CN106632005A - Ethyl pyridyloxyphenoxypropionate compound as well as preparation method and application thereof - Google Patents
Ethyl pyridyloxyphenoxypropionate compound as well as preparation method and application thereof Download PDFInfo
- Publication number
- CN106632005A CN106632005A CN201611072268.1A CN201611072268A CN106632005A CN 106632005 A CN106632005 A CN 106632005A CN 201611072268 A CN201611072268 A CN 201611072268A CN 106632005 A CN106632005 A CN 106632005A
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- Prior art keywords
- compound
- reaction
- preparation
- acid
- pharmaceutically acceptable
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- 238000002360 preparation method Methods 0.000 title claims abstract description 16
- -1 Ethyl pyridyloxyphenoxypropionate compound Chemical class 0.000 title abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 47
- 241000196324 Embryophyta Species 0.000 claims abstract description 16
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 238000009333 weeding Methods 0.000 claims abstract description 7
- 238000006243 chemical reaction Methods 0.000 claims description 32
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
- 230000002363 herbicidal effect Effects 0.000 claims description 15
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 claims description 14
- 150000001263 acyl chlorides Chemical class 0.000 claims description 12
- 229940126062 Compound A Drugs 0.000 claims description 10
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims description 10
- 239000012752 auxiliary agent Substances 0.000 claims description 8
- 239000003153 chemical reaction reagent Substances 0.000 claims description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical group ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 6
- VOGSDFLJZPNWHY-UHFFFAOYSA-N 2,2-difluoroethanol Chemical compound OCC(F)F VOGSDFLJZPNWHY-UHFFFAOYSA-N 0.000 claims description 5
- 230000032050 esterification Effects 0.000 claims description 5
- 238000005886 esterification reaction Methods 0.000 claims description 5
- 238000006266 etherification reaction Methods 0.000 claims description 5
- 238000003786 synthesis reaction Methods 0.000 claims description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical class ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 4
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 claims description 4
- 239000003905 agrochemical Substances 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 2
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical group [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 2
- 238000003408 phase transfer catalysis Methods 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- 241000209140 Triticum Species 0.000 abstract description 9
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- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 24
- 239000000203 mixture Substances 0.000 description 23
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 22
- 150000002148 esters Chemical class 0.000 description 13
- 238000000034 method Methods 0.000 description 13
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 11
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- 239000002253 acid Substances 0.000 description 10
- 239000004009 herbicide Substances 0.000 description 10
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 10
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
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- JBDHZKLJNAIJNC-LLVKDONJSA-N clodinafop-propargyl Chemical group C1=CC(O[C@H](C)C(=O)OCC#C)=CC=C1OC1=NC=C(Cl)C=C1F JBDHZKLJNAIJNC-LLVKDONJSA-N 0.000 description 8
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- 231100000572 poisoning Toxicity 0.000 description 5
- 230000000607 poisoning effect Effects 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
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- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229920000151 polyglycol Polymers 0.000 description 4
- 239000010695 polyglycol Substances 0.000 description 4
- 230000003449 preventive effect Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000005995 Aluminium silicate Substances 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
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- 239000007859 condensation product Substances 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
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- 241000209082 Lolium Species 0.000 description 1
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- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
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- 125000004432 carbon atom Chemical group C* 0.000 description 1
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- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
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- 239000002270 dispersing agent Substances 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 239000010459 dolomite Substances 0.000 description 1
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- 239000003937 drug carrier Substances 0.000 description 1
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- 150000002170 ethers Chemical class 0.000 description 1
- 238000007046 ethoxylation reaction Methods 0.000 description 1
- PQKBPHSEKWERTG-LLVKDONJSA-N ethyl (2r)-2-[4-[(6-chloro-1,3-benzoxazol-2-yl)oxy]phenoxy]propanoate Chemical group C1=CC(O[C@H](C)C(=O)OCC)=CC=C1OC1=NC2=CC=C(Cl)C=C2O1 PQKBPHSEKWERTG-LLVKDONJSA-N 0.000 description 1
