CN100516052C - Alcohol amide condensed ester compound and its preparation and use - Google Patents

Alcohol amide condensed ester compound and its preparation and use Download PDF

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CN100516052C
CN100516052C CNB2006101168217A CN200610116821A CN100516052C CN 100516052 C CN100516052 C CN 100516052C CN B2006101168217 A CNB2006101168217 A CN B2006101168217A CN 200610116821 A CN200610116821 A CN 200610116821A CN 100516052 C CN100516052 C CN 100516052C
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CN1931846A (en
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吕龙
吕强
唐庆红
付群梅
王学跃
台文俊
吕沛
刘军
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Shanghai Institute of Organic Chemistry of CAS
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Abstract

The present invention is one kind of alcohol amide condensed ester compound in the structure as shown, and its preparation process and use in preparing herbicide.

Description

Alcohol amide condensed ester compound, preparation method and its usage
Technical field
What the present invention relates to is the new alcohol amide condensed ester compound of a class, preparation method and as the purposes of agricultural herbicide.
Technical background
Agricultural chemicals is the human grain that obtains, and guarantees agriculture stable yields, the indispensable production means of getting bumper crops, and in the last hundred years, agricultural chemicals such as sterilant, sterilant, weedicide etc. have been made huge contribution for human.In recent years, continuous growth along with world population, human needs to grain are also in continuous increase, but the speed of the growth of ploughing does not catch up with population growth's speed far away, solve this global problem, must rely on the grain yield that improves unit surface and improve crop quality 1 that this just must adopt various means, as breeding, cultivation, fertilising etc., and the application of agricultural chemicals also is one of requisite means wherein.But what should see is, agricultural chemicals is when making huge contribution for human civilization, because the limitation of understanding aspect, the agricultural chemicals of high poison, high residue has also brought negative impact to the environment that the mankind depend on for existence.Along with the raising of the progress of society and civilization, exploitation is efficient, low toxicity, easily degraded, security and the good environment friendly agricultural of Environmental compatibility, has become the direction of current novel pesticide initiative to replace those poor efficiencys, high poison, high residue and the high traditional agricultural chemicals of resistance.
Alcohol amide condensed ester compound is used very extensive in organic chemistry, is generally used for carboxylic acid degraded is generated the corresponding amine that replaces, and this reaction has easy and simple to handle, reaction temperature and, the yield advantages of higher.The hydroxyl amides has good nucleophilie nucleus ability, its leaving away property is also very good simultaneously, look like the condensing agent that helps that more common N-hydroxy-succinamide, N-hydroxyphthalimide etc. are used for condensation reaction, can effectively reduce reaction energy barrier, add fast response and carry out.
Alcohol amide condensed ester compound is up to the present actually rare in agricultural chemicals, medicine, is subjected to extensive attention in current research.The strobilurin series bactericidal agent pyraclostrobin of BASF is exactly a class hydroxyl amides of developing on original methoxy acrylate basis.
People such as Lv Long are the synthetic class alcohol amide condensed ester compound of report this time, is used for agricultural herbicide and does not see the pertinent literature report.
Summary of the invention
The object of the invention provides a kind of alcohol amide condensed ester compound.
The object of the invention also provides a kind of preparation method of above-claimed cpd.
Another object of the present invention provides a kind of purposes of above-claimed cpd.
The structural formula of a kind of alcohol amide condensed ester compound provided by the invention is shown in (I):
Figure C20061011682100051
Wherein: R 1, R 4=hydrogen, hydroxyl, sulfydryl, nitro, halogen, C 1-C 8Alkyl, C 1-C 8Alkoxyl group, phenoxy group, benzene sulfydryl, heterocyclic radical, substituted heterocyclyloxy or substituted heterocycle sulfydryl; R 2=hydrogen, C 1-C 8Alkyl, phenyl, substituted-phenyl, R 3=hydrogen, C 1-C 8Alkyl, C 1-C 8Alkoxyl group, C 1-C 8Alkylamino, phenyl or substituted-phenyl.Wherein above-mentioned substituting group is halogen, C 1-C 8Alkyl or C 1-C 8Alkoxyl group etc.Described heterocyclic radical is pyridyl, thienyl, thiazolyl or pyrimidyl.
Compound of the present invention has following general structure:
R in the formula 1, R 2, R 3As previously mentioned.
Below, typical compound involved in the present invention is listed in table one.
Figure C20061011682100061
Figure C20061011682100081
Figure C20061011682100091
Alcohol amide condensed ester compound involved in the present invention can be synthetic with following reactions steps:
Figure C20061011682100111
R in the above-mentioned reaction formula 1, R 2, R 3The substituting group of representative as previously mentioned.
The synthetic R that passes through of intermediate (II) 3Substituted formyl chlorine and N-R 2Replace oxyammonia prepared in reaction under alkaline condition, described R 3Substituted formyl chlorine, N-R 2The mol ratio that replaces oxyammonia and alkali is 1: 1-10: 1-10.Solvent can be water; Varsols such as benzene, toluene or dimethylbenzene; Halogenated hydrocarbon solvents such as methylene dichloride, ethylene dichloride or chloroform; Ether solvent such as tetrahydrofuran (THF) or dioxane; Ketones solvent such as acetone or methyl iso-butyl ketone (MIBK); Alcoholic solvents such as methyl alcohol, ethanol or Virahol; Also can use the mixture of dimethyl formamide, methyl-sulphoxide, acetonitrile and above-mentioned solvent, the optimum solvent of this reaction is water and ether solvent mixture.Temperature of reaction be room temperature to solvent boiling point, the reaction times is 0.5 to 72 hour.In this step reaction, used alkali can be hydride, alcoxyl metallic compound or its carbonate of the organic amine compound, monovalence or the divalent metal that contain lone-pair electron, as sodium hydride, potassium hydride KH, hydrolith; Sodium methylate or sodium ethylate, potassium methylate or potassium ethylate; Yellow soda ash, salt of wormwood or lime carbonate etc. also can be triethylamine, pyridine, N, and N-dimethyl aminopyridine (DMAP), diisopropyl ethyl amine etc. contain the organic amine compound of lone-pair electron.
The synthetic of compound (I) can pass through R 1, R 4Substituted benzoyl chloride and intermediate (II) prepared in reaction under alkaline condition, described R 1, R 4The mol ratio of substituted benzoyl chloride, intermediate (II) and alkali is 1: 0.1-10: 1-10.Solvent can be water; Varsols such as benzene, toluene or dimethylbenzene; Halogenated hydrocarbon solvents such as methylene dichloride, ethylene dichloride or chloroform; Ether solvent such as tetrahydrofuran (THF) or dioxane; Ketones solvent such as acetone or methyl iso-butyl ketone (MIBK); Alcoholic solvents such as methyl alcohol, ethanol or Virahol; Also can use the mixture of dimethyl formamide, methyl-sulphoxide, acetonitrile and above-mentioned solvent, the optimum solvent of this reaction is water and ether solvent mixture.Temperature of reaction be room temperature to solvent boiling point, the reaction times is 0.5 to 72 hour.In this step reaction, used alkali can be hydride, alcoxyl metallic compound or its carbonate of the organic amine compound, monovalence or the divalent metal that contain lone-pair electron, as sodium hydride, potassium hydride KH, hydrolith; Sodium methylate or sodium ethylate, potassium methylate or potassium ethylate; Yellow soda ash, salt of wormwood or lime carbonate etc. also can be triethylamine, pyridine, N, and N-dimethyl aminopyridine (DMAP), diisopropyl ethyl amine etc. contain the organic amine compound of lone-pair electron.
The synthetic of compound (I) also can pass through R 1Replace formic acid and intermediate (II) prepared in reaction under condensing agent and catalyzer alkali existence condition, described R 1The mol ratio that replaces formic acid, intermediate (II), condensing agent and alkali is 1: 0.1-10: 0.1-10: 0.1-10.In this step reaction, used condensing agent can be N, N-dicyclohexylcarbodiimide (DCC), N, N '-DIC (DIC), N, N '-carbonyl dimidazoles (CDI), benzotriazole-1-base-oxygen base tripyrrole alkyl phosphorus phosphorus hexafluoride salt (PyBOP), O-(7-azepine benzo triazol-1-yl) oxygen base-N, N, N ', N '-tetramethyl-urea phosphorus hexafluoride salt (TATU), O-benzotriazole-N, N, N ', N '-tetramethyl-urea tetrafluoride boron salt (TBTU) or benzotriazole-1-base-oxygen base three dimethylamino phosphorus phosphorus hexafluoride salt (BOP) etc.; Solvent can be water; Varsols such as benzene, toluene or dimethylbenzene; Halogenated hydrocarbon solvents such as methylene dichloride, ethylene dichloride or chloroform; Ether solvent such as tetrahydrofuran (THF) or dioxane; Ketones solvent such as acetone or methyl iso-butyl ketone (MIBK); Alcoholic solvents such as methyl alcohol, ethanol or Virahol; Also can use the mixture of dimethyl formamide, methyl-sulphoxide, acetonitrile and above-mentioned solvent, the optimum solvent of this reaction is a methylene dichloride.Temperature of reaction be room temperature to solvent boiling point, the reaction times is 0.5 to 72 hour.In this step reaction, catalyst system therefor can be hydride, alcoxyl metallic compound or its carbonate of the organic amine compound, monovalence or the divalent metal that contain lone-pair electron, as sodium hydride, potassium hydride KH, hydrolith; Sodium methylate or sodium ethylate, potassium methylate or potassium ethylate; Yellow soda ash, salt of wormwood or lime carbonate etc. also can be triethylamine, pyridine, N, and N-dimethyl aminopyridine (DMAP), diisopropyl ethyl amine etc. contain the organic amine compound of lone-pair electron.
The invention provides the purposes of above-mentioned alcohol amide condensed ester compound, promptly can be used for agricultural herbicide.
With the active constituent of compound of the present invention as agricultural herbicide, be mixed with various liquors, missible oil, suspension concentrate, propellant, pulvis, wettable powder, soluble powder, kill reptile aerosol, fumicants, poison bait, sustained release dosage (promptly comprising medicine pen, ointment, coating, microcapsule), (water dispersible) granule or capsule etc., can be used for the control of sanitary insect pests such as cockroach, ant.
The weight percentage of active constituent is recommended as 5 ~ 90% in the preparation, and all the other are carrier, and carrier comprises two kinds at least, and wherein at least a is tensio-active agent.Carrier can be solid or liquid.Suitable solid carrier comprises natural or synthetic clay and silicate, for example natural silica and diatomite; Magnesium Silicate q-agent is talcum for example; Magnesium aluminum silicate is kaolinite, kaolin, polynite and mica for example; White carbon black, lime carbonate, light calcium carbonate; Calcium sulfate; Wingdale; Sodium sulfate; Amine salt such as ammonium sulfate, hexamethylene diamine.Liquid vehicle comprises water and organic solvent, and when water was cooked solvent or thinner, organic solvent also can be used as auxiliary or antifreeze additive.Appropriate organic solvent comprises aromatic hydrocarbons for example benzene, dimethylbenzene, toluene etc.; Hydrochloric ether, for example chlorinated benzene, vinylchlorid, trichloromethane, methylene dichloride etc.; Aliphatic hydrocarbon, for example petroleum fractions, hexanaphthene, light mineral oil; Alcohols, for example Virahol, butanols, ethylene glycol, glycerol and hexalin etc.; And their ether and ester; Also have ketone, for example acetone, pimelinketone and dimethyl amine and N-methyl-pyrrolidone.
Tensio-active agent can be emulsifying agent, dispersion agent or wetting agent; Can be ionic or non-ionic type.Nonionic emulsifier is polyoxyethylene fatty acid fat, polyoxyethylene aliphatic alcohol ether, polyoxyethylene fatty amine for example, and commercially available emulsifying agent: agricultural newborn 2201B, agricultural newborn 0203B, farming breast 100 #, farming breast 500 #, farming breast 600 #, agricultural newborn 600-2 #, farming breast 1601, farming breast 2201, agricultural newborn NP-10, agricultural newborn NP-15, farming breast 507 #, agricultural newborn OX-635, agricultural newborn OX-622, agricultural newborn OX-653, agricultural newborn OX-667, peaceful breast 36 #Dispersion agent comprises sodium lignosulfonate, draws back powder, calcium lignin sulphonate, condensation compound of methyl naphthalene sulfonic acid and formaldehyde etc.Wetting agent is: sodium laurylsulfate, Sodium dodecylbenzene sulfonate, sodium alkyl naphthalene sulfonate etc.
These preparations can be prepared by method in common.For example, active substance is mixed with liquid solvent and/or solid carrier, add tensio-active agent such as emulsifying agent, dispersion agent, stablizer, wetting agent simultaneously, can also add other auxiliary agent as tackiness agent, defoamer, oxygenant etc.
Structural formula provided by the present invention is the compound of (I), simple synthetic method not only, and have weeding activity and crop-selective, can be used for weedicide.Its preparation can be prevented and treated most of farmland weeds effectively, effectively prevent and treat responsive Gramineae down than low dosage, broadleaf weeds and nutgrass flatsedge, concrete controlling object comprises barnyard grass grass (Echinochloacrusgalli), lady's-grass (Digitaria sanguinalis), Herba Eleusines Indicae (Eleusine indica), Herba Setariae Viridis (Setariaviridis), annual bluegrass (Poa annua), wild avena sativa (Avena fatua), amur foxtail (Alopecurus aequalis), Japan amur foxtail (Alopecurus japonicus), Amaranthus retroflexus (Amaranthus retroflexus), thorn amaranth (Amaranthusspinosus), lamb's-quarters (Chenopodium album), leaf mustard (Brassica juncea), purslane (Portulacaoleracea), Herba Acalyphae (Acalypha australis), Herba Cyperi Difformis (Cyperus difformis), Semen Euphorbiae (Leptochloachinensis), Rhizoma Cyperi (Cyperus rotundus), grass (Fimbristylis miliacea) floats sunshine, chickweed (Stallaria media), Stellaria alsine Grim. (Stellaria alsine), Herba Erigerontis Annui (Erigeron annuus), short arrowhead (Sagittariasagittifolia), Herba seu Flos Convolvuli arvensis (Convolvulus arvensis) etc.
Embodiment:
Put up with part embodiment below and provide the required analytical data of detailed reaction conditions, purification process, physical constant and structural confirmation, it is to be noted that the present invention not merely is confined in the scope of following embodiment.
Embodiment 1
Synthesizing of intermediate (II):
With N-methyl benzoyl azanol (R 2=Me, R 3=Ph) be example
N-methyl hydroxylamine hydrochloride (1.05g, 15mmol), potassium hydroxide (0.84g, 15mmol), yellow soda ash (0.848g; 8mmol) be dissolved in the 20ml water; add the 20ml ether, be cooled to 0 ℃, slowly drip Benzoyl chloride (1.4g; 10mmol) dropwise; continue reaction 1 hour, filter, washing; dry N-methyl benzoyl azanol 1.2g, yield 80%.
Embodiment 2
I-1's is synthetic:
Method I
(4,6-dimethoxy-2-pyrimidine sulfydryl)-(326mg 1mmol) is dissolved in the 20ml methylene dichloride to the 6-chloro-benzoic acid to 2-; 0 ℃ slowly drips 1N N; N-dicyclohexylcarbodiimide (DCC) dichloromethane solution 1.1ml waits to dropwise, and adds DMAP (30mg), benzoyl azanol (137mg; 1mmol); rise again and continue to react 24 hours to room temperature, filter, filtrate is spin-dried for; column chromatography gets the 369mg product, yield 83%.
Embodiment 3
I-17's is synthetic:
Method II
2, (154mg 1mmol) is dissolved in the 20ml methylene dichloride to the 6-resorcylic acid, and 0 ℃ slowly adds POCl 35ml waits to dropwise, and solvent is spin-dried for, add the benzoyl azanol (411mg, 3mmol) and triethylamine (111mg 1.1mmol), rises again to room temperature and continues reaction 24 hours, filters, and filtrate is spin-dried for, and column chromatography gets the 164mg product, yield 60.1%.
Embodiment 4
I-20's is synthetic:
Method III
2; (326mg 1mmol) is dissolved in the 20ml methylene dichloride to 6-resorcylic acid-4-fluorobenzoyl azanol condensation ester I-17, and 0 ℃ slowly drips 1N DCC dichloromethane solution 1.1ml; wait to dropwise; (137mg 1mmol), rises again and continues to react 24 hours to room temperature for adding DMAP (30mg), benzoyl azanol; filter; filtrate is spin-dried for, and column chromatography gets the 369mg product, yield 83%.
Reaction product is dissolved in 20ml N, dinethylformamide (DMF), add salt of wormwood (251mg, 1.8mmol) and 4,6-dimethoxy-2-a few minutes and pyrimidine (361mg, 1.66mmol), be warming up to 80 ℃ of reactions 2 hours, reduce to room temperature, reaction solution is poured in the frozen water, the washing of ethyl acetate extraction, organic phase, dry, be spin-dried for, column chromatography gets I-20 280mg.
Other compounds are synthetic synthetic with reference to embodiment 1-4 synthetic method.
Below be the synthetic compound characterization data:
SIOC-H-001
1HNMR(CDCl 3)(ppm)：9.81(1H，S)，7.87(2H，d)，7.69(1H，d)，7.45-7.60(5H，m)，5.74(1H，s)，3.73(6H，s)
MS-ESI(m/e)：525.80
HPLC 96.0％
m.p.180-183℃
I-003
1HNMR(CDCl 3)(ppm)：7.61(2H，t)，7.51(2H，m)，7.21-7.30(3H，m)，5.79(2H，s)，3.83(12H，s)，2.37(3H，s)
MS-ESI(m/e)：564.1
HPLC 96.4％
m.p.129-132℃
I-004
1HNMR(CDCl 3)(ppm)：7.82(2H，d)，7.78(2H，d)，7.68(1H，t)，7.43(2H，d)，7.39(1H，s)，7.16-7.19(1H，m)，6.00(1H，s)，3.81(3H，s)，3.69(6H，s)
MS-ESI(m/e)：476.05
HPLC 97.4％
M.p. oily
I-005
1HNMR(CDCl 3)(ppm)：9.76(1H，s)，7.76(2H，d)，7.67(1H，d)，7.48-7.56(2H，m)，7.25-7.48(2H，m)，5.73(1H，s)，3.72(6H，s)，3.72(3H，s)
MS-ESI(m/e)：460.10
HPLC 96.4％
m.p.167-169℃
I-006
1HNMR(CDCl 3)(ppm)：9.61(1H，s)，7.24(2H，t)，7.61(1H，t)，7.51(1H，t)7.39(2H，t)，7.24(2H，t)，5.78(2H，s)，3.82(12H，s)
MS-ESI(m/e)：572.25
HPLC 94.7％
m.p.62-64℃
I-007
1HNMR(CDCl 3)(ppm)：9.66(1H，s)，7.60-7.65(2H，m)，7.47(1H，t)，7.32-7.38(3H，m)，7.22-7.26(1H，m)，5.80(1H，s)，3.83(6H，s)，2.40(3H，s)
MS-ESI(m/e)：444.35
HPLC 91.7％
m.p.oil
I-008
1HNMR(CDCl 3)(ppm)：9.81(1H，s)，7.97(2H，d)，7.67-7.75(3H，m)，7.47-7.57(2H，m)，5.74(1H，s)，5.72(6H，s)
MS-ESI(m/e)：514.10
HPLC 89.6％
m.p.177-178℃
I-009
1HNMR(CDCl 3)(ppm)：9.74(1H，s)，7.87-7.91(2H，m)，7.68(1H，d)，7.46-7.57(2H，m)，7.15(2H，t)，5.74(1H，s)，3.72(6H，s)
MS-ESI(m/e)：463.90
HPLC 95.0％
m.p.160-162℃
I-010
1HNMR(CDCl 3)(ppm)：9.65(1H，s)，7.83(2H，d)，7.45-7.56(2H，m)，7.95(2H，d)，5.73(1H，s)，3.87(3H，s)，3.72(6H，s)
MS-ESI(m/e)：477.55
HPLC 95.6％
m.p.139.5-142℃
I-011
1HNMR(CDCl 3)(ppm)：9.84(1H，s)，7.27-7.70(6H，m)，7.25-7.27(1H，m)，5.74(1H，s)，5.73(1H，s)，3.72(6H，s)
MS-ESI(m/e)：464.0
HPLC 90.5％
m.p.169-171℃
I-012
1HNMR(CDCl 3)(ppm)：9.73(1H，s)，7.85(1H，s)，7.67-7.74(2H，m)，7.38-7.56(4H，m)，5.73(1H，s)，3.72(6H，s)
MS-ESI(m/e)：481.35
HPLC 99.4％
m.p.40-41.5℃
I-013
1HNMR(CDCl 3)(ppm)：9.76(1H，s)，7.67(1H，d)，7.47-7.55(4H，m)，7.19(1H，s)，3.72(6H，s)，2.35(6H，s)
MS-ESI(m/e)：474.00
HPLC 94.8％
m.p.67-70℃
I-014
1HNMR(CDCl 3)(ppm)：9.47(1H，s)，7.57-7.64(3H，m)，7.18-7.26(4H，m)，5.78(2H，s)，3.82(12H，s)，2.38(3H，s)
MS-ESI(m/e)：564.35
HPLC 99.6％
m.p.158-160℃
I-015
1HNMR(CDCl 3)(ppm)：7.73(1H，t)，7.21-7.45(5H，m)，7.13(1H，d)，6.00(2H，s)，33.8(2H，s)，3.76(2H，s)
MS-ESI(m/e)：556.55
HPLC 90.7％
m.p.59-61℃
I-020
1HNMR(CDCl 3)(ppm)：9.50(1H，s)，7.58-7.74(3H，m)，7.23(2H，t)，7.10(2H，t)，5.78(2H，s)，3.81(12H，s)
MS-ESI(m/e)：568.30
HPLC 99.3％
m.p.153-155℃
I-021
1HNMR(CDCl 3)(ppm)：9.57(1H，s)，7.63(1H，t)，7.54(1H，d)，7.36(2H，m)，7.22-7.32(3H，m)，5.78(2H，s)，3.83(12H，s)
MS-ESI(m/e)：584.40
HPLC 93.9％
m.p.58-60℃
I-022
1HNMR(CDCl 3)(ppm)：9.47(1H，s)，7.61(1H，t)，7.21-7.29(4H，m)，7.13(1H，s)，5.78(2H，s)，3.82(12H，s)，2.31(6H，s)
MS-ESI(m/e)：578.50
HPLC 96.8％
m.p.137-139℃
I-023
1HNMR(CDCl 3)(ppm)：7.71-7.74(3H，m)，7.48(1H，d)，7.42(1H，d)，7.31(2H，d)，6.03(1H，s)，3.78(6H，s)，2.37(3H，s)
MS-ESI(m/e)：444.0
HPLC 99.6％
m.p.165-166℃
I-024
1HNMR(CDCl 3)(ppm)：7.47(1H，t)，7.25-7.44(4H，m)，7.25(1H，d)，7.08(1H，dd)，5.80(1H，s)，3.84(3H，s)，3.83(6H，s)
MS-ESI(m/e)：460
HPLC 96.9％
m.p.oil
Si℃-H-025
1HNMR(CDCl 3)(ppm)：7.64-7.74(3H，m)，5.83(1H，s)，5.55(1H，d)，3.62(6H，s)，3.27(2H，m)，1.4-1.8(1H，m)，0.98-1.26(10H，m)
MS-ESI(m/e)：449.5
HPLC 96.1％
m.p.170-172℃
I-026
1HNMR(CDCl 3)(ppm)：9.53(1H，s)，7.62(1H，t)，7.37-7.47(3H，m)，7.19-7.26(3H，m)，5.78(2H，s)，3.82(12H，s)
MS-ESI(m/e)：568.35
HPLC 98.6％
m.p.75-78℃
1HNMR(CDCl 3)(ppm)：9.52(1H，s)，7.57-7.64(3H，m)，7.41(2H，d)，7.21-7.24(2H，m)，5.78(2H，s)，3.82(12H，s)
MS-ESI(m/e)：618.35
HPLC 98.7％
m.p.183-185℃
I-029
1HNMR(CDCl 3)(ppm)：9.62(1H，s)，7.60-7.65(3H，m)，7.37(2H，d)，7.22(2H，t)，5.79(2H，s)，3.83(12H，s)
MS-ESI(m/e)：584.20
HPLC 92.4％
m.p.150-153℃
I-031
1HNMR(CDCl 3)(ppm)：9.841(H，s)，7.99(1H，t)，7.62(1H，t)，7.45(1H，m)，7.21-7.26(2H，m)，7.06-7.13(1H，m)，5.782(H，s)，3.821(2H，s)
MS-ESI(m/e)：568.25
HPLC 97.9％
m.p.116-118℃
I-032
1HNMR(CDCl 3)(ppm)：8.04(2H，d)，7.82(2H，d)，7.63(1H，t)，7.50(1H，d)，7.35(1H，d)，5.94(1H，s)，3.80(6H，s)
MS-ESI(m/e)：498
HPLC 90％
m.p.174-177℃
I-033
1HNMR(CDCl 3)(ppm)：7.87(2H，t)，7.48(1H，t)7.37(1H，d)，7.24(1H，d)，7.13(2H，t)，5.81(1H，s)，3.83(6H，s)
MS-ESI(m/e)：448.10
HPLC 92.4％
m.p.136-138℃
I-034
1HNMR(CDCl 3)(ppm)：9.76(1H，s)，7.81(2H，d)，7.47(1H，t)，7.44(1H，d)，7.25(1H，d)，6.93(2H，d)，5.81(1H，s)，3.86(3H，s)，3.83(6H，s)
MS-ESI(m/e)：460
HPLC 94.8％
m.p.118-120℃
I-036
1HNMR(CDCl 3)(ppm)：8.09(1H，t)，7.41-7.51(2H，m)，7.40(1H，t)，7.14-7.29(3H，m)，5.81(1H，s)，3.84(6H，s)
MS-ESI(m/e)：448
m.p.134-135℃
I-037
1HNMR(CDCl 3)(ppm)：7.36-7.46(5H，m)，7.18(1H，s)，5.83(1H，s)，3.86(6H，s)，2.35(6H，s)MS-ESI (m/e)：458.1
HPLC 98.8％
m.p.150-151℃
I-038
1HNMR(CDCl 3)(ppm)：8.12(1H，t)，7.69(1H，t)，7.49-7.56(3H，m)，7.30(1H，t)，7.15(1H，dd)，5.74(1H，s)，3.74(6H，s)
MS-ESI(m/e)：464
HPLC 95.3％
M.p. oily
I-039
1HNMR(CDCl 3)(ppm)：7.58(1H，t)，7.37-7.41(4H，m)，7.19(2H，m)，5.73(1H，t)，3.69(6H，s)，3.49(3H，s)
MS-ESI(m/e)：474
HPLC 98.8％
m.p.116-117℃
I-040
1HNMR(CDCl 3)(ppm)：7.37-7.43(3H，m)，7.18-7.25(4H，m)，5.82(1H，s)，7.30(1H，t)，3.81(6H，s)，3.38(3H，s)，2.33(3H，s)
MS-ESI(m/e)：458
HPLC 98.8％
M.p. oily
I-041
1HNMR(CDCl 3)(ppm)：7.58-7.62(3H，m)，7.40-7.43(2H，m)，6.83(2H，d)，5.73(1H，s)，5.81(3H，s)，3.70(6H，s)，3.48(3H，s)
MS-ESI(m/e)：490
HPLC 99.6％
m.p.124-126℃
I-042
1HNMR(CDCl 3)(ppm)：7.57-7.65(3H，m)，7.43(2H，d)，7.00(2H，t)，5.73(1H，s)，5.74(3H，s)，3.70(6H，s)，3.51(3H，s)
MS-ESI(m/e)：478
HPLC 99.1％
m.p.110-113℃
I-044
1HNMR(CDCl 3)(ppm)：7.50-7.60(3H，m)，7.15(2H，d)，6.95(2H，t)，5.73(1H，s)，5.80(2H，s)，3.80(12H，s)，3.17(3H，s)
MS-ESI(m/e)：582
HPLC 99.0％
m.p.152-154℃
I-045
1HNMR(CDCl 3)(ppm)：7.61(2H，d)，7.41(1H，t)，7.22(2H，m)，6.85(2H，d)，5.81(1H，s)，3.80(9H，s)，3.37(3H，s)
MS-ESI(m/e)：474
HPLC 96.67％
m.p.158-159℃
I-048
1HNMR(CDCl 3)(ppm)：7.60(1H，t)，7.22(2H，d)，5.79(2H，s)，3.81(12H，s)，3.03(3H，s)，2.17(2H，m)，1.01(3H，t)
MS-ESI(m/e)：538
HPLC 99.28％
m.p.104-107℃
I-049
1HNMR(CDCl 3)(ppm)：7.61(1H，t)，7.24(2H，d)，5.80(2H，s)，3.81(12H，s)，3.03(3H，s)，1.95(3H，s)
MS-ESI(m/e)：502
HPLC 96.02％
m.p.122-124℃
I-050
1HNMR(CDCl 3)(ppm)：7.48(1H，t)，7.27-7.37(2H，m)，5.82(1H，s)，3.82(6H，s)，3.32(3H，s)，2.12(3H，s)
MS-ESI(m/e)：382.1
HPLC 93.96％
m.p.101-103℃
I-051
7.51(1H，t)，7.27-7.37(2H，m)，5.82(1H，s)，3.82(6H，s)，3.32(3H，s)，2.37(2H，m)，1.08(3H，t)
MS-ESI(m/e)：396.3
HPLC 96.50％
m.p.78-80℃
I-052
1HNMR(CDCl 3)(ppm)：7.50(1H，t)，7.35(1H，d)，7.26(1H，d)，5.82(1H，s)，3.82(6H，s)，3.32(3H，s)，2.81(1H，m)，1.07(6H，d)
MS-ESI(m/e)：410.2
HPLC 97.12％
m.p.65-68℃
I-053
1HNMR(CDCl 3)(ppm)：7.50-7.56(3H，m)，7.14(2H，d)，6.77(2H，d)，5.78(2H，s)，3.78(15H，s)，3.12(3H，s)
MS-ESI(m/e)：616
HPLC 99.92％
m.p.132-133℃
I-054
1HNMR(CDCl 3)(ppm)：7.62(1H，t)，7.23(2H，d)，5.79(2H，d)，3.80(12H，s)，3.06(3H，s)，1.09(9H，s)
MS-ESI(m/e)：558.2
HPLC 97.86％
m.p.129-133℃
I-055
1HNMR(CDCl 3)(ppm)：7.52(1H，t)，7.29-7.34(2H，m)，7.13(4H，d)，5.79(2H，s)，3.79(12H，s)，3.12(3H，s)，2.31(3H，s)
MS-ESI(m/e)：578.2
HPLC 94.63％
m.p.103-105℃
I-056
1HNMR(CDCl 3)(ppm)：7.69(1H，d)，7.48-7.57(2H，m)，5.74(1H，s)，3.71(6H，s)，3.38(3H，s)，2.88(1H，m)，1.03(6H，d)
MS-ESI(m/e)：426.1
HPLC 98.21％
m.p.63-64℃
I-057
1HNMR(CDCl 3)(ppm)：7.69(1H，d)，7.51-7.57(2H，m)，5.74(1H，s)，3.71(6H，s)，3.38(3H，s)，2.34(2H，m)，1.05(3H，t)
MS-ESI(m/e)：412.0
HPLC 96.69％
m.p.62-68℃
I-058
1HNMR(CDCl 3)(ppm)：7.69(1H，d)，7.48-7.57(2H，m)，5.74(1H，s)，3.71(6H，s)，3.37(3H，s)，2.10(3H，s)
MS-ESI(m/e)：398
HPLC 99.55％
m.p.127-130℃
I-059
1HNMR(CDCl 3)(ppm)：7.62(1H，t)，7.22(2H，d)，5.79(2H，s)，3.80(12H，s)，3.02(3H，s)，2.51(1H，m)，0.94(6H，d)
MS-ESI(m/e)：552.2
HPLC 97.18％
m.p.130-132℃
I-060
1HNMR(CDCl 3)(ppm)：7.51(1H，t)，7.38(1H，d)，7.26(1H，d)，5.81(1H，s)，3.80(6H，s)，3.30(3H，s)，1.17(9H，s)
MS-ESI(m/e)：424.1
HPLC 98.28％
m.p.82-84℃
I-062
1HNMR(CDCl 3)(ppm)：7.52(2H，d)，7.40(1H，t)，7.25(2H，t)，7.16(3H，t)，5.82(1H，s)，3.81(6H，s)，3.38(3H，s)，2.34(3H，s)
MS-ESI(m/e)：458.3
HPLC 98.41％
M.p. oily
I-065
1HNMR(CDCl 3)(ppm)：7.26-7.57(7H，m)，5.74(1H，s)，3.69(6H，s)，3.51(3H，s)MS-ESI(m/e)：494.1
HPLC 95.41％
m.p.118-120℃
I-066
1HNMR(CDCl 3)(ppm)：7.17-7.43(7H，m)，5.83(1H，s)，3.81(6H，s)，3.42(3H，s)MS-ESI(m/e)：478.1
HPLC 98.70％
m.p.75-76℃
I-067
1HNMR(CDCl 3)(ppm)：7.52(1H，t)，7.09-7.31(6H，m)，5.80(2H，s)，3.80(12H，s)，3.36(3H，s)，3.17(3H，s)
MS-ESI(m/e)：620.2
HPLC 98.77％
m.p.64-65℃
I-068
1HNMR(CDCl 3)(ppm)：8.25(2H，d)，7.78(2H，d)，7.42(1H，t)，7.21-7.27(2H，m)，5.84(1H，s)，3.84(6H，s)，3.47(3H，s)
MS-ESI(m/e)：489.0
HPLC 96.41％
m.p.109-111℃
I-069
1HNMR(CDCl 3)(ppm)：8.19(2H，d)，7.71(2H，d)，7.50(1H，t)，5.80(2H，s)，3.81(12H，s)，3.20(3H，s)
MS-ESI(m/e)：609.0
HPLC 96.19％
m.p.202-203℃
I-070
MS-ESI(m/e)：443.80
HPLC 96.9％
I-071
MS-ESI(m/e)：458
HPLC 95.4％
I-072
MS-ESI(m/e)：484.4
HPLC 87％
I-073
MS-ESI(m/e)：98
HPLC 95.2％
I-074
MS-ESI(m/e)：512
HPLC 98.3％
I-075
MS-ESI(m/e)：514
HPLC 96.7％
I-076
MS-ESI(m/e)：540
HPLC 96.7％
I-077
MS-ESI(m/e)：498
HPLC 95.5％
I-078
MS-ESI(m/e)：514
HPLC 96.0％
I-080
MS-ESI(m/e)：517
HPLC 96.7％
I-080
MS-ESI(m/e)：517
HPLC 98.7％
I-081
MS-ESI(m/e)：517
HPLC 99.2％
I-082
I-083
MS-ESI(m/e)：514
HPLC 98.1％
I-084
MS-ESI(m/e)：502
HPLC 98.6％
I-085
MS-ESI(m/e)：552
HPLC 98.1％
I-086
MS-ESI(m/e)：502
HPLC 98.1％
I-087
MS-ESI(m/e)：563
HPLC 99.1％
I-088
MS-ESI(m/e)：498
HPLC 95.5％
I-089
MS-ESI(m/e)：494
HPLC 95.3％
I-090
MS-ESI(m/e)：509
HPLC 95.8％
I-091
MS-ESI(m/e)：461
HPLC 98.7％
I-092
MS-ESI(m/e)：525
HPLC 98.8％
I-093
MS-ESI(m/e)：461
HPLC 95.0％
I-094
MS-ESI(m/e)：522.9
HPLC 95.8％
I-095
MS-ESI(m/e)：432
HPLC 95.8％
I-096
MS-ESI(m/e)：474
HPLC 96.8％
I-097
MS-ESI(m/e)：509
HPLC 99.4％
I-098
MS-ESI(m/e)：509
HPLC 97.4％
I-099
MS-ESI(m/e)：529
HPLC 96.6％
I-100
MS-ESI(m/e)：529
HPLC 96.9％
I-101
MS-ESI(m/e)：529
HPLC 98.7％
I-102
MS-ESI(m/e)：540
HPLC 99.0％
I-103
MS-ESI(m/e)：525
HPLC 98.5％
I-104
MS-ESI(m/e)：513
HPLC 98.9％
I-105
MS-ESI(m/e)：563
HPLC 95.4％
I-106
MS-ESI(m/e)：513
HPLC 98.9％
I-107
MS-ESI(m/e)：574
HPLC 99.0％
I-108
MS-ESI(m/e)：509
HPLC 99.7％
I-109
MS-ESI(m/e)：418
HPLC 93.0％
Following examples 5 to example 9 provides with compound of the present invention as the active substance component, and the concrete instance of processing preparation several herbicides formulation it is to be noted that the present invention not merely is confined in the scope of following example.
Embodiment 5
Wettable powder (WP) prescription: the compound with 15% (I-1) (table one), 5% sulfonated lignin (M q), 1% ethoxylated dodecyl alcohol (JFC), 40% diatomite and 44% light calcium carbonate mix equably, pulverizes, and promptly gets wettable powder.
Embodiment 6
Missible oil (EC) prescription: No. 602, the compound with 10% (I-1) (table one), 5% farming breast No. 500 (calcium salts), 5% farming breast, 5% N-N-methyl-2-2-pyrrolidone N-and 75% dimethylbenzene heated and stirred are even, promptly get 10% missible oil.
Embodiment 7
Granule (GR) prescription: the compound with 5% (I-1) (table one), 1% polyvinyl alcohol (PVA), 4% naphthalenesulfonic acid-formaldehyde condensate (NMO) and 90% clay mix equably; pulverize; add 20 parts of water to these 100 parts of mixtures then; mediate; with the extruding granulator; make 14-32 purpose particle, drying promptly gets 5% granule.
Embodiment 8
Aqueous emulsion (EW) prescription: the compound with 15% (I-1) (table one), 8% alkylaryl formaldehyde resin Soxylat A 25-7,10% calcium dodecylbenzene sulphonate, 3% tetradecanol, 10% dimethyl formamide, 5% propylene glycol, surplus is a water, according to each constitutive property, make oil phase and water respectively, then under high-speed stirring, the two is mixed, form 15% aqueous emulsion of favorable dispersity.
Embodiment 9
Water suspending agent (SC) prescription: the compound with 15% (I-1) (table one), 5% calcium lignin sulphonate, 0.5% white carbon black, 4% ethylene glycol, 1% defoamer, surplus are water, in the adding sand milling still, are ground to certain fineness, make 15% suspension agent.
Embodiment 10
Biological activity determination:
Following examples provide uses compound of the present invention to carry out the example of biological activity determination, it is to be noted that the present invention not merely is confined in the scope of following example.
The weeding activity evaluation test is carried out according to following method:
Test is the sandy loam of preparation with soil, and the weeding activity test is 9.5cm with basin alms bowl diameter, and safety testing is 12.0cm with basin alms bowl diameter.
The basin alms bowl that test is handled before the bud carries out the soil surface spraying one day after in sowing to be handled, the soup of handling is compound acetone, N, dinethylformamide organic solvent dissolutions such as (DMF), and add the laboratory preparation of 0.5% tween-80, thin up is needs dosage again.
The basin alms bowl that test is handled behind the bud was after planting put into hot-house culture after 7～9 days, carrying out foliar spray handles, the soup of handling is organic solvent dissolutions such as compound acetone, DMF, and adds the laboratory preparation of 0.5% tween-80, and thin up is needs dosage again.
The compound treatment concentration of active determination test is 30g ai/ha or 60g ai/ha, after the basin alms bowl of processing leaves standstill 1 day, puts into the greenhouse, regularly waters the weeding activity of appearance method observed and recorded compound after 14～21 days.
With the weeding activity of hazard of plant symptom (inhibition, deformity, yellow, albefaction) performance degree range estimation compound, 0 expression does not have herbicidal effect or to crop safety, weeds or crop are killed in 100% expression fully.
Weeding activity and crop safety appearance method judgement criteria are as follows:
Phytotoxicity (%) Weeding activity comment (inhibition, deformity, albefaction etc.) Crop safety comment (inhibition, deformity, albefaction etc.)
0 With contrast, anti-, eliminate With contrast, anti-, normal
10-20 Gently, influential slightly, eliminate Gently, influential slightly, can consider
30-40 Gently, influential, eliminate Sensitivity, influential, eliminate
50-60 Sensitivity, influential, can consider further transformation Responsive, poisoning is heavy, eliminates
70-80 Responsive, can consider Extremely responsive, poisoning is heavy, eliminates
90-100 Extremely responsive, good Extremely responsive, poisoning is heavy, eliminates
Giving birth to test tests the result and show: The compounds of this invention has good weeding activity, and has the wider grass spectrum of killing, and the gramineous weeds and the broadleaved herb in farmland all had the good control effect.Biological activity determination:
The weeds and the crop species of the biological activity determination test usefulness of selecting are as follows:
Chinese name English name The science title Abbreviation
The barnyard grass grass barnyardgrass Echinochloa crusgalli ECHCG
Lady's-grass Crabgrass Digitaria sanguinalis DIGSA
Herba Eleusines Indicae Bullgrass Eleusine indica ELEIN
Herba Setariae Viridis Giant foxtail Setaria faberii SETEFA
Leaf mustard Leaf mustard Brassica juncea BRAJU
Amaranthus retroflexus Amaranth pigweed Amaranthus retroflexus AMARE
Purslane Common purslane Portulaca oleracea POROL
Little lamb's-quarters Lambsquarters Chenopodium album CHEAL
Corn Corn Zea mays ZEAMX
Soybean Soybean Glycine max GLXMA
Cotton Cotton Gossypium hispitum GOSHI
Wheat Wheat Triticum aestivum TRZAW
Paddy rice Rice Oryza sativa ORYSD
Rape Rape Brassica napus BRSNW
The indoor evaluated biological activity of compound
Figure C20061011682100291
Figure C20061011682100301
Figure C20061011682100312
Figure C20061011682100321
Figure C20061011682100331
Wherein, gai/ha represents: effective dose gram/hectare.

Claims (7)

1. alcohol amide condensed ester compound, under its structural formula:
Figure C2006101168210002C1
Wherein: R 1, R 4=hydrogen, hydroxyl, sulfydryl, nitro, halogen, C 1-C 8Alkyl, C 1-C 8Alkoxyl group, phenoxy group, benzene sulfydryl, heterocyclic radical, substituted heterocyclyloxy or substituted heterocycle sulfydryl; R 2=C 1-C 8Alkyl, phenyl or substituted-phenyl; R 3=hydrogen, C 1-C 8Alkyl, C 1-C 8Alkoxyl group, C 1-C 8Alkylamino, phenyl or substituted-phenyl; Wherein above-mentioned substituting group is halogen, C 1-C 8Alkyl or C 1-C 8Alkoxyl group.
2. a kind of alcohol amide condensed ester compound as claimed in claim 1 is characterized in that described heterocyclic radical is pyridyl, thienyl, thiazolyl or pyrimidyl.
3. the preparation method of an alcohol amide condensed ester compound as claimed in claim 1, its feature is by following (1) and (2), and perhaps (1) and (3) two kinds of methods make:
(1), at water or organic solvent, or in the mixed solvent of water and organic solvent composition, and under room temperature～reflux temperature, molecular formula is
Figure C2006101168210002C2
R 3Substituted formyl chlorine and molecular formula are
Figure C2006101168210002C3
R 2Replace oxyammonia and under alkaline condition, react acquisition in 0.5～72 hour R 3Substituted formyl chlorine, R 2The mol ratio that replaces oxyammonia and alkali is 1: 1-10: 1-10;
(2), at water or organic solvent, or in the mixed solvent of water and organic solvent composition, and under room temperature～reflux temperature, molecular formula is
Figure C2006101168210002C5
R 1, R 4Substituted benzoyl chloride and molecular formula are
Figure C2006101168210002C6
Intermediate (II) in the presence of alkali, react and obtained molecular formula in 0.5～72 hour and be
Figure C2006101168210002C7
Product, R 1, R 4The mol ratio of substituted benzoyl chloride, intermediate (II) and alkali is 1: 0.1-10: 1-10;
(3), at water or organic solvent, or in the mixed solvent of water and organic solvent composition, and under room temperature～reflux temperature, molecular formula is
Figure C2006101168210003C1
R 1, R 4Substituted benzoic acid and aforesaid intermediate (II) react acquisition in 0.5～72 hour in the presence of condensing agent and alkali R 1, R 4The mol ratio of substituted benzoic acid, intermediate (II), condensing agent and alkali is 1: 0.1-10: 0.1-10: 0.1-10; Described condensing agent is N, N '-dicyclohexylcarbodiimide, N, N '-DIC, N, N '-carbonyl dimidazoles, benzotriazole-1-base-oxygen base tripyrrole alkyl phosphorus phosphorus hexafluoride salt, O-(7-azepine benzo triazol-1-yl) oxygen base-N, N, N ', N '-tetramethyl-urea phosphorus hexafluoride salt, O-benzotriazole-N, N, N ', N '-tetramethyl-urea tetrafluoride boron salt or benzotriazole-1-base-oxygen base-three (dimethylamino) phosphorus phosphorus hexafluoride salt;
Wherein, described alkali is hydride, alcoxyl metallic compound or its carbonate of the organic amine compound, monovalence or the divalent metal that contain lone-pair electron; R 1, R 2, R 3And R 4According to claim 1.
4. the preparation method of a kind of alcohol amide condensed ester compound as claimed in claim 3 is characterized in that the described organic amine compound that contains lone-pair electron is triethylamine, pyridine, N, N-dimethyl aminopyridine or diisopropyl ethyl amine.
5. the preparation method of a kind of alcohol amide condensed ester compound as claimed in claim 3 is characterized in that hydride, alcoxyl metallic compound or its carbonate of described monovalence or divalent metal is sodium hydride, potassium hydride KH, hydrolith, sodium methylate, sodium ethylate, potassium methylate, potassium ethylate, yellow soda ash, salt of wormwood or lime carbonate.
6. the preparation method of a kind of alcohol amide condensed ester compound as claimed in claim 3, mixed solvent is water and ether solvent mixture in its feature described (1) and (2) step; Organic solvent is a methylene dichloride in described (3) step.
7. the purposes of an alcohol amide condensed ester compound as claimed in claim 1 is characterized in that being used to prepare agricultural herbicide.
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Regio-Selective Formation of O-Acyl/O-BenzoylHydroxamates by Using a Polymer Supported ReagentStrategy. A.S.Burungule, et al.Synthetic Communications,Vol.33 No.11. 2003 *

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