235000019713 millet Nutrition 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 240000001592 Amaranthus caudatus Species 0.000 description 3
- 235000009328 Amaranthus caudatus Nutrition 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
- 235000008247 Echinochloa frumentacea Nutrition 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-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
- 235000005733 Raphanus sativus var niger Nutrition 0.000 description 3
- 240000001970 Raphanus sativus var. sativus Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000002585 base Substances 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
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 230000009931 harmful effect Effects 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 229910052814 silicon oxide Inorganic materials 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 239000000725 suspension 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
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- 235000007558 Avena sp Nutrition 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- 244000301850 Cupressus sempervirens Species 0.000 description 2
- 241000234646 Cyperaceae Species 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229920001732 Lignosulfonate Polymers 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 241001076438 Oxya japonica Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 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
- 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
- 239000000969 carrier Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 150000001934 cyclohexanes Chemical class 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 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
- 238000002156 mixing Methods 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000004381 surface treatment Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N 1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylic acid Chemical compound C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-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
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- JVKRKMWZYMKVTQ-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]pyrazol-1-yl]-N-(2-oxo-3H-1,3-benzoxazol-6-yl)acetamide Chemical group C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C=NN(C=1)CC(=O)NC1=CC2=C(NC(O2)=O)C=C1 JVKRKMWZYMKVTQ-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-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
- 240000004731 Acer pseudoplatanus Species 0.000 description 1
- 235000002754 Acer pseudoplatanus Nutrition 0.000 description 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 229910021532 Calcite Inorganic materials 0.000 description 1
- OYPRJOBELJOOCE-IGMARMGPSA-N Calcium-40 Chemical group [40Ca] OYPRJOBELJOOCE-IGMARMGPSA-N 0.000 description 1
- 241000233838 Commelina Species 0.000 description 1
- 241000234653 Cyperus Species 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 240000003173 Drymaria cordata Species 0.000 description 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
- 241000219146 Gossypium Species 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 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
- 244000064622 Physalis edulis Species 0.000 description 1
- 235000006485 Platanus occidentalis Nutrition 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
- 244000184734 Pyrus japonica Species 0.000 description 1
- 241000220259 Raphanus Species 0.000 description 1
- 241000208422 Rhododendron Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 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
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 241001148683 Zostera marina Species 0.000 description 1
- RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 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
- 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
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 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
- 150000008052 alkyl sulfonates 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
- 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 1
- 239000004202 carbamide Substances 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000034303 cell budding Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 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
- 238000011156 evaluation Methods 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 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
- 239000005645 nematicide Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- KPTCZURLWZSRKB-UHFFFAOYSA-N o-prop-2-enylhydroxylamine Chemical compound NOCC=C KPTCZURLWZSRKB-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 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
- 239000003208 petroleum Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 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
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 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
- 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
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 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
- 239000004563 wettable powder Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (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〉
本発明は新規なシクロヘキサン誘導体、その製造法、そ
れを有効成分とする除草剤およびそれを用いる除草方法
に関するものである。DETAILED DESCRIPTION OF THE INVENTION <Industrial Application Field> The present invention relates to a novel cyclohexane derivative, a method for producing the same, a herbicide containing the same as an active ingredient, and a weed control method using the same.
〈従来の技術〉
これまで、特開昭５４−４６７４９号公報、特開昭５４
−１１５８４９号公報等にある種のシフロヘキサン誘導
体が、除草剤の有効成分として用い得ることが記載され
ている。<Prior art> Until now, Japanese Patent Application Laid-Open No. 54-46749,
JP-115849 and the like describes that certain cyflohexane derivatives can be used as active ingredients of herbicides.
〈発明が解決しようとする課題〉
しかしながら、これらの化合物は、除草効力が不充分で
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とは言い難い。<Problems to be Solved by the Invention> However, these compounds are not necessarily satisfactory because their herbicidal efficacy is insufficient or their selectivity between crops and weeds is poor.
〈課題を解決するための手段〉
本発明者らはこのような状況に鑑み、優れた除草剤を開
発すべく種々検討を重ねた結果、下記の化合物が低薬量
で優れた除草効力を有し、かつ、作物に対して問題とな
るような薬害を示さないことを見出し本発明に至った。<Means for Solving the Problems> In view of the above situation, the present inventors conducted various studies to develop an excellent herbicide, and as a result, the following compound has an excellent herbicidal effect at a low dose. The present inventors have discovered that this method does not cause any harmful chemical damage to crops, leading to the present invention.
