CN1569855A - Sulfonamide compounds and their production method and use - Google Patents

Sulfonamide compounds and their production method and use Download PDF

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CN1569855A
CN1569855A CN 200410019223 CN200410019223A CN1569855A CN 1569855 A CN1569855 A CN 1569855A CN 200410019223 CN200410019223 CN 200410019223 CN 200410019223 A CN200410019223 A CN 200410019223A CN 1569855 A CN1569855 A CN 1569855A
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methyl
dihydro
pyrimidone
pyrimidin
sulphonyl
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CN1300142C (en
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席真
程晓峰
张弘
崔东亮
牛聪伟
陈文彬
刘婧
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Nankai University
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Nankai University
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Abstract

The invention provides sulfonamide compounds and their production method and use thereof, which are are compounds having a structural formula I, II and their non-toxic salts, wherein ring A is a benzene ring or benzene ring with more than one substituent groups, X is oxygen atom or sulfur atom, the substituent groups that the ring A has include halogen, nitro, cyano, hydroxy, sulfo, ester, carboxyl, alkyl or alkyl with more than one substituent groups, alkoxy, aryl, aryloxy, amido, acylorxy, heterocyclic radical.

Description

Sulfamide compound and its production and use
One, technical field
The present invention relates to sulfamide compound, relate in particular to a kind of sulfamide compound and its production and use.
Two, background technology
Acetylactis (alcohol acid) synthetic enzyme (Acetolactate synthase) [ALS] or (Acetohydroxyacid synthase) [AHAS] are the weedicides of a few class different structures, as sulfonylurea (Sulfonylureas, SU), imidazolone type (Imidazolinone, IM), triazolo pyrimidine (Triazolopyrimidine, TP), the action target of pyrimidine Whitfield's ointment (Pyrimidyl oxylenzoate) etc.It is first the critical enzyme in the branched-chain amino acid biosynthetic pathway, and catalysis biological synthesizes first reaction of branched-chain amino acid (Xie Ansuan, leucine, Isoleucine).Branched-chain amino acid is an indispensable material in the plant materials, is plant materials internal protein synthetic integral part.The biosynthesizing of branched-chain amino acid is obstructed, and will cause stopping of protein synthesis, makes the synthetic destroyed of DNA and the requisite material of other mitotic division, causes the growth of roots of plants, stem, leaf to be suppressed, thereby plant-growth is badly damaged until death.Weedicide is just by inhibition ALS enzyme, thereby the blocking-up branched-chain amino acid is brought into play its weeding activity.
In recent years, sulphonyl class weedicide makes the development of weedicide enter the epoch of ultra-high efficiency with its ultra-high efficiency, wide spectrum, low toxicity and highly selective and low consumption, has caused people's very big concern, countries in the world are dropped into a large amount of manpower and materials in succession, have synthesized a large amount of all kinds of sulphonyl analog derivatives.At present external existing chlorine sulphur is grand, a sulphonyl class weedicide kind commercialization surplus the sulfometuron-methyl etc. ten.Therefore to have the new herbicides of self-intellecture property be an extremely urgent problem in the current pesticide research of China in exploitation.
Three, summary of the invention
Main purpose of the present invention provides a kind of sulfamide compound and its production and use, and this sulfamide compound can be applicable to prepare the preparation that prevents weed growth of ultra-high efficiency, wide spectrum, low toxicity and highly selective and low consumption.
The present invention solves the technical scheme that its technical problem takes:
Novel sulfonamide compounds of the present invention is characterized in that: be following structural formula (I) or compound (II) and non-toxic salt thereof:
Figure A20041001922300051
In the formula: ring A is phenyl ring or has substituent phenyl ring more than that X can be Sauerstoffatom or sulphur atom.
Aforesaid sulfamide compound wherein encircles the substituting group that A has and comprises: halogen atom, nitro, cyano group, hydroxyl, sulfonic group, ester group, carboxyl, alkyl or have substituent alkyl, alkoxyl group, aryl, aryloxy, acyl group, acyloxy, heterocyclic radical more than one.
