JPH0513160B2 - - Google Patents
Info
- Publication number
- JPH0513160B2 JPH0513160B2 JP59153986A JP15398684A JPH0513160B2 JP H0513160 B2 JPH0513160 B2 JP H0513160B2 JP 59153986 A JP59153986 A JP 59153986A JP 15398684 A JP15398684 A JP 15398684A JP H0513160 B2 JPH0513160 B2 JP H0513160B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- general formula
- halogen atom
- hydrogen atom
- positions
- 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
- 125000005843 halogen group Chemical group 0.000 claims description 54
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 51
- 125000000217 alkyl group Chemical group 0.000 claims description 50
- 230000002363 herbicidal effect Effects 0.000 claims description 40
- 125000003545 alkoxy group Chemical group 0.000 claims description 37
- 125000004414 alkyl thio group Chemical group 0.000 claims description 35
- -1 N-substituted-chloroacetanilide Chemical class 0.000 claims description 31
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 25
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 25
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 24
- 239000004009 herbicide Substances 0.000 claims description 19
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- 125000000304 alkynyl group Chemical group 0.000 claims description 13
- 238000006467 substitution reaction Methods 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 4
- 229930192474 thiophene Natural products 0.000 claims description 4
- 150000003577 thiophenes Chemical class 0.000 claims description 4
- VONWPEXRCLHKRJ-UHFFFAOYSA-N 2-chloro-n-phenylacetamide Chemical compound ClCC(=O)NC1=CC=CC=C1 VONWPEXRCLHKRJ-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 description 47
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- 241000196324 Embryophyta Species 0.000 description 22
- 239000000203 mixture Substances 0.000 description 18
- 240000007594 Oryza sativa Species 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 235000007164 Oryza sativa Nutrition 0.000 description 15
- 241000218691 Cupressaceae Species 0.000 description 14
- 235000009566 rice Nutrition 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
- 238000010521 absorption reaction Methods 0.000 description 11
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 244000184734 Pyrus japonica Species 0.000 description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 230000035784 germination Effects 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 239000012433 hydrogen halide Substances 0.000 description 7
- 229910000039 hydrogen halide Inorganic materials 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- 239000002689 soil Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 125000003368 amide group Chemical group 0.000 description 5
- 238000001819 mass spectrum Methods 0.000 description 5
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 241000234653 Cyperus Species 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 231100000674 Phytotoxicity Toxicity 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 150000001793 charged compounds Chemical class 0.000 description 4
- 230000000887 hydrating effect Effects 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000002516 radical scavenger Substances 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 241000209504 Poaceae Species 0.000 description 3
- 240000001341 Reynoutria japonica Species 0.000 description 3
- 235000018167 Reynoutria japonica Nutrition 0.000 description 3
- 241000208422 Rhododendron Species 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 3
- 229910052573 porcelain Inorganic materials 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 description 3
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 2
- 240000004731 Acer pseudoplatanus Species 0.000 description 2
- 235000002754 Acer pseudoplatanus Nutrition 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000254032 Acrididae Species 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 235000002566 Capsicum Nutrition 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 241000234646 Cyperaceae Species 0.000 description 2
- 240000003173 Drymaria cordata Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241001479611 Iris ensata Species 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
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 235000006485 Platanus occidentalis Nutrition 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 235000005324 Typha latifolia Nutrition 0.000 description 2
- 241001148683 Zostera marina Species 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000009331 sowing Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- MJAIDSKATIEQHM-UHFFFAOYSA-N 3-(chloromethyl)-2-iodothiophene Chemical compound ClCc1ccsc1I MJAIDSKATIEQHM-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 1
- 235000004135 Amaranthus viridis Nutrition 0.000 description 1
- 244000204909 Anoda cristata Species 0.000 description 1
- 241000254060 Aquatica lateralis Species 0.000 description 1
- 235000015701 Artemisia arbuscula Nutrition 0.000 description 1
- 235000002657 Artemisia tridentata Nutrition 0.000 description 1
- 235000003261 Artemisia vulgaris Nutrition 0.000 description 1
- 240000006891 Artemisia vulgaris Species 0.000 description 1
- 241001638133 Bidyanus welchi Species 0.000 description 1
- 240000007124 Brassica oleracea Species 0.000 description 1
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 235000011305 Capsella bursa pastoris Nutrition 0.000 description 1
- 240000008867 Capsella bursa-pastoris Species 0.000 description 1
- 235000008534 Capsicum annuum var annuum Nutrition 0.000 description 1
- 235000002568 Capsicum frutescens Nutrition 0.000 description 1
- 240000008574 Capsicum frutescens Species 0.000 description 1
- 240000008444 Celtis occidentalis Species 0.000 description 1
- 235000018962 Celtis occidentalis Nutrition 0.000 description 1
- 235000005940 Centaurea cyanus Nutrition 0.000 description 1
- 240000004385 Centaurea cyanus Species 0.000 description 1
- 235000009344 Chenopodium album Nutrition 0.000 description 1
- 240000000005 Chenopodium berlandieri Species 0.000 description 1
- 235000005484 Chenopodium berlandieri Nutrition 0.000 description 1
- 235000009332 Chenopodium rubrum Nutrition 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 235000004035 Cryptotaenia japonica Nutrition 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 241000241602 Gossypianthus Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 241000830562 Machlolophus holsti Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,Nâdiethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 240000008881 Oenanthe javanica Species 0.000 description 1
- 240000007019 Oxalis corniculata Species 0.000 description 1
- 235000016499 Oxalis corniculata Nutrition 0.000 description 1
- 239000006002 Pepper Substances 0.000 description 1
- 235000000405 Pinus densiflora Nutrition 0.000 description 1
- 240000008670 Pinus densiflora Species 0.000 description 1
- 235000016761 Piper aduncum Nutrition 0.000 description 1
- 240000003889 Piper guineense Species 0.000 description 1
- 235000017804 Piper guineense Nutrition 0.000 description 1
- 235000008184 Piper nigrum Nutrition 0.000 description 1
- 241001600434 Plectroglyphidodon lacrymatus Species 0.000 description 1
- 244000292697 Polygonum aviculare Species 0.000 description 1
- 235000006386 Polygonum aviculare Nutrition 0.000 description 1
- 244000234609 Portulaca oleracea Species 0.000 description 1
- 235000001855 Portulaca oleracea Nutrition 0.000 description 1
- 235000011158 Prunus mume Nutrition 0.000 description 1
- 244000018795 Prunus mume Species 0.000 description 1
- 241000681978 Rhododendron japonicum Species 0.000 description 1
- 241001092459 Rubus Species 0.000 description 1
- 235000017848 Rubus fruticosus Nutrition 0.000 description 1
- 241000124033 Salix Species 0.000 description 1
- 241001247145 Sebastes goodei Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 235000015724 Trifolium pratense Nutrition 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 240000000260 Typha latifolia Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- XCSGPAVHZFQHGE-UHFFFAOYSA-N alachlor Chemical compound CCC1=CC=CC(CC)=C1N(COC)C(=O)CCl XCSGPAVHZFQHGE-UHFFFAOYSA-N 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000005336 allyloxy group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000006295 amino methylene group Chemical group [H]N(*)C([H])([H])* 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000012752 auxiliary agent Substances 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
- 235000021029 blackberry Nutrition 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
- 239000006227 byproduct Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000001390 capsicum minimum Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000002734 clay mineral Substances 0.000 description 1
- 244000118869 coast club rush Species 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000002837 defoliant Substances 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 125000006351 ethylthiomethyl group Chemical group [H]C([H])([H])C([H])([H])SC([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 239000003630 growth substance Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 125000004372 methylthioethyl group Chemical group [H]C([H])([H])SC([H])([H])C([H])([H])* 0.000 description 1
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
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- 238000002156 mixing Methods 0.000 description 1
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The present invention relates to a novel N-substituted-chloroacetanilide having a specific general formula and a process for producing the same. The present invention also provides a herbicide containing the above compound as an active ingredient. Conventionally, many compounds similar to N-substituted chloroacetanilide have been synthesized.
