JPH0217187A - Phenoxypropionamide derivative and herbicide - Google Patents
Phenoxypropionamide derivative and herbicideInfo
- Publication number
- JPH0217187A JPH0217187A JP16690088A JP16690088A JPH0217187A JP H0217187 A JPH0217187 A JP H0217187A JP 16690088 A JP16690088 A JP 16690088A JP 16690088 A JP16690088 A JP 16690088A JP H0217187 A JPH0217187 A JP H0217187A
- Authority
- JP
- Japan
- Prior art keywords
- ring
- substituted
- atom
- formula
- lower alkyl
- 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 16
- 239000004009 herbicide Substances 0.000 title claims abstract description 13
- ANCDHBXLDURTHN-UHFFFAOYSA-N 2-phenoxypropanamide Chemical class NC(=O)C(C)OC1=CC=CC=C1 ANCDHBXLDURTHN-UHFFFAOYSA-N 0.000 title claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 9
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- 150000003839 salts Chemical class 0.000 claims abstract description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 4
- 125000005843 halogen group Chemical group 0.000 claims description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 4
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 abstract description 32
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract description 12
- 241000196324 Embryophyta Species 0.000 abstract description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract description 9
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 abstract description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 abstract description 3
- 238000002360 preparation method Methods 0.000 abstract description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 150000002367 halogens Chemical class 0.000 abstract 3
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 abstract 1
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 229940080818 propionamide Drugs 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 238000000862 absorption spectrum Methods 0.000 description 12
- 238000010586 diagram Methods 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- -1 alkali metal bicarbonates Chemical class 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- 244000025254 Cannabis sativa Species 0.000 description 9
- 241000192043 Echinochloa Species 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 241000209094 Oryza Species 0.000 description 6
- 235000007164 Oryza sativa Nutrition 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 235000009566 rice Nutrition 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 240000001592 Amaranthus caudatus Species 0.000 description 5
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 5
- 241000209140 Triticum Species 0.000 description 5
- 235000021307 Triticum Nutrition 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 235000011181 potassium carbonates Nutrition 0.000 description 5
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 4
- 241001621841 Alopecurus myosuroides Species 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 240000002439 Sorghum halepense Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 235000017788 Cydonia oblonga Nutrition 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- 241000209504 Poaceae Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229940126208 compound 22 Drugs 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
- 150000002170 ethers Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000000887 hydrating effect Effects 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000003444 phase transfer catalyst Substances 0.000 description 2
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 2
- 235000015497 potassium bicarbonate Nutrition 0.000 description 2
- 239000011736 potassium bicarbonate Substances 0.000 description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 1
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
- XLHUBROMZOAQMV-UHFFFAOYSA-N 1,4-benzosemiquinone Chemical group [O]C1=CC=C(O)C=C1 XLHUBROMZOAQMV-UHFFFAOYSA-N 0.000 description 1
- SXERGJJQSKIUIC-UHFFFAOYSA-N 2-Phenoxypropionic acid Chemical compound OC(=O)C(C)OC1=CC=CC=C1 SXERGJJQSKIUIC-UHFFFAOYSA-N 0.000 description 1
- YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 241000254032 Acrididae Species 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- HGAYUADKIJRKLI-UHFFFAOYSA-K C([O-])(O)=O.[Au+3].C([O-])(O)=O.C([O-])(O)=O Chemical class C([O-])(O)=O.[Au+3].C([O-])(O)=O.C([O-])(O)=O HGAYUADKIJRKLI-UHFFFAOYSA-K 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 241000497005 Ixophorus unisetus Species 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 101000650578 Salmonella phage P22 Regulatory protein C3 Proteins 0.000 description 1
- 244000062793 Sorghum vulgare Species 0.000 description 1
- 101001040920 Triticum aestivum Alpha-amylase inhibitor 0.28 Proteins 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 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
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium 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
- 235000011116 calcium hydroxide Nutrition 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000004202 carbamide 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
- 229910052570 clay Inorganic materials 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229940125797 compound 12 Drugs 0.000 description 1
- 229940125758 compound 15 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000002262 irrigation Effects 0.000 description 1
- 238000003973 irrigation Methods 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
Abstract
Description
【発明の詳細な説明】
産業上の利用分野
本発明は、新規なフェノキシプロピオン酸アミド誘導体
及びこれを有効成分として含有する除草剤に関するもの
である。DETAILED DESCRIPTION OF THE INVENTION Field of Industrial Application The present invention relates to a novel phenoxypropionic acid amide derivative and a herbicide containing the same as an active ingredient.
従来の技術
従来、ある種のフェノキシプロピオン酸アミド誘導体が
除草活性を有することは知られている（特Ｈ昭５３−
ＩＧ７６７％公＄１１、特Ｈ昭５４−１１２０８号公報
）。2. Prior Art It has been known that certain phenoxypropionic acid amide derivatives have herbicidal activity (Patent H.
IG767% public $11, special publication number H 54-11208).
しかしながら、これらの化合物は、ヒエ、エノコログサ
、ジ１ンソングラス等の禾本科雑草に対する除草効果及
びイネ、コムギ等の有用作物に対する安全性については
必ずしも高くないため、実用上問題がある。However, these compounds do not necessarily have a high herbicidal effect on weeds of the grass family such as barnyard grass, foxtail grass, and quince grass, and are not necessarily safe for useful crops such as rice and wheat, which poses practical problems.