即ち、本発明は、−殺伐〔Ｉ〕
〔式中、ゾは低級アルキル基を表わし、Ｒ２は低級アル
キル基、低級アルケニル基、低級アルキニル基またはハ
ロ低級アルケニル基を表わす。〕で示されるシクロヘキ
サン誘導体（以下、本発明化合物と記す。）、その製造
法、それを有効成分とする除草剤およびそれを用いる除
草方法を提供するものである。That is, the present invention provides the following method: -Salt [I] [wherein zo represents a lower alkyl group, and R2 represents a lower alkyl group, a lower alkenyl group, a lower alkynyl group, or a halo lower alkenyl group. The present invention provides a cyclohexane derivative represented by (hereinafter referred to as the compound of the present invention), a method for producing the same, a herbicide containing the same as an active ingredient, and a weeding method using the same.
まず、本発明化合物の製造法について説明する。First, the method for producing the compound of the present invention will be explained.
本発明化合物は一般式〔■〕
〔式中、Ｒ１は前記と同じ意味を表わす。〕で示される
アシルシクロヘキサン誘導体と一般式［１１］
％式％［）
〔式中、Ｒ２は前記と同じ意味を表わす。〕で示される
ヒドロキシルアミンまたはその無機酸塩とを反応させる
ことによって製造することができる。The compound of the present invention has the general formula [■] [wherein R1 represents the same meaning as above]. ] and the acylcyclohexane derivative represented by the general formula [11] % formula % [) [wherein R2 represents the same meaning as above. ] It can be produced by reacting with hydroxylamine or its inorganic acid salt.
該反応は通常、無溶媒または溶媒中、必要により塩基の
存在下で行い、反応温度の範囲は０〜１００℃、反応時
間の範囲は０５〜２４時間であり、反応に供される試剤
の量は、−殺伐（ｎ）で示されるアシルシクロヘキサン
誘導体１当量に対して一般式［１［１］で示されるヒド
ロキシルアミンまたはその無機酸塩は１〜１．５当量、
塩基は１〜１．５当重である。The reaction is usually carried out without a solvent or in a solvent, if necessary in the presence of a base, the reaction temperature ranges from 0 to 100°C, the reaction time ranges from 0.5 to 24 hours, and the amount of reagent used for the reaction is 1 to 1.5 equivalents of hydroxylamine represented by the general formula [1 [1] or its inorganic acid salt relative to 1 equivalent of the acylcyclohexane derivative represented by -kill (n),
The base has an equivalent weight of 1 to 1.5.
反応に用いられる溶媒としては、例えばヘキサン、ヘプ
タン、リグロイン、石油エーテル等の脂Ｕｊ 族炭化水
素類、ベンゼン、トルエン、キシレン等の芳香族炭化水
素類、クロロホルム、四塩化炭素、ジクロロエタン、ク
ロロベンゼン、ジクロロベンゼン等のハロゲン化炭化水
素類、ジエチルエーテル、ジイソプロピルエーテル、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、メタノール、エタノ
ール、イソプロパツール、ｔ−ブタノール、オクタツー
ル、シクロヘキサノール、メチルセロソルブ、ジエチレ
ングリコール、グリセリン等のアルコール類、酢酸エチ
ル、酢酸ブチル等のエステル類、ニトロエタン、ニトロ
ベンゼン等のニトロ化合物、アセトニトリル、イソブチ
ロニトリル等のニトリル類、ピリジン、トリエチルアミ
ン、Ｎ。Examples of solvents used in the reaction include aliphatic hydrocarbons such as hexane, heptane, ligroin, and petroleum ether, aromatic hydrocarbons such as benzene, toluene, and xylene, chloroform, carbon tetrachloride, dichloroethane, chlorobenzene, and dichloromethane. Halogenated hydrocarbons such as chlorobenzene, ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, diethylene glycol dimethyl ether, methanol, ethanol, isopropanol, t-butanol, octatool, cyclohexanol, methyl cellosolve, diethylene glycol, glycerin alcohols such as ethyl acetate and butyl acetate, nitro compounds such as nitroethane and nitrobenzene, nitriles such as acetonitrile and isobutyronitrile, pyridine, triethylamine, N.
Ｎ−ジエチルアニリン、トリブチルアミン、Ｎ−メチル
モルホリン等の第三級アミン類、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類
、ジメチルスルホキシド、スルホラン等の硫黄化合物、
水等あるいは、それらの混合物があげられる。Tertiary amines such as N-diethylaniline, tributylamine, N-methylmorpholine, formamide, N,N
- acid amides such as dimethylformamide and acetamide; sulfur compounds such as dimethyl sulfoxide and sulfolane;
Examples include water and mixtures thereof.
塩基としては、例えばピリジン、トリエチルアミン、Ｎ
、Ｎ−ジエチルアニリン等の有機塩基、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、ナトリウムメトキシド
、ナトリウムエトキシド等のアルカリ金属アルコキシド
等があげられる。Examples of the base include pyridine, triethylamine, N
, organic bases such as N-diethylaniline, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate,
Examples include inorganic bases such as sodium hydride and alkali metal alkoxides such as sodium methoxide and sodium ethoxide.
