CN102070628B - 4-alkyl-6-aryl-5-(1, 2, 4-triazole-1-yl)-2-amino-1, 3-thiazine and application thereof - Google Patents
4-alkyl-6-aryl-5-(1, 2, 4-triazole-1-yl)-2-amino-1, 3-thiazine and application thereof Download PDFInfo
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Abstract
The invention discloses 4-alkyl-6-aryl-5-(1, 2, 4-triazole-1-yl)-2-amino-1, 3-thiazine shown as a chemical structural formula I and salts thereof. A method for preparing the 4-alkyl-6-aryl-5-(1, 2, 4-triazole-1-yl)-2-amino-1, 3-thiazine has the following steps: heating 1-aryl-2-(1, 2, 4-triazole-1-yl)-3-alkyl-1-propylene-3-ketone and thiourea in ethanol, stirring materials for reaction, using ammonia for neutralization, and preparing and obtaining the 4-alkyl-6-aryl-5-(1, 2, 4-triazole-1-yl)-2-amino-1, 3-thiazine through reduced pressure distillation and column chromatography. The invention also discloses application of the 4-alkyl-6-aryl-5-(1, 2, 4-triazole-1-yl)-2-amino-1, 3-thiazine to the preparation of pesticide.
Description
Technical field
The present invention relates to one type of new compound, specifically is that 4-alkyl-6-aryl-5-(1,2, the 4-triazol-1-yl)-2-is amino-1, the 3-thiazine.
Background technology
The azole Hete rocyclic derivatives is high with its good biological activity and drug effect; Fungicidal spectrum is wide; Characteristics such as interior absorption is good receive medicine and agricultural chemicals worker's attention [Comperhensive Heterocylic Chemistry.Pergamon Oxford, 1983 always very much; 5:733-735], and triazole class is wherein comparatively influential one type.The bactericidal mechanism of triazole class sterilant is the formation that influences fungal cell wall through the biosynthesizing that hinders the fungi ergosterol, and most fungal diseases that damage to crops is grown all have good control effect.The triazole class sterilant has certain plant growth regulating activity [agricultural chemicals, 1994,33 (4): 19-20 simultaneously; J Med Chem, 1996,39 (12): 842-849],, eliminate the plant apical dominance, multiple functions such as having raising the output, precocity, resist, be degeneration-resistant through suppressing the synthetic of plant materials inner gibberellin.The triazole class sterilant is compared with other sterilant, has characteristics such as efficient, wide spectrum, low toxicity, low resistance, economic benefits and social benefits property (sterilization, control long), becomes the most promising sterilant type [agricultural chemicals, 1989,28 (1): 48-52].Shao Ling etc. have described 4-aryl-5-triazolyl thiazole-2-imine compound apple wheel line bacterium have been had fungicidal activity (SCI, 2007,28,270).The 4-tertiary butyl-5-(1,2, the 4-triazol-1-yl)-2-benzyl imino-thiazole preparation and fungicidal activity, insecticidal activity and anti-tumor activity are described [organic chemistry, 2010,30 (6): 923-927; CN101602761; CN201010290133.9; CN101836979].
4-alkyl-6-aryl-5-(1,2, the 4-triazol-1-yl)-2-amino-1, the preparation of 3-thiazine and insecticidal activity thereof be report not.
