CN102690246B - Oxime ether amine compound or oxime ether amine salt, composition containing oxime ether amine compound or oxime ether amine salt and application thereof - Google Patents
Oxime ether amine compound or oxime ether amine salt, composition containing oxime ether amine compound or oxime ether amine salt and application thereof Download PDFInfo
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- CN102690246B CN102690246B CN201210171890.3A CN201210171890A CN102690246B CN 102690246 B CN102690246 B CN 102690246B CN 201210171890 A CN201210171890 A CN 201210171890A CN 102690246 B CN102690246 B CN 102690246B
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- ethamine
- oxygen base
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Abstract
The invention discloses an oxime ether amine compound or oxime ether amine salt, a composition containing oxime ether amine compound or oxime ether amine salt and application thereof. The oxime ether amine compound or the oxime ether amine salt is provided with a structure general formula as a general formula (1) or a general formula (2). The invention also discloses one composition containing the oxime ether amine compound or the oxime ether amine salt or an auxin plants growth promoter. The invention further discloses the application of the oxime ether amine compound or the oxime ether amine salt or the composition containing the oxime ether amine compound or the oxime ether amine salt. Since the oxime ether amine compound or the oxime ether amine salt or the composition containing the oxime ether amine compound or the oxime ether amine salt is provided with obvious cutting root growth activity, number, average length or height of adventitious roots of cuttings are greatly promoted, and action concentration is quite wide in range.
Description
Technical field
The present invention relates to plant to have the compound of growth regulating effect, relate in particular to oxime ether aminated compounds or its salt, the composition that comprises oxime ether aminated compounds or its salt and the application as plant rooting promoter thereof.
Background technology
Garden Engineering person, through the method for conventional cuttage, comes amount reproduction trees, fruit tree and flowers.Cottage propagation can keep the good character of parent, shortens growing-seedling period.The formation of plant cuttings adventive root in cottage propagation process is the key point of cuttage success or failure, plant rooting promoter plays vital effect in the formation of adventive root, and the rooting percent of processing through root-inducing promoter, transplanting survival rate, height of seedling, leading thread have generally raising.Common root-inducing promoter is mainly auxins at present, as 3-indolyl acetic acid, and 3-indolebutyric acid, naphthylacetic acid etc.But these compounds are synthetic complicated on the one hand, and price is more expensive, and use inconvenience.As unstable in 3-indolyl acetic acid, see that light easily decomposes, in plant materials, can be decomposed and inactivation by indoleacetic acid oxidase Quick Oxidation simultaneously; Though 3-indolebutyric acid is more stable than indolylacetic acid, poorly water-soluble; Naphthylacetic acid is compared with 3-indolebutyric acid, has certain toxicity, and excessive concentration easily injures plant.And these growth hormone do not have short root growth activity to a lot of plants, therefore, seek the novel compound with the short root activity of cutting significant.
Summary of the invention
An object of the present invention is to provide a kind of oxime ether aminated compounds or its salt cutting to short root activity, to improve the effect of cuttage breeding method.
Another object of the present invention is to provide a kind of composition cutting to short root activity.
For realizing above-mentioned first object, the reaction that oxime ether aminated compounds of the present invention represents by following chemical equation is prepared under alkaline condition:
Or,
Wherein,
R
1, R
2be hydrogen, C1-C5 alkyl independently respectively, replace or unsubstituted aryl; Wherein, work as R
1or R
2for replace aryl time, it be the aryl of hydrogen, halogen, nitro or the replacement of C1-C5 alkyl, it is monosubstituted, two replacements or trisubstituted;
R
3, R
4be CH independently respectively
3, C
2h
5, C
3h
7, C
4h
9, C
5h
11, C
6h
13, phenyl, furyl;
N is the integer of 1-6, and m is 2 or 3.
Preferably, R
1and R
2for the aryl replacing.
By passing into dry HCl gas in the organic solvent system of oxime ether aminated compounds to being dissolved with, or in its organic solvent system, add acetic acid, phosphoric acid or citric acid, can prepare respectively hydrochloride, acetate, phosphoric acid salt or the Citrate trianion of oxime ether aminated compounds
For realizing above-mentioned second object, the invention provides a kind of composition, in said composition, include oxime ether aminated compounds or its salt that first object of the present invention provides, and auxins plant growth promoter.
Preferably, described auxins plant growth promoter is 3-indolebutyric acid.
The oxime ether aminated compounds that the present invention is synthetic or its salt, and the composition that comprises oxime ether aminated compounds or its salt has the short root activity of obvious cutting, the radical of the adventive root to cutting, average root are long or take root and highly have stronger promoter action, and activity scope is wider.
Embodiment
Preparation and the application of the represented oxime ether aminated compounds of general formula of the present invention are described in further detail below by specific embodiment.Only the present invention will be described for these embodiment, rather than limit the invention.
Embodiment 1:N, N-piperidyl-2-(benzaldoxime oxygen base) ethamine (compound 1c) synthetic
In dry bis-mouthfuls of flasks of 100 mL, add 6.7 g (0.05 mol) benzaldoxime, 2.4 g (0.06 mol) sodium hydroxide and 15.0 mL water.Regulate 50 ℃ of stirring and dissolving 30 min of temperature, drip the solution that 11.0 g (0.06 mol) N-(2-chloroethyl) piperidine hydrochlorate and 15.0 mL water are made into, last 30 min.Drip 100 ℃ of rear adjusting temperature and continue reaction 8 h, obviously there is layering in reaction solution now, cooling, separate organic phase, anhydrous diethyl ether for water layer (3 × 20.0 mL) extraction, merges organic phase, washing, dry, normal pressure steams and desolventizes, and obtains Vandyke brown liquid, cross silicagel column, moving phase is ethyl acetate and methyl alcohol, obtains target product, productive rate 48.2%.Target product is colourless oil liquid, IR (KBr) υ, cm
-1: IR (KBr) υ, cm
-1: 3061 (Ar-H), 1653 (C=N), 1602,1447 (phenyl ring skeletal vibrations), 1050 (C-O).
1h NMR (600MHz, CDCl
3): 1.430-1.453 (t, 6H, J=7.2 Hz), 1.601-1.627 (q, 4H, J=4.8 Hz), (2.493 s, 4H), 2.710-2.730 (t, 2H, J=6.0 Hz), 4.314-4.336 (t, 2H, J=6.0 Hz), 7.357-7.365 (d, 3H, J=4.8 Hz), 7.567-7.576 (d, 2H, J=6.0 Hz, J=4.8 Hz), (8.096 s, 1H)
Other compounds can be synthetic with reference to the method for embodiment 1, and this is understandable for having the professional of chemosynthesis knowledge background, and therefore building-up process differs and one illustrates.