反応終了後の反応液は水にあけ、中性〜酸性にした後、
有機溶媒抽出および濃縮等の通常の後処理を行い目的の
本発明化合物を得ることができる。After the reaction is complete, pour the reaction solution into water to make it neutral to acidic.
The desired compound of the present invention can be obtained by conventional post-treatments such as organic solvent extraction and concentration.
また、必要によりクロマトグラフィー、再結晶等の操作
により精製することができる。Further, if necessary, it can be purified by operations such as chromatography and recrystallization.
上記の製造法に準じて製造される本発明化合物のいくつ
かを第１表に示す。Table 1 shows some of the compounds of the present invention produced according to the above production method.
第 １ 表
一般式（１）で示される本発明化合物は、次に示す互変
異性構造が考えられる。The compound of the present invention represented by the general formula (1) in Table 1 may have the following tautomeric structure.
同様に、−軟式（ＩＩ）で示されるアシルシクロヘキサ
ン誘導体も次のような互変異性構造をとると考えられる
。Similarly, the acylcyclohexane derivative represented by -soft formula (II) is also considered to have the following tautomeric structure.
本発明化合物を製造する際の原料化合物である一般式（
ｎ）で示されるアシルシクロヘキサン誘導体は、例えば
次に示す経路により製造される。General formula (
The acylcyclohexane derivative represented by n) is produced, for example, by the following route.
＊ 触媒としては例えば４−ジメチルアミノピリジンが
用いられる。*For example, 4-dimethylaminopyridine is used as the catalyst.
本発明化合物は、優れた除草効力を有し、かつ作物・雑
草間に優れた選択性を示す。すなわち本発明化合物は、
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、スベリヒエ、アオゲイトウ、ダイコ
ン、イチビ、イヌホオズキ、オオイヌノフグリ等の広葉
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、ノスズメノテッポウ、エンバク、カラス
ムギ、セイバンモロコシ、シバムギ、ウマノチャヒキ等
のイネ科雑草およびツユクサ等のツユクサ科雑草、コゴ
メガヤツリ、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、オオムギ、イネ、ダイズ、ワタ、テンサイ
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
。The compounds of the present invention have excellent herbicidal efficacy and exhibit excellent selectivity between crops and weeds. That is, the compound of the present invention is
Various weeds that pose problems in the treatment of foliage and soil in fields, such as broad-leaved weeds such as purslane, Japanese radish, Japanese radish, Japanese commonweed, Japanese Physalis, and Japanese staghorn, Japanese barnyard grass, Japanese commonweed, American foxtail grass, Japanese grasshopper, Japanese staghorn grass, Japanese grasshopper, oats, oats, etc. The compound of the present invention has a herbicidal effect on weeds of the grass family such as , Seiban sorghum, barley, and cypress, as well as weeds of the family Cyperaceae such as dayflower, Cyperaceae such as cyperus sorghum, and cypress It does not cause any harmful chemical damage to major crops such as rice, soybean, cotton, and sugar beet.
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等に対
して除草効力を有し、しかもイネに対しては問題となる
ような薬害を示さない。In addition, the compound of the present invention has a herbicidal effect on various weeds that are problematic in the waterlogging treatment of rice fields, such as grass weeds such as Japanese millet, broad-leaved weeds such as azalea, japonica, and chickweed. It does not show any harmful effects on rice.
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
して用いる。When using the compound of the present invention as an active ingredient of a herbicide,
It is usually mixed with solid carriers, liquid carriers, surfactants, and other formulation auxiliaries to formulate emulsions, wettable powders, suspensions, granules, and the like.
これらの製剤には有効成分として本発明化合物を、重重
比で０．１〜９０％、好ましくは０．２〜８０チ含有す
る。These preparations contain the compound of the present invention as an active ingredient in a weight ratio of 0.1 to 90%, preferably 0.2 to 80%.
固体担体としては、カオリンクレー、アツタノ（ルジャ
イトクレー、ベントナイト、酸性白土、７寸イロフィラ
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、イソプロパツール、
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。Examples of the solid carrier include fine powders or granules such as kaolin clay, atsutano (lugite clay, bentonite, acid clay, 7-inch ylophyllite, talc, diatomaceous earth, calcite, walnut powder, urea, ammonium sulfate, and synthetic hydrous silicon oxide). , as a liquid carrier, aromatic hydrocarbons such as xylene and methylnaphthalene, isopropanol,
Alcohols such as ethylene glycol and cellosolve; ketones such as acetone, cyclohexanone and isophorone;
Vegetable oils such as soybean oil and cottonseed oil, dimethyl sulfoxide, N
, N-dimethylformamide, acetonitrile, water and the like.