Summary of the invention
The object of the present invention is to provide 4-alkyl-6-aryl-5-shown in the chemical structural formula I (1,2, the 4-triazol-1-yl)-2-amino-1,3-thiazine and salt thereof:
Wherein, X is selected from: 2-chlorine, 2-fluorine, 2-hydroxyl, 2-methoxyl group, 2-oxyethyl group, 2-nitro, 3-dimethylamino, 3-chlorine, 3-bromine, 3-fluorine, 3-methyl, 3-ethyl, 3-trifluoromethyl, 3-hydroxyl, 3-methoxyl group, 3-oxyethyl group, 3-nitro, 3-sulfonic group, 3-methanesulfonamido, 3-sulfamyl, 4-dimethylamino, 4-chlorine, 4-bromine, 4-fluorine, 4-methyl, 4-ethyl, 4-trifluoromethyl, 4-hydroxyl, 4-methoxyl group, 4-oxyethyl group, 4-acetoxyl group, 4-nitro, 4-sulfonic group, 4-methanesulfonamido, 4-sulfamyl, 2-chloro-5-nitro, 3-ethyl-4-hydroxyl, 3; 4-dimethoxy or 2; 4, the 5-trimethoxy; R is selected from: C
1～C
2Alkyl, C
3～C
4Straight chained alkyl or branched-chain alkyl; Salt is selected from: hydrochloride, hydrobromate, vitriol, phosphoric acid salt or nitrate salt.
The objective of the invention is to also provide the 4-alkyl-6-aryl-5-shown in the formula I (1,2, the 4-triazol-1-yl)-2-amino-1, the preparation method of 3-thiazine, its preparation comprises the steps:
(1) 1-chloro-2-alkyl ethyl ketone, 1,2, the 4-triazole is dissolved in the ethyl acetate solution, and salt of wormwood is done acid binding agent; PEG600 makes phase-transfer catalyst, and stirring, back flow reaction 4～5h filter, and add 65% nitric acid and obtain white solid; White solid places ETHYLE ACETATE, drips 30% sodium hydroxide solution to dissolving, separatory; Underpressure distillation gets 1-(1,2, the 4-triazol-1-yl)-2-alkyl ethyl ketone; Preparation is undertaken by following reaction formula:
(2) 1-(1,2, the 4-triazol-1-yl)-2-alkyl ethyl ketone and aromatic aldehyde are in toluene, and piperidines catalysis reaction 5～8h down makes 1-aryl-2-(1,2, the 4-triazol-1-yl)-3-alkyl-1-propylene-3-ketone; Preparation is undertaken by following reaction formula:
(3) 1-aryl-2-(1,2, the 4-triazol-1-yl)-3-alkyl-1-propylene-3-ketone and thiocarbamide heat in ethanol, stirring reaction, and the ammoniacal liquor neutralization through underpressure distillation and column chromatography, gets 4-alkyl-6-aryl-5-(1,2, the 4-triazol-1-yl)-2-amino-1, the 3-thiazine; Preparation is undertaken by following reaction formula:
The objective of the invention is to also provide described 4-alkyl-6-aryl-5-(1,2, the 4-triazol-1-yl)-2-amino-1, the 3-thiazine is the 4-tertiary butyl-6-(4-p-methoxy-phenyl)-5-(1,2, the 4-triazol-1-yl)-2-amino-1, the 3-thiazine:
The objective of the invention is to also provide described 4-alkyl-6-aryl-5-(1,2, the 4-triazol-1-yl)-2-amino-1,3-thiazine salt is the 4-tertiary butyl-6-(4-chloro-phenyl-)-5-(1,2, the 4-triazol-1-yl)-2-amino-1,3-thiazine hydrochloride:
The objective of the invention is to also provide described 4-alkyl-6-aryl-5-(1,2, the 4-triazol-1-yl)-2-amino-1, the 3-thiazine is the 4-tertiary butyl-6-(2-p-methoxy-phenyl)-5-(1,2, the 4-triazol-1-yl)-2-amino-1, the 3-thiazine:
The objective of the invention is to also provide described 4-alkyl-6-aryl-5-(1,2, the 4-triazol-1-yl)-2-amino-1, the 3-thiazine is the 4-tertiary butyl-6-(4-aminomethyl phenyl)-5-(1,2, the 4-triazol-1-yl)-2-amino-1, the 3-thiazine:
The objective of the invention is to also provide described 4-alkyl-6-aryl-5-(1,2, the 4-triazol-1-yl)-2-amino-1, the 3-thiazine is the 4-tertiary butyl-6-(2-chloro-5-nitrophenyl)-5-(1,2, the 4-triazol-1-yl)-2-amino-1, the 3-thiazine:
4-alkyl-6-aryl-the 5-that the object of the present invention is to provide (1,2, the 4-triazol-1-yl)-2-amino-1, the 3-thiazine has insecticidal activity, can be used for preparing sterilant.
