CN102391261A - N-substituted dioxazine compound as well as preparation method and application thereof - Google Patents

N-substituted dioxazine compound as well as preparation method and application thereof Download PDF

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CN102391261A
CN102391261A CN2011103129260A CN201110312926A CN102391261A CN 102391261 A CN102391261 A CN 102391261A CN 2011103129260 A CN2011103129260 A CN 2011103129260A CN 201110312926 A CN201110312926 A CN 201110312926A CN 102391261 A CN102391261 A CN 102391261A
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chloro
oxadiazine
indeno
methoxycarbonyl
methyl ester
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徐德锋
吕龙
李绍顺
唐庆红
付群梅
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Shanghai Institute of Organic Chemistry of CAS
Shanghai Jiaotong University
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Shanghai Institute of Organic Chemistry of CAS
Shanghai Jiaotong University
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Abstract

The invention relates to an N-substituted dioxazine compound as well as a preparation method and application thereof. The N-substituted dioxazine compound has the following chemical structure general formula (I), wherein Ar in the chemical structure general formula (I) is a benzene ring, a naphthalene ring, and a pyridine or pyrimidine ring system. The compound is prepared with the following two steps: (1) taking 2-(benzyl)-7-benzindene[1,2-e][1,3-4] dioxazine-2,4a(3H,5H)-dicarboxylic acid-4a-methoxycarbonyl group and hydrogen as raw materials, taking Pd/C in solvent a as catalyst a, and carrying out hydrogenation, thus obtaining an intermediate B after reaction is finished; (2) taking (carbonylchloride) (aryl) methyl carhamate as the intermediate C, and carrying out (carbonylchloride) (aryl) methyl carhamate with the intermediate B obtained in the step (1) in the presence of a catalyst b in the solvent b; and obtaining the product N-substituted dioxazine compound. Compared with the prior art, the insecticidalactivity on the armyworm by the N-substituted dioxazine compound is 80-100%.

Description

A kind of N-substituted dioxazine compound
Technical field
The present invention relates to a kind of sterilant, especially relate to a kind of N-substituted dioxazine compound, its preparation method and application with insecticidal activity.
Background technology
Oxadiazine class (oxadiazine) sterilant indenes worm prestige (indoxacarb) is that the sodium channel of Dupont (Dupont) company exploitation in 1992 suppresses broad spectrum pesticide (W09211249); Based on a kind of new insecticidal action mechanism; Be the sodium-ion channel of block nerves cell, the possibility of cross resistance takes place in minimizing and common insecticide (like pyrethrin, organophosphorus and carbamate insecticides).Indenes worm prestige itself is a kind of precursor sterilant, through removing the methoxycarbonyl (COOCH on the amide nitrogen atom at the insect body intracellular metabolite 3) after be converted into active compound, it is good, low and to the advantage of birds, fish and beneficial insect safety, as one of desirable kind of alternative organic phosphorous insecticide to mammalian toxicity in the wide spectrum scope, to have very high insecticidal activity and merged Environmental compatibility.
The lead compound of indenes worm prestige is process for preparation of benzoylurea compounds RH3421, and Philips-Duphar company uses on the basis of process for preparation of benzoylurea compounds 1 that row such as biology is theoretical to become 2 with 1, develops ring texture 3 afterwards.A in structure 3, Z can be multiple group, and can form five yuan or six-ring with other atoms, are optimized for 4 (PH60-42) for the ease of synthesis of cyclic structure 3, possibly can not satisfy the requirement of registration owing to residual, do not have final industriallization.
Figure BDA0000098966540000011
Ricard doctor Jacobson (Rhom and Hass) began in 1980 to compound 4; Find compound 5 (RH3421) through composition optimizes; RH3421 not only has fine activity to lepidopteran, coleopteran pest, than having good control effect under the low dosage.The mechanism of action is novel, is the sodium-ion channel suppressor factor, and is different fully with the mechanism of process for preparation of benzoylurea compounds.
Figure BDA0000098966540000021
Because RH3421 has specific effect mechanism; People such as the Thomas Stevenson of E.I.Du Pont Company begin the RH3421 compounds is carried out composition optimizes; On the basis of RH3421 and compound 6, the C atom exchange with on the N atom on 1 and 3 obtains compound 7; Synthesized some compounds, the living result of survey that exsomatizes shows active preferably.
Figure BDA0000098966540000022
The derived structure 8 and 9 of compound 6 possibly be because hydrogen bond, the ThomasStevenson of E.I.Du Pont Company etc. just imagination substituting group of 4 of the pyrazoles in the compound thing 9 such as R2 and 3 phenyl ring ortho position cyclizations are promptly become structure is 10 and 11 compound.
Figure BDA0000098966540000031
Give birth to the activity of surveying discovery compound 11 through exsomatizing and be superior to 12b, also pyrazoles opened loop compound 12b is studied simultaneously, and find that B1 is CH 2Activity to be better than B1 be CH 2CH 2Compound, but the synthetic compound is all unsatisfactory aspect activity profile and residual activity, needs to improve.They find that the size of encircling directly has influence on biological activity through structure activity analysis, and compound 12a and 12b have been carried out Combinatorial Optimization is 13.Through discovering that compound 14 has good control effect to lepidoptera pest under certain metering, but the residence time is long.
Figure BDA0000098966540000032
The lot of experiment results data are analyzed,, found 15 suitable residual activities and ecological performance preferably, but Mammals is had higher relatively activity through further optimizing research.Through further having discovered the structure of indenes worm prestige, more weakly can be shown once more that for the synthetic development of active very high indenes worm prestige synthetic chemistry is an inexhaustible technology by the insect tachymetabolism although indenes worm prestige itself is active.
Figure BDA0000098966540000041
Summary of the invention
The object of the invention is exactly for the defective that overcomes above-mentioned prior art existence a kind of N-substituted dioxazine compound to be provided.
The object of the invention can be realized through following technical scheme: a kind of N-substituted dioxazine compound, it is characterized in that, the chemical structure of general formula of this compound (I) as follows:
Ar is phenyl ring, naphthalene nucleus, pyridine or pyrimidine ring system in the chemical structure of general formula (I).
