CN101279951A - 2-pyrimindinyloxy (pyrimindinylthio) benzoxy enoates compound and application thereof - Google Patents
2-pyrimindinyloxy (pyrimindinylthio) benzoxy enoates compound and application thereof Download PDFInfo
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- CN101279951A CN101279951A CNA2007100108586A CN200710010858A CN101279951A CN 101279951 A CN101279951 A CN 101279951A CN A2007100108586 A CNA2007100108586 A CN A2007100108586A CN 200710010858 A CN200710010858 A CN 200710010858A CN 101279951 A CN101279951 A CN 101279951A
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- Prior art keywords
- compound
- alkyl
- general formula
- oxygen
- hydrogen
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 43
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 8
- 150000002367 halogens Chemical class 0.000 claims abstract description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 7
- 238000009333 weeding Methods 0.000 claims abstract description 7
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 16
- 241000196324 Embryophyta Species 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 12
- 230000002363 herbicidal effect Effects 0.000 claims description 10
- -1 ester compound Chemical class 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- 239000005711 Benzoic acid Substances 0.000 claims description 7
- XOCUXOWLYLLJLV-UHFFFAOYSA-N [O].[S] Chemical compound [O].[S] XOCUXOWLYLLJLV-UHFFFAOYSA-N 0.000 claims description 7
- 150000001336 alkenes Chemical class 0.000 claims description 7
- 235000010233 benzoic acid Nutrition 0.000 claims description 7
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 239000005864 Sulphur Chemical group 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 5
- 230000012010 growth Effects 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 230000000694 effects Effects 0.000 abstract description 9
- 244000105624 Arachis hypogaea Species 0.000 abstract description 7
- 235000010777 Arachis hypogaea Nutrition 0.000 abstract description 7
- 240000008042 Zea mays Species 0.000 abstract description 6
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 abstract description 6
- 235000002017 Zea mays subsp mays Nutrition 0.000 abstract description 6
- 125000000217 alkyl group Chemical group 0.000 abstract description 6
- 235000005822 corn Nutrition 0.000 abstract description 6
- 229920000742 Cotton Polymers 0.000 abstract description 5
- 244000068988 Glycine max Species 0.000 abstract description 5
- 235000010469 Glycine max Nutrition 0.000 abstract description 5
- 241000219146 Gossypium Species 0.000 abstract description 5
- 125000000304 alkynyl group Chemical group 0.000 abstract description 3
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 235000008692 Carum bulbocastanum Nutrition 0.000 abstract 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 abstract 1
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 11
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 7
- 235000015320 potassium carbonate Nutrition 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 235000017060 Arachis glabrata Nutrition 0.000 description 6
- 235000018262 Arachis monticola Nutrition 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 235000020232 peanut Nutrition 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 238000005406 washing Methods 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 235000017550 sodium carbonate Nutrition 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 244000025254 Cannabis sativa Species 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229930013930 alkaloid Natural products 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 3
- 229920000053 polysorbate 80 Polymers 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000008399 tap water Substances 0.000 description 3
- 235000020679 tap water Nutrition 0.000 description 3
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- 240000006995 Abutilon theophrasti Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical group ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229940126657 Compound 17 Drugs 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- 244000058871 Echinochloa crus-galli Species 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 241000209140 Triticum Species 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000012258 culturing Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 2
- 235000011167 hydrochloric acid Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229940095102 methyl benzoate Drugs 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 235000014347 soups Nutrition 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 239000003643 water by type 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