Embodiment 2:N, N-dimethyl-2-(4-chlorobenzaldehyde oxime oxygen base) ethamine (compound 2a) synthetic
Colourless oil liquid, IR (KBr) υ, cm
-1: IR (KBr) υ, cm
-1: 3028 (Ar-H), 1648 (C=N), 1600,1492,1469 (phenyl ring skeletal vibrations), 1038 (C-O).
1h NMR (600MHz, CDCl
3) δ: 2.322 (s, 6H), 2.662-2.679 (t, 2H, J=6.0 Hz), 4.273-4.291 (t, 2H, J=6.0 Hz), 7.326-7.343 (dd, 2H, J=6.0 Hz, J=2.4 Hz), 7.498-7.516 (dd, 2H, J=6.0 Hz, J=2.4 Hz), 8.076-8.080 (d, 1H, J=2.4 Hz)
Embodiment 3:N, N-diethyl-2-(4-chlorobenzaldehyde oxime oxygen base) ethamine (compound 2b) synthetic
Colourless oil liquid, IR (KBr) υ, cm
-1: IR (KBr) υ, cm
-1: 3034 (Ar-H), 1651 (C=N), 1595,1465 (phenyl ring skeletal vibrations), 1043 (C-O).
1h NMR (600MHz, CDCl
3) δ: 1.049-1.069 (t, 6H, J=6.0 Hz), 2.604-2.641 (q, 4H, J=7.2 Hz), 2.789-2.817 (t, 2H, J=6.0 Hz), 4.247-4.268 (t, 2H, J=6.0 Hz), 7.328-7.342 (d, 2H, J=8.4 Hz), 7.502-7.516 (d, 2H, J=8.4 Hz), 8.053 (s, 1H)
Embodiment 4:N, N-piperidyl-2-(4-chlorobenzaldehyde oxime oxygen base) ethamine (compound 2c) synthetic
Colourless oil liquid, IR (KBr) υ, cm
-1: IR (KBr) υ, cm
-1: 3031 (Ar-H), 1648 (C=N), 1598,1492,1468 (phenyl ring skeletal vibrations), 1043 (C-O).
1h NMR (600MHz, CDCl
3) δ: 1.443 (s, 2H), 1.607-1.636 (m, 4H, J=6.0 Hz), 2.488 (s, 4H), 2.700-2.720 (t, 2H, J=6.0 Hz), 4.307-4.329 (t, 2H, J=6.0 Hz), 7.324-7.341 (t, 2H, J=7.2 Hz), 7.496-7.513 (t, 2H, J=7.2 Hz), 8.046-8.050 (d, 1H, J=2.4 Hz)
Embodiment 5:N, N-dimethyl-2-(acetophenone oxime oxygen base) ethamine (compound 3a) synthetic
Brown oily liquids, IR (KBr) υ, cm
-1: IR (KBr) υ, cm
-1: 3057 (Ar-H), 1613 (C=N), 1596,1496,1445 (phenyl ring skeletal vibrations), 1042 (C-O).
1h NMR (600MHz, CDCl
3) δ: 1.05-1.09 (t, 6 H, J=7.2 Hz), 2.23 (s, 3 H), 2.61-2.67 (q, 4 H, J=7.2 Hz), 2.85-2.87 (t, 2 H, J=6.6 Hz), 4.30-4.32 (t, 2 H, J=6.6 Hz), (7.35-7.37 q, 3 H, J=6.6 Hz), 7.63-7.64 (d, 2 H, J=6.6 Hz).
Embodiment 6:N, N-diethyl-2-(acetophenone oxime oxygen base) ethamine (compound 3b) synthetic
Brown oily liquids, IR (KBr) υ, cm
-1: IR (KBr) υ, cm
-1: 3055 (Ar-H), 1686 (C=N), 1598,1497,1447 (phenyl ring skeletal vibrations), 1044 (C-O).
1h NMR (600MHz, CDCl
3): 1.05-1.09 (t, 6 H, J=7.2 Hz), 2.23 (s, 3 H), 2.61-2.67 (q, 4 H, J=7.2 Hz), 2.85-2.87 (t, 2 H, J=6.6 Hz), 4.30-4.32 (t, 2 H, J=6.6 Hz), 7.35-7.37 (q, 3 H, J=6.6 Hz), 7.63-7.64 (d, 2 H, J=6.6 Hz). H, J=8.0Hz), 2.227 (s, 3H), 2.517 (s, 4H), 2.740-2.759 (t, 2H, J=10.0Hz), 4.348-4.368 (t, 2H, J=10.0Hz), 7.351 (s, 3H), 7.636-7.647 (d, 2H, J=9.0Hz)
Embodiment 7:N, N-piperidyl-2-(acetophenone oxime oxygen base) ethamine (compound 3c) synthetic
Brown oily liquids, IR (KBr) υ, cm-1:IR (KBr) υ, cm
-1: 3055 (Ar-H), 1612 (C=N), 1493,1442 (phenyl ring skeletal vibrations), 1044 (C-O).
1h NMR (600MHz, CDCl3) δ: 1.443 (s, 2H), 1.606-1.622 (t, 4H, J=8.0Hz), 2.227 (s, 3H), 2.517 (s, 4H), 2.740-2.759 (t, 2H, J=10.0Hz), 4.348-4.368 (t, 2H, J=10.0Hz), 7.351 (s, 3H), 7.636-7.647 (d, 2H, J=9.0Hz).
Embodiment 8:N, N-dimethyl-2-(4-fluorophenethyl ketoxime oxygen base) ethamine (compound 4a) synthetic
Yellow oily liquid, IR (KBr) υ, cm
-1iR (KBr) υ, cm
-1: 3041 (Ar-H), 1615 (C=N), 1603,1533,1462 (phenyl ring skeletal vibrations), 1031 (C-O).
1h NMR (600MHz, CDCl
3) δ: 2.221 (s, 3H), 2.344 (s, 6H), 2.699-2.728 (t, 2H, J=6.0 Hz), 4.303-4.322 (t, 2H, J=6.0 Hz), 7.029-7.058 (t, 2H, J=9.0 Hz), 7.616-7.640 (dd, 2H, J=9.0 Hz)
Embodiment 9:N, N-diethyl-2-(4-fluorophenethyl ketoxime oxygen base) ethamine (compound 4b) synthetic
Yellow oily liquid, IR (KBr) υ, cm
-1: IR (KBr) υ, cm
-1: 3051 (Ar-H), 1614 (C=N), 1602,1511,1458 (phenyl ring skeletal vibrations), 1037 (C-O).