Described compound comprises:
(1) (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl (pyridine) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester (SIOC-Y-001 representes with code name),
(2) (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl (naphthalene) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester (SIOC-Y-002 representes with code name),
(3) (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl [2-(4-picoline)] amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester (SIOC-Y-003 representes with code name),
(4) (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl [2-(6-picoline)] amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester (SIOC-Y-004 representes with code name),
(5) (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl [2-(5-bromopyridine)] amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester (SIOC-Y-005 representes with code name),
(6) (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl [2-(5-iodine pyridine)] amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester (SIOC-Y-006 representes with code name),
(8) (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl [4-(2-chloropyridine)] amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester (SIOC-Y-008 representes with code name),
(9) (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl [3-(2-chloropyridine)] amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester (SIOC-Y-009 representes with code name),
(10) (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl (2-methoxynaphthalene) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester (SIOC-Y-010 representes with code name),
(11) (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl (2-oxyethyl group naphthalene) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester (SIOC-Y-011 representes with code name),
(12) (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl (2-positive propoxy naphthalene) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester (SIOC-Y-012 representes with code name),
(13) (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl (2-n-pentyloxy naphthalene) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester (SIOC-Y-013 representes with code name),
(14) (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl (the positive hexyloxy naphthalene of 2-) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester (SIOC-Y-014 representes with code name),
(15) (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl (2-isopropoxy naphthalene) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester (SIOC-Y-015 representes with code name),
(16) (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl (2-n-butoxy naphthalene) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester (SIOC-Y-016 representes with code name),
(17) (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl [2-(4, the 6-dimethoxypyridin)] amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester (SIOC-Y-017 representes with code name),
(18) (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl (the special butyric ester naphthalene of 2-) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester (SIOC-Y-018 representes with code name),
(19) (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl (the disappointing basic naphthalene of 2-) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester (SIOC-Y-019 representes with code name),
(20) (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl (2-butyric ester naphthalene) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester (SIOC-Y-020 representes with code name),
(21) (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl (2-acetic ester naphthalene) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester (SIOC-Y-021 representes with code name),
(22) (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl (2-propionic ester naphthalene) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester (SIOC-Y-022 representes with code name),
(23) (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl (2-methoxy methyl ether naphthalene) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester (SIOC-Y-023 representes with code name),
(24) (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl (2-benzoic ether naphthalene) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester (SIOC-Y-024 representes with code name),
(25) (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl (2-pyrans manthanoate naphthalene) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester (SIOC-Y-025 representes with code name),
(26) (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl (2-methoxy manthanoate naphthalene) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester (SIOC-Y-026 representes with code name),
(27) (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl 2-(4-chloro-6-methoxy pyrimidine) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester (SIOC-Y-027 representes with code name),
(28) (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl 2-(4, the 6-dimethoxypyridin) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester (SIOC-Y-028 representes with code name),
(29) (S)-7-chloro-3,5 one dihydros-2-[methoxycarbonyl (4-p-methoxy-phenyl) formamyl] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester (SIOC-Y-029 representes with code name),
(30) (S)-7-chloro-3,5 one dihydros-2-[methoxycarbonyl (4-ethoxyl phenenyl) formamyl] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester (SIOC-Y-030 representes with code name),
(31) (S)-7-chloro-3,5 one dihydros-2-[methoxycarbonyl (4-positive propoxy phenyl) formamyl] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester (SIOC-Y-031 representes with code name),
(32) (S)-7-chloro-3,5 one dihydros-2-[methoxycarbonyl (the different oxygen base of 4-phenyl) formamyl] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester (SIOC-Y-032 representes with code name),
(33) (S)-7-chloro-3,5 one dihydros-2-[methoxycarbonyl (4-n-butoxy phenyl) formamyl] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester (SIOC-Y-033 representes with code name),
(34) (S)-7-chloro-3,5 one dihydros-2-[methoxycarbonyl (4-n-pentyloxy phenyl) formamyl] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester (SIOC-Y-034 representes with code name),
(35) (S)-7-chloro-3,5 one dihydros-2-[methoxycarbonyl (the positive hexyloxy phenyl of 4-) formamyl] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester (SIOC-Y-035 representes with code name),
(36) (S)-7-chloro-3,5 one dihydros-2-[methoxycarbonyl (4-Trifluoromethoxyphen-l) formamyl] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester (SIOC-Y-036 representes with code name),
(37) (S)-7-chloro-3,5 one dihydros-2-[methoxycarbonyl (4-trifluoro ethoxy phenyl) formamyl] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester (SIOC-Y-037 representes with code name),
(38) (S)-7-chloro-3,5 one dihydros-2-[methoxycarbonyl (4-trifluoromethyl) formamyl] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester (SIOC-Y-038 representes with code name),
(39) (S)-7-chloro-3,5 one dihydros-2-[methoxycarbonyl (2-Trifluoromethoxyphen-l) formamyl] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester (SIOC-Y-039 representes with code name),
(40) (S)-7-chloro-3,5 one dihydros-2-[methoxycarbonyl 2-[(3-Trifluoromethoxyphen-l) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester (SIOC-Y-040 representes with code name),
(41) (S)-7-chloro-3,5 one dihydros-2-[methoxycarbonyl (2-bromo-4-trifluoro oxygen base phenyl) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester (SIOC-Y-041 representes with code name),
(42) (S)-7-chloro-3,5 one dihydros-2-[methoxycarbonyl (4-nitrophenyl) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester (SIOC-Y-042 representes with code name),
(43) (S)-7-chloro-3,5 one dihydros-2-[methoxycarbonyl (4-acetoxyl group phenyl) formamyl] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester (SIOC-Y-043 representes with code name),
(44) (S)-7-chloro-3,5 one dihydros-2-[methoxycarbonyl (4-p-methoxy-phenyl) formamyl] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester (SIOC-Y-044 representes with code name),
(45) (S)-7-chloro-3,5 one dihydros-2-[methoxycarbonyl (4-acetylphenyl) formamyl] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester (SIOC-Y-045 representes with code name),
(46) (S)-7-chloro-3,5 one dihydros-2-[methoxycarbonyl (4-methanoyl phenyl) formamyl] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester (SIOC-Y-046 representes with code name),
(47) (S)-7-chloro-3,5 one dihydros-2-[methoxycarbonyl (4-trifluoromethylthio phenyl) formamyl] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester (SIOC-Y-047 representes with code name),
(48) (S)-7-chloro-3,5 one dihydros-2-[methoxycarbonyl (2, the 4-Dimethoxyphenyl) formamyl] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester (SIOC-Y-048 representes with code name),
(49) (S)-(+)-7-chloro-3,5-dihydro-2-[methoxycarbonyl (2, the 4-dinitrophenyl) aminocarboxyl] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-hydroxy acid methyl esters (SIOC-Y-049 representes with code name),
(50) (S)-7-chloro-3,5-dihydro-2-[methoxycarbonyl (2-trifluoromethoxy-5-chloro-phenyl) aminocarboxyl] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-hydroxy acid methyl esters (SIOC-Y-050 representes with code name),
(51) (S)-7-chloro-3,5 one dihydros-2-[methoxycarbonyl (4 one ethoxyl phenenyl) formamyl] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester (SIOC-Y-051 representes with code name),
(52) (S)-and 7-chloro-3,5 one dihydros-2-[methoxycarbonyl (4 monomethyl phenyl) formamyl] indeno [1,2-e] [1,3, synthetic (SIOC-Y-052 representes with code name) of 4-] oxadiazine-4a carboxylate methyl ester.
Of the present inventionization compound structure and fusing point are following:
Figure BDA0000098966540000081
Figure BDA0000098966540000091
Figure BDA0000098966540000111
Figure BDA0000098966540000121
Figure BDA0000098966540000122
Figure BDA0000098966540000131
Figure BDA0000098966540000141
A kind of preparation method of N-substituted dioxazine compound is characterized in that, this method may further comprise the steps:
(1) with 2-(benzyl)-7-chlorine indeno [1,2-e] [1,3; 4]] oxadiazine-2, and 4a (3H, 5H)-dicarboxylicacid-4a-methyl ester and hydrogen are raw material; In solvent a, be catalyzer a with Pd/C, carry out hydrogenation reaction, temperature of reaction is 20 ℃～120 ℃; Reaction pressure is a 1-15 normal atmosphere, obtains intermediate B after reaction finishes;
(2) be midbody C with (chloroformyl) (aryl) Urethylane, with the intermediate B that step (1) obtains, in solvent b, under the effect of catalyzer b, carry out condensation reaction, temperature of reaction is 0 ℃～100 ℃ and obtains product N substituted dioxazine compound.
The described solvent a of step (1) is one or more the mixture in methyl acetate, ETHYLE ACETATE, methyl alcohol, ethanol, acetonitrile, methylene dichloride, ethylene dichloride, trichloromethane, the toluene.
The described temperature of reaction of step (1) is 45 ℃～85 ℃, and reaction pressure is a 4-6 normal atmosphere.
The described solvent b of step (2) is one or more the mixture in methyl acetate, ethyl ester ETHYLE ACETATE, methyl alcohol, ethanol, acetonitrile, methylene dichloride, ethylene dichloride, trichloromethane, the toluene.
The described catalyzer b of step (2) is N, N-diisopropylethylamine, triethylamine, pyridine or piperidines.
The described temperature of reaction of step (2) is 20 ℃～60 ℃.
Step (2) gained N substituted dioxazine compound adopts recrystallization method to carry out separation and purification; Or adopting the isolating method of column chromatography to carry out separation and purification, the solvent that described recrystallization method adopts is one or more the mixture in methyl alcohol, ethanol, Virahol, methyl acetate, ETHYLE ACETATE, acetonitrile, methylene dichloride, ethylene dichloride, trichloromethane, toluene, the sherwood oil.
A kind of application of N-substituted dioxazine compound, this compound is used to prepare sterilant, and the insecticidal activity of mythimna separata is reached 80%～100%.
Compared with prior art, the present invention constantly carries out composition optimizes and transformation to structure (I), finally works out some new N substituted dioxazine compound Y001-Y052 with high insecticidal activity.