乳化、分散、湿炭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、アルキルスルホン酸塩
、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
プロピレンブロックコポリマー、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。Surfactants used for emulsification, dispersion, wet carbonization, etc. include alkyl sulfate salts, alkyl sulfonate salts, alkylaryl sulfonate salts, dialkyl sulfosuccinate salts, polyoxyethylene alkylaryl ether phosphate salts, etc. Nonionic surfactants such as anionic surfactants, polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene polyoxypropylene block copolymers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, etc. .
その他の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。Other formulation adjuvants include lignin sulfonate, alginate, polyvinyl alcohol, gum arabic, CMC (carboxymethyl cellulose), PAP.
(acidic isopropyl phosphate), etc.
本発明化合物は、通常製剤化して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
ないよう雑草暑こ限って処理する局部処理等がある。The compound of the present invention is usually formulated and 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 in which weeds are treated only in hot weather to prevent them from adhering to crops.
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。Further, 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.
分として用いることができる。It can be used as a minute.
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、処理時期、方法、場
所、対象雑草、対象作物等によっても異なるが、通常１
アールあたり０．０５９〜５０り、好ましくは、０．１
！ｉ２〜１０７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
なくそのまま処理する。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, treatment time, method, location, target weeds, target crops, etc., but usually 1.
0.059 to 50 per are, preferably 0.1
! i2 to 107, emulsions, wettable powders, suspensions, etc.
Usually, the prescribed amount is diluted with 1 to 10 liters of water per are (if necessary, an auxiliary agent such as a spreading agent is added). Process.
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
ラフィン等があげられる。In addition to the above-mentioned surfactants, the spreading agents include polyoxyethylene resin acid (ester), lignin sulfonate,
Examples include abietate, dinaphthylmethane disulfonate, and paraffin.
〈発明の効果〉
本発明化合物は、畑地の土壌処理および茎葉処理、さら
に水田の湛水処理において問題となる種々の雑草に対し
て優れた除草効力を有し、主要作物と雑草間に優れた適
択性を示すことから除草剤の有効成分として柚々の用途
に用いることができる。<Effects of the Invention> The compound of the present invention has excellent herbicidal efficacy against various weeds that are problematic in soil treatment and foliage treatment of upland fields, as well as in flooding treatment of paddy fields, and has excellent weed control properties between major crops and weeds. Since it exhibits selectivity, it can be used as an active ingredient in herbicides.
〈実施例〉
以下、本発明を製造例、製剤例および試験例により、さ
らに詳しく説明するが、本発明はこれらの実施例に限定
されるものではない。<Examples> The present invention will be explained in more detail below using production examples, formulation examples, and test examples, but the present invention is not limited to these examples.
まず、本発明化合物の製造例を示す。First, a production example of the compound of the present invention will be shown.
製造例１ 〔本発明化合物（１）の製造〕２−アセチル
−５−（２−（４−ジフルオロメトキシフェニルチオ）
エチルクシクロヘキサン−１．３−ジオン０．８５ Ｆ
と〇−エチルヒドロキシ、Ｉ＋／７ ミニｚ！酸塩０．
１２９とを１０−のメタノールに溶かし、水酸化ナトリ
ウム０．０４ Ｆを加え、室温で一夜攪拌した。次に、
反応液を水にあけ、希塩酸を加えて酸性にした後クロロ
ホルムで抽出した。減圧下にクロロホルムを除去して得
た残渣を薄ノークロマトグラフィー（展開溶媒：酢酸エ
チル：ヘキサン＝１：５）にて処理し、２−（１−エト
キシアミ、ノエチリデン）−５−（２−（４−ジフルオ
ロメトキシフェニルチオ）エチルコシクロヘキサン−１
，３−ジオン０．１１９を得た。Production Example 1 [Production of compound (1) of the present invention] 2-acetyl-5-(2-(4-difluoromethoxyphenylthio)
Ethylcyclohexane-1,3-dione 0.85 F
and 〇-ethylhydroxy, I+/7 mini z! Acid acid 0.
129 was dissolved in 10-methanol, 0.04 F of sodium hydroxide was added, and the mixture was stirred at room temperature overnight. next,
The reaction solution was poured into water, made acidic by adding diluted hydrochloric acid, and then extracted with chloroform. The residue obtained by removing chloroform under reduced pressure was treated with thin no-chromatography (developing solvent: ethyl acetate:hexane = 1:5) to obtain 2-(1-ethoxyamide, noethylidene)-5-(2-( 4-difluoromethoxyphenylthio)ethylcocyclohexane-1
, 3-dione 0.119 was obtained.
