CN102757361A - 2-acetoxy-N-(3-chlor phenyl) benzamide and synthetic method and bacteriostatic action thereof - Google Patents
2-acetoxy-N-(3-chlor phenyl) benzamide and synthetic method and bacteriostatic action thereof Download PDFInfo
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Abstract
The invention is belong to the technical field of pesticide, specifically relates to 2-acetoxy-N-(3-chlor phenyl) benzamide and a synthetic method and a bacteriostatic action thereof, and aims at providing a novel compound, 2-acetoxy-N-(3-chlor phenyl) benzamide, which is prepared from the raw materials of o-ethoxybenzoyl chloride and 3-fluoroaniline by an aminolysis method of acyl halide. 2-acetoxy-N-(3-chlor phenyl) benzamide has inhibitory action to five kinds of plant pathogenic bacteria of Thanatephorus cucumeris, Sclerotinia sclerotiorum, Botrytis cinerea, FusaHum graminearum and Helminthosporium maydis, thus 2-acetoxy-N-(3-chlor phenyl) benzamide can be used for preventing and controlling sheath and culm blight of rice, sclerotinia rot of rape, gray mold of tomato, wheat scab and leaf spot of corn; and especially, 2-acetoxy-N-(3-chlor phenyl) benzamide has an obvious inhibitory action to the leaf spot of corn germ, and has a definite prevention and control effect to the leaf spot of corn. The structural formula of the compound provided by the invention is shown in the specification.
Description
Technical field
The invention belongs to pesticide field, be specifically related to 2-acetoxyl group-N-(3-chloro phenyl) BM and compound method and bacteriostatic action.
Background technology
Agricultural chemicals is meant in agriculture prodn, for ensureing, promote the growth of plant and farm crop, the desinsection of being used, sterilization, the vegeto-animal one type of medicine general designation of kill harmful.Refer in particular to and on agricultural, be used for medicaments such as insect pests and coordinate plant growth, weeding.Agricultural chemicals and agricultural, livestock industry close relation, closely bound up with life.Therefore people early know and utilize agricultural chemicals that the disease and pest of farm crop is prevented and treated.B.C. more than 1000 years, in ancient Greek, existing record with sulfur fumigation insect and diseases prevention; China is also in B.C. 5-7 century, brings into use thick grass, clam charcoal ash, male bring up etc. to kill insect.The agricultural chemicals that initial people use is mainly derived from natural plant; Utilize some position of plant or extract its effective constituent and process agricultural chemicals or utilize mineral to be raw material, the mineral compound agricultural chemicals that comes out through simple processing and manufacturing with desinsection or germicidal action.This type agricultural chemicals source is natural; Therefore have nuisanceless, can with characteristics such as environmentally compatible, mechanism of action uniqueness and development cost are cheap; Yet abstraction process is loaded down with trivial details from plant, and the material composition that extracts is complicated, and it is low therefore to have a functioning efficiency; Shortcomings such as usage quantity is big, and the effective object of desinsection, diseases prevention or weeding is single.Since the forties in 20th century, along with the continuous development of chemistry subject, the organic chemistry synthetic pesticide by feat of wide in variety, drug effect is high, effective object is diversified, advantage such as easy to use has substituted initial agricultural chemical of natural plant and inorganic pesticide.Yet a large amount of uses along with chemical pesticide; Produced a series of serious problems, like pesticide residue, harmful organism develops immunity to drugs, environmental pollution; Destroy ecotope etc., the novel agrochemical of therefore seeking efficient, low toxicity, low residue has become current sixty-four dollar question.
In agricultural, corps diseases is the significant problem in the agriculture prodn, also is the major reason that causes financial loss; The crop production reduction that annual due to illness evil causes reaches more than 10%, and in Plant diseases, fungal disease accounts for 80%; And the most of sterilant that now use all are the chemical sterilant; Cause environmental pollution easily, biology develops immunity to drugs, shortcomings such as pesticide residue.Therefore the natural compounds with biologically active in the plant-sourced is a model, carries out deriving and optimizing of its compound structure, and preparation is efficient, and the new type bactericide of safety such as low toxicity and environmentally compatible is the focus that current sterilant is studied.