The present invention relates to N substituted dioxazine compound SIOC-Y-(001-052) shows the indoor biological activity test of 4 worm targets such as paddy rice brown paddy plant hopper, mythimna separata (small cabbage moth), red spider, aphis craccivora: compound S IOC-Y-(001-052) is when general sieve concentration 500mg/L; Wherein compound S IOC-Y-006,014,038,041-043,046,047,049,051 pair of mythimna separata demonstrate 100% insecticidal activity; 036,037,039 pair of mythimna separata demonstrates 80% insecticidal activity, but relatively poor or do not have an insecticidal action to other 3 kinds of indoor insecticidal activities of worm target.All the other compounds are to 4 kinds of all relatively poor or nothings of the indoor insecticidal activity of worm target.
Active compound reduces concentration and further screens, and the result shows that SIOC-Y-047 still shows insecticidal activity preferably to mythimna separata, and insecticidal activity still is 100% when concentration 20mg/L.All the other compounds reduce that concentration are active obviously to be reduced, and are indoor relatively poor or do not have an insecticidal action to the mythimna separata insecticidal activity under concentration 20mg/L.The result show compound S IOC-Y-047 to the activity of mythimna separata and prodenia litura slightly poor with indenes worm prestige, but EC 50Belong to same order of magnitude level.
Embodiment
Below in conjunction with specific embodiment the present invention is elaborated: present embodiment provided detailed embodiment and concrete operating process, but protection scope of the present invention is not limited to following embodiment being to implement under the prerequisite with technical scheme of the present invention.
Present embodiment adopts 2-(benzyl)-7-chlorine indeno [1,2-e] [1,3,4]] oxadiazine-2; 4a (3H, 5H)-dicarboxylicacid-4a-methyl ester (A) carries out hydrogenation reaction for raw material, hydrogenating reduction product 7-chloro-2,3 under Pd/C catalysis; 4a, 5-tetrahydrochysene indeno [1,2-e] [1,3; 4]] oxadiazine-4a-methyl-formiate (B) carries out reactions step such as condensation reaction again and prepares the N substituted dioxazine compound with (chloroformyl) (aryl) Urethylane midbody (C), and Bn representes benzyl in the reaction formula, and Ar representes aryl.
It below is the detailed description of the embodiment of the invention.
7-chloro-2,3,4a, 5-tetrahydrochysene indeno [1,2-e] [1,3,4]] preparation of oxadiazine-4a-methyl-formiate (B)
In three mouthfuls of reaction flasks of 50ml band gas tube, add methyl acetate (20ml), 2-(benzyl)-7-chlorine indeno [1,2-e] [1,3,4] oxadiazines-2, and 4a (3H, 5H)-dicarboxylicacid 4a-methyl ester (200mg), 10%Pd/C (30mg), hydrogen shield reacted 30 minutes down; Add the acyl chlorides (C) that makes, add N, N-diisopropylethylamine (200mg) removes hydrogen shield simultaneously, changes nitrogen protection, reacts 12-18 hour; Remove nitrogen protection, dichloromethane extraction use in washing, and anhydrous magnesium sulfate drying is concentrated, and carries out aftertreatment and get the N substituted dioxazine compound.
The preparation method of general structure of the present invention (I) compound comprises that following two reactions carry out, and reaction formula is following:
Embodiment 1
(S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl (pyridine) amino] formyl radical] indeno [1,2-e] [1,3, the preparation of 4-] oxadiazine-4a (3H)-carboxylate methyl ester (SIOC-Y-001)
In the 50ml reaction flask, add methyl acetate (20ml), 10%Pd/C (50mg) and 2-(benzyl)-7-chlorine indeno [1,2-e] [1,3,4] oxadiazines-2, and 4a (3H, 5H)-dicarboxylicacid 4a-methyl ester (A) (200mg, 0.5mmol), hydrogen shield reacted 30 minutes down; (130mg, methyl acetate solution (10ml) 0.6mmol) add N, and (200mg 1.5mmol) removes hydrogen shield to the N-diisopropylethylamine simultaneously, changes nitrogen protection, reacts 12-18 hour to add (chloroformyl) (2-pyridine) Urethylane; Remove nitrogen protection, dichloromethane extraction is used in washing, and anhydrous magnesium sulfate drying concentrates, and separates through silica gel column chromatography, gets faint yellow solid 161.1mg, productive rate 69.5%, fusing point: 150-152 ℃.
In like manner get SIOC-Y-002 to SIOC-Y-052 compound.
Embodiment 2. (S)-7-chloro-3, and 5-dihydro-2-[[methoxycarbonyl (naphthalene) amino] formyl radical] indeno [1,2-e] [1,3, the preparation of 4-] oxadiazine-4a (3H)-carboxylate methyl ester (SIOC-Y-002).
Figure BDA0000098966540000191
Fusing point: 81-83 ℃.
1H?NMR(300MHz，CDCl 3)δ：8.14(d，J＝7.5Hz，1H)，7.96-7.83(m，2H)，7.66-7.44(m，4H)，7.36-7.25(m，3H)，5.70(d，J＝9.0Hz，1H)，5.26(d，J＝9.6Hz，1H)，3.76-3.64(m，6H)，3.48(d，J＝16.5Hz，1H)，3.27(d，J＝16.8Hz，1H)。
3. (S)-7-chloro-3, and 5-dihydro-2-[[methoxycarbonyl [2-(4-picoline)] amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester (SIOC-Y-003)
Figure BDA0000098966540000192
Fusing point: 169-171 ℃.
1H?NMR(300MHz，CDCl 3)δ：8.17(d，J＝4.8Hz，1H)，7.43(s，1H)，7.38(d，J＝8.7Hz，1H)，7.30-7.22(m，2H)，6.89(d，J＝5.1Hz，1H)，5.82(d，J＝9.9Hz，1H)，5.24(d，J＝9.6Hz，1H)，3.74(s，3H)，3.70(s，3H)，3.45(d，J＝16.5Hz，1H)，3.22(d，J＝16.2Hz，1H)，2.36(s，3H)。
4. (S)-7-chloro-3, and 5-dihydro-2-[[methoxycarbonyl [2-(6-picoline)] amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester
Figure BDA0000098966540000201
Fusing point: 84-86 ℃.
1H?NMR(300MHz，CDCl 3)δ：7.59(t，J＝7.8Hz，1H)，7.42(d，J＝8.4Hz，1H)，7.35(d，J＝8.4Hz，1H)，7.31-7.21(m，2H)，6.90(d，J＝7.5Hz，1H)，5.82(d，J＝10.2Hz，1H)，5.24(d，J＝10.2Hz，1H)，3.77(s，3H)，3.71(s，3H)，3.45(d，J＝16.5Hz，1H)，3.23(d，J＝16.2Hz，1H)，2.39(s，3H)。
5. (S)-7-chloro-3, and 5-dihydro-2-[[methoxycarbonyl [2-(5-bromopyridine)] amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester
Figure BDA0000098966540000202
Fusing point: 127-129 ℃.
1H?NMR(300MHz，CDCl 3)δ：8.33(s，1H)，7.83(dd，J＝8.7，2.7Hz，1H)，7.63(d，J＝8.7Hz，1H)，7.37(d，J＝8.7Hz，1H)，7.32-7.22(m，2H)，5.84(d，J＝10.2Hz，1H)，5.26(d，J＝10.2Hz，1H)，3.78(s，3H)，3.72(s，3H)，3.47(d，J＝16.2Hz，1H)，3.25(d，J＝16.2Hz，1H)。
6. (S)-7-chloro-3, and 5-dihydro-2-[[methoxycarbonyl [2-(5-iodine pyridine)] amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester
Figure BDA0000098966540000211
Fusing point: 154-156 ℃.
1H?NMR(300MHz，CDCl 3)δ：8.47(s，1H)，7.99(dd，J＝8.4，1.8Hz，1H)，7.54(d，J＝9.0Hz，1H)，7.36(d，J＝8.7Hz，1H)，7.31-7.22(m，2H)，5.83(d，J＝9.6Hz，1H)，5.25(d，J＝10.2Hz，1H)，3.77(s，3H)，3.72(s，3H)，3.46(d，J＝16.2Hz，1H)，3.25(d，J＝16.2Hz，1H)。
8. (S)-7-chloro-3, and 5-dihydro-2-[[methoxycarbonyl [4-(2-chloropyridine)] amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester
Figure BDA0000098966540000212
Fusing point: 63-66 ℃.
