JPH0369906B2 - - Google Patents
Info
- Publication number
- JPH0369906B2 JPH0369906B2 JP56162115A JP16211581A JPH0369906B2 JP H0369906 B2 JPH0369906 B2 JP H0369906B2 JP 56162115 A JP56162115 A JP 56162115A JP 16211581 A JP16211581 A JP 16211581A JP H0369906 B2 JPH0369906 B2 JP H0369906B2
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- formula
- ethyl
- alkyl
- oxyacetic acid
- 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 - Lifetime
Links
- -1 4-tetrahydroquinolyl Chemical group 0.000 claims description 17
- 230000002363 herbicidal effect Effects 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 239000004009 herbicide Substances 0.000 claims description 5
- HBKZWZUVLNENFH-UHFFFAOYSA-N 2-(1h-indol-2-yloxy)acetamide Chemical class C1=CC=C2NC(OCC(=O)N)=CC2=C1 HBKZWZUVLNENFH-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000005936 piperidyl group Chemical group 0.000 claims description 3
- 239000011593 sulfur Chemical group 0.000 claims description 3
- 229910052717 sulfur Chemical group 0.000 claims description 3
- YFAWSODDTKJRLA-UHFFFAOYSA-N 2-[(5-methyl-1,3-benzoxazol-2-yl)oxy]acetic acid Chemical compound CC1=CC=C2OC(OCC(O)=O)=NC2=C1 YFAWSODDTKJRLA-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 39
- 241000196324 Embryophyta Species 0.000 description 27
- 239000000203 mixture Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 239000003995 emulsifying agent Substances 0.000 description 8
- 230000006378 damage Effects 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-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
- 239000002253 acid Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 241000209094 Oryza Species 0.000 description 5
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 235000007164 Oryza sativa Nutrition 0.000 description 4
- 241000209140 Triticum Species 0.000 description 4
- 235000021307 Triticum Nutrition 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 235000009566 rice Nutrition 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 241000219146 Gossypium Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241001076438 Oxya japonica Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 235000002634 Solanum Nutrition 0.000 description 3
- 241000207763 Solanum Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 230000035784 germination Effects 0.000 description 3
- 230000012010 growth Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- LMODYJDUSCQYRS-UHFFFAOYSA-N 2-chloro-5-methyl-1,3-benzothiazole Chemical compound CC1=CC=C2SC(Cl)=NC2=C1 LMODYJDUSCQYRS-UHFFFAOYSA-N 0.000 description 2
- AVJUFHRBOJNDFG-UHFFFAOYSA-N 2-chloro-5-methyl-1,3-benzoxazole Chemical compound CC1=CC=C2OC(Cl)=NC2=C1 AVJUFHRBOJNDFG-UHFFFAOYSA-N 0.000 description 2
- TZGPACAKMCUCKX-UHFFFAOYSA-N 2-hydroxyacetamide Chemical compound NC(=O)CO TZGPACAKMCUCKX-UHFFFAOYSA-N 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- 241000234282 Allium Species 0.000 description 2
- 235000005781 Avena Nutrition 0.000 description 2
- 244000075850 Avena orientalis Species 0.000 description 2
- 235000016068 Berberis vulgaris Nutrition 0.000 description 2
- 241000335053 Beta vulgaris Species 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- 241000219122 Cucurbita Species 0.000 description 2
- 241000234653 Cyperus Species 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 235000021506 Ipomoea Nutrition 0.000 description 2
- 241000207783 Ipomoea Species 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- 241000209117 Panicum Species 0.000 description 2
- 235000006443 Panicum miliaceum subsp. miliaceum Nutrition 0.000 description 2
- 235000009037 Panicum miliaceum subsp. ruderale Nutrition 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 2
- 244000062793 Sorghum vulgare Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 239000000370 acceptor Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 238000010410 dusting Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N n-propyl alcohol Natural products CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 150000002826 nitrites Chemical class 0.000 description 2
- 239000002420 orchard Substances 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- IWFADOHGIIWDGN-UHFFFAOYSA-N 1-(2,4-dimethylpiperidin-1-yl)-2-hydroxyethanone Chemical compound CC1CCN(C(=O)CO)C(C)C1 IWFADOHGIIWDGN-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 1
- FWYULLXZQPHSAL-UHFFFAOYSA-N 2-(1,3-benzoxazol-2-yloxy)acetic acid Chemical compound C1=CC=C2OC(OCC(=O)O)=NC2=C1 FWYULLXZQPHSAL-UHFFFAOYSA-N 0.000 description 1
- JNQVLKWNKVMFBN-UHFFFAOYSA-N 2-hydroxy-n,n-dimethylacetamide Chemical compound CN(C)C(=O)CO JNQVLKWNKVMFBN-UHFFFAOYSA-N 0.000 description 1
- NJBCRXCAPCODGX-UHFFFAOYSA-N 2-methyl-n-(2-methylpropyl)propan-1-amine Chemical compound CC(C)CNCC(C)C NJBCRXCAPCODGX-UHFFFAOYSA-N 0.000 description 1
