CN105541743A - Bisfamoxadone-like compounds and synthetic method thereof - Google Patents

Bisfamoxadone-like compounds and synthetic method thereof Download PDF

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Publication number
CN105541743A
CN105541743A CN201510917602.8A CN201510917602A CN105541743A CN 105541743 A CN105541743 A CN 105541743A CN 201510917602 A CN201510917602 A CN 201510917602A CN 105541743 A CN105541743 A CN 105541743A
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Prior art keywords
famoxadone
compound
drip
duplex
reaction
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Inventor
韩海平
叶振君
张芝平
董建生
方燕
王曼
徐海燕
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Shengnong Biological-Chemical Products Co Ltd Shanghai
Shanghai Shengnong Pesticide Co Ltd
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Shengnong Biological-Chemical Products Co Ltd Shanghai
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Publication of CN105541743A publication Critical patent/CN105541743A/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D263/44—Two oxygen atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention provides bisfamoxadone-like compounds and pharmaceutically acceptable salts, monocrystals or polymorphic substances thereof. The bisfamoxadone-like compounds have structures as shown in a general formula (I) which is described in the specification. The invention also provides a synthetic method for the compounds and compositions containing the compounds. Preparations like pesticides containing the compounds have good prevention effect on powdery mildew, rust disease, glume blight, net blotch, downy mildew, late blight and the like of crops.