1H?NMR(300MHz，CDCl 3)δ：8.38(s，1H)，7.67(dd，J＝11.4，2.1Hz，1H)，7.50(d，J＝8.1Hz，1H)，7.40-7.28(m，3H)，5.72(d，J＝9.3Hz，1H)，5.21(d，J＝9.9Hz，1H)，3.75(s，3H)，3.69(s，3H)，3.49(d，J＝16.2Hz，1H)，3.26(d，J＝16.5Hz，1H)。
9. (S)-7-chloro-3, and 5-dihydro-2-[[methoxycarbonyl [3-(2-chloropyridine)] amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester
Fusing point: 91-93 ℃.
1H?NMR(300MHz，CDCl 3)δ：8.33(dd，J＝4.5，1.8Hz，1H)，7.67(dd，J＝7.8，1.5Hz，1H)，7.49(d，J＝8.4Hz，1H)，7.37-7.27(m，3H)，5.64(d，J＝9.6Hz，1H)，5.23(d，J＝9.3Hz，1H)，3.77(s，3H)，3.71(s，3H)，3.46(d，J＝16.8Hz，1H)，3.23(d，J＝16.5Hz，1H)。
10. (S)-7-chloro-3, and 5-dihydro-2-[[methoxycarbonyl (2-methoxynaphthalene) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester
Figure BDA0000098966540000221
Fusing point: 105-107 ℃.
1H?NMR(300MHz，CDCl 3)δ：7.98-7.74(m，3H)，7.60-7.24(m，6H)，5.63(d，J＝9.3Hz，1H)，5.30(d，J＝9.3Hz，1H)，3.76-3.67(m，9H)，3.43(d，J＝10.2Hz，1H)，3.28(d，J＝9.0Hz，1H)。
11. (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl (2-oxyethyl group naphthalene) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester
Figure BDA0000098966540000222
Fusing point: 75-77 ℃.
1H?NMR(300MHz，CDCl 3)δ：7.94-7.74(m，3H)，7.59-7.23(m，6H)，5.78-5.64(m，1H)，5.33-5.15(m，1H)，4.26-4.10(m，2H)，3.76-3.63(m，6H)，3.55-3.37(m，1H)，3.33-3.14(m，1H)，1.43-1.28(m，3H)。
12. (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl (2-positive propoxy naphthalene) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester
Figure BDA0000098966540000231
Fusing point: 77-79 ℃
1H?NMR(300MHz，CDCl 3)δ：7.98-7.72(m，3H)，7.58-7.23(m，6H)，5.78-5.64(m，1H)，5.33-5.16(m，1H)，4.15-3.99(m，2H)，3.77-3.64(m，6H)，3.53-3.38(m，1H)，3.31-3.17(m，1H)，1.88-1.62(m，2H)，1.12-0.92(m，3H)。
13. (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl (2-n-pentyloxy naphthalene) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester
Figure BDA0000098966540000232
Fusing point: 55-57 ℃
1H?NMR(300MHz，CDCl 3)δ：7.96-7.74(m，3H)，7.59-7.24(m，6H)，5.78-5.64(m，1H)，5.31-5.16(m，1H)，4.19-4.02(m，2H)，3.77-3.64(m，6H)，3.53-3.39(m，1H)，3.31-3.18(m，1H)，1.90-1.62(m，2H)，1.53-1.17(m，4H)，0.99-0.78(m，3H)。
14. (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl (the positive hexyloxy naphthalene of 2-) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester
Figure BDA0000098966540000233
Fusing point: 62-64 ℃
1H?NMR(300MHz，CDCl 3)δ：7.92-7.73(m，3H)，7.57-7.20(m，6H)，5.77-5.62(m，1H)，5.30-5.15(m，1H)，4.18-4.03(m，2H)，3.76-3.63(m，6H)，3.52-3.39(m，1H)，3.32-3.18(m，1H)，1.85-1.62(m，2H)，1.51-1.12(m，6H)，0.94-0.78(m，3H)。
15. (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl (2-isopropoxy naphthalene) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester
Fusing point: 72-74 ℃
1H?NMR(300MHz，CDCl 3)δ：7.95-7.71(m，3H)，7.63-7.21(m，6H)，5.80-5.66(m，1H)，5.33-5.16(m，1H)，4.79-4.59(m，1H)，3.74-3.63(m，6H)，3.50-3.37(m，1H)，3.29-3.16(m，1H)，1.38-1.23(m，6H)。
16 (S)-7-chloro-3, and 5-dihydro-2-[[methoxycarbonyl (2-n-butoxy naphthalene) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester
Figure BDA0000098966540000242
Fusing point: 79-81 ℃.
1H?NMR(300MHz，CDCl 3)δ：7.96-7.74(m，3H)，7.59-7.23(m，6H)，5.78-5.64(m，1H)，5.33-5.14(m，1H)，4.20-4.05(m，2H)，3.77-3.64(m，6H)，3.55-3.37(m，1H)，3.34-3.15(m，1H)，1.86-1.55(m，4H)，1.05-0.88(m，3H)。
17. (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl [2-(4, the 6-dimethoxypyridin)] amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester
Figure BDA0000098966540000251
1H?NMR(300MHz，CDCl 3)δ：7.36(d，J＝9.0Hz，1H)，7.30-7.22(m，2H)，6.81(s，1H)，5.85(d，J＝9.9Hz，1H)，3.76(s，3H)，3.71(s，3H)，3.45(d，J＝16.5Hz，1H)，3.22(d，J＝15.9Hz，1H)，2.43(s，6H)。
18. (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl (the special butyric ester naphthalene of 2-) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester
Figure BDA0000098966540000252
Fusing point: 103-104 ℃
1H?NMR(300MHz，CDCl 3)δ：7.94-7.72(m，3H)，7.56-7.25(m，6H)，5.72-5.60(m，1H)，5.33-5.14(m，1H)，3.77-3.59(m，6H)，3.54-3.37(m，1H)，3.34-3.17(m，1H)，1.26-1.10(m，9H)。
19. (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl (the disappointing basic naphthalene of 2-) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester
Fusing point: 107-109 ℃
1H?NMR(300MHz，CDCl 3)δ：8.18(s，1H)，8.00(t，J＝8.1Hz，2H)，7.74(d，J＝8.1Hz，1H)7.66-7.47(m，5H)，6.52(brs，1H)，5.71(d，J＝9.6Hz，1H)，5.08(d，J＝9.9Hz，1H)，3.77(s，3H)，3.74(s，3H)，3.52(d，J＝15.9Hz，1H)，3.33(d，J＝15.6Hz，1H)。
20. (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl (2-butyric ester naphthalene) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester
Figure BDA0000098966540000261
Fusing point: 85-87 ℃
1H?NMR(300MHz，CDCl 3)δ：8.07-7.80(m，4H)，7.63-7.45(m，2H)，7.35-7.15(m，3H)，5.75-5.60(m，1H)，5.27-5.13(m，1H)，3.73-3.67(m，6H)，3.48-3.37(m，1H)，3.27-3.17(m，1H)，2.62-2.44(m，2H)，1.84-1.57(m，4H)，0.91-0.83(m，3H)。
21. (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl (2-acetic ester naphthalene) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester
Figure BDA0000098966540000262
Fusing point: 93-95 ℃
1H?NMR(300MHz，CDCl 3)δ：8.08-7.80(m，4H)，7.68-7.44(m，3H)，7.40-7.16(m，2H)，5.74-5.62(m，1H)，5.29-5.16(m，1H)，3.74-3.61(m，6H)，3.42-3.33(m，1H)，3.27-3.15(m，1H)，2.33-2.16(m，3H)。
22. (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl (2-propionic ester naphthalene) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester
Figure BDA0000098966540000271
Fusing point: 87-89 ℃
1H?NMR(300MHz，CDCl 3)δ：8.07-7.79(m，4H)，7.65-7.45(m，2H)，7.36-7.14(m，3H)，5.75-5.58(m，1H)，5.28-5.12(m，1H)，3.75-3.57(m，6H)，3.49-3.35(m，1H)，3.29-3.14(m，1H)，2.68-2.46(m，2H)，1.31-1.18(m，3H)。
23. (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl (2-methoxy methyl ether naphthalene) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester
Figure BDA0000098966540000272
Fusing point: 71-73 ℃
1H?NMR(300MHz，CDCl 3)δ：8.01-7.74(m，3H)，7.63-7.33(m，4H)，7.32-7.22(m，2H)，5.75-5.60(m，1H)，5.35-6.15(m，3H)，3.80-3.63(m，6H)，3.54-3.38(m，4H)，3.30-3.18(m，1H)。
24. (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl (2-benzoic ether naphthalene) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester
Figure BDA0000098966540000281
Fusing point: 109-111 ℃
1H?NMR(300MHz，CDCl 3)δ：8.33-7.85(m，6H)，7.69-6.81(m，8H)，5.78-5.57(m，1H)，5.23-5.08(m，3H)，3.73-3.49(m，6H)，3.47-2.81(m，2H)。
25. (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl (2-pyrans manthanoate naphthalene) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester
Figure BDA0000098966540000282
Fusing point: 80-82 ℃
1H?NMR(300MHz，CDCl 3)δ：8.11-7.85(m，4H)，7.75-7.37(m，6H)，7.31-7.16(m，2H)，5.78-5.61(m，1H)，5.26-5.16(m，1H)，3.75-3.57(m，6H)，3.54-3.03(m，2H)。
26. (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl (2-methoxy manthanoate naphthalene) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester
Figure BDA0000098966540000283
Fusing point: 97-99 ℃
1H?NMR(300MHz，CDCl 3)δ：8.10-7.80(m，4H)，7.66-7.47(m，3H)，7.45-7.30(m，2H)，5.75-5.64(m，1H)，5.26-5.18(m，1H)，3.79-3.64(m，6H)，3.53-3.40(m，1H)，3.37-3.24(m，1H)。
27. (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl 2-(4-chloro-6-methoxy pyrimidine) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester
Figure BDA0000098966540000291
Fusing point: 61-63 ℃
1H?NMR(300MHz，CDCl 3)δ：7.42-7.24(m，3H)，6.49(s，1H)，5.83(d，J＝9.9Hz，1H)，3.91(s，3H)，3.81(s，3H)，3.71(s，3H)，3.47(d，J＝16.2Hz，1H)，3.23(d，J＝16.2Hz，1H).
