新型脲嘧啶及苯并噁嗪衍生物的合成与生物活性研究
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摘要
21世纪的农药在高效、安全、经济、环境友好等方面提出了更高的要求。四取代苯类除草剂为原卟啉原氧化酶(protox)抑制剂,属需光型除草剂,其独特的除草机制可保证动植物之间的良好选择性,具有十分广阔的发展前景。
本文以商品化的protox抑制剂氟丙嘧草酯、丙炔氟草胺等除草剂为先导,针对它们物理性能或生物活性等方面的某些缺陷,采用活性亚结构拼接、生物电子等排体等农药分子设计方法,设计并合成了N-苯基脲嘧啶-2-异吲哚二酮、N-苯基脲嘧啶-3-芳(烷)基脲、N-苯基脲嘧啶-N-苯氧乙(丙)酰胺、N-苯基脲嘧啶-N-芳(烷)酰胺、吡咯烷酮取代苯并噁嗪、N-苯并噁嗪-2-异吲哚二酮乙酰胺、N-苯并噁嗪苯甲酰胺和丙炔氟草胺碘加成物等八个系列九类共92个具有潜在protox抑制剂活性的新型脲嘧啶和苯并噁嗪衍生物,所有化合物结构经核磁共振、质谱、红外光谱、元素分析等检测方法进行了确证。首次在苯基取代脲嘧啶结构类型中引入脲基团和苯氧丙酰胺基团,首次在苯并噁嗪衍生物中引入吡咯烷酮基团,研究结果丰富和扩展了四取代苯和protox抑制剂的结构类型。
采用农药生物活性测定标准操作程序测试了所合成的新化合物的除草活性,发现一些化合物表现出较高的protox抑制活性,如2个N-苯基脲嘧啶-N-苯氧丙酰胺衍生物、2个N-苯基脲嘧啶-N-烷酰胺衍生物的除草活性和对作物安全性与先导化合物氟丙嘧草酯基本相当;4个N-苯基脲嘧啶-1-烷基脲衍生物在75 g ai/ha剂量下芽前或芽后施用对苘麻、藜、凹头苋等双子叶杂草和马唐、稗草、狗尾草等单子叶杂草均表现出80%以上除草活性。杂草中毒症状有叶片白化、卷曲、灼伤和坏死等,属protox抑制剂典型的除草特征。
解析了化合物N-(3-氧-4-乙基-7-氟-2H-[1,4]苯并噁嗪-6-基)-2-硝基-4-甲磺酰基苯甲酰胺和化合物2-[4-(2,3-二碘-丙-2-烯基)-7-氟-3-氧-3,4-二氢-2H-[1,4]l苯并噁嗪-6-基]-4,5,6,7-四氢-2H-异吲哚-1,3-二酮的单晶结构,通过分析~1H NMR与X-射线晶体衍射实验计算数据,揭示了分子中环的构型和氢键情况,为进一步设计具有生物活性的化合物提供了有价值的参考信息和实验数据。
围绕具有自主知识产权的新化合物B2005工业技术开发的需要,发现了以醋酸为溶剂、氯化碘为碘化剂取代丙炔氟草胺的端炔氢合成B2055的新合成方法,具有反应时间短,收率高、反应条件温和等特点;与原有采用碘代丁二酰亚胺为碘化剂的方法比较,收率基本相当,含量高于95%,较大幅度地降低了原材料成本,具有较大的应用价值。
通过新化合物结构与除草活性之间的定性构效关系研究,揭示了脲嘧啶、苯并噁嗪衍生物结构与活性之间的规律,研究成果对于今后protox抑制剂类新农药的分子设计和先导优化研究具有指导意义。
In the 21~(th) century, pesticide must have the characteristics of high effect, safety, low cost and environmentally-friend. Tetra-substituded benzene herbicides are Protoporphyriinogen oxidase (protox) inhibitors and light-dependent herbicides, which will be found a wider application because their unique herbicidal mechanism can ensure very good selectivity between human, animals and plants.
To overcome limitations of some lead compounds in physical property and biological activity, some novel compounds with latent protox inhibiting activity were designed by choosing commercial protox inhibitor butafenacil, flumioxazin and other herbicides as lead compounds based on pesticide molecular design technologies, such as activity sub-structure connecting and bioisosteric replacement; 9 kinds 92 novel uracil and benzoxazine derivatives were prepared and purified, and these compounds could be divided into 8 series: N-phenyluracil-2-isoindolinedione, N-phenyluracil-3-phenyl(alkyl)ur-ea, N-phenyluracil-N-acet(propan)amide, N-phenyluracil-N-benz(alkyl)am-ide, oxopyrrolidine substituted benzoxazine, N-benzoxazine-2-isoindoline-dione acetamide, N-benzoxazinebenzamide and two iodine substituted flumioxazin. Their structures were confirmed by ~1H NMR, IR, mass spectroscopy and elemental analysis. The first introduction of phenox-ypropanamide and urea group into phenyluracil derivatives and that of 2-oxo-pyrrolidine group into benzoxazine derivatives expanded the chemical structural types of tetra-substituded benzene and protox inhibitors.
The bioassays of preliminary herbicidal activity were carried out according to the standard operation procedure of pesticide bioassay, and the results showed that many compounds exhibited higher inhibiting protox activity. For example, two compound of N-phenyluracil-N-propanamide derivatives and two compound of N-phenyluracil-N-alkylamide derivatives had comparable herbicidal activity as butafenacil, four compounds of N-phenyluracil-1-alkyurea derivatives possessed more than 80% herbicidal efficiency at 75 g ai/ha in both pre- and post-emergence treatments against both dicotyledon weeds such as Abutilon theophrasti M, Chenopodiun album L, Amaranthus retroflexus L and monocotyledon weeds such as Digitaria sanguinalis L, Echinochloa crus-galli L, Setaria viridis L. The injury symptoms against weeds included leaf cupping, crinkling, bronzing and necrosis, typical of protox inhibitor herbicides.
The crystal of N-(4-ethyl-7-fluoro-3-oxo-3,4-dihydro-2H-benzo[b][1 ,4]-oxazin-6-yl)-4-(methylsulfonyl)-2-nitrobenzamideand2-{4-[(E)-2,3-diiodoa-llyl]-7-fluoro-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl}-4,5,6,7-tetrah-ydro-2H-isoindole-1,3-dione was parsed. The results of ~1H NMR and X-ray crystallographic measurement showed the information of ring conformations and hydrogen bonds in the molecule, which offered a valuable information and fact evidence for the further design of bio-active compounds.
A new synthesis method of B2055 was discovered, in which chloride iodine was used as iodide reagent and acetic acid as solvent, with 90.7% yield and 95% purity. The method showed more economical and industrialized value.
Qualitative study on the relationship between chemical structure and herbicidal activity outlined their orderliness. The results could be used to guide the further research for the design of novel pesticide molecules and the modification of lead compounds.
本文以商品化的protox抑制剂氟丙嘧草酯、丙炔氟草胺等除草剂为先导,针对它们物理性能或生物活性等方面的某些缺陷,采用活性亚结构拼接、生物电子等排体等农药分子设计方法,设计并合成了N-苯基脲嘧啶-2-异吲哚二酮、N-苯基脲嘧啶-3-芳(烷)基脲、N-苯基脲嘧啶-N-苯氧乙(丙)酰胺、N-苯基脲嘧啶-N-芳(烷)酰胺、吡咯烷酮取代苯并噁嗪、N-苯并噁嗪-2-异吲哚二酮乙酰胺、N-苯并噁嗪苯甲酰胺和丙炔氟草胺碘加成物等八个系列九类共92个具有潜在protox抑制剂活性的新型脲嘧啶和苯并噁嗪衍生物,所有化合物结构经核磁共振、质谱、红外光谱、元素分析等检测方法进行了确证。首次在苯基取代脲嘧啶结构类型中引入脲基团和苯氧丙酰胺基团,首次在苯并噁嗪衍生物中引入吡咯烷酮基团,研究结果丰富和扩展了四取代苯和protox抑制剂的结构类型。
采用农药生物活性测定标准操作程序测试了所合成的新化合物的除草活性,发现一些化合物表现出较高的protox抑制活性,如2个N-苯基脲嘧啶-N-苯氧丙酰胺衍生物、2个N-苯基脲嘧啶-N-烷酰胺衍生物的除草活性和对作物安全性与先导化合物氟丙嘧草酯基本相当;4个N-苯基脲嘧啶-1-烷基脲衍生物在75 g ai/ha剂量下芽前或芽后施用对苘麻、藜、凹头苋等双子叶杂草和马唐、稗草、狗尾草等单子叶杂草均表现出80%以上除草活性。杂草中毒症状有叶片白化、卷曲、灼伤和坏死等,属protox抑制剂典型的除草特征。
解析了化合物N-(3-氧-4-乙基-7-氟-2H-[1,4]苯并噁嗪-6-基)-2-硝基-4-甲磺酰基苯甲酰胺和化合物2-[4-(2,3-二碘-丙-2-烯基)-7-氟-3-氧-3,4-二氢-2H-[1,4]l苯并噁嗪-6-基]-4,5,6,7-四氢-2H-异吲哚-1,3-二酮的单晶结构,通过分析~1H NMR与X-射线晶体衍射实验计算数据,揭示了分子中环的构型和氢键情况,为进一步设计具有生物活性的化合物提供了有价值的参考信息和实验数据。
围绕具有自主知识产权的新化合物B2005工业技术开发的需要,发现了以醋酸为溶剂、氯化碘为碘化剂取代丙炔氟草胺的端炔氢合成B2055的新合成方法,具有反应时间短,收率高、反应条件温和等特点;与原有采用碘代丁二酰亚胺为碘化剂的方法比较,收率基本相当,含量高于95%,较大幅度地降低了原材料成本,具有较大的应用价值。
通过新化合物结构与除草活性之间的定性构效关系研究,揭示了脲嘧啶、苯并噁嗪衍生物结构与活性之间的规律,研究成果对于今后protox抑制剂类新农药的分子设计和先导优化研究具有指导意义。
In the 21~(th) century, pesticide must have the characteristics of high effect, safety, low cost and environmentally-friend. Tetra-substituded benzene herbicides are Protoporphyriinogen oxidase (protox) inhibitors and light-dependent herbicides, which will be found a wider application because their unique herbicidal mechanism can ensure very good selectivity between human, animals and plants.