Description

A kind of duplex Lei famoxadone compound and synthetic method thereof
Technical field
The invention belongs to agricultural chemical compound field, particularly relate to a kind of duplex Lei famoxadone compound, and the synthetic method of described duplex Lei famoxadone compound.
Background technology
Famoxadone is novel, the efficient spectrum sterilant of the one developed by E.I.Du Pont Company, suitable for crop is wheat, barley, pea, beet, rape, grape, potato, melon, capsicum, tomato etc., be mainly used in preventing and treating important disease in Ascomycetes, Basidiomycetes, oomycetes subclass as Powdery Mildew, rust, glume blight, net blotch, oidium, late blight etc.
Chinese patent CN101755785A discloses a kind of fungicidal composition, it is a kind of Synergistic bactericidal composition of arbitrary fungicide active ingredient comprising enhancing effective amount famoxadone and be selected from tebuconazole, the spirit of triazolone, Evil frost, zinc 1,2-propylene bisdithiocarbamate, m-tetrachlorophthalodinitrile, pyraclostrobin, difenoconazole, kresoxim-methyl, tertraconazole and Carbatene, and this fungicidal composition has certain sterilization effect.
Chinese patent CN103396410A relates to a kind of synthetic method being used as disinfectant use in agriculture, and its synthetic route is:
Final obtained Bi famoxadone obvious Shu Yu famoxadone compounds, it is as the important effective constituent of disinfectant use in agriculture.Wherein, pyridine heterocycle is the common structure unit in agricultural chemical compound; But the fungicidal activity with Gai Bi famoxadone of said structure need to improve.
Given this, contriver intends relating to a kind of duplex Lei famoxadone compound comprising two heterocycle structure, to increase fungicidal activity, the application of farm crop obtains more excellent technique effect.
Summary of the invention
The present invention aims to provide a kind of duplex Lei famoxadone compound, and the high-efficiency synthesis method of described duplex Lei famoxadone compound.
Therefore, first aspect, the invention provides a kind of duplex Lei famoxadone compound or its pharmacy acceptable salt, monocrystalline or polymorphic form, and wherein, described duplex Lei famoxadone compound has the structure shown in general formula (I):
In this general formula (I):
R 1be selected from: H, C 1-4alkyl, trifluoromethyl;
R 2be selected from: H, halogen, methyl, ethyl, nitro, the tertiary butyl, methoxyl group, trifluoromethyl, carboxyl, cyano group.
Preferably, described R 1be selected from: H, trifluoromethyl, methyl.
Further preferably, described R 2be selected from: H, halogen, nitro, methyl, trifluoromethyl, carboxyl, cyano group.
Still more preferably, described duplex Lei famoxadone compound be selected from following any one:
Second aspect, the invention provides the synthetic method of above-mentioned duplex Lei famoxadone compound, the synthetic route of described synthetic method is as follows:
Comprising step (1): with 4,4'-dibromodiphenyl ether II for starting raw material, first carry out grignard reaction, then carry out Friedel-Crafts reaction generation intermediate III; Step (2): then, reacts gained intermediate III and solid phosgene and phenylhydrazine compounds IV, generates target product I.
Preferably, in above-mentioned synthetic method, described phenylhydrazine compounds IV be selected from following any one: phenylhydrazine, 4-nitrophenyl hydrazine, 2-nitrophenyl hydrazine, 2,4,6-trichlorobenzene hydrazine, 2-fluorine phenylhydrazine, 4-fluorine phenylhydrazine.
Preferably, in above-mentioned synthetic method, described step (1) is: in grignard reaction container, add magnesium rod and THF, after initiation reaction, more slowly drips the THF solution of 4,4'-dibromodiphenyl ether II, after dropwising, and obtained Grignard reagent heat preservation for standby use; In Friedel-Crafts reaction vessel, add pyruvate compounds and THF in addition, be cooled to-25 ~ 0 DEG C, slowly drip described Grignard reagent, drip and finish, holding temperature is at-25 ~ 0 DEG C and stirring reaction, until react completely, aftertreatment, obtains intermediate III.
Further preferably, in above-mentioned synthetic method, described step (1) is: in grignard reaction container, add magnesium rod and THF, after initiation reaction, more slowly drip the THF solution of 4,4'-dibromodiphenyl ether II, after dropwising, obtained Grignard reagent heat preservation for standby use; In Friedel-Crafts reaction vessel, add pyruvate compounds and THF in addition, be cooled to-10 ~-15 DEG C, slowly drip described Grignard reagent, drip and finish, holding temperature is at-10 ~-15 DEG C and stirring reaction, until react completely, aftertreatment, obtains intermediate III.
