CN102177898B - Application of 2-arylmorpholine and salt thereof serving as insecticide - Google Patents
Application of 2-arylmorpholine and salt thereof serving as insecticide Download PDFInfo
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- CN102177898B CN102177898B CN 201110060403 CN201110060403A CN102177898B CN 102177898 B CN102177898 B CN 102177898B CN 201110060403 CN201110060403 CN 201110060403 CN 201110060403 A CN201110060403 A CN 201110060403A CN 102177898 B CN102177898 B CN 102177898B
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- phenyl
- alkyl
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- insecticide
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Abstract
The invention discloses application of 2-arylmorpholine as shown in the chemical structural formula I or salt thereof serving as an insecticide. The formula I is shown in the specification, wherein, R<2> is chosen from H, OH or OR<1>, and R<1> is chosen from C1-C2 alkyl and C3-C4 linear alkyl or branched alkyl; R<3> is chosen from H, C1-C2 alkyl and C3-C4 linear alkyl or branched alkyl; R<4> is chosen from H, C1-C2 alkyl, C3-C4 linear alkyl or branched alkyl, ethoxyl and benzyl; R<5> is chosen from H, C1-C2 alkyl, C3-C4 linear alkyl or branched alkyl, phenyl or substituted phenyl; Ar is chosen from phenyl, substituted phenyl or 6-methoxy-2-naphthyl; and the salt of the 2-arylmorpholine is chosen from hydrochloride, hydrobromate, sulphate, nitrate or phosphate.
Description
Technical field
[0000] the present invention relates to a compounds as the application of preparation insecticide, specifically 2-aryl morpholine and salt thereof are as the application of preparation insecticide.
Background technology
[0000] Shao Ling etc. has described 4-aryl-5-triazolyl thiazole-2-imine compound apple wheel line bacterium has been had bactericidal activity (SCI, 2007,28,270).He Daohang etc. have described the synthetic and bactericidal activity [South China Science ﹠ Engineering University's journal natural science edition, 2008, (3): 60] of 4-aryl-2-(2-hydroxyl benzyl imino group) thiazole; Chinese patent (CN 101602761) has been described the bactericidal activity of the 4-tert-butyl group-5-(1,2,4-triazol-1-yl)-2-benzyl imino thiazole; (CN 101653127 for Chinese patent, CN 101632366) a kind of own azoles alcohol or the phonetic phenol of second and morpholine series bactericidal agent composition pesticide of comprising described, this composition pesticide has bactericidal activity at control agricultural disease, Ascomycotina, Basidiomycotina disease fungus and all kinds of fruit diseases; Korean Patent (KR 985669) has been described a kind of insecticide that contains the morpholine fatty acid salt effective component content; Dimethomorph (Dimethomorph) has the activity [J Agricultural Food Chem, 2000,48 (12): 5824～5828] of desinsection, antifungal and downy mildew resistance aspect; Mu Changwei etc. have described 4-[3-(pyridin-4-yl)-3-substituted-phenyl acryloyl] morpholine kind compound has good inhibitory action (SCI, 2007,28:1902～1906) to Rhizoctonia solani Kuhn and Jue Shi phytophthora; Ding Xingcheng etc. have described the synthetic and sterilization (Chinese science and technology review, 2008,24:194～195) of agricultural chemicals flumorph; Wen Jianrong etc. have described and have utilized human body hepatitis virus resisting spirit-morpholine biguanidine hydrochloride and viral A is composite that tomato virus disease is had control efficiency good [the Changjiang river vegetables, 2008, (22): 68～69)]; United States Patent (USP) (US 2009215797) and world patent (WO 2009025987) have been described the weed killer herbicide that a kind of morpholine class has free carboxy acid or carboxylate group; Japan Patent (JP 2000239276) has been described the excellent activity of morpholine analog derivative aspect weeding that contains pyrrole ring.2-aryl morpholine and salt thereof are not are not researched and developed report as the application of insecticide;
Summary of the invention
[0000] the object of the present invention is to provide the 2-aryl morpholine shown in the chemical structural formula I or its salt as the application of insecticide.