’Ｈ−ＮＭＲ（ＣＤＣｌｓ）
δ（１）ｐｍ） １４．６５（ＩＨ，ｂｒｓ）７．１
６（４Ｈ，ＡＢｑ）６．００（ＩＨ，ｔ） ４．０７
（２Ｈ，Ｑ）２．６−１．５（７Ｈ，ｍ） １．２８
（８Ｈ，ｔ）製造例２ 〔本発明化合物（５）の製造〕
２−プロピオニル−５−（２−（４−ジフルオロメトキ
シフェニルチオ）エチルコシクロヘキサン−１，８−ジ
オン０．８５ ＰとＯ−アリルヒドロキシルアミンｍｉ
！塩０．１２９とを１０−のメタノールに溶かし、水酸
化ナトリウム０．０４９を那え、室温で一夜攪拌した。'H-NMR (CDCls) δ (1) pm) 14.65 (IH, brs) 7.1
6 (4H, ABq) 6.00 (IH, t) 4.07
(2H, Q) 2.6-1.5 (7H, m) 1.28
(8H, t) Production Example 2 [Production of compound (5) of the present invention]
2-Propionyl-5-(2-(4-difluoromethoxyphenylthio)ethylcocyclohexane-1,8-dione 0.85 P and O-allylhydroxylamine mi
! 0.129% of the salt was dissolved in 10-methanol, added with 0.049% of sodium hydroxide, and stirred overnight at room temperature.
次に、反応液を水にあけ、希塩酸を加えて酸性にした後
ジクロロメタンで抽出した。減圧下にジクロロメタンを
除去して得た残渣を薄層クロマトグラフィー（展開溶媒
；酢酸エチル：ヘキサン＝１：５）にて処理し、２−（
１−アリルオキシアミノプロピリデン）−５−（２−（
４−ジフルオロメトキシフェニルチオ）エチルコシクロ
ヘキサン−１，８−ジオンｏ、１８ノを得た。Next, the reaction solution was poured into water, made acidic by adding dilute hydrochloric acid, and extracted with dichloromethane. The residue obtained by removing dichloromethane under reduced pressure was treated with thin layer chromatography (developing solvent: ethyl acetate:hexane = 1:5) to obtain 2-(
1-allyloxyaminopropylidene)-5-(2-(
4-difluoromethoxyphenylthio)ethylcocyclohexane-1,8-dione o and 18 were obtained.
’Ｈ−ＮＭＲ（ＣＤＣ／、 ）
δ（ｐＩ）ｍ） １４．４６ （ＩＨ，ｂｒｓ）
７．２０ （４Ｈ，ＡＢｑ）ｅ、、１６（ＩＨ，ｔ）
６．８〜５．２（８Ｈ，ｍ）４．５４ （２Ｈ，ｄ）
８．１〜２．７ （４Ｈ，ｍ）２．６〜１．５ （
７Ｈ，ｍ） １．１４ （８Ｈ，ｔ）第 ２ 表
次に製剤例を示す。なお、本発明化合物は第２表の化合
物番号で示す。部は重量部である。'H-NMR (CDC/, ) δ (pI) m) 14.46 (IH, brs)
7.20 (4H,ABq)e,, 16(IH,t)
6.8-5.2 (8H, m) 4.54 (2H, d)
8.1~2.7 (4H, m) 2.6~1.5 (
7H, m) 1.14 (8H, t) Table 2 Examples of formulations are shown below. The compounds of the present invention are indicated by compound numbers in Table 2. Parts are parts by weight.
製剤例１
本発明化合物（８） 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。Formulation Example 1 50 parts of the compound of the present invention (8), 8 parts of calcium lignin sulfonate, 2 parts of sodium lauryl sulfate, and 45 parts of synthetic hydrous silicon oxide are thoroughly ground and mixed to obtain a wettable powder.
製剤例２
本発明化合物（１）〜（６）の各々１０部、ポリオキシ
エチレンスチリルフェニルエーテル１４部、ドデシルベ
ンゼンスルホン酸カルシウム６部、キシレジ視およびシ
クロへキサノン４０部をよく混合して乳剤を得る。Formulation Example 2 10 parts each of the compounds (1) to (6) of the present invention, 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate, and 40 parts of cyclohexanone were thoroughly mixed to form an emulsion. obtain.
製剤例８
本発明化合物（２）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８０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。Formulation Example 8 2 parts of the compound (2) of the present invention, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 80 parts of bentonite and 65 parts of kaolin clay were thoroughly ground and mixed, water was added and the mixture was thoroughly kneaded. Granulate and dry to obtain granules.