To overcome limitations of some lead compounds in physical property and biological activity, some novel compounds with latent protox inhibiting activity were designed by choosing commercial protox inhibitor butafenacil, flumioxazin and other herbicides as lead compounds based on pesticide molecular design technologies, such as activity sub-structure connecting and bioisosteric replacement; 9 kinds 92 novel uracil and benzoxazine derivatives were prepared and purified, and these compounds could be divided into 8 series: N-phenyluracil-2-isoindolinedione, N-phenyluracil-3-phenyl(alkyl)ur-ea, N-phenyluracil-N-acet(propan)amide, N-phenyluracil-N-benz(alkyl)am-ide, oxopyrrolidine substituted benzoxazine, N-benzoxazine-2-isoindoline-dione acetamide, N-benzoxazinebenzamide and two iodine substituted flumioxazin. Their structures were confirmed by ~1H NMR, IR, mass spectroscopy and elemental analysis. The first introduction of phenox-ypropanamide and urea group into phenyluracil derivatives and that of 2-oxo-pyrrolidine group into benzoxazine derivatives expanded the chemical structural types of tetra-substituded benzene and protox inhibitors.
The bioassays of preliminary herbicidal activity were carried out according to the standard operation procedure of pesticide bioassay, and the results showed that many compounds exhibited higher inhibiting protox activity. For example, two compound of N-phenyluracil-N-propanamide derivatives and two compound of N-phenyluracil-N-alkylamide derivatives had comparable herbicidal activity as butafenacil, four compounds of N-phenyluracil-1-alkyurea derivatives possessed more than 80% herbicidal efficiency at 75 g ai/ha in both pre- and post-emergence treatments against both dicotyledon weeds such as Abutilon theophrasti M, Chenopodiun album L, Amaranthus retroflexus L and monocotyledon weeds such as Digitaria sanguinalis L, Echinochloa crus-galli L, Setaria viridis L. The injury symptoms against weeds included leaf cupping, crinkling, bronzing and necrosis, typical of protox inhibitor herbicides.
The crystal of N-(4-ethyl-7-fluoro-3-oxo-3,4-dihydro-2H-benzo[b][1 ,4]-oxazin-6-yl)-4-(methylsulfonyl)-2-nitrobenzamideand2-{4-[(E)-2,3-diiodoa-llyl]-7-fluoro-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl}-4,5,6,7-tetrah-ydro-2H-isoindole-1,3-dione was parsed. The results of ~1H NMR and X-ray crystallographic measurement showed the information of ring conformations and hydrogen bonds in the molecule, which offered a valuable information and fact evidence for the further design of bio-active compounds.
A new synthesis method of B2055 was discovered, in which chloride iodine was used as iodide reagent and acetic acid as solvent, with 90.7% yield and 95% purity. The method showed more economical and industrialized value.
Qualitative study on the relationship between chemical structure and herbicidal activity outlined their orderliness. The results could be used to guide the further research for the design of novel pesticide molecules and the modification of lead compounds.
引文
[1]唐除痴,李煜昶,陈彬,等.农药化学.天津:南开大学出版社,1998:3-5
[2]傅向升.农药大国的喜与优.农化市场十日迅,2007,(7):12-14
[3]谷业理,黄存达.农田杂草化学防治.北京:科学普及出版社,1998:1-5
[4]农田杂草的防治.http://www.agrionline.net.cn/new_agri/list.asp?id=2644
[5]张朝贤.我国农田杂草治理的差距与亟待解决的问题.http://zbxh.jaas.ac.cn/2005/5-12/143940.html
[6]除草剂.http://baike.baidu.com/view/48545.htm
[7]臧开保,王晓光.农药的研究与趋势.湖南化工,2000,30(3):1-8
[8]苏少泉.除草剂作用靶标与新品种创制.北京:化学工业出版社,2001.1
[9]魏福香.除草剂的现状与发展趋势.安徽农业,1999,(3):8-9
[10]胡笑形.2009年全球作物保护市场预测与中国农药的机遇.中国农药,2005,(3):11-23
[11]毕璋友,洪流.中国农药工业的现状及发展趋势.安徽农业科学,2005,33(8):1497-1450
[12]王律先.2006年全国农药生产回顾及2007年展望.中国农药,2007,(2):43-51
[13]梁丽娜,郭平毅,李奇峰.中国除草剂产业现状-面临的问题及发展趋势.中国农学通报,21(10):321-323
[14]黄明智.异吲哚-1,3-二酮衍生物的合成、生物活性及构效关系研究.[博士学位论文],长沙,中南大学,2006
[15]欧晓明,唐德秀.除草剂作用原理研究的新进展.世界农业,2000,(10):28-30
[16]苏少泉.除草剂作用靶标的分类与使用.农药,1998,37(11):1-7
[17]Evans,D A.New era,new challenges,new solutions.In:Proceedings of Brighton Crop Proteetion Conference-Pests & Diseases.Brighton:BCPC,2000:3-18
[18]刘长令.除草剂研究开发的新进展和发展趋势.江苏化工,2000,28(8):15-20
[19]苏少泉.除草剂开发面临的问题与发展趋势.现代化农业,2002,(1):5-8
[20]胡笑形.全球农药公司继续兼并重组.国际化工信息,2002,(8),22-24
[21]张培.农药企业将迎来整合新挑战.农药,2006,45(6),409
[22]陈文斌,金桂玉.含稠杂环新农药的研究进展.农药学学报,2000,2(4):1-10
[23]侯仲轲.具有生物活性的新颖杂环化合物.新农药,2002,(2):25-28
[24]钱旭红,徐晓勇,宋恭华,等.二十一世纪新农药研发趋势.贵州大学学报(自然科学版),2003,20(1),83-90
[25]张一宾,钱跃言.含氟农药的结构、特性及研究开发概况.江苏化工,2002,30(3):5-10,47
[26]王宁,薛振祥.当今热点农药的含氟中间体开发.现代农药,2004,3(5):1-7,45
[27]梁诚.含氟农药的研究开发与生产应用(上).新农药,2005,(2):19-24
[28]梁诚.含氟农药的研究开发与生产应用(下).新农药,2005,(3):7-12
[29]车超,覃兆海.手性农药合成研究进展.化学通报,2002,65:w042
[30]谭效松,贺红武.除草剂的作用靶标与作用模式.农药,2005,44(12):533-541
[31]Ward E,Bernasconi P.Target-based discovery of crop protection chemicals.Nat Biotechnol,1999,(17):618-619
[32]Wolfgang L,Fmderik B,Andreas R,et al.Target-based discovery of novel herbicide.Curt Opin Plant Biol,2004,(7):219-225
[33]王涛,贺红武,袁均林.丙酮酸脱氢酶系:除草剂品种的新靶标.应用化学,2003,20(7):613-617
[34]李茹,赵桂东,熊战之,等.浅议化学农药.现代农业科技--种子与种苗篇,2005,(9):51-52
[35]聂开晟,范志金,刘长令.三酮类除草剂的研究新进展.农药,2006,45(1):4-7
[36]马娟,董全皋.微生物除草剂与生物安全.山东农药信息,2006,(5):21-23
[37]苏少泉,滕春红,赵世君.最近15年世界转基因抗除草剂作物.农药研究与应用,2006,(3):1-4
[38]马俊,王金艳,李刚.转基因作物的生物安全及安全管理的几点思考.杂粮发作物,2007,27(3):248-249
[39]沈孝宙.转基因食物争论的焦点.百科知识,2007,(6):9-11
[40]李海屏.20世纪80年代以来世界除草剂新品种开发进展及特点(续).农药科学与管理,2005,25(5):26-29
[41]Hirai K.Structural evolution and synthesisi of diphenyl ethers,yclic imides and related compounds.In:Boger P,Wakabayashi K,eds.Peroxidizing Herbicides.Berlin:Springer,1999.15-72
[42]Iwataki I.Recent advances in peroxidizing herbicides(patent overview).In:Boger P,Wakabayashi K,eds.Peroxidizing Herbicides.Berlin:Springer,1999.73-90
[43]Scherman T D,Duke M V,Clark R D,et al.Pyrazole phenyl ether herbicides inhibit protoporphyrinogen oxidase.Pestic.Biochem.Physiol.,1991,40(3):236-245
[44]Nagano E,Hashimoto S.Tetrahydrophthalimides,and their production and use.EP 0061741,1987-10-06
[45]Hirai K,Futikami T.Oxazolidinedione derivatives,process for their preparation,and herbicides containing the same.WO 8702357,1987-04-23
[46]Jean M,Roger B.5-t-Butyl-3-phenyl-2-oxadiazolones.US 3385862,1968-05-28
[47]Nagano E.2-Phenyl-4,5,6,7-tetrahydro-2h-indazole derivative,its preparation,and herbicide comprising it as active ingredient.JP 60252465,1985-12-13
[48]Miura Y.3-Substituted phenylpyrazole derivative or its salt and herbicide.JP 372460,1991-03-27
[49]Dutra G A,Hamper B C.Herbicidal substituted aryl-haloalkyl pyrazoles.WO 9206962,1992-04-30
[50]Yamagich M,Watase Y.Thiadiazabicyclononane derivatives and herbicidal compositions.EP 0273417,1988-07-06
[51]Theodoridis G.Herbicidal aryl triazolinones.US 4818275,1989-04-04
[52]Poss K M.Herbicidal triazolinones.WO 9002120,1990-03-08
[53]Ganzer M,Franke W.Heteroeyclic substituted azoles and azines,process for their preparation and their use as an agent with herbicide activity.EP 0311135,1989-04-12
[54]Loux H M.Method for the control of undesirable vegetation.US 3235361,1966-02-15
[55]Soboczenski E J.3,5-Disubstitued uraeils.US 3352863,1967-11-14
[56]Loux H M.3-Bicycloalkyl-6-methyluracil.US 3360522,1967-12-26
[57]Komori T,Sanemitsu Y.Uracil compounds and use thereof.US 6403534,2002-6-13
[58]刘长令.世界农药大全(除草剂卷).化学工业出版社,北京,2002,146-147.