1h NMR (600MHz, CDCl
3) δ: 1.059-1.083 (t, 6H, J=7.2 Hz), 2.204 (s, 3H), 2.622-2.657 (q, 4H, J=7.2 Hz), 2.834-2.854 (t, 2H, J=6.0 Hz), 4.283-4.303 (t, 2H, J=6.0 Hz), 7.320-7.334 (d, 2H, J=8.4 Hz), 7.579-7.593 (d, 2H, J=8.4 Hz)
Embodiment 10:N, N-piperidyl-2-(4-fluorophenethyl ketoxime oxygen base) ethamine (compound 4c) synthetic
Yellow oily liquid, IR (KBr) υ, cm
-1: IR (KBr) υ, cm
-1: 3058 (Ar-H), 1616 (C=N), 1600,1506,1439 (phenyl ring skeletal vibrations), 1043 (C-O).
1h NMR (600MHz, CDCl
3) δ: 1.443-1.451 (d, 2H, J=4.8 Hz), 1.593-1.630 (m, 4H, J=5.4 Hz), 2.207 (s, 3H), 2.509 (s, 4H), 2.726-2.746 (t, 2H, J=6.0 Hz), 4.334-4.354 (t, 2H, J=6.0 Hz), 7.027-7.056 (t, 2H, J=9.0 Hz), 7.616-7.639 (dd, J=8.4 Hz)
Embodiment 11:N, N-dimethyl-2-(4-chloro-acetophenone oxime oxygen base) ethamine (compound 5a) synthetic
Yellow oily liquid, IR (KBr) υ, cm
-1: IR (KBr) υ, cm
-1: 3031 (Ar-H), 1648 (C=N), 1603,1486,1453 (phenyl ring skeletal vibrations), 1038 (C-O).
1h NMR (600MHz, CDCl
3) δ: 2.334 (s, 6H), 2.672-2.791 (t, 2H, J=6.0 Hz), 4.283-4.303 (t, 2H, J=6.0 Hz), 7.318-7.332 (d, 2H, J=8.4 Hz), 7.574-7.588 (d, 2H, J=8.4 Hz)
Embodiment 12:N, N-diethyl-2-(4-chloro-acetophenone oxime oxygen base) ethamine (compound 5b) synthetic
Yellow oily liquid, IR (KBr) υ, cm
-1: IR (KBr) υ, cm
-1: 3052 (Ar-H), 1639 (C=N), 1605,1489 (phenyl ring skeletal vibrations), 1048 (C-O).
1h NMR (600MHz, CDCl
3) δ: 1.061-1.084 (t, 6H, J=7.2 Hz), 2.204 (s, 3H), 2.626-2.661 (q, 4H, J=7.2 Hz), 2.837-2.857 (t, 2H, J=6.0 Hz), 4.285-4.305 (t, 2H, J=6.0 Hz), 7.320-7.334 (d, J=8.4 Hz), 7.578-7.592 (d, 2H, J=8.4 Hz)
Embodiment 13:N, N-piperidyl-2-(4-chloro-acetophenone oxime oxygen base) ethamine (compound 5c) synthetic
Yellow oily liquid, IR (KBr) υ, cm
-1: IR (KBr) υ, cm
-1: 3040 (Ar-H), 1606 (C=N), 1489,1442 (phenyl ring skeletal vibrations), 1040 (C-O).
1h NMR (600MHz, CDCl
3) δ: 1.443-1.450 (d, 2H, J=6.0 Hz), 1.593-1.630 (m, 4H, J=6.0 Hz), 2.199 (s, 3H), 2.590 (s, 4H), 2.727-2.747 (t, 2H, J=6.0 Hz), 4.338-4.358 (t, 2H, J=6.0 Hz), 7.316-7.331 (d, 2H, J=9.0 Hz), 7.576-7.591 (t, 2H, J=9.0 Hz)
Embodiment 14:N, N-dimethyl-2-(4-bromoacetophenone oxime oxygen base) ethamine (compound 6a) synthetic
Brown oily liquids, IR (KBr) υ, cm
-1: IR (KBr) υ, cm
-1: 3052 (Ar-H), 1609 (C=N), 1582,1486,1453 (phenyl ring skeletal vibrations), 1032 (C-O).
1h NMR (600MHz, CDCl
3) δ: 2.209 (s, 3H), 2.330 (s, 6H), 2.683-2.702 (t, 2H, J=6.0 Hz), 4.299-4.319 (t, 2H, J=6.0 Hz), 7.473-7.487 (d, 2H, J=8.4 Hz), 7.512-7.526 (d, 2H, J=8.4 Hz)
Embodiment 15:N, N-diethyl-2-(4-bromoacetophenone oxime oxygen base) ethamine (compound 6b) synthetic
Brown oily liquids, IR (KBr) υ, cm
-1: IR (KBr) υ, cm
-1: 3031 (Ar-H), 1605 (C=N), 1580,1486,1442 (phenyl ring skeletal vibrations), 1037 (C-O).
1h NMR (600MHz, CDCl
3) δ: 1.054-1.078 (t, 6H, J=7.2 Hz), 2.199 (s, 3H), 2.615-2.650 (q, 4H, J=6.6 Hz), 2.826-2.847 (t, 2H, J=6.0 Hz), 4.279-4.299 (t, 2H, J=6.0 Hz), 7.472-7.487 (d, 2H, J=9.0 Hz), 7.513-7.527 (d, 2H, J=9.0 Hz)
Embodiment 16:N, N-piperidyl-2-(4-bromoacetophenone oxime oxygen base) ethamine (compound 6c) synthetic
Brown oily liquids, IR (KBr) υ, cm
-1iR (KBr) υ, cm
-1: 3056 (Ar-H), 1609 (C=N), 1586,1483,1450 (phenyl ring skeletal vibrations), 1047 (C-O).
1h NMR (600MHz, CDCl
3) δ: 1.424-1.463 (m, 2H, J=6.0 Hz), 1.595-1.633 (m, 4H, J=6.0 Hz), 2.195 (s, 3H), 2,511 (s, 4H), 2.728-2.748 (t, 2H, J=6.0 Hz), 4.340-4.360 (t, 2H, J=6.0 Hz), 7.472-7.486 (d, 2H, J=8.4 Hz), 7.512-7.526 (d, 2H, J=8.4 Hz)
Embodiment 17:N, N-dimethyl-2-(2,5-dichloroacetophenone oxime oxygen base) ethamine (compound 7a) synthetic
Brown oily liquids, IR (KBr) υ, cm
-1: IR (KBr) υ, cm
-1: 3063 (Ar-H), 1648 (C=N), 1556,1459, (phenyl ring skeletal vibration), 1038 (C-O).