[0000]
[0000] wherein, R
2Be selected from: H, OH or OR
1, R wherein
1Be selected from: C
1～C
2Alkyl, C
3～C
4Straight chained alkyl or branched alkyl; R
3Be selected from: H, C
1～C
2Alkyl, C
3～C
4Straight chained alkyl or branched alkyl; R
4Be selected from: H, C
1～C
2Alkyl, C
3～C
4Straight chained alkyl or branched alkyl, ethoxy, Ar ' CH
2, wherein Ar ' is selected from: phenyl, 4-methoxyphenyl, 4-fluorophenyl, 4-chlorphenyl, 4-bromophenyl, 4-nitrobenzophenone, 4-aminophenyl, 4-acetylamino phenyl, 2-methanesulfonamido phenyl, 3-methanesulfonamido phenyl, 4-methanesulfonamido phenyl, 4-trifluoromethyl, 4-isobutyl phenenyl or 6-methoxyl group-2-naphthyl; R
5Be selected from: H, C
1～C
2Alkyl, C
3～C
4Straight chained alkyl or branched alkyl, phenyl or substituted-phenyl; Ar is selected from: phenyl, the 2-aminomethyl phenyl, the 3-aminomethyl phenyl, the 4-aminomethyl phenyl, the 2-hydroxy phenyl, the 3-hydroxy phenyl, the 4-hydroxy phenyl, the 2-methoxyphenyl, the 3-methoxyphenyl, the 4-methoxyphenyl, the 2-fluorophenyl, the 3-fluorophenyl, the 4-fluorophenyl, the 2-chlorphenyl, the 3-chlorphenyl, the 4-chlorphenyl, the 2-bromophenyl, the 3-bromophenyl, the 4-bromophenyl, the 2-nitrobenzophenone, the 3-nitrobenzophenone, the 4-nitrobenzophenone, the 2-aminophenyl, the 3-aminophenyl, the 4-aminophenyl, the 2-acetylamino phenyl, the 3-acetylamino phenyl, the 4-acetylamino phenyl, 2-methanesulfonamido phenyl, 3-methanesulfonamido phenyl, 4-methanesulfonamido phenyl, the 2-trifluoromethyl, the 3-trifluoromethyl, the 4-trifluoromethyl, 2, the 4-3,5-dimethylphenyl, 3, the 4-3,5-dimethylphenyl, 2, the 6-3,5-dimethylphenyl, 2-methyl-6-ethylphenyl, 2-chloro-4-fluorophenyl, 2-chloro-3-fluorophenyl, 3-chloro-4-fluorophenyl, 2, the 3-dichlorophenyl, 2, the 6-dichlorophenyl, 3, the 4-dichlorophenyl, 2,4-two chloro-5-fluorophenyls, 2,6-dichlor-4-trifluoromethyl phenyl, 2-acetylaminohydroxyphenylarsonic acid 5-carbethoxy phenyl, 2-acetylaminohydroxyphenylarsonic acid 5-carboxyl phenyl or 6-methoxyl group-2-naphthyl; Its salt is selected from hydrochloride, hydrobromate, sulphate, nitrate or phosphate.
[0000] the object of the invention is to also provide the 2-aryl morpholine salt shown in the chemical structural formula I is that 4-ethoxy-2-(4-ethoxyl phenenyl) morpholine hydrochloride is as the application of the insecticide that kills black bean aphid.
[0000]
[0000] the object of the invention is to also provide the 2-aryl morpholine salt shown in the chemical structural formula I is that 4-ethoxy-2-(2,4-, two chloro-5-fluorophenyls) morpholine hydrochloride is as the application of weed killer herbicide.
[0000] the object of the invention is to also provide the 2-aryl morpholine shown in the chemical structural formula I is that 3,5-dimethyl-2-(6-methoxyl group-2-naphthyl) morpholine is as the application of the insecticide that kills black bean aphid.
[0000]
[0000] the object of the invention is to also provide the 2-aryl morpholine salt shown in the chemical structural formula I is that 3,5,5-trimethyl-2-(6-methoxyl group-2-naphthyl) morpholine hydrochloride is as the application of the insecticide that kills mythimna separata.