[59]刘长令.噁二嗪类杀虫剂的创制经纬.农药,2002,41(10),47-48.
[60]Sting A R,Siegrist U E,Baumeister P E.Preparation of 3-aryl-uracil derivative useful as herbicide.DE 19741411,1998-03-26
[61]Andree R,Drewes M W.Dollinger,M.Heterocyelyluracils.US 6184183,2001-02-06
[62]Andree R,Drewes M W,Haas W.Heterocyclyluracils.US 6187716,2001
[63]Andree R,Drewes M W,Dollinger,M.Substituted phenyl uracils.US 6432879,2002-08-12.
[64]Nishio S.Herbicide composition.EP 1459628,2004-09-22
[65]Theodoridis G.Herbieical 2-[(4-heterocyclic-phenoxymethyl)phenoxy]-alkanoates.US 5262390,1993-11-16
[66]Theodoridis G.,Crawford S D.Herbicidal isoindolinonyl-and 3,4-dihydroisoquinolo-nyl substituted heterocycles.US 6277847,2001-08-21
[67]Reinhard R,Hamprecht G,Zagar C.3-[Benz(ox/thi)azol-7-yl]-1H-pyrimidine-2,4-diones.WO 0028822,2000-05-25
[68]Suchy M,Winternitz P,Zeller M.Heterocyclic substituted uracil derivatives.US 5232898,1993-08-03
[69]Klintz R G.,Schaefer P.3-Aryluracils and intermediates for their preparation.WO 9628442,1996-09-19
[70]Crawford S D.Cycloimido-substituted benzofused heterocyclic herbicides.WO 9838188,1998-09-03
[71]Takano M,Kawamura S,Komori T.Condensed heterocylic compounds and herbicides containing them.US 6586368,2003-07-01
[72]Marvin J K,Harvey R W.Method for the preparation of benzyluracils.US 5817814,1998-10-06
[73]Menke,O.;Hamprecht,G.;Menges,M.1-Amino-3-benzyl uracils.WO 9842682,1998-10-01
[74]Konz M J,Wendt H R.Improved method for the preparation of benzyluracils.WO 9850369,1998-11-12
[75]Sanemitsu Y,Tohyama Y.Uracil herbicides.WO 0021936,2000-04-20
[76]Puttner R,Bohner J.Herbicidal 3-arylamino-6-trifluoromethyluracils.US 5919732,1999-07-06
[77]Menke O,Gotz R,Rack M.New 3-aryl-methyl-uracil derivatives.DE 19738084,1999-03-04
[78]Andree R,Drewes M W.Substituted arylalkyluracils.WO 9840362,1998-09-17
[79]Menke O,Klintz R,Hamprecht G.1-Amino-3-benzyluracils.US 6268311,2001-07-31
[80]刘长令.世界农药大全(除草剂卷).北京,化工工业出版社,2002,3-6.
[81]杨道武,谌伟民,等.2H-[1,4]苯并噁嗪类化合物合成研究进展.精细化工中间体,2005,35(6):7-10
[82]Virtanen A I,Hietala P K.The structures of the precursors of benzoxazolinone in rye plants.Ⅱ.Suom.Kemistil.B.1959,32B,252
[83]Hamilton R H,Bandurski R S.Isolation and characterization of a cyclic hydroxamate from Zea mays.Cereal Chem.1962,39:107-113
[84]Argandona V H,Luza J G.,Niemeyer H M.,et al.Role of hydroxamic acids in the resistance of cereals to aphids.Phytochemistry.1980,19:1665-1668
[85]Bravo H R,Lazo W.Antialgal and antifungal activity of natural hydroxamic acids and related compounds.J.Agric.Food Chem.,1996,44:1569-1571
[86]Cambier V,Hance T.Variation of DIMBOA and related compounds content in relation to the age and plant organ in maize.Phytochemistry.2000,53:223-229
[87]Macias F A,Marin D,Oliveros-Bastidas A.,et al.Structure-Activity Relationships (SAR)Studies of Benzoxazinones,Their Degradation Products and Analogues, Phytotoxicity on Standard Target Species (STS). J. Agric. Food Chem., 2005, 53: 538-548
[88] Macias F A, Chinchilla N, Varela R M., et al. Structure-Activity Relationship Studies of Benzoxazinones and Related Compounds. Phytotoxicity on Echinochloa crus-galli (L.) P. Beauv. J. Agric. Food Chem., 2005, 53: 4373-4380
[89] Larsen E, Christensen L P. Simple method for large scale isolation of the cylic Arylhydroxamic Acid DIMBOA from maize(zea maysl). J. Agric. Food Chem., 2000,48: 2556-2558
[90] Mitsuaki T, Seiji T, Masanori W. Benzoxazine Compounds Useful as Herbicides. US 5041154,1989-01-23
[91] Naoko K M, Harukazu F K., et al.. Phenoxy or Pyridyloxy-2H-1,4-Benzoxazine-3-one Derivative and Herbicide Containing Same as Active Ingredient. US 5338719,1993-04-12
[92] Poulson R, Polglase W J. The enzymic conversion of protoporphyrinogen IX to protoporphyrin IX. Protoporphyrinogen oxidase activity in mitochondrial extracts of Saccharomyces cerevisiae. J. Biol. Chem., 1975,250: 1269-1274
[93] Poulson R. The enzymic conversion of protoporphyrinogen IX to protoporphyrin IX in mammalian mitochondria. J. Biol. Chem., 1976, 251: 3730-733
[94] Camadro J M, Urban-Grimal D, Labbe P. A new assay for Protoporphyrinogen oxidase- evidence for a total deficiency in that activity in a heme-less mutant of Saccharomyces cerevisiae. Biochem. Biophys. Res. Commun., 1982,106: 724-730
[95] Adomat C, Boger P. Cloning, sequence, expression and characterization of protoporphyrinogen IX oxidase from chicory. Pestic. Biochem. Physiol., 2000, 66: 49-62
[96] Koch M, Breithaupt C, Kiefersauer R, et al. Crystal structure of protoporphyrinogen IX oxidase: a key enzyme in haem and chlorophyll biosynthesis. The EMBO Journal, 2004,23: 1720-1728
[97] Suzuki S, Watanabe H, Jikihara T, et al. Structure-activity relationship of cyclic imide herbicides. In: Kataoka T, eds. Proceedings of the 5~(th) Asian Pacific Weed Science Society Conference. Tokyo: Asian Pacific Weed Society, 1976. 176-182
[98] Fadayomi O, Warren G F. The light requirement for herbicidal activity of diphenyl ethers. Weed Sci., 1976, 24: 598-600
[99] Matsunaka S. Acceptor of light energy in photoactivation of diphenyl ether herbicides. J. Agric. Food Chem., 1969, 17: 171-175
[100] Kunert K J, Boger P. The bleaching effect of the diphenyl ether Oxyfluorfen. Weed Science, 1981,29(2): 169-173
[101] Orr G L, Hess F D. Mechanism of action of the diphenyl ether herbicide acifluorfen-methyl in excised cucumber (Cucumis sativus L.) Cotyledons. Plant Physiol., 1982, 69: 502-507
[102] Ensminger M P, Hess F D, Bahr J T. Nitro free radical formation of diphenyl ether herbicides is not necessary for their toxic action. Pestic. Biochem. Physiol., 1984, 163-170
[103] Jacobs M J, Jacobs N J. Oxidation of protoporphyrinogen to protoporphyrin, a step in chlorophyll and heme biosynthesis. Biochem. J., 1987, 244: 219-224