発明が解決しようとする課題
本発明は、このような従来のフェノキシプロピオン酸ア
ミド誘導体の問題点を克服し、禾本科雑草に対する優れ
た除草効果と有用作物に対する安全性が共に高い新規な
フェノキシプロピオン酸アミド誘導体を提供することを
目的としてなされたものである。Problems to be Solved by the Invention The present invention overcomes the problems of conventional phenoxypropionic acid amide derivatives and provides a novel phenoxypropionic acid that has both an excellent herbicidal effect on weeds of the family Weeds and a high degree of safety for useful crops. This was done for the purpose of providing amide derivatives.
課題を解決するだめの手段
本発明者らは、このような改良されたフェノキシプロピ
オン酸アミド系化合物の開発を目的に、鋭意研究しｔ；
結果、本発明化合物が、ヒエ、メヒシバ、エノコログサ
、ジ１ンソングラス等の禾本科雑草に対して優れた除草
効果を示すと共に、有用作物、特にコムギ、イネに対す
る安全性が高いことを見出し、本発明を完成するに至っ
た。Means for Solving the Problems The present inventors have conducted extensive research with the aim of developing such improved phenoxypropionic acid amide compounds.
As a result, it was discovered that the compound of the present invention exhibits an excellent herbicidal effect against grasshopper weeds such as barnyard grass, jack grass, foxtail grass, and quince grass, and is highly safe for useful crops, particularly wheat and rice, and the present invention I was able to complete it.
すなわち、本発明は下記一般式（Ｉ）
に例示する。化合物番号は以後の記載において、参照さ
れる。That is, the present invention is exemplified by the following general formula (I). Compound numbers are referred to in the following description.
［式中、Ｒは水素原子又はハロゲン原子を示し、Ｘは酸
素原子又は硫黄原子を示し、Ｙは窒素原子を１ないし３
個含み、硫黄原子を１個含んでいてもよい、５ないし６
員へテロ環（線環は１ないし２個の酸素原子、ハロゲン
息子、低級アルキル基、低級アルコキシ基又は低級アル
キルアミノ基で置換されていてもよい）を示す】
で表わされるフェノキシプロピオン酸アミド誘導体及び
その塩に関するものである。[In the formula, R represents a hydrogen atom or a halogen atom, X represents an oxygen atom or a sulfur atom, and Y represents 1 to 3 nitrogen atoms.
may contain 1 sulfur atom, 5 to 6
A phenoxypropionic acid amide derivative represented by a membered heterocycle (the linear ring may be substituted with 1 or 2 oxygen atoms, a halogen atom, a lower alkyl group, a lower alkoxy group, or a lower alkylamino group) and its salts.
上記一般式で表わされる本発明化合物を第１表また、第
１表中、測定不可の化合物についてはそれぞれ赤外吸収
スペクトル図を第１図ないし第１０図に示す。The compounds of the present invention represented by the above general formula are shown in Table 1, and infrared absorption spectra of compounds in Table 1 that cannot be measured are shown in Figs. 1 to 10, respectively.
本発明化合物は反応式（１）、反応式（２）で示す方法
によって製造できる。しかし、これらの方法に限定され
るものでない。The compound of the present invention can be produced by the method shown in Reaction Formula (1) and Reaction Formula (2). However, the method is not limited to these methods.
反応式（１）
（式中、Ｚはハロゲン原子、アルキルスルホニル基又は
ベンゼンスルホニル基を示し、Ｒ，Ｘ及びＹは前記と同
じ意味を表わす）
反応式（Ｌ）で示されるように、−数式（ＩＩ）で表わ
される化合物と一数式ＣＩＩＩ）で表わされる化合物と
を塩基の存在下反応させることにより、一般式（Ｉ）で
表わされる本発明化合物を製造することができる。Reaction formula (1) (In the formula, Z represents a halogen atom, an alkylsulfonyl group, or a benzenesulfonyl group, and R, X and Y have the same meanings as above.) As shown in the reaction formula (L), - formula The compound of the present invention represented by general formula (I) can be produced by reacting the compound represented by (II) with the compound represented by formula CIII) in the presence of a base.
この塩基としては、例えば水酸化ナトリウム、水酸化カ
リウム等のアルカリ金属水酸化物類、炭酸ナトリウム、
炭酸カリウム等のアルカリ金属炭酸塩類、炭酸水素ナト
リウム、炭酸水素カリウム等のアルカリ金属重炭酸塩類
などの無機塩基類又はトリエチルアミン、Ｎ、Ｎ−ジメ
チルアニリン、ピリジン、Ｉ、８−ジアザビシクロ［５
，４，Ｏ３ウンデ−７−セン等の有機塩基類が挙げられ
る。Examples of the base include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, sodium carbonate,
Inorganic bases such as alkali metal carbonates such as potassium carbonate, alkali metal bicarbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate, or triethylamine, N,N-dimethylaniline, pyridine, I,8-diazabicyclo[5
, 4, O3 unde-7-cene and the like.
また、必要に応じて、テトラ−ｎ−ブチルアンモニウム
ブロマイド、１トクラウンー６ （１，４，７，１０，
１３１６−へキサオキサシクロオクタデカン）等の相関
移動触媒を添加することにより、目的とする反応を速や
かに行うこともできる。In addition, if necessary, tetra-n-butylammonium bromide, 1 Tocro-6 (1,4,7,10,
By adding a phase transfer catalyst such as 1316-hexaoxacyclooctadecane), the desired reaction can be carried out quickly.