28. (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl 2-(4, the 6-dimethoxypyridin) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester
Figure BDA0000098966540000292
Fusing point: 58-60 ℃
1H?NMR(300MHz，CDCl 3)δ：7.40-7.22(m，3H)，5.83(d，J＝10.2Hz，1H)，5.77(s，1H)，5.22(d，J＝9.9Hz，1H)，3.85(s，6H)，3.80(s，3H)，3.69(s，3H)，3.46(d，J＝16.5Hz，1H)，3.21(d，J＝16.2Hz，1H)。
29. (S)-and 7-chloro-3,5 one dihydros-2-[methoxycarbonyl (4-p-methoxy-phenyl) formamyl] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester
Figure BDA0000098966540000301
Fusing point: 87-88 ℃
1H?NMR(300MHz，CDCl 3)δ：8.41-8.23(m，3H)，8.09(d，J＝9.6Hz，1H)，7.66-7.39(m，5H)，7.37-7.28(m，2H)，5.68(t，J＝11.1Hz，1H)，5.24(t，J＝11.4Hz，1H)，3.99(s，3H)，3.70(s，6H)，3.47(d，J＝16.5Hz，1H)，3.25(d，J＝16.5Hz，1H)。
30. (S)-and 7-chloro-3,5 one dihydros-2-[methoxycarbonyl (4-ethoxyl phenenyl) formamyl] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester
Fusing point: 75-77 ℃
1H?NMR(300MHz，CDCl 3)δ：8.39-8.27(m，1H)，8.08(d，J＝7.8Hz，1H)，7.64-7.27(m，6H)，6.82-6.71(m，1H)，5.68(t，J＝10.5Hz，1H)，5.24(t，J＝10.5Hz，1H)，4.27-4.13(m，2H)，3.72-3.64(s，6H)，3.47-3.36(m，1H)，3.32-3.18(m，1H)，1.58-1.46(m，3H)。
31. (S)-and 7-chloro-3,5 one dihydros-2-[methoxycarbonyl (4-positive propoxy phenyl) formamyl] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester
Figure BDA0000098966540000311
Fusing point: 57-59 ℃
1H?NMR(300MHz，CDCl 3)δ：8.40-8.27(m，1H)，8.07(d，J＝8.1Hz，1H)，7.63-7.21(m，6H)，6.82-6.71(m，1H)，5.67(t，J＝12.3Hz，1H)，5.23(t，J＝9.9Hz，1H)，4.16-4.00(m，2H)，3.73-3.63(m，6H)，3.36-3.26(m，1H)，3.18-3.07(m，1H)，1.18-0.96(m，5H)。
32. (S)-and 7-chloro-3,5 one dihydros-2-[methoxycarbonyl (the different oxygen base of 4-phenyl) formamyl] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester
Figure BDA0000098966540000312
Fusing point: 74-76 ℃
1H?NMR(300MHz，CDCl 3)δ：8.41-8.27(m，1H)，8.09(d，J＝7.8Hz，1H)，7.65-7.41(m，4H)，7.38-7.30(m，2H)，6.80(d，J＝7.8Hz，1H)，5.72(t，J＝10.2Hz，1H)，5.27(t，J＝10.2Hz，1H)，4.83-4.68(m，1H)，3.75-3.67(s，6H)，3.49(d，J＝16.2Hz，1H)，3.28(d，J＝16.2Hz，1H)，1.46(s，6H)。
33. (S)-and 7-chloro-3,5 one dihydros-2-[methoxycarbonyl (4-n-butoxy phenyl) formamyl] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester
Fusing point: 67-69 ℃
1H?NMR(300MHz，CDCl 3)δ：8.42-8.27(m，1H)，8.09(d，J＝8.7Hz，1H)，7.65-7.26(m，6H)，6.83-6.73(m，1H)，5.69(t，J＝10.2Hz，1H)，5.25(t，J＝10.2Hz，1H)，4.22-4.08(m，2H)，3.75-3.67(s，6H)，3.49(d，J＝16.2Hz，1H)，3.27(d，J＝16.2Hz，1H)，2.00-1.84(m，2H)，1.70-1.53(m，2H)，1.09-0.98(m，3H)。
34. (S)-and 7-chloro-3,5 one dihydros-2-[methoxycarbonyl (4-n-pentyloxy phenyl) formamyl] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester
Figure BDA0000098966540000322
Fusing point: 95-97 ℃
1H?NMR(300MHz，CDCl 3)δ：8.40-8.28(m，1H)，8.09(d，J＝7.5Hz，1H)，7.66-7.29(m，6H)，6.84-6.73(m，1H)，5.70(t，J＝9.0Hz，1H)，5.25(t，J＝9.0Hz，1H)，4.14(t，J＝6.0Hz，2H)，3.71(s，6H)，3.49(d，J＝16.2Hz，1H)，3.27(d，J＝16.2Hz，1H)，1.99-1.87(m，2H)，1.62-1.36(m，4H)，0.98(t，J＝6.9Hz，3H)。
35. (S)-and 7-chloro-3,5 one dihydros-2-[methoxycarbonyl (the positive hexyloxy phenyl of 4-) formamyl] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester
Figure BDA0000098966540000331
Fusing point: 91-93 ℃
1H?NMR(300MHz，CDCl 3)δ：8.42-8.28(m，1H)，8.09(d，J＝9.0Hz，1H)，7.64-7.26(m，6H)，6.85-6.73(m，1H)，5.69(t，J＝11.4Hz，1H)，5.26(t，J＝11.4Hz，1H)，4.22-4.09(m，2H)，3.75-3.67(s，6H)，3.49(d，J＝16.5Hz，1H)，3.27(d，J＝16.5Hz，1H)，2.01-1.86(m，2H)，1.66-1.49(m，2H)，1.47-1.34(m，4H)，0.99-0.81(m，3H)。
36. (S)-and 7-chloro-3,5 one dihydros-2-[methoxycarbonyl (4-Trifluoromethoxyphen-l) formamyl] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester
Figure BDA0000098966540000332
1H?NMR(300MHz，CDCl 3)δ：8.27-8.14(m，2H)，7.71-7.28(m，7H)，5.69(d，J＝9.6Hz，1H)，5.26(d，J＝9.6Hz，1H)3.73(s，6H)，3.50(d，J＝16.5Hz，1H)，3.28(d，J＝16.5Hz，1H)。
37. (S)-and 7-chloro-3,5 one dihydros-2-[methoxycarbonyl (4-trifluoro ethoxy phenyl) formamyl] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester
Fusing point: 65-67 ℃
1H?NMR(300MHz，CDCl 3)δ：8.41-8.26(m，1H)，8.14(d，J＝8.1Hz，1H)，7.71-7.25(m，6H)，6.79(d，J＝8.1Hz，1H)，5.80-5.64(m，1H)，5.36-5.18(m，1H)，5.54(q，J＝7.8Hz，2H)，5.51(d，J＝16.2Hz，1H)，5.29(d，J＝16.2Hz，1H)，3.73(s，6H)。
38. (S)-and 7-chloro-3,5 one dihydros-2-[methoxycarbonyl (4-trifluoromethyl) formamyl] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester
Figure BDA0000098966540000342
Fusing point: 96-98 ℃
1H?NMR(300MHz，CDCl 3)δ：8.33-8.20(m，2H)，7.90(d，J＝7.8Hz，1H)，7.76-7.63(m，2H)，7.58(d，J＝7.8Hz，1H)，7.38-7.29(m，3H)，5.71(d，J＝8.4Hz，1H)，5.28(d，J＝8.4Hz，1H)，3.74(s，6H)，3.50(d，J＝16.8Hz，1H)，3.28(d，J＝16.8Hz，1H)。
39. (S)-and 7-chloro-3,5 one dihydros-2-[methoxycarbonyl (2-Trifluoromethoxyphen-l) formamyl] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester
Figure BDA0000098966540000351
1H?NMR(300MHz，CDCl 3)δ：8.22(d，J＝9.0Hz，1H)，7.97-7.81(m，2H)，7.73(s，1H)，7.62-7.26(m，5H)，5.71(d，J＝9.0Hz，1H)，5.27(d，J＝9.0Hz，1H)，3.75(s，6H)，3.50(d，J＝16.5Hz，1H)，3.27(d，J＝16.5Hz，1H).