Certain species are already known to be useful as herbicides. For example, US Patent No.
No. 3901917 has a general formula, (However, R 9 and R 10 are each a hydrogen atom or an alkyl group, R 7 is an alkyl group, R 8 is a hydrogen atom,
an alkyl group or an alkoxy group; X represents a halogen atom; Y represents a hydrogen atom, a lower alkyl group or a halogen atom; It has been described that N-(2-thienylmethyl)-substituted-haloacetanilides represented by ) are useful as field herbicides. However, the effective concentration of the compound represented by the above general formula described in the U.S. patent as a field herbicide varies slightly depending on the type of weed, but in all cases, it is 8 pounds/acre. That is, it is approximately 900 g/10a, and it is clear that the above compound must be administered in extremely large amounts to be effective as a herbicide. In addition, when the compound represented by the above general formula is used as a herbicide for rice fields, there are some that have herbicidal activity at relatively low concentrations such as 125g/10a.
These have the disadvantage of causing phytotoxicity to paddy rice. On the other hand, conventionally commercially available N-substituted chloroacetanilide herbicides such as brachlor and alachlor have herbicidal activity against paddy field weeds at relatively low concentrations, as is clear from the comparative examples described below. However, these also have the major drawback of causing undesirable phytotoxicity to paddy rice at concentrations that have herbicidal activity. When herbicides are used in high concentrations, the herbicidal active substances flow into rivers, causing undesirable chemical damage to various aquatic animals, and furthermore having a negative impact on humans and livestock. .
Furthermore, it is clear that herbicides that exhibit strong herbicidal activity at relatively low concentrations but also cause phytotoxicity to paddy rice will have a major detrimental effect on increasing the per-cell yield of rice, which is the original objective. From this perspective,
There has been a strong desire to develop a new herbicide having a so-called selective herbicidal activity, which has a herbicidal effect even when used at low concentrations and kills only weeds. The present inventors have conducted extensive research in order to find a new compound that has excellent properties as a herbicide that satisfies the above-mentioned requirements. As a result, we succeeded in synthesizing an excellent new compound that compensates for the various drawbacks mentioned above, and completed the present invention. That is, the present invention is based on the general formula, N-substituted-chloroacetanilide represented by (wherein R 1 and R 2 are the same or different hydrogen atoms,
Represents a halogen atom, an alkyl group, an alkoxy group, an alkylthio group, an alkoxyalkyl group, an alkylthioalkyl group, and R represents a halogen atom, an alkyl group, an alkoxy group, an alkylthio group, an alkoxyalkyl group, an alkylthioalkyl group.
R 3 , R 4 and R 5 each represent the same or different hydrogen atom, halogen atom, alkyl group, alkenyl group, alkynyl group, alkoxy group, or alkylthio group, and R 6 represents a hydrogen atom or an alkyl group. However, R 1 or R 2 is a hydrogen atom, and R
and R 2 or R and R 1 are both the same kind of halogen atoms, the substitution positions of R and R 2 or R and R 1 are the 2- and 4-positions, or the 4- and 5-positions of the thiophene ring. . ) Furthermore, the present invention also relates to the general formula, N-substituted-aniline represented by the general formula,
A general formula characterized by reacting with chloroacetyl halide represented by ClCH 2 COX, A method for producing an N-substituted chloroacetanilide represented by (wherein R 1 and R 2 are the same or different hydrogen atoms, halogen atoms, alkyl groups,
An alkoxy group, an alkylthio group, an alkoxyalkyl group, an alkylthioalkyl group, R represents a halogen atom, an alkyl group, an alkoxy group, an alkylthio group, an alkoxyalkyl group, an alkylthioalkyl group, R 3 , R 4 and R 5 each represent It represents the same or different hydrogen atom, halogen atom, alkyl group, alkenyl group, alkynyl group, alkoxy group, or alkylthio group, and R 6 represents a hydrogen atom or an alkyl group. However, if R 1 or R 2 is a hydrogen atom and R and R 2 or R and R 1 are both the same type of halogen atom, the substitution position of R and R 2 or R and R 1 is on the thiophene ring. 2nd and 4th place,
Or 4th and 5th place. Moreover, Y is a halogen atom. ) as well as the general formula, Substituted thiophene and general formula represented by, A general formula characterized by reacting with chloroacetanilide represented by A method for producing an N-substituted chloroacetanilide represented by (wherein R 1 and R 2 are the same or different hydrogen atoms, halogen atoms, alkyl groups,
An alkoxy group, an alkylthio group, an alkoxyalkyl group, an alkylthioalkyl group, R represents a halogen atom, an alkyl group, an alkoxy group, an alkylthio group, an alkoxyalkyl group, an alkylthioalkyl group, and R 3 , R 4 and R 5 each represent They represent the same or different hydrogen atoms, halogen atoms, alkyl groups, alkenyl groups, alkynyl groups, alkoxy groups, and alkylthio groups, and R 6 represents a hydrogen atom or an alkyl group. However, if R 1 or R 2 is a hydrogen atom and R and R 2 or R and R 1 are the same type of halogen atom, R and R 2 or R