反応は必要ならば適当な１種又は２種以上の希釈剤の存
在下で行うことができる。この希釈剤としては不活性な
有機溶媒であり、例えばアセトン、ブタノン等のケトン
類、ベンゼン、トノレニン、キシレン、クロルベンゼン
等の芳香族炭化水素類、石油エーテル、リグロイン等の
脂肪族炭化水素類、ジエチルエーテル、テトラヒドロ７
ラン、ジオキサン等のエーテル類、アセトニトリＪｕ、
プロピオニトリル等のニトリル類又はＮ、Ｎ−ジメチル
ホルムアミド、Ｎ、トジメチルアセトアミド、トメチル
ピロリドン等のアミド類等が挙げられる。The reaction can be carried out in the presence of one or more suitable diluents, if necessary. The diluent is an inert organic solvent, such as ketones such as acetone and butanone, aromatic hydrocarbons such as benzene, tonolenine, xylene, and chlorobenzene, aliphatic hydrocarbons such as petroleum ether and ligroin, diethyl ether, tetrahydro 7
Ran, ethers such as dioxane, acetonitrile Ju,
Examples include nitriles such as propionitrile, and amides such as N,N-dimethylformamide, N,todimethylacetamide, and tomethylpyrrolidone.
反応温度は通常０℃から反応系における還流温度までの
任意のものであり、好ましくは５０℃〜１００℃である
０反応時間は化合物により異なるが、通常１〜６時間反
応させれば収率良く目的物を得ることができる。The reaction temperature is usually any value from 0°C to the reflux temperature of the reaction system, preferably from 50°C to 100°C.The reaction time varies depending on the compound, but usually a reaction time of 1 to 6 hours will give a good yield. You can get what you want.
反応式（２）
（式中、Ｒ，Ｘ、Ｙ及びＺは前記と同じ意味を表わす）
反応式（２）で示されるように、一般式（ＩＶ）で表わ
される化合物と一般式（Ｖ）で表わされる化合物とを塩
基の存在下反応させることによっても、一般式（Ｉ）で
表わされる本発明化合物を製造することができる。Reaction formula (2) (wherein, R, X, Y and Z have the same meanings as above) As shown in reaction formula (2), a compound represented by general formula (IV) and general formula (V) The compound of the present invention represented by general formula (I) can also be produced by reacting the compound represented by formula (I) with the compound represented by formula (I) in the presence of a base.
この塩基としては、例えば水酸化ナトリウム、水酸化カ
リウム等のアルカリ金属水酸化物類、炭酸ナトリウム、
炭酸カリウム等のアルカリ金属炭酸塩類、炭酸水素ナト
リウム、炭酸水素カリウム等のアルカリ金ｉ重炭酸塩類
などの無機塩基類又はトリエチルアミン、Ｈ，トリエチ
ルアミン、ピリジン、１．トジアザビシクロ［５，ＬＯ
Ｉ ウンデ−７−セン等の有機塩基類が挙げられる。Examples of the base include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, sodium carbonate,
Alkali metal carbonates such as potassium carbonate, inorganic bases such as alkali gold bicarbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate, or triethylamine, H, triethylamine, pyridine, 1. Tojiazabicyclo[5,LO
Examples include organic bases such as I unde-7-cene.
また必要に応じて、テトラ−ｎ−ブチルアンモニウムブ
ロマイド、１トクラウンー６ （＋、４，７．１０．１
３．１６−へキサオキサンクロオクタデカン）等の相関
移動触媒を添加することにより、目的とする反応を速や
かに行うこともできる。In addition, if necessary, tetra-n-butylammonium bromide, 1 Tocro-6 (+, 4, 7.10.1
By adding a phase transfer catalyst such as 3.16-hexaoxanechlorooctadecane), the desired reaction can be carried out quickly.
反応は必要ならば適当な１種又は２種以上の希釈剤の存
在下で行うことができる。この希釈剤としては不活性な
有機溶媒であり、例えばアセトン、ブタノン等のケトン
類、ベンゼン、トルエン、キシレン、クロルベンゼン等
の芳香族炭化水素類、石油エーテル、リグロイン等の脂
肪族炭化水素類、ジエチルエーテル、テトラヒドロフラ
ン、ジオキサン等のエーテル類、アセトニトリル、プロ
ピオニトリル等のニトリル類又はＮ、Ｎ−ジメチルホル
ムアミド、Ｎ、Ｎ−ジメチルアセトアミド、トメチルピ
ロリドン等のアミド類等が挙げられる。The reaction can be carried out in the presence of one or more suitable diluents, if necessary. The diluent is an inert organic solvent, such as ketones such as acetone and butanone, aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene, aliphatic hydrocarbons such as petroleum ether and ligroin, Examples include ethers such as diethyl ether, tetrahydrofuran and dioxane, nitriles such as acetonitrile and propionitrile, and amides such as N,N-dimethylformamide, N,N-dimethylacetamide and tomethylpyrrolidone.
反応温度は通常０℃から反応系における還流温度までの
任意のものであり、５０°Ｃ〜ＩＨ℃が好ましい。反応
時間は化合物により異なるが、通常１〜６時間反応させ
れば収率良く目的物を得ることができる。The reaction temperature is generally any value from 0°C to the reflux temperature in the reaction system, preferably 50°C to IH°C. Although the reaction time varies depending on the compound, the desired product can be obtained in good yield if the reaction is generally carried out for 1 to 6 hours.
実施例
次に実施例によって本発明をさらに詳細に説明するが、
本発明はその要旨を超えない限り、以下の実施例に限定
されるものではない。EXAMPLES Next, the present invention will be explained in more detail by examples.
The present invention is not limited to the following examples unless it exceeds the gist thereof.