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-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
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 1
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- NXTDJHZGHOFSQG-UHFFFAOYSA-N 3-phenoxybenzoic acid Chemical compound OC(=O)C1=CC=CC(OC=2C=CC=CC=2)=C1 NXTDJHZGHOFSQG-UHFFFAOYSA-N 0.000 description 1
- ITDVJJVNAASTRS-UHFFFAOYSA-N 4,6-dimethoxy-2-methylsulfonylpyrimidine Chemical compound COC1=CC(OC)=NC(S(C)(=O)=O)=N1 ITDVJJVNAASTRS-UHFFFAOYSA-N 0.000 description 1
- DMAYBPBPEUFIHJ-UHFFFAOYSA-N 4-bromobut-1-ene Chemical compound BrCCC=C DMAYBPBPEUFIHJ-UHFFFAOYSA-N 0.000 description 1
- WOXUTGMNLPVONH-SNAWJCMRSA-N C/C=C/COC(=O)C1=C(C=CC=C1Cl)SC2=NC(=CC(=N2)OC)OC Chemical compound C/C=C/COC(=O)C1=C(C=CC=C1Cl)SC2=NC(=CC(=N2)OC)OC WOXUTGMNLPVONH-SNAWJCMRSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 240000001238 Gaultheria procumbens Species 0.000 description 1
- 235000007297 Gaultheria procumbens Nutrition 0.000 description 1
- 244000020551 Helianthus annuus Species 0.000 description 1
- 235000003222 Helianthus annuus Nutrition 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125797 compound 12 Drugs 0.000 description 1
- 229940126543 compound 14 Drugs 0.000 description 1
- 229940125758 compound 15 Drugs 0.000 description 1
- 229940126142 compound 16 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 208000006278 hypochromic anemia Diseases 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
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Abstract
The invention discloses 2-pyridine-oxyl(sulfide) benzoyloxy enoates compound with general formula(I, II); wherein X is H or S; R1 is H, halogen, or 4,6- dimethoxy pyrimidine-2- radicel or one of the following groups; methyls on N-O bonds and double bonds are in maleinoid form or anti form; R2,R3,R4,R6,R7 are selected from H or alkyl from C1-C6; R5 is alkyl from C1-C6, alcoxyl-alkyl from C2-C6, alkenyl from C3-C6 or alkynyl from C3-C6; radicals of R6 and R7 are in maleinoid form or anti form; R8 is alkyl from C1-C6, alkenyl from C3-C6 or alkynyl from C3-C6. The compound (I, II)is of activity in weeding and is safe to crops like soybean, cotton, earthnut, cole, corn, etc.
Description
Technical field
The invention belongs to the weedicide field, be specifically related to a kind of 2-pyrimidine oxygen (sulphur) yl benzoic acid base olefin(e) acid ester compound and application thereof.
Background technology
Because the succession of weeds population, transition and to the drug-fast generation of chemical pesticide with develop rapidly; people are to the continuous reinforcement of ecological environmental protection consciousness, to chemical pesticide pollute, agricultural chemicals to the understanding of non-target organism influence and in the agricultural chemicals ecotope attention of home to return to problem improve constantly.Along with the continuous growth of the reducing gradually of world's cultivated area, population and to the increase of grain demand amount, force people to develop agriculture production technology rapidly, improve and improve cropping system, and need constantly invention novel with improved herbicidal compound and composition.
EP223406 has reported that some 2-pyrimidine oxygen (sulphur) yl benzoic acid ester compound has weeding activity, and to peanut, Sunflower Receptacle safety.CN1749236A and CN1927811A disclose some 3-phenoxy benzoic acid base olefin(e) acid ester compound and have had weeding activity.Do not relate to preparation and application thereof in the prior art as 2-pyrimidine oxygen (sulphur) yl benzoic acid base olefin(e) acid ester compound shown in the present.
Summary of the invention
The purpose of this invention is to provide a kind of novel structure, have fine weeding activity and be the herbicidal composition of active ingredient, to satisfy the needs that agriculture production develops rapidly to 2-pyrimidine oxygen (sulphur) the yl benzoic acid base olefin(e) acid ester compound of crop safety and with this compounds.
Technical scheme of the present invention is as follows:
The invention provides a kind of 2-pyrimidine oxygen (sulphur) yl benzoic acid base olefin(e) acid ester compound of novel structure, as general formula (I, II) shown in:
In the formula:
X is selected from oxygen or sulphur;
R
1Be selected from hydrogen, halogen, 4,6-dimethoxypyridin-2-base or following radicals:
Wherein, the methyl on nitrogen-oxygen bond and the two keys is a cis or trans;
R
2, R
3, R
4, R
6, R
7Be selected from hydrogen or C respectively
1-C
6Alkyl;
R
5Be selected from C
1-C
6Alkyl, C
2-C
6Alkoxyalkyl, C
3-C
6Thiazolinyl or C
3-C
6Alkynyl;
R
6With R
7Group is a cis or trans;
R
8Be selected from C
1-C
6Alkyl, C
3-C
6Thiazolinyl or C
3-C
6Alkynyl.