The present invention compared with prior art has following advantage:
1. the present invention has prepared 4-alkyl-6-aryl-5-(1,2, the 4-triazol-1-yl)-2-amino-1,3-thiazine (I) first.
2.4-alkyl-6-aryl-5-(1,2, the 4-triazol-1-yl)-2-amino-1,3-thiazine (I) has insecticidal activity, can be used for preparing sterilant.
Embodiment
Following examples are intended to explain the present invention rather than to further qualification of the present invention.
The embodiment 14-tertiary butyl-6-(4-p-methoxy-phenyl)-5-(1,2, the 4-triazol-1-yl)-2-amino-1, the preparation of 3-thiazine
The preparation of (1) 3,3-dimethyl--1-(1,2, the 4-triazol-1-yl)-2-butanone
One chloropinacolone (0.05mol), 1,2,4-triazole (0.05mmol), salt of wormwood (0.10mol), catalytic amount PEG600, ETHYLE ACETATE (60mL) stirring and refluxing, reaction 5.0h filters, and in filtrating, drips 60%HNO
3(0.05mol) salify filters, and filter cake places ETHYLE ACETATE, dropping ammonia, and the solid dissolving, separatory, drying, distillating recovering solvent gets 3,3-dimethyl--1-(1,2, the 4-triazol-1-yl)-2-butanone; Productive rate 85.6%, 60～62 ℃ of fusing points.
The preparation of (2) 4,4-dimethyl--1-(4-p-methoxy-phenyl)-2-(1,2, the 4-triazol-1-yl)-1-penten-3-one
3,3-dimethyl--1-(1,2, the 4-triazol-1-yl)-2-butanone (0.011mol), piperidines (0.1mL), toluene (30mL); Drip 4-methoxybenzaldehyde (0.010mol) toluene solution (20mL), stirring and refluxing, reaction 8h, reaction solution is through 3 * 50mL washing; Separatory, drying, distillating recovering solvent gets yellow dope 4; 4-dimethyl--1-(4-p-methoxy-phenyl)-2-(1,2, the 4-triazol-1-yl)-1-penten-3-one.
(3) the 4-tertiary butyl-6-(4-p-methoxy-phenyl)-5-(1,2, the 4-triazol-1-yl)-2-amino-1, the preparation of 3-thiazine
4,4-dimethyl--1-(4-p-methoxy-phenyl)-2-(1,2; The 4-triazol-1-yl)-and 1-penten-3-one, thiocarbamide (0.011mol), ethanol (60ml), stirring and refluxing, reaction 24h; Add the ammoniacal liquor neutralization, underpressure distillation and column chromatography get the 4-tertiary butyl-6-(4-p-methoxy-phenyl)-5-(1; 2, the 4-triazol-1-yl)-2-amino-1, the 3-thiazine; 157～160 ℃ of fusing points;
1H NMR (CDCl
3, 400MHz), δ: 1.03 (s, 9H, 3 * CH
3), 3.77 (s, 3H, CH
3), 4.50 (s, 1H, thiazine ring 6-H), 4.84 (bs, 2H, NH
2), 6.81 (d, J=8.4Hz, C
6H
42,6-H), 7.09 (d, J=8.8Hz, C
6H
43,5-H), 7.83 (s, 1H, C
2H
2N
33-H), 7.97 (s, 1H, C
2H
2N
35-H).