製剤例４
本発明化合物（１）２５ｍ、ポリオキシエチレンソルビ
タンモノオレエート８部、ＣＭＣ８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。Formulation Example 4 25 m of the compound of the present invention (1), 8 parts of polyoxyethylene sorbitan monooleate, 8 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.
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２表
の化合物番号で示し、比較対照に用いた化合物は第８表
の化合物記号で示す。Next, test examples demonstrate 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 2, and the compounds used for comparison are indicated by the compound symbols in Table 8.
第 ３ 表
また、除草効力および薬害の評価は、調査時の供試植物
（雑草および作物）の出芽および生育の状態が無処理の
それと比較して全くないしほとんど違いがないものをｒ
ＯＪとし、供試植物が完全枯死または出芽若しくは生育
が完全に抑制されているものをｒｏＪとして、０〜５の
６段階に区分し０．１．２．３．４．５で示す。Table 3 In addition, the evaluation of herbicidal efficacy and phytotoxicity is based on whether the germination and growth conditions of the test plants (weeds and crops) at the time of the survey are completely or almost different from those of untreated plants.
OJ is defined as roJ when the test plant is completely dead or its budding or growth is completely suppressed, and it is classified into 6 levels from 0 to 5 and indicated as 0.1.2.3.4.5.
試験例１ 畑地土壌表面処理試験
直径１０ＣＩ１１．深さ１０ａ１の円筒型プラスチック
ポットに畑地土壌を詰め、ヒエ、エンバクを播種し覆土
した。製剤例２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４表に
示す。Test Example 1 Upland soil surface treatment test diameter 10CI11. A cylindrical plastic pot with a depth of 10 a1 was filled with field soil, and millet and oat were sown and covered with soil. Make the test compound into an emulsion according to Formulation Example 2, dilute the specified amount with water equivalent to 10 liters per are,
The soil surface was treated with a small sprayer. After treatment, the plants were grown in a greenhouse for 20 days and their herbicidal efficacy was investigated. The results are shown in Table 4.
第 ４ 表
試験例２ 畑地草葉処理試験
直径１０備、深さ１０ａａの円筒型プラスチックポット
に畑地土壌を詰め、ヒエ、エンバク、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２
０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 4 Test Example 2 Upland Grass Treatment Test A cylindrical plastic pot with a diameter of 10 mm and a depth of 10 aa was filled with upland soil, and millet, oat, 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, and a predetermined amount of the emulsion was diluted with water containing a spreading agent equivalent to 10 liters per are.
The foliage was treated from above the plant using a small sprayer. After processing 2
The plants were grown in a greenhouse for 0 days and their herbicidal efficacy was investigated. The results are shown in Table 5.
第 ５ 表
試験例８ 水田湛水処理試験
直径８ｃｍ 、深さ１２ＣＩ＋の円筒型プラスチックポ
ットに水田土壌を詰め、タイヌビエの種子を１〜２ｃｓ
の深さに混ぜ込んだ。湛水して水田状態にした後、温室
内で育成した。６日後（タイヌビエの発生初期）に製剤
例２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、除草効力および薬害を調査した。Table 5 Test Example 8 Paddy field flooding treatment test A cylindrical plastic pot with a diameter of 8 cm and a depth of 12 CI+ was filled with paddy soil, and 1 to 2 cs of Japanese millet seeds were added.
It was mixed to a depth of . After being flooded into paddy fields, they were grown in a greenhouse. After 6 days (at the beginning of the generation of green millet), the test compound was made into an emulsion according to Formulation Example 2, a predetermined amount of the emulsion was diluted with 5 milliliters of water, and the emulsion was applied to the water surface. 20 days after treatment
The plants were grown in a greenhouse for one day and their herbicidal efficacy and phytotoxicity were investigated.
その結果を第６表に示す。The results are shown in Table 6.
第 ６ 表
試験例４ 畑地土壌処理試験
面積３３Ｘ２８ＣＩＩ＋２、深さ１１１のバットに畑地
土壌を詰め、コムギ、ノスズメノテッポウを播種し、１
〜２Ｃ１ｍの厚さに覆土した。製剤例２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７表に示す。Table 6 Test Example 4 Upland Soil Treatment Test Field soil was packed into a vat with an area of 33 x 28 CII + 2 and a depth of 111, and wheat and sycamore were sown.
It was covered with soil to a thickness of ~2C1m. The test compound was made into an emulsion according to Formulation Example 2, 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 20 days and their herbicidal efficacy was investigated. The results are shown in Table 7.