[0000]
[0000] the object of the invention is to also provide the 2-aryl morpholine salt shown in the chemical structural formula I is that 3,4-dimethyl-2-(6-methoxyl group-2-naphthyl) morpholine hydrochloride is as the application of the insecticide that kills two-spotted spider mite.
[0000]
[0000] the present invention compared with prior art has following advantage:
[0000] finds that first 2-aryl morpholine or its salt have insecticidal activity, can be used for preparing insecticide.
Embodiment
[0000] following examples are intended to illustrate the present invention rather than limitation of the invention further.
[0000] preparation of embodiment 12-aryl morpholine and salt thereof
[0000] presses document [organic chemistry, 2004,24 (8): 902-905; Applied chemistry, 2005,22 (3): 343-345; Hunan University's journal, 2004,31 (4): 11-14; 2005,32 (4): 72-76] method prepares 2-aryl morpholine and salt (I) thereof.
[0000]
[0000] wherein, R
2Be selected from: H, OH or OR
1, R wherein
1Be selected from: C
1～C
2Alkyl, C
3～C
4Straight chained alkyl or branched alkyl; R
3Be selected from: H, C
1～C
2Alkyl, C
3～C
4Straight chained alkyl or branched alkyl; R
4Be selected from: H, C
1～C
2Alkyl, C
3～C
4Straight chained alkyl or branched alkyl, ethoxy, Ar ' CH
2, wherein Ar ' is selected from: phenyl, 4-methoxyphenyl, 4-fluorophenyl, 4-chlorphenyl, 4-bromophenyl, 4-nitrobenzophenone, 4-aminophenyl, 4-acetylamino phenyl, 2-methanesulfonamido phenyl, 3-methanesulfonamido phenyl, 4-methanesulfonamido phenyl, 4-trifluoromethyl, 4-isobutyl phenenyl or 6-methoxyl group-2-naphthyl; R
5Be selected from: H, C
1～C
2Alkyl, C
3～C
4Straight chained alkyl or branched alkyl, phenyl or substituted-phenyl; Ar is selected from: phenyl, the 2-aminomethyl phenyl, the 3-aminomethyl phenyl, the 4-aminomethyl phenyl, the 2-hydroxy phenyl, the 3-hydroxy phenyl, the 4-hydroxy phenyl, the 2-methoxyphenyl, the 3-methoxyphenyl, the 4-methoxyphenyl, the 2-fluorophenyl, the 3-fluorophenyl, the 4-fluorophenyl, the 2-chlorphenyl, the 3-chlorphenyl, the 4-chlorphenyl, the 2-bromophenyl, the 3-bromophenyl, the 4-bromophenyl, the 2-nitrobenzophenone, the 3-nitrobenzophenone, the 4-nitrobenzophenone, the 2-aminophenyl, the 3-aminophenyl, the 4-aminophenyl, the 2-acetylamino phenyl, the 3-acetylamino phenyl, the 4-acetylamino phenyl, 2-methanesulfonamido phenyl, 3-methanesulfonamido phenyl, 4-methanesulfonamido phenyl, the 2-trifluoromethyl, the 3-trifluoromethyl, the 4-trifluoromethyl, 2, the 4-3,5-dimethylphenyl, 3, the 4-3,5-dimethylphenyl, 2, the 6-3,5-dimethylphenyl, 2-methyl-6-ethylphenyl, 2-chloro-4-fluorophenyl, 2-chloro-3-fluorophenyl, 3-chloro-4-fluorophenyl, 2, the 3-dichlorophenyl, 2, the 6-dichlorophenyl, 3, the 4-dichlorophenyl, 2,4-two chloro-5-fluorophenyls, 2,6-dichlor-4-trifluoromethyl phenyl, 2-acetylaminohydroxyphenylarsonic acid 5-carbethoxy phenyl, 2-acetylaminohydroxyphenylarsonic acid 5-carboxyl phenyl or 6-methoxyl group-2-naphthyl; Its salt is selected from hydrochloride, hydrobromate, sulphate, nitrate or phosphate.