The embodiment 24-tertiary butyl-6-(4-chloro-phenyl-)-5-(1,2, the 4-triazol-1-yl)-2-amino-1, the preparation of 3-thiazine hydrochloride
The preparation of (1) 4,4-dimethyl--1-(4-chloro-phenyl-)-2-(1,2, the 4-triazol-1-yl)-1-penten-3-one
3,3-dimethyl--1-(1,2, the 4-triazol-1-yl)-2-butanone (0.011mol), piperidines (0.1mL), toluene (30mL); Drip 4-chlorobenzaldehyde (0.010mol) toluene solution (20mL), stirring and refluxing, reaction 8h; Reaction solution is with 3 * 50mL washing, and separatory and distillating recovering solvent get yellow dope 4; 4-dimethyl--1-(4-chloro-phenyl-)-2-(1,2, the 4-triazol-1-yl)-1-penten-3-one.
(2) the 4-tertiary butyl-6-(4-chloro-phenyl-)-5-(1,2, the 4-triazol-1-yl)-2-amino-1, the preparation of 3-thiazine hydrochloride
4,4-dimethyl--1-(4-chloro-phenyl-)-2-(1,2, the 4-triazol-1-yl)-1-penten-3-one, thiocarbamide (0.011mol), ethanol (60ml), stirring and refluxing, reaction 6h.Solid is separated out in cooling, filters, the dry 4-tertiary butyl-6-(4-chloro-phenyl-)-5-(1,2, the 4-triazol-1-yl)-2-amino-1, the 3-thiazine hydrochloride of getting; Fusing point＞300 ℃;
1H NMR (CDCl
3, 400MHz), δ: 1.10 (s, 9H, 3 * CH
3), 5.22 (s, 1H, thiazine ring 6-H), 7.37 (d, J=8.0Hz, C
6H
42,6-H), 7.47 (d, J=8.0Hz, C
6H
43,5-H), 8.13 (s, 1H, C
2H
2N
33-H), 8.77 (s, 1H, C
2H
2N
35-H), 10.39 (bs, 2H, NH
2), 11.77 (bs, 1H, HCl).
The embodiment 34-tertiary butyl-6-(2-p-methoxy-phenyl)-5-(1,2, the 4-triazol-1-yl)-2-amino-1, the preparation of 3-thiazine
The preparation of (1) 4,4-dimethyl--1-(2-p-methoxy-phenyl)-2-(1,2, the 4-triazol-1-yl)-1-penten-3-one
3,3-dimethyl--1-(1,2, the 4-triazol-1-yl)-2-butanone (0.011mol), piperidines (0.1mL), toluene (30mL); Drip 4-chlorobenzaldehyde (0.010mol) toluene solution (20mL), stirring and refluxing, reaction 7h, reaction solution is through 3 * 50mL washing; Separatory, drying, distillating recovering solvent gets yellow dope 4; 4-dimethyl--1-(2-p-methoxy-phenyl)-2-(1,2, the 4-triazol-1-yl)-1-penten-3-one.
(2) the 4-tertiary butyl-6-(2-p-methoxy-phenyl)-5-(1,2, the 4-triazol-1-yl)-2-amino-1, the preparation of 3-thiazine
4,4-dimethyl--1-(2-p-methoxy-phenyl)-2-(1,2; The 4-triazol-1-yl)-and 1-penten-3-one, thiocarbamide (0.011mol), ethanol (60ml), stirring and refluxing, reaction 24h; Add the ammoniacal liquor neutralization, underpressure distillation and column chromatography get the 4-tertiary butyl-6-(2-p-methoxy-phenyl)-5-(1; 2, the 4-triazol-1-yl)-2-amino-1, the 3-thiazine; 161～163 ℃ of fusing points;
1H NMR (CDCl
3, 400MHz), δ: 1.05 (s, 9H, 3 * CH
3), 3.77 (s, 3H, CH
3), 4.81 (bs, 2H, NH
2), 4.94 (s, 1H, thiazine ring 6-H), 6.82～7.25 (m, 4H, C
6H
4), 7.89 (s, 1H, C
2H
2N
33-H), 7.96 (s, 1H, C
2H
2N
35-H).