第 ７ 表
試験例５ 畑地茎葉処理試験
面積８８ Ｘ ２ Ｂ ｃｍ’ｓ深さＩＩＣＩＩのバッ
トに畑地土壌を詰め、トウモロコシ、セイバンモロコシ
、エノコログサを播種し、１８日間育成した。その後、
製剤例２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１０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、１〜２葉期で、草丈は７〜１５ａｉで
あった。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
内で行った。Table 7 Test Example 5 Upland Stalk and Leaves Treatment Test A vat with an area of 88 x 2 B cm's and a depth of IICII was filled with upland soil, and corn, Seiban sorghum, and foxtail were sown and grown for 18 days. after that,
The test compound was made into an emulsion according to Formulation Example 2, a predetermined amount of the emulsion was diluted with water equivalent to 10 liters per are containing a spreading agent, and the emulsion was uniformly applied from the top of the plant to the entire surface of the leaves using a small sprayer. . At this time, the growth conditions of weeds and crops varied depending on the grass species, but they were in the 1-2 leaf stage and the plant height was 7-15 ai. The herbicidal efficacy was investigated 20 days after the treatment. The results are shown in Table 8. Note that this test was conducted in a greenhouse throughout the entire period.
第 ８ 表
試験例６ 畑地茎葉処理試験
面積８８Ｘ２３♂、深さｌｌａｍのバットに畑地土壌を
詰め、ダイズ、ワタ、イヌビエ、セイバンモロコシ、エ
ノコログサを播種し、１８日間育成した。その後、製剤
例２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１０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。Table 8 Test Example 6 Field soil stem and leaf treatment test A vat with an area of 88 x 23♂ and a depth of llam was filled with field soil, and soybean, cotton, golden millet, Saban sorghum, and foxtail were sown and grown for 18 days. Thereafter, make an emulsion of the test compound according to Formulation Example 2, dilute the specified amount with water equivalent to 10 liters per are containing a spreading agent, and use a small sprayer to spread it uniformly over the entire stem and leaf area from the top of the plant. Processed.
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、子葉展開期〜８葉期で、草丈は７〜１５国であった
。処理２０日後に除草効力を調査した。At this time, the growth conditions of weeds and crops varied depending on the grass species, but they were from the cotyledon stage to the 8-leaf stage, and the plant height was 7 to 15 cm. The herbicidal efficacy was investigated 20 days after the treatment.
その結果を第９表に示す。なお、本試験は、全期間を通
して温室内で行った。The results are shown in Table 9. Note that this test was conducted in a greenhouse throughout the entire period.
第 ９ 表
試験例７ 水田湛水処理試験
１１５０００ａワグネルポツトに水田土壌を詰め、タイ
ヌビエの種子を１〜２ｃ＋＋１の深さに混ぜ込んだ。Table 9 Test Example 7 Paddy field flooding treatment test 115000a A Wagner pot was filled with paddy soil, and seeds of Japanese millet were mixed in at a depth of 1 to 2c++1.
湛水して水田状態にした後、３葉期のイネを移植し、温
室内で育成した。４日後に、製剤例２に準じて供試化合
物を乳剤にし、その所定量を１０ミリリツトルの水で希
釈し水面に処理し、その水深を４１とした。処理後２０
日間温室内で育成し、除草効力および薬害を調査した。After flooding the rice field to create a paddy field, three-leaf stage rice was transplanted and grown in a greenhouse. After 4 days, the test compound was made into an emulsion according to Formulation Example 2, and a predetermined amount of the emulsion was diluted with 10 milliliters of water and applied to the water surface to a water depth of 41 cm. 20 days after treatment
The plants were grown in a greenhouse for one day and their herbicidal efficacy and phytotoxicity were investigated.
その結果を第１０表に示す。なお、処理の翌日から２日
間は、１日あたり８ｃｌＮの水深に相当する量の漏水を
おこなった。The results are shown in Table 10. Note that for two days from the day after the treatment, water leaked in an amount equivalent to a water depth of 8 clN per day.
第１０表 （２７完）Table 10 (27 completed)
Claims (4)
級アルキル基、低級アルケニル基、低級アルキニル基ま
たはハロ低級アルケニル基を表わす。〕で示されるシク
ロヘキサン誘導体。(1) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ [In the formula, R^1 represents a lower alkyl group, and R^2 represents a lower alkyl group, lower alkenyl group, lower alkynyl group, or halo lower alkenyl group. represent. ] Cyclohexane derivative.