1h NMR (600MHz, CDCl
3) δ: 2.214 (s, 3H), 2.347 (s, 6H), 2.692-2.711 (t, 2H, J=6.0 Hz), 4.302-4.321 (t, 2H, J=6.0 Hz), 7.257-7.275 (m, 1H, J=4.2 Hz, J=2.4 Hz), 7.310-7.325 (q, 2H, J=4.2 Hz, J=2.4 Hz)
Embodiment 18:N, N-diethyl-2-(2,5-dichloroacetophenone oxime oxygen base) ethamine (compound 7b) synthetic
Brown oily liquids, IR (KBr) υ, cm
-1: IR (KBr) υ, cm
-1: 3063 (Ar-H), 1648 (C=N), 1553,1459 (phenyl ring skeletal vibrations), 1038 (C-O).
1h NMR (600MHz, CDCl
3) δ: 1.059-1.083 (t, 6H, J=7.2 Hz), 2.204 (s, 3H), 2.620-2.655 (q, 4H, J=7.2 Hz), 2.821-2.840 (t, 2H, J=6.0 Hz), 4.276-4.296 (t, 2H, J=6.0 Hz), 7.253-7.275 (m, 1H, J=4.2 Hz, J=2.4 Hz), 7.308-7.322 (d, 2H, J=4.2 Hz, J=2.4 Hz)
Embodiment 19:N, N-piperidyl-2-(2,5-dichloroacetophenone oxime oxygen base) ethamine (compound 7c) synthetic
Brown oily liquids, IR (KBr) υ, cm
-1: IR (KBr) υ, cm
-1: 3061 (Ar-H), 1648 (C=N), 1559,1462 (phenyl ring skeletal vibrations), 1044 (C-O).
1h NMR (600MHz, CDCl
3) δ: 1.432-1.473 (m, 2H, J=6.0 Hz), 1.606-1.644 (m, 4H, J=6.0 Hz), (2.200 s, 3H), 2.526 (s, 4H), 2.734-2.753 (t, 2H, J=6.0 Hz), 4.342-4.361 (t, 2H, J=6.0 Hz), 7.257-7.275 (m, 1H, J=4.2 Hz, J=2.4 Hz), 7.311-7.323 (t, 2H, J=4.2 Hz, J=2.4 Hz)
Embodiment 20:N, N-dimethyl-2-(4-methyl acetophenone oxime oxygen base) ethamine (compound 8a) synthetic
Brown oily liquids, IR (KBr) υ, cm
-1: IR (KBr) υ, cm
-1: 3026 (Ar-H), 1615 (C=N), 1512,1465 (phenyl ring skeletal vibrations), 1038 (C-O).
1h NMR (600MHz, CDCl
3) δ: 2.219 (s, 3H), 2,341 (s, 6H), 2.355 (s, 3H), 2.700-2.719 (t, 2H, J=6.0 Hz), 4.300-4.320 (t, 2H, J=6.0 Hz), 7.157-7.170 (d, 2H, J=7.8 Hz), 7.528-7.541 (d, 2H, J=7.8 Hz)
Embodiment 21:N, N-diethyl-2-(4-methyl acetophenone oxime oxygen base) ethamine (compound 8b) synthetic
Brown oily liquids, IR (KBr) υ, cm
-1: IR (KBr) υ, cm
-1: 3028 (Ar-H), 1612 (C=N), 1515,1453 (phenyl ring skeletal vibrations), 1038 (C-O).
1h NMR (600MHz, CDCl
3) δ: 1.053-1.076 (t, 6H, J=6.0 Hz), 2.209 (s, 3H), 2.353 (s, 3H), 2.613-2.648 (q, 4H, J=7.2 Hz), 2.829-2.849 (t, 2H, J=6.0 Hz), 4.270-4.290 (t, 2H, J=6.0 Hz), 7.156-7.169 (d, 2H, J=9.0 Hz), 7.530-7.543 (d, 2H, J=7.8 Hz)
Embodiment 22:N, N-piperidyl-2-(4-methyl acetophenone oxime oxygen base) ethamine (compound 8c) synthetic
Brown oily liquids, IR (KBr) υ, cm
-1: IR (KBr) υ, cm
-1: 3055 (Ar-H), 1651 (C=N), 1592,1489,1444 (phenyl ring skeletal vibrations), 1047 (C-O).
1h NMR (600MHz, CDCl
3) δ: 1.413 (s, 2H), 1.591-1.612 (t, 4H, J=6.0 Hz), 2.227 (s, 3H), 2.334 (s, 3H), 2.532 (s, 4H), 2.745-2.765 (t, 2H, J=6.0 Hz), 4.354-4.375 (t, 2H, J=6.0 Hz), 7.156-7.165 (d, 2H, J=6.0 Hz), 7.524-7.533 (d, 2H, J=6.0 Hz)
Embodiment 23:N, N-dimethyl-2-(diphenylketoxime oxygen base) ethamine (compound 9a) synthetic
Brown oily liquids, IR (KBr) υ, cm
-1: IR (KBr) υ, cm
-1: 3056 (Ar-H), 1651 (C=N), 1555,1493,1443 (phenyl ring skeletal vibrations), 1040 (C-O).
1h NMR (600MHz, CDCl
3) δ: 2.256 (s, 6H), 2.663-2.683 (t, 2H, J=6.0 Hz), 4.300-4.320 (t, 2H, J=6.0 Hz), 7.304-7.485 (m, 10H)
Embodiment 24:N, N-dimethyl-2-(4-chlorobenzophenone oxime oxygen base) ethamine (compound 10a) synthetic
Brown oily liquids, IR (KBr) υ, cm
-1: IR (KBr) υ, cm
-1: 3058 (Ar-H), 1651 (C=N), 1589,1486,1439 (phenyl ring skeletal vibrations), 1040 (C-O).
1h NMR (600MHz, CDCl
3) δ: 2.248 (s, 6H), 2.667-2.677 (t, 2H, J=6.0 Hz), 4.312-4.331 (t, 2H, J=6.0 Hz), 7.295-7.471 (m, 9H)
Embodiment 25:N, N-diethyl-2-(4-chlorobenzophenone oxime oxygen base) ethamine (compound 10b) synthetic
Brown oily liquids, IR (KBr) υ, cm
-1: IR (KBr) υ, cm
-1: 3058 (Ar-H), 1647 (C=N), 1595,1486,1442 (phenyl ring skeletal vibrations), 1048 (C-O).
