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| Synthesis of Sulfonylurea Herbicides Imazosulfuron and Its Derivatives |
| SHI Gui-zhen, GE Jun-ying, DOU Jian-zhi, ZHANG Zai-zhen |
| Weifang Engineering Vocational College, Qingzhou 262500, China |
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Abstract Taking 2-aminopyridine and chlorosulfonic acid as raw material, the intermediate 2-chloroimidazo[1,2-a]pyridine-3-sulfonamide was first synthesized through the reaction of chlorosulfonation and ammonolysis. Then, five kinds of 4,6-substituted and 4,5,6-substituted 2-aminopyrimidine compounds were synthesized through condensation reaction of carbamidine and β-dicarbonyl compounds. Next, sulfonyl carbamic acid benzyl ester was obtained through the reaction of sulfonamide and phenyl chloroformate. At last, through addition reaction of the resulting compound with 2-amino pyrimidine compounds imazosulfuron and its derivates ( compounds 1-5 ) were obtained. The structure of the target products were analyzed and affirmed by melting point, Fourier transform infrared spectra, mass spectra, hydrogen spectra of nuclear magnetic resonance and other methods.
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| [ 1 ] Yasuo I, Kazunari O, Shigeyuki I, et al. Studies on sulfonylureas with fused heterocycles. Part 1. Synthesis of novel herbicidal sulfonylurea compounds with an imidazo[1,2-α]pyridine moiety[J]. Journal of Pesticide Science ( International Edition )1993，18：175-182.
[ 2 ] Mikata K，Ohta K，Tashiro S. Adsorption and desorption of herbicide imazosulfuron in soils[ J ]. J Pestic Sci，2000（25 ）：212-216.
[ 3 ] Kuk YI, Kwon OD, Jung HI, et al. Cross-resistance pattern and alternative herbicides for Rotala indica resistant to imazosulfuron in Korea[ J ]. Pesticide Biochemistry and Physiology, 2002（74 ）：129-138.
[ 4 ] Morrica P，Fidente P，Seccia S. Identification of photoproducts from imazosulfuron by HPLC[ J ]. Biomedical Chromatography，2004（18 ）：450-456.
[ 5 ] Morrica P，Fidente P,Seccia S，et al. Degradation of imazosu-lfuron in different soils-HPLC determination[ J ]. Biomedical Chromatography，2002（16 ）：489-494.
[ 6 ] Morrica P，Barbato F，Della lacovo R，et al. Kinetics and me-chanism of imazosulfuron hydrolysis[ J ]. Journal of Agricultural and Food Chemistry，2001，49（8 ）：3 816-3 820.
[ 7 ] Morrica P，Giordano A，Seccia S，et al. Degradation of imazo-sulfuron in soil[ J ]. Pest Management Science，2001, 57 ( 4 )： 360-365.
[ 8 ] Mikata K，Yamamoto A，Tashiro S. Degradation of imazosulfu-ron in flooded soils[ J ]. Nippon Noyaku Gakkaishi，1996, 21 ( 2 )：171-177.
[ 9 ] Yasuo I，Kazunari O，Tatsuo N，et al. Preparation of ( hetero-arylsulfonyl ) ureas as herbicides：EP, 238070[ P ].1987-09-23.
[10] Miki H.，Ishida Y.. Process of producing N-heterocyclylsulfonyl-N'-py-rimidinylurea derivatives as herbicides：EP，305939 A1[ P ]. 1989-03-08.
[11] Tatsuo N，Kazunari O，Shigeyuki I，et al. Production of condensed heterocyclic rings： JP，1316379[ P ].1989-12-21.
[12] 刘长令. 新型稻田除草剂咪唑黄隆[ J ]. 农药, 1995, 34 （9 ）：27-30.
[13] 孔繁蕾，王兰青，胡新华，等. 2-氨基嘧啶类系列化合物的合成[ J ]. 化学世界，1991，32（6 ）：254-257. |
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