- FYRBHLFWWSLQGB-UHFFFAOYSA-N 2-methyl-n-propylpropanamide Chemical compound CCCNC(=O)C(C)C FYRBHLFWWSLQGB-UHFFFAOYSA-N 0.000 description 1
- WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 description 1
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- 108010088751 Albumins Proteins 0.000 description 1
- RGCKGOZRHPZPFP-UHFFFAOYSA-N Alizarin Natural products C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 description 1
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- 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
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 244000193174 agave Species 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- HFVAFDPGUJEFBQ-UHFFFAOYSA-M alizarin red S Chemical compound [Na+].O=C1C2=CC=CC=C2C(=O)C2=C1C=C(S([O-])(=O)=O)C(O)=C2O HFVAFDPGUJEFBQ-UHFFFAOYSA-M 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000004067 bulking agent Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 244000118869 coast club rush Species 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000002837 defoliant Substances 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 239000012973 diazabicyclooctane Substances 0.000 description 1
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 1
- UZBQIPPOMKBLAS-UHFFFAOYSA-N diethylazanide Chemical compound CC[N-]CC UZBQIPPOMKBLAS-UHFFFAOYSA-N 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 239000010459 dolomite Substances 0.000 description 1
- 229910000514 dolomite Inorganic materials 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000003630 growth substance Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- DCYOBGZUOMKFPA-UHFFFAOYSA-N iron(2+);iron(3+);octadecacyanide Chemical compound [Fe+2].[Fe+2].[Fe+2].[Fe+3].[Fe+3].[Fe+3].[Fe+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] DCYOBGZUOMKFPA-UHFFFAOYSA-N 0.000 description 1
- 238000003973 irrigation Methods 0.000 description 1
- 230000002262 irrigation Effects 0.000 description 1
- 229960004592 isopropanol Drugs 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000004579 marble Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 239000011785 micronutrient Substances 0.000 description 1
- 235000013369 micronutrients Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- IXHFNEAFAWRVCF-UHFFFAOYSA-N n,2-dimethylpropanamide Chemical compound CNC(=O)C(C)C IXHFNEAFAWRVCF-UHFFFAOYSA-N 0.000 description 1
- QSOCODZVGPDGDA-UHFFFAOYSA-N n,3-dimethylbutan-1-amine Chemical compound CNCCC(C)C QSOCODZVGPDGDA-UHFFFAOYSA-N 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- HIPXPABRMMYVQD-UHFFFAOYSA-N n-benzylbutan-1-amine Chemical compound CCCCNCC1=CC=CC=C1 HIPXPABRMMYVQD-UHFFFAOYSA-N 0.000 description 1
- HVAAHUDGWQAAOJ-UHFFFAOYSA-N n-benzylethanamine Chemical compound CCNCC1=CC=CC=C1 HVAAHUDGWQAAOJ-UHFFFAOYSA-N 0.000 description 1
- RNDFRWFHFZMEBE-UHFFFAOYSA-N n-benzylprop-2-ynamide Chemical compound C#CC(=O)NCC1=CC=CC=C1 RNDFRWFHFZMEBE-UHFFFAOYSA-N 0.000 description 1
- OUMBFMLKPJUWDQ-UHFFFAOYSA-N n-benzylpropan-1-amine Chemical compound CCCNCC1=CC=CC=C1 OUMBFMLKPJUWDQ-UHFFFAOYSA-N 0.000 description 1
- MWZXRLJDNKCYOQ-UHFFFAOYSA-N n-butan-2-ylbutan-1-amine Chemical compound CCCCNC(C)CC MWZXRLJDNKCYOQ-UHFFFAOYSA-N 0.000 description 1
- GZAROOOHRGKEPC-UHFFFAOYSA-N n-butyl-2-methylpropanamide Chemical compound CCCCNC(=O)C(C)C GZAROOOHRGKEPC-UHFFFAOYSA-N 0.000 description 1
- FNLUJDLKYOWMMF-UHFFFAOYSA-N n-ethyl-2-methylpropan-1-amine Chemical compound CCNCC(C)C FNLUJDLKYOWMMF-UHFFFAOYSA-N 0.000 description 1
- QHCCDDQKNUYGNC-UHFFFAOYSA-N n-ethylbutan-1-amine Chemical compound CCCCNCC QHCCDDQKNUYGNC-UHFFFAOYSA-N 0.000 description 1
- XCVNDBIXFPGMIW-UHFFFAOYSA-N n-ethylpropan-1-amine Chemical compound CCCNCC XCVNDBIXFPGMIW-UHFFFAOYSA-N 0.000 description 1
- RIVIDPPYRINTTH-UHFFFAOYSA-N n-ethylpropan-2-amine Chemical compound CCNC(C)C RIVIDPPYRINTTH-UHFFFAOYSA-N 0.000 description 1
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
- OLLZXQIFCRIRMH-UHFFFAOYSA-N n-methylbutanamide Chemical compound CCCC(=O)NC OLLZXQIFCRIRMH-UHFFFAOYSA-N 0.000 description 1
- UOIWOHLIGKIYFE-UHFFFAOYSA-N n-methylpentan-1-amine Chemical compound CCCCCNC UOIWOHLIGKIYFE-UHFFFAOYSA-N 0.000 description 1
- IPBXLJFBVNLKFE-UHFFFAOYSA-N n-methylpentan-2-amine Chemical compound CCCC(C)NC IPBXLJFBVNLKFE-UHFFFAOYSA-N 0.000 description 1
- WBVNBTCOCIGBDL-UHFFFAOYSA-N n-methylprop-2-ynamide Chemical compound CNC(=O)C#C WBVNBTCOCIGBDL-UHFFFAOYSA-N 0.000 description 1
- GVWISOJSERXQBM-UHFFFAOYSA-N n-methylpropan-1-amine Chemical compound CCCNC GVWISOJSERXQBM-UHFFFAOYSA-N 0.000 description 1
- XHFGWHUWQXTGAT-UHFFFAOYSA-N n-methylpropan-2-amine Chemical compound CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 1
- VLSTXUUYLIALPB-UHFFFAOYSA-N n-propan-2-ylpropan-1-amine Chemical compound CCCNC(C)C VLSTXUUYLIALPB-UHFFFAOYSA-N 0.000 description 1
- TUDFZSGUEDLTJC-UHFFFAOYSA-N n-propylbutanamide Chemical compound CCCNC(=O)CCC TUDFZSGUEDLTJC-UHFFFAOYSA-N 0.000 description 1