1h NMR (600MHz, CDCl
3): 0.995-1.018 (t, 6H, J=6.6 Hz), 2.543-2.579 (q, 4H, J=7.2 Hz), 2.794-2.815 (t, 2H, J=6.0 Hz), 4.274-4.295 (t, 2H, J=6.0 Hz), 7.281-7.463 (m, 9H)
Embodiment 26:N, N-piperidyl-2-(4-chlorobenzophenone oxime oxygen base) ethamine (compound 10c) synthetic
Brown oily liquids, IR (KBr) υ, cm
-1: IR (KBr) υ, cm
-1: 3056 (Ar-H), 1663 (C=N), 1593,1484,1443 (phenyl ring skeletal vibrations), 1048 (C-O).
1h NMR (600MHz, CDCl
3) δ: 1.418 (s, 2H), 1.550-1.588 (m, 4H, J=6.0 Hz), 2.420 (s, 4H), 2.671-2.694 (t, 2H, J=6.0 Hz), 4.317-4.333 (t, 2H, J=6.0 Hz), (7.313-7.461 m, 9H)
Embodiment 27:N, N-piperidyl-2-(2-chlorobenzophenone oxime oxygen base) ethamine (compound 11c) synthetic
Brown oily liquids, IR (KBr) υ, cm
-1: 3056 (Ar-H), 1671 (C=N), 1595,1565,1497 (phenyl ring skeletal vibrations), 1024 (C-O).
1h NMR (600MHz, CDCl
3) δ: 1.394 (s, 2H), 1.528-1.567 (m, 4H, J=6.0 Hz), 2.404 (s, 4H), 2.691-2.712 (t, 2H, J=6.0 Hz), 4.343-4.364 (t, 2H, J=6.0 Hz), (7.124-7.487 m, 9H)
Embodiment 28:N, N-diethyl-2-(4-bromine diphenylketoxime oxygen base) ethamine (compound 12b) synthetic
Sorrel oily liquids, IR (KBr) υ, cm
-1: IR (KBr) υ, cm
-1: 3058 (Ar-H), 1662 (C=N), 1595,1483,1442 (phenyl ring skeletal vibrations), 1047 (C-O).
1h NMR (600MHz, CDCl
3) δ: 0.981-1.004 (t, 6H, J=6.0 Hz), 2.538-2.573 (q, 4H, J=7.2 Hz), 2.786-2.807 (t, 2H, J=6.0 Hz), 4.271-4.291 (t, 2H, J=6.0 Hz), 7.244-7.557 (m, 9H)
Embodiment 29:N, N-piperidyl-2-(4-nitro benzophenone oxime oxygen base) ethamine (compound 13c) synthetic
Brown oily liquids, IR (KBr) υ, cm
-1: 3061 (Ar-H), 1674 (C=N), 1609,1586,1442 (phenyl ring skeletal vibrations), 1038 (C-O).
1h NMR (600MHz, CDCl
3) δ: 1.421-1.433 (d, 2H, J=7.2 Hz), 1.552-1.572 (t, 4H, J=6.0 Hz), 2.407-2.428 (t, 4H, J=6.0 Hz), 2.665-2.723 (m, 2H, J=6.0 Hz, J=9.0 Hz), 4.341-4.402 (m, 2H, J=6.0 Hz, J=12.0 Hz), 7.322-7.305 (q, 2H), 7.390-7.471 (m, 3H), 7.554-7.568 (d, 1H, J=9.0 Hz), 7.656-7.670 (d, 1H, J=9.0 Hz), 8.167-8.182 (d, 1H, J=9.0 Hz), 8.284-8.298 (d, 1H, J=90 Hz)
Embodiment 30:N, N-piperidyl-2-(methyldiphenyl ketoxime oxygen base) ethamine (compound 14c) synthetic
Brown oily liquids, IR (KBr) υ, cm
-1: 3025 (Ar-H), 1645 (C=N), 1598,1518,1444 (phenyl ring skeletal vibrations), 1050 (C-O).
1h NMR (600MHz, CDCl
3) δ: 1.401-1.429 (t, 2H, J=9.0 Hz), 1.547-1.597 (m, 4H, J=6.0 Hz), (2.351-2.455 q, 7H), 2.705-2.729 (q, 2H, J=7.2 Hz), 4.318-4.351 (q, 2H, J=7.2 Hz), 7.211-7.484 (m, 9H)
Embodiment 31:N, N-piperidyl-2-(4-tertiary butyl diphenylketoxime oxygen base) ethamine (compound 15c) synthetic
Brown oily liquids, IR (KBr) υ, cm
-1: 3055 (Ar-H), 1668 (C=N), 1612,1589,1456 (phenyl ring skeletal vibrations), 1044 (C-O).
1h NMR (600MHz, CDCl
3) δ: 1.290-1.351 (m, 9H), 1.416 (s, 2H), 1.572-1.601 (q, 4H, J=6.0 Hz), 4.334-4.362 (q, 2H, J=6.0 Hz), 7.302-7.418 (m, 9H)
Embodiment 32:N, N-piperidyl-2-(4-chlorobenzophenone oxime oxygen base) ethylamine hydrochloride (compound 10c.HCl) synthetic
By 1.00 g compound Ns, N-piperidyl-2-(4-chlorobenzophenone oxime oxygen base) ethamine (10c) is dissolved in 20 ml anhydrous diethyl ethers, in system, slowly passes into dry HCl gas, has solid to separate out.In the time that solid no longer increases, filter to obtain white solid 0.92g, productive rate 83.2%.
The salt of other form of oxime ether aminated compounds of the present invention is as acetate, phosphoric acid salt, Citrate trianion can be by directly adding corresponding acid to obtain in system, this is understandable for having the professional of chemosynthesis knowledge background, and therefore building-up process differs and one illustrates.
Compound activity test
Embodiment 33: impact and composite use that oxime ether aminated compounds of the present invention is taken root on Mung Bean Cuttings
Select full mung bean seed, rinse 1h with clear water, distilled water flushing 10 min, then with 70% alcohol immersion 1 min sterilization, then use distilled water flushing 20 min, are finally immersed in 12 h in distilled water.Select the mung bean seed sowing of germinateing consistent in wet sand, be then positioned in growth cabinet and cultivate, temperature is controlled at 25 ± 1 ℃, and relative humidity is 70%, illumination 16h/ days.Cultivate after 5 days, choose growing way, cotyledon size, Xia Pei axle thickness consistent, the seedling of height of seedling 8-9 cm, hypocotyl and the root system of the following 4cm of excision cotyledon, obtain mung bean adventive root and test cutting.