るアシルシクロヘキサン誘導体と、一般式 ＮＨ＿２ＯＲ＾２ 〔式中、Ｒ＾２は低級アルキル基、低級アルケニル基、
低級アルキニル基またはハロ低級アルケニル基を表わす
。〕 で示されるヒドロキシルアミンまたはその無機酸塩とを
反応させることを特徴とする特許請求の範囲第１項記載
のシクロヘキサン誘導体の製造法。(2) General formula ▲ Numerical formula, chemical formula, table, etc. are available ▼ [In the formula, R^1 represents a lower alkyl group. ] and an acylcyclohexane derivative represented by the general formula NH_2OR^2 [wherein R^2 is a lower alkyl group, a lower alkenyl group,
Represents a lower alkynyl group or a halo-lower alkenyl group. ] The method for producing a cyclohexane derivative according to claim 1, which comprises reacting with hydroxylamine or an inorganic acid salt thereof represented by:
体を有効成分として含有することを特徴とする除草剤。(3) A herbicide characterized by containing the cyclohexane derivative according to claim 1 as an active ingredient.
体を用いる除草方法。(4) A weeding method using the cyclohexane derivative according to claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP164988A JPH01180870A (en) | 1988-01-07 | 1988-01-07 | Cyclohexane derivative, its production, herbicide containing it, and method combating weeds using it |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP164988A JPH01180870A (en) | 1988-01-07 | 1988-01-07 | Cyclohexane derivative, its production, herbicide containing it, and method combating weeds using it |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH01180870A true JPH01180870A (en) | 1989-07-18 |
Family
ID=11507367
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP164988A Pending JPH01180870A (en) | 1988-01-07 | 1988-01-07 | Cyclohexane derivative, its production, herbicide containing it, and method combating weeds using it |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01180870A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5403812A (en) * | 1990-10-19 | 1995-04-04 | Basf Aktiengesellschaft | Unsaturated cyclohexenone oxime ethers and herbicidal compositions thereof |
-
1988
- 1988-01-07 JP JP164988A patent/JPH01180870A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5403812A (en) * | 1990-10-19 | 1995-04-04 | Basf Aktiengesellschaft | Unsaturated cyclohexenone oxime ethers and herbicidal compositions thereof |
| US5407896A (en) * | 1990-10-19 | 1995-04-18 | Basf Aktiengesellschaft | Unsaturated cyclohexenone oxime ethers and herbicidal compositions thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH042591B2 (en) | ||
| JP3156268B2 (en) | Iminothiazoline derivative, method for producing the same, herbicide containing the same as active ingredient, and intermediate for producing the same | |
| JPS63146856A (en) | Cyclohexane derivative, production thereof and herbicide comprising said derivative as active ingredient | |
| JPH04178384A (en) | Uracil derivative, production thereof and herbicide comprising the same derivative as active ingredient | |
| JPH03204867A (en) | Aralkyloxyamine derivative and herbicide | |
| JPH01180870A (en) | Cyclohexane derivative, its production, herbicide containing it, and method combating weeds using it | |
| JPH01180869A (en) | Cyclohexane derivative, its production, herbicide containing it, and method combating weeds using it | |
| JPH0436284A (en) | Diphenylfuropyrimidine derivative, its production and herbicide containing the same derivative as active ingredient | |
| JP3064371B2 (en) | Benzoxazyluracil derivative, process for producing the same and herbicide containing the same as active ingredient | |
| JPH0545593B2 (en) | ||
| JPS59155358A (en) | 4,5,6,7-tetrahydro-2h-isoindole-1,3-dione derivative, its preparation and herbicide containing said derivative as active component | |
| JP2547027B2 (en) | Cyclohexane derivative and herbicide containing it as an active ingredient | |
| JPS62277383A (en) | N-(benzoxazinyl)tetrahydrophthalimide derivative, production thereof and herbicide containing said derivative as active ingredient | |
| JPS63150281A (en) | Benzothiazolonyltrizoloxide derivative, production thereof and herbicide containing said derivative as active ingredient | |
| JPS59204181A (en) | N-phenyltetrahydroisophthalimide derivative, its preparation and herbicide containing said derivative as active component | |
| JPH01180871A (en) | Cyclohexane derivative, its production, herbicide containing it, and method combating weeds using it | |
| JPS61280471A (en) | Tetrahydrophthalimide derivative, production thereof and herbicide containing said derivative as active component | |
| JPH01102070A (en) | Carbamoyltriazole derivative, its production, and herbicide containing the same as an active ingredient | |
| JPH0322382B2 (en) | ||
| JPS61134373A (en) | Tetrahydrophthalimide derivative, production thereof, and herbicide comprising same as active ingredient | |
| JPH03169859A (en) | N-phenyltetrahydrophthalimide derivative and herbicide containing the same as active ingredient | |
| JPS60112756A (en) | Trifluoromethanesulfanilide derivative, production thereof and herbicide containing the same as active constituent | |
| JPH08193006A (en) | Herbicide composition for paddy field | |
| JPH01316306A (en) | Herbicide | |
| JPS60120854A (en) | Trifluoromethanesulfon anilide derivative, its preparation, and herbicide containing it as active ingredient |