[104] Haworth P, Hess F D. The generation of single oxygen (~1O_2) by the nitrodiphenyl ether herbicide Oxyfluorfen is independent of photosynthesis. Plant Physiol., 1988, 86: 672-676
[105] Matringe M, Scalla R. Studies on the mode of action of acifluorfen-methyl in nonchlorophyllous soybean cells. Plant Physiol., 1988, 86: 619-622
[106] Witkowski D A, Hailing B P. Accumulation of photodynamic tetrapyrroles induced by acifluorfen-methyl. Plant Physiol., 1988, 87: 632-637
[107] Lydon J, Duke S O. Porphyrin sythesis is require for photobleaching activity of the p -nitrosubstituted diphenyl ether herbicides. Pestic. Biochem. Physiol., 1988,74-83
[108] Bowyer J R, Hallahan B J, Camilleri P, et al. Mode of action studies on nitrodiphenyl ether herbicides. Plant Physiol., 1989, 89: 674-680
[109] Witkowski D A, Hailing B P. Inhibition of plant protoporphyrinogen oxidase by the herbicide acifluorfen-methyl. Plant Physiol., 1989, 90: 1239-1242
[110] Matringe M, Camadro J M, Labbe P, et al. Protoporphtrinogen oxidase as a molecular target for diphenyl ether herbicides. Biochem. J., 1989,260: 231-235
[111] Becerril J, Duke S O. Protoporphyrin IX content with activity of photobleaching herbicides. Plant Physiol., 1989,90: 1175-1181
[112] Nicolaus B, Sandmann G, Watanabe H, et al. Herbicide-induced peroxidation: influence of light and Diuron on protoporphyrin IX formation. Pestic. Biochem. Physiol., 1989,35:192-201
[113] Matringe M, Scalla R, Effects of Acifluorfen-methyl on cucumber cotyledons: porphyrin accumulation. Pestic. Biochem. Physiol., 1988,164-172
[114] Duke S O, Becerril M J, Sherman T D, et al. The role of protoporphyrin IX in the mechanism of action of diphenyl ether herbicides. Pestic. Sci., 1990, 30: 367-378
[115] Warabi E, Usui K, Tanaka Y, et al. Resistance of a soybean cell line to oxyfluorfen by overproduction of mitochondrial protoporphyrinogen oxidase. Pest Manag. Sci., 2001, 57(8): 743-748
[116] Murata S, Kimura Y, Mabuchi T, et al. Resistance of a soybean cell line to oxyfluorfen by overproduction of mitochondrial pro Pyraflufen-ethyl: A potent protox inhibiting herbicide (Part 3): Accumulation of protoporphyrinogen IX prior to protoporphyrin IX in intact plants treated with protoporphyrinogen IX oxidase-inhibiting herbicides. Pesticide Sci., 2004, 29(3), 195-199
[117] Lehnen L P, Sherman T D, Becerril J M, et al. Resistance of a soybean cell line to oxyfluorfen by overproduction of mitochondrial pro Issue and cellular localization of Acifluorfen-induced porphyrins in cucumber cotyledons. Pestic. Biochem. Physiol., 1990,239-248
[118] Mito N, Sato R, Miyakado M, et al. In Vitro mode of action of N-phenylimide photobleaching herbicides. Pestic. Biochem. Physiol., 1991,40: 128-135
[119] Camadro J M, Matringe M, Scalla R, et al. Kinetic studies on protoporphyrinogen oxidase inhibition by diphenyl ether herbicides. Biochem., 1991, 277:17-21
[120] Jacobs J, Jacobs N J, Sherman T D, et al. Effect of Diphenyl Ether Herbicides on oxidation of protoporphyrinogen to protoporphyrin in organellar and plasma membrane enriched fractions of barley. Plant Physiol., 1991, 97: 197-203
[121] Jacobs J M, acobs N J. Prophyrin accumulation and export by isolated barley (Hordeum vulgare) plastids. Plant Physiol., 1993,101: 1181-1187
[122] Lee H J, Duke S O. Protoporphyrinogen IX-oxidase activites involved in the mode of action of peroxidizing herbicides. J. Agric. Food Chem., 1994,42: 2610-2618
[123] Yamato S, Masanao K, Ohkawa H. Purification and characterization of a protoporphyrigen-oxidizing enzyme with peroxidase activity and light-dependent herbicide resistance in tobacco cultured cells. Pestic. Biochem. Physiol., 1994,50: 72-82
[124] Retzlaff K, Boger P. An endoplasmic reticulum plant enzyme has protoporphyrinogen IX oxidase activity. Pestic. Biochem. Physiol., 1996, 54: 105-114
[125] Ohki A, Ohki S, Koizumi K, et al. Phytotoxicity caused by peroxidizing herbicides is alleviated by 2-substituted 4,6-bis(ethylamino)-1,3,5-triazines. J. Pesticide Sci., 1997,22:309-313
[126] Dayan F E, Duke S O, Weete J D, et al. Selectivity and mode of action of carfentrazone-ethyl, a novel phenyl triazolinone herbicide. Pestic. Sci., 1997, 51: 65-73
[127] Camadro J M, Arnould S, Guen L L, et al. Characteristics of protoporphyrinogen oxidase.In:Boger P,Wakabayashi K,eds.Peroxidizing Herbicides.Berlin:Springer,1999.245-255
[128]Nandihalli U B,Duke M V,Duke S O.Quantitative structure-activityrelationship of protoporphyrinogen oxidase-inhibiting diphenyl ether herbicides.Pestic.Biochem.Physiol.,1992,43:193-211
[129]Nandihalli U B,Duke M V,Ashmore J W,et al.Enantioselectivity of protoporphyrinogen oxidase-inhibiting herbicides.Pestic.Sci.,1994,40:265-277
[130]Theodoridis G,Poss K M,Hotzman F W.Herbicidal 1-(2,4-dihalo-5- phenoxy-phenyl)-4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4triazolin-5(1H)one derivatives:synthesis and structure- activity relationships.In:Synthesis and chemistry of agrochemicals Ⅳ,ACS symposium series 584.ACS,1995.78-89
[131]Uraguchi R,Sato Y,Nakayama A,et al.Molecular shape similarity of cyclic imides and protoporphyrinogen Ⅸ.Pesticide Sci.,1997,22:314-320
[132]Sato Y,Nakayama A,Sukekawa M,et al.Molecular shape similarity between cyclic imides and protoporphyrinogen Ⅸ.Pestic.Sci.,1999,55:343-389
[133]曹程.靶标为原卟啉原氧化酶的高效除草剂品种.农药科学与管理,1997,4:25-29
[134]黄明智.环状亚胺类除草剂的研究进展.中国化工学会农药专业委员会第九届年会论文集.沈阳:中国化工学会农药专业委员会,1998.16-22
[135]石小清,沈晓霞,王阿国,等.原卟啉原氧化酶抑制剂研究与开发进展.浙江化工,2000,3 1(3):33-35
[136]张国生.原卟啉原氧化酶抑制剂类除草剂进展概况.农药科学与管理,2001,22(6):121-25
[137]周宇涵,苗蔚荣,程侣柏,等.原卟啉原氧化酶抑制剂类除草剂研究进展.农药学学报,2002,4(1):1-8
[138]王建国,赵卫光,王素华,等.原卟啉原氧化酶及其抑制剂的近期研究.农药,2002,43(8):1-4
[139]刘长令.原卟啉原氧化酶抑制剂的创制经纬.农药,2003,42(1):38-40