In water, add tween 80, be made into 0.1% solution, then target compound is dissolved in in 0.1% tween 80 solution, to be made into be the solution of 50 mg/L.Using the 0.1% tween 80 aqueous solution as blank group (CK).In addition, using the 3-indolebutyric acid (IBA) of 0.1% tween 80 solution preparation 10mg/L and the naphthylacetic acid (NAA) of 10mg/L as other control group.IBA and NAA are conventional commercialization auxins root-growing agents, and this class material has good taking root and promotes activity, but concentration use range is narrower, generally, mung bean is imposed to 20 mg/L and just can produce above poisoning.
Above-mentioned cutting is inserted respectively in the invention compound solution containing different concns, liquor capacity 110 mL, the degree of depth 3.5 cm, insert 5 cuttings, repeat 5 times for every bottle.Then be placed in growth cabinet, control temperature at 25 ± 1 ℃, relative humidity 70%, after 24 h,, then whole Mung Bean Cuttings are reentered in distilled water and are cultivated to remove surperficial medicament with distilled water flushing cutting, culture condition is with consistent above, change water every day one time, within 5 days, add up afterwards the number of the adventive root of each Mung Bean Cuttings.
The impact that table 1 the compounds of this invention is taken root on Mung Bean Cuttings
| Treat reagent agent | Drug concentration (mg/L) | Radical (individual) | Average root long (mm) | Take root highly (cm) |
| CK | 0 | 6.89±0.75 | 4.60±0.55 | 0.32±0.05 |
| IBA | 10 | 28.75±2.46 | 3.43±0.44 | 1.78±0.13 |
| NAA | 10 | 25.11±2.12 | 4.65±0.45 | 1.42±0.13 |
| 1c | 50 | 6.29±0.58 | 8.04±0.67 | 0.26±0.02 |
| 2a | 50 | 10.33±0.67 | 1.93±0.71 | 0.32±0.03 |
| 2b | 50 | 9.86±0.67 | 6.07±0.47 | 0.40±0.12 |
| 2c | 50 | 7.67±0.55 | 5.98±0.58 | 0.30±0.03 |
| 3a | 50 | 9.54±0.44 | 4.29±0.28 | 0.89±0.09 |
| 3b | 50 | 10.02±0.94 | 4.52±0.36 | 0.95±0.21 |
| 3c | 50 | 8.07±0.54 | 3.62±0.24 | 0.59±0.07 |
| 4a | 50 | 9.29±0.23 | 3.74±0.25 | 0.63±0.05 |
| 4b | 50 | 10.50±0.65 | 4.56±0.54 | 0.58±0.13 |
| 4c | 50 | 11.43±0.41 | 4.64±0.61 | 0.56±0.05 |
| 5a | 50 | 8.29±0.40 | 5.59±0.36 | 0.43±0.04 |
| 5b | 50 | 12.50±0.67 | 5.70±0.42 | 0.94±0.05 |
| 5c | 50 | 12.43±0.41 | 5.39±0.24 | 0.48±0.06 |
| 6a | 50 | 8.65±0.66 | 5.19±0.45 | 0.53±0.04 |
| 6b | 50 | 9.33±0.81 | 5.62±0.53 | 0.55±0.02 |
| 6c | 50 | 10.29±0.89 | 6.11±0.26 | 0.51±0.05 |
| 7a | 50 | 11.71±0.87 | 6.66±0.42 | 0.50±0.02 |
| 7b | 50 | 16.86±1.12 | 5.07±0.34 | 0.76±0.04 |
| 7c | 50 | 11.33±0.93 | 6.07±0.48 | 0.41±0.03 |
| 8a | 50 | 10.71±0.82 | 6.09±0.27 | 0.43±0.03 |
| 8b | 50 | 11.50±1.05 | 6.08±0.37 | 0.50±0.06 |
| 8c | 50 | 14.68±2.05 | 6.33±0.45 | 1.31±0.94 |
| 9a | 50 | 7.51±0.56 | 7.07±0.64 | 0.36±0.04 |
| 10a | 50 | 8.80±0.48 | 7.45±0.58 | 0.36±0.02 |
| 10b | 50 | 13.13±0.95 | 6.72±0.66 | 0.67±0.05 |
| 10c | 50 | 24.50±2.13 | 7.11±0.74 | 1.27±0.11 |
| 11c | 50 | 10.22±1.08 | 6.54±0.54 | 0.44±0.03 |
| 12b | 50 | 20.47±1.94 | 6.69±0.68 | 1.43±0.12 |
| 13c | 50 | 15.22±1.45 | 6.34±0.56 | 0.55±0.04 |
| 14c | 50 | 11.13±1.21 | 6.81±0.71 | 0.66±0.05 |
| 15c | 50 | 10.17±1.01 | 6.22±0.65 | 0.45±0.04 |
In addition, the oxime ether aminated compounds of different concns has obvious otherness to the formation of Mung Bean Cuttings adventive root.
The impact that table 2 different concns 10c is taken root on Mung Bean Cuttings
With respect to blank group, oxime ether aminated compounds of the present invention has the general promoter action of taking root to mung bean hypocotyl cutting, radical to mung bean hypocotyl and/or root length have certain facilitation effect, the oxime ether aminated compounds that contains substituted diphenylamine structure, especially obvious to the promoter action of taking root of mung bean hypocotyl cutting.Take compound 10c as example, it is apparently higher than blank group aspect radical, average root length and the height of taking root, and radical promotion rate is 255%, the long promotion rate 54% of root, the height promotion rate 296% of taking root.Similar to commercially available auxins root-inducing promoter IBA activity, and be obviously better than IBA aspect the long promotion of root.
Again, oxime ether aminated compounds of the present invention and the composite use of auxin substance can improve growth-promoting root efficiency.
The impact that table 3 oxime ether of the present invention aminated compounds 10c and IBA and the composite use of NAA are taken root on Mung Bean Cuttings
| Spraying medicine concentration | Radical (individual) | Average root long (mm) | Take root highly (cm) |
| CK | 6.89±0.75 | 4.60±0.55 | 0.32±0.05 |
| 10?mg/L?IBA | 28.75±2.46 | 3.43±0.44 | 1.78±0.13 |
| 10?mg/L?NAA | 25.11±2.12 | 4.65±0.45 | 1.42±0.13 |
| 50?mg/L?10c | 24.50±2.13 | 7.11±0.74 | 1.27±0.11 |
| 50?mg/L?10c+10?mg/L?IBA | 39.25±3.95 | 6.71±0.62 | 1.93±0.16 |
| 50?mg/L?10c?+?10?mg/L?NAA | 33.48±3.11 | 5.13±0.51 | 1.52±0.14 |
During with the composite use of IBA, oxime ether aminated compounds of the present invention shows better growth-promoting root activity, and desired concn is lower.By composite dispenser, can promote better the formation of adventive root.