Aforesaid sulfamide compound, wherein, halogen atom comprises fluorine, chlorine, bromine, iodine; Alkyl is C 1-8Alkyl, for example: methyl, ethyl, propyl group, sec.-propyl, butyl, isobutyl-, sec-butyl, the tertiary butyl, amyl group, hexyl, heptyl, octyl group etc.; Substituting group in the alkyl comprises: halogen atom, hydroxyl, C 1-6Alkoxyl group, halogen atom can be 1 to 3, C 1-6Alkoxyl group can be methoxyl group, oxyethyl group, propoxy-, isopropoxy, butoxy, isobutoxy, pentyloxy etc.; Aryl is C 6-14Aryl, for example phenyl, 1-naphthyl, 2-naphthyl, xenyl, 2-anthryl etc.; Aryloxy comprises C 6-14Aryloxy, for example phenoxy group, 1-naphthyloxy, 2-naphthyloxy etc.; Acyl group comprises formyl radical, ethanoyl, propionyl, formamyl etc.; Acyloxy comprises acetoxyl group, propionyloxy, methoxycarbonyl oxygen base, ethoxy carbonyl oxygen base, propoxycarbonyl oxygen base, butoxy carbonyl oxygen base, carbamoyloxy etc.; Heterocyclic radical can be a 5-10 unit heterocyclic radical, preferred 5-or 6-unit heterocyclic radical, it contains one or more heteroatomss (for example 1-3) except carbon atom, heteroatoms is selected from nitrogen-atoms, sulphur atom and Sauerstoffatom, for example (2-or 3-thienyl, 2-, 3-or 4-pyridyl, 2-or 3-furyl, 1-, 2-or 3-pyrryl, 2-, 3-, 4-, 5-or 8-quinolyl, 1-, 3-, 4-or 5-isoquinolyl, 1-, 2-or 3-indyl or the like; When substituting group is 2 when above, each substituting group can be identical or different.
Aforesaid sulfamide compound is characterized in that, described general structure (I) or compound (II) and non-toxic salt thereof are selected from:
1-benzene sulfonyl-7 methyl-3,4 dihydro-pyrimidin (4,5) also-the 2-pyrimidone;
1-tolysulfonyl-7 methyl-3,4 dihydro-pyrimidin (4,5) also-the 2-pyrimidone;
1-to fluorobenzene sulphonyl-7 methyl-3,4 dihydro-pyrimidin (4,5) also-the 2-pyrimidone;
1-to chlorobenzene sulphonyl-7 methyl-3,4 dihydro-pyrimidin (4,5) also-the 2-pyrimidone;
1-brosyl-7 methyl-3,4 dihydro-pyrimidin (4,5) also-the 2-pyrimidone;
Adjacent tolylsulfonyl-7 methyl-3,4 dihydro-pyrimidin of 1-(4,5) also-the 2-pyrimidone;
Adjacent chlorobenzene sulphonyl-7 methyl-3,4 dihydro-pyrimidin of 1-(4,5) also-the 2-pyrimidone;
Adjacent bromobenzene sulphonyl-7 methyl-3,4 dihydro-pyrimidin of 1-(4,5) also-the 2-pyrimidone;
1-ortho-nitrophenyl sulphonyl-7 methyl-3,4 dihydro-pyrimidin (4,5) also-the 2-pyrimidone;
Adjacent methyl-formiate benzene sulfonyl-7 methyl-3,4 dihydro-pyrimidin of 1-(4,5) also-the 2-pyrimidone;
3-benzene sulfonyl-7 methyl-3,4 dihydro-pyrimidin (4,5) also-the 2-pyrimidone;
3-tolysulfonyl-7 methyl-3,4 dihydro-pyrimidin (4,5) also-the 2-pyrimidone;
3-to fluorobenzene sulphonyl-7 methyl-3,4 dihydro-pyrimidin (4,5) also-the 2-pyrimidone;
3-to chlorobenzene sulphonyl-7 methyl-3,4 dihydro-pyrimidin (4,5) also-the 2-pyrimidone;
3-brosyl-7 methyl-3,4 dihydro-pyrimidin (4,5) also-the 2-pyrimidone;
Adjacent tolylsulfonyl-7 methyl-3,4 dihydro-pyrimidin of 3-(4,5) also-the 2-pyrimidone;
Adjacent chlorobenzene sulphonyl-7 methyl-3,4 dihydro-pyrimidin of 3-(4,5) also-the 2-pyrimidone;
Adjacent bromobenzene sulphonyl-7 methyl-3,4 dihydro-pyrimidin of 3-(4,5) also-the 2-pyrimidone;
3-ortho-nitrophenyl sulphonyl-7 methyl-3,4 dihydro-pyrimidin (4,5) also-the 2-pyrimidone;
Adjacent methyl-formiate benzene sulfonyl-7 methyl-3,4 dihydro-pyrimidin of 3-(4,5) also-the 2-pyrimidone.