[140]梅新娅.原卟啉原氧化酶(Protox)抑制剂研究与开发新进展.湖北化工,2003,增刊,4-5
[141]任叶果,黄明智,侯仲轲.四氢酞酰亚胺类除草剂的研究与开发进展.精细化工中间体,2004,34(6):7-9,20
[142]苏少泉.靶标原卟啉原氧化酶除草剂的发展.农药,2005,44(8):342-346
[143]陈凯,杨华铮,李永红.新型原卟啉原氧化酶抑制剂的固相合成及生物活性研究.高等学校化学学报,2001,22(10):111-115
[144]周宇涵,苗蔚荣,程侣柏,等.取代苯基吡唑类化合物的合成及其除草活性.高等学校化学学报,2003,24(7):1225-1230
[145]周宇涵,苗蔚荣,程侣柏,等.N-芳基唑烷酮类化合物的合成及其除草活性.农药学学报,2001,3(3):71-73
[146]李斌,徐基东,满瀛,等.具有除草活性的2-(硫代)-4,5-咪唑啉三酮类化合物.中国专利,CN 00110477.2,2001-12-12
[147]周宇涵,苗蔚荣.四取代苯基噁唑烷酮类除草剂.中国专利,CN 00126117.7,2001-01-24
[148]李彦龙,王俊春.取代苯基噁唑烷酮类除草剂.中国专利,CN 01117477.3,2001-12-26
[149]周宇涵,苗蔚荣.取代苯基五元氮杂环类除草剂.中国专利,CN 02143654.1,2003-03-19
[150]洪露,王风云,倪珏萍,等.一种取代苯基杂环类化合物除草剂.中国专利,CN 00112213.4,2000-10-04
[151]刘长令,张宗俭,刘晓楠,等.取代三唑、咪唑、吡唑类除草剂.中国专利,CN 00110501.9,2001-12-26
[152]李斌,徐基东,徐龙鹤,等.苯甲酸基不饱和羧酸酯类除草剂.中国专利,CN 00110478.0,2001-12-12
[153]李斌,徐基东.具有除草活性的3-(2-氟-4,5,6-取代苯基)-1,3-喹唑啉-2,4-二酮类化合物.中国专利,CN 00123348.3,2002-06-26
[154]李斌,徐基东.具有除草活性的3-(2-氟-4,5,6-取代苯基)-1,3-苯并嘧啶-4-酮类化合物.中国专利,CN 00123349.1,2002-06-26
[155]徐基东,李斌.具有除草活性的3-取代苯基-1,2,3-苯并三嗪-4-酮类化合物.中国专利,CN 00123023.9,2002-04-24
[156]侯仲轲,任叶果,黄明智,等.一种具有生物活性的杂环取代苯并噁嗪环类化合物.CN 03118226.7,2003-09-17
[157]陈凯.基于药效团模型的新型靶酶抑制剂的设计、合成、生物活性及膦酰基烯酮硫代缩醛的反应研究:[博士学位论文].天津:南开大学,2001
[158]李爱秀,王瑾玲,缪方明.原卟啉原氧化酶抑制剂的三维药效团研究.计算机与应用化学,2002,19(3):335-338
[159]李爱秀,王瑾玲,缪方明.距离比较法(DISCO)构建原卟啉原氧化酶抑制剂药效团模型.化学学报,1999,57:1226-1232
[160]高爽,叶非.靶标酶在除草剂研究与开发中的应用.农药科学与管理,2005,26(1):25-29
[161] Dayan F E, Duke S O. Overview of protoporphyrinogen oxidase-inhibiting herbicides. In: Proceeding of Brighton Crop Prot. Conf.—Weeds. Surrey: British Crop Protection Council, 1997, 83-92
[162] Duke S O, Dayan F E, Yamamoto M, et al. Protoprophyrinogen oxidase inhibitors—their current and future roles. In: Proceeding of second international Weed Control Congress. Copenhagen, 1996. 775-780
[163] Nagano E. Herbicidal efficacy of protoporphyinogen oxidase inhibitors. In: Boger P, Wakabayashi K, eds. Peroxidizing Herbicides. Berlin: Springer, 1999. 293-302
[164] Nandihalli U B, Duke S O. Structure-activity relationship of protoporphyrinogen oxidase inhibiting herbicides. ACS Symp. Ser. 559 (Prophyric Pesticides), 1994, 133-146
[165] Hayashi Y, Furusaki A, Tagashira M. Crystal structure and postemergent herbicidal activity of geometrical isomers of methyl [[[1-[5-[2-chloro-4-(trifluoro- methyl) phenoxy]- 2-nitrophenyl]-2-methoxy-ethylidene]amino]oxy]acetate. J. Agric. Food Chem., 1991,38:2086-2089
[166] Lyga J W, Chang J H, Theodoridis G. Structural replacements for the benzoxa- zinone protox inhibitors. Pesticide Sci., 1999, 55: 281-287
[167] Wakabayashi K. Molecular design of cyclicimide herbicides using biorational approaches. Pesticide Sci., 1988,13: 337-361
[168] Lyga J W, Patera R M, Theodoridis G, et al. Synthesis and quantitative structure- activity relationships of herbicidal N-(2-Fluoro-5- methoxyphenyl)-3,4,5,6-tetra- hydrophthalimides. J. Agric. Food Chem., 1991, 39: 1667-1673
[169] Ishida S, Hirai K, Kohno H, et al. Protoporphyrinogen-IX oxidase inhibition by N- (2,4,5-trisubstituted phenyl)-3,4,5,6- tetrahydrophthalimides. Pesticide Sci., 1997, 22: 299-302
[170] Ishida S, Iida T, Kohno H., et al. Comparison of phytotoxicities between 4-fluo- rinated and non-fluorinated 2-chloro-5-(3,4,5,6-tetrahy- drophthalimido)benzoates. Pesticide Sci., 1999,24: 28-32
[171] Iida T, Uchida A, Uraguchi R, et al. Peroxidizing phytotoxicities of 1,2-dialkyl- 1,2,4-triazolidines and 3,4-dialkyl-1,3,4-thiadiazolidines. Pesticide Sci., 1997, 22: 303-308
[172] Chang J H, Lyga J W. Preparation of tetrazolinone herbicides. US 4734124, 1988-03-29
[173] Hirai K, Yano T, Matsukawa T, et al. Synthesis and herbicidal activity of new oxazolidinedione derivatives. Pesticide Sci., 1999,24: 156-169
[174]Hiraki M,Ohki S,Sato Y,et al.Protoporphyrinogen-Ⅸ oxidase inhibitors:Bioactivation of thiadiazolidines.Pestic.Biochem.Physiol.,2001,70:159-167
[175]Miyamoto Y,Ikeda Y,Wakabayashi K.Synthesis and phytotoxic activities of N-substituted phenyl isothiazolone derivatives.Pesticide Sci.,2003,28:293-300
[176]Meazza G,Bettarini F,Porta P L,et al.Synthesis and herbicidal activity of novel heterocyclic protoporphyrinogen oxidase inhibitors.Pest.Manag.Sci.,2004,60:1178-1188
[177]Nagano H,Haga T,Sato M,et al.Tetrahydrophthalimides and their herbicidal use.US 4640707,1987-02-03
[178]Ohta H,Suzuki S,Watanabe H.N-(p-chlorophenyl)-3,4,5,6-tetrahydrophthalimide.Agr.Biol.Chem.1976,40(4),745-751.
[179]Ohta H,Jikihara T,Wakabayashi K.Quantative structure-active study of herbicidal N-aryl 3,4,5,6 tetrahydrophthalimides and related cyclic imides.Pestic.Biochem.Physiol.1980,14,153-160.
[180]Kwon J W,Armbrust K L,Grey T L.Hydrolysis and photolysis of flumioxazin in aqueous buffer solutions.Pest.Manag.Sci.,2004,60:93-43
[181]Wong J L,Fuchs D S.Reactivities and electronic aspects of diazomethane methylation of uracil and its methyl derivatives.J.Org.Chem.1971,36,848-850.
[182]Gambacorta A,Farah M E,Tofani D.HSAB drive chemoselectivity in alkylation of uracil derivatives.Tetrahedron 1999,55,12615-12628.
[183]杨瑞娜,孙雨安,邝爱燕,等.四氢酞酰环状亚胺类除草剂的开发进展.农药,2001,40(10):7-9,11
[184]Duke S O,Lydon J,Becerril J M,et al.Protoporphyrinogen oxidase-inhibiting herbicides.Weed Science,1991,39:465-473
[185]Haga T,Nagano E,Sato R,et al.Tetrahydrophthalimide derivatives,their production and use.EP 0322401,1989-06-28
[186]Stetter J,Santel H,Schmidt R,et al.N-arylpyrroline-2,5-diones.EP 0288789,1988-11-02
[187]Nagano E,Hashimoto S,Yoshida R,et al.Tetrahydrophthalimide compounds,and their production and use.EP 0083055,1983-07-06
[188]George Y S,Essam D F.Synthesis and properties of somw new N,N-disubstituted thiorueas of biological interest.J.Heterocycl.Chem.1985,22(1),137-140.
[189]茹呈杰,龚富生.酰基硫脲化合物的合成及其生理活性.应用化学,1994,11(3),92-95.