Fusing point: 91-93 ℃
40. (S)-and 7-chloro-3,5 one dihydros-2-[methoxycarbonyl 2-[(3-Trifluoromethoxyphen-l) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester
Figure BDA0000098966540000352
Fusing point: 91-93 ℃
1H?NMR(300MHz，CDCl 3)δ：8.13(s，1H)，8.02-7.86(m，2H)，7.67(d，J＝7.5Hz，1H)，7.56(d，J＝7.5Hz，1H)，7.53-7.30(m，5H)，5.83-5.60(m，1H)，5.40-5.15(m，5H)，3.71(s，6H)，3.52(d，J＝16.2Hz，1H)，3.39-3.20(m，1H).
41. (S)-7-chloro-3,5 one dihydros-2-[methoxycarbonyl (2-bromo-4-trifluoro oxygen base phenyl) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester
Figure BDA0000098966540000361
Fusing point: 55-57 ℃
1H?NMR(300MHz，CDCl 3)δ：7.64-7.49(m，2H)，7.43-7.29(m，3H)，7.20(d，J＝7.8Hz，1H)，5.66(d，J＝9.0Hz，1H)，5.24(d，J＝9.9Hz，1H)，3.76(s，3H)，3.73(s，3H)，3.49(d，J＝16.8Hz，1H)，3.26(d，J＝16.5Hz，1H)。
42. (S)-7-chloro-3,5 one dihydros-2-[methoxycarbonyl (4-nitrophenyl) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester
Figure BDA0000098966540000362
Fusing point: 69-71 ℃
1H?NMR(300MHz，CDCl 3)δ：8.25(d，J＝7.8Hz，2H)，7.53-7.45(m，3H)，7.38-7.31(m，2H)，5.77(d，J＝10.2Hz，1H)，5.25(d，J＝9.6Hz，1H)，3.78(s，3H)，3.74(s，3H)，3.52(d，J＝15.9Hz，1H)，3.28(d，J＝16.5Hz，1H)。
43. (S)-7-chloro-3,5 one dihydros-2-[methoxycarbonyl (4-acetoxyl group phenyl) formamyl] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester
Figure BDA0000098966540000371
Fusing point: 49-51 ℃
1H?NMR(300MHz，CDCl 3)δ：8.10-7.98(m，2H)，7.46(d，J＝8.4Hz，1H)，7.40-7.24(m，4H)，5.70(d，J＝9.6Hz，1H)，5.21(d，J＝9.9Hz，1H)，4.40-4.26(m，2H)，3.79-3.60(m，6H)，3.45(d，J＝15.9Hz，1H)，3.21(d，J＝16.2Hz，1H)，1.41-1.27(m，3H)。
44. (S)-and 7-chloro-3,5 one dihydros-2-[methoxycarbonyl (4-p-methoxy-phenyl) formamyl] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester
Figure BDA0000098966540000372
Fusing point: 49-51 ℃
1H?NMR(300MHz，CDCl 3)δ：7.98(d，J＝8.4Hz，2H)，7.50(d，J＝8.1Hz，1H)，7.42(d，J＝8.7Hz，2H)，7.33(d，J＝8.1Hz，2H)，5.75(d，J＝10.2Hz，1H)，5.24(d，J＝9.9Hz，1H)，3.76(s，3H)，3.73(s，3H)，3.50(d，J＝16.2Hz，1H)，3.27(d，J＝16.2Hz，1H)。
45. (S)-and 7-chloro-3,5 one dihydros-2-[methoxycarbonyl (4-acetylphenyl) formamyl] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester
Figure BDA0000098966540000381
Fusing point: 64-66 ℃
1H?NMR(300MHz，CDCl 3)δ：8.03(d，J＝8.7Hz，2H)，7.48(d，J＝8.1Hz，1H)，7.43-7.28(m，4H)，5.73(d，J＝9.9Hz，1H)，5.22(d，J＝9.9Hz，1H)，3.90(s，3H)，3.75(s，3H)，3.70(s，3H)，3.58(d，J＝16.8Hz，1H)，3.25(d，J＝16.8Hz，1H)。
46. (S)-and 7-chloro-3,5 one dihydros-2-[methoxycarbonyl (4-methanoyl phenyl) formamyl] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester
Figure BDA0000098966540000382
Fusing point: 69-71 ℃
1H?NMR(300MHz，CDCl 3)δ：8.03(d，J＝8.7Hz，2H)，7.48(d，J＝8.1Hz，1H)，7.43-7.28(m，4H)，5.73(d，J＝9.9Hz，1H)，5.22(d，J＝9.9Hz，1H)，3.90(s，3H)，3.75(s，3H)，3.70(s，3H)，3.58(d，J＝16.8Hz，1H)，3.25(d，J＝16.8Hz，1H)。
47. (S)-and 7-chloro-3,5 one dihydros-2-[methoxycarbonyl (4-trifluoromethylthio phenyl) formamyl] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester
Figure BDA0000098966540000391
Fusing point: 36-38 ℃
1H?NMR(300MHz，CDCl 3)δ：7.65(d，J＝8.4Hz，2H)，7.48(d，J＝8.4Hz，1H)，7.42-7.29(m，4H)，5.74(d，J＝9.6Hz，1H)，5.22(d，J＝9.6Hz，1H)，3.74(s，3H)，3.71(s，3H)，3.49(d，J＝16.5Hz，1H)，3.26(d，J＝16.5Hz，1H)。
48. (S)-and 7-chloro-3,5 one dihydros-2-[methoxycarbonyl (2, the 4-Dimethoxyphenyl) formamyl] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester
Figure BDA0000098966540000392
Fusing point: 78-80 ℃
1H?NMR(300MHz，CDCl 3)δ：7.50(d，J＝8.1Hz，1H)，7.34-7.25(m，2H)，6.92-6.76(m，3H)，5.68(d，J＝9.6Hz，1H)，5.21(d，J＝9.6Hz，1H)，3.78(s，3H)，3.73(s，3H)，3.71(s，6H)，3.47(d，J＝16.5Hz，1H)，3.25(d，J＝16.5Hz，1H)。
49. (S)-(+)-7-chloro-3,5-dihydro-2-[methoxycarbonyl (2, the 4-dinitrophenyl) aminocarboxyl] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-hydroxy acid methyl esters
Figure BDA0000098966540000401
Fusing point: 77-79 ℃
1H?NMR(300MHz，CDCl 3)δ：8.47(d，J＝8.1Hz，1H)，7.61(d，J＝8.4Hz，1H)，7.44(d，J＝8.17Hz，1H)，7.39-7.30(m，3H)，5.66(d，J＝9.6Hz，1H)，5.25(d，J＝9.6Hz，1H)，3.78(s，3H)，3.74(s，3H)，3.49(d，J＝16.5Hz，1H)，3.26(d，J＝17.1Hz，1H)。
50. (S)-7-chloro-3,5-dihydro-2-[methoxycarbonyl (2-trifluoromethoxy-5-chloro-phenyl) aminocarboxyl] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-hydroxy acid methyl esters
Figure BDA0000098966540000402
Fusing point: 46-48 ℃
1H?NMR(300MHz，CDCl 3)δ：7.50(d，J＝8.7Hz，1H)，7.44(d，J＝2.1Hz，1H)，7.41-7.31(m，3H)，7.30-7-26(m，1H)，5.69(d，J＝9.6Hz，1H)，5.24(d，J＝9.3Hz，1H)，3.74(s，63H)，3.51(d，J＝16.8Hz，1H)，3.29(d，J＝16.8Hz，1H)。
Fusing point: 47-49 ℃.