The basic preparation method of sulfamide compound of the present invention is described below:
Figure A20041001922300061
1, with 2-methyl-4-amino-5-amine methylpyrimidine ( 2) be dissolved in the anhydrous inert solvent, slowly add carbonyl dimidazoles (or thiocarbonyl group imidazoles), stirring at room 6～30 hours, vacuum is drained solvent, the washing solid and with recrystallization can obtain compound ( 1);
2, under anhydrous inert solvent, with compound 1With 2～4 normal alkali, refluxed 4 ~ 10 hours, add 2～3 normal SULPHURYL CHLORIDE again, continue to reflux 4～8 hours.Reaction finishes, and reaction solution concentrates the back extraction, washing, and the siccative drying, column chromatography obtains target compound (I) and (II); Its hydrochloride can be prepared by this compounds and hydrochloric acid.
Employed inert solvent can be 1 in the preparation process of the present invention, 4-dioxane, methylene dichloride, trichloromethane, tetrahydrofuran (THF), acetone, ethyl acetate, ether, sherwood oil, N, single solvent in dinethylformamide or the methyl-sulphoxide or mixed solvent.
Employed alkali is sodium Metal 99.5, sodium hydride or Anhydrous potassium carbonate in the preparation process of the present invention.
Employed siccative is anhydrous sodium sulphate or anhydrous magnesium sulfate in the preparation process of the present invention.
The invention provides the application in preparation controlling weeds growth preparation of sulfamide compound and non-toxic salt thereof.
General structure provided by the present invention also is to belong within the technology of the present invention scope for the non-toxic salt of (I) or compound (II).
The compounds of this invention can be crystalline state or solvate (such as hydrate), and two states all belongs within the technology of the present invention category.
In order further to understand the present invention, provide embodiment.Specific material and used condition are intended to this explanation, its reasonable range are not construed as limiting.The reagent of not mentioning among the embodiment is buied from the market and is used with former state, except as otherwise noted.All temperature all are degree centigrade.
Embodiment 1:7-methyl-3,4-dihydro-pyrimidin (4,5) also-the 2-pyrimidone ( 1) preparation.
Weighing 1.38g (0.01mol) 2-methyl-4-amino-5-amine methylpyrimidine ( 2), adding 80ml 1,4-dioxane and 10ml water make its dissolving, slowly add 3.24g N, N ,-carbonyl dimidazoles (0.02mol), stirred overnight at room temperature.After reaction finishes, drain solvent, solid filters with the methylene dichloride repetitive scrubbing, ethyl alcohol recrystallization, obtain white solid ( 1) 1.24g, productive rate 75.6%, mp.279-282 ℃, 1H NMR (D 2O-d 2) 7.82 (s, 1H), 4.11 (s, 2H), 2.13 (s, 3H).
Adjacent bromobenzene sulphonyl-7 methyl-3,4 dihydro-pyrimidin of embodiment 2:1-(4,5) also-2-pyrimidone (I) and 3-neighbour's bromobenzene sulphonyl-7 methyl-3,4 dihydro-pyrimidin (4,5) also-preparation of 2-pyrimidone (II).
Weighing 328mg 7-methyl-3,4-dihydro-pyrimidin (4,5) also-the 2-pyrimidone ( 1) (2mmol) and 120mg NaH (4.8mmol) in the round-bottomed flask of 100ml, it is anhydrous 1 to add 60ml, 4-dioxane (sodium processings) after reflux 4-10 hour, adds the adjacent bromobenzene sulfonyl chloride of 1.124g (4.4mmol) again, continues backflow 4-8 individual hour.Reaction finishes, concentration of reaction solution, dichloromethane extraction, water washing, organic phase anhydrous Na 2SO 4Dried overnight, column chromatography for separation obtain adjacent bromobenzene sulphonyl-7 methyl-3,4 dihydro-pyrimidin of 3-(4,5) also-2-pyrimidone (I) 92mg and adjacent bromobenzene sulphonyl-7 methyl-3,4 dihydro-pyrimidin of 1-(4,5) also-2-pyrimidone (II) 188mg, overall yield 23.5%.Its hydrochloride can be prepared by products obtained therefrom and hydrochloric acid.