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- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
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- 239000000174 gluconic acid Substances 0.000 description 1
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- 235000013922 glutamic acid Nutrition 0.000 description 1
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- 229910052622 kaolinite Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229960000448 lactic acid Drugs 0.000 description 1
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- 231100000053 low toxicity Toxicity 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
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- 229910017604 nitric acid Inorganic materials 0.000 description 1
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- 239000002420 orchard Substances 0.000 description 1
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- ILUJQPXNXACGAN-UHFFFAOYSA-N ortho-methoxybenzoic acid Natural products COC1=CC=CC=C1C(O)=O ILUJQPXNXACGAN-UHFFFAOYSA-N 0.000 description 1
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- 239000012188 paraffin wax Substances 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 229940044654 phenolsulfonic acid Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N phthalic anhydride Chemical compound C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
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- SFLJXXFBYIUQCS-UHFFFAOYSA-N prop-1-ynyl propanoate Chemical compound CCC(=O)OC#CC SFLJXXFBYIUQCS-UHFFFAOYSA-N 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical class CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 229960000948 quinine Drugs 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 229960005137 succinic acid Drugs 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- DPJRMOMPQZCRJU-UHFFFAOYSA-M thiamine hydrochloride Chemical compound Cl.[Cl-].CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N DPJRMOMPQZCRJU-UHFFFAOYSA-M 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
- C07D213/643—2-Phenoxypyridines; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
Abstract
The invention discloses an ethyl pyridyloxyphenoxypropionate compound as well as a preparation method and application thereof. The compound is a compound with a structure shown as a formula (1) or pharmaceutically acceptable salt thereof. The compound or the pharmaceutically acceptable salt thereof, disclosed by the invention, can be applied to the aspect of crop weeding, and is especially applied to the aspect of preventing and removing grassy weeds. The compound disclosed by the invention does not have any bad influence on normal growth of wheat crops; a safety agent is not needed and the utilization dosage is small; the weeding spectrum is wide and the weeding effect is good; and the ethyl pyridyloxyphenoxypropionate compound is more easily used in agricultural production. (The formula (1) is shown in the description.).
Description
Technical field
The invention belongs to pesticide field, and in particular to a kind of pyridine epoxide phenoxy propionic acid ethyl ester compound and its preparation side
Method and purposes.
Background technology
Herbicide (herbicide) is referred to can make weeds that withered medicament thoroughly or selectively occurs, also known as herbicide,
To the class material for eliminating or suppressing plant growth.World Herbicide development is gradually steady, main development efficiently, it is low toxicity, wide
Spectrum, the kind of low consumption, the little disposable treatment agent of environmental pollution is increasingly becoming main flow.Conventional kind is organic compound
Thing, can be widely used for preventing and treating the ground such as farmland, orchard, floral nursery, grassland and bare place, railway line, river course, reservoir, warehouse miscellaneous
The noxious plants such as grass, miscellaneous filling, miscellaneous tree.At present conventional cereal field gramineous weed weedicide has fenoxapropPethyl, clodinafop-propargyl
Deng.
Clodinafop-propargyl (Clodinafop-propargyl), also known as wheat pole, chemical name：(R) -2- [4- (the fluoro- 2- pyrroles of the chloro- 3- of 5-
Pyridine epoxide) phenoxy group] propionic acid propynyl ester, belong to fragrant phenoxy phenoxy propionic acid herbicide, can effectively suppress the biosynthesis of class ester, be
The auxiliary quick A hydroxylase inhibitors of acetyl, are selective inner sucting conduction type after seedling cauline leaf process agent.Medicament is inhaled by plant leaf blade, leaf sheath
Separate living tissue is conducted after receipts, suppresses acetyl-CoA carboxylase, so as to suppress fatty acid biological to synthesize, ultimately result in weeds dead.
Inactive metabolin is resolved in resistance crop body.This product is degraded to free acid phenyl quickly in soil and pyridine moiety enters
Enter soil.Additionally, clodinafop-propargyl has a certain degree of poisoning, the farmings such as wheat use can be killed at low temperature, therefore clodinafop-propargyl makes
Must be mixed with safener with during, wherein clodinafop-propargyl and safener-cloquintocetmexyl or cloquitocet_mexyl etc. are with 4：1 mixing is supporting to be made
With, wheat paddock weeding is applied to, wheat paddock rat-tail amur foxtail, tall oat grass, rye grass, rough stalked blue grass, green bristlegrass etc. can be prevented and treated
Grassy weed.But, clodinafop-propargyl is invalid to broad leaved weed, and herbicidal spectrum is narrow so as to be restricted using on.