[190]郭佃顺,黄汝骐,高蓉华.N-取代三氯乙酰胺合成新脲类化合物及其生物活性 的研究(Ⅰ).高等学校化学学报,1996,17(2),255-257.
[191]郭佃顺,黄汝骐,高蓉华.N-取代三氯乙酰胺合成N,N-多亚甲基双(N-(4-氯苯基)脲.合成化学,1996,4(1),91-92.
[192]杨华铮.农药分子设计.北京:科学出版社,2003.125-144
[193]刘长令.世界农药大全-除草剂卷.北京:化学工业出版社,2002.387
[194]Eckert H,Forster B.Triphosgen,a crystalline phosgene substitute.Angew.Chem.Int.Ed.Engl.,1987,26:894-895
[195]Organic chemical for research and development 2003-2004.Germany:ABCR GmbH & Co.KG,2003.345,1244
[196]李润卿,范国梁,渠荣遴.有机结构波谱分析.天津大学出版社,天津,2002:203.
[197]邓胜娄,陈茹玉,杨秀凤.1,3-双芳氧乙酰基-1,3,2-二氮磷杂环戊烷-2-硫(硒)化代合物的合成及除草活性研究.高等学校化学学报,2001,22(11),1833-1837.
[198]贺红武,汪军,刘钊杰.具有生物活性的有机磷化合物的研究-[(取代)芳氧基乙酰氧基]烷基膦酸.应用化学,1994,11(4),21-24.
[199]殷树梅.植物生长调节剂P-703的合成.山东化工,1988,(1),28.
[200]袁德茂.芳氧基乙酸的合成.农药,1988,27(6),13.
[201]卿凤翎.芳氧基乙酸的三相催化合成.化学试剂,1989,11(4),250.
[202]李英俊,付兴吉.超声波辐射固-液相芳氧(硫)基羧酸的合成.应用化学,1993,10(6),97-98.
[203]唐除痴,李煜昶,陈彬.农药化学.天津:南开大学出版社,1998:L522-530.
[204]李超,覃章兰,李秀文,等.4-甲基-苯磺酸-2-氧-2-[3-(5-芳基-[1,3,4]噁二唑-2-基)-硫脲]-乙基酯的合成及生物活性研究.有机化学,2005,25(5),587-590.
[205]杨新玲,张钟宁.一类新型酰基脲化合物的设计合成及生物活性.高等学校化学学报,1997,18(3),395-398.
[206]柏再苏,王大翔.新杂环农药的研究发展及合成方法.北京:化学工业出版社,2004:363.
[207]张一宾.世界酰胺类除草剂发展概述.农化新世纪,2006,(5):23
[208]Sawada Y,Yanai T,Nakagawa H,et al.Synthesis and insectididal activity of benzoheterocyclic analogues of N-benzoyl-N-(tert-butyl)benzohydrazide.Pest.manage.Sci.2003,59,25.
[209]Michlotti E L,Young D H.Heterocyclic N-acetonylbenzamides and their use as fungicides.EP 1 229037,2002-08-07
[210]Agrade A,Singh R,Li H,et ai.2,4-Pyrimidineamine compounds.WO 0513996,2004-05-18
[211]Katayama T,Kawamura S,Sanemitsu Y,et al.Pyridazin-3-one derivatives,their use,and intermediates for their production.WO 9707104,1997-02-27
[212]Hoelscher P,Rehwinkel H,Jaroch S.Benzoxazine and benzothiazine derivatives and hteir use in pharmaceuticals.WO 9912915,1999-03-18
[213]Schallner O,Schwarz H G.,Hoischen D,et al.Substituted benzo-nitro-heterocycles and use thereof as herbicides.WO 0206277,2002-01-24
[214]黄春艳,陈铁保,王宇,等.丙炔氟草胺土壤处理防除春玉米田杂草效果初报.中国农学通报,2001,17(6),88-90.
[215]黄春艳,陈铁保,王宇,等.丙炔氟草胺茎叶处理防除春玉米田阔叶杂草效果评价.杂草科学,2001,2:25-26.
[216]杨剑波,庞怀林,黄超群.氟咯草酮的合成研究.精细化工中间体,2005,35(4):24-27.
[217]Hayes N V,Brabch G K.The acidic dissociation constants of phenoxyacetic acid and its derivatives.J.Amer.Chem.Soc.,1943,65:1555-1564
[218]Haga T,Nagano H,Sato M,et al.Benzoxazine derivatives.JP 61140570,1986-06-27
[219]Haga T,Nagano H,Sato M,et al.Nitrobenzoxazine derivatives.JP 61140571,1986-06-27
[220]Haga T,Nagano H,Sato M,et al.4-Substituted nitrobenzoxazine derivatives.JP 61140572,1986-06-27
[221]Haga T,Nagano H,Sato M,et al.Aminobenzoxazine derivatives.JP 61140573,1986-06-27
[222]Hsu A C.Benzoxazolone compounds and the use thereof as microbicides.US 5102898,1992-04-07
[223]阳海,庞怀林,等.催化加氢合成6-氨基-7-氟-4-取代-2H-苯并[6][1,4]噁嗪-3(4H)-酮.精细化工,2006,23(11):1142-1144
[224]黄引,庞怀林,等.雷尼镍催化加氢合成7-氟-4-取代-2H-苯并[6][1,4]噁嗪-3(4H)-酮.精细化工中间体,2006,36(4):28-29
[225]庞怀林,阳海,尹笃林,等.N-(取代)-6-(3-氯-4-氯甲基-2-氧吡咯烷-1-基)-7-氟-3,4-二氢-2H-[1,4]苯并噁嗪-3-酮衍生物的合成与生物活性研究.有机化学,2007,27(9):1130-1136
[226]Miriam B,Luca Forti,Franco G,et al.Halogen atom transfer radical cyclization of N-allyl-N-benzyl-2,2-dihaloamides to 2-pyrrolidinoes,pomoted by Fe~0-FeCl_3 or CuCl-TMEDA.Tetrahadron,1997,53(41):14031-14042.
[227]Franco G,Franco B,Luca F,et al.The influence of benzylic protection and allylic substituents on the CuCl-TMEDA catalyzed rearrangement of N-Allyl-N-Benzyl -2,2-Dihaloamides to γ-Lactams.Application to the stereoselective synthesis of Pilotactam.Tetrahadron,1999,55:5839-5852.
[228]Hughes D,Peace J E.Preparation ofpyrazolecarboxamides as novel insecticides.WO 200585234,2005-7-15
[229]李斌,白丽萍,等.1-[7-氟-4-炔丙基-1,4-苯并噁嗪-3-酮-6-基]-3-正丙基-2-硫代咪唑啉三酮的合成及其除草活性.现代农药,2005,4(3):19-20
[230]Xu,Shangcheng;Wan,Qin;et al.Synthesis and insecticidal activity of 2-(p-chloroph- enyl)pyrrole-3-carbonitriles.南京农业大学学报,2004,27(4):110-113
[231]Aylvie M,Muriel R.,et al.The possible role of hydroxylation in the detoxification of atrazine in the detoxification ofatrazine in mature vetiver(Chrysopogon zizanioides Nash)grown in hydroponics.Journal of Biosciences,2005,60(5/6):427-434
[232]Ho Sik,K.;Seong Uk,L..Synthesis ofpyrazolyl-1,4-benzoxazine derivatives.Journal of the korean Chemical Society,2004,48(4):451-455
[233]Katsutoshi F,Yasushi N,et al.Preparation of haloalkenes and their use as pesticides.JP 200636706,2006-02-09
[234]Peter H,Hartmut R.Benzoxazine and benzothiazine derivatives and their use as nitric oxide synthase inhibitors.WO9912915,1999-03-18
[235]Yoshihiro K,Hidetatsu I,et al.Preparation of condensed pyrimidinone derivatives as herbicides.JP 2000247975,2000-09-12
[236]Huang M Z,Huang K L.Synthesis and herbicidal activity of 2-(7-fluoro-3-oxo-3,4-dihydro-2H-benzo[b][1,4]orazin-6-yl)isoindoline-1,3-diones.J.Agric.Food Chem.2005,53:7908-7914.
[237]刘长令.对羟基苯基丙酮酸酯双氧化酶抑制剂的研究进展.农药.1999,38(2):5-9.
[238]苏少泉.HPPD-开发除草剂品种的新靶标.农药.2000,39(5):4-7.
[239]叶贵标.除草剂作用机理分类法及其应用.农药科学与管理.1999,20(1):32-35.
[240]吴彦超,胡方中,杨华铮.HPPD抑制剂的研究进展.农药学学报.2001,3(3):1-10.
[241]杨丽,张荣全,叶非.对羟苯基丙酮酸双氧化酶抑制剂的研究进展.现代农药.2003,2(5):1-4.