- VACPZDQXUAOTFR-UHFFFAOYSA-N n-tert-butylbutan-1-amine Chemical compound CCCCNC(C)(C)C VACPZDQXUAOTFR-UHFFFAOYSA-N 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- 230000008654 plant damage Effects 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 229960003351 prussian blue Drugs 0.000 description 1
- 239000013225 prussian blue Substances 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 244000045561 useful plants Species 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/06—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing isoquinuclidine ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
本発明は新規なメチル置換したベンズアゾール
−２−イル−オキシ酢酸アミド、および除草剤と
してのその使用に関するものである。
たとえば、ベンゾキサゾール−２−イル−オキ
シ酢酸１，２，３，４−テトラヒドロキノリドの
ような、ある種の置換したカルボン酸アミドが除
草活性を有していることは既に知られている（西
ドイツ特許出願公開明細書2903966号およびヨー
ロツパ特許明細書5501号参照）。しかしながら、
これらの化合物の除草性は、それらの作用の水準
および選択性の点で、必ずしも満足できるもので
はない。
式
式中で、
Ｘは酸素または硫黄を表わし、
Ｒはメチルを表わし、
R1はC1〜C5−アルキル、C3〜C5−アルケニル
またはC3〜C5−アルキニルを表わし、且つR2は
C1〜C5−アルキル、C3〜C5−アルケニル、フエ
ニル−C1〜C2−アルキルまたはフエニルを表わ
し、
あるいは式中で
R1およびR2の両基は、それらが結合している
窒素原子と共に、ピペリジルおよび１，２，３，
４−テトラヒドロキノリルなる系列からの、場合
によつてはメチルおよび／またはエチルによつて
置換してある基、あるいは下記の基：
The present invention relates to novel methyl-substituted benzazol-2-yl-oxyacetic acid amides and their use as herbicides. For example, it is already known that certain substituted carboxylic acid amides, such as benzoxazol-2-yl-oxyacetic acid 1,2,3,4-tetrahydroquinolide, have herbicidal activity. (See West German Patent Application No. 2903966 and European Patent Application No. 5501). however,
The herbicidal properties of these compounds are not always satisfactory in terms of their level of action and selectivity. formula In the formula, X represents oxygen or sulfur, R represents methyl, R1 represents C1 - C5 -alkyl, C3 - C5 -alkenyl or C3 - C5 -alkynyl, and R2 teeth
represents C1 - C5 -alkyl, C3 - C5 -alkenyl, phenyl- C1 - C2 -alkyl or phenyl, or in the formula both R1 and R2 are Along with the nitrogen atom, piperidyl and 1,2,3,
A radical from the 4-tetrahydroquinolyl series, optionally substituted by methyl and/or ethyl, or the following radicals:
【式】
の置換したベンゾアゾール−２−イル−オキシ酢
酸アミドがここに見出された。
式（）の新規化合物は、式
式中で
R1およびR2は前記の意味を有する、
のヒドロキシ酢酸アミドを、必要に応じ酸受容剤
の存在において且つ必要に応じ希釈剤の存在にお
いて、式
式中で
Ｒは前記の意味を有し且つ
Halは塩素または臭素を表わす、
の置換した２−ハロゲノ−ベンズアゾールと反応
せしめることによつて取得することができる。
式（）の新規な置換したベンズアゾール−２
−イル−オキシ酢酸アミドは、強力な除草活性に
よつて特徴的であり、且つ場合によつては有用な
植物の生長に影響をも及ぼす。
驚くべきことに、本発明による式（）の化合
物は、この技術分野で公知の類似の構造と同種の
作用を有する化合物よりも強力な除草作用を表わ
す。単子葉雑草に対するきわめて良好な作用に加
えて、これらの化合物は双子葉雑草に対する良好
な除草作用とワタ、ダイズ、ビートおよび、たと
えばコムギのような、各種の穀類に対する選択性
をも表わす。それ故、これらの化合物は、この分
野に価値ある進歩をもたらすものといえる。
本発明による式の置換したベンズアゾール−
２−イル−オキシ酢酸アミドの挙げることのでき
る例は以下のものである：５−メチル−ベンズチ
アゾール−２−イル−オキシ酢酸および５−メチ
ル−ベンゾキシアゾール−２−イル−オキシ酢酸
のジメチルアミド、ジエチルアミド、ジ−ｎ−プ
ロピルアミド、ジ−イソ−プロピルアミド、ジ−
ｎ−プチルアミド、ジ−イソブチルアミド、Ｎ−
メチル−ｎ−プロピルアミド、Ｎ−メチル−イソ
プロピルアミド、Ｎ−メチル−ｎ−ブチルアミ
ド、Ｎ−メチル−イソブチルアミド、Ｎ−メチル
−sec−ブチルアミド、Ｎ−メチル−ｔ−ブチル
アミド、Ｎ−メチル−ｎ−ペンチルアミド、Ｎ−
メチル−イソペンチルアミド、Ｎ−メチル−sec
−ペンチルアミド、Ｎ−エチル−ｎ−プロピルア
ミド、Ｎ−エチル−イソプロピルアミド、Ｎ−エ
チル−ｎ−ブチルアミド、Ｎ−エチル−イソブチ
ルアミド、Ｎ−エチル−sec−ブチルアミド、Ｎ
−エチル−ｔ−ブチルアミド、Ｎ−ｎ−プロピル
−イソプロピルアミド、Ｎ−ｎ−プロピル−ｎ−
ブチルアミド、Ｎ−ｎ−プロピル−イソブチルア
ミド、Ｎ−ｎ−プロピル−sec−ブチルアミド、
Ｎ−ｎ−プロピル−ｔ−ブチルアミド、Ｎ−ｎ−
ブチル−イソブチルアミド、Ｎ−ｎ−ブチル−
sec−ブチルアミド、Ｎ−ｎ−ブチル−ｔ−ブチ
ルアミド、ジアリルアミド、ジプロパルギルアミ
ド、Ｎ−メチル−プロパルギルアミド、Ｎ−ベン
ジル−プロパルギルアミド、Ｎ−メチル−（１−
メチル−プロパルギル）−アミド、Ｎ−メチル−
（１，１−ジメチル−プロパルギル）−アミド、Ｎ
−メチル−Ｎ−ベンジルアミド、Ｎ−エチル−Ｎ
−ベンジルアミド、Ｎ−プロピル−Ｎ−ベンジル
アミド、Ｎ−ブチル−Ｎ−ベンジルアミド、ピペ
リジド、２−メチル−ピペリジド、３−メチル−
ピペリジド、４−メチル−ピペリジド、２，４，
６−トリメチル−ピペリジド、２−エチル−ピペ
リジド、４−エチル−ピペリジド、３，４−ジメ
チルピペリジド、１，２，３，４−テトラヒドロ
キノリドおよび２−メチル−１，２，３，４−テ
トラヒドロキノリド
たとえば出発物質として２−クロロ−５−メチ
ル−ベンズチアゾールとヒドロキシ酢酸ジメチル
アミドを用いる場合は、本発明による方法におけ
る反応の経過は、下式によつて表わすことができ
る。
出発物質として使用すべき式（）のヒドロキ
シ酢酸アミドは既に公知である（西ドイツ特許出
願公開明細書2904490号および西ドイツ特許出願
公開明細書2903966号並びにヨーロツパ特許5501
号参照）。
出発物質として使用すべき式（）の２−ハロ
ゲノ−ベンズアゾールもまた同様に公知である
（J.Org.Chem.，12（1947）、718〜725；アメリカ
合衆国特許2659730号およびアメリカ合衆国特許
3284294号参照）。
挙げることができる例は次のものである：２−
クロロ−５−メチル−ベンゾキサゾール、２−ク
ロロ−５−メチル−ベンズチアゾール。
本発明による方法は適当な溶剤または希釈剤を
使用して行なうことが好ましい。使用可能な溶剤
または希釈剤は、水のほか、ほとんどすべての有
機溶剤である。これらは、特に、たとえばメタノ
ール、エタノール、ｎ−およびイソ−プロパノー
ル、並びにｎ−、イソ−、sec−およびｔ−ブタ
ノールのようなアルコール類、たとえばジプロピ
ルエーテルおよびジブチルエーテル、グリコール
ジメチルエーテルおよびジグリコールジメチルエ
ーテル、テトラヒドロフランおよびジオキサンの
ようなエーテル類、たとえばアセトン、メチルエ
チルケトン、メチルイソプロピルケトンおよびメ
チルイソブチルケトンのようなケトン類、たとえ
ばアセトニトリルおよびプロピオニトリルのよう
なニトリル類、並びに、たとえばジメチルホルム
アミドおよびジメチルアセトアミドのようなカル
ボン酸アミド類を包含する。
本発明による方法における酸受容剤としては、
一般に使用することができるほとんどすべての酸
結合剤を使用することができる。これらの酸結合
剤は、特に、たとえば水酸化ナトリウムおよび水
酸化カリウム並びに酸化カルシウムまたは水酸化
カルシウムのような、アルカリ金属水酸化物およ
び酸化物並びにアルカリ土類金属水酸化物および
酸化物、たとえば炭酸ナトリウム、炭酸カリウム
および炭酸カルシウムのようなアルカリ金属炭酸
化物並びにアルカリ土類金属炭酸化物、たとえば
ナトリウムメチラート、エチラートおよびｔ−ブ
チラート並びにカリウムメチラート、エチラート
およびｔ−ブチラートのようなアルカリ金属アル
コラート、且つまた、たとえばトリエチルアミ
ン、ジメチルアニリン、ジメチルベンジルアミ
ン、ピリジン、ジアザビシクロオクタンおよびジ
アザビシクロウンデセンのような脂肪族、芳香族
または複素環式アミンを包含する。
反応温度は広い範囲内で変えることができる。
一般に、反応は０〜80℃、好ましくは10〜50℃に
おいて行なわれる。
本発明による方法は一般に常圧下に行なわれ
る。
式（）および（）の出発化合物および酸結
合剤は一般に、本発明による方法を遂行するため
には、ほぼ等モル量で使用する。反応は一般に適
当な希釈剤中で行ない、且つ反応混合物を必要な
温度で数時間にわたつて撹拌する。