Existing herbicide dosage is big, for a long time using being also easy to produce the resistance to the action of a drug, and easily produces residues of pesticides；Part
Herbicide has poisoning, needs to use safener or other auxiliary materials, is unfavorable for a large amount of Long-Time Services of herbicide, it is therefore necessary to enter
The more excellent herbicide of one step research and development effect.
The content of the invention
The purpose of the present invention is on the basis of existing technology, there is provided a kind of structure it is novel with crops herbicide effect
Pyridine epoxide phenoxy propionic acid ethyl ester compound.
It is a further object of the present invention to provide a kind of preparation method of above-claimed cpd.
Third object of the present invention is to provide a kind of purposes of above-claimed cpd in terms of crops weeding.
The purpose of the present invention can be reached by following measures：
The compound or its pharmaceutically acceptable salt of structure shown in formula (1),
Structural compounds is entitled shown in formula (1)：(R) -2- [4- (the fluoro- 2- pyridines epoxides of the chloro- 3- of 5-) phenoxy group] third
Sour (2,2 '-two fluoro ethyl) ester.
The preparation method of the compound of structure shown in a kind of formula (1)：Compound A and B carries out etherification reaction and obtains compound
C, then acyl chlorides synthetic reaction synthesis compound D is carried out, esterification formula (1) compound is finally carried out,
In a kind of preferred version, the compound preparation side of structure comprises the steps shown in formula (1)：
Step A：Etherification reaction, compound A and compound B adds in the basic conditions catalyst to carry out reaction and obtains chemical combination
Thing C；
Step B：Acyl chlorides synthetic reaction, compound C carries out reaction and obtains acyl chlorides with acylating reagent；
Step C：Esterification, compound D and 2,2- difluoroethanol carry out at low temperature reaction and obtain formula (1) compound.
Each step is described in further details below：
Step A：Etherification reaction, the synthesis of compound C；Compound A and compound B adds in the basic conditions catalyst to enter
Row reaction obtains compound C.
The mol ratio of compound A and compound B can be 1:1～1:1.5, preferably 1:1.1；Alkali can be：Sodium carbonate,
Potassium carbonate, sodium acid carbonate；Catalyst is phase transfer catalyst, can be TBAB, tetrabutylammonium chloride, the second of benzyl three
Ammonium chloride；Reaction dissolvent can be DMF, 1,2- dichloroethanes, toluene；Reaction temperature can be 55～110 DEG C, preferably 70
～75 DEG C.
Step B：Acyl chlorides synthesizes, the synthesis of compound D；Compound C carries out reaction and obtains acyl chlorides with acylating reagent.
Compound C can be 1 with the molar ratio of acylating reagent:1～1:1.5, preferably 1:1.2；Acylating reagent can be with
It is：Thionyl chloride, oxalyl chloride.Reaction dissolvent can be dichloromethane, 1,2- dichloroethanes, toluene；Reaction temperature can be 40
～80 DEG C, preferably at 60～65 DEG C.
Step C：Esterification, (R) -2- [4- (the fluoro- 2- pyridines epoxides of the chloro- 3- of 5-) phenoxy group] propionic acid (2,2 '-difluoro second
Base) ester synthesis；
Compound D carries out at low temperature reaction and obtains (R) -2- [4- (fluoro- 2- pyridines oxygen of the chloro- 3- of 5- with 2,2- difluoroethanols
Base) phenoxy group] propionic acid (2,2 '-two fluoro ethyl) ester.Compound D can be 1 with the molar ratio of 2,2- difluoroethanols:1～1:
3, preferably 1:2；Reaction temperature can be -5 DEG C～15 DEG C, preferably 0～5 DEG C.