実施例１
Ｎ−（Ｌ５−ジメチル−３−ピラゾリル） −２−［＋
−（６−タロロペンゾオキサゾリルー２−オキシ）フェ
ノキシ】プロピオン酸アミド（化合物番号＋９）の製造
（−（６−クロロペンゾオキサゾリルー２−オキシ）フ
ェノール１．Ｓｙ （５，７ミリモル） 、 Ｎ−（Ｌ
５−ジメチルートビラゾリル）−トブロモプロビオン酸
アミド１．４９（５，７ミリモル）及びアセトニトリル
ｌｏｏｍｌからなる溶液に炭酸カリウム０．９９（６，
５ミリモル）と触媒量のテトラ−ｎ−ブチルアンモニウ
ムブロマイドを加え、加熱還流下３時間撹拌した。Example 1 N-(L5-dimethyl-3-pyrazolyl)-2-[+
-(6-thalolopenzoxazolyl-2-oxy)phenoxy] Production of propionic acid amide (compound number +9) (-(6-chloropenzoxazolyl-2-oxy)phenol 1.Sy (5,7 mmol), N-(L
To a solution consisting of 1.49 (5.7 mmol) of 5-dimethyltovirazolyl)-tobromoprobionic acid amide and 1 ml of acetonitrile was added 0.99 (6,0 ml) of potassium carbonate.
5 mmol) and a catalytic amount of tetra-n-butylammonium bromide were added, and the mixture was stirred under heating under reflux for 3 hours.
反応終了後、室温まで冷却し、固体をろ別したのち、減
圧下で溶媒を留去し、次いで得られた残渣をカラムクロ
マトグラフィーにより精製して目的物２．０ｇ（収率８
３％、融点■１〜ｌ ４５ ’Ｃ）を？！４ｆ：。After the reaction was completed, it was cooled to room temperature, the solid was filtered off, the solvent was distilled off under reduced pressure, and the resulting residue was purified by column chromatography to obtain 2.0 g of the target product (yield: 8
3%, melting point ■1~l45'C)? ! 4f:.
実施例２
Ｎ−（１，６−シメチルートピリジル） −２−（４−
（６−タロロペンゾオキサゾリルー２−オキシ）フェノ
キシ］プロピオン酸アミド（化合物番号６）の製造２．
６−ジクロロベンゾオキサゾール１．１９（５，９ミリ
モル） 、Ｎ−（４ｊ−ジメチル−トビリジル）−ト（
４−ヒドロキシフェノキシ）プロピオン酸アミド１．フ
タ（ｓ、１ミリモル）及びアセトニトリルｌＯ１１１０
１ｌからなる溶液に炭酸カリウム１．０９ （７，２ミ
リモル）と触媒量のテトラ−ｎ−ブチルアンモニウムブ
ロマイドを加え、加熱還流下３時間撹拌した。Example 2 N-(1,6-dimethyltopyridyl)-2-(4-
Preparation of (6-talolopenzoxazolyl-2-oxy)phenoxy]propionic acid amide (Compound No. 6)2.
6-dichlorobenzoxazole 1.19 (5.9 mmol), N-(4j-dimethyl-tobiridyl)-t(
4-Hydroxyphenoxy)propionic acid amide 1. Lid (s, 1 mmol) and acetonitrile lO1110
1.09 (7.2 mmol) of potassium carbonate and a catalytic amount of tetra-n-butylammonium bromide were added to a solution consisting of 1 liter, and the mixture was stirred under heating under reflux for 3 hours.
反応終了後、実施例１と同様な方法により処理して目的
物１３９ （収率８８％、融点９３〜９４℃）を得を二
。After the reaction was completed, the desired product 139 (yield 88%, melting point 93-94°C) was obtained by processing in the same manner as in Example 1.
実施例３
ト（≦−クロロートビリジル’） −２−［４−（６−
クロロペンゾチアゾリルー２−オキシ）フェノキシＪプ
ロピオン酸アミド（化合物番号２５）の製造２．６−ジ
クロロベンゾチアゾールｌ−５ｙ（７，４ミリモル）、
Ｎ−（Ｓ−クロロ−２−ピリジル）−２−（４−ヒドロ
キシフェノキシ）プロピオン酸アミド１２９（７，５ミ
リモル）及びＮ、１１−ジメチルホルムアミド１００ｍ
１からなる溶液に炭酸カリウム１．２ｙ（１，７ミリモ
ル）を加え、１００℃で３時間撹拌した。Example 3 To(≦-chloroviridyl') -2-[4-(6-
Preparation of chloropenzothiazolyl-2-oxy)phenoxy J propionic acid amide (compound no. 25) 2.6-dichlorobenzothiazole l-5y (7.4 mmol),
N-(S-chloro-2-pyridyl)-2-(4-hydroxyphenoxy)propionic acid amide 129 (7.5 mmol) and N,11-dimethylformamide 100 m
1.2y (1.7 mmol) of potassium carbonate was added to the solution consisting of 1, and the mixture was stirred at 100°C for 3 hours.
反応終了後、実施例１と同様な方法により処理して目的
物３．０９ （収率８８％、融点１１１〜１１５°Ｃ）
を得た。After the reaction was completed, the desired product 3.09 (yield 88%, melting point 111-115°C) was obtained by processing in the same manner as in Example 1.
I got it.
本発明の除草剤は、本発明化合物であるフェノキシプロ
ピオン酸アミド誘導体を有効成分として含をする。The herbicide of the present invention contains the compound of the present invention, a phenoxypropionic acid amide derivative, as an active ingredient.
本発明化合物を除草剤として使用する場合、化合物のみ
、又はこれに農薬の製剤化に際し一般的に用いられる、
担体、界面活性剤、分散剤、補助剤等を配合して、水和
剤、粒剤、乳剤又は粉剤等の各種形態に製剤化して使用
することができる。When the compound of the present invention is used as a herbicide, the compound alone or the compound commonly used in the formulation of agricultural chemicals,
It can be formulated into various forms such as wettable powders, granules, emulsions, or powders by adding carriers, surfactants, dispersants, adjuvants, etc., and used.