Again, oxime ether aminated compounds of the present invention has aftereffect.Along with the prolongation of incubation time, long continuation of the root of blank and IBA control group extends, and generates lateral root from existing adventive root.Oxime ether aminated compounds of the present invention, along with the prolongation of incubation time, can continue inducing adventitious root and extend, and this has very important effect to expanding explant root system.Take compound 10c as example, cultivate after 5 days equally, average root is long is 7.11mm, and the average root length after 7 days is 9.45mm, and root length has obvious increase.
In addition, test finds that the formation of salt pair adventive root and the oxime ether aminated compounds of salt-independent shape of oxime ether aminated compounds of the present invention have same promoter action.
The impact that the hydrochloride (10b.HCl) of table 4 the compounds of this invention 10b is taken root on Mung Bean Cuttings
| Treat reagent agent | Drug concentration (mg/L) | Radical (individual) | Average root long (mm) | Take root highly (cm) |
| CK | 0 | 6.89±0.75 | 4.60±0.55 | 0.32±0.05 |
| 10b.HCl | 50 | 13.18±1.33 | 6.92±0.56 | 0.64±0.06 |
Embodiment 34: the impact of the compounds of this invention on chrysanthemum cuttage rooting:
Take Cut Flower Chrysanthemum Morifolium " ten thousand contain " as vegetable material.On maternal plant, adopt even thickness side shoot, stay top not launch leaf and 2 and launch leaf completely, remove other and launch leaf, cut sth. askew as 10cm with cutter, be chrysanthemum cuttings.Cuttings base portion is immersed in to the compounds of this invention 10b concentration of 0.1% tween 80 dilution and is followed successively by 100 mg/L and 200 mg/L, 400 mg/L, in the solution of 1000 mg/L, after 5min, take out, clear water is cleaned after base portion residual drug, inserts and is equipped with in the cutting bed of fine sand, is placed in hot-house culture, temperature 20-25 ℃, humidity 80%.Regularly water, cultivate after 30 days, take out cuttings and measure radical, the data such as root length.
The impact of table 5 the compounds of this invention 10b on chrysanthemum cuttage rooting
| Concentration (mg/L) | Mean elements | Average root long (cm) |
| 0 | 45.73±4.43 | 2.41±0.23 |
| 100 | 48.86±4.82 | 3.12±0.31 |
| 200 | 56.12±5.31 | 3.65±0.34 |
| 400 | 65.17±5.44 | 3.48±0.35 |
| 1000 | 77.52±7.52 | 3.34±0.31 |
As mentioned above, the formation of oxime ether aminated compounds of the present invention or its salt pair explant adventive root has promoter action, this compounds separately or its salt or with the composite use of auxins plant growth promoter can promote explant faster and better form adventive root and improve surviving rate.As the novel plant rooting promoter of a class, oxime ether aminated compounds of the present invention or its salt and the composition that comprises oxime ether aminated compounds or its salt are for providing a kind of new possibility in the agriculture production in the fields such as agricultural gardening.
Claims (5)
1. a composition, is characterized in that: in described composition, comprise component A and B component, described component A is the one in following oxime ether aminated compounds: N, N-piperidyl-2-(benzaldoxime oxygen base) ethamine, N, N-dimethyl-2-(4-chlorobenzaldehyde oxime oxygen base) ethamine, N, N-diethyl-2-(4-chlorobenzaldehyde oxime oxygen base) ethamine, N, N-piperidyl-2-(4-chlorobenzaldehyde oxime oxygen base) ethamine, N, N-dimethyl-2-(acetophenone oxime oxygen base) ethamine, N, N-diethyl-2-(acetophenone oxime oxygen base) ethamine, N, N-piperidyl-2-(acetophenone oxime oxygen base) ethamine, N, N-dimethyl-2-(4-fluorophenethyl ketoxime oxygen base) ethamine, N, N-diethyl-2-(4-fluorophenethyl ketoxime oxygen base) ethamine, N, N-piperidyl-2-(4-fluorophenethyl ketoxime oxygen base) ethamine, N, N-dimethyl-2-(4-chloro-acetophenone oxime oxygen base) ethamine, N, N-diethyl-2-(4-chloro-acetophenone oxime oxygen base) ethamine, N, N-piperidyl-2-(4-chloro-acetophenone oxime oxygen base) ethamine, N, N-dimethyl-2-(4-bromoacetophenone oxime oxygen base) ethamine, N, N-diethyl-2-(4-bromoacetophenone oxime oxygen base) ethamine, N, N-piperidyl-2-(4-bromoacetophenone oxime oxygen base) ethamine, N, N-dimethyl-2-(2,5-dichloroacetophenone oxime oxygen base) ethamine, N, N-diethyl-2-(2,5-dichloroacetophenone oxime oxygen base) ethamine, N, N-piperidyl-2-(2,5-dichloroacetophenone oxime oxygen base) ethamine, N, N-dimethyl-2-(4-methyl acetophenone oxime oxygen base) ethamine, N, N-diethyl-2-(4-methyl acetophenone oxime oxygen base) ethamine, N, N-piperidyl-2-(4-methyl acetophenone oxime oxygen base) ethamine, N, N-dimethyl-2-(diphenylketoxime oxygen base) ethamine, N, N-dimethyl-2-(4-chlorobenzophenone oxime oxygen base) ethamine, N, N-diethyl-2-(4-chlorobenzophenone oxime oxygen base) ethamine, N, N-piperidyl-2-(4-chlorobenzophenone oxime oxygen base) ethamine, N, N-piperidyl-2-(2-chlorobenzophenone oxime oxygen base) ethamine, N, N-diethyl-2-(4-bromine diphenylketoxime oxygen base) ethamine, N, N-piperidyl-2-(4-nitro benzophenone oxime oxygen base) ethamine, N, N-piperidyl-2-(methyldiphenyl ketoxime oxygen base) ethamine and N, N-piperidyl-2-(4-tertiary butyl diphenylketoxime oxygen base) ethamine, or the salt of above-mentioned oxime ether aminated compounds, described salt is hydrochloride, acetate, phosphoric acid salt or Citrate trianion, described B component is auxins plant growth promoter.
2. composition according to claim 1, is characterized in that: described B component is 3-indolebutyric acid.