The present invention includes a kind of Herbicidal combinations, and it is with the compound of structure shown in formula (1) or its is pharmaceutically acceptable
Salt is active component or main active, is aided with acceptable auxiliary agent on agricultural chemicals.
The composition of the present invention can jointly make acceptable formulation on agricultural chemicals by active ingredient and insecticides adjuvant.
The mass content of active ingredient can be 2～95%, preferably 5～80% in the composition of the present invention.
Suitable auxiliary agent can be solid or liquid, and they are typically the material commonly used during formulation, such as day
Right or regeneration mineral matter, solvent, dispersant, wetting agent, adhesive, thickener, adhesive or fertilizer.
The application process of the present composition includes the composition of the present invention is used for the aerial part of plant growth, especially
It is leaf portion or blade face.The frequency and amount of application of administration depends on the biology and weather life condition of pathogen.Can be by plant
Growth place, such as rice field is soaked with the liquid preparation of composition, or composition is applied in solid form in soil,
As in granular form (soil application), composition can be entered in plant body (systemic action) by soil Jing plant roots.
These compositions can only include active component (also known as active ingredient) and be administered, it is also possible to additive or
Auxiliary agent is mixed together, therefore the composition of the present invention can be prepared into various formulations, for example wettable powder, suspending agent,
Dispersible oil-suspending agent, aqueous emulsion, missible oil, water dispersible granules etc..Property and administration composition institute according to these compositions
The purpose to be reached and ambient conditions, can select by composition to spray, atomizing, dust, broadcast sowing or sprinkle the side poured or the like
Method is applied.
Can with known method can by the present invention composition be prepared into various formulations, such as can by active ingredient with help
Agent, such as solvent, solid carrier, can uniformly mix together with surfactant when needing, grind, and be prepared into required agent
Type.
Above-mentioned solvent may be selected from aromatic hydrocarbon, preferably containing 8-12 carbon atom, such as xylene mixture or substituted benzene, and phthalein
Esters of gallic acid, such as Dibutyl phthalate or phthalandione two is sad, fat hydrocarbon, such as thiacyclohexane or paraffin, alcohol and ethylene glycol and their ether
And ester, such as ethanol, ethylene glycol, ethylene glycol monomethyl；Ketone, such as cyclohexanone, such as highly polar solvent, N- methyl -2- pyrrolidines
Ketone, dimethyl sulfoxide (DMSO) or dimethylformamide, and vegetable oil or vegetable oil, such as soybean oil.
Above-mentioned solid carrier, is such as used for pulvis and dispersibles the typically natural mineral fillers of agent, such as talcum, kaolinite
Soil, montmorillonite or atlapulgite.In order to manage the physical property of composition, it is also possible to add polymolecularity silicic acid or polymolecularity
Adsorpting polymerization thing carrier, such as granulated adsorptive carriers or non-adsorbed carrier, suitable granulated adsorptive carriers are porous types, such as floating
Stone, bentonite or bentonite；Suitable non-adsorbed carrier such as calcite or sand.Further, it is possible to use substantial amounts of inorganic in nature or having
The prefabricated material for granulating of machine property is used as carrier, particularly dolomite.
The chemical property of the active ingredient in composition of the invention, suitable surfactant is sulfomethylated lignin
Acid, naphthalene sulfonic acids, phenolsulfonic acid, alkali salt or amine salt, alkylaryl sulfonates, alkyl sulfate, alkylsulfonate, fat
The condensation product of alcohol sulfate, aliphatic acid and sulphated fatty alcohol glycol ether, also sulfonated naphthalene and naphthalene derivatives and formaldehyde, naphthalene or
Naphthalene sulfonic acids and phenol and the condensation product of formaldehyde, NONIN HS 240, ethoxylated isooctyl-phenol, octyl phenol, nonyl phenol,
Alkylaryl polyglycol ether, tributyl benzene polyglycol ether, three stearyl phenyl polyglycol ethers, alkyl aryl polyether alcohol,
Ethoxylated castor oil, polyoxyethylene alkyl ether, ethylene oxide condensation product, ethoxylation polyoxypropylene, bay acid polyethylene glycol
Ether acetal, sorbitol ester, lignin sulfite waste liquor and methylcellulose.