製剤化に際して用いられる担体としては、例えば、ジ−
クライト、タルク、ベントナイト、クレーカオリン、ケ
イソウ土、ホワイトカーボン、バーミキュライト、消石
灰、珪砂、硫安、尿素等の固体担体、イングロビルアル
コール、キシレン、シクロヘキサン、メチルナフタレン
等の液体担体Ｗが挙げられる。界面活性剤及び分散剤と
しては、例えばアルコール硫酸エステル塩、アルキルア
リールスルホン酸塩、リグニンスルホン酸塩、ポリオキ
シエチレングリコールエーテル、ポリオキシエチレンア
ルキルアリールエーテル、ポリオキシエチレンンルビタ
ンモノアルキレート等カ挙ケラれる。補助剤としては、
例えば、カルボキシメチルセルロース、ポリエチレング
リコール、アラビアゴム等が挙げられる。使用に際して
は、適当な濃度に希釈して散布するか又は直接施用する
。Examples of carriers used in formulation include di-
Examples include solid carriers such as clite, talc, bentonite, clay kaolin, diatomaceous earth, white carbon, vermiculite, slaked lime, silica sand, ammonium sulfate, and urea, and liquid carriers W such as inglobil alcohol, xylene, cyclohexane, and methylnaphthalene. Examples of surfactants and dispersants include alcohol sulfate salts, alkylaryl sulfonates, lignin sulfonates, polyoxyethylene glycol ethers, polyoxyethylene alkylaryl ethers, and polyoxyethylene rubitan monoalkylates. I get vignetted. As an adjuvant,
Examples include carboxymethylcellulose, polyethylene glycol, gum arabic, and the like. When using it, either dilute it to an appropriate concentration and spray it, or apply it directly.
まｊ；、本発明の除草剤は他の除草剤と混合して使用す
ることもできる。Also, the herbicide of the present invention can be used in combination with other herbicides.
次に、本発明除草剤の実施例を挙げるが、本発明はこの
範囲に限定されるものではない。Next, Examples of the herbicide of the present invention will be given, but the present invention is not limited to this range.
なお、実施例中に記載の％は重量百分率を示す。In addition, % described in an example shows a weight percentage.
実施例４（水和剤）
化合物（４）１０％、エマルゲン８１０（花王株式会社
登録商標） Ｏ，Ｓ％、デモールＮ（花王株式会社登録
商標） Ｇ、Ｓ％、クニライト（クニミ不工業株式会社
登録商標）’！０１２０％、ジ−クライト（ジ−クライ
ト株式会社登録商標）ＣＡ６９％を均一に混合粉砕して
水和剤とした。Example 4 (hydrating powder) Compound (4) 10%, Emulgen 810 (registered trademark of Kao Corporation) O, S%, Demol N (registered trademark of Kao Corporation) G, S%, Kunilite (Kunimi Fu Kogyo Co., Ltd.) Registered trademark)'! 0120% and Zikrite (Zikrite Co., Ltd. registered trademark) CA69% were uniformly mixed and ground to prepare a wettable powder.
実施例５（乳剤）
化合物（４）３０％、シクロへキサノン２０％、ポリオ
キシエチレンアルキルアリールエーテル１１％、アルキ
ルベンゼンスルホン酸カルシウム４％、及びメチルナフ
タリン３５％を均一に溶解して乳剤としに。Example 5 (Emulsion) An emulsion was prepared by uniformly dissolving 30% of compound (4), 20% of cyclohexanone, 11% of polyoxyethylene alkylaryl ether, 4% of calcium alkylbenzene sulfonate, and 35% of methylnaphthalene.
実施例６（粒剤）
化合物（４）５％、ラウリルアルコ−ルミミニステルの
ナトリウム塩２％、リグニンスルホン酸ナトリウム５％
、カルボキンメチルセルロース２％、及びクレー８６％
を均一に混合粉砕する。この混合物＋００Ｉ！量部に水
２０１１１部を加えて練合し、押出式造粒機を用いて１
４〜３２メツシユの粒状に加工しｔ；のち、乾燥して粒
剤とした。Example 6 (granules) Compound (4) 5%, sodium salt of lauryl alcohol miminister 2%, sodium lignin sulfonate 5%
, carboquine methylcellulose 2%, and clay 86%
Mix and grind evenly. This mixture +00I! Add 20,111 parts of water to the volume, mix, and use an extrusion granulator to make 1
The mixture was processed into 4 to 32 mesh granules and then dried to form granules.
実施例７（粉剤）
化合物（４）２％、ケイソウ土５％、及びクレー９３％
を均一に混合粉砕して粉剤とした。Example 7 (powder) Compound (4) 2%, diatomaceous earth 5%, and clay 93%
The mixture was uniformly mixed and pulverized to form a powder.
本発明の除草剤は、畑地において、１１革の発芽前又は
発芽後に土壌旭理又は茎葉旭理することにより、畑地に
発生する多くの雑草を防除することができる。また、水
田において、雑草の発芽前又は発芽後に湛水土壌処理又
は：ｒ、ｌＩｌ：ｓ理することにより水ＥＢ１．：発生
する多くの雑草を防除することができる。The herbicide of the present invention can control many weeds that occur in upland fields by soil-filtering or foliage-filtering before or after the germination of 11 seeds. In addition, in paddy fields, water EB1. : Many weeds that occur can be controlled.
本発明の除１［剤は、有効成分でｌＯアール当りａ、ｌ
ｙ〜１＆９、好ましくは１９〜４００９施用する。また
植物茎葉に散布する場合は１ ｐｐｍ−１１００００ｐ
ｐに希釈して施用する。The agent of the present invention is an active ingredient with a, l per lO are.
Apply y~1&9, preferably 19-4009. Also, when spraying on plant stems and leaves, 1 ppm-110000p
Apply diluted to p.