後処理は常法によつて行なうことができる：
結晶性の生成物は、反応混合物を水中に注下し
たのち、必要に応じ混合物を塩酸、硫酸または酢
酸によつて中和し且つ結晶を別したのち、再結
晶することにより比較的純粋な形態で取得するこ
とができる。
生成物が室温において油状であるときは、必要
に応じ濃縮後に、反応混合物を、たとえば塩化メ
チレンのような、ほとんど水と混合しない有機溶
剤によつて希釈し、希酸および水によつて混合物
を洗浄し、それを乾燥および過したのち、液
から減圧下に注意深く溶剤を留去することによつ
て、比較的純粋な形態で取得することができる。
生成物のキヤラクタリゼーシヨンには融点または
屈折率を使用する。
本発明による活性化合物は植物の生長に影響を
与え、それ故、落葉剤、乾燥剤、広葉植物を枯ら
すための薬剤および発芽禁止剤として、且つ特に
雑草駆除剤として使用することができる。雑草と
は、もつとも広い意味において、生長が望ましく
ない場所に生えているあらゆる植物を意味する。
本発明による物質が全面的除草剤または選択的除
草剤の何れとして作用するかは、本質的に使用す
る量に依存する。
本発明による活性化合物は、たとえば、以下の
植物に関連して使用することができる：
次の属の双子葉雑草：カラシ属（Sinapis）、マ
メグンバイナズナ属（Lepidium）、ヤエムグラ属
（Galium）、ハコベ属（Stellaria）、シカギク属
（Matricaria）、カミツレモドキ属（Anthemis）、
ガリンソガ属（Galinsoga）、アカザ属
（Chenopodium）、イラクサ属（Urtica）、キオン
属（Senecio）、ヒユ属（Amaranthus）、スベリ
ヒユ属（Portulaca）、オナモミ属（Xanthium）、
ヒルガオ属（Convolvulus）、サツマイモ属
（Ipomoea）、タデ属（Polygonum）、セスバニア
属（Sesbania）、ブタクサ属（Ambrosia）、アザ
ミ属（Cirsium）、ヒレアザミ属（Carduus）、ノ
ゲシ属（Sonchus）、ナス属（Solanum）、イヌガ
ラシ属（Rorippa）、キカシグサ属（Rotala）、ア
ゼナ属（Lindernia）、ラミウム属（Lamium）、
クワガタソウ属（Veronica）、イチビ属
（Abutilon）、エメクス属（Emex）、チヨウセン
アサガオ属（Datura）、スミレ属（Viola）、チシ
マオドリコ属（Galeopsis）、ケシ属（Papaver）
およびヤグルマギク属（Centaurea）。
次の属の双子葉栽培植物：ワタ属
（Gossypium）、ダイズ属（Glycine）、フダンソ
ウ属（Beta）、ニンジン属（Daucus）、インゲン
マメ属（Phaseolus）、エンドウ属（Pisum）、ナ
ス属（Solanum）、アマ属（Linum）、サツマイ
モ属（Ipomoea）、ソラマメ属（Vicia）、タバコ
属（Nicotiana）、トマト属（Lycopersicon）、ラ
ツカセイ属（Arachis）、アブラナ属
（Brassica）、アキノノゲシ属（Lactuca）、キユ
ウリ属（Cucumis）およびウリ属（Cuburbita）。
次の属の単子葉雑草：ヒエ属（Echinochloa）、
エノコログサ属（Setaria）、キビ属（Panicum）、
メヒシバ属（Digitaria）、アワガリエ属
（Phleum）、スズメノカタビラ属（Poa）、ウシノ
ケグサ属（Festuca）、オヒシバ属（Eleusine）、
ブラキアリア属（Brachiaria）、ドクムギ属
（Lolium）、スズメノチヤヒキ属（Bromus）、カ
ラスムギ属（Avena）、カヤツリグサ属
（Cyperus）、モロコシ属（Sorghum）、カモジグ
サ属（Agropyron）、シノドン属（Chnodon）、
ミズアオイ属（Monochoria）、テンツキ属
（Fimbristylis）、オモダカ属（Sagittaria）、ハリ
イ属（Eleocharis）、ホタルイ属（Scirpus）、パ
スパルム属（Paspalum）、カモノハシ属
（Ischaemum）、スフエノクレア属
（Sphenoclea）、ダクチロクテニウム
（Dactyloctenium）、ヌカボ属（Agrostis）、スズ
メノテツポウ属（Alopecurus）およびアペラ属
（Apera）。
次の属の単子葉栽培植物：イネ属（Oryza）、
トウモロコシ属（Zea）、コムギ属（Triticum）、
オオムギ属（Hordeum）、カラスムギ属
（Avena）、ライムギ属（Secale）、モロコシ属
（Sorghum）、キビ属（Panicum）、サトウキビ属
（Saccharum）、アナナス属（Ananas）、クサス
ギカズラ属（Asparagus）およびネギ属
（Allium）。
しかしながら、本発明による活性化合物の使用
は決してこれらの属に限定されることはなく、同
様にして他の植物にも拡張することができる。
本発明の化合物は濃度に依存して、たとえば、
工業地域および鉄道線路上、樹木の植込みが存在
するかまたは存在しない道路および広場上の雑草
の完全駆除に対して適している。同様に、本発明
の化合物は、多年生の裁培植物、たとえば植林、
装飾用樹木の植込み、果樹園、ブドウ園、柑橘類
の畑、クルミ園、バナナ農園、コーヒー農園、茶
農園、ゴム農園、油ヤシ農園、ココア農園、甘い
果物の植込みおよびホツプ農場中の雑草を除くた
め、および多年生栽培植物中の雑草の選択的な駆
除のために使用することができる。
本発明による活性化合物は、単子葉雑草に対す
るきわめて良好な作用に加えて、双子葉雑草に対
する良好な除草作用をも表わす。本発明による活
性化合物は、各種の作物において、なかんずく、
ワタ、ダイズ、ビートおよび穀類、たとえばコム
ギおよびイネにおいて、選択的に使用することが
できる。
活性化合物は、たとえば液剤、乳剤、湿潤性粉
末、懸濁剤、粉剤、散剤、ペースト剤、可溶性粉
剤、粒剤、濃厚懸濁−乳剤、活性化合物を含浸さ
せた天然および合成材料、重合体物質中きわめて
微細なカプセルのような、通常の配合物に転換さ
せることができる。
これらの配合物は、公知の方法によつて、たと
えば活性化合物を、場合によつては界面活性剤、
すなわち乳化剤および／または分散剤、および／
または発泡剤の使用と共に、増量剤すなわち、液
体溶剤および／または固体担体と混合することに
よつて、製造することができる。増量剤として水
を使用する場合には、補助溶剤として有機溶剤を
も使用することができる。液体溶剤としては、主
として以下のものが適当である：たとえばキシレ
ン、トルエンまたはアルキルナフタレン類のよう
な芳香族類、たとえばクロロベンゼン、クロロエ
チレン類または塩化メチレンのような、塩素化芳
香族または塩素化脂肪族炭化水素、たとえばシク
ロヘキサンまたはパラフイン類、たとえば鉱油留
分のような脂肪族炭化水素、たとえばブタノール
またはグリコールのようなアルコール類およびそ
れらのエーテル並びにエステル類、たとえばアセ
トン、メチルエチルケトン、メチルイソブチルケ
トンまたはシクロヘキサノンのようなケトン類、
たとえばジメチルホルムアミドおよびジメチルス
ルホキシドのような強度に極性の溶剤、ならびに
水。
固体担体としては以下のものが適当である：た
とえば、カオリン、クレー、タルク、チヨーク、
石英、アタパルジヤイト、モンモリロナイトまた
は珪藻土のような、粉砕した天然鉱物、および、
たとえば高度に分散させた珪酸、アルミナおよび
珪酸塩のような、粉砕した合成鉱物；粒剤用の固
体担体としては以下のものが適当である：たとえ
ば方解石、大理石、軽石、海泡石および白雲石の
ような粉砕し且つ分級した天然岩石、並びに無機
および有機あら粉の合成顆粒、およびおがくず、
やし殻、とうもろこし穂軸およびたばこの茎のよ
うな有機材料の小粒；乳化剤および／または泡立
て剤としては以下のものが適している：たとえ
ば、ポリオキシエチレン−脂肪酸エステル、ポリ
オキシエチレン−脂肪アルコールエーテル、たと
えばアルキルアリールポリグリコールエーテル、
スルホン酸アルキル、硫酸アルキル、スルホン酸
アリールおよびアルブミン加水分解生成物のよう
な非イオンおよび陰イオン乳化剤；分散剤として
は以下のものが適当である：たとえばリグニン−
亜硫酸廃液およびメチルセルロース。
カルボキシメチルセルロースおよび粉末状粒状
またはラテツクス状の、たとえばアラビアゴム、
ポリビニルアルコールおよびポリ酢酸ビニルのよ
うな、天然および合成重合体の如き接着剤を、配
合物中で使用することができる。
無機顔料、たとえば酸化鉄、酸化チタンおよび
プルシアンブルー、並びに有機染料、たとえばア
リザリン染料、アゾ染料および金属フタロシアニ
ン染料、のような着色剤、および、たとえば鉄、
マンガン、ホウ素、銅、コバルト、モリブデンお
よび亜鉛の塩類のような微量栄養物を使用するこ
とも可能である。
配合物は一般に0.1〜95重量％、好ましくは0.5
〜90重量％の活性化合物を含有している。
本発明による活性化合物は、そのままで、また
は配合物の形態として、更には、仕上つた配合物
またはタンク混合が可能な既知の除草剤との混合
物として、雑草と戦かうために使用することがで
きる。たとえば殺菌剤、殺虫剤、殺ダニ剤、殺線
虫剤、駆鳥剤、生長調節剤、植物栄養剤および土
壌構造を改良する薬剤のような、他の公知の活性
化合物との混合物もまた使用することができる。
活性化合物は、そのままで、それらの配合物の
形態で、または、更に希釈することによつてそれ
らから調製した、たとえば即座に使用できる液
剤、懸濁剤、乳剤、粉剤、ペースト剤および粒剤
のような使用形態で、用いることができる。これ
らは常法によつて、たとえば潅水、噴霧、アトマ
イジング、散粉、ダスチングによつて使用する。
本発明による活性化合物は、植物の発芽の前後
の何れかに、施用することができる。植物の発芽
前に、すなわち発芽前方法によつて、施用するこ
とが好ましい。播種前に土中に混入することもで
きる。
使用する活性化合物の量は広い範囲内で変える
ことができる。使用量は本質的に所望する効果の
本質に依存する。一般に、使用する量は、１ヘク
タール当り0.1〜10Kg、好ましくは0.1〜５Kgの活
性化合物である。
場合によつては、本発明による化合物は、ある
使用濃度において、生長調節作用をも表わす。
以下の実施例は本発明を例証するためのもので
ある。
製造実施例
実施例 １
8.4ｇ（0.05モル）の２−クロロ−５−メチル
−ベンゾキサゾールを8.5ｇ（0.05モル）のヒド
ロキシ酢酸２，４−ジメチルピペリジド、5.6ｇ
（0.05モル）のカリウムｔ−ブチラートおよび100
mlのｔ−ブタノールの混合物に対して室温（20±
10℃）で加える。この混合物を室温で３時間撹拌
し、200mlの塩化メチレンで希釈し、2Nの塩酸に
より、次いで水によつて洗浄し、乾燥したのち
過する。液から減圧下に溶剤を注意しながら留
去する。残留物として、1.5375の屈折率n21 Dを有
し且つ５−メチル−ベンゾキサゾール−２−イル
−オキシ酢酸２，４−ジメチル−ピペリジドを含
有する7.5ｇの油状の生成物を取得する。