51. (S)-and 7-chloro-3,5 one dihydros-2-[methoxycarbonyl (4 one ethoxyl phenenyl) formamyl] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester
Figure BDA0000098966540000411
1H?NMR(300MHz，CDCl 3)δ：7.56(d，J＝8.4Hz，1H)，7.35-7.24(m，4H)，6.89(s，1H)，6.86(s，1H)，5.69(d，J＝9.6Hz，1H)，5.19(d，J＝10.2Hz，1H)，4.04-3.97(m，2H)，3.71(s，6H)，3.48(d，J＝16.2Hz，1H)，3.26(d，J＝16.5Hz，1H)，1.41-1.37(m，3H)
Fusing point: 137-139 ℃.
52. (S)-and 7-chloro-3,5 one dihydros-2-[methoxycarbonyl (4 monomethyl phenyl) formamyl] indeno [1,2-e] [1,3,4-] oxadiazine-4a carboxylate methyl ester synthetic
Figure BDA0000098966540000412
Fusing point: 151-153 ℃
1H?NMR(300MHz，CDCl 3)δ：7.56(d，J＝8.1Hz，1H)，7.35(d，J＝8.1Hz，1H)，7.32(s，1H)，7.28-7.17(m，4H)，5.71(d，J＝9.9Hz，1H)，5.22(d，J＝9.9Hz，1H)，3.72(s，3H)，3.72(s，3H)，3.50(d，J＝16.8Hz，1H)，3.27(d，J＝16.5Hz，1H)，2.35(s，3H)。
The indoor biological activity determination of sterilant
1 materials and methods
1.1 test medicine
The former medicine of SIOC-Y-(001-052);
98% DDVP oil (Zhangjagang City Sunyu chemical plant), the former medicine of 95% pyridaben (the Anhui safe pesticide chemical of gold ltd), the former medicine of 95% carbosulfan (Zhejiang Hetian Chemical Co., Ltd.).The 86.5% former medicine of indenes worm prestige (Zhejiang Hetian Chemical Co., Ltd.)
1.2 test target
Nilaparvata lugen (brown planthopper) (Nilaparvata legen), mythimna separata (Mythima separata), small cabbage moth (Plutella xylostella), red spider (Tetranychus cinnabarnus), aphis craccivora (Aphis medicagini).Above worm kind is that indoor for many generations to raise throughout the year or gather from the field indoor feeding many for the worm kind.
1.3 plant and instrument
Electronic analytical balance, petridish, liquid-transfering gun, Potter spray tower, writing brush etc.
1.4 chemicals treatment
Take by weighing the former medicine of certain mass with analytical balance (0.0001g), add the solvent (DMF) that contains 0.1% tween-80, be mixed with 1% preparation.Take by weighing the preparation of certain mass, adding distil water (acetone is used in the topical application dilution) dilution is mixed with the soup of measuring desired concn.
Estimate SOP (sterilant volume) according to the initiative pesticide bioactivity, general sieve concentration is selected 500mg/L.
1.5 TP
1.5.1 paddy rice brown paddy plant hopper screening---the quantitative spray method of petridish seedling worm
The paddy rice seedling is fixed in the petridish with white quartz sand, connects and use CO 2Anaesthetize 3 mid-term in age nymph, place under the POTTER spray tower spraying.The spraying back covers with the transparent plastics cup, is put in the observation ward behind the mark.Check result behind the 72h.With SD-1750 and blank CK is contrast.
1.5.2 mythimna separata screening---soak the seedling feeding method
Leaf of Semen Maydis is fully soaked into the back dry in the shade naturally in soup, put into petridish, connect 3 mid-term in age larva, add a cover mark and be placed in the observation ward.Check result behind the 72h.With SD-1750 and blank CK is contrast.
1.5.3 small cabbage moth screening---pickling process
The wild cabbage sheet is cut, punched into disk, be dipped in 20s in the soup then, be put in the Φ 9cm plastic culture dish (5/ware), connect 15/ware of small cabbage moth 2 instar larvaes, put a filter paper, add a cover.Place 26 ℃ of indoor cultivation, check result behind the 72h.Test repetition 4 times.Touch polypide with the tip tweezers, reactionlessly be regarded as dead worm.With SD-1750 and blank CK is contrast.
1.5.4 carmine spider mite screening---pickling process
The broad bean blade is broken into the leaf dish, and the back side is placed on the fritter cotton up, places in the plastic culture dish, adds less water, connects carmine spider mite and becomes mite.Treat into mite after stablizing on the blade, blade is fully inhaled defoliation sheet surface water droplet with thieving paper rapidly behind the infiltration 5s in soup, place again on the cotton, air-dry.Check result behind the 72h.With pyridaben and blank CK is contrast.
1.5.5 aphis craccivora screening---pickling process
If the broad bean blade is cut off two ends, and the back side is placed on the fritter cotton up, places in the plastic culture dish, adds less water, connects aphis craccivora and becomes aphid to produce aphid.Remove into aphid behind the 24h, continue behind the cultivation 2d blade behind the abundant 5s of infiltration, to be placed on the cotton natural airing again in soup.Check result behind the 24h.With carbosulfan and blank CK is contrast.
1.6 test statistics with advance the sieve standard
Add up the dead borer population and the borer population of living of each processing, the calculating mortality ratio (Abbott ' the s formula).
2 results and analysis
Compound S IOC-Y-(001-052) shows the indoor bioactivity screening result of 4 worm targets such as paddy rice brown paddy plant hopper, mythimna separata (small cabbage moth), red spider, aphis craccivora: compound S IOC-Y-(001-040) is when general sieve concentration 500mg/L; SIOC-Y-006,014,038,039,041,042,043,046,047,049 pair of mythimna separata demonstrate 100% insecticidal activity, and 036 pair of mythimna separata demonstrates 80% insecticidal activity.When further screening, 0047 pair of mythimna separata still shows insecticidal activity preferably, and insecticidal activity still is 100% when concentration 100mg/L and 20mg/L.Therefore, suggestion SIOC-Y-006,014,036,038,039,041,042,043,046,047,049 carries out next step screening verification; Other compound does not all have obvious activity to 4 worm targets such as paddy rice brown paddy plant hopper, mythimna separata, carmine spider mite, aphis craccivoras.(shaker test result sees attached list 1)
Subordinate list 1: compound insecticidal activity The selection result (mortality ratio, %)
Figure BDA0000098966540000441
Figure BDA0000098966540000451

Claims (10)

1. a N-substituted dioxazine compound is characterized in that, the chemical structure of general formula of this compound (I) as follows:
Figure FDA0000098966530000011
Ar is phenyl ring, naphthalene nucleus, pyridine or pyrimidine ring system in the chemical structure of general formula (I).