Comparatively preferred compound is among the present invention, general formula (I, II) in:
X is selected from oxygen or sulphur;
R
1Be selected from hydrogen, halogen, 4,6-dimethoxypyridin-2-base or following radicals:
Wherein, the methyl on nitrogen-oxygen bond and the two keys is a cis;
R
2, R
3, R
4, R
6, R
7Be selected from hydrogen respectively; R
6With R
7Group is trans;
R
5Be selected from C
1-C
6Alkyl, C
3-C
6Thiazolinyl or C
3-C
6Alkynyl;
R
8Be selected from methyl.
Further preferred compound is among the present invention, general formula (I, II) in:
X is selected from oxygen or sulphur;
R
1Be selected from hydrogen or halogen;
R
2, R
3, R
4, R
6, R
7Be selected from hydrogen respectively; R
6With R
7Group is trans;
R
5Be selected from C
1-C
6Alkyl, C
3-C
6Thiazolinyl or C
3-C
6Alkynyl.
(I, II) alkyl of middle indication comprises the straight or branched alkyl to general formula.Alkoxyalkyl is meant the straight or branched form, contains the alkyl of alkoxy grp, for example methoxyl methyl, the different third oxygen ethyl etc.Thiazolinyl is meant the straight or branched form, and the group of 1 to 2 carbon-carbon double bond is arranged, for example, and propenyl, allyl group etc.Alkynyl is meant the straight or branched form, and 1 to 2 carbon carbon triple-linked group is arranged, for example, and proyl, propargyl etc.Halogen comprises fluorine, chlorine, bromine, iodine.
General formula of the present invention (I, II) compound can be prepared by following method:
(III) (has commercially available with compound, also can make by oneself, the preparation method is referring to Pestic.Sci.1996,47,115-124) be dissolved in the The suitable solvent, made compound (V) for-10 ℃ in 0.5-48 hour to reaction between the boiling point in temperature with compound (IV) (preparation method is referring to J.Org.Chem.32:3229 (1967)).The suitable solvent can be selected from for example toluene, acetone, DMF, THF or dioxane etc.Add alkaloids, as triethylamine, pyridine, sodium hydroxide, potassium hydroxide, yellow soda ash, salt of wormwood etc. to reacting favourable.
Compound (V) and suitable alkali are joined in the mixed solvent that suitable organic solvent and water forms, temperature be-10 ℃ to reacting 0.5-48 hour between the boiling point, reaction solution is through hydrochloric acid or sulfuric acid acidation, making intermediate acid is compound (VI).Suitable organic solvent is selected from chloroform, methylene dichloride, tetracol phenixin, normal hexane, benzene, toluene, ethyl acetate, methyl alcohol, ethanol, THF or dioxane etc.; Suitable alkali is selected from sodium hydroxide, potassium hydroxide, yellow soda ash or salt of wormwood etc.
(preparation method of VII is referring to synthetic chemistry with compound (VII) for compound (VI), 13 (3), 315-316, (2005)) be dissolved in The suitable solvent for example toluene, acetone, DMF, THF or dioxane etc., temperature be-10 ℃ between the boiling point reaction 0.5-48 hour, make compound (I).Add alkaloids such as triethylamine, pyridine, sodium hydroxide, potassium hydroxide, yellow soda ash, salt of wormwood etc. to reacting favourable.In the compound (VII), Y can be chlorine, bromine or iodine.
Because the difference of starting raw material or reaction conditions can obtain R
6With R
7Group is cis or trans compound (VIII), or contains the cis of different ratios and the mixture (preparation of VIII is referring to CN1927811A) of trans-compound (VIII) simultaneously.In the compound (VIII), Y can be chlorine, bromine or iodine.