The substitution positions of R 1 are the 2nd and 4th positions, or the 4th and 5th positions of the thiophene ring. Moreover, Y is a halogen atom. ) is also provided. Furthermore, the present invention provides the general formula, (In the formula, R 1 and R 2 represent the same or different hydrogen atoms, halogen atoms, alkyl groups, alkoxy groups, alkylthio groups, alkoxyalkyl groups, and alkylthioalkyl groups, and R is a halogen atom, an alkyl group, or an alkoxy group. , an alkylthio group, an alkoxyalkyl group, an alkylthioalkyl group, and R 3 , R 4 and R 5 each represent the same or different hydrogen atom, halogen atom, alkyl group, alkenyl group, alkynyl group, alkoxy group, or alkylthio group, R 6 represents a hydrogen atom or an alkyl group.However, when R 1 or R 2 is a hydrogen atom and R and R 2 or R and R 1 are both the same type of halogen atom, R and R 2 or The substituent positions of R and R 1 are the 2nd and 4th positions, or the 4th and 5th positions of the thiophene ring. . The N-substituted-chloroacetanilide of the present invention has the general formula: (In the formula, R 1 and R 2 represent the same or different hydrogen atoms, halogen atoms, alkyl groups, alkoxy groups, alkylthio groups, alkoxyalkyl groups, and alkylthioalkyl groups, and R is a halogen atom, an alkyl group, or an alkoxy group. , an alkylthio group, an alkoxyalkyl group, an alkylthioalkyl group, and R 3 , R 4 and R 5 each represent the same or different hydrogen atom, halogen atom, alkyl group, alkenyl group, alkynyl group, alkoxy group, or alkylthio group, R 6 represents a hydrogen atom or an alkyl group.However, when R 1 or R 2 is a hydrogen atom and R and R 2 or R and R 1 are both the same type of halogen atom, R and R 2 or The substitution positions of R and R 1 are the 2nd and 4th positions, or the 4th and 5th positions of the thiophene ring. In the above general formula, specific examples of halogen atoms represented by R, R 1 , R 2 , R 3 , R 4 and R 5 include chlorine,
Examples include bromine, fluorine, and iodine atoms. Furthermore, in the general formula, the alkyl groups represented by R, R 1 , R 2 , R 3 , R 4 , R 5 and R 6 may be linear or branched, and have a carbon number of is not particularly limited. However, due to the ease of obtaining raw materials, the number of carbon atoms is 1.
It is preferable that the number is 6 to 6. Specific examples of the alkyl group include methyl group, ethyl group, n-
propyl group, iso-propyl group, n-butyl group,
iso-butyl group, t-butyl group, n-pentyl group,
Examples include n-hexyl group. Furthermore, in the general formula, the alkenyl groups represented by R 3 , R 4 and R 5 are:
The number of carbon atoms is not particularly limited, regardless of whether it is linear or branched. However, due to the ease of obtaining raw materials, the number of carbon atoms is 1.
It is suitable that it is 4 pieces. Specific examples of the alkenyl group include vinyl group, allyl group,
Examples include iso-propenyl group, 2-butenyl group, and 3-butenyl group. Furthermore, in the general formula,
The alkynyl group represented by R 3 , R 4 and R 5 may be linear or branched, and the number of carbon atoms is not particularly limited, but it is preferable that the number of carbon atoms is 1 to 4 as described above. It is. Specific examples of the alkynyl group include ethynyl group, 2-propynyl group, and the like. In the above general formula, the alkoxy group represented by R, R 1 , R 2 , R 3 , R 4 and R 5 has 1 to 1 carbon atoms.
Six linear or branched saturated or unsaturated groups are preferred, and specific examples of the alkoxy group include methoxy group, ethoxy group, n-propoxy group, t-butoxy group, n-pentoxy group. group, n-
Examples include hexoxy group and allyloxy group.
Furthermore, in the general formula, R, R 1 , R 2 , R 3 , R 4 and
The alkylthio group represented by R 5 is preferably a linear or branched saturated or unsaturated group having 1 to 6 carbon atoms, and specific examples of the alkylthio group include methylthio group, ethylthio group, n -propylthio group, t-butylthio group, n-pentylthio group, n-hexylthio group, allylthio group and the like. Furthermore, in the above general formula, the alkoxyalkyl group represented by R, R 1 and R 2 is preferably a linear or branched saturated or unsaturated group having 2 to 6 carbon atoms; Specific examples include a methoxymethyl group, a methoxyethyl group, an ethoxymethyl group, an n-propoxymethyl group, a t-butoxyethyl group, an allyloxyethyl group, and the like. Furthermore, in the general formula,
The alkylthioalkyl group represented by R, R 1 and R 2 is preferably a linear or branched saturated or unsaturated group having 2 to 6 carbon atoms, and specific examples of the alkylthioalkyl group include: Examples include methylthiomethyl group, methylthioethyl group, ethylthiomethyl group, n-propylthiomethyl group, t-butylthioethyl group, and allylthioethyl group. In the N-substituted-chloroacetanilide represented by the general formula (1), R is an alkoxy group, an alkoxyalkyl group, or a halogen atom, and R 1 and R 2 are a hydrogen atom, an alkoxy group, an alkoxyalkyl group,
A halogen atom is preferred because it exhibits high herbicidal activity even at a low dose. Further, it is preferable that the substituents (excluding hydrogen atoms) represented by R, R 1 and R 2 of the thiophene ring are substituted at the 2-position because the herbicidal activity is high even at a low dosage.
Furthermore, there is a tendency that herbicidal activity is higher when R 6 is a hydrogen atom. As is clear from the examples described below, the compound represented by the general formula (1) of the present invention is completely harmless and safe to rice even when used at a high concentration, for example, 500g/10a. Without,
Even when used at a low concentration of 125g/10a or lower, it has an extremely strong herbicidal activity that can completely kill various paddy field weeds such as field weeds, cypresses, bulrushes, and grasshoppers. Furthermore, as is clear from the Examples described below, it exhibits complete selective herbicidal activity against wild grasses that have grown up to the 1.5 leaf stage at a low concentration of 125 g/10a. Such remarkable selective herbicidal activity is hardly affected by the type of substituent introduced into the aniline ring, as is clear from comparison with the comparative example described below.