実施例１と同様にして、下表に示す(1)の化合物
を製造することができる。
なお下記表中、実施例番号15〜20および24の化
合物は参考化合物である。A substituted benzazol-2-yl-oxyacetamide of the formula has now been found. A new compound of formula () has the formula A hydroxyacetamide of the formula, in which R 1 and R 2 have the meanings given above, optionally in the presence of an acid acceptor and optionally in the presence of a diluent, is added to a compound of the formula It can be obtained by reacting with a substituted 2-halogeno-benzazole in which R has the abovementioned meaning and Hal represents chlorine or bromine. Novel substituted benzazole-2 of formula ()
-yl-oxyacetic acid amides are characterized by a strong herbicidal activity and in some cases also influence the growth of useful plants. Surprisingly, the compounds of formula () according to the invention exhibit a more potent herbicidal action than the compounds of similar structure and homologous action known in the art. In addition to a very good action against monocotyledonous weeds, these compounds also exhibit good herbicidal action against dicotyledonous weeds and selectivity against various cereal crops, such as cotton, soybeans, beets and, for example, wheat. These compounds therefore represent a valuable advance in this field. Substituted benzazoles of the formula according to the invention -
Examples which may be mentioned of 2-yl-oxyacetic acid amides are: 5-methyl-benzthiazol-2-yl-oxyacetic acid and dimethyl of 5-methyl-benzoxyazol-2-yl-oxyacetic acid. amide, diethylamide, di-n-propylamide, di-iso-propylamide, di-
n-butylamide, di-isobutylamide, N-
Methyl-n-propylamide, N-methyl-isopropylamide, N-methyl-n-butyramide, N-methyl-isobutyramide, N-methyl-sec-butyramide, N-methyl-t-butyramide, N-methyl-n -Pentylamide, N-
Methyl-isopentylamide, N-methyl-sec
-pentylamide, N-ethyl-n-propylamide, N-ethyl-isopropylamide, N-ethyl-n-butylamide, N-ethyl-isobutylamide, N-ethyl-sec-butyramide, N
-ethyl-t-butyramide, N-n-propyl-isopropylamide, N-n-propyl-n-
Butyramide, N-n-propyl-isobutyramide, N-n-propyl-sec-butyramide,
N-n-propyl-t-butyramide, N-n-
Butyl-isobutyramide, N-n-butyl-
sec-butylamide, N-n-butyl-t-butylamide, diallylamide, dipropargylamide, N-methyl-propargylamide, N-benzyl-propargylamide, N-methyl-(1-
Methyl-propargyl)-amide, N-methyl-
(1,1-dimethyl-propargyl)-amide, N
-Methyl-N-benzylamide, N-ethyl-N
-benzylamide, N-propyl-N-benzylamide, N-butyl-N-benzylamide, piperidide, 2-methyl-piperidide, 3-methyl-
piperidide, 4-methyl-piperidide, 2,4,
6-trimethyl-piperidide, 2-ethyl-piperidide, 4-ethyl-piperidide, 3,4-dimethylpiperidide, 1,2,3,4-tetrahydroquinolide and 2-methyl-1,2,3,4 -Tetrahydroquinolide If, for example, 2-chloro-5-methyl-benzthiazole and hydroxyacetic acid dimethylamide are used as starting materials, the course of the reaction in the process according to the invention can be represented by the following formula. The hydroxyacetic acid amides of the formula ( ) to be used as starting materials are already known (see DE 2904490 and DE 2903966 and European patent 5501).
(see issue). The 2-halogeno-benzazoles of the formula () to be used as starting materials are likewise known (J.Org.Chem., 12 (1947), 718-725; U.S. Pat. No. 2,659,730 and U.S. Pat.
(See No. 3284294). Examples that may be mentioned are: 2-
Chloro-5-methyl-benzoxazole, 2-chloro-5-methyl-benzthiazole. The process according to the invention is preferably carried out using suitable solvents or diluents. Solvents or diluents that can be used are, in addition to water, almost all organic solvents. These include, in particular, alcohols such as methanol, ethanol, n- and iso-propanol, and n-, iso-, sec- and tert-butanol, such as dipropyl and dibutyl ether, glycol dimethyl ether and diglycol dimethyl ether. , ethers such as tetrahydrofuran and dioxane, ketones such as acetone, methyl ethyl ketone, methyl isopropyl ketone and methyl isobutyl ketone, nitrites such as acetonitrile and propionitrile, and nitrites such as dimethylformamide and dimethylacetamide. This includes carboxylic acid amides. Acid acceptors in the method according to the invention include:
Almost any commonly available acid binder can be used. These acid binders include, in particular, alkali metal hydroxides and oxides and alkaline earth metal hydroxides and oxides, such as, for example, sodium and potassium hydroxide and calcium oxide or calcium hydroxide, such as carbonate. alkali metal carbonates and alkaline earth metal carbonates such as sodium, potassium carbonate and calcium carbonate, such as sodium methylate, ethylate and t-butyrate and alkali metal alcoholates such as potassium methylate, ethylate and t-butylate, and Also included are aliphatic, aromatic or heterocyclic amines such as, for example, triethylamine, dimethylaniline, dimethylbenzylamine, pyridine, diazabicyclooctane and diazabicycloundecene. The reaction temperature can be varied within a wide range.