[242]Jayasree V,Rong A,et al.Preparation of benzopyran and related analogs for treating retinoid responsive disorders using selective inhibitors of CYP26A and CYP26B.WO 200558301,2005-5-8
[243]Christoph L,Andrew E,et al.Preparation of substituted pyridines as herbicides.WO 200558831,2005-06-30
[244]Yuji N,Makiko S.Preparation oftriketone compounds,2-benzoylcyclohexane-1,3-diones and enol esters thereof as herbicides.WO 2005118530,2005-12-15
[245]Andreas V A,Lothar W,et al.Preparation of benzoylcyclohexanedionen derivative herbicides.US 2005282710,2005-12-22
[246]Sebastlan,W.;Renaud,B.;et al.Preparation of(3-alkoxypropyl)pyridinyl ketones with herbicidal activities.WO 200666871,2006-06-27
[247]张永华.对氯苯甲酸的合成.天津大学学报,2001,34(3):389-391.
[248]李祥龙,庞怀林,杨剑波.2-硝基-4-甲砜基苯甲酸的合成方法.精细化工间体,2004,34(6):18-20.
[249]Brown S M.Process for the preparation of acylated cyclic 1,3-dicarbonyl compounds.GB9803458,1990-06-10.
[250]SMART 5.0 and SAINT 4.0 for Windows NT:Area Detector Control and Integration Software.Madison:Bruker Analytical X-ray Systems,Inc.1998
[251]Sheldrick G M.SHELXTL:Structure Determination Software Programs.Madison:Bruker Analytical X-ray System,Inc.1997
[252]邓立刚,徐炳祥,姚斌.碘代炔丙基氧羟基丙氨酸甲酯合成方法的改进.化学世界,1997,38(11):589-590.
[253]Utsunomiya A,Nakamura M,Kuwatsuka T,et al.Process for the preparation of iodo alkynyl earbamates.US 5183927.1993-02-02.
[254]Punjia N,Fungicidal compounds,compositions and processes.US 4325966.1982-04-20.
[255]Nagano,E.;Haga,T.;Sato,R.;et al.Tetrabydrophtalimides,and their production and use.EP 170 191.1986-02-05.
[256]吴兆民,刘华俊,陈红艳,等.一氯化碘的乙酸溶液制法改进.化学试剂,2002,24(1):33-34.
[257]陈红艳,吴兆民.一氯化碘乙酸溶注解对芳香化合物碘化的研究.山西师范大学学报(自然科学版),2003,17(3):43-47.
[2]傅向升.农药大国的喜与优.农化市场十日迅,2007,(7):12-14
[3]谷业理,黄存达.农田杂草化学防治.北京:科学普及出版社,1998:1-5
[4]农田杂草的防治.http://www.agrionline.net.cn/new_agri/list.asp?id=2644
[5]张朝贤.我国农田杂草治理的差距与亟待解决的问题.http://zbxh.jaas.ac.cn/2005/5-12/143940.html
[6]除草剂.http://baike.baidu.com/view/48545.htm
[7]臧开保,王晓光.农药的研究与趋势.湖南化工,2000,30(3):1-8
[8]苏少泉.除草剂作用靶标与新品种创制.北京:化学工业出版社,2001.1
[9]魏福香.除草剂的现状与发展趋势.安徽农业,1999,(3):8-9
[10]胡笑形.2009年全球作物保护市场预测与中国农药的机遇.中国农药,2005,(3):11-23
[11]毕璋友,洪流.中国农药工业的现状及发展趋势.安徽农业科学,2005,33(8):1497-1450
[12]王律先.2006年全国农药生产回顾及2007年展望.中国农药,2007,(2):43-51
[13]梁丽娜,郭平毅,李奇峰.中国除草剂产业现状-面临的问题及发展趋势.中国农学通报,21(10):321-323
[14]黄明智.异吲哚-1,3-二酮衍生物的合成、生物活性及构效关系研究.[博士学位论文],长沙,中南大学,2006
[15]欧晓明,唐德秀.除草剂作用原理研究的新进展.世界农业,2000,(10):28-30
[16]苏少泉.除草剂作用靶标的分类与使用.农药,1998,37(11):1-7
[17]Evans,D A.New era,new challenges,new solutions.In:Proceedings of Brighton Crop Proteetion Conference-Pests & Diseases.Brighton:BCPC,2000:3-18
[18]刘长令.除草剂研究开发的新进展和发展趋势.江苏化工,2000,28(8):15-20
[19]苏少泉.除草剂开发面临的问题与发展趋势.现代化农业,2002,(1):5-8
[20]胡笑形.全球农药公司继续兼并重组.国际化工信息,2002,(8),22-24
[21]张培.农药企业将迎来整合新挑战.农药,2006,45(6),409
[22]陈文斌,金桂玉.含稠杂环新农药的研究进展.农药学学报,2000,2(4):1-10
[23]侯仲轲.具有生物活性的新颖杂环化合物.新农药,2002,(2):25-28
[24]钱旭红,徐晓勇,宋恭华,等.二十一世纪新农药研发趋势.贵州大学学报(自然科学版),2003,20(1),83-90
[25]张一宾,钱跃言.含氟农药的结构、特性及研究开发概况.江苏化工,2002,30(3):5-10,47
[26]王宁,薛振祥.当今热点农药的含氟中间体开发.现代农药,2004,3(5):1-7,45
[27]梁诚.含氟农药的研究开发与生产应用(上).新农药,2005,(2):19-24
[28]梁诚.含氟农药的研究开发与生产应用(下).新农药,2005,(3):7-12
[29]车超,覃兆海.手性农药合成研究进展.化学通报,2002,65:w042
[30]谭效松,贺红武.除草剂的作用靶标与作用模式.农药,2005,44(12):533-541
[31]Ward E,Bernasconi P.Target-based discovery of crop protection chemicals.Nat Biotechnol,1999,(17):618-619
[32]Wolfgang L,Fmderik B,Andreas R,et al.Target-based discovery of novel herbicide.Curt Opin Plant Biol,2004,(7):219-225
[33]王涛,贺红武,袁均林.丙酮酸脱氢酶系:除草剂品种的新靶标.应用化学,2003,20(7):613-617
[34]李茹,赵桂东,熊战之,等.浅议化学农药.现代农业科技--种子与种苗篇,2005,(9):51-52
[35]聂开晟,范志金,刘长令.三酮类除草剂的研究新进展.农药,2006,45(1):4-7
[36]马娟,董全皋.微生物除草剂与生物安全.山东农药信息,2006,(5):21-23
[37]苏少泉,滕春红,赵世君.最近15年世界转基因抗除草剂作物.农药研究与应用,2006,(3):1-4
[38]马俊,王金艳,李刚.转基因作物的生物安全及安全管理的几点思考.杂粮发作物,2007,27(3):248-249
[39]沈孝宙.转基因食物争论的焦点.百科知识,2007,(6):9-11
[40]李海屏.20世纪80年代以来世界除草剂新品种开发进展及特点(续).农药科学与管理,2005,25(5):26-29
[41]Hirai K.Structural evolution and synthesisi of diphenyl ethers,yclic imides and related compounds.In:Boger P,Wakabayashi K,eds.Peroxidizing Herbicides.Berlin:Springer,1999.15-72
[42]Iwataki I.Recent advances in peroxidizing herbicides(patent overview).In:Boger P,Wakabayashi K,eds.Peroxidizing Herbicides.Berlin:Springer,1999.73-90
[43]Scherman T D,Duke M V,Clark R D,et al.Pyrazole phenyl ether herbicides inhibit protoporphyrinogen oxidase.Pestic.Biochem.Physiol.,1991,40(3):236-245
[44]Nagano E,Hashimoto S.Tetrahydrophthalimides,and their production and use.EP 0061741,1987-10-06
[45]Hirai K,Futikami T.Oxazolidinedione derivatives,process for their preparation,and herbicides containing the same.WO 8702357,1987-04-23
[46]Jean M,Roger B.5-t-Butyl-3-phenyl-2-oxadiazolones.US 3385862,1968-05-28
[47]Nagano E.2-Phenyl-4,5,6,7-tetrahydro-2h-indazole derivative,its preparation,and herbicide comprising it as active ingredient.JP 60252465,1985-12-13
[48]Miura Y.3-Substituted phenylpyrazole derivative or its salt and herbicide.JP 372460,1991-03-27
[49]Dutra G A,Hamper B C.Herbicidal substituted aryl-haloalkyl pyrazoles.WO 9206962,1992-04-30
[50]Yamagich M,Watase Y.Thiadiazabicyclononane derivatives and herbicidal compositions.EP 0273417,1988-07-06
[51]Theodoridis G.Herbicidal aryl triazolinones.US 4818275,1989-04-04
[52]Poss K M.Herbicidal triazolinones.WO 9002120,1990-03-08
[53]Ganzer M,Franke W.Heteroeyclic substituted azoles and azines,process for their preparation and their use as an agent with herbicide activity.EP 0311135,1989-04-12
[54]Loux H M.Method for the control of undesirable vegetation.US 3235361,1966-02-15
[55]Soboczenski E J.3,5-Disubstitued uraeils.US 3352863,1967-11-14
[56]Loux H M.3-Bicycloalkyl-6-methyluracil.US 3360522,1967-12-26
[57]Komori T,Sanemitsu Y.Uracil compounds and use thereof.US 6403534,2002-6-13
[58]刘长令.世界农药大全(除草剂卷).化学工业出版社,北京,2002,146-147.