Preferably, in above-mentioned synthetic method, described step (2) is: in the reaction vessel that toluene is housed, add intermediate III, triethylamine, phenylhydrazine compounds IV, and add triazole or DCC or CDI, after being warming up to 80 DEG C, be more slowly cooled to 45 DEG C; Drip the toluene solution of solid phosgene, drip insulation reaction after finishing, until react completely, aftertreatment, obtained target product I.
The third aspect, the invention provides a kind of composition, it is characterized in that, it comprises above-mentioned duplex Lei famoxadone compound, and said composition can be used as sterilant or agricultural chemicals etc.
The described duplex Lei famoxadone compound with general formula I provided by the present invention, sterilization effect is excellent, during as sterilant or agricultural chemicals, has higher preventive effect.
Embodiment
The present inventor is through research, and found a kind of duplex Lei famoxadone compound, it has the structure shown in general formula (I):
Wherein:
R 1be selected from: H, C 1-4alkyl, trifluoromethyl;
R 2be selected from: H, halogen, methyl, ethyl, nitro, the tertiary butyl, methoxyl group, trifluoromethyl, carboxyl, cyano group.
In a preferred embodiment, described R 1be selected from: H, trifluoromethyl, methyl.
In a further preferred embodiment, described R 2be selected from: H, halogen, nitro, methyl, trifluoromethyl, carboxyl, cyano group.
In one more further preferred embodiment, described duplex Lei famoxadone compound be selected from following any one:
Second aspect, the invention provides the synthetic method of above-mentioned duplex Lei famoxadone compound, the synthetic route of described synthetic method is as follows:
Comprising step (1): with 4,4'-dibromodiphenyl ether II for starting raw material, first carry out grignard reaction, then carry out Friedel-Crafts reaction generation intermediate III; Step (2): then, reacts gained intermediate III and solid phosgene and phenylhydrazine compounds IV, generates target product I.
In a preferred embodiment, in above-mentioned synthetic method, described phenylhydrazine compounds IV be selected from following any one: phenylhydrazine, 4-nitrophenyl hydrazine, 2-nitrophenyl hydrazine, 2,4,6-trichlorobenzene hydrazine, 2-fluorine phenylhydrazine, 4-fluorine phenylhydrazine.
In a preferred embodiment, in above-mentioned synthetic method, described step (1) is: in grignard reaction container, add magnesium rod and THF, after initiation reaction, more slowly drip the THF solution of 4,4'-dibromodiphenyl ether II, after dropwising, obtained Grignard reagent heat preservation for standby use; In Friedel-Crafts reaction vessel, add pyruvate compounds and THF in addition, be cooled to-25 ~ 0 DEG C, slowly drip described Grignard reagent, drip and finish, holding temperature is at-25 ~ 0 DEG C and stirring reaction, until react completely, aftertreatment, obtains intermediate III.
In a further preferred embodiment, in above-mentioned synthetic method, described step 1 is: in grignard reaction container, add magnesium rod and THF, after initiation reaction, more slowly drip the THF solution of 4,4'-dibromodiphenyl ether II, after dropwising, obtained Grignard reagent heat preservation for standby use; In Friedel-Crafts reaction vessel, add pyruvate compounds and THF in addition, be cooled to-10 ~-15 DEG C, slowly drip described Grignard reagent, drip and finish, holding temperature is at-10 ~-15 DEG C and stirring reaction, until react completely, aftertreatment, obtains intermediate III.
In a preferred embodiment, in above-mentioned synthetic method, described step (2) is: in the reaction vessel that toluene is housed, add intermediate III, triethylamine, phenylhydrazine compounds IV, and add triazole or DCC or CDI, after being warming up to 80 DEG C, be more slowly cooled to 45 DEG C; Drip the toluene solution of solid phosgene, drip insulation reaction after finishing, until react completely, aftertreatment, obtained target product I.
The third aspect, the invention provides a kind of composition, it is characterized in that, it comprises above-mentioned duplex Lei famoxadone compound, and said composition can be used as sterilant or agricultural chemicals etc.
Embodiment provided by the invention and test used by reagent and raw material all can be buied by market, below in conjunction with embodiment, the present invention is further elaborated, but the present invention is not limited to following embodiment.
Embodiment 1
Step (1), the synthesis of compound 23:
In 100mL there-necked flask, add magnesium rod (33mmol), and inject THF5mL, make this THF solvent just cover liquid level, after to be triggered, slowly drip 4 again, the THF solution (15mmol) of 4 '-dibromodiphenyl ether II, drip off rear insulation 2h stand-by.In 250mL there-necked flask, add Pyruvic Acid Ethyl ester (30mmol), THF60mL, is cooled to-15 DEG C, slowly drip the Grignard solution prepared, after dripping off, holding temperature is at about-15 DEG C and insulated and stirred reacts 4h, has reacted rear acid adding shrend and has gone out, dry after dichloromethane extraction, concentrated, obtain light yellow liquid, be compound 23, yield 75%, purity 89%.
Step (2), the synthesis of compound 3:
Compound 23 (10mmol) is added in 100mL there-necked flask, triethylamine (40mmol), triazole (25mmol), toluene 30mL, after being warming up to 80 DEG C, be slowly cooled to 45 DEG C, drip the toluene solution of solid phosgene (8mmol), drip off rear insulation reaction 4h, react completely; Add hydrochloric acid reaction, direct filtration obtains product crude product, obtains compound 3, yield 57%, purity 97.3% after adopting DCM and normal hexane (1:10) to refine.
Embodiment 2
Step (1), the synthesis of compound 24: adopt method identical in embodiment 1, can obtain compound 24, its structural formula is as follows:
Step (2), the synthesis of compound 7:
The midbody compound 24 (10mmol) prepared is added in 100mL there-necked flask, triethylamine (40mmol), N, N'-carbonyl dimidazoles (CDI) (25mmol), toluene 30mL, after being warming up to 80 DEG C, slowly be cooled to 45 DEG C, drip the toluene solution of solid phosgene (8mmol), drip off rear insulation 4h, react completely; Add hydrochloric acid reaction, direct filtration obtains product crude product, obtains compound 7, yield 62%, purity 97.6% after adopting Virahol and normal hexane (1:5) to refine.
Embodiment 3
Step (1), the synthesis of compound 23: see embodiment 1.
Step (2), the synthesis of compound 8:
Compound 23 (10mmol) is added in 100mL there-necked flask, triethylamine (40mmol), N, N'-Dicyclohexylcarbodiimide (DCC) (25mmol), toluene 30mL, after being warming up to 80 DEG C, slowly be cooled to 45 DEG C, drip the toluene solution of solid phosgene (8mmol), drip off rear insulation 4h, add hydrochloric acid reaction, direct filtration obtains product crude product, compound 8 is obtained, yield 47%, purity 96.3% after adopting DCM and normal hexane (1:10) to refine.
Embodiment 4
Step (1), the synthesis of compound 25: adopt method identical in embodiment 1, can obtain compound 25, its structural formula is as follows:
Step (2), the synthesis of compound 10:
Compound 25 (10mmol) is added, triethylamine (40mmol), triazole (25mmol) in 100mL there-necked flask, toluene 30mL, after being warming up to 80 DEG C, be slowly cooled to 45 DEG C, drip the toluene solution of solid phosgene (8mmol), drip off rear insulation 4h, add hydrochloric acid reaction, direct filtration obtains product crude product, obtains compound 10 after adopting toluene refining, yield 59%, purity 97.9%.
Embodiment 5
Step (1), the synthesis of compound 23: see embodiment 1.
Step (2), the synthesis of compound 15:
Compound 23 (10mmol) is added, triethylamine (40mmol), DCC (25mmol) in 100mL there-necked flask, toluene 30mL, after being warming up to 80 DEG C, be slowly cooled to 45 DEG C, drip the toluene solution of solid phosgene (8mmol), drip off rear insulation 4h, add hydrochloric acid reaction, direct filtration obtains product crude product, obtains compound 15 after adopting DCM and normal hexane (1:10) to refine, yield 52%, purity 96.3%.
Embodiment 6
Step (1), the synthesis of compound 23: see embodiment 1.
Step (2), the synthesis of compound 21:
Compound 23 (10mmol) is added, triethylamine (40mmol), triazole (25mmol) in 100mL there-necked flask, toluene 30mL, after being warming up to 80 DEG C, be slowly cooled to 45 DEG C, drip the toluene solution of solid phosgene (8mmol), drip off rear insulation 4h, add hydrochloric acid reaction, direct filtration obtains product crude product, obtains compound 21 after adopting chloroform refining, yield 42%, purity 97.3%.
In addition, the present invention has also carried out field test to the agricultural chemicals containing duplex class famoxadone compound of the present invention, and it is remarkable that obtained experimental data demonstrates its preventive effect, the sequence number of the various compound of gained and each self-corresponding preventive effect thereof, shown in table specific as follows:
Table 1 compound structure (sequence number see compound) and preventive effect table look-up
Be described in detail specific embodiments of the invention above, but it is just as example, the present invention is not restricted to specific embodiment described above.To those skilled in the art, any equivalent modifications that the present invention is carried out and substituting also all among category of the present invention.Therefore, equalization conversion done without departing from the spirit and scope of the invention and amendment, all should contain within the scope of the invention.