Generally, the reaction is carried out at a temperature of 0-80°C, preferably 10-50°C. The process according to the invention is generally carried out under normal pressure. The starting compounds of formulas () and () and the acid binder are generally used in approximately equimolar amounts to carry out the process according to the invention. The reaction is generally carried out in a suitable diluent and the reaction mixture is stirred at the required temperature for several hours. Work-up can be carried out by conventional methods: For crystalline products, the reaction mixture is poured into water, the mixture is optionally neutralized with hydrochloric acid, sulfuric acid or acetic acid, and the crystals are separated. It can then be obtained in a relatively pure form by recrystallization. If the product is oily at room temperature, dilute the reaction mixture, after concentration if necessary, with a sparingly water-immiscible organic solvent, such as methylene chloride, and dilute the mixture with dilute acid and water. After washing, drying and filtering it, it can be obtained in relatively pure form by carefully distilling off the solvent under reduced pressure from the liquid.
Melting point or refractive index is used for product characterization. The active compounds according to the invention influence the growth of plants and can therefore be used as defoliants, desiccants, agents for killing broad-leaved plants and germination inhibitors, and in particular as weed killers. Weed, in its broadest sense, refers to any plant that grows in an area where its growth is undesirable.
Whether the substances according to the invention act as general herbicides or selective herbicides depends essentially on the amount used. The active compounds according to the invention can be used, for example, in connection with the following plants: Dicotyledonous weeds of the following genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis,
Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium,
Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Cardus, Sonchus, Solanum (Solanum), Rorippa, Rotala, Lindernia, Lamium,
Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver
and Centaurea. Dicotyledonous plants of the following genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum. , Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucurbita Genus (Cucumis) and Genus Cucurbita (Cuburbita). Monocotyledonous weeds of the following genera: Echinochloa,
Setaria, Panicum,
Digitaria, Phleum, Poa, Festuca, Eleusine,
Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Chnodon,
Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyl Dactyloctenium, Agrostis, Alopecurus and Apera. Monocotyledonous cultivated plants of the following genera: Oryza,
Maize (Zea), Triticum (Triticum),
Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus and Allium (Allium). However, the use of the active compounds according to the invention is in no way restricted to these genera, but can be extended to other plants as well. Depending on the concentration, the compounds of the invention may e.g.
Suitable for complete weed control in industrial areas and on railway lines, roads and squares with or without tree plantings. Similarly, the compounds of the invention may be used in perennial cultivated plants, such as plantations,
Eliminating weeds in ornamental tree plantings, orchards, vineyards, citrus fields, walnut orchards, banana plantations, coffee plantations, tea plantations, rubber plantations, oil palm plantations, cocoa plantations, sweet fruit plantations and hop farms. for selective control of weeds in perennial cultivated plants. In addition to a very good action against monocotyledonous weeds, the active compounds according to the invention also exhibit a good herbicidal action against dicotyledonous weeds. The active compounds according to the invention can be used in various crops, inter alia,
It can be used selectively in cotton, soybeans, beets and cereals such as wheat and rice. The active compounds can be used, for example, in solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, concentrated suspensions, emulsions, natural and synthetic materials impregnated with the active compound, polymeric substances. It can be converted into conventional formulations such as very fine capsules. These formulations are prepared by incorporating, for example, the active compounds, optionally surfactants, by known methods.
i.e. emulsifiers and/or dispersants, and/or
or by mixing with fillers, ie liquid solvents and/or solid carriers, together with the use of blowing agents. If water is used as a bulking agent, organic solvents can also be used as auxiliary solvents. The following are mainly suitable as liquid solvents: aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated fats, such as chlorobenzene, chloroethylenes or methylene chloride. hydrocarbons such as cyclohexane or paraffins, aliphatic hydrocarbons such as mineral oil fractions, alcohols such as butanol or glycols and their ethers and esters such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone. Ketones, such as
Strongly polar solvents, such as dimethylformamide and dimethylsulfoxide, as well as water. The following are suitable as solid carriers: for example kaolin, clay, talc, thioyoke,
crushed natural minerals, such as quartz, attapulgite, montmorillonite or diatomaceous earth, and
Ground synthetic minerals, such as highly dispersed silicic acid, alumina and silicates; suitable solid carriers for granules are, for example, calcite, marble, pumice, sepiolite and dolomite. crushed and classified natural rocks such as, as well as synthetic granules of inorganic and organic flour, and sawdust,
Small particles of organic material such as coconut shells, corn cobs and tobacco stalks; suitable emulsifiers and/or foaming agents are: for example polyoxyethylene-fatty acid esters, polyoxyethylene-fatty alcohols ethers, such as alkylaryl polyglycol ethers,
Non-ionic and anionic emulsifiers such as alkyl sulfonates, alkyl sulfates, aryl sulfonates and albumin hydrolysis products; suitable dispersants include: for example lignin-
Sulfite waste liquor and methylcellulose. Carboxymethyl cellulose and powdered granules or latex, e.g. gum arabic,
Adhesives such as natural and synthetic polymers such as polyvinyl alcohol and polyvinyl acetate can be used in the formulation. Colorants such as inorganic pigments, such as iron oxide, titanium oxide and Prussian blue, and organic dyes, such as alizarin dyes, azo dyes and metal phthalocyanine dyes, and, for example, iron,
It is also possible to use micronutrients such as manganese, boron, copper, cobalt, molybdenum and zinc salts. The formulation generally contains 0.1-95% by weight, preferably 0.5
Contains ~90% by weight of active compound. The active compounds according to the invention can be used for combating weeds as such or in the form of formulations, as well as in finished formulations or as mixtures with known herbicides which can be tank mixed. . Mixtures with other known active compounds, such as, for example, fungicides, insecticides, acaricides, nematocides, bird control agents, growth regulators, plant nutrients and soil structure improving agents, are also used. can do. The active compounds can be used as such, in the form of their formulations or prepared from them by further dilution, for example in ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. It can be used in the following usage forms. They are used in conventional manner, for example by irrigation, spraying, atomizing, dusting or dusting. The active compounds according to the invention can be applied either before or after germination of the plants. Preference is given to application before germination of the plants, ie by the pre-emergence method. It can also be mixed into the soil before sowing. The amount of active compound used can vary within wide limits. The amount used depends essentially on the nature of the desired effect. In general, the amounts used are from 0.1 to 10 Kg, preferably from 0.1 to 5 Kg of active compound per hectare. In some cases, the compounds according to the invention also exhibit growth-regulating effects at certain use concentrations. The following examples are intended to illustrate the invention. Manufacturing Example Example 1 8.4 g (0.05 mol) of 2-chloro-5-methyl-benzoxazole to 8.5 g (0.05 mol) of hydroxyacetic acid 2,4-dimethylpiperidide, 5.6 g
(0.05 mol) of potassium t-butyrate and 100
ml of t-butanol mixture at room temperature (20±
Add at 10℃). The mixture is stirred at room temperature for 3 hours, diluted with 200 ml of methylene chloride, washed with 2N hydrochloric acid and then with water, dried and filtered. Carefully remove the solvent from the solution under reduced pressure. As residue, 7.5 g of an oily product are obtained which has a refractive index n 21 D of 1.5375 and contains 5-methyl-benzoxazol-2-yl-oxyacetic acid 2,4-dimethyl-piperidide. Compound (1) shown in the table below can be produced in the same manner as in Example 1. In the table below, compounds with Example numbers 15 to 20 and 24 are reference compounds.