Other similar compound all can according to said method synthesize, as, the SULPHURYL CHLORIDE that adds in the operating process changes benzene sulfonyl chloride into, can be prepared into 1-benzene sulfonyl-7 methyl-3,4 dihydro-pyrimidin (4,5) also-2-pyrimidone and 3-benzene sulfonyl-7 methyl-3,4 dihydro-pyrimidins (4,5) also-the 2-pyrimidone; The SULPHURYL CHLORIDE that adds in the operating process changes Tosyl chloride into, can be prepared into 1-tolysulfonyl-7 methyl-3,4 dihydro-pyrimidin (4,5) also-2-pyrimidone and 3-tolysulfonyl-7 methyl-3,4 dihydro-pyrimidin (4,5) also-the 2-pyrimidone; The SULPHURYL CHLORIDE that adds in the operating process changes o-toluenesulfonyl chloride into, can be prepared into adjacent tolylsulfonyl-7 methyl-3,4 dihydro-pyrimidin of 1-(4,5) also-2-pyrimidone and adjacent tolylsulfonyl-7 methyl-3,4 dihydro-pyrimidin of 3-(4,5) also-the 2-pyrimidone; The SULPHURYL CHLORIDE that adds in the operating process changes into the fluorobenzene SULPHURYL CHLORIDE, can be prepared into 1-to fluorobenzene sulphonyl-7 methyl-3,4 dihydro-pyrimidin (4,5) also-2-pyrimidone and 3-to fluorobenzene sulphonyl-7 methyl-3,4 dihydro-pyrimidin (4,5) also-the 2-pyrimidone; The SULPHURYL CHLORIDE that adds in the operating process changes parachloroben-zenesulfonyl chloride into, can be prepared into 1-to chlorobenzene sulphonyl-7 methyl-3,4 dihydro-pyrimidin (4,5) also-2-pyrimidone and 3-to chlorobenzene sulphonyl-7 methyl-3,4 dihydro-pyrimidin (4,5) also-the 2-pyrimidone; The SULPHURYL CHLORIDE that adds in the operating process changes p-bromobenzenesulfonyl chloride into, can be prepared into 1-brosyl-7 methyl-3,4 dihydro-pyrimidin (4,5) also-2-pyrimidone and 3-brosyl-7 methyl-3,4 dihydro-pyrimidin (4,5) also-the 2-pyrimidone; The SULPHURYL CHLORIDE that adds in the operating process changes adjacent chlorobenzene sulfonyl chloride into, can be prepared into adjacent chlorobenzene sulphonyl-7 methyl-3,4 dihydro-pyrimidin of 1-(4,5) also-the close pyridine ketone of 2-and adjacent chlorobenzene sulphonyl-7 methyl-3,4 dihydro-pyrimidin of 3-(4,5) also-the 2-pyrimidone; The SULPHURYL CHLORIDE that adds in the operating process changes the ortho-nitrophenyl SULPHURYL CHLORIDE into, can be prepared into 1-ortho-nitrophenyl sulphonyl-7 methyl-3,4 dihydro-pyrimidin (4,5) also-2-pyrimidone and 3-ortho-nitrophenyl sulphonyl-7 methyl-3,4 dihydro-pyrimidin (4,5) also-the 2-pyrimidone; The SULPHURYL CHLORIDE that adds in the operating process changes adjacent methyl-formiate benzene sulfonyl chloride into, can be prepared into adjacent benzene sulfonyl-7 methyl-3,4 dihydro-pyrimidin of 1-(4,5) also-2-pyrimidone and adjacent methyl-formiate benzene sulfonyl-7 methyl-3,4 dihydro-pyrimidin of 3-(4,5) also-the 2-pyrimidone.