This is a specific effect brought about by the 3-thienyl group present in the molecule. The compound represented by the general formula (1) of the present invention is a novel compound, and its structure can be confirmed by the following means. (a) By measuring the infrared absorption spectrum IR, it is possible to observe an absorption based on a CH bond in the vicinity of 3150 to 2820 cm -1 and a characteristic absorption based on the carbonyl bond of the amide group in the vicinity of 1680 to 1670 cm -1 . (b) By measuring the mass spectrum MS and calculating the composition formula corresponding to each observed peak (generally the mass number expressed as m/e, which is the ion molecular weight m divided by the ion charge number e), It is possible to know the molecular weight of the compound subjected to measurement and the bonding mode of each atomic group within the molecule. In other words, the sample subjected to measurement is expressed by the general formula, When expressed as The molecular weight of can be determined. Furthermore, regarding the compound of the present invention represented by the above general formula, M
-X, M-COCH 2 X (X represents a halogen atom) and A characteristic strong peak corresponding to the molecule is observed, and the bonding mode of the molecule can be known. (c) 1 H-Nuclear Magnetic Resonance Spectrum ( 1 H-NMR)
By measuring , it is possible to know the bonding mode of hydrogen atoms present in the compound of the present invention represented by the above general formula. A representative example of 1 H-NMR (ÎŽ, ppm: based on tetramethylsilane, in deuterated chloroform solvent) of the compound represented by the general formula (1) is N-(2'-iodo-3'-thienylmethyl)-N Figure 1 shows the 'H-NMR of -chloroaceto-2,6-dimethylanilide. The analysis results are as follows. That is, a single line corresponding to 6 protons was observed at 1.90 ppm, and can be attributed to the methyl group (a) substituted at the 2 and 6 positions of the phenyl group. A single line corresponding to two protons was observed at 3.63 ppm, and can be attributed to the methylene group (b) in the chloroacetyl group. A single line corresponding to two protons was observed at 4.73 ppm, and can be attributed to the methylene group (c). Furthermore, a multiplet corresponding to five protons was observed at 6.90 to 7.40 ppm, and can be attributed to protons (d) substituted with phenyl and thienyl groups. 1 Hâ of the compound represented by the above general formula (1)
To summarize the characteristics of NMR, the methylene proton of the chloroacetyl group is usually a single line with 3.6 ~
around 3.8 ppm, and the methylene proton of aminomethylene group is around 4.8 ppm as a single line (however,
When the 2- and 6-positions on the aniline side are substituted with different functional groups, a double line may appear. ), the proton on the thiophene ring side is 6.4 ~
7.4ppm, protons on the benzene side are 6.5~
It tends to show a characteristic peak at 7.7ppm. (d) Calculate the weight percent of oxygen by determining the weight percent of each of carbon, hydrogen, nitrogen, sulfur, and halogen by elemental analysis, and then subtracting the sum of the weight percent of each recognized element from 100. is possible,
Therefore, the compositional formula of the compound can be determined. The N-(3'-thienylmethyl)-N-chloroacetanilide of the present invention has R, R 1 ,
The properties of R 2 , R 3 , R 4 , R 5 and R 6 vary depending on the type, but they are generally pale yellow or yellow viscous liquids or solids at room temperature and normal pressure, and have an extremely high boiling point. There are many things. As will be specifically shown in the examples below, the boiling point of the above compound tends to increase as the molecular weight increases, like general organic compounds. The compounds of the present invention are soluble in common organic solvents such as benzene, ether, alcohol, chloroform, carbon tetrachloride, hexane, acetonitrile, N,N-dimethylformamide, and dimethyl sulfoxide, but are almost insoluble in water. The method for producing the compound represented by the above general formula (1) of the present invention is not particularly limited. A typical manufacturing method is described below. general formula, (In the formula, R 1 and R 2 are hydrogen atoms, halogen atoms,
An alkyl group, an alkylthio group, an alkoxyalkyl group, an alkylthioalkyl group, R represents a halogen atom, an alkyl group, an alkoxy group, an alkylthio group, an alkoxyalkyl group, an alkylthioalkyl group, and R 3 , R 4 and R 5 each represent It represents the same or different hydrogen atom, halogen atom, alkyl group, alkenyl group, alkynyl group, alkoxy group, or alkylthio group, and R 6 represents a hydrogen atom or an alkyl group. However, if R 1 or R 2 is a hydrogen atom and R and R 2 or R and R 1 are both the same type of halogen atom, the substitution position of R and R 2 or R and R 1 is on the thiophene ring. 2nd and 4th place,
Or 4th and 5th place. ) is reacted with chloroacetyl halide represented by the general formula ClCH 2 COX (where X represents a halogen atom) to produce a compound represented by the general formula (1) A compound is obtained. The aniline derivative represented by the above general formula (2) serving as a raw material may be obtained by any method. A typical method for producing the aniline may be, for example, the method described in Reference Examples below. In the reaction between the compound represented by the general formula (2) and chloroacetyl halide, the molar ratio of both compounds may be appropriately determined as necessary, but it is usually the same molar ratio or a slightly excess molar amount of chloroacetyl halide. It is common to use Further, in the above reaction, hydrogen halide is produced as a by-product. This hydrogen halide is expressed by the general formula (2) in the reaction system.
It is usually preferable to coexist a hydrogen halide scavenger in the reaction system since it reacts with the compound represented by the formula and causes a decrease in the yield of the product.
The hydrogen halide scavenger is not particularly limited, and any known one can be used. Trialkylamines such as trimethylamine, triethylamine, and tripropylamine; pyridine; sodium alcoholate;
Examples include sodium carbonate, potassium carbonate, sodium hydrogen carbonate, magnesium carbonate, and the like. It is generally preferable to use an organic solvent in the reaction in the present invention. Examples of solvents preferably used include aliphatic or aromatic hydrocarbons such as benzene, toluene, xylene, hexane, heptane, petroleum ether, chloroform, methylene chloride, and ethylene chloride, or halogenated hydrocarbons. Ethers such as diethyl ether, dioxane, and tetrahydrofuran; Ketones such as acetone and methyl ethyl ketone; Nitriles such as acetonitrile; N,N-dialkyl amides such as N,N-dimethylformamide and N,N-diethylformamide; Examples include dimethyl sulfoxide. The order of addition of the raw materials in the reaction is not particularly limited, but generally, the compound represented by the general formula (2) is dissolved in a solvent, charged into a reactor, and the chloroacetohalogenide dissolved in the solvent is added under stirring. Good. Of course, it is also possible to continuously add raw materials to the reaction system and take out the produced reactants continuously from the reaction system. The temperature in the reaction can be selected from a wide range, generally -20°C to 150°C, preferably 0°C to 120°C.