【表】【table】
【表】【table】
【表】【table】
【表】
実施例 Ａ
発芽前試験
溶剤：５重量部のアセトン
乳化剤：１重量部のアルキルアリールポリグリ
コールエーテル
活性化合物の適当な調製剤を製造するために、
１重量部の活性化合物を上記の量の溶剤と混合
し、上記の量の乳化剤を加えたのち、その濃厚液
を水により所望の濃度に希釈する。
試験植物の種子を標準土壌中にまき、24時間後
に、活性化合物の調製剤で潅水する。単位面積当
りの水の量は一定に保つことが好都合である。調
製剤中の活性化合物の濃度は重要なことではな
く、単位面積当りに使用する活性化合物の量のみ
が決定的である。３週間後に、植物の損害の程度
を、未処理の対照の生長と比較した損傷百分率と
して評価する。数値は次のことを表わす：
０％＝作用なし（未処理対照と同様）
100％＝完全な破滅
この試験において、たとえば、製造実施例１、
２、４、５および７から化合物は優れた作用を表
わす。Table Example A Pre-emergence test Solvent: 5 parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether To prepare suitable preparations of the active compounds,
After mixing 1 part by weight of active compound with the above amount of solvent and adding the above amount of emulsifier, the concentrate is diluted with water to the desired concentration. The seeds of the test plants are sown in standard soil and after 24 hours are watered with the preparation of the active compound. It is advantageous to keep the amount of water per unit area constant. The concentration of active compound in the preparation is not critical, only the amount of active compound used per unit area is decisive. After 3 weeks, the extent of plant damage is evaluated as percentage damage compared to untreated control growth. The numbers represent: 0% = no effect (same as untreated control) 100% = complete destruction In this test, for example, production example 1,
Compounds from 2, 4, 5 and 7 exhibit excellent activity.
【表】【table】
【表】
実施例 Ｂ
水田雑草に対する湛水下発芽前水面処理試験
（ポツト試験）
活性化合物の調製
担体：アセトン５重量部
乳化剤：ベンジルオキシポリグリコールエーテ
ル１重量部
活性化合物の調合剤は、１重量部の活性化合物
と上述した分量の担体及び乳化剤とを混し、乳化
剤として得られる。その調合剤の所定薬量を、水
で希釈して調製する。
試験方法
1/5000のアールのワグネルポツトに水田土壌を
充填し、２〜３葉期（草丈約10cm）の水稲苗（品
種：金南風）を１ポツト当り２本移植した。更
に、イヌビエ、ホタルイ、コナギ、キカシグサの
種子及びマツバイの小片及びミズガヤツリの塊茎
を接種し、湿潤状態に保つた。５日後３cmの湛水
状態にし、本発明の化合物を乳剤の形態にて所定
量を散水処理し、処理後１日２〜３cmの割合で２
日間漏水処理し、その後は約３cmの湛水状態を保
ち、薬剤処理４週間後に除草効果及び水稲に対す
る薬害を次の基準により０〜５の段階に類別評価
した。
効果の評価は無処理区に比較した場合、
５：無処理区に対する殺草率95％以上（枯死）
４： 〃 80％以上95％未満
３： 〃 50％以上80％未満
２： 〃 30％以上50％未満
１： 〃 10％以上30％未満
０： 〃 10％未満（効果な
し）
水稲に対する薬害の評価は無処理区に比較した
場合、
５：無処理区に対する薬害率90％以上
（致命的損傷）
４：無処理区に対する薬害率50％以上90％未満
３： 〃 30％以上50％未満
２： 〃 10％以上30％未満
１： 〃 ０越10％未満
０： 〃 ０％（薬害なし）
とした。
試験結果は第Ｂ表に示す。[Table] Example B Pre-emergence water surface treatment test under flooding on paddy field weeds (pot test) Preparation of active compound Carrier: 5 parts by weight of acetone Emulsifier: 1 part by weight of benzyloxypolyglycol ether The preparation of the active compound is 1 part by weight An emulsifier is obtained by mixing part of the active compound with the above-mentioned amounts of carrier and emulsifier. A predetermined dose of the preparation is prepared by diluting it with water. Test method: Wagner pots with a radius of 1/5000 were filled with paddy soil, and two paddy rice seedlings (variety: Kinnanfu) at the 2- to 3-leaf stage (plant height about 10 cm) were transplanted per pot. In addition, seeds of Japanese grasshopper, bulrush, Japanese grasshopper, and small pieces of Japanese grasshopper and tubers of Cyperus japonica were inoculated and kept moist. After 5 days, the water was flooded to a depth of 3 cm, and a predetermined amount of the compound of the present invention in the form of an emulsion was sprinkled on water.
Water leakage treatment was carried out for one day, and then a flooded state of approximately 3 cm was maintained, and after 4 weeks of chemical treatment, the herbicidal effect and chemical damage to paddy rice were graded on a scale of 0 to 5 according to the following criteria. Evaluation of effectiveness is as follows when compared to untreated area: 5: Weed killing rate 95% or more (death) compared to untreated area 4: 80% or more but less than 95% 3: 50% or more but less than 80% 2: 30% or more Less than 50% 1: 〃 10% or more and less than 30% 0: 〃 Less than 10% (no effect) Evaluation of chemical damage to paddy rice when compared to untreated area: 5: Phytotoxicity rate is 90% or more compared to untreated area
(Fatal damage) 4: Chemical damage rate relative to untreated area: 50% or more and less than 90% 3: 〃 30% or more and less than 50% 2: 〃 10% or more and less than 30% 1: 〃 More than 0 and less than 10% 0: 〃 0% (No drug damage). The test results are shown in Table B.
【表】
化合物No.３、６、９、10、11、12、13、14、
16、17、18、19、20、24、27、28および30も上記
試験により同様の優れた除草効果が得られた。[Table] Compound No. 3, 6, 9, 10, 11, 12, 13, 14,
Similar excellent herbicidal effects were obtained in the above tests with Nos. 16, 17, 18, 19, 20, 24, 27, 28 and 30.
Claims (1)
またはC3〜C5−アルキニルを表わし、且つR2は
C1〜C5−アルキル、C3〜C5−アルケニル、フエ
ニル−C1〜C2−アルキルまたはフエニルを表わ
し、 あるいは式中で R1およびR2の両基は、それらが結合している
窒素原子と共に、ピペリジルおよび１，２，３，
４−テトラヒドロキノリルなる系列からの、場合
によつてはメチルおよび／またはエチルによつて
置換してある基、あるいは下記の基： 【式】 の置換したベンゾアゾール−２−イル−オキシ酢
酸アミド。 ２ 特許請求の範囲第１項記載の、式 の５−メチル−ベンゾキサゾール−２−イル−オ
キシ酢酸アミド。 ３ 特許請求の範囲第１項記載の式 の５−メチル−ベンゾキサゾール−２−イル−オ
キシ酢酸２−エチル−ピペリジド。 ４ 特許請求の範囲第１項記載の式 の５−メチル−ベンゾキサゾール−２−イル−オ
キシ酢酸Ｎ−エチル−Ｎ−イソプロピル−アミ
ド。 ５ 特許請求の範囲第１項記載の式 の５−メチル−ベンゾキサゾール−２−イル−オ
キシ酢酸２，４，６−トリメチルピペリジド。 ６ 特許請求の範囲第１項記載の式 の５−メチル−ベンゾキサゾール−２−イル−オ
キシ酢酸１，２，３，４−テトラヒドロキノリ
ド。 ７ 式 式中で、 Ｘは酸素または硫黄を表わし、 Ｒはメチルを表わし、 R1はC1〜C5−アルキル、C3〜C5−アルケニル
またはC3〜C5−アルキニルを表わし、且つR2は
C1〜C5−アルキル、C3〜C5−アルケニル、フエ
ニル−C1〜C2−アルキルまたはフエニルを表わ
し、 あるいは式中で R1およびR2の両基は、それらが結合している
窒素原子と共に、ピペリジルおよび１，２，３，
４−テトラヒドロキノリルなる系列からの、場合
によつてはメチルおよび／またはエチルによつて
置換してある基、あるいは下記の基： 【式】 の置換したベンズアゾール−２−イル−オキシ酢
酸アミドを有効成分として含有することを特徴と
する除草剤。[Claims] 1 formula In the formula, X represents oxygen or sulfur, R represents methyl, R1 represents C1 - C5 -alkyl, C3 - C5 -alkenyl or C3 - C5 -alkynyl, and R2 teeth
represents C1 - C5 -alkyl, C3 - C5 -alkenyl, phenyl- C1 - C2 -alkyl or phenyl, or in the formula both R1 and R2 are Along with the nitrogen atom, piperidyl and 1,2,3,