[0000] embodiment 22-aryl morpholine or its salt pair mythimna separata, black bean aphid and two-spotted spider mite cytotoxicity are measured
[0000] 1 for the examination target
[0000] mythimna separata (My, thimna sepatara) is with fresh corn leaf raising sensitive strain for many years; Test is 3 instar larvaes with worm; Black bean aphid (Aphis fabae) is indoor with broad bean seedling raising sensitive strain for many years, if test is 3 age in days aphids with worm; Two-spotted spider mite (Tetranychus urticae) is indoor with broad bean seedling raising sensitive strain for many years.Test is healthy one-tenth mite with worm.
[0000] 2 condition of culture
[0000] condition of culture for target after examination target and the test is 25 ± 5 ℃ of temperature, relative moisture 65 ± 5%, periodicity of illumination 12/12h (L/D).
[0000] 3 test medicine (former medicine): 2-aryl morpholine or its salt.
[0000] 4 medicament is prepared former medicine: take by weighing aequum with ten thousand/electronic balance; Solvent: DMF (DMF), 0.2%; Emulsifier: Tween 80,0.2%; Add clear water and be diluted to desired concn.
[0000] 5 test method is with reference to " pesticide bioactivity is estimated SOP ".
[0000] the general sieve of mythimna separata: adopt spray-on process.In being lined with the culture dish of filter paper (Φ 90mm), put into the basically identical maize leaves section of size, access again 10 of third-instar larvaes, be put under the Potter spray tower and spray.Spray amount 1ml/10 head, 2 repetitions.Be disposed, be put in the observation ward and cultivate.Regularly observe.Check behind the 96h and the record death condition, calculate lethality.
[0000] the general sieve of black bean aphid adopts infusion process.If will cut with the broad bean seedling of 3 age in days broad bean aphids, dipping took out in 10 seconds afterwards in the liquid for preparing, and was inserted on the sponge that suctions water, covered the lampshade that starts, and every processing repeats for 2 times.Be disposed, be put in the observation ward and cultivate, regularly observe, check behind the 72h and the record death condition, calculate lethality.
[0000] two-spotted spider mite is adopted infusion process.To cut with the broad bean seedling of two spotted spider mite, and soak taking-up in 10 seconds in the liquid for preparing, and suck unnecessary liquid around plant and the mite body with filter paper, and be inserted on the beaker that dress water sealed, every processing repeats for 2 times.Be disposed, be put in the observation ward and cultivate, regularly observe, check behind the 72h and the record death condition, calculate lethality.
[0000] 6 cytotoxicity
[0000] cytotoxicity of preferred compound: when active ingredient concentration was 1000mg/L, behind the dispenser 72h, 3,5,5-trimethyl-2-(6-methoxyl group-2-naphthyl) morpholine hydrochloride was 100% to the cytotoxicity of mythimna separata; When active ingredient concentration is 500mg/L, behind the dispenser 72h, 4-ethoxy-2-(4-ethoxyl phenenyl) morpholine hydrochloride and 3,5-dimethyl-2-(6-methoxyl group-2-naphthyl) morpholine is respectively 59.19% and 55.26% to the cytotoxicity of black bean aphid (Aphis fabae); 3,4-dimethyl-2-(6-methoxyl group-2-naphthyl) morpholine hydrochloride is 63.76% to the cytotoxicity of two spotted spider mite (Tetranychus urticae).2-aryl morpholine or its salt have good insecticidal activity, can be used as the preparation insecticide and use in agricultural.