Table 1: the materialization data of part general formula (I) compound
Numbering The A ring ??X Proterties Melting range
???1 ??????Ph- ??O White solid ??190-192℃
???2 ??4-CH 3-Ph- ??O White solid ??198-199℃
???3 ?????4-F-Ph- ??O White solid ????210-211℃
???4 ?????4-Cl-Ph- ??O White solid ????195-196℃
???5 ?????4-Br-Ph- ??O White solid ????195-197℃
???6 ?????2-NO 2-Ph- ??O White solid ????154-156℃
???7 ?????2-Cl-Ph- ??O White solid ????192-193℃
???8 ?????2-Br-Ph- ??O White solid ????188-190℃
???9 ?????2-CH 3-Ph- ??O White solid ????191-193℃
???10 ?????2-CH 3OOC-Ph- ??O White solid ????197-199℃
Table 2: the materialization data of part general formula (II) compound:
Numbering The A ring ??X Proterties Melting range
???11 ???????Ph- ??O White solid ????190-192℃
???12 ????4-CH 3-Ph- ??O White solid ????198-199℃
???13 ????4-F-Ph- ??O White solid ????210-211℃
???14 ????4-Cl-Ph- ??O White solid ????195-196℃
???15 ????4-Br-Ph- ??O White solid ????195-197℃
???16 ????2-NO 2-Ph- ??O White solid ????154-156℃
???17 ????2-Cl-Ph- ??O White solid ????192-193℃
???18 ????2-Br-Ph- ??O White solid ????188-190℃
???19 ????2-CH 3-Ph- ??O White solid ????191-193℃
???20 ????2-CH 3OOC-Ph- ??O White solid ????197-199℃
Table 3: part of compounds 1H NMR data
Numbering ???????????????????????? 1H?NMR(δ，300M，CDCl 3，ppm)
????1 8.12(s，1H)，7.73-7.51(m，5H)，4.64-4.59(d，1H，J＝14.3)，3.70-3.66(d， J＝14.3，1H)，2.52(s，3H)
????2 8.12(s，1H)，7.61-7.58(d，J＝8.29，2H)，7.33-7.30(d，J＝8.29，2H)，4.62- 4.58(d，J＝14.31，1H)，3.72-3.68(d，J＝14.31，1H)，2.54(s，3H)，2.38(s，3H)
????3 8.15(s，1H)，7.76-7.72(m，2H)，7.21(m，2H)，4.65-4.60(d，J＝15.0，1H)， 3.71-3.66(d，J＝14.6，1H)，2.53(s，3H)
????4 8.22(s，1H)，7.76-7.55(dd，J＝8.79，4H)，4.72-4.67(d，J＝14.66，1H)，3.78- 3.73(d，J＝14.66，1H)，2.60(s，3H)
????5 8.22(s，1H)，7.75-7.65(dd，J＝9.04，4H)，4.72-4.67(d，J＝14.32，1H)，3.78- 3.74(d，J＝14.32，1H)，2.60(s，3H)
????6 8.01(s，1H)，8.46-7.84(m，4H)，4.67-4.62(d，J＝14.6，1H)，3.79-3.74(d， J＝14.2，1H)，2.57(s，3H)
????7 8.13(s，1H)，8.07-7.75(m，4H)，4.69-4.54(d，J＝14.3，1H)，3.81-3.77(d， J＝14.3，1H)，2.61(s，3H)
????8 8.11(s，1H)，7.67-8.7.47(m，4H)，4.61-4.56(d，J＝14.3，1H)，3.80-3.75(d，
J＝14.3，1H)，2.58(s，3H)
???9 8.16(s，1H)，8.04-8.00(m，1H)，7.53-7.49(m，3H)，4.68-4.63(d，J＝15.0， 1H)，3.76-3.72(d，J＝14.3，1H)，2.60(s，3H)，2.42(s，3H)
???10 8.39-8.36(d，J＝7.0，1H)，8.18-8.15(d，J＝6.4，1H)，8.06(s，1H)，7.93-7.88(t， J＝6.4，1H)，7.75-7.70(t，J＝6.4，1H)，4.59-4.54(d，J＝14.6，1H)，3.91(s，3H)， 3.71-3.66(d，J＝14.6，1H)，2.60(s，3H)
???11 8.39(s，1H)，8.10-7.57(m，5H)，5.02(s，2H)，2.61(s，3H)
???12 8.38(s，1H)，7.98-7.95(d，J＝8.78，2H)，7.37-7.34(d，J＝8.21，2H)，5.00(s， 2H)，2.60(s，3H)，2.54(s，3H)
???13 8.39(s，1H)，8.14-8.10(m，2H)，7.24-7.21(m，2H)，5.01(s，2H)，2.61(s，3H)
???14 8.39(s，1H)，8.04-8.02(d，J＝7.03，2H)，7.56-7.53(d，J＝9.3，2H)，7.35(s， 1H)，5.01(s，2H)，2.62(s，3H)
???15 8.39(s，1H)，7.96-7.69(dd，J＝9.38，4H)，5.00(s，2H)，2.61(s，3H)
???16 8.46(s，1H)，7.83-7.80(m，4H)，5.08(s，2H)，2.62(s，3H)
???17 8.46(s，1H)，7.58-7.50(m，4H)，5.19(s，2H)，2.62(s，3H)
???18 8.42(s，1H)，8.39-8.36(d，J＝7.53，1H)，7.72-7.69(d，J＝8.28，1H)，7.55- 7.48(m，2H)，5.23(s，2H)，2.62(s，3H)
???19 8.42(s，1H)，8.14-7.42(m，4H)，5.10(s，2H)，2.63(s，3H)，2.54(s，3H)
???20 8.43(s，1H)，7.70-7.67(m，4H)，5.08(s，2H)，3.93(s，3H)，2.62(s，3H)
The mensuration of weeding activity
Supplying in the biological activity test of test agent above-mentioned, as reference, found that this compounds has good removing activity and kills the grass spectrum with weedicides such as commercial tribenuron-methyls, wherein compound 10,16, and 17,18 grades have good herbicidal activity.