It is sufficient to choose from the range of °C. Although the reaction time varies depending on the type of raw materials, it is usually sufficient to select from a range of 5 minutes to 10 days, preferably 1 to 40 hours. Further, it is preferable to stir the reaction mixture during the reaction. The method for isolating and purifying the target product, ie, the compound represented by the general formula (1) above, from the reaction system is not particularly limited, and any known method can be employed. For example, the reaction solution is cooled or allowed to cool naturally to return to room temperature or near room temperature, the reaction solvent and the remaining hydrogen halide scavenger are distilled off, and the residue is extracted with an organic solvent such as benzene, ether, or chloroform. In the above operation, the salt and high molecular weight compound produced from the by-produced hydrogen halide and the hydrogen halide scavenger are separated.
The organic solvent layer is dried with a drying agent such as mirabilite or calcium chloride, and then the organic solvent is distilled off.
The target product is obtained by vacuum distilling the residue. In addition to isolation and purification by vacuum distillation, it can also be purified by chromatography or, if the product is a solid, by crystallization from a solvent such as hexane. Furthermore, the compound represented by the general formula (1) of the present invention is represented by the general formula: (In the formula, R 1 and R 2 are hydrogen atoms, halogen atoms,
An alkyl group, an alkoxy group, an alkylthio group, an alkoxyalkyl group, an alkylthioalkyl group, R is a halogen atom, an alkyl group, an alkoxy group, an alkylthio group, an alkoxyalkyl group,
It represents an alkylthioalkyl group, and R 6 represents a hydrogen atom or an alkyl group. However, if R 1 or R 2 is a hydrogen atom and R and R 2 or R and R 1 are both the same type of halogen atom, the substitution position of R and R 2 or R and R 1 is on the thiophene ring. 2nd and 4th place,
Or 4th and 5th place. Moreover, X represents a halogen atom. ) substituted thiophene and the general formula, (In the formula, R 3 , R 4 and R 5 each represent the same or different hydrogen atom, halogen atom, alkyl group, alkenyl group, alkynyl group, alkoxy group, or alkylthio group). It can also be obtained by The substituted thiophene and the chloroacetanilide used as raw materials can be obtained by any method. In addition, the conditions and isolation and purification method for carrying out the reaction are the same as those used in the reaction of the N-substituted aniline represented by the general formula (2) and chloroacetyl halide described above. Almost the same conditions as in the method can be adopted. The compound represented by the general formula (1) of the present invention exhibits remarkable effects as a herbicide. For example, it exhibits excellent herbicidal effects in soil treatment before and after germination of grass weeds, broad-leaved weeds, and perennial weeds. In particular, it shows a remarkable herbicidal effect on grass weeds, and for example, it shows an excellent herbicidal effect on grasses, which are harmful weeds, not only when they germinate, but also when they grow at the 1.5 leaf stage. Furthermore, it is highly safe for paddy rice not only for seedlings at the 1.5-leaf stage but also during germination. As it has a highly selective herbicidal effect, it is an excellent herbicide with a significantly longer suitable treatment period than conventional herbicides. It also exhibits a selective herbicidal effect when used as a herbicide in upland fields, so it can be applied not only to broad-leaved crops such as soybeans, cotton, and cornflowers, but also to gramineous crops such as wheat, barley, corn, and upland rice without causing damage. I can do it. Representative examples of specific embodiments in which the compound represented by the general formula (1) is used as a herbicide will be described below. When the compound represented by the above general formula (1) is used for wildflowers and paddy rice that are sown simultaneously in paddy field soil, when treated at a concentration of 30g per 10 ares, the germination of wildflowers is completely inhibited, but the germination of rice plants is Even when processing 1000g, there is no effect at all. Therefore, generally 10
It may be used in paddy fields in an amount of 6.25g to 2000g, preferably 30g to 500g, of the active ingredient per area. As mentioned above, it has selective herbicidal activity between wildflowers and paddy rice, so it can be applied during the long-term growth stage of paddy rice from the germination period to the growing period, and has the advantage that it can be applied extremely safely, especially to flooded and directly sown paddy rice. This is a major feature of the present invention. Although the compounds represented by the general formula (1) of the present invention have slightly different herbicidal effects depending on their functional groups, they have little phytotoxicity against gramineous crops, and are particularly phytotoxic to paddy rice. Few points are common characteristics. Examples of weeds on which the compound of the present invention exhibits herbicidal effects are as follows. As mentioned above, it has a high herbicidal effect on grass family weeds, especially grasshoppers, and has a particularly favorable herbicidal effect on Cyperaceae, especially Cyperaceae, bulrush, and the like. Next to these, it is preferable to mix and use known herbicides such as phenoxy compounds, amide compounds, etc., which have a herbicidal effect on broad-leaved weeds, but increase the amount of active ingredients used. Weeds that can be particularly effectively weeded include,
Japanese cabbage, Japanese cypress, Japanese cypress, Japanese cypress, Japanese cypress, Japanese cypress, Japanese firefly, Japanese cypress, Japanese cypress, Japanese cypress, Hyderico, Japanese cyperus, Japanese cypress, Japanese black bream, Japanese pine fly, Japanese yellow tit, Japanese cypress, Aginia, Japanese yellowtail, Japanese cypress, Japanese cypress, Japanese cypress,
These are paddy field weeds such as Japanese parsley, willow knotweed, Japanese wattle, Japanese iris, Japanese iris, Japanese chickweed, Japanese sagebrush, Japanese commonweed, Japanese chickweed, Japanese thornweed, Japanese knotweed, Japanese reddish weed, Japanese knotweed, Japanese azalea, Japanese japonica, Japanese japonica, Japanese japonica, red cottonweed, sour chili pepper, Japanese apricot, azalea, and red capsicum. In addition, the field weeds can be applied to, for example, blackberry, hackberry, pigweed, Japanese knotweed, cyperus japonica, cyperus japonica, japonica, purslane, red clover, oxalis, sycamore, sycamore, japonica, japonica, japonica, cyperus japonica, shepherd's purse, etc. Furthermore, since the compound represented by the general formula (1) of the present invention affects the growth of plants, it can also be used as a defoliant, a germination inhibitor, and a growth regulator. The mode of use of the above general formula (1) of the present invention is not particularly limited, and the mode of use of known herbicides can be used as is. For example, it can be used in any dosage form such as granules, powders, emulsions, wettable powders, tablets, oils, aerosols, and smokes using inert solid carriers, liquid carriers, emulsifying dispersants, etc. Of course, auxiliary agents for formulation, such as spreading agents, diluents, surfactants, solvents, etc., can also be added as appropriate. The compound represented by the general formula (1) of the present invention can also be used in combination with insecticides, fungicides, other agricultural chemicals, fertilizer substances, soil conditioners, and the like. EXAMPLES In order to explain the present invention more specifically, Examples and Comparative Examples will be described below, but the present invention is not limited to these Examples. Example 1 N-(2'-methoxy-3'-thienylmethyl)-
Dissolve 1.49g (6.03mmole) of 2,6-dimethylaniline in 20ml of benzene and add 0.79g of triethylamine.