[59]刘长令.噁二嗪类杀虫剂的创制经纬.农药,2002,41(10),47-48.
[60]Sting A R,Siegrist U E,Baumeister P E.Preparation of 3-aryl-uracil derivative useful as herbicide.DE 19741411,1998-03-26
[61]Andree R,Drewes M W.Dollinger,M.Heterocyelyluracils.US 6184183,2001-02-06
[62]Andree R,Drewes M W,Haas W.Heterocyclyluracils.US 6187716,2001
[63]Andree R,Drewes M W,Dollinger,M.Substituted phenyl uracils.US 6432879,2002-08-12.
[64]Nishio S.Herbicide composition.EP 1459628,2004-09-22
[65]Theodoridis G.Herbieical 2-[(4-heterocyclic-phenoxymethyl)phenoxy]-alkanoates.US 5262390,1993-11-16
[66]Theodoridis G.,Crawford S D.Herbicidal isoindolinonyl-and 3,4-dihydroisoquinolo-nyl substituted heterocycles.US 6277847,2001-08-21
[67]Reinhard R,Hamprecht G,Zagar C.3-[Benz(ox/thi)azol-7-yl]-1H-pyrimidine-2,4-diones.WO 0028822,2000-05-25
[68]Suchy M,Winternitz P,Zeller M.Heterocyclic substituted uracil derivatives.US 5232898,1993-08-03
[69]Klintz R G.,Schaefer P.3-Aryluracils and intermediates for their preparation.WO 9628442,1996-09-19
[70]Crawford S D.Cycloimido-substituted benzofused heterocyclic herbicides.WO 9838188,1998-09-03
[71]Takano M,Kawamura S,Komori T.Condensed heterocylic compounds and herbicides containing them.US 6586368,2003-07-01
[72]Marvin J K,Harvey R W.Method for the preparation of benzyluracils.US 5817814,1998-10-06
[73]Menke,O.;Hamprecht,G.;Menges,M.1-Amino-3-benzyl uracils.WO 9842682,1998-10-01
[74]Konz M J,Wendt H R.Improved method for the preparation of benzyluracils.WO 9850369,1998-11-12
[75]Sanemitsu Y,Tohyama Y.Uracil herbicides.WO 0021936,2000-04-20
[76]Puttner R,Bohner J.Herbicidal 3-arylamino-6-trifluoromethyluracils.US 5919732,1999-07-06
[77]Menke O,Gotz R,Rack M.New 3-aryl-methyl-uracil derivatives.DE 19738084,1999-03-04
[78]Andree R,Drewes M W.Substituted arylalkyluracils.WO 9840362,1998-09-17
[79]Menke O,Klintz R,Hamprecht G.1-Amino-3-benzyluracils.US 6268311,2001-07-31
[80]刘长令.世界农药大全(除草剂卷).北京,化工工业出版社,2002,3-6.
[81]杨道武,谌伟民,等.2H-[1,4]苯并噁嗪类化合物合成研究进展.精细化工中间体,2005,35(6):7-10
[82]Virtanen A I,Hietala P K.The structures of the precursors of benzoxazolinone in rye plants.Ⅱ.Suom.Kemistil.B.1959,32B,252
[83]Hamilton R H,Bandurski R S.Isolation and characterization of a cyclic hydroxamate from Zea mays.Cereal Chem.1962,39:107-113
[84]Argandona V H,Luza J G.,Niemeyer H M.,et al.Role of hydroxamic acids in the resistance of cereals to aphids.Phytochemistry.1980,19:1665-1668
[85]Bravo H R,Lazo W.Antialgal and antifungal activity of natural hydroxamic acids and related compounds.J.Agric.Food Chem.,1996,44:1569-1571
[86]Cambier V,Hance T.Variation of DIMBOA and related compounds content in relation to the age and plant organ in maize.Phytochemistry.2000,53:223-229
[87]Macias F A,Marin D,Oliveros-Bastidas A.,et al.Structure-Activity Relationships (SAR)Studies of Benzoxazinones,Their Degradation Products and Analogues, Phytotoxicity on Standard Target Species (STS). J. Agric. Food Chem., 2005, 53: 538-548
[88] Macias F A, Chinchilla N, Varela R M., et al. Structure-Activity Relationship Studies of Benzoxazinones and Related Compounds. Phytotoxicity on Echinochloa crus-galli (L.) P. Beauv. J. Agric. Food Chem., 2005, 53: 4373-4380
[89] Larsen E, Christensen L P. Simple method for large scale isolation of the cylic Arylhydroxamic Acid DIMBOA from maize(zea maysl). J. Agric. Food Chem., 2000,48: 2556-2558
[90] Mitsuaki T, Seiji T, Masanori W. Benzoxazine Compounds Useful as Herbicides. US 5041154,1989-01-23
[91] Naoko K M, Harukazu F K., et al.. Phenoxy or Pyridyloxy-2H-1,4-Benzoxazine-3-one Derivative and Herbicide Containing Same as Active Ingredient. US 5338719,1993-04-12
[92] Poulson R, Polglase W J. The enzymic conversion of protoporphyrinogen IX to protoporphyrin IX. Protoporphyrinogen oxidase activity in mitochondrial extracts of Saccharomyces cerevisiae. J. Biol. Chem., 1975,250: 1269-1274
[93] Poulson R. The enzymic conversion of protoporphyrinogen IX to protoporphyrin IX in mammalian mitochondria. J. Biol. Chem., 1976, 251: 3730-733
[94] Camadro J M, Urban-Grimal D, Labbe P. A new assay for Protoporphyrinogen oxidase- evidence for a total deficiency in that activity in a heme-less mutant of Saccharomyces cerevisiae. Biochem. Biophys. Res. Commun., 1982,106: 724-730
[95] Adomat C, Boger P. Cloning, sequence, expression and characterization of protoporphyrinogen IX oxidase from chicory. Pestic. Biochem. Physiol., 2000, 66: 49-62
[96] Koch M, Breithaupt C, Kiefersauer R, et al. Crystal structure of protoporphyrinogen IX oxidase: a key enzyme in haem and chlorophyll biosynthesis. The EMBO Journal, 2004,23: 1720-1728
[97] Suzuki S, Watanabe H, Jikihara T, et al. Structure-activity relationship of cyclic imide herbicides. In: Kataoka T, eds. Proceedings of the 5~(th) Asian Pacific Weed Science Society Conference. Tokyo: Asian Pacific Weed Society, 1976. 176-182
[98] Fadayomi O, Warren G F. The light requirement for herbicidal activity of diphenyl ethers. Weed Sci., 1976, 24: 598-600
[99] Matsunaka S. Acceptor of light energy in photoactivation of diphenyl ether herbicides. J. Agric. Food Chem., 1969, 17: 171-175
[100] Kunert K J, Boger P. The bleaching effect of the diphenyl ether Oxyfluorfen. Weed Science, 1981,29(2): 169-173
[101] Orr G L, Hess F D. Mechanism of action of the diphenyl ether herbicide acifluorfen-methyl in excised cucumber (Cucumis sativus L.) Cotyledons. Plant Physiol., 1982, 69: 502-507
[102] Ensminger M P, Hess F D, Bahr J T. Nitro free radical formation of diphenyl ether herbicides is not necessary for their toxic action. Pestic. Biochem. Physiol., 1984, 163-170
[103] Jacobs M J, Jacobs N J. Oxidation of protoporphyrinogen to protoporphyrin, a step in chlorophyll and heme biosynthesis. Biochem. J., 1987, 244: 219-224
[104] Haworth P, Hess F D. The generation of single oxygen (~1O_2) by the nitrodiphenyl ether herbicide Oxyfluorfen is independent of photosynthesis. Plant Physiol., 1988, 86: 672-676
[105] Matringe M, Scalla R. Studies on the mode of action of acifluorfen-methyl in nonchlorophyllous soybean cells. Plant Physiol., 1988, 86: 619-622
[106] Witkowski D A, Hailing B P. Accumulation of photodynamic tetrapyrroles induced by acifluorfen-methyl. Plant Physiol., 1988, 87: 632-637
[107] Lydon J, Duke S O. Porphyrin sythesis is require for photobleaching activity of the p -nitrosubstituted diphenyl ether herbicides. Pestic. Biochem. Physiol., 1988,74-83
[108] Bowyer J R, Hallahan B J, Camilleri P, et al. Mode of action studies on nitrodiphenyl ether herbicides. Plant Physiol., 1989, 89: 674-680
[109] Witkowski D A, Hailing B P. Inhibition of plant protoporphyrinogen oxidase by the herbicide acifluorfen-methyl. Plant Physiol., 1989, 90: 1239-1242
[110