Compound (VI) and compound (VIII) are dissolved in The suitable solvent for example toluene, acetone, DMF, THF or dioxane etc., temperature be-10 ℃ to reacting 0.5-48 hour between the boiling point, make R
6With R
7Group is cis or trans compound (II), or contains the cis of different ratios and the mixture of trans-compound (II) simultaneously.Add alkaloids such as triethylamine, pyridine, sodium hydroxide, potassium hydroxide, yellow soda ash or salt of wormwood etc. to reacting favourable.
Table 1: the The compounds of this invention of part shown in general formula (I)
Table 2: the The compounds of this invention of part shown in general formula (II)
Part of compounds
1H NMR (CDCl
3, 300MHz) δ (ppm) data are as follows:
Compound 1
3.807(s，9H，CH
3)，4.857(s，2H，CH
2)，5.736(s，1H)，5.857(s，1H，＝CH)，6.332(s，1H，＝CH)，7.328(m，2H，Ar-H)，7.569(m，1H，Ar-H)，8.040(q，1H，J＝1.8Hz，Ar-H).
Compound 2
0.947(t，3H，J＝7.3Hz，CH
3)，1.693(m，2H，CH
2)，3.804(s，6H，OCH
3)，4.110(t，2H，J＝6.6Hz，CH
2)，4.867(s，2H，CH
2)，5.736(s，1H)，5.834(d，1H，J＝1.2Hz，＝CH)，6.331(d，1H，J＝0.9Hz，＝CH)，7.352(m，2H，Ar-H)，7.594(m，1H，Ar-H)，8.040(q，1H，J＝1.8Hz，Ar-H).
Compound 3
2.492(t，1H，J＝2.4Hz，1H)，3.784(s，6H，OCH
3)，4.765(s，2H，CH
2)，4.878(s，2H，CH
2)，5.740(s，1H)，5.929(d，1H，J＝0.9Hz，＝CH)，6.402(d，1H，J＝0.9Hz，＝CH)，7.327(m，2H，Ar-H)，7.601(m，1H，Ar-H)，8.044(q，1H，J＝1.8Hz，Ar-H).
Compound 4
1.287(t，3H，J＝7.1Hz，CH
3)，3.780(s，6H，OCH
3)，4.219(q，2H，J＝7.2Hz，CH
2)，4.866(s，2H，CH
2)，5.732(s，1H)，5.831(s，1H，＝CH)，6.321(s，1H，＝CH)，7.324(m，2H，Ar-H)，7.590(m，1H，Ar-H)，8.039(q，1H，J＝1.2Hz，Ar-H).
Compound 5
1.305(t，3H，J＝7.1Hz，CH
3)，3.711(s，6H，OCH
3)，4.222(q，2H，J＝7.2Hz，CH
2)，5.045(s，2H，CH
2)，5.709(s，1H)，5,860(s，1H，＝CH)，6.339(s，1H，＝CH)，7.448(m，2H，Ar-H)，7.631(d，1H，Ar-H).
Compound 12
3.761(s，3H，CO
2CH
3)，3.788(s，6H，OCH
3)，4.786(q，2H，CH
2)，5.739(s，1H)，6.020(m，1H，＝CH)，6.840(m，1H，CH＝)，7.340(m，2H，Ar-H)，7.616(m，1H，Ar-H)，8.162(m，1H，Ar-H).
Compound 13
1.272(t，3H，CH
3)，3.789(s，6H，OCH
3)，4.189(q，2H，CH
2)，4.786(q，2H，CH
2)，5.740(s，1H)，6.006(m，1H，＝CH)，6.856(m，1H，CH＝)，7.282(m，2H，Ar-H)，7.616(m，1H，Ar-H)，8.031(m，1H，Ar-H).
Compound 14
0.970(m，3H，CH
3)，1.407(m，2H，CH
2)，1.659(m，2H，CH
2)，3.789(s，6H，CH
3)，4.191(m，2H，CH
2)，4.785(q，2H，CH
2)，5.739(s，1H)，6.014(m，1H，＝CH)，6.804(m，1H，CH＝)，7.342(m，2H，Ar-H)，7.618(m，1H，Ar-H)，8.052(m，1H，Ar-H).