The embodiment 4 4-tertiary butyl-6-(4-aminomethyl phenyl)-5-(1,2, the 4-triazol-1-yl)-2-amino-1, the preparation of 3-thiazine
The preparation of (1) 4,4-dimethyl--1-(4-aminomethyl phenyl)-2-(1,2, the 4-triazol-1-yl)-1-penten-3-one
3,3-dimethyl--1-(1,2, the 4-triazol-1-yl)-2-butanone (0.011mol), piperidines (0.1mL), toluene (30mL); Drip 4-tolyl aldehyde (0.010mol) toluene solution (20mL), stirring and refluxing, reaction 6h, reaction solution is through 3 * 50mL washing; Separatory, drying, distillating recovering solvent gets yellow dope 4; 4-dimethyl--1-(2-p-methoxy-phenyl)-2-(1,2, the 4-triazol-1-yl)-1-penten-3-one.
(2) the 4-tertiary butyl-6-(4-aminomethyl phenyl)-5-(1,2, the 4-triazol-1-yl)-2-amino-1, the preparation of 3-thiazine
4,4-dimethyl--1-(4-aminomethyl phenyl)-2-(1,2; The 4-triazol-1-yl)-and 1-penten-3-one, thiocarbamide (0.011mol), ethanol (60ml), stirring and refluxing, reaction 24h; Add the ammoniacal liquor neutralization, underpressure distillation and column chromatography get the 4-tertiary butyl-6-(4-aminomethyl phenyl)-5-(1; 2, the 4-triazol-1-yl)-2-amino-1, the 3-thiazine; 134～135 ℃ of fusing points;
1H NMR (CDCl
3, 400MHz), δ: 1.03 (s, 9H, 3 * CH
3), 2.30 (s, 3H, CH
3), 4.50 (s, 1H,, thiazine ring 6-H) and, 4.83 (bs, 2H, NH
2), 7.04 (d, J=8.4Hz, C
6H
42,6-H), 7.09 (d, J=8.4Hz, C
6H
43,5-H), 7.82 (s, 1H, C
2H
2N
33-H), 7.97 (s, 1H, C
2H
2N
35-H).
The embodiment 5 4-tertiary butyl-6-(2-chloro-5-nitrophenyl)-5-(1,2, the 4-triazol-1-yl)-2-amino-1, the preparation of 3-thiazine
The preparation of (1) 4,4-dimethyl--1-(2-chloro-5-nitrophenyl)-2-(1,2, the 4-triazol-1-yl)-1-penten-3-one
3,3-dimethyl--1-(1,2, the 4-triazol-1-yl)-2-butanone (0.011mol), piperidines (0.1mL), toluene (30mL); Drip 4-tolyl aldehyde (0.010mol) toluene solution (20mL), stirring and refluxing, reaction 6h, reaction solution is through 3 * 50mL washing; Separatory, drying, distillating recovering solvent gets pale brown look solid 4; 4-dimethyl--1-(2-chloro-5-nitrophenyl)-2-(1,2, the 4-triazol-1-yl)-1-penten-3-one.
(2) the 4-tertiary butyl-6-(2-chloro-5-nitrophenyl)-5-(1,2, the 4-triazol-1-yl)-2-amino-1, the preparation of 3-thiazine
4,4-dimethyl--1-(2-chloro-5-nitrophenyl)-2-(1,2; The 4-triazol-1-yl)-and 1-penten-3-one, thiocarbamide (0.011mol), ethanol (60ml), 70 ℃ of reaction 7h add the ammoniacal liquor neutralization; Underpressure distillation and column chromatography get the 4-tertiary butyl-6-(2-chloro-5-nitrophenyl)-5-(1,2; The 4-triazol-1-yl)-and 2-amino-1,3-thiazine, 190～192 ℃ of fusing points;
1H NMR (CDCl
3, 400MHz), δ: 1.12 (s, 9H, 3 * CH
3), 4.83 (s, 1H, thiazine ring 6-H), 4.91 (bs, 2H, NH
2), 7.54 (d, J=8.8Hz, C
6H
43-H), 7.97 (s, 1H, C
2H
2N
33-H), 8.03 (s, 1H, C
2H
2N
35-H), 8.11 (dd, J=3.2Hz, J=8.8Hz, C
6H
44-H), 8.20 (d, J=3.2Hz, C
6H
46-H).