3. oxime ether aminated compounds, as the application of plant rooting promoter, is characterized in that: described oxime ether aminated compounds is the one in following compound: N, N-piperidyl-2-(benzaldoxime oxygen base) ethamine, N, N-dimethyl-2-(4-chlorobenzaldehyde oxime oxygen base) ethamine, N, N-diethyl-2-(4-chlorobenzaldehyde oxime oxygen base) ethamine, N, N-piperidyl-2-(4-chlorobenzaldehyde oxime oxygen base) ethamine, N, N-dimethyl-2-(acetophenone oxime oxygen base) ethamine, N, N-diethyl-2-(acetophenone oxime oxygen base) ethamine, N, N-piperidyl-2-(acetophenone oxime oxygen base) ethamine, N, N-dimethyl-2-(4-fluorophenethyl ketoxime oxygen base) ethamine, N, N-diethyl-2-(4-fluorophenethyl ketoxime oxygen base) ethamine, N, N-piperidyl-2-(4-fluorophenethyl ketoxime oxygen base) ethamine, N, N-dimethyl-2-(4-chloro-acetophenone oxime oxygen base) ethamine, N, N-diethyl-2-(4-chloro-acetophenone oxime oxygen base) ethamine, N, N-piperidyl-2-(4-chloro-acetophenone oxime oxygen base) ethamine, N, N-dimethyl-2-(4-bromoacetophenone oxime oxygen base) ethamine, N, N-diethyl-2-(4-bromoacetophenone oxime oxygen base) ethamine, N, N-piperidyl-2-(4-bromoacetophenone oxime oxygen base) ethamine, N, N-dimethyl-2-(2,5-dichloroacetophenone oxime oxygen base) ethamine, N, N-diethyl-2-(2,5-dichloroacetophenone oxime oxygen base) ethamine, N, N-piperidyl-2-(2,5-dichloroacetophenone oxime oxygen base) ethamine, N, N-dimethyl-2-(4-methyl acetophenone oxime oxygen base) ethamine, N, N-diethyl-2-(4-methyl acetophenone oxime oxygen base) ethamine, N, N-piperidyl-2-(4-methyl acetophenone oxime oxygen base) ethamine, N, N-dimethyl-2-(diphenylketoxime oxygen base) ethamine, N, N-dimethyl-2-(4-chlorobenzophenone oxime oxygen base) ethamine, N, N-diethyl-2-(4-chlorobenzophenone oxime oxygen base) ethamine, N, N-piperidyl-2-(4-chlorobenzophenone oxime oxygen base) ethamine, N, N-piperidyl-2-(2-chlorobenzophenone oxime oxygen base) ethamine, N, N-diethyl-2-(4-bromine diphenylketoxime oxygen base) ethamine, N, N-piperidyl-2-(4-nitro benzophenone oxime oxygen base) ethamine, N, N-piperidyl-2-(methyldiphenyl ketoxime oxygen base) ethamine and N, N-piperidyl-2-(4-tertiary butyl diphenylketoxime oxygen base) ethamine.
4. the salt of oxime ether aminated compounds, as the application of plant rooting promoter, is characterized in that: described oxime ether aminated compounds is the one in following compound: N, N-piperidyl-2-(benzaldoxime oxygen base) ethamine, N, N-dimethyl-2-(4-chlorobenzaldehyde oxime oxygen base) ethamine, N, N-diethyl-2-(4-chlorobenzaldehyde oxime oxygen base) ethamine, N, N-piperidyl-2-(4-chlorobenzaldehyde oxime oxygen base) ethamine, N, N-dimethyl-2-(acetophenone oxime oxygen base) ethamine, N, N-diethyl-2-(acetophenone oxime oxygen base) ethamine, N, N-piperidyl-2-(acetophenone oxime oxygen base) ethamine, N, N-dimethyl-2-(4-fluorophenethyl ketoxime oxygen base) ethamine, N, N-diethyl-2-(4-fluorophenethyl ketoxime oxygen base) ethamine, N, N-piperidyl-2-(4-fluorophenethyl ketoxime oxygen base) ethamine, N, N-dimethyl-2-(4-chloro-acetophenone oxime oxygen base) ethamine, N, N-diethyl-2-(4-chloro-acetophenone oxime oxygen base) ethamine, N, N-piperidyl-2-(4-chloro-acetophenone oxime oxygen base) ethamine, N, N-dimethyl-2-(4-bromoacetophenone oxime oxygen base) ethamine, N, N-diethyl-2-(4-bromoacetophenone oxime oxygen base) ethamine, N, N-piperidyl-2-(4-bromoacetophenone oxime oxygen base) ethamine, N, N-dimethyl-2-(2,5-dichloroacetophenone oxime oxygen base) ethamine, N, N-diethyl-2-(2,5-dichloroacetophenone oxime oxygen base) ethamine, N, N-piperidyl-2-(2,5-dichloroacetophenone oxime oxygen base) ethamine, N, N-dimethyl-2-(4-methyl acetophenone oxime oxygen base) ethamine, N, N-diethyl-2-(4-methyl acetophenone oxime oxygen base) ethamine, N, N-piperidyl-2-(4-methyl acetophenone oxime oxygen base) ethamine, N, N-dimethyl-2-(diphenylketoxime oxygen base) ethamine, N, N-dimethyl-2-(4-chlorobenzophenone oxime oxygen base) ethamine, N, N-diethyl-2-(4-chlorobenzophenone oxime oxygen base) ethamine, N, N-piperidyl-2-(4-chlorobenzophenone oxime oxygen base) ethamine, N, N-piperidyl-2-(2-chlorobenzophenone oxime oxygen base) ethamine, N, N-diethyl-2-(4-bromine diphenylketoxime oxygen base) ethamine, N, N-piperidyl-2-(4-nitro benzophenone oxime oxygen base) ethamine, N, N-piperidyl-2-(methyldiphenyl ketoxime oxygen base) ethamine and N, N-piperidyl-2-(4-tertiary butyl diphenylketoxime oxygen base) ethamine, described salt is hydrochloride, acetate, phosphoric acid salt or Citrate trianion.
5. the composition described in claim 1 or 2 is as the application of plant rooting promoter.
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| US4352804A (en) * | 1978-07-25 | 1982-10-05 | Acf Chemiefarma Nv | Oxime ethers, their preparation and pharmaceutical compositions containing them |
| CN1251575A (en) * | 1997-04-01 | 2000-04-26 | 住友化学工业株式会社 | Oxime ether compounds, their use and intermediates for preparing same |
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| US4352804A (en) * | 1978-07-25 | 1982-10-05 | Acf Chemiefarma Nv | Oxime ethers, their preparation and pharmaceutical compositions containing them |
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