Compound 15
0.960(m，3H，CH
3)，1.678(m，2H，CH
2)，3.790(s，6H，OCH
3)，4.112(m，2H，CH
2)，4.789(q，2H，CH
2)，5.746(s，1H)，6.014(m，1H，＝CH)，6.810(m，1H，CH＝)，7.260(m，1H，Ar-H)，7.369(m，1H，Ar-H)，7.613(m，1H，Ar-H)，8.053(m，1H，Ar-H).
Compound 16 is the mixture of two kinds of configurations, wherein contain cis 33% (among the general formula I I, R
6With R
7Group is at two key homonymies);
Contain trans 67% (among the general formula I I, R
6With R
7Group is not at two key homonymies).
Cis: 1.271 (m, 3H, CH
3), 1.872 (s, 3H, CH
3), 3.800 (s, 6H, OCH
3), 4.172 (q, 2H, J=6.9Hz, CH
2), 5.266 (s, 2H, CH
2), 5.735 (s, 1H ,=CH), 5.788 (s, 1H), 7.325 (m, 2H, Ar-H), 7.617 (m, 1H, Ar-H), 8.059 (m, 1H, Ar-H).
Trans: 1.271 (m, 3H, CH
3), 2.105 (s, 3H, CH
3), 3.800 (s, 6H, OCH
3), 4.172 (q, 2H, J=6.9Hz, CH
2), 4.615 (s, 2H, CH
2), 5.735 (s, 1H ,=CH), 5.788 (s, 1H), 7.325 (m, 2H, Ar-H), 7.617 (m, 1H, Ar-H), 8.059 (m, 1H, Ar-H).
Compound 17
1.285(t，3H，CH
3)，3.720(s，6H，OCH
3)，4.199(q，2H，CH
2)，4.955(m，2H，CH
2)，5.717(s，1H)，6.012(m，1H，＝CH)，6.918(m，1H，CH＝)，7.469(m，2H，Ar-H)，7.635(d，1H，Ar-H).
(I, II) compound has weeding activity to general formula of the present invention.Compare with disclosed compound in the prior art, compound of the present invention uses before than seedling under the low dosage, behind the seedling can effectively control single broadleaf weed, especially gramineous weeds is had the higher activity of preventing and kill off.Therefore technical scheme of the present invention comprises that (I, II) compound is used to control the purposes of weeds to general formula.
General formula of the present invention (I, II) compound uses before seedling, to soybean, cotton, peanut and other crops safety; Behind seedling, use,, especially the security of gramineous crop corn is had and make us unexpected promising result, kept simultaneously the height of gramineous weeds barnyard grass grass is prevented and kill off activity crop safeties such as corn, peanut, rapes.
The present invention comprises that also (I, II) compound is as the herbicidal composition of active ingredient with general formula.The weight percentage of active ingredient is 5-90% in this herbicidal composition.Comprise also in this herbicidal composition that agricultural goes up acceptable carrier.
Herbicidal composition of the present invention can several formulations form use.Usually with compound dissolution of the present invention or be scattered in and be mixed with preparation in the carrier so that be easier to disperse when using as weedicide.For example: these chemicals can be made into wettable powder or missible oil.Therefore, in these compositions, add a kind of liquid or solid carrier at least, and need to add suitable tensio-active agent usually.
Other embodiments of the present invention are method of controlling weeds, and this method comprises herbicidal composition of the present invention is imposed on the surface of the place of described weeds or described weed growth or its growth medium.Usually the comparatively suitable significant quantity of selecting is that per hectare 10 restrains 5000 grams, and preferred significant quantity is that per hectare 20 restrains 2500 grams.Use for some, can in herbicidal composition of the present invention, add one or more other weedicide, can produce additional advantage and effect thus.
Compound of the present invention both can use separately also can be mixed together use with other known sterilant, sterilant, plant-growth regulator or fertilizer etc.
Should be clear and definite be in claim of the present invention institute restricted portion, can carry out various conversion and change.
Embodiment
The following example and living test are tested the result and be can be used to further specify the present invention, but do not mean that restriction the present invention.Synthetic example
Synthesizing of compound 4:
1.