Embodiment 6 4-alkyl-6-aryl-5-(1,2, the 4-triazol-1-yl)-2-amino-1,3-thiazine and salt pair black bean aphid cytotoxicity thereof
1 supplies the examination target
Black bean aphid (Aphis fabae) is indoor with broad bean seedling raising sensitive strain for many years, and it is if that 3 ages in days are aphid that worm is used in test; Test uses worm to become mite as health.
2 culture condition
Supplying the culture condition of examination target and test back target is 25 ± 5 ℃ of temperature, relative humidity 65 ± 5%, periodicity of illumination 12/12h (L/D).
3 test medicines: 4-alkyl-6-aryl-5-(1,2, the 4-triazol-1-yl)-2-amino-1,3-thiazine or its salt.
4 medicaments are prepared former medicine: take by weighing aequum with ten thousand/electronic balance; Solvent: N, N N (DMF), 0.2%; Emulsifying agent: Tween 80,0.2%; Add clear water and be diluted to desired concn.
5 TPs are with reference to " pesticide bioactivity is estimated SOP ".
The general sieve of black bean aphid adopts pickling process.To have 3 age in days broad beans if the broad bean seedling of aphid is cut, dipping took out after 10 seconds in the soup for preparing, and was inserted on the sponge that suctions water, covered the lampshade that starts, and every processing repeats for 2 times.Dispose, be put into the observation indoor cultivation, regularly observe, inspection and record death condition are calculated mortality ratio behind the 72h.
6 cytotoxicities
4-alkyl-6-aryl-5-(1,2, the 4-triazol-1-yl)-2-amino-1; The cytotoxicity of 3-thiazine or its salt: when effective constituent concentration 500mg/L; Behind the dispenser 72h, the 4-tertiary butyl-6-(4-chloro-phenyl-)-5-(1,2; The 4-triazol-1-yl)-and 2-amino-1,3-thiazine and hydrochloride thereof are 49% to the mortality ratio of black bean aphid.4-alkyl-6-aryl-5-(1,2, the 4-triazol-1-yl)-2-amino-1,3-thiazine or its salt have insecticidal activity, can be used as the preparation sterilant and use.
Claims (8)
1. 4-alkyl-6-aryl-5-shown in the chemical structural formula I (1,2, the 4-triazol-1-yl)-2-is amino-1,3-thiazine and salt thereof:
Wherein, X is selected from: 2-chlorine, 2-fluorine, 2-hydroxyl, 2-methoxyl group, 2-oxyethyl group, 2-nitro, 3-chlorine, 3-bromine, 3-fluorine, 3-methyl, 3-ethyl, 3-trifluoromethyl, 3-hydroxyl, 3-methoxyl group, 3-oxyethyl group, 3-nitro, 4-chlorine, 4-bromine, 4-fluorine, 4-methyl, 4-ethyl, 4-trifluoromethyl, 4-hydroxyl, 4-methoxyl group, 4-oxyethyl group, 4-nitro; R is selected from: C
1～C
2Alkyl, C
3～C
4Straight chained alkyl or branched-chain alkyl; Salt is selected from: hydrochloride, hydrobromate, vitriol, phosphoric acid salt or nitrate salt.