発明の効果
本発明の化合物及び除草剤は、畑地に発生するヒエ、メ
ヒシバ、オヒシバ、ブラックグラス、エノコログサ類、
ジョンソングラス等の禾本科ｉ草を有効に防除すること
ができる。Effects of the Invention The compounds and herbicides of the present invention can be used to control barnyard grass, black grass, blackgrass, black grass, foxtail grass, etc. that occur in fields.
It is possible to effectively control grasses belonging to the family Hematinaceae, such as johnson grass.
また、水田に発生するヒエ類も有効に防除することがで
きる。一方、作物、中でもコムギ、イネに対する安全性
が高い。In addition, barnyard grasses that occur in rice fields can also be effectively controlled. On the other hand, it is highly safe for crops, especially wheat and rice.
次に、本発明除草剤の奏する効果を試験例を挙げて説明
する。Next, the effects of the herbicide of the present invention will be explained using test examples.
なお、以下の試験に８いて表中の略記号は下記の植物を
表わす。In the following tests, the abbreviations in the table represent the following plants.
Ｅｃ；ヒエ、Ｄｉ：メヒシバ、Ｓｅ；エノコログサ、Ｓ
自；ジョンソングラス、Ｏｒ；イネ、Ｔ「；コムギまた
、比較薬剤は特開昭５３−４０７６１号公報記載の下記
化合物を示す
試験例１
土壌を充填した６００Ｃ１１”ポットにヒエ、メヒシバ
、エノコログサ、ジョンソングラス、イネ及びコムギの
各種子を播種し、Ｏ，Ｓ〜１ｃ＋＋＋に覆土した。ポッ
トは２０〜２５℃のガラス室内で２週間育成後、実施例
４に準じて調製した水和剤の所定量を、ｌ＃アール当り
ｌ・口の水で希釈し、茎葉表面に散布した。ｖ４査は薬
剤処理後１４日０に第２表の基準に従い行った。結果を
第３表に指数で示した。Ec; Japanese barnyard grass, Di: Japanese barnyard grass, Se; Japanese foxtail grass, S
Auto: Johnson grass, Or: Rice, T: Wheat Also, the comparative drugs are the following compounds described in JP-A No. 53-40761 Test Example 1 Barnyard grass, Mexican grass, foxtail grass, and Johnson grass were placed in a 600C11" pot filled with soil. Seeds of grass, rice, and wheat were sown and covered with soil in O, S to 1c+++. After the pots were grown in a glass room at 20 to 25° C. for two weeks, a predetermined amount of a hydrating powder prepared according to Example 4 was diluted with 1 mouth water per 1 #are and sprayed on the foliage surface. The v4 test was conducted 14 days after drug treatment according to the criteria in Table 2. The results are shown in Table 3 as an index.
第
丁く
試験例２（水田雑草防除効果）
１００ｃｍ”ポットに水田土壌を充填し、入水、代掻後
、ヒエの種子を播種し、２葉期の水稲苗を移植し、３ｃ
ｍ１：湛水した。播種翌日に実施例４に準じて調製した
水和剤の所定量を水で希釈し水面に滴下した。調査は薬
剤処理後２１日０に第２表の基準に従い行った。調査結
果を第４表に指数で示しに。Test example 2 (paddy field weed control effect) Paddy soil was filled into a 100 cm pot, and after watering and puddling, millet seeds were sown, paddy rice seedlings at the 2-leaf stage were transplanted, and 3c
m1: Flooded with water. On the day after seeding, a predetermined amount of a wettable powder prepared according to Example 4 was diluted with water and dropped onto the water surface. The investigation was conducted 21 days after drug treatment according to the criteria in Table 2. The survey results are shown in Table 4 as an index.
試験例３（水田雑草防除効果）
１００ｃｍ’ポットに水田土壌を充填し、入水、代掻後
、ヒエの種子を播種し、３ｃ１１に湛水した。ヒエが３
葉期に達した時に実施例４に準じて調製しｔ；水利剤の
所定量を水で希釈し水面に滴下した。調査は薬剤処理後
３０日１に第２表の基準に従い行った。調査結果を第５
表に指数で示した。Test Example 3 (Paddy field weed control effect) A 100 cm' pot was filled with paddy soil, and after watering and puddling, barnyard grass seeds were sown, and the pot was flooded at 3c11. 3 barnyard grass
When it reached the leaf stage, it was prepared according to Example 4; a predetermined amount of an irrigation agent was diluted with water and dropped onto the water surface. The investigation was conducted 30 days after drug treatment according to the criteria in Table 2. 5th survey results
It is shown in the table as an index.
第１図は化合物１１の赤外吸収スペクトル図、第２図は
化合物１２の赤外吸収スペクトル図、第３図は化合物１
３の赤外吸収スペクトル図、第４図は化合物１５の赤外
吸収スペクトル図、第５図は化合物１８の赤外吸収スペ
クトル図、第６ｒＸＪは化合物２２の赤外吸収スペクト
ル図、第７図は化合物２６の赤外吸収スペクトル図、第
８図は化合物２７の赤外吸収スペクトル図、第９図は化
合物２Ｂの赤外吸収スペクトル図、第１０図は化合物２
９の赤外吸収スペクトル図である。Figure 1 is an infrared absorption spectrum diagram of compound 11, Figure 2 is an infrared absorption spectrum diagram of compound 12, and Figure 3 is an infrared absorption spectrum diagram of compound 1.