In 250 milliliters of round-bottomed flasks, add 4,6-dimethoxy-2-methanesulfonyl pyrimidine 7 grams (0.036 mole), 6 milliliters of wintergreen oils (0.047 mole), salt of wormwood 6 grams (0.043 mole), N, 100 milliliters of dinethylformamides.After 4 hours, be cooled to room temperature in 110-130 ℃ of stirring reaction.In reaction solution, add 180 milliliters in 200 milliliters of ethyl acetate and water, extraction.Organic phase is used 50 milliliters in 1% dilute hydrochloric acid, 50 milliliters of saturated sodium bicarbonates, 3 * 50 milliliters of saturated sodium-chloride water solution washings successively, anhydrous magnesium sulfate drying, the resistates that obtains behind the precipitation is through silica gel column chromatography (petrol ether/ethyl acetate=5/1) purifying, obtain 2-(4,6-dimethoxy-2-2-pyrimidinyl oxy) methyl benzoate 8.35 grams.
2.
In 150 milliliters of round-bottomed flasks, add 2-(4 successively, 6-dimethoxy-2-2-pyrimidinyl oxy) methyl benzoate 2.93 gram (0.01 mole), 50 milliliters of tetrahydrofuran (THF)s, sodium hydroxide 0.4 gram (0.01 mole) are dissolved in the solution of 50 ml waters, and the stirring at normal temperature reaction is spent the night.The back decompression that reacts completely steams tetrahydrofuran (THF).In resistates, add 2 milliliters of 200 milliliters of ethyl acetate, concentrated hydrochloric acids, 50 milliliters of washings, 3 * 50 milliliters of saturated sodium-chloride water solution washing organic phases, anhydrous magnesium sulfate drying gets 2-(4,6-dimethoxy-2-2-pyrimidinyl oxy) phenylformic acid 2.05 grams behind the precipitation.
3.
In 100 milliliters of three mouthfuls of round-bottomed flasks, add 2-(4 successively, 6-dimethoxy-2-2-pyrimidinyl oxy) phenylformic acid 1.0 gram (3.6 mmole), N, 30 milliliters of dinethylformamides, salt of wormwood 0.50 gram (3.6 mmole), 2-brooethyl ethyl propenoate 0.69 gram (3.6 mmole).In 40-60 ℃ of stirring reaction after 8 hours, in reaction solution, add 180 milliliters in 200 milliliters of ethyl acetate and water, extraction, saturated sodium-chloride water solution washing organic phase with 180 milliliters, use anhydrous magnesium sulfate drying again, the resistates that obtains behind the precipitation obtains 2-(ethoxycarbonyl) allyl group-2-(4,6-dimethoxy-2-2-pyrimidinyl oxy) benzoic ether 1.05 grams through silica gel column chromatography (petrol ether/ethyl acetate=3/1) purifying.
Synthesizing of compound 17:
In 100 milliliters of three mouthfuls of round-bottomed flasks, add 6-chloro-2-(4 successively, 6-dimethoxy-2-pyrimidine sulfenyl) phenylformic acid 0.32 gram (0.9 mmole), N, 10 milliliters of dinethylformamides, salt of wormwood 0.17 gram (1.2 mmole), trans 4-bromobutene acetoacetic ester 0.34 gram (1.5 mmole).In 80 ℃ of stirring reactions after 4 hours, in reaction solution, add 180 milliliters in 200 milliliters of ethyl acetate and water, extraction, saturated sodium-chloride water solution washing organic phase with 200 milliliters, use anhydrous magnesium sulfate drying again, the resistates that obtains behind the precipitation obtains 4-(6-chloro-2-(4,6-dimethoxy-2-pyrimidine sulfenyl) benzoyloxy) trans-2-butene acetoacetic ester 0.28 gram through silica gel column chromatography (petrol ether/ethyl acetate=3/1) purifying.
Other compounds in table 1 and the table 2 can make by above similar method.
Give birth to and survey example
Behind the former medicinal acetone solution, leave standstill the liquid to be measured of tap water preparation desired concn with 1 ‰ tween 80 by test requirements document.Processing (spray pressure 1.95kg/cm sprays with track type crop spraying machine (Britain Engineer Research Ltd. designs production)
2, spouting liquid 50ml/m
2, crawler belt speed 30cm/s, nozzle are fan nozzle).