2. a kind of N-substituted dioxazine compound according to claim 1 is characterized in that described compound comprises:
(1) (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl (pyridine) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester,
(2) (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl (naphthalene) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester,
(3) (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl [2-(4-picoline)] amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester,
(4) (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl [2-(6-picoline)] amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester,
(5) (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl [2-(5-bromopyridine)] amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester,
(6) (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl [2-(5-iodine pyridine)] amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester,
(8) (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl [4-(2-chloropyridine)] amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester,
(9) (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl [3-(2-chloropyridine)] amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester,
(10) (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl (2-methoxynaphthalene) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester,
(11) (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl (2-oxyethyl group naphthalene) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester,
(12) (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl (2-positive propoxy naphthalene) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester,
(13) (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl (2-n-pentyloxy naphthalene) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester,
(14) (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl (the positive hexyloxy naphthalene of 2-) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester,
(15) (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl (2-isopropoxy naphthalene) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester,
(16) (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl (2-n-butoxy naphthalene) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester,
(17) (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl [2-(4, the 6-dimethoxypyridin)] amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester,
(18) (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl (the special butyric ester naphthalene of 2-) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester,
(19) (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl (the disappointing basic naphthalene of 2-) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester,
(20) (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl (2-butyric ester naphthalene) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester,
(21) (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl (2-acetic ester naphthalene) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester,
(22) (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl (2-propionic ester naphthalene) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester,
(23) (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl (2-methoxy methyl ether naphthalene) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester,
(24) (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl (2-benzoic ether naphthalene) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester,
(25) (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl (2-pyrans manthanoate naphthalene) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester,
(26) (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl (2-methoxy manthanoate naphthalene) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester,
(27) (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl 2-(4-chloro-6-methoxy pyrimidine) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester,
(28) (S)-7-chloro-3,5-dihydro-2-[[methoxycarbonyl 2-(4, the 6-dimethoxypyridin) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-carboxylate methyl ester,
(29) (S)-7-chloro-3,5 one dihydros-2-[methoxycarbonyl (4-p-methoxy-phenyl) formamyl] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester,
(30) (S)-7-chloro-3,5 one dihydros-2-[methoxycarbonyl (4-ethoxyl phenenyl) formamyl] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester,
(31) (S)-7-chloro-3,5 one dihydros-2-[methoxycarbonyl (4-positive propoxy phenyl) formamyl] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester,
(32) (S)-7-chloro-3,5 one dihydros-2-[methoxycarbonyl (the different oxygen base of 4-phenyl) formamyl] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester,
(33) (S)-7-chloro-3,5 one dihydros-2-[methoxycarbonyl (4-n-butoxy phenyl) formamyl] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester,
(34) (S)-7-chloro-3,5 one dihydros-2-[methoxycarbonyl (4-n-pentyloxy phenyl) formamyl] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester,
(35) (S)-7-chloro-3,5 one dihydros-2-[methoxycarbonyl (the positive hexyloxy phenyl of 4-) formamyl] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester,
(36) (S)-7-chloro-3,5 one dihydros-2-[methoxycarbonyl (4-Trifluoromethoxyphen-l) formamyl] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester,
(37) (S)-7-chloro-3,5 one dihydros-2-[methoxycarbonyl (4-trifluoro ethoxy phenyl) formamyl] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester,
(38) (S)-7-chloro-3,5 one dihydros-2-[methoxycarbonyl (4-trifluoromethyl) formamyl] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester,
(39) (S)-7-chloro-3,5 one dihydros-2-[methoxycarbonyl (2-Trifluoromethoxyphen-l) formamyl] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester,
(40) (S)-7-chloro-3,5 one dihydros-2-[methoxycarbonyl 2-[(3-Trifluoromethoxyphen-l) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester,
(41) (S)-7-chloro-3,5 one dihydros-2-[methoxycarbonyl (2-bromo-4-trifluoro oxygen base phenyl) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester,
(42) (S)-7-chloro-3,5 one dihydros-2-[methoxycarbonyl (4-nitrophenyl) amino] formyl radical] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester,
(43) (S)-7-chloro-3,5 one dihydros-2-[methoxycarbonyl (4-acetoxyl group phenyl) formamyl] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester,
(44) (S)-7-chloro-3,5 one dihydros-2-[methoxycarbonyl (4-p-methoxy-phenyl) formamyl] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester,
(45) (S)-7-chloro-3,5 one dihydros-2-[methoxycarbonyl (4-acetylphenyl) formamyl] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester,
(46) (S)-7-chloro-3,5 one dihydros-2-[methoxycarbonyl (4-methanoyl phenyl) formamyl] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester,
(47) (S)-7-chloro-3,5 one dihydros-2-[methoxycarbonyl (4-trifluoromethylthio phenyl) formamyl] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester,
(48) (S)-7-chloro-3,5 one dihydros-2-[methoxycarbonyl (2, the 4-Dimethoxyphenyl) formamyl] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester,
(49) (S)-(+)-7-chloro-3,5-dihydro-2-[methoxycarbonyl (2, the 4-dinitrophenyl) aminocarboxyl] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-hydroxy acid methyl esters,
(50) (S)-7-chloro-3,5-dihydro-2-[methoxycarbonyl (2-trifluoromethoxy-5-chloro-phenyl) aminocarboxyl] indeno [1,2-e] [1,3,4-] oxadiazine-4a (3H)-hydroxy acid methyl esters,
(51) (S)-7-chloro-3,5 one dihydros-2-[methoxycarbonyl (4 one ethoxyl phenenyl) formamyl] indeno [1,2-e] [1,3,4-] oxadiazine-4a-carboxylate methyl ester,
(52) (S)-and 7-chloro-3,5 one dihydros-2-[methoxycarbonyl (4 monomethyl phenyl) formamyl] indeno [1,2-e] [1,3,4-] oxadiazine-4a carboxylate methyl ester synthetic.
3. the preparation method of a claim 1 or 2 described a kind of N-substituted dioxazine compounds is characterized in that this method may further comprise the steps:
(1) with 2-(benzyl)-7-chlorine indeno [1,2-e] [1,3; 4]] oxadiazine-2, and 4a (3H, 5H)-dicarboxylicacid-4a-methyl ester and hydrogen are raw material; In solvent a, be catalyzer a with Pd/C, carry out hydrogenation reaction, temperature of reaction is 20 ℃～120 ℃; Reaction pressure is a 1-15 normal atmosphere, obtains intermediate B after reaction finishes;
(2) be midbody C with (chloroformyl) (aryl) Urethylane, with the intermediate B that step (1) obtains, in solvent b, under the effect of catalyzer b, carry out condensation reaction, temperature of reaction is 0 ℃～100 ℃ and obtains product N substituted dioxazine compound.
4. the preparation method of a kind of N-substituted dioxazine compound according to claim 3; It is characterized in that the described solvent a of step (1) is one or more the mixture in methyl acetate, ETHYLE ACETATE, methyl alcohol, ethanol, acetonitrile, methylene dichloride, ethylene dichloride, trichloromethane, the toluene.
5. the preparation method of a kind of N-substituted dioxazine compound according to claim 3 is characterized in that, the described temperature of reaction of step (1) is 45 ℃～85 ℃, and reaction pressure is a 4-6 normal atmosphere.
6. the preparation method of a kind of N-substituted dioxazine compound according to claim 3; It is characterized in that the described solvent b of step (2) is one or more the mixture in methyl acetate, ethyl ester ETHYLE ACETATE, methyl alcohol, ethanol, acetonitrile, methylene dichloride, ethylene dichloride, trichloromethane, the toluene.
7. the preparation method of a kind of N-substituted dioxazine compound according to claim 3 is characterized in that, the described catalyzer b of step (2) is N, N-diisopropylethylamine, triethylamine, pyridine or piperidines.
8. the preparation method of a kind of N-substituted dioxazine compound according to claim 3 is characterized in that, the described temperature of reaction of step (2) is 20 ℃～60 ℃.
9. the preparation method of a kind of N-substituted dioxazine compound according to claim 3; It is characterized in that; Step (2) gained N substituted dioxazine compound adopts recrystallization method to carry out separation and purification; Or adopting the isolating method of column chromatography to carry out separation and purification, the solvent that described recrystallization method adopts is one or more the mixture in methyl alcohol, ethanol, Virahol, methyl acetate, ETHYLE ACETATE, acetonitrile, methylene dichloride, ethylene dichloride, trichloromethane, toluene, the sherwood oil.
10. the application of a claim 1 or 2 described a kind of N-substituted dioxazine compounds is characterized in that this compound is used to prepare sterilant, and the insecticidal activity of mythimna separata is reached 80%～100%.
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