A group from the series 4-tetrahydroquinolyl, optionally substituted by methyl and/or ethyl, or a substituted benzazol-2-yl-oxyacetamide of formula . 2 Formula described in claim 1 5-methyl-benzoxazol-2-yl-oxyacetic acid amide. 3 Formula described in claim 1 5-Methyl-benzoxazol-2-yl-oxyacetic acid 2-ethyl-piperidide. 4 Formula described in claim 1 5-Methyl-benzoxazol-2-yl-oxyacetic acid N-ethyl-N-isopropyl-amide. 5 Formula described in claim 1 5-Methyl-benzoxazol-2-yl-oxyacetic acid 2,4,6-trimethylpiperidide. 6 Formula described in claim 1 5-methyl-benzoxazol-2-yl-oxyacetic acid 1,2,3,4-tetrahydroquinolide. 7 formula In the formula, X represents oxygen or sulfur, R represents methyl, R1 represents C1 - C5 -alkyl, C3 - C5 -alkenyl or C3 - C5 -alkynyl, and R2 teeth
represents C1 - C5 -alkyl, C3 - C5 -alkenyl, phenyl- C1 - C2 -alkyl or phenyl, or in the formula both R1 and R2 are Along with the nitrogen atom, piperidyl and 1,2,3,
A group from the series 4-tetrahydroquinolyl, optionally substituted by methyl and/or ethyl, or a substituted benzazol-2-yl-oxyacetic acid amide of formula A herbicide characterized by containing as an active ingredient.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803038599 DE3038599A1 (en) | 1980-10-13 | 1980-10-13 | Substd.-benzazol-2-yl oxy:acetic acid amide derivs. - used as selective herbicides for cotton, soya, beet and cereal crops |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5795971A JPS5795971A (en) | 1982-06-15 |
| JPH0369906B2 true JPH0369906B2 (en) | 1991-11-05 |
Family
ID=6114250
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16211581A Granted JPS5795971A (en) | 1980-10-13 | 1981-10-13 | Compound, manufacture and use |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS5795971A (en) |
| DE (1) | DE3038599A1 (en) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0005501B1 (en) * | 1978-05-20 | 1981-11-25 | Bayer Ag | Heteroaryloxy-acetamides, process for their preparation and their use as herbicides |
| DE3038636A1 (en) * | 1980-10-13 | 1982-05-27 | Bayer Ag, 5090 Leverkusen | Herbicidal n,n-di:substd. 2-heterocyclyl:oxy-acetamide derivs. prodn. - by reaction of n,n-di:substd. 2-hydroxy- or 2-acyloxy-acetamide cpds. with heterocyclyl halide(s) |
| DE3038652A1 (en) * | 1980-10-13 | 1982-05-19 | Bayer Ag, 5090 Leverkusen | 5-Chloro-benzoxazol-2-yl oxy:acetic acid amide derivs. - used as selective herbicides for cotton, soya, beet and cereal crops |
| DE3418168A1 (en) * | 1984-05-16 | 1985-11-21 | Bayer Ag, 5090 Leverkusen | 6-CHLORBENZAZOLYLOXYACETAMIDE |
| DE3529950A1 (en) * | 1985-08-22 | 1987-03-05 | Licentia Gmbh | Method and sensor for measuring the oxygen content in exhaust gases |
| DE4133673A1 (en) * | 1991-10-11 | 1993-04-15 | Bayer Ag | NEW 2- (2-BENZOXAZOLYL-OXY) -ACETAMIDES |
| DE19704370A1 (en) * | 1997-02-06 | 1998-08-13 | Bayer Ag | Substituted benzoxazolyloxyacetanilides |
| US8916550B2 (en) | 2005-05-09 | 2014-12-23 | Hydra Biosciences, Inc. | Compounds for modulating TRPV3 function |
| CN101233132A (en) | 2005-05-09 | 2008-07-30 | 海德拉生物科学公司 | Compounds for modulating TRPV3 function |
| WO2008033564A1 (en) | 2006-09-15 | 2008-03-20 | Hydra Biosciences Inc. | Compounds for modulating trpv3 function |
| JP2020138882A (en) * | 2019-02-28 | 2020-09-03 | 株式会社グリーンドゥ | Surface protective and decorative construction method for cement-based structure |
| JP2023512664A (en) | 2020-01-29 | 2023-03-28 | カマリ ファーマ リミテッド | Compounds and compositions for use in treating skin disorders |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS54154762A (en) * | 1978-05-20 | 1979-12-06 | Bayer Ag | Substituted carboxylic acid amide*its manufacture and use as herbicide |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2065552A1 (en) * | 1970-06-20 | 1974-03-07 | Bayer Ag | OXAZOLYL VINEGAR ACID DERIVATIVES |
| JPS4961334A (en) * | 1972-10-11 | 1974-06-14 | ||
| DE2903966A1 (en) * | 1979-02-02 | 1980-08-07 | Bayer Ag | 2-Carbamoyl:methoxy-benzoxazole and benzothiazole derivs. - useful as herbicides, fungicides and plant growth regulators |
| DE2822155A1 (en) * | 1978-05-20 | 1979-11-22 | Bayer Ag | SUBSTITUTED CARBON ACID AMIDES, METHODS FOR THEIR PRODUCTION AND USE AS HERBICIDES |
| DE2914003A1 (en) * | 1979-04-06 | 1980-10-16 | Bayer Ag | Selective herbicide azolyl:oxy-acetamide derivs. - prepd. by reaction of a hydroxy-acetamide cpd. with a halo-substd. azole e.g. thiazole |
| DE3004326A1 (en) * | 1980-02-06 | 1981-08-13 | Bayer Ag, 5090 Leverkusen | Azolyl:oxy-carboxamide derivs. - used as plant growth regulators, defoliants, desiccants, germination inhibitors and esp. selective herbicides (PT 16.9.80) |
| DE2946432A1 (en) * | 1979-11-17 | 1981-06-11 | Bayer Ag, 5090 Leverkusen | TETRAZOLYLOXYCARBONIC ACID AMIDES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS HERBICIDES |
| DE2946524A1 (en) * | 1979-11-17 | 1981-06-11 | Bayer Ag, 5090 Leverkusen | AZOLYLOXY-CARBONIC ACID-N-OXY-AMIDES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS HERBICIDES |
| DE3018075A1 (en) * | 1980-05-10 | 1981-11-12 | Bayer Ag, 5090 Leverkusen | AGENTS FOR REGULATING PLANT GROWTH, THEIR PRODUCTION AND THEIR USE |
| DE3038636A1 (en) * | 1980-10-13 | 1982-05-27 | Bayer Ag, 5090 Leverkusen | Herbicidal n,n-di:substd. 2-heterocyclyl:oxy-acetamide derivs. prodn. - by reaction of n,n-di:substd. 2-hydroxy- or 2-acyloxy-acetamide cpds. with heterocyclyl halide(s) |
| DE3038652A1 (en) * | 1980-10-13 | 1982-05-19 | Bayer Ag, 5090 Leverkusen | 5-Chloro-benzoxazol-2-yl oxy:acetic acid amide derivs. - used as selective herbicides for cotton, soya, beet and cereal crops |
-
1980
- 1980-10-13 DE DE19803038599 patent/DE3038599A1/en not_active Withdrawn
-
1981
- 1981-10-13 JP JP16211581A patent/JPS5795971A/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS54154762A (en) * | 1978-05-20 | 1979-12-06 | Bayer Ag | Substituted carboxylic acid amide*its manufacture and use as herbicide |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5795971A (en) | 1982-06-15 |
| DE3038599A1 (en) | 1982-05-19 |
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