Figure 4 is an infrared absorption spectrum diagram of Compound 15, Figure 5 is an infrared absorption spectrum diagram of Compound 18, No. 6rXJ is an infrared absorption spectrum diagram of Compound 22, and Figure 7 is an infrared absorption spectrum diagram of Compound 22. FIG. 8 is an infrared absorption spectrum diagram of compound 26, FIG. 9 is an infrared absorption spectrum diagram of compound 2B, and FIG. 10 is an infrared absorption spectrum diagram of compound 2.
9 is an infrared absorption spectrum diagram of No. 9.
Claims (1)
素原子又は硫黄原子を示し、Ｙは窒素原子を１ないし３
個含み、硫黄原子を１個含んでいてもよい、５ないし６
員ヘテロ環（該環は１ないし２個の酸素原子、ハロゲン
原子、低級アルキル基、低級アルコキシ基又は低級アル
キルアミノ基で置換されていてもよい）を示す］ で表わされるフェノキシプロピオン酸アミド誘導体及び
その塩。 ２ ヘテロ環が、ピリジン環（該環は１ないし２個のハ
ロゲン原子、低級アルキル基又は低級アルコキシ基で置
換されていてもよい）、ピリミジン環（該環は１ないし
２個の酸素原子、ハロゲン原子、低級アルキル基、低級
アルコキシ基又は低級アルキルアミノ基で置換されてい
てもよい）、ピラゾール環（該環は低級アルキル基で置
換されていてもよい）、トリアジン環（該環は低級アル
キル基で置換されていてもよい）又はチアゾール環（該
環はハロゲン原子で置換されていてもよい）である請求
項１記載のフェノキシプロピオン酸アミド誘導体及びそ
の塩。 ３ 一般式 ▲数式、化学式、表等があります▼ ［式中、Ｒは水素原子又はハロゲン原子を示し、Ｘは酸
素原子又は硫黄原子を示し、Ｙは窒素原子を１ないし３
個含み、硫黄原子を１個含んでいてもよい、５ないし６
員ヘテロ環（該環は１ないし２個の酸素原子、ハロゲン
原子、低級アルキル基、低級アルコキシ基又は低級アル
キルアミノ基で置換されていてもよい）を示す］ で表わされるフェノキシプロピオン酸アミド誘導体及び
その塩を有効成分として含有する除草剤。 ４ ヘテロ環が、ピリジン環（該環は１ないし２個のハ
ロゲン原子、低級アルキル基又は低級アルコキシ基で置
換されていてもよい）、ピリミジン環（該環は１ないし
２個の酸素原子、ハロゲン原子、低級アルキル基、低級
アルコキシ基又は低級アルキルアミノ基で置換されてい
てもよい）、ピラゾール環（該環は低級アルキル基で置
換されていてもよい）、トリアジン環（該環は低級アル
キル基で置換されていてもよい）又はチアゾール環（該
環はハロゲン原子で置換されていてもよい）である請求
項１記載のフェノキシプロピオン酸アミド誘導体及びそ
の塩を有効成分として含有する除草剤。[Claims] 1 General formula ▲ Numerical formula, chemical formula, table, etc. ▼ [In the formula, R represents a hydrogen atom or a halogen atom, X represents an oxygen atom or a sulfur atom, and Y represents one or more nitrogen atoms. 3
may contain 1 sulfur atom, 5 to 6
a phenoxypropionic acid amide derivative represented by: That salt. 2 The heterocycle is a pyridine ring (the ring may be substituted with 1 or 2 halogen atoms, a lower alkyl group or a lower alkoxy group), a pyrimidine ring (the ring is substituted with 1 or 2 oxygen atoms, a halogen atom, a lower alkyl group, a lower alkoxy group, or a lower alkylamino group), a pyrazole ring (the ring may be substituted with a lower alkyl group), a triazine ring (the ring may be substituted with a lower alkyl group) The phenoxypropionic acid amide derivative and its salt according to claim 1, which is a thiazole ring (the ring may be substituted with a halogen atom) or a thiazole ring (the ring may be substituted with a halogen atom). 3 General formula▲There are mathematical formulas, chemical formulas, tables, etc.▼ [In the formula, R represents a hydrogen atom or a halogen atom, X represents an oxygen atom or a sulfur atom, and Y represents 1 to 3 nitrogen atoms.