(7.84 mmole) and placed in ice water. Then, 10 ml of a solution of 0.82 g (7.28 mmole) of chloroacetyl chloride in benzene was slowly added. After stirring for 3 hours, the mixture was heated at 50°C for 30 minutes. After returning the reaction solution to room temperature, add 50 ml of water, 50 ml of 2N hydrochloric acid, and then 50 ml of water.
The benzene layer was dried over anhydrous sodium sulfate. After removing benzene, vacuum distillation is carried out,
1.06 g of a pale yellow solid with a boiling point of 167° C./0.5 mmHg was obtained.
The results of measuring the infrared absorption spectrum of this material are shown in Figure 2, and the C
Absorption based on the -H bond and strong absorption based on the carbonyl bond of the amide group at 1670 cm -1 were observed. Its elemental analysis values are C59.34%, H5.59%, N4.34
%, calculated values for the composition formula C 16 H 18 NSO 2 Cl (323.84): C59.34%, H5.60%, N4.32%
There was good agreement. In addition, when mass spectra were measured, m/
Molecular ion peak corresponding to molecular weight at e323, M
, m/e288 has a peak corresponding to M-Cl, m/
Peak corresponding to M-COCH 2 Cl at e246, m/
to e127
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ïŒã«Each peak corresponding to [Formula] is shown. Furthermore, 1 H-nuclear magnetic resonance spectrum (ÎŽ:
The results of measuring ppm (based on tetramethylsilane, deuterated chloroform solvent) are shown in FIG. The analysis results were as follows. A single line corresponding to 6 protons is shown at 2.01 ppm, and the two methyl groups substituted at the 2 and 6 positions of the phenyl group are shown.
Corresponds to the methyl proton in (a). A single line for three protons is shown at 3.49ppm, and three (b) of methoxy groups are shown.
corresponds to the methyl proton of A single line for two protons is shown at 3.65 ppm, which corresponds to the methylene proton in (c). A single line for two protons is shown at 4.68 ppm, which corresponds to the methylene proton in (d) adjacent to the thiophene ring. A quartet of two protons is shown at 6.63 ppm, which corresponds to the proton of the thiophene ring in (e). Furthermore, a multiplet of three protons is shown at 7.03 to 7.17 ppm, which corresponds to the proton of the benzene ring in (f). From the above results, the isolated product is N-[3â²-(2â²-
It became clear that it was methoxy)thienylmethyl]-N-chloroaceto-2,6-dimethylanilide (Compound No. 1). The yield is based on the N-
[2'-methoxy-(3'-thienylmethyl]-2,6
-54.3% for dimethylaniline
(3.28 mmole). Example 2 2.04 g (10.3 mmole) of 2,9-dimethyl-N-chloroacetanilide, 2.67 g (10.3 mmole) of 2-iodo-3-chloromethylthiophene, and 0.71 g (5.15 mmole) of potassium carbonate were mixed with N,N- Add to 50ml of dimethylformamide (hereinafter abbreviated as DMF),
Stirred. The reaction mixture was heated at 100° C. for 3 hours and then stirred at room temperature for 1 hour. After filtering off the precipitated potassium chloride, DMF in the filtrate was distilled off under reduced pressure, 100 ml of water was added to the residue, and the mixture was extracted with ether. After drying the ether layer over anhydrous sodium sulfate, the ether was distilled off under reduced pressure. Add 100 ml of hexane-ether (10:1) to the residue, and after heating,
After cooling and recrystallization, 0.56 g of a white solid was obtained. When we measured the infrared spectrum of this material, we found that there was an absorption based on C-H bond at 3100 to 2800 cm -1 .
A strong absorption was observed at 1670 cm -1 due to the carbonyl bond of the amide group. Its elemental analysis value is C42.93%,
H3.60%, N3.33%, composition formula
This is the calculated value for C 15 H 15 SONICl (419.70)
It matched well with C42.92%, H3.61%, and N3.34%. In addition, when mass spectra were measured, m/
Molecular ion peak corresponding to molecular weight at e419, M
, m/e384 has a peak corresponding to M-Cl, m/
peak corresponding to M-COCH 2 Cl at e343, m/
to e223 (100%)
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ïŒã«Each peak corresponding to [Formula] is shown. Furthermore, the 1 H-nuclear magnetic resonance spectrum is as shown in FIG. 1 as a specific example in the specification. From the above results, it is clear that the isolated product is N-[3'-(2'-
iodo)-thienylmethyl]-N-chloroaceto~
It became clear that it was 2,6-dimethylanilide (compound number 2). The yield is 13% based on 2,6-dimethyl-N-chloroacetanilide.
(1.34 mmole). Example 3 N-[3'-(2'-methoxy)- in Example 1
2.85 g of N-[3'-(2'-methoxymethyl)-thienylmethyl]-2,6-dimethylaniline instead of thienylmethyl]-2,6-dimethylaniline
(11 mmole) was reacted and treated in the same manner as in Example 1, and the boiling point was 160°C/0.15 mmole.