Test before the seedling: it is 100cm that quantitative weeds (piemarker, barnyard grass grass, Herba Setariae Viridis) and crop (paddy rice, wheat, corn, cotton, peanut, soybean) seed are sowed at sectional area respectively
2Culturing pot in, broadcast back earthing 1cm, test compound sparges soil surface, handles and is placed on the greenhouse, waters then, the tween 80 with 1 ‰ leaves standstill tap water to be handled in contrast.
Test behind the seedling: it is 100cm that quantitative weeds (piemarker, barnyard grass grass, Herba Setariae Viridis) and crop (corn, cotton, peanut, rape, soybean) seed are sowed at sectional area respectively
2Culturing pot in, broadcast back earthing 1cm, cultivate according to a conventional method in the greenhouse.Treat that weeds grew to for 1.5 leaf phases, paddy rice, wheat, corn, cotton, peanut, rape and soybean 2-3 leaf phase, the examination material of choosing the growth uniformity carries out behind the seedling cauline leaf spraying to be handled, and the tween 80 with 1 ‰ leaves standstill tap water to be handled in contrast.Be placed on dry ventilation after the examination material is handled, treat the soup natural air drying after, place management according to a conventional method in the greenhouse, handle the method that employing is poured water from the bottom in back 48 hours, avoid soup to be washed away.
Handle the back and 4 weeks estimated investigation, inhibiting rate is various degree of injury compared with the control, comprise kill, chlorosis, withered spot, distortion, deformity, growth-inhibiting or blade calcination etc.Partial test the results are shown in Table 3,4.
Table 3: the part general formula (I, II) weeding activity of compound (before the seedling/seedling after, inhibiting rate %)
Table 4: the part general formula (I, II) compound to the security of crop (before the seedling/seedling after, inhibiting rate %)
Annotate *: in table 3 and the table 4, "-" expression is not surveyed.
Claims (6)
1. 2-pyrimidine oxygen (sulphur) yl benzoic acid base olefin(e) acid ester compound, as general formula (I, II) shown in:
In the formula:
X is selected from oxygen or sulphur;
R
1Be selected from hydrogen, halogen, 4,6-dimethoxypyridin-2-base or following groups:
Wherein, the methyl on nitrogen-oxygen bond and the two keys is a cis or trans;
R
2, R
3, R
4, R
6, R
7Be selected from hydrogen or C respectively
1-C
6Alkyl;
R
5Be selected from C
1-C
6Alkyl, C
2-C
6Alkoxyalkyl, C
3-C
6Thiazolinyl or C
3-C
6Alkynyl;
R
6With R
7Group is a cis or trans;
R
8Be selected from C
1-C
6Alkyl, C
3-C
6Thiazolinyl or C
3-C
6Alkynyl.
2. according to the described compound of claim 1, it is characterized in that, general formula (I, II) in:
X is selected from oxygen or sulphur;
R
1Be selected from hydrogen, halogen, 4,6-dimethoxypyridin-2-base or following radicals:
Wherein, the methyl on nitrogen-oxygen bond and the two keys is a cis;
R
2, R
3, R
4, R
6, R
7Be selected from hydrogen respectively; R
6With R
7Group is trans;
R
5Be selected from C
1-C
6Alkyl, C
3-C
6Thiazolinyl or C
3-C
6Alkynyl;
R
8Be selected from methyl.
3. according to the described compound of claim 2, it is characterized in that, general formula (I, II) in:
X is selected from oxygen or sulphur;
R
1Be selected from hydrogen or halogen;
R
2, R
3, R
4, R
6, R
7Be selected from hydrogen respectively; R
6With R
7Group is trans;
R
5Be selected from C
1-C
6Alkyl, C
3-C
6Thiazolinyl or C
3-C
6Alkynyl.
4. (I, II) compound is used to control the purposes of weeds to the described general formula of claim 1.
5. herbicidal composition, contain the general formula as active ingredient as claimed in claim 1 (I, II) compound and agricultural go up acceptable carrier, the weight percentage of active ingredient is 5-90% in the composition.
6. a control method for weed is characterized in that: the herbicidal composition as claimed in claim 5 of using the weeding effective dose on the growth mediums of weeds or weeds or place.
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