CN1317482A - 2,4-substituted phenoxypropanamide compounds and preparing process and application thereof - Google Patents
2,4-substituted phenoxypropanamide compounds and preparing process and application thereof Download PDFInfo
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- CN1317482A CN1317482A CN 01115594 CN01115594A CN1317482A CN 1317482 A CN1317482 A CN 1317482A CN 01115594 CN01115594 CN 01115594 CN 01115594 A CN01115594 A CN 01115594A CN 1317482 A CN1317482 A CN 1317482A
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- phenoxypropanamide
- substituting group
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- ANCDHBXLDURTHN-UHFFFAOYSA-N 2-phenoxypropanamide Chemical class NC(=O)C(C)OC1=CC=CC=C1 ANCDHBXLDURTHN-UHFFFAOYSA-N 0.000 title claims abstract description 8
- 238000000034 method Methods 0.000 title description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 30
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 25
- -1 heterocycle amine Chemical class 0.000 claims description 16
- 238000010992 reflux Methods 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 239000011230 binding agent Substances 0.000 claims description 5
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 5
- 235000015320 potassium carbonate Nutrition 0.000 claims description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- 239000005648 plant growth regulator Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- ZHWUKRORIAVONG-UHFFFAOYSA-N C(CC)(=O)N.[O].C1=CC=CC=C1 Chemical class C(CC)(=O)N.[O].C1=CC=CC=C1 ZHWUKRORIAVONG-UHFFFAOYSA-N 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 235000011118 potassium hydroxide Nutrition 0.000 claims description 2
- 235000017550 sodium carbonate Nutrition 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 4
- SBSYFELXUYBRND-UHFFFAOYSA-N 3-phenoxypropanoyl chloride Chemical compound ClC(=O)CCOC1=CC=CC=C1 SBSYFELXUYBRND-UHFFFAOYSA-N 0.000 claims 3
- 150000001412 amines Chemical class 0.000 claims 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 239000002798 polar solvent Substances 0.000 claims 1
- 230000002194 synthesizing effect Effects 0.000 claims 1
- 240000006995 Abutilon theophrasti Species 0.000 abstract description 5
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 241001233957 eudicotyledons Species 0.000 abstract description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- 230000002363 herbicidal effect Effects 0.000 abstract 1
- 239000004009 herbicide Substances 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 239000012188 paraffin wax Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 230000026267 regulation of growth Effects 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- 230000012010 growth Effects 0.000 description 24
- 239000002585 base Substances 0.000 description 22
- 240000008067 Cucumis sativus Species 0.000 description 20
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 20
- 239000002904 solvent Substances 0.000 description 18
- 241000196324 Embryophyta Species 0.000 description 16
- 238000001816 cooling Methods 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000007789 gas Substances 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 230000006837 decompression Effects 0.000 description 10
- 229960000935 dehydrated alcohol Drugs 0.000 description 10
- 238000001035 drying Methods 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- 238000001953 recrystallisation Methods 0.000 description 10
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 9
- 238000004587 chromatography analysis Methods 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- 230000001105 regulatory effect Effects 0.000 description 9
- 239000012044 organic layer Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 238000010792 warming Methods 0.000 description 8
- 238000009333 weeding Methods 0.000 description 8
- 238000013019 agitation Methods 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- KRZCOLNOCZKSDF-UHFFFAOYSA-N 4-fluoroaniline Chemical compound NC1=CC=C(F)C=C1 KRZCOLNOCZKSDF-UHFFFAOYSA-N 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- 150000001555 benzenes Chemical class 0.000 description 5
- 230000008635 plant growth Effects 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 244000237956 Amaranthus retroflexus Species 0.000 description 4
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- STVWDDZUEVJZKZ-UHFFFAOYSA-N C(CC)(=O)O.[O].ClC1=CC=CC(=C1)Cl Chemical compound C(CC)(=O)O.[O].ClC1=CC=CC(=C1)Cl STVWDDZUEVJZKZ-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 230000002786 root growth Effects 0.000 description 4
- 238000010998 test method Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 240000006122 Chenopodium album Species 0.000 description 3
- 235000009344 Chenopodium album Nutrition 0.000 description 3
- 244000068988 Glycine max Species 0.000 description 3
- 235000010469 Glycine max Nutrition 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 240000006677 Vicia faba Species 0.000 description 3
- 235000010749 Vicia faba Nutrition 0.000 description 3
- 235000002098 Vicia faba var. major Nutrition 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 231100000572 poisoning Toxicity 0.000 description 3
- 230000000607 poisoning effect Effects 0.000 description 3
- 238000002791 soaking Methods 0.000 description 3
- 208000024891 symptom Diseases 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 2
- UDWMNHRPJRAISD-UHFFFAOYSA-N 2-(2-chloro-4-fluorophenoxy)-N-(4-fluorophenyl)propanamide Chemical compound C=1C=C(F)C=CC=1NC(=O)C(C)OC1=CC=C(F)C=C1Cl UDWMNHRPJRAISD-UHFFFAOYSA-N 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- CPPBGBUEWTYGSP-UHFFFAOYSA-N 3-(4-fluorophenoxy)propanoyl chloride Chemical compound FC1=CC=C(OCCC(Cl)=O)C=C1 CPPBGBUEWTYGSP-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- 241000209140 Triticum Species 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000005080 plant death Effects 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- HXKWSTRRCHTUEC-UHFFFAOYSA-N 2,4-Dichlorophenoxyaceticacid Chemical compound OC(=O)C(Cl)OC1=CC=C(Cl)C=C1 HXKWSTRRCHTUEC-UHFFFAOYSA-N 0.000 description 1
- WIVLMXDHGGRLMP-UHFFFAOYSA-N 2-(4-fluorophenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(F)C=C1 WIVLMXDHGGRLMP-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical class CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- DFVFQSNJOFPICB-UHFFFAOYSA-N 2-[2-chloro-4-(trifluoromethyl)phenoxy]propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(C(F)(F)F)C=C1Cl DFVFQSNJOFPICB-UHFFFAOYSA-N 0.000 description 1
- AUHYZQCEIVEMFH-UHFFFAOYSA-N 2-bromopropanamide Chemical compound CC(Br)C(N)=O AUHYZQCEIVEMFH-UHFFFAOYSA-N 0.000 description 1
- MONMFXREYOKQTI-UHFFFAOYSA-N 2-bromopropanoic acid Chemical compound CC(Br)C(O)=O MONMFXREYOKQTI-UHFFFAOYSA-N 0.000 description 1
- CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 1
- 240000001592 Amaranthus caudatus Species 0.000 description 1
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 1
- 235000017060 Arachis glabrata Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 235000018262 Arachis monticola Nutrition 0.000 description 1
- 241000981770 Buddleja asiatica Species 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- CEDZFAONRDZJKJ-UHFFFAOYSA-N [O].ClC1=CC=CC(=C1)Cl Chemical compound [O].ClC1=CC=CC(=C1)Cl CEDZFAONRDZJKJ-UHFFFAOYSA-N 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 235000012735 amaranth Nutrition 0.000 description 1
- WGQKYBSKWIADBV-UHFFFAOYSA-N aminomethyl benzene Natural products NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- YAVVGPBYBUYPSR-UHFFFAOYSA-N benzene;oxygen Chemical compound [O].C1=CC=CC=C1 YAVVGPBYBUYPSR-UHFFFAOYSA-N 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 150000005826 halohydrocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 210000001161 mammalian embryo Anatomy 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000004899 motility Effects 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 230000000452 restraining effect Effects 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
A process for preparing 2,4-substituted phenoxypropanamide compounds uses 2,4-substituted phenoxypropanamide as mother body and features that the paraffin and substituted phenyl or nitrogen-contained heterocycle are introduced to its nitrogen actoms to form said compounds. Said compounds can be used as herbicide of piemarker, etc. and has high growth regulation function to dicotyledon.
Description
The present invention relates to used compound of a kind of agriculture weeding and plant growth regulating and its production and application, relate in particular to a kind of 2,4-substituted phenoxypropanamide compounds and its production and application.
Along with Increase of population, the attention day by day of the development of world agriculture and environment protection is had higher requirement to the development of agrochemicals now, and this compounds must have efficiently, low toxicity, the strong and environment amenable characteristics of selectivity.
The 2,4 dichlorophenoxyacetic acid that the sixties propose (2,4-D) and 2,4 dichloro benzene oxygen propionic acid (2,4-DP) weeding preferably and plant growth regulating activity are arranged, but the large usage quantity of this compounds, and the root system of plant are had stronger restraining effect.
The disclosed benzene oxygen of Japanese Patent JP-04-202168 acyl benzylamine compound-biflubutamid has certain weeding activity, when consumption 170～255g/ha, can effectively prevent and kill off, control the broadleaf weeds of cereal crop, have the preceding weeding activity of preferable bud, but it does not have the plant growth regulation that compound involved in the present invention has.
Of the present invention is a kind of new remarkable bioactive benzene oxygen Propionamides compound that has, it not only has the weeding activity of wide spectrum, especially compound ii. possess higher plant growth regulating activity, especially some dicotyledonous class cash crop are had the effect that promotes growth, hestening rooting preferably.
One of purpose of the present invention is to disclose a class and is applicable to 2 of weed control and plant growth regulating on the agricultural plants, 4-substituting group benzene oxygen propanamide compounds efficiently;
Two of purpose of the present invention is to disclose the preparation method of said compound;
Three of purpose of the present invention is to disclose the application of said compound as weedicide or plant-growth regulator.
Compound provided by the invention has the following chemical structure formula I:
Wherein:
R
1Be H, CH
3, C
2H
5, a kind of among the i-Pr;
X is 2,4-Cl
2, 2-Cl-4-F, 2-Cl-4-CF
3In a kind of;
Y is 3-CF
3, 2,6-F
2, 2,6-i-Pr, 4-F, 3,5-F
2, 2,4-F
2In a kind of;
Z is H, 2,6-N
2, a kind of among the 3-N.Compound involved in the present invention prepares by following two kinds of methods: method A:
Method B:
In above preparation method A and B, reaction is carried out in inert solvent usually, and solvent comprises aromatic hydrocarbon (as benzene,toluene,xylene); Halohydrocarbon (as chlorobenzene, tetracol phenixin, chloroform, methylene dichloride, 1,2-ethylene dichloride); Ether (as ether, tetrahydrofuran (THF), diox); Ketone (as acetone, methylethylketone, mibk); Methyl-sulphoxide, Nitromethane 99Min. and mixture.
Should add acid binding agent (as mineral alkali and organic bases such as triethylamines etc. such as yellow soda ash, salt of wormwood, sodium hydroxide, potassium hydroxide) in the reaction, the molar ratio range of its consumption and acyl chlorides is 1: 1～2.Preferable range is 1: 1.1～1.5.
Among method A and the B, reaction is carried out under normal pressure usually, and the reaction times is 1～10 hour, especially at 4～8 hours.
In method A and B, between 10～140 ℃, temperature is controlled at 80～110 ℃ of preferable range to temperature of reaction among the method A usually; Temperature of reaction is controlled in 110～130 ℃ of preferable range among the method B.
By the compound that aforesaid method makes, adding-quantitative water, the amount ranges of water is 50-200ml, behind standing demix, organic phase adds the siccative drying, the elimination siccative, organic solvent is sloughed in decompression.In resistates, add recrystallizations twice such as organic solvent such as methyl alcohol, dehydrated alcohol, Virahol, acetone, methyl iso-butyl ketone (MIBK), obtain white crystalline solid.
In the present invention, represented chloride compounds can react in halogeno-benzene, halogenated hydrocarbon solvent by corresponding acid and sulfur oxychloride, phosphorus trichloride and obtains in the general formula III.
The bromo propionic acid amide that the general formula IV is represented can prepare by the following method:
In the present invention, compound 2-(2,4 dichloro benzene oxygen base)-N-4-fluorophenyl propionic acid amide (II) has good regulating effect to the growth of cucumber seedling when the blade spraying of 10 μ g/ml, can promote the growth of seedling of dicotyledonss such as broad bean, soybean.Seed soaking can improve the resistance against diseases of cucumber seedling to samping off when handling, and the growth of cucumber lateral root is also had promoter action.
Described chemical compounds I produces obvious suppression growth and withered effect to broadleaf weedss such as Amaranthus retroflexus, water peanut, piemarker, iron amaranths.
Embodiment 1:2-(2,4 dichloro benzene oxygen base)-N-4-fluorophenyl propionic acid amide
A. under ice bath, agitation condition, in the four-hole bottle that cooling and reflux device, thermometer and Dropping feeder are housed, add triethylamine (2g, 0.02mol), para-fluoroaniline (2.3g, 0.021mol) and 30ml toluene liquid, drip 2,4 dichloro benzene oxygen propionyl chloride (5.07g in 5 ℃, 0.02mol) 10ml toluene liquid, drip and finish, stir in a moment, be warming up to reflux state, be incubated after 4 hours naturally cooling.Add 100ml water, the washing layering.Get organic layer, through the anhydrous magnesium sulfate thorough drying, after most of solvent was sloughed in decompression, resistates added entry, dehydrated alcohol in bottle, behind recrystallization, got the 6.4g white crystal.Recording fusing point 120-122 ℃, is 96% through gas chromatographic analysis content, yield Y=93.6%.
B. under ice bath, agitation condition, in the four-hole bottle that cooling and reflux device, thermometer and Dropping feeder are housed, add powdered salt of wormwood (2.4g, 0.02mol), para-fluoroaniline (2.2g, 0.021mol) and 30ml toluene, drip 2,4 dichloro benzene oxygen propionyl chloride (5.07 g in 5 ℃, 0.02mol) the 10ml toluene solution, drip and finish, stir in a moment, be warming up to reflux state, be incubated after 4 hours naturally cooling.Add 100ml water, the washing layering.Get organic layer, through the anhydrous magnesium sulfate thorough drying, after most of solvent was sloughed in decompression, resistates added entry, dehydrated alcohol in bottle, behind recrystallization, got the 5.6g white crystal.Recording fusing point 120-122 ℃, is 98% through gas chromatographic analysis content, yield Y=81.8%.
C. under ice bath, agitation condition, in the four-hole bottle that cooling and reflux device, thermometer and Dropping feeder are housed, add triethylamine (2g, 0.02mol), para-fluoroaniline (2.2g, 0.021mol) and the 30ml ethylene dichloride, drip 2,4 dichloro benzene oxygen propionyl chloride (5.07g in 5 ℃, 0.02mol) the 10ml dichloroethane solution, drip and finish, stir in a moment, be warming up to reflux state, be incubated after 4 hours naturally cooling.Add 100ml water, the washing layering.Get organic layer, through the anhydrous magnesium sulfate thorough drying, after most of solvent was sloughed in decompression, resistates added entry, dehydrated alcohol in bottle, behind recrystallization, got the 6.26g white crystal.Recording fusing point 120-122 ℃, is 98% through gas chromatographic analysis content, yield Y=91.5%.
2,4 dichloro benzene oxygen propionyl chloride can be by 2,4 dichloro benzene oxygen propionic acid and sulfur oxychloride, react in the chlorinated benzene solvent and obtain.Embodiment 2:2-(2,4 dichloro benzene oxygen base)-N-3-pyridyl propionic acid amide
Under ice bath, agitation condition, in the four-hole bottle that cooling and reflux device, thermometer and Dropping feeder are housed, add triethylamine (2g, 0.02mol), 3-pyridine amine (2.0g, 0.021mol) and 30ml toluene liquid, drip 2,4 dichloro benzene oxygen propionyl chloride (5.07g in 5 ℃, 0.02mol) 10ml toluene liquid, drip and finish, stir in a moment, be warming up to reflux state, be incubated after 4 hours naturally cooling.Add 100ml water, the washing layering.Get organic layer, through the anhydrous magnesium sulfate thorough drying, after most of solvent was sloughed in decompression, resistates added entry, dehydrated alcohol in bottle, behind recrystallization, got the 5.9g white crystal.Recording fusing point is 223-235 ℃.Through gas chromatographic analysis content is 95.5%, yield Y=90.5%.
2,4 dichloro benzene oxygen propionyl chloride can be by 2,4 dichloro benzene oxygen propionic acid and sulfur oxychloride, react in the chlorinated benzene solvent and obtain.Embodiment 3:2-(2,4 dichloro benzene oxygen base)-N-2,6-pyrimidyl propionic acid amide
Under ice bath, agitation condition, in the four-hole bottle that cooling and reflux device, thermometer and Dropping feeder are housed, add triethylamine (2g, 0.02mol), 2, the 6-PYRIMITHAMINE (2g, 0.021mol) and 30ml toluene liquid, drip 2 in 5 ℃, (5.07g, 10ml toluene liquid 0.02mol) drip and finish 4-Dichlorophenoxy propionyl chloride, stir in a moment, be warming up to reflux state, be incubated after 4 hours naturally cooling.Add 100ml water, the washing layering.Get organic layer, through the anhydrous magnesium sulfate thorough drying, after most of solvent was sloughed in decompression, resistates added entry, dehydrated alcohol in bottle, behind recrystallization, got the 6.0g white crystal.Recording fusing point is 231-233 ℃.Through gas chromatographic analysis content is 97%, yield Y=93.4%.
2,4 dichloro benzene oxygen propionyl chloride can be by 2,4 dichloro benzene oxygen propionic acid and sulfur oxychloride, react in the chlorinated benzene solvent and obtain.Embodiment 4:2-(2-chlorine 4-fluorophenoxy)-N-4-fluoro-Phenylpropionamide
Under ice bath, agitation condition, in the four-hole bottle that cooling and reflux device, thermometer and Dropping feeder are housed, add triethylamine (2g, 0.02mol), para-fluoroaniline (2.2g, 0.021mol) and 30ml toluene liquid, (4.74g, 10ml toluene liquid 0.02mol) drip and finish to drip 2-chlorine 4-fluorophenoxy propionyl chloride in 5 ℃, stir in a moment, be warming up to reflux state, be incubated after 4 hours naturally cooling.Add 100ml water, the washing layering.Get organic layer, through the anhydrous magnesium sulfate thorough drying, after most of solvent was sloughed in decompression, resistates added entry, dehydrated alcohol in bottle, behind recrystallization, got the 6.3g white crystal.Recording fusing point 110-112 ℃, is 95% through gas chromatographic analysis content, yield Y=96.5%.
2-chlorine 4-fluorophenoxy propionyl chloride can be by 2-chlorine 4-fluorophenoxy propionic acid and sulfur oxychloride, react in the chlorinated benzene solvent and obtain.Embodiment 5:2-(2-chloro-4-4-trifluoromethylphenopendant)-N-4-fluoro-Phenylpropionamide
Under ice bath, agitation condition, in the four-hole bottle that cooling and reflux device, thermometer and Dropping feeder are housed, add triethylamine (2g, 0.02mol), para-fluoroaniline (2.2g, 0.021mol) and the 30ml ethylene dichloride, (5.74g, 10ml dichloroethane solution 0.02mol) drip and finish to drip 2-chloro-4-trifluoromethylbenzene oxygen propionyl chloride in 5 ℃, stir in a moment, be warming up to reflux state, be incubated after 4 hours naturally cooling.Add 100ml water, the washing layering.Get organic layer, through the anhydrous magnesium sulfate thorough drying, after most of solvent was sloughed in decompression, resistates added entry, dehydrated alcohol in bottle, behind recrystallization, got the 6.93g white crystal.Recording fusing point 131-132 ℃ is 95.5% through gas chromatographic analysis content, yield Y=91.5%.
2-chloro-4-trifluoromethylbenzene oxygen propionyl chloride can be by 2-chloro-4-trifluoromethyl phenoxy propionic acid and sulfur oxychloride, react in the chlorinated benzene solvent and obtain.Embodiment 6:2-(2,4 dichloro benzene oxygen base)-N-3-trifluoromethyl propionic acid amide
Have whipping appts one, condenser, add methyl-sulphoxide in the four-hole bottle of thermometer in batches and (be called for short DMSO, 50ml), salt of wormwood (5.5g, 0.04mol), 2,4-chlorophenesic acid (3.3g, 0.02mol) and 2-bromo-N3-trifluoromethyl propionic acid amide (5.9g, 0.02mol), stirring heating is at 120 ℃ of internal reactions after 8 hours, after cooling adds 100ml water, extract after adding methylene dichloride 50ml, get organic layer, after most of solvent is sloughed in decompression through anhydrous magnesium sulfate drying, resistates adds entry in bottle, dehydrated alcohol gets 6.27g pine tag needle-like crystal behind recrystallization.Recording fusing point is 108-110 ℃, is 97.3% through gas chromatographic analysis content, yield Y=78.2%.Embodiment 7-24: it is as shown in table 1 to make following compounds by similar approach:
Annotate: 1. acid binding agent all adopts triethylamine except that indicating, and molar weight is 1: 1;
2. except that indicating, solvent all adopts toluene;
3.* show the synthetic B of employing method;
4.a show that adopting solvent is ethylene dichloride;
5.b showing the reaction times is 12 hours
6.C showing acid binding agent is salt of wormwood embodiment 25:2-bromo-N-(3-trifluoromethyl-phenyl) propionic acid amide
Have whipping appts, condenser, temperature to take into account in the four-hole bottle of device for absorbing tail gas one, add 2 bromopropionic acid (15.3g, 0.1mol) and toluene liquid (100ml), drip the 3-5-trifluoromethylaniline after, heat up and be heated to 55 ℃, slowly drip POCl
3(7.66g, 0.05mol).There is HCl gas to generate.Drip and finish, slowly be warming up to backflow, be incubated 2 hours, naturally cool to room temperature, add 50ml water, after the layering, water layer is through 20ml toluene extraction, merge organic phase after, add l0% diluted alkaline water, be washed to pH value and be neutrality, get organic phase through anhydrous magnesium sulfate drying, after most of solvent was sloughed in decompression, resistates added entry, dehydrated alcohol in bottle, behind recrystallization, get the 27.3g white crystal, through gas chromatographic analysis, content is 97%, and yield is 89.4%.Embodiment 26: biological activity test
A:2-(2,4 dichloro benzene oxygen base)-N-4-fluoro-Phenylpropionamide is to the regulating effect of cucumber seedling growth
1. test method: with 2-(2,4 dichloro benzene oxygen base)-N-4-fluoro-Phenylpropionamide become 1000 μ g/ml,
7 kinds of differences such as 500 μ g/ml, 250 μ g/ml, 125 μ g/ml, 62.5 μ g/ml, 1 μ g/ml are dense
Degree, spray is distributed on the cucumber seedling, and every concentration sprays the l alms bowl, and 2 strains of every alms bowl plantation cucumber seedling are behind the spray medicine
Cucumber seedling place 25 ℃ of cultivations, after 2 days the record 3 petiole length of launching leaf fully, 10 days,
The growing state of record cucumber seedling after 18 days.
Table 1.2-(2,4 dichloro benzene oxygen base)-N-4-fluoro-Phenylpropionamide
The influence of behind the processing cucumber seedling petiole being extended
| Concentration of treatment (μ g/ml) | Petiole length (cm) before handling | Handle petiole length (cm) after 2 days | Petiole stretch value (cm) in 2 days | The elongation of chemicals treatment petiole elongation/blank petiole |
| ????0(ck) | ????3.0 | ????3.2 | ????0.2 | ????1 |
| ????1 | ????3.0 | ????3.5 | ????0.5 | ????2.5 |
| ????10 | ????3.1 | ????3.9 | ????0.8 | ????4 |
| ????62.5 | ????3.0 | ????4.5 | ????1.5 | ????7.5 |
| ????125 | ????3.0 | ????5.5 | ????2.5 | ????12.5 |
| ????250 | ????3.0 | ????5.5 | ????2.5 | ????12.5 |
| ????500 | ????3.0 | ????5.5 | ????2.5 | ????12.5 |
| ????1000 | ????3.0 | ????5.5 | ????2.5 | ????12.5 |
Table 2.2-(2,4 dichloro benzene oxygen base)-N-4-fluoro-Phenylpropionamide
Handle plant strain growth situation after 18 days
| Concentration of treatment (μ g/ml) | The plant strain growth situation |
| 0 (ck) | The leaf look pale yellow, a little less than the growth potential |
| 1 | Leaf look green, growth potential is slightly stronger than blank |
| 10 | Dark green leaf color, robust growth |
| 62.5 | New leafing is green, bottom Ye Qianhuang |
| 125 | The leaf look pale yellow, and no young leaves grows.Plant stops growing |
| 250 | Bottom leaf death, upper leaf is pale yellow, and no young leaves grows, and plant strain growth stops. |
| 500 | The yellow of leaf look, no young leaves grows, and stem apex is withered, and plant strain growth stops |
| 1000 | Plant death. |
2. test-results: test-results shows, 1 μ g/ml, l0 μ g/ml, 62.5 μ g/ml, 125 μ g/ml, 250 μ g/ml, 500 μ g/ml, 1000 μ g/ml all can obviously promote the elongation of petiole, the petiole elongation reaches maximum value during 125 μ g/ml, the many 2cm of petiole ratio of elongation blank in 2 days, elongation speed is 12.5 times of blank.Find after 10 days after the chemicals treatment: concentration is at 62.5 μ g/ml and when above, and the growth table of cucumber seedling reveals tangible poisoning, mainly shows as the distortion of petiole deformity, and the stem deformity is expanded cracking.Compare with blank, the cucumber seedling leaf look that 10 μ g/ml handled turns green, the cauline leaf robust growth.After the medication 18 days, the plant strain growth stalwartness that 10 μ g/ml handled, the plant that 1000 μ g/ml handled then makes plant death.Test-results shows, below 62.5 μ g/ml, in this example, compound 2-(2,4 dichloro benzene oxygen base)-N-4-fluoro-Phenylpropionamide helps the growth of cucumber seedling with the consumption of 10 μ g/ml to JSP-902 to the safe concentration of cucumber.B:2-(2,4 dichloro benzene oxygen base)-N-4-fluoro-Phenylpropionamide is to the regulating effect of Radix Cucumidis sativi growth
1. test method: with above-claimed cpd be made into 1 μ g/ml, 10 μ g/ml, 62.5 μ g/ml, 125 μ g/ml,
7 concentration such as 250 μ g/ml, 500 μ g/ml, 1000 μ g/ml are with the embryo of above-mentioned cucumber seeds
Root is put the 2-that places each concentration respectively, and (2,4 dichloro benzene oxygen base)-N-4-fluoro-Phenylpropionamide is molten
After dipping about 5 seconds in the liquid, be placed in the culture dish that is covered with moistening filter paper, every concentration is handled 2 wares,
4 seeds of every ware.Cover the culture dish lid, put 20 ℃ of dark culturing are put down in writing root after 7 days growth feelings
Condition.
Table 3.2-(2,4 dichloro benzene oxygen base)-N-4-fluoro-Phenylpropionamide
Influence to the cucumber lateral root growth
| Concentration of treatment (μ g/ml) | Lateral root length (cm) | Chemicals treatment lateral root knot length/blank lateral root knot length |
| ????CK | ????2.45 | ????1 |
| ????1 | ????3.85 | ????1.57 |
| ????10 | ????4.55 | ????1.86 |
| ????62.5 | ????3.45 | ????1.41 |
| ????125 | ????2.31 | ????0.94 |
| ????250 | ????1.45 | ????0.59 |
| ????500 | ????0.5 | ????0.20 |
| ????1000 | ????0.2 | ????0.08 |
2. test-results shows, compound 2-(2,4 dichloro benzene oxygen base)-N-4-fluoro-Phenylpropionamide can make when lower concentration is lower than 125 μ g/ml and promote the cucumber lateral root growth, and concentration suppresses lateral root growth at 125 μ g/ml and when above.C:2-(2,4 dichloro benzene oxygen base)-N-4-fluoro-Phenylpropionamide is grown to three kinds of crop seedlings
Regulating effect
1. test method: compound 2-(2,4 dichloro benzene oxygen base)-N-4-fluoro-Phenylpropionamide is made into 7 concentration such as 1 μ g/ml, 10 μ g/ml, 62.5 μ g/ml, 125 μ g/ml, 250 μ g/ml, 500 μ g/ml, 1000 μ g/ml.With wheat, broad bean, soybean planting spray the solution of above-mentioned each concentration in the plant surface in the plastic tub alms bowl after 10 days, and every alms bowl sprays 5ml.Observe each crop of record after 2 days to the reaction of this compound under various concentration.
2. test-results shows, when concentration at 62.5 μ g/ml and when above, broad bean shows tangible symptom of chemical damage, roll up on the blade, deformity, when spraying concentration was 1 μ g/ml, 10 μ g/ml, no symptom of chemical damage, plant strain growth were high than blank; Concentration is at 125 μ g/ml and when above, and obvious poisoning appears in soybean, and stem is from the bending of cotyledonary node place, enlargement; Concentration is 62.5 μ g/ml and when following, the obvious symptom of chemical damage of no medicine.Wheat seedling does not all have obvious poisoning under each concentration, 2-(2,4 dichloro benzene oxygen base)-N-4-fluoro-Phenylpropionamide may only have the growth regulating effect to dicotyledons as can be seen.D:2-(2,4 dichloro benzene oxygen base)-N-4-fluoro-Phenylpropionamide seed soaking cucumber seeds is emerged and
The influence of the anti-samping off of seedling
The close thorn of cucumber variety king.Above-claimed cpd is mixed with 7 concentration such as 1 μ g/ml, 10 μ g/ml, 62.5 μ g/ml, 125 μ g/ml, 250 μ g/ml, 500 μ g/ml, 1000 μ g/ml, cucumber seeds soaked about 5 seconds in each concentration respectively, every concentration is soaked 50 in seed, take out airing, be seeded in the back observation of emerging in the plastic tub alms bowl and emerge and the growth of seedling situation.
Table 4.2-(2,4 dichloro benzene oxygen base)-N-4-fluoro-Phenylpropionamide
Seed soaking cucumber seeds is emerged and seedling to the resistance against diseases of samping off
| Concentration of treatment (μ g/ml) | The number of emerging | Seedling rate (%) | The withered strain number of falling ill | Case fatality rate (%) | Surviving rate (%) | Be processed into motility rate/blank surviving rate |
| ????0(CK) | ?25 | ????50 | ????19 | ????76 | ????24 | ????1 |
| ????1 | ?26 | ????52 | ????16 | ????61.5 | ????38.5 | ????1.6 |
| ????10 | ?28 | ????56 | ????0 | ????0 | ????100 | ????4.16 |
| ????62.5 | ?23 | ????46 | ????21 | ????91.3 | ????8.7 | ????0.36 |
| ????125 | ?20 | ????40 | ????9 | ????45 | ????55 | ????2.29 |
| ????250 | ?30 | ????60 | ????20 | ????66.7 | ????33.3 | ????1.39 |
| ????500 | ?29 | ????54 | ????12 | ????41.4 | ????58.6 | ????2.44 |
| ????1000 | ?32 | ????64 | ????12 | ????37.5 | ????62.5 | ????2.6 |
Test-results shows that this compound can obviously improve the resistance of seedling to samping off.With the seed that 10 μ g/ml handle, seedling rate improves 6%, growth of seedling stalwartness, no samping off seedling.E:2-(2,4 dichloro benzene oxygen base)-N-4-fluoro-Phenylpropionamide, 2-(2-chloro-4-fluorophenoxy)-N-4-fluoro-Phenylpropionamide, 2-(2-chloro-4-fluorophenoxy)-N-3-trifluoromethyl propionic acid amide are to the preventing iron test of piemarker, lamb's-quarters, Amaranthus retroflexus, lady's-grass, dog tail weeds
Test method: the concentration of above-claimed cpd being pressed 10g/ha, 100g/ha, 200g/ha, 500g/ha, 2000g/ha, above-listed weeds were cultivated in the plastic tub alms bowl after 10 days, carry out cauline leaf and soil treatment by above-mentioned concentration, observe each crop of record two days later the reaction of this compound under various concentration.
Test-results shows: compound 2-(2-chloro-4-fluorophenoxy)-N-3-trifluoromethyl propionic acid amide reaches the A level to the weeding activity of piemarker, lamb's-quarters, Amaranthus retroflexus when consumption 500g/ha.Compound 2-(2,4 dichloro benzene oxygen base)-N-4-fluoro-Phenylpropionamide is 500g/ha at consumption, and 2-(2-chloro-4-fluorophenoxy)-N-4-fluoro-Phenylpropionamide reaches the A level to the weeding activity of piemarker, lamb's-quarters, Amaranthus retroflexus when consumption is 2000g/ha.
Biological activity test to sum up shows, 2-(2, the 4-substituent phenoxy)-N-substituted-phenyl Propionamides compound, and when the performance weeding activity, consumption is higher, and in the higher activity that shows aspect promotion plant strain growth and the promotion root growth.Especially so that 2-(2,4 dichloro benzene oxygen base)-N-4-fluorophenyl propionic acid amide activity is the highest, the 0.75-4.5g/ha that consumption only is.Therefore, this compounds is more suitable for using as plant-growth regulator.
Claims (6)
1, a kind of 2, the 4-substituted phenoxypropanamide compounds is characterized in that: its chemical structure of general formula is as follows:
Or
(calling the chemical structural formula I in the following text)
Wherein:
R
1Be H, CH
3, C
2H
5, a kind of among the i-Pr;
X is 2,4-Cl
2, 2-Cl-4-F, 2-Cl-4-CF
3In a kind of;
Y is 3-CF
3, 2,6-F
2, 2,6-i-Pr, 4-F, 3,5-F
2, 2,4-F
2In a kind of;
Z is H, 2,6-N
2, a kind of among the 3-N.
2, compound as claimed in claim 1 is characterized in that:
R
1Be H; X is 2,4-Cl
2, 2-Cl-4-F, 2-Cl-4-CF
3Y is 3-CF
3, 4-F,
3,5-F
2, 2,4-F
2, 2,6-F
2Z is H.
3, compound as claimed in claim 1 is characterized in that:
R
1Be H; X is 2,4-Cl
2, 2-Cl-4-F, 2-Cl-4-CF
3Y is H; Z is 2,6-N
2,
3-N。
4, a kind of 2, the preparation method of 4-substituting group benzene oxygen propanamide compounds is characterized in that comprising:
(1) an earlier synthetic intermediate-substituent phenoxy propionyl chloride or first synthesizing halogen propionyl replace amine;
(2) with substituent phenoxy propionyl chloride and corresponding substituting group aniline or substituted heterocycle amine in the presence of acid binding agent, in reflux temperature reaction four hours down, promptly obtain said compound.The mol ratio of substituent phenoxy propionyl chloride and corresponding substituting group aniline or substituted heterocycle amine is 1: (1-2);
Said acid binding agent is a kind of in triethylamine, yellow soda ash, salt of wormwood, potassium hydroxide, the sodium hydroxide, and its reaction formula is:
(3) the halo propionyl is replaced amine and corresponding substituting group phenol and promptly obtain said compound in reaction under the polar solvent after 8 hours, the mol ratio that the halo propionyl replaces amine and corresponding substituting group phenol is 1: (1-1.5): its reaction formula is:
5, a kind of 2, the application of 4-substituted phenoxypropanamide compounds is characterized in that with claim 1 or 2 or 3 described compounds being that acceptable carrier is formed weedicide or plant-growth regulator on effective active composition and the agronomy.
6, as claimed in claim 52, the application of 4-substituted phenoxypropanamide compounds is characterized in that with claim 2 being that the compound of general structure should use as plant-growth regulator.
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|---|---|---|---|---|
| CN105580816A (en) * | 2016-03-11 | 2016-05-18 | 李为忠 | Metamifop composition and application thereof |
| WO2016079521A1 (en) * | 2014-11-20 | 2016-05-26 | University College Cardiff Consultants Limited | Androgen receptor modulators and their use as anti-cancer agents |
| CN105660658A (en) * | 2016-03-11 | 2016-06-15 | 李为忠 | Cyhalofop-butyl composition and application thereof |
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2001
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016079521A1 (en) * | 2014-11-20 | 2016-05-26 | University College Cardiff Consultants Limited | Androgen receptor modulators and their use as anti-cancer agents |
| CN105580816A (en) * | 2016-03-11 | 2016-05-18 | 李为忠 | Metamifop composition and application thereof |
| CN105660658A (en) * | 2016-03-11 | 2016-06-15 | 李为忠 | Cyhalofop-butyl composition and application thereof |
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