2.65 g of pale yellow solid Hg was obtained. As a result of measuring the infrared spectrum of this material, C-
Absorption due to H bond and strong absorption due to carbonyl bond of amide group at 1670 cm -1 were observed. Its elemental analysis values are C60.43%, H5.98%, N4.17%,
It matched well with the calculated values of C60.42%, H5.98%, and N4.15% for the composition formula C 17 H 20 NSO 2 Cl (337.86). In addition, when mass spectra were measured, m/
Molecular ion peak corresponding to molecular weight at e337, M
, the peak corresponding to M-Cl at m/e302, m/
Peak corresponding to M-COCH 2 Cl at e261, m/
to e141 (100%)
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The results of measuring ppm (based on tetramethylsilane, deuterium chloroform solvent) are shown in FIG. The analysis results are as follows. A single line corresponding to 6 protons is shown at 1.94 ppm, which corresponds to the methyl proton in (a) substituted at the 2 and 6 positions of the phenyl group. A single line corresponding to three pyrotons is shown at 3.18 ppm, which corresponds to the methyl proton in (b) of the methoxymethyl group. A single line for two protons is shown at 3.67 ppm, which corresponds to the methylene proton in (d).
A single line corresponding to two protons is shown at 4.14 ppm, which corresponds to the methylene proton in (c) of the methoxymethyl group. A single line for two protons is shown at 4.83ppm,
It corresponds to the methylene proton in (e) adjacent to the thiophene ring. A multiplet of five protons is shown at 6.87 to 7.31 ppm, corresponding to protons (f) and (g) of the thiophene ring and benzene ring, respectively. From the above results, it was revealed that the isolated product was N-[3'(2'-methoxymethyl)-thienylmethyl]-N-chloroaceto-2,6-dimethylanilide (Compound No. 3). . The yield was 72.0% based on the N-[3'-(2'-methoxymethyl)-thienylmethyl]-2,6-dimethylaniline used.
(7.85 mmole). Example 4 N-[3'-(2'-methoxy)- in Example 1
N-[3'-(2'-methylthio-5'-methyl) instead of thienylmethyl]-2,6-dimethylaniline
-thienylmethyl]-2,6-dimethylaniline
The reaction was carried out in the same manner as in Example 1 except that 2.85g (10.3mmole) was used, and then the treatment was carried out to achieve a boiling point of 183â/
2.03 g of pale yellow solid with 0.5 mmHg was obtained. As a result of measuring the infrared spectrum of this substance, it is 3120 to 2900 cm -1
It showed an absorption based on the C-H bond at 1670 cm -1 and a strong absorption based on the carbonyl bond of the amide group at 1670 cm -1 . Its elemental analysis values are C58.04%, H6.01%, N4.02%, and the calculated values for the composition formula C 17 H 20 NS 2 OCl (353.92) are C57.52%, H 5.98%, It matched well with N3.95%. In addition, when mass spectra were measured, m/
Molecular ion peak corresponding to molecular weight at e353, M
, m/e318 has a peak corresponding to MâCl, m/
Peak corresponding to M-COCH 2 Cl at e277, m/
to e157 (100%)
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ããEach peak corresponding to [Formula] is shown. Furthermore, 1 H-nuclear magnetic resonance spectrum (ÎŽ;
The results of measuring ppm (based on tetramethylsilane, deuterated chloroform solvent) are shown in FIG. The analysis results are as follows. A single line corresponding to three protons is shown at 1.90 ppm, which corresponds to the methyl proton in (a) substituted at the 5-position of the thiophene ring. A single line corresponding to 6 protons is shown at 1.99 ppm, which corresponds to the methyl proton in (b) substituted at the 2 and 6 positions of the phenyl group. 3 protons at 2.40ppm
A single line is shown, which corresponds to the methyl proton in (c) of the methylthio group substituted at the 2-position of the thiophene ring. A single line for two protons is shown at 3.65ppm (d)
corresponds to methylene proton. A single line for two protons is shown at 4.79 ppm, which corresponds to the methylene proton in (e) adjacent to the thiophene ring. 6.90ppm
shows a single line for one proton, which corresponds to proton (f) of the thiophene ring. A multiplet of three protons is shown at 6.98 to 7.20 ppm, which corresponds to the proton (g) of the benzene ring. From the above results, the isolated product is N-[3â²-(2â²-
Methylthio-5'-methyl)]-N-chloroaceto-
It became clear that it was 2,6-dimethylanilide (compound number 4). The yield is based on the N-
[3'-(2'-methylthio-5'-methyl)]-2,6
â
55.8% (5.74 mmole) for dimethylaniline
It was hot. Example 5 By a method similar to that described in detail in Example 1, the N-substituted-chloroacetanilides listed in Table 1 were synthesized. Table 1 also abbreviates the aspects, physical properties (boiling point), characteristic absorption values in the infrared absorption spectrum, and elemental analysis results of the synthesized N-substituted-chloroacetanilide compounds.
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šæ¯æ»ã衚瀺ãããã®ã§ããã[Table] Formulation example 1 (hydrating powder) N-[3'-(2'-methoxy)-thienylmethyl]-N-chloroacet-2 obtained in Example 1,
10 parts of 6-dimethylanilide, 85 parts of a 2:1 mixture of ziecrite and kunilite (product name: Kunimine Co., Ltd., both clay minerals), and 5 parts of Solpol 800A (product name: Toho Chemical Industry Co., Ltd.) as a surfactant were uniformly mixed. The mixture was mixed and ground to obtain a 10% wettable powder. Formulation Example 2 (Emulsion) N-[3'-(2'-iodo)-thienylmethyl]-N-chloroacet-2 obtained in Example 2,
Mix and dissolve 20 parts of 6-dimethylanilide, 70 parts of xylene, and 10 parts of Solpol 800A as a surfactant.
A 20% emulsion was obtained. Formulation example 3 (granules) N-[3'-(2'-methoxymethyl)-thienylmethyl]-N-chloroaceto- obtained in Example 3
5 parts of 2,6-dimethylanilide, 50 parts of bentonite
After homogeneously mixing and pulverizing 40 parts of Kunilite and 5 parts of Solpol 800A as a surfactant, add water and stir evenly to make a paste, extrude it through a knot hole with a diameter of 0.7 mm and dry it to a length of 1 to 2 mm. The mixture was cut into 5% granules. Example 6 A 1/8850 are porcelain pot was filled with water and stirred paddy soil (alluvial loam), and after sowing paddy weeds, rice seedlings at the 3-leaf stage (variety: Akinishiki) were placed at a depth of 1 cm. They were transplanted and water was added to make them submerged to a depth of 3 cm. Next, a predetermined amount of a water diluted solution of a hydrating powder of each compound prepared according to Formulation Example 1 was dropped upon germination of weeds. After treatment, the plants were grown in a greenhouse at an average temperature of 25°C, and three weeks later, the herbicidal effects of each test compound were investigated. The results are shown in Table 2. However, the broad-leaved plants shown in the table refer to azalea, azalea, and aze pepper. In addition, the evaluation is made in 6 stages, and in the numbers in the table, 0 indicates normal, 1 to 4 indicates intermediate between normal and complete withering, and 5 indicates complete withering.