Claims (5)
1. 2-aryl morpholine shown in the chemical structural formula I or its salt application in the preparation insecticide:
Wherein, R
2Be selected from: H; R
3Be selected from: H, C
1～C
2Alkyl, C
3～C
4Straight chained alkyl or branched alkyl; R
4Be selected from: H, C
1～C
2Alkyl, C
3～C
4Straight chained alkyl or branched alkyl, ethoxy; R
5Be selected from: H, C
1～C
2Alkyl, C
3～C
4Straight chained alkyl or branched alkyl; Ar is selected from: phenyl, the 2-aminomethyl phenyl, the 3-aminomethyl phenyl, the 4-aminomethyl phenyl, the 2-hydroxy phenyl, the 3-hydroxy phenyl, the 4-hydroxy phenyl, the 2-methoxyphenyl, the 3-methoxyphenyl, the 4-methoxyphenyl, the 2-fluorophenyl, the 3-fluorophenyl, the 4-fluorophenyl, the 2-chlorphenyl, the 3-chlorphenyl, the 4-chlorphenyl, the 2-bromophenyl, the 3-bromophenyl, the 4-bromophenyl, the 2-nitrobenzophenone, the 3-nitrobenzophenone, the 4-nitrobenzophenone, the 2-aminophenyl, the 3-aminophenyl, the 4-aminophenyl, the 2-acetylamino phenyl, the 3-acetylamino phenyl, the 4-acetylamino phenyl, 2-methanesulfonamido phenyl, 3-methanesulfonamido phenyl, 4-methanesulfonamido phenyl, the 2-trifluoromethyl, the 3-trifluoromethyl, the 4-trifluoromethyl, 2, the 4-3,5-dimethylphenyl, 3, the 4-3,5-dimethylphenyl, 2, the 6-3,5-dimethylphenyl, 2-methyl-6-ethylphenyl, 2-chloro-4-fluorophenyl, 2-chloro-3-fluorophenyl, 3-chloro-4-fluorophenyl, 2, the 3-dichlorophenyl, 2, the 6-dichlorophenyl, 3, the 4-dichlorophenyl, 2,4-two chloro-5-fluorophenyls, 2,6-dichlor-4-trifluoromethyl phenyl, 2-acetylaminohydroxyphenylarsonic acid 5-carbethoxy phenyl, 2-acetylaminohydroxyphenylarsonic acid 5-carboxyl phenyl or 6-methoxyl group-2-naphthyl; Its salt is selected from hydrochloride, hydrobromate, sulphate, nitrate or phosphate.
2. the application of the insecticide of black bean aphid is killed in the conduct of 2-aryl morpholine salt 4-ethoxy-2-claimed in claim 1 (4-ethoxyl phenenyl) morpholine hydrochloride:
3. 2-aryl morpholine 3 claimed in claim 1,5-dimethyl-2-(6-methoxyl group-2-tea base) morpholine are as the application of the insecticide that kills black bean aphid:
4. 2-aryl morpholine salt 3 claimed in claim 1,4-dimethyl-2-(6-methoxyl group-2-tea base) morpholine hydrochloride are as the application of the insecticide that kills two-spotted spider mite:
5.2-aryl morpholine salt 3,5, the application of the insecticide of mythimna separata is killed in the conduct of 5-trimethyl-2-(6-methoxyl group-2-naphthyl) morpholine hydrochloride:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201110060403 CN102177898B (en) | 2011-03-14 | 2011-03-14 | Application of 2-arylmorpholine and salt thereof serving as insecticide |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201110060403 CN102177898B (en) | 2011-03-14 | 2011-03-14 | Application of 2-arylmorpholine and salt thereof serving as insecticide |
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|---|---|
| CN102177898A CN102177898A (en) | 2011-09-14 |
| CN102177898B true CN102177898B (en) | 2013-03-20 |
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|---|---|---|---|
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3637680A (en) * | 1968-03-04 | 1972-01-25 | Europ De Rech Mauvernay Sa Cen | 2-(3-trifluoromethyl)-phenyl morpholines |
-
2011
- 2011-03-14 CN CN 201110060403 patent/CN102177898B/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3637680A (en) * | 1968-03-04 | 1972-01-25 | Europ De Rech Mauvernay Sa Cen | 2-(3-trifluoromethyl)-phenyl morpholines |
Non-Patent Citations (1)
| Title |
|---|
| 胡艾希等.盐酸2-芳基吗啉的合成与表征.《湖南大学学报（自然科学版）》.2005,第32卷(第4期),第72-76页. * |
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