2. the described 4-alkyl-6-aryl-5-of claim 1 (1,2, the 4-triazol-1-yl)-2-is amino-1, the preparation method of 3-thiazine, and its preparation comprises the steps:
(1) 1-chloro-2-alkyl ethyl ketone, 1,2, the 4-triazole is dissolved in the ethyl acetate solution, and salt of wormwood is done acid binding agent; PEG600 makes phase-transfer catalyst, and stirring, back flow reaction 4～5h filter, and add 65% nitric acid and obtain white solid; White solid places ETHYLE ACETATE, drips 30% sodium hydroxide solution to dissolving, separatory; Underpressure distillation gets 1-(1,2, the 4-triazol-1-yl)-2-alkyl ethyl ketone; Preparation is undertaken by following reaction formula:
(2) 1-(1,2, the 4-triazol-1-yl)-2-alkyl ethyl ketone and aromatic aldehyde are in toluene, and piperidines catalysis reaction 5～8h down makes 1-aryl-2-(1,2, the 4-triazol-1-yl)-3-alkyl-1-propylene-3-ketone; Preparation is undertaken by following reaction formula:
(3) 1-aryl-2-(1,2, the 4-triazol-1-yl)-3-alkyl-1-propylene-3-ketone and thiocarbamide heat in ethanol, stirring reaction, and the ammoniacal liquor neutralization through underpressure distillation and column chromatography, gets 4-alkyl-6-aryl-5-(1,2, the 4-triazol-1-yl)-2-amino-1, the 3-thiazine; Preparation is undertaken by following reaction formula:
Wherein, the definition of X and R is according to claim 1 in the reaction formula.
3. the described 4-alkyl-6-aryl-5-of claim 1 (1,2, the 4-triazol-1-yl)-2-is amino-1, and the 3-thiazine is that the 4-tertiary butyl-6-(4-p-methoxy-phenyl)-5-(1,2, the 4-triazol-1-yl)-2-is amino-1, the 3-thiazine:
4. the described 4-alkyl-6-aryl-5-of claim 1 (1,2, the 4-triazol-1-yl)-2-is amino-1, and 3-thiazine salt is that the 4-tertiary butyl-6-(4-chloro-phenyl-)-5-(1,2, the 4-triazol-1-yl)-2-is amino-1,3-thiazine hydrochloride:
5. the described 4-alkyl-6-aryl-5-of claim 1 (1,2, the 4-triazol-1-yl)-2-is amino-1, and the 3-thiazine is that the 4-tertiary butyl-6-(2-p-methoxy-phenyl)-5-(1,2, the 4-triazol-1-yl)-2-is amino-1, the 3-thiazine:
6. the described 4-alkyl-6-aryl-5-of claim 1 (1,2, the 4-triazol-1-yl)-2-is amino-1, and the 3-thiazine is that the 4-tertiary butyl-6-(4-aminomethyl phenyl)-5-(1,2, the 4-triazol-1-yl)-2-is amino-1, the 3-thiazine:
7.4-alkyl-6-aryl-5-(1,2, the 4-triazol-1-yl)-2-amino-1,3-thiazine are the 4-tertiary butyl-6-(2-chloro-5-nitrophenyl)-5-(1,2, the 4-triazol-1-yl)-2-amino-1, the 3-thiazine:
8. the described 4-alkyl-6-aryl-5-of claim 1 (1,2, the 4-triazol-1-yl)-2-is amino-1, the application in the preparation sterilant of 3-thiazine or its salt.
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| EP2746257A1 (en) | 2012-12-21 | 2014-06-25 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds |
| EP2746258A1 (en) | 2012-12-21 | 2014-06-25 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds |
| CN111646950A (en) * | 2020-06-29 | 2020-09-11 | 江苏七洲绿色化工股份有限公司 | Preparation method of alpha-triazolyl pinacolone |
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| CN101440072B (en) * | 2008-12-24 | 2010-09-15 | 湖南大学 | 4-tertiary butyl-6-aryl-2-6H-1,3-thiazine or salt thereof, as well as preparation method and application thereof |
| CN101570521B (en) * | 2009-06-15 | 2010-08-18 | 湖南大学 | Preparation method and medical application of 4-tert-butyl-6-phenyl-2-amino-6H-1,3-thiazine salt |
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