The above, it only is preferred embodiment of the present invention, be not that the present invention is done any pro forma restriction, every foundation technical spirit of the present invention all still belongs in the scope of technical solution of the present invention any simple modification, equivalent variations and modification that above embodiment did.

Claims (8)

1, a kind of sulfamide compound is characterized in that, it is general structure (I) or compound (II) and non-toxic salt thereof:
Figure A2004100192230002C1
In the formula: ring A is phenyl ring or has substituent phenyl ring more than; X is Sauerstoffatom or sulphur atom.
2, sulfamide compound according to claim 1; it is characterized in that the substituting group that described ring A has comprises: halogen, nitro, cyano group, hydroxyl, sulfonic group, ester group, carboxyl, alkyl or have substituent alkyl, alkoxyl group, aryl, aryloxy, acyl group, acyloxy, heterocyclic radical more than one.
3, sulfamide compound according to claim 2 is characterized in that: described halogen comprises fluorine, chlorine, bromine, iodine; Described alkyl is C 1-8The substituting group that alkyl, alkyl have comprises: halogen, hydroxyl, C 1-6Alkoxyl group; Described alkoxyl group is C 1-6Alkoxyl group; Described aryl is C 6-14Aryl; Described aryloxy is C 6-14Aryloxy; Described acyl group comprises formyl radical, ethanoyl, propionyl, formamyl; Described acyloxy comprises acetoxyl group, propionyloxy, methoxycarbonyl oxygen base, ethoxy carbonyl oxygen base, propoxycarbonyl oxygen base, butoxy carbonyl oxygen base, carbamoyloxy; Described heterocyclic radical is a 5-10 unit heterocyclic radical, preferred 5 yuan or 6 yuan of heterocyclic radicals.
4, sulfamide compound according to claim 1 is characterized in that, described general structure (I) or compound (II) and non-toxic salt thereof are selected from:
1-benzene sulfonyl-7 methyl-3,4 dihydro-pyrimidin (4,5) also-the 2-pyrimidone;
1-tolysulfonyl-7 methyl-3,4 dihydro-pyrimidin (4,5) also-the 2-pyrimidone;
1-to fluorobenzene sulphonyl-7 methyl-3,4 dihydro-pyrimidin (4,5) also-the 2-pyrimidone;
1-to chlorobenzene sulphonyl-7 methyl-3,4 dihydro-pyrimidin (4,5) also-the 2-pyrimidone;
1-brosyl-7 methyl-3,4 dihydro-pyrimidin (4,5) also-the 2-pyrimidone;
Adjacent tolylsulfonyl-7 methyl-3,4 dihydro-pyrimidin of 1-(4,5) also-the 2-pyrimidone;
Adjacent chlorobenzene sulphonyl-7 methyl-3,4 dihydro-pyrimidin of 1-(4,5) also-the 2-pyrimidone;
Adjacent bromobenzene sulphonyl-7 methyl-3,4 dihydro-pyrimidin of 1-(4,5) also-the 2-pyrimidone;
1-ortho-nitrophenyl sulphonyl-7 methyl-3,4 dihydro-pyrimidin (4,5) also-the 2-pyrimidone;
Adjacent methyl-formiate benzene sulfonyl-7 methyl-3,4 dihydro-pyrimidin of 1-(4,5) also-the 2-pyrimidone;
3-benzene sulfonyl-7 methyl-3,4 dihydro-pyrimidin (4,5) also-the 2-pyrimidone;
3-tolysulfonyl-7 methyl-3,4 dihydro-pyrimidin (4,5) also-the 2-pyrimidone;
3-to fluorobenzene sulphonyl-7 methyl-3,4 dihydro-pyrimidin (4,5) also-the 2-pyrimidone;