Claims (10)

1. duplex class famoxadone compound or its pharmacy acceptable salt, monocrystalline or a polymorphic form, wherein, described duplex class famoxadone compound has the structure shown in general formula (I):
In this general formula (I):
R 1be selected from: H, C 1-4alkyl, trifluoromethyl;
R 2be selected from: H, halogen, methyl, ethyl, nitro, the tertiary butyl, methoxyl group, trifluoromethyl, carboxyl, cyano group.
2. duplex Lei famoxadone compound according to claim 1 or its pharmacy acceptable salt, monocrystalline or polymorphic form, is characterized in that, described R 1be selected from: H, trifluoromethyl, methyl.
3. duplex Lei famoxadone compound according to claim 2 or its pharmacy acceptable salt, monocrystalline or polymorphic form, is characterized in that, described R 2be selected from: H, halogen, nitro, methyl, trifluoromethyl, carboxyl, cyano group.
4. duplex Lei famoxadone compound according to claim 3 or its pharmacy acceptable salt, monocrystalline or polymorphic form, is characterized in that, described duplex Lei famoxadone compound be selected from following any one:
5. a synthetic method for the duplex class famoxadone compound according to any one of claim 1-4, it is characterized in that, the synthetic route of described synthetic method is as follows:
Comprising step (1): with 4,4'-dibromodiphenyl ether (II) for starting raw material, first carry out grignard reaction, then carry out Friedel-Crafts reaction generation intermediate (III); Step (2): then, reacts gained intermediate (III) and solid phosgene and phenylhydrazine compounds (IV), generates target product (I).
6. synthetic method according to claim 5, is characterized in that, described phenylhydrazine compounds (IV) be selected from following any one: phenylhydrazine, 4-nitrophenyl hydrazine, 2-nitrophenyl hydrazine, 2,4,6-trichlorobenzene hydrazine, 2-fluorine phenylhydrazine, 4-fluorine phenylhydrazine.
7. synthetic method according to claim 5, it is characterized in that, described step (1) is: in grignard reaction container, add magnesium rod and THF, after initiation reaction, slowly drip 4 again, the THF solution of 4'-dibromodiphenyl ether (II), after dropwising, obtained Grignard reagent heat preservation for standby use; In Friedel-Crafts reaction vessel, add pyruvate compounds and THF in addition, be cooled to-25 ~ 0 DEG C, slowly drip described Grignard reagent, drip and finish, holding temperature at-25 ~ 0 DEG C and stirring reaction, until react completely, aftertreatment, obtains intermediate (III).
8. synthetic method according to claim 7, it is characterized in that, described step (1) is: in grignard reaction container, add magnesium rod and THF, after initiation reaction, slowly drip 4 again, the THF solution of 4'-dibromodiphenyl ether (II), after dropwising, obtained Grignard reagent heat preservation for standby use; In Friedel-Crafts reaction vessel, add pyruvate compounds and THF in addition, be cooled to-10 ~-15 DEG C, slowly drip described Grignard reagent, drip and finish, holding temperature at-10 ~-15 DEG C and stirring reaction, until react completely, aftertreatment, obtains intermediate (III).
9. synthetic method according to claim 5, it is characterized in that, described step (2) is: in the reaction vessel that toluene is housed, add intermediate (III), triethylamine, phenylhydrazine compounds (IV), and add triazole or DCC or CDI, after being warming up to 80 DEG C, be more slowly cooled to 45 DEG C; Drip the toluene solution of solid phosgene, drip insulation reaction after finishing, until react completely, aftertreatment, obtained target product (I).
10. a composition, is characterized in that, it comprises the duplex class famoxadone compound according to any one of claim 1-4.
CN201510917602.8A 2015-12-10 2015-12-10 Bisfamoxadone-like compounds and synthetic method thereof Pending CN105541743A (en)

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Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1047079A (en) * 1989-04-21 1990-11-21 纳幕尔杜邦公司 Fungicidal oxazolidinones

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1047079A (en) * 1989-04-21 1990-11-21 纳幕尔杜邦公司 Fungicidal oxazolidinones

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
王振宁 等: "具有杀菌活性的噁唑类衍生物的研究进展", 《精细化工中间体》 *

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