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The plants were transplanted to a depth of 1 cm and water was added to make them flooded to a depth of 3 cm. After the wildflowers had grown to the 0-leaf stage (at the time of germination), the 1.5-leaf stage, and the 3-leaf stage, they were treated with a predetermined amount of an aqueous solution of a hydrating powder of each compound prepared according to Formulation Example 1. After treatment, the plants were grown in a greenhouse at an average temperature of 25°C, and three weeks later, the herbicidal effects of each test compound were investigated. The survey results are shown in Table 3. The criteria for herbicidal effect in the table is based on Example 6.
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Various plant seeds were sown to a depth of 0.5 to 1 cm, and then a predetermined amount of a water diluted solution of a hydrating powder of each compound prepared according to Formulation Example 1 was sprayed onto the soil surface. After treatment, the plants were grown in a greenhouse at an average temperature of 25°C, and two weeks later, the herbicidal effects of each test compound were investigated. The survey results are shown in Table 4. Note that the criteria for the herbicidal effect in Table 4 are the same as in Example 6.
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Figure 1 shows 1 H- of the compound obtained in Example 2.
Figures 3, 4, and 5 are 1 H-NMR charts of the compounds obtained in Example 1, Example 3, and Example 4, respectively, and Figure 2 is the chart of Example 1. The IR chart of the compound obtained in is shown.
Claims (1)
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å¹æåãšããé€èå€ã[Claims] 1 General formula, (In the formula, R 1 and R 2 are the same or different hydrogen atoms, halogen atoms, alkyl groups, alkoxy groups,
An alkylthio group, an alkoxyalkyl group, an alkylthioalkyl group, R represents a halogen atom, an alkyl group, an alkoxy group, an alkylthio group, an alkoxyalkyl group, an alkylthioalkyl group, and R 3 , R 4 and R 5 are the same or different, respectively. represents a hydrogen atom, a halogen atom, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, or an alkylthio group, and R 6 represents a hydrogen atom or an alkyl group. However, R 1 or R 2 is a hydrogen atom,
When R and R 2 or R 1 are both the same type of halogen atom, the substitution positions of R and R 2 or R 1 are the 2nd and 4th positions, or the 4th and 5th positions of the thiophene ring. )
N-substituted-chloroacetanilide represented by 2 general formula, N-substituted aniline represented by the general formula,
A general formula characterized by reacting with chloroacetyl halide represented by ClCH 2 COX, A method for producing N-substituted chloroacetanilide. (In the formula, R 1 and R 2 are the same or different hydrogen atoms, halogen atoms, alkyl groups, alkoxy groups,
An alkylthio group, an alkoxyalkyl group, an alkylthioalkyl group, R represents a halogen atom, an alkyl group, an alkoxy group, an alkylthio group, an alkoxyalkyl group, an alkylthioalkyl group, and R 3 , R 4 and R 5 are the same or different, respectively. represents a hydrogen atom, a halogen atom, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, or an alkylthio group, and R 6 represents a hydrogen atom or an alkyl group. However, R 1 or R 2 is a hydrogen atom,
When R and R 2 or R 1 are both the same type of halogen atom, the substitution positions of R and R 2 or R 1 are the 2nd and 4th positions, or the 4th and 5th positions of the thiophene ring. ) 3 general formula, Substituted thiophene and general formula represented by, A general formula characterized by reacting with chloroacetanilide represented by A method for producing N-substituted chloroacetanilide. (In the formula, R 1 and R 2 are the same or different hydrogen atoms, halogen atoms, alkyl groups, alkoxy groups,
An alkylthio group, an alkoxyalkyl group, an alkylthioalkyl group, R represents a halogen atom, an alkyl group, an alkoxy group, an alkylthio group, an alkoxyalkyl group, an alkylthioalkyl group, and R 3 , R 4 and R 5 are the same or different, respectively. represents a hydrogen atom, a halogen atom, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, or an alkylthio group, and R 6 represents a hydrogen atom or an alkyl group. However, R 1 or R 2 is a hydrogen atom,
When R and R 2 or R 1 are both the same type of halogen atom, the substitution positions of R and R 2 or R 1 are the 2nd and 4th positions, or the 4th and 5th positions of the thiophene ring. ) 4 General formula, (In the formula, R 1 and R 2 are the same or different hydrogen atoms, halogen atoms, alkyl groups, alkoxy groups,
An alkylthio group, an alkoxyalkyl group, an alkylthioalkyl group, R represents a halogen atom, an alkyl group, an alkoxy group, an alkylthio group, an alkoxyalkyl group, an alkylthioalkyl group, and R 3 , R 4 and R 5 are the same or different, respectively. represents a hydrogen atom, a halogen atom, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, or an alkylthio group, and R 6 represents a hydrogen atom or an alkyl group. However, R 1 or R 2 is a hydrogen atom,
When R and R 2 or R 1 are both the same type of halogen atom, the substitution positions of R and R 2 or R 1 are the 2nd and 4th positions, or the 4th and 5th positions of the thiophene ring. )
A herbicide containing an N-substituted chloroacetanilide as an active ingredient.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15398684A JPS6136280A (en) | 1984-07-26 | 1984-07-26 | N-substituted-chloroacetanilide and preparation thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15398684A JPS6136280A (en) | 1984-07-26 | 1984-07-26 | N-substituted-chloroacetanilide and preparation thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6136280A JPS6136280A (en) | 1986-02-20 |
| JPH0513160B2 true JPH0513160B2 (en) | 1993-02-19 |
Family
ID=15574408
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15398684A Granted JPS6136280A (en) | 1984-07-26 | 1984-07-26 | N-substituted-chloroacetanilide and preparation thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6136280A (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59157083A (en) * | 1983-02-25 | 1984-09-06 | Tokuyama Soda Co Ltd | N-substituted-chloroacetanilide and its preparation |
-
1984
- 1984-07-26 JP JP15398684A patent/JPS6136280A/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59157083A (en) * | 1983-02-25 | 1984-09-06 | Tokuyama Soda Co Ltd | N-substituted-chloroacetanilide and its preparation |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6136280A (en) | 1986-02-20 |
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