may contain 1 sulfur atom, 5 to 6
a phenoxypropionic acid amide derivative represented by: A herbicide containing the salt as an active ingredient. 4 The heterocycle is a pyridine ring (the ring may be substituted with 1 or 2 halogen atoms, a lower alkyl group or a lower alkoxy group), a pyrimidine ring (the ring is substituted with 1 or 2 oxygen atoms, a halogen atom, a lower alkyl group, a lower alkoxy group, or a lower alkylamino group), a pyrazole ring (the ring may be substituted with a lower alkyl group), a triazine ring (the ring may be substituted with a lower alkyl group) 2. A herbicide containing the phenoxypropionic acid amide derivative and its salt as an active ingredient according to claim 1, which is a thiazole ring (the ring may be substituted with a halogen atom) or a thiazole ring (the ring may be substituted with a halogen atom).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16690088A JPH0217187A (en) | 1988-07-06 | 1988-07-06 | Phenoxypropionamide derivative and herbicide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16690088A JPH0217187A (en) | 1988-07-06 | 1988-07-06 | Phenoxypropionamide derivative and herbicide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0217187A true JPH0217187A (en) | 1990-01-22 |
Family
ID=15839714
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16690088A Pending JPH0217187A (en) | 1988-07-06 | 1988-07-06 | Phenoxypropionamide derivative and herbicide |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0217187A (en) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996021653A1 (en) * | 1995-01-13 | 1996-07-18 | Bayer Aktiengesellschaft | Acylated 5-aminopyrazoles and the use thereof to combat animal parasites |
| WO2000005956A1 (en) * | 1998-07-25 | 2000-02-10 | Dongbu Hannong Chemical Co., Ltd. | Herbicidal phenoxypropionic acid n-alkyl-n-2-fluorophenyl amide compounds |
| US6600048B2 (en) | 1998-07-25 | 2003-07-29 | Dongbu Hannong Chemical Co., Ltd. | Herbicidal phenoxypropionic acid N-alkyl-N-2-fluorophenyl amide compounds |
| KR20030065644A (en) * | 2002-01-30 | 2003-08-09 | 동부한농화학 주식회사 | Agricultural composition for prevention on annual and perennial grasses |
| KR100419856B1 (en) * | 2000-06-13 | 2004-02-25 | 한국화학연구원 | Herbicidal phenoxypropion amides |
| KR100419853B1 (en) * | 2000-05-04 | 2004-02-25 | 동부한농화학 주식회사 | Optically active herbicidal (R)-phenoxypropionic acid-N-methyl-N-2-fluorophenyl amides |
| CN101743219A (en) * | 2007-07-03 | 2010-06-16 | 株式会社庆农 | Optically active (R)-aryloxypropionic acid amides and herbicidal composition comprising same |
| CN105085506A (en) * | 2014-05-16 | 2015-11-25 | 湖南大学 | Medical application of 2-[4-(benzoxazole-2-oxyl)phenoxyl]fatty acyl pyridylamine |
| CN105315199A (en) * | 2014-07-14 | 2016-02-10 | 湖南化工研究院有限公司 | N-pyridine aryloxyphenoxy carboxylic acid derivatives, preparation method and applications thereof |
| CN106632122A (en) * | 2016-11-29 | 2017-05-10 | 江苏富鼎化学有限公司 | Benzoxazole phenoxy carboxylic acid amide compound and preparation method thereof |
| WO2019128312A1 (en) * | 2017-12-28 | 2019-07-04 | 青岛清原化合物有限公司 | 5-chlorobenzoxazole derivative, preparation method therefor, herbicidal composition and use thereof |
-
1988
- 1988-07-06 JP JP16690088A patent/JPH0217187A/en active Pending
Cited By (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996021653A1 (en) * | 1995-01-13 | 1996-07-18 | Bayer Aktiengesellschaft | Acylated 5-aminopyrazoles and the use thereof to combat animal parasites |
| US5843978A (en) * | 1995-01-13 | 1998-12-01 | Bayer Aktiengesellschaft | Acylated 5-aminopyrazoles and the use thereof to combat animal parasites |
| US5981566A (en) * | 1995-01-13 | 1999-11-09 | Bayer Aktiengesellschaft | Acylated 5-aminopyrazoles and the use thereof to combat animal parasites |
| US6100288A (en) * | 1995-01-13 | 2000-08-08 | Bayer Aktiengesellschaft | Acylated 5-aminopyrazoles and the use thereof to combat animal parasites |
| WO2000005956A1 (en) * | 1998-07-25 | 2000-02-10 | Dongbu Hannong Chemical Co., Ltd. | Herbicidal phenoxypropionic acid n-alkyl-n-2-fluorophenyl amide compounds |
| US6486098B1 (en) | 1998-07-25 | 2002-11-26 | Dongbu Hannong Chemical Co. Ltd. | Herbicidal phenoxypropionic acid N-alkyl-N-2-fluorophenyl amide compounds |
| US6600048B2 (en) | 1998-07-25 | 2003-07-29 | Dongbu Hannong Chemical Co., Ltd. | Herbicidal phenoxypropionic acid N-alkyl-N-2-fluorophenyl amide compounds |
| KR100419853B1 (en) * | 2000-05-04 | 2004-02-25 | 동부한농화학 주식회사 | Optically active herbicidal (R)-phenoxypropionic acid-N-methyl-N-2-fluorophenyl amides |
| KR100419856B1 (en) * | 2000-06-13 | 2004-02-25 | 한국화학연구원 | Herbicidal phenoxypropion amides |
| KR20030065644A (en) * | 2002-01-30 | 2003-08-09 | 동부한농화학 주식회사 | Agricultural composition for prevention on annual and perennial grasses |
| CN101743219A (en) * | 2007-07-03 | 2010-06-16 | 株式会社庆农 | Optically active (R)-aryloxypropionic acid amides and herbicidal composition comprising same |
| JP2010532345A (en) * | 2007-07-03 | 2010-10-07 | キュン・ノン・コーポレーション | Photoactive (R) -aryloxypropionic acid amide and herbicidal composition containing the same |
| US8293774B2 (en) * | 2007-07-03 | 2012-10-23 | Kyung Nong Corporation | Optically active (R)-aryloxypropionic acid amides and herbicidal composition comprising same |
| EP2183213A4 (en) * | 2007-07-03 | 2013-08-07 | Kyung Nong Corp | Optically active (r)-aryloxypropionic acid amides and herbicidal composition comprising same |
| CN105085506A (en) * | 2014-05-16 | 2015-11-25 | 湖南大学 | Medical application of 2-[4-(benzoxazole-2-oxyl)phenoxyl]fatty acyl pyridylamine |
| CN105315199A (en) * | 2014-07-14 | 2016-02-10 | 湖南化工研究院有限公司 | N-pyridine aryloxyphenoxy carboxylic acid derivatives, preparation method and applications thereof |
| CN106632122A (en) * | 2016-11-29 | 2017-05-10 | 江苏富鼎化学有限公司 | Benzoxazole phenoxy carboxylic acid amide compound and preparation method thereof |
| WO2019128312A1 (en) * | 2017-12-28 | 2019-07-04 | 青岛清原化合物有限公司 | 5-chlorobenzoxazole derivative, preparation method therefor, herbicidal composition and use thereof |
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