3-to chlorobenzene sulphonyl-7 methyl-3,4 dihydro-pyrimidin (4,5) also-the 2-pyrimidone;
3-brosyl-7 methyl-3,4 dihydro-pyrimidin (4,5) also-the 2-pyrimidone;
Adjacent tolylsulfonyl-7 methyl-3,4 dihydro-pyrimidin of 3-(4,5) also-the 2-pyrimidone;
Adjacent chlorobenzene sulphonyl-7 methyl-3,4 dihydro-pyrimidin of 3-(4,5) also-the 2-pyrimidone;
Adjacent bromobenzene sulphonyl-7 methyl-3,4 dihydro-pyrimidin of 3-(4,5) also-the 2-pyrimidone;
3-ortho-nitrophenyl sulphonyl-7 methyl-3,4 dihydro-pyrimidin (4,5) also-the 2-pyrimidone;
Adjacent methyl-formiate benzene sulfonyl-7 methyl-3,4 dihydro-pyrimidin of 3-(4,5) also-the 2-pyrimidone.
5, the preparation method of described sulfamide compound of claim 1 and non-toxic salt thereof is characterized in that, comprises the steps:
Under anhydrous inert solvent, with compound 1 and 2～4 normal alkali, refluxed 4 ~ 10 hours, add 2～3 normal SULPHURYL CHLORIDE again, continue to reflux 4～8 hours; Reaction finishes, and reaction solution concentrates the back extraction, washing, and the siccative drying, column chromatography obtains target compound (I) and (II).
6, according to the preparation method of right 5 described sulfamide compounds and non-toxic salt thereof, it is characterized in that, described inert solvent is 1,4-dioxane, methylene dichloride, trichloromethane, tetrahydrofuran (THF), acetone, ethyl acetate, ether, sherwood oil, N, single solvent in dinethylformamide or the methyl-sulphoxide or mixed solvent.
According to the preparation method of right 5 described sulfamide compounds and non-toxic salt thereof, it is characterized in that 7, described alkali is sodium Metal 99.5, sodium hydride or Anhydrous potassium carbonate; Described siccative is anhydrous sodium sulphate or anhydrous magnesium sulfate.
8, claim 1 or 2 or 3 or 4 described sulfamide compounds and non-toxic salt thereof the application in preparation controlling weeds growth preparation.
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CN102491977A (en) * 2011-11-28 2012-06-13 江西师范大学 1-substituted benzene oxymethylene-8-alkylthio-10-methylthio pyrimido [5,4-e]-1,2,triazole [1,5-c] pyrimidine possessing herbicidal activity and its preparation method

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JP3911236B2 (en) * 2000-11-03 2007-05-09 ダウ・アグロサイエンス・エル・エル・シー N- (5,7-dimethoxy [1,2,4] triazolo [1,5-a] pyrimidin-2-yl) arylsulfonamide compounds and their use as herbicides
KR20040004427A (en) * 2000-11-03 2004-01-13 다우 아그로사이언시즈 엘엘씨 N-([1,2,4]Triazoloazinyl) thiophenesulfonamide compounds as herbicides

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CN102491977A (en) * 2011-11-28 2012-06-13 江西师范大学 1-substituted benzene oxymethylene-8-alkylthio-10-methylthio pyrimido [5,4-e]-1,2,triazole [1,5-c] pyrimidine possessing herbicidal activity and its preparation method
CN102491977B (en) * 2011-11-28 2014-06-11 江西师范大学 1-substituted benzene oxymethylene-8-alkylthio-10-methylthio pyrimido [5,4-e]-1,2,triazole [1,5-c] pyrimidine possessing herbicidal activity and preparation method thereof
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