Pharmaceutically acceptable salt in the present invention represents those of the biological effectiveness of reservation parent compound and property
Salt.This kind of salt includes：
(1) obtained, inorganic acid bag by the free alkali and inorganic acid of parent compound or the reaction of organic acid into salt with acid
Include hydrochloric acid, hydrobromic acid, nitric acid, phosphoric acid, metaphosphoric acid, sulfuric acid, sulfurous acid and perchloric acid etc., organic acid include acetic acid, trifluoroacetic acid,
Propionic acid, acrylic acid, caproic acid, pentamethylene propionic acid, glycolic, pyruvic acid, oxalic acid, (D) or (L) malic acid, fumaric acid, maleic acid,
Benzoic acid, hydroxybenzoic acid, gamma-hydroxybutyric acid, methoxy benzoic acid, phthalic acid, methanesulfonic acid, ethyl sulfonic acid, naphthalene -1- sulphurs
Acid, naphthalene-2-sulfonic acid, p-methyl benzenesulfonic acid, salicylic acid, tartaric acid, citric acid, lactic acid, cinnamic acid, dodecyl sulphate, gluconic acid,
Glutamic acid, aspartic acid, stearic acid, mandelic acid, butanedioic acid or malonic acid etc..
(2) acid proton being present in parent compound is replaced or given birth to organic base ligand compound by metal ion
Into salt, metal ion such as alkali metal ion, alkaline-earth metal ions or aluminium ion, organic bases for example monoethanolamine, diethanol amine,
Triethanolamine, tromethamine, N-METHYL-ALPHA-L-GLUCOSAMINE, quinine etc..
Pharmaceutical composition in the present invention refer to by one or more in the compound in the present invention or its pharmaceutically may be used
The salt of acceptance, solvate, hydrate or prodrug and other chemical composition, such as pharmaceutically acceptable carrier, mixing.Medicine
The purpose of composition is the process for promoting administration to animal.
The compound or its pharmaceutically acceptable salt of the present invention can be applicable to crops weeding aspect, particularly apply
Prevent and kill off grassy weed aspect.The compound of the present invention, without any adverse effect, is not required to the normal growth of wheat class crops
Safener is added, its dosage is little, herbicidal spectrum is wide, and herbicidal effect is good, used in being more beneficial for agricultural production.
Specific embodiment
With reference to embodiments the invention will be further described.But the scope of the present invention is not limited to following enforcement
Example.
Embodiment 1：Formula (1) compound (R) -2- [4- (the fluoro- 2- pyridines epoxides of the chloro- 3- of 5-) phenoxy group] propionic acid (2,2 '-two
Fluoro ethyl) ester preparation
500gDMF is added into 1000mL four-hole boiling flasks, 100g compound A, 113.6g potassium carbonate and the 5g tetrabutyls is put into
Ammonium bromide, is warming up to 60 DEG C, and 90.3g compound B are added dropwise, and controls 60～55 DEG C of temperature, and completion of dropwise addition is reacted about 2 hours, reaction
Terminate, in adding to 1000g water, with salt acid for adjusting pH to 7～8, stir 1 hour, filter, solid is etherate, dries.
500g dichloroethanes is added in 1000ml four-hole bottles, 100g compound C are added, 50 DEG C are warming up to, 45.8g is added dropwise
Thionyl chloride, controls 50～55 DEG C of temperature, and completion of dropwise addition is reacted 1 hour, and reaction terminates, and acyl chloride reaction liquid is standby.
Add 52.7g2,2 '-difluoroethanol to be cooled to 0～5 DEG C in 1000ml four-hole bottles, acyl chloride reaction liquid, control is added dropwise
0～5 DEG C of temperature processed, completion of dropwise addition is reacted 1 hour, and reaction terminates, precipitation, obtains crude product, adds 50g methyl alcohol to be warming up to 50 DEG C
Dissolving, is cooled to 5 DEG C, separates out solid, is filtrated to get product, off-white powder, yield：78%, content：95%.
MS (ESI) m/z=335.27 [M+H]+.
Embodiment 2：Formula (1) compound (R) -2- [4- (the fluoro- 2- pyridines epoxides of the chloro- 3- of 5-) phenoxy group] propionic acid (2,2 '-two
Fluoro ethyl) ester preparation
500g toluene is added into 1000mL four-hole boiling flasks, 100g compound A, 87.3g sodium carbonate and the 5g tetrabutyls is put into
Ammonium bromide, is warming up to 60 DEG C, and 90.3g compound B are added dropwise, and controls 60～55 DEG C of temperature, and completion of dropwise addition is reacted about 2 hours, reaction
Terminate, in adding to 1000g water, with salt acid for adjusting pH to 7～8, stir 1 hour, layering, organic phase precipitation obtains solid and as changes
Compound C, drying.
500g dichloroethanes is added in 1000ml four-hole bottles, 100g compound C are added, 50 DEG C are warming up to, 48.9g is added dropwise
Oxalyl chloride, controls 50～55 DEG C of temperature, and completion of dropwise addition is reacted 1 hour, and reaction terminates, and acyl chloride reaction liquid is standby.
Add 52.7g2,2 '-difluoroethanol to be cooled to 0～5 DEG C in 1000ml four-hole bottles, acyl chloride reaction liquid, control is added dropwise
0～5 DEG C of temperature processed, completion of dropwise addition is reacted 1 hour, and reaction terminates, precipitation, obtains crude product, adds 50g methyl alcohol to be warming up to 50 DEG C
Dissolving, is cooled to 5 DEG C, separates out solid, is filtrated to get product, off-white powder, yield：75%, content：95%.
Embodiment 3：15% wettable powder
Compound (R) -2- [4- (the fluoro- 2- pyridines epoxides of the chloro- 3- of 5-) phenoxy group] propionic acid (2,2 '-two fluoro ethyl) ester
15%, sodium lignin sulfonate 6%, alkylsulfonate 5%, white carbon 8%, kaolin complements to 100%.
Active component and various auxiliary agents and filler etc. are sufficiently mixed in proportion, are obtained Jing after ultra-fine pulverizer disintegrating wettable
Property pulvis.
Embodiment 4：40% wettable powder
Compound (R) -2- [4- (the fluoro- 2- pyridines epoxides of the chloro- 3- of 5-) phenoxy group] propionic acid (2,2 '-two fluoro ethyl) ester
40%, bentonite 3%, alkylsulfonate 3%, white carbon 5%, diatomite complements to 100%.
Active component and various auxiliary agents and filler etc. are sufficiently mixed in proportion, are obtained Jing after ultra-fine pulverizer disintegrating wettable
Property pulvis.
Embodiment 5：70% wettable powder
Compound (R) -2- [4- (the fluoro- 2- pyridines epoxides of the chloro- 3- of 5-) phenoxy group] propionic acid (2,2 '-two fluoro ethyl) ester
70%, aliphatic alcohol sulfate 6%, calcite 3%, kaolin 7%, precipitated calcium carbonate complements to 100%.
Active component and various auxiliary agents and filler etc. are sufficiently mixed in proportion, are obtained Jing after ultra-fine pulverizer disintegrating wettable
Property pulvis.
Embodiment 6：10% water dispersible granules
Compound (R) -2- [4- (the fluoro- 2- pyridines epoxides of the chloro- 3- of 5-) phenoxy group] propionic acid (2,2 '-two fluoro ethyl) ester
10%, Sodium Benzoate 5%, alkyl polyoxyethanyl ether sulfonate 5%, fatty mercaptan acid ammonium 4%, kaolin complements to 100%.
Active component, auxiliary agent and filler are well mixed in the ratio of formula, Jing air-flow crushings are into wettable powder, then add
Enter a certain amount of water mixing extruder grain, water dispersible granules product is obtained after drying screening.
Embodiment 7：30% missible oil
Compound (R) -2- [4- (the fluoro- 2- pyridines epoxides of the chloro- 3- of 5-) phenoxy group] propionic acid (2,2 '-two fluoro ethyl) ester
30%, propane diols 15%, alkylaryl polyglycol ether 10%, toluene complements to 100%.
Embodiment 8：Drug effect checking test
Test medicine is 15% wettable powder of embodiment 3, and comparison medicament is the clodinafop-propargyl wettable powder of wheat pole 15%
(first just reaching), test sets altogether three process, and each counterpoise that processes is multiple 5 times, is 23m per plot area2, district's groups arrangement immediately.
In morning dispenser by the end of December, number of times is 1 time, using cauline leaf spray-on process even spraying.During dispenser at grassy weed
In the 3-6 leaf phases, wheat processes the 6-7 leaf phases.
Weeds radix is investigated before dispenser, 15d, 21d, 45d investigation residual weeds strain number after medicine.Occur if any poisoning, according to
Poisoning grade scale, record poisoning type and degree.
Result of the test is shown in Table 1-2.
Table 1 respectively processes the strain preventive effect and fresh weight preventive effect to barnyard grass
Table 2 respectively processes the strain preventive effect and fresh weight preventive effect to grassy weed
Process 1,2,3 above has obvious exception during being showed no wheat growth.
Claims (10)
1. the compound or its pharmaceutically acceptable salt of structure shown in formula (1),
2. the preparation method of compound described in a kind of claim 1, it is characterised in that compound A and B carries out etherification reaction and obtains
Compound C, then acyl chlorides synthetic reaction synthesis compound D is carried out, esterification formula (1) compound is finally carried out,
3. preparation method according to claim 2, it is characterised in that it comprises the steps：
Step A：Etherification reaction, compound A and compound B adds in the basic conditions catalyst to carry out reaction and obtains compound C；
Step B：Acyl chlorides synthetic reaction, compound C carries out reaction and obtains acyl chlorides with acylating reagent；
Step C：Esterification, compound D and 2,2- difluoroethanol carry out at low temperature reaction and obtain formula (1) compound.
4. preparation method according to claim 3, it is characterised in that in step, compound A and compound B mole
Than for 1:1～1:1.5；The alkali of alkalescence condition is sodium carbonate, potassium carbonate or sodium acid carbonate；The catalyst is phase transfer catalysis (PTC)
Agent；Reaction dissolvent is DMF, 1,2- dichloroethanes or toluene；Reaction temperature is 55～110 DEG C, preferably at 70～75 DEG C.
5. preparation method according to claim 4, it is characterised in that in step, compound A and compound B mole
Than for 1:1.1；The catalyst is TBAB, tetrabutylammonium chloride or benzyltriethylammoinium chloride；Reaction temperature is
70～75 DEG C.
6. preparation method according to claim 3, it is characterised in that in stepb, compound C and acylating reagent mole
Than being 1:1～1:1.5；The acylating reagent is thionyl chloride or oxalyl chloride；Reaction dissolvent is dichloromethane, 1,2- dichloroethanes
Or toluene；Reaction temperature is 40～80 DEG C.
7. preparation method according to claim 6, it is characterised in that in stepb, compound C and acylating reagent mole
Ratio is 1:1.2；Reaction temperature is 60～65 DEG C.
8. preparation method according to claim 3, it is characterised in that in step C, compound D and 2,2- difluoroethanol
Mol ratio is 1:1～1:3, preferably 1:2；Reaction temperature is -5 DEG C～15 DEG C, preferably 0～5 DEG C.
9. a kind of Herbicidal combinations, it is characterised in that it is with the compound described in claim 1 or its pharmaceutically acceptable salt
For active component or main active, it is aided with acceptable auxiliary agent on agricultural chemicals.
10. purposes of the compound or its pharmaceutically acceptable salt described in claim 1 in terms of crops weeding, particularly
Purposes in terms of grassy weed is prevented and kill off.
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| CN111747888A (en) * | 2020-06-29 | 2020-10-09 | 江苏富鼎化学有限公司 | Pyridyloxyphenoxypropionamide compound with herbicidal activity and synthetic method and application thereof |
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| CN111747888A (en) * | 2020-06-29 | 2020-10-09 | 江苏富鼎化学有限公司 | Pyridyloxyphenoxypropionamide compound with herbicidal activity and synthetic method and application thereof |
| CN114292228A (en) * | 2021-12-30 | 2022-04-08 | 江苏富鼎化学有限公司 | The synthetic method of clodinafop-propargyl |
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