Whitfield's ointment is the crude substance that a kind of vegitabilia extensively exists; It not only has important pharmacological effect; And plant growth and development process and disease resistance of plant aspect there is regulating and controlling effect widely; The contriver is that the guide derives and optimizes the structure that obtains adjacent acetoxyl group Benzoyl chloride 99min. with this structure; Further obtain 2-acetoxyl group-N-(3-chloro phenyl) BM material thus, and the bacteriostatic action of probation plant pathogenic fungi, the new type bactericide of a kind of new efficient, low toxicity, safety is provided.
Summary of the invention
The technical problem that the present invention solved provides a kind of new compound, and 2-acetoxyl group-N-(3-chloro phenyl) BM, its structural formula are suc as formula I:
The formula I.
The compounds of this invention is to be raw material with adjacent acetoxyl group Benzoyl chloride 99min. and 3-fluoroaniline, adopts amine-decomposing method Synthetic 2-acetoxyl group-N-(3-chloro phenyl) BM of carboxylic acid halides.
The compounds of this invention adopts dull and stereotyped growth rate method to measure; Inhibited to Rhizoctonia solani Kuhn, Sclerotinia sclerotiorum, botrytis cinerea, fusarium graminearum or southern corn leaf blight five kind of plant pathogenic bacterias, can be used for preventing and treating rice sheath blight disease, sclerotinia rot of colza, graw mold of tomato, wheat scab, corn southern leaf blight; Especially obvious to Sclerotinia sclerotiorum and southern corn leaf blight bacteriostatic action, have the clear and definite control sclerotinia rot of colza and the effect of corn southern leaf blight.
Further, can also The compounds of this invention be activeconstituents, acceptable auxiliary is prepared from agricultural chemicals on the adding agricultural chemicals.The concentration of activeconstituents 2-acetoxyl group-N-in the agricultural chemicals (3-chloro phenyl) BM can be brought into play effect antibacterial, that prevent and treat disease more than or equal to 6.25mg/L.
Concrete, the compound method of The compounds of this invention comprises the steps:
A, get the adjacent acetoxyl group Benzoyl chloride 99min. of raw material, 3-chloroaniline, be dissolved in organic solvent respectively and get adjacent acetoxyl group Benzoyl chloride 99min.-organic solvent solution and 3-chloroaniline-organic solvent solution, subsequent use;
Organic solvent described in the steps A is at least a in ethanol, methylene dichloride, trichloromethane, ETHYLE ACETATE, the acetone.
Add catalyzer in B, the 3-chloroaniline-organic solvent solution, drip adjacent acetoxyl group Benzoyl chloride 99min.-organic solvent solution, stirring reaction, reaction conditions is: temperature 20-40 ℃, reaction times 2-6 hour; Preferred reaction conditions is: 30 ℃ of temperature, reaction times 3-4 hour;
Catalyzer described in the step B is the weakly alkaline catalyzer; The preferred pyridine of weakly alkaline catalyzer, sodium hydroxide-ethanol solution (sodium hydroxide is 50-150g/L in this solution, preferred 100g/L), saturated solution of sodium bicarbonate.
C, step B gained reaction soln extract with the hydrochloric acid soln of 5-20% (v/v), and extraction conditions is: hydrochloric acid soln is that the 1-3 of reaction soln doubly measures volume, extracts 2-3 time;
Preferred 10% (v/v) of concentration of hydrochloric acid solution described in the step C, preferably salt acid solution are 2 times of amount volumes of reaction soln.
D, take off a layer extraction liquid, in 2-6 ℃, be placed to solid and separated out, filter, use water washing, the solid after the washing is used the absolute ethyl alcohol recrystallization, till obtaining pure substance.
Wherein, adjacent acetoxyl group Benzoyl chloride 99min. of raw material and 3-chloroaniline are reaction with same mole.
The mol ratio of catalyzer, adjacent acetoxyl group Benzoyl chloride 99min., 3-chloroaniline is: 1:1 ~ 3:1 ~ 3, preferred molar ratio are 1:1:1.Above-mentioned reaction gained compound is through IR,
1H NMR carries out structural confirmation, and its structural formula is following:
Embodiment
Below through to the description of specific embodiment of the invention explanation but do not limit the present invention.
The compounds of this invention is to be raw material with adjacent acetoxyl group Benzoyl chloride 99min. and 3-chloroaniline, adopts amine-decomposing method Synthetic 2-acetoxyl group-N-(3-chloro phenyl) BM of carboxylic acid halides.
Below, foregoing of the present invention is remake further detailed description through the embodiment of embodiment form.
Concrete compound method is:
With 3-chloroaniline material (30mmol), adjacent acetoxyl group Benzoyl chloride 99min. (30mmol) all is dissolved in respectively in the methylene dichloride of 10mL, and the 3-chlorobenzene amine substance that dissolving is good is put in the there-necked flask; Add pyridine (30mmol) again, put into 30 ℃ of thermostat water baths, will dissolve good adjacent acetoxyl group Benzoyl chloride 99min. splashing in the there-necked flask slowly again; Adopt magnetic stirring apparatus constantly to stir 3-4 hour, take out with 2 times to 10% hcl as extraction agent of reaction solution volume 2-3 time, take off a layer extraction liquid; In 2-6 ℃ of refrigerator, place, up to there being solid to separate out, filter, the water wash solids; With absolute ethyl alcohol solid is carried out recrystallization, till obtaining pure substance.
Wherein, methylene dichloride can be used ethanol, trichloromethane, ETHYLE ACETATE, acetone replacement; Weakly alkaline catalyzer replacements such as pyridine available hydrogen sodium oxide-ethanol solution (sodium hydroxide is 50-150g/L in this solution, preferred 100g/L), saturated solution of sodium bicarbonate.
Through IR,
1H NMR carries out structural confirmation, and the result of analysis is following:
2-acetoxyl group-N-(3-chloro phenyl) BM: white crystal, productive rate: 27%, m.p.126-127 ℃; IR (KBr) ν max (cm-1): 3296,3261,3187,3115,3077,1770,1743,1676,1666,1593,1537,1484,1450,1368,1316,1203,1162,1135,785,775,751,696,583; 1H NMR (400MHz, CDCl3) δ (ppm): 2.31 (s, 3H), 7.12 (t, J=8.0Hz, 2H), 7.23-7.27 (m, 1H); 7.31 (t, J=8.0Hz, 1H), 7.39 (d, J=8.0Hz, 1H), 7.49 (t; J=8.0Hz, 2H), 7.76 (t, J=8.0Hz, 1H), 8.18 (s, 1H).
3296,3187,3115cm in the ir spectra:
-1Absorption peak occurs and show have secondary amine to have 3077cm
-1With 1593,1537cm
-1With 1484,1450cm
-1Absorption peak occurs and represent to have phenyl ring to exist, 1770,1743cm
-1Absorption peak occurs and represent to have that two keys exist in the ethanoyl, 1676,1666cm
-1Absorption peak occurs and represent to have carboxamido-group to exist, 1368,1316cm
-1Absorption peak occurs and represent to have methyl to exist, 1203,1162,1135cm
-1Absorption peak occurring representes to have acetoxyl group to exist.784,696cm
-1Absorption peak occurs and represent to have 1,3-disubstituted benzenes ring, 775,751cm
-1Absorption peak occurs and represent to have 1,2-disubstituted benzenes ring, 696,583cm
-1Absorption peak occurring representes to have the two keys of carbon oxygen in the carboxamido-group to exist.
1In the HNMR spectrum, δ 2.31 is three H on the acetoxyl group on 13.δ 7.12 is the H on 9, and the H on it and 7,8 intercouples to split and is divided into triplet, and coupling constant is 8.0Hz.δ 7.23-7.27 is the H on 8, and the H on it and 7,9 intercouples and is multiplet, and δ 7.31 is the H on 8, and the H on it and 7,9 intercouples to split and is divided into triplet, and coupling constant is 8.0Hz.δ 7.33 is the H on 5, and the H on it and 4,6 intercouples and is that triplet, coupling constant are 8.0Hz.δ 7.39 is the H on 7, and the H on it and 8,9 intercouples and is split into triplet, and coupling constant is 8.0Hz.δ 7.76 is 4 and goes up H, and the H on it and 3,5 intercouples and is that triplet, coupling constant are 8.0Hz.δ 8.14 is the H on the secondary amine.
Comprehensive infrared and MASS SPECTRAL DATA ANALYSIS has identified that the structural formula of the compound that tries is as follows, has confirmed that the synthetic material is 2-acetoxyl group-N-(3-chloro phenyl) BM.
Below, foregoing of the present invention is remake further detailed description through the embodiment of embodiment form.
The research of embodiment 1 2-acetoxyl group-N-(3-chloro phenyl) BM bacteriostatic activity
Method: test compound and derosal are dissolved in respectively in the methyl-sulphoxide (DMSO); Add 0.1% tween tap water again; Adopt doubling dilution; Process a series of 2-acetoxyl group-N-(3-chloro phenyl) BM and each 1.0mL of carbendazim solution, and add Streptomycin sulphate 1.0mg (making Streptomycin sulphate is 50mg/L in the ultimate density of substratum) respectively.Corresponding solution not contain compound is made blank, is mixed with the uniform pastille flat board of thickness subsequent use (substratum sterilize earlier adding medicine again), every processing triplicate.Use the punch tool of sterilizing to beat to get and choose Ф 5mm well-grown; Pollution-free; The bacterium cake of the uniform rhizoctonia bacterium colony of growing way; Under aseptic condition, insert pastille substratum center (bacterium cake of each plating), measure colony diameter (time is that colony diameter is the incubation time about 50mm) behind the constant temperature culture 1-3d respectively at 28 ℃.By the Abbott formula bacteriostasis rate is proofreaied and correct,, adopted SPSS computed in software EC again according to probability value analytical method
50Value and fiducial interval thereof are also obtained relation conefficient and regression equation.The bacteriostasis rate formula is following relatively:
The result:
3.82% ,-1.94%, 11.15%, 9.67% ,-0.34% detect through aforesaid method: the antibacterial result of Whitfield's ointment (concentration is 100mg/L) is following: the inhibiting rate to Rhizoctonia solani Kuhn, Sclerotinia sclerotiorum, botrytis cinerea, fusarium graminearum and southern corn leaf blight is respectively:.
Through first screening; Drawing 2-acetoxyl group-N-(3-chloro phenyl) BM is respectively the inhibiting rate of Rhizoctonia solani Kuhn, Sclerotinia sclerotiorum, botrytis cinerea, fusarium graminearum and southern corn leaf blight when concentration is 100mg/L: 42.91%, 92.78%, 66.36%, 27.83%, 90.14%, and wherein the inhibition best results for rape sclerotium and southern corn leaf blight reaches more than 90%.
On the primary dcreening operation basis, measured the bacteriostatic activity of 2-acetoxyl group-N-(3-chloro phenyl) BM to Sclerotinia sclerotiorum and southern corn leaf blight, the result sees table 1,2.The result shows: 2-acetoxyl group-N-(3-chloro phenyl) BM is active to the inhibition of Sclerotinia sclerotiorum, its EC
50Value 2.01mg/L exists significant correlationship between concentration and drug effect, its equation of linear regression is 0.9841 for the Y=1.5483X+4.5314 relation conefficient.Through card side (χ
2=3.945, df=3, P>0.05) check consequently reliable.2-acetoxyl group-N-(3-chloro phenyl) BM is active to the inhibition of southern corn leaf blight, its EC
50Value 3.79mg/L exists significant correlationship between concentration and drug effect, its equation of linear regression is 0.9631 for the Y=0.8479X+4.5088 relation conefficient, through card side (χ
2=0.580, df=3, P>0.05) check consequently reliable.
Table 1 The compounds of this invention 2-acetoxyl group-N-(3-chloro phenyl) BM is active to the inhibition of Sclerotinia sclerotiorum
Table 2 The compounds of this invention 2-acetoxyl group-N-(3-chloro phenyl) BM is active to the inhibition of southern corn leaf blight
To sum up; The compounds of this invention 2-acetoxyl group-N-(3-chloro phenyl) BM is inhibited to Rhizoctonia solani Kuhn, Sclerotinia sclerotiorum, botrytis cinerea, fusarium graminearum, southern corn leaf blight five kind of plant pathogenic bacterias, can be used for preventing and treating rice sheath blight disease, sclerotinia rot of colza, graw mold of tomato, wheat scab, corn southern leaf blight; Especially obvious to Sclerotinia sclerotiorum and southern corn leaf blight bacteriostatic action, have the clear and definite control sclerotinia rot of colza and the effect of corn southern leaf blight.
Claims (10)
1. structure is suc as formula the compound shown in the I:
The formula I.
2. the compound method of compound shown in the formula I, it is characterized in that: with adjacent acetoxyl group Benzoyl chloride 99min. and 3-chloroaniline is raw material, adopts amine-decomposing method Synthetic 2-acetoxyl group-N-(3-chloro phenyl) BM of carboxylic acid halides.
3. the compound method of compound shown in the formula I according to claim 2 is characterized in that:
A, get adjacent acetoxyl group Benzoyl chloride 99min. of raw material and 3-chloroaniline, be dissolved in organic solvent respectively, adjacent acetoxyl group Benzoyl chloride 99min.-organic solvent solution and 3-chloroaniline-organic solvent solution, subsequent use;
Organic solvent described in the steps A is at least a in ethanol, methylene dichloride, trichloromethane, ETHYLE ACETATE, the acetone;
Add catalyzer in B, the 3-chloroaniline-organic solvent solution, drip adjacent acetoxyl group Benzoyl chloride 99min.-organic solvent solution, stirring reaction, reaction conditions is: temperature 20-40 ℃, reaction times 2-6 hour;
Catalyzer described in the step B is the weakly alkaline catalyzer;
Further preferred, the said reaction conditions of step B is: 30 ℃ of temperature, reaction times 3-4 hour;
C, step B gained reaction soln extract with the hydrochloric acid soln of 5-20%v/v, and extraction conditions is: hydrochloric acid soln is that the 1-3 of reaction soln doubly measures volume, extracts 2-3 time;
Further preferred, the said concentration of hydrochloric acid solution of step C is 10%v/v; Extraction conditions is: hydrochloric acid soln is 2 times of amount volumes of reaction soln, extracts 2-3 time;
D, take off a layer extraction liquid, in 2-6 ℃, be placed to solid and separated out, filter, the water washing solid, with absolute ethyl alcohol solid is carried out recrystallization, till obtaining pure substance.
4. according to the compound method of compound shown in claim 2 or the 3 described formula I, it is characterized in that: adjacent acetoxyl group Benzoyl chloride 99min. of raw material and 3-chloroaniline are reaction with same mole.
5. the compound method of compound shown in the formula I according to claim 3 is characterized in that: the mol ratio of catalyzer, adjacent acetoxyl group Benzoyl chloride 99min., 3-chloroaniline is: 1:1 ~ 3:1 ~ 3, preferred molar ratio are 1:1:1.
6. the compound method of compound shown in the formula I according to claim 3 is characterized in that: the said weakly alkaline catalyzer of step B is pyridine, sodium hydroxide-ethanol solution, saturated solution of sodium bicarbonate;
Wherein, sodium hydroxide is 50-150g/L in sodium hydroxide-ethanol solution, preferred 100g/L.
7. compound shown in the formula I is used to suppress the application of plant pathogenic fungi, it is characterized in that: described plant pathogenic fungi is Rhizoctonia solani Kuhn, Sclerotinia sclerotiorum, botrytis cinerea, fusarium graminearum or southern corn leaf blight; Preferred Sclerotinia sclerotiorum or the southern corn leaf blight of suppressing.
8. compound is used to prevent and treat rice sheath blight disease, sclerotinia rot of colza, graw mold of tomato, wheat scab or corn southern leaf blight shown in the formula I; Preferred control sclerotinia rot of colza or corn southern leaf blight.
9. agricultural chemicals is characterized in that, is activeconstituents with compound shown in the formula I, and acceptable auxiliary is prepared from the adding agricultural chemicals.
10. agricultural chemicals according to claim 9 is characterized in that: compound concentrations shown in the activeconstituents formula I is more than or equal to 6.25mg/L in the agricultural chemicals.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1440962A (en) * | 1997-03-14 | 2003-09-10 | 拜尔公司 | Substituted amino amide salicylate with Fungal killing function and tis prepared intermediate thereof |
| WO2012058378A1 (en) * | 2010-10-29 | 2012-05-03 | Romark Laboratories L.C. | Pharmaceutical compositions and methods of use of salicylanilides for treatment of hepatitis viruses |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1440962A (en) * | 1997-03-14 | 2003-09-10 | 拜尔公司 | Substituted amino amide salicylate with Fungal killing function and tis prepared intermediate thereof |
| WO2012058378A1 (en) * | 2010-10-29 | 2012-05-03 | Romark Laboratories L.C. | Pharmaceutical compositions and methods of use of salicylanilides for treatment of hepatitis viruses |
Non-Patent Citations (3)
| Title |
|---|
| REGITRY,STN: "CAS：405146-65-8", 《ACS》 * |
| 孙昌俊等: "《有机化合物合成手册》", 30 November 2011 * |
| 齐兵等: "水杨酸衍生物的合成及生物活性测定", 《武汉工程大学学报》 * |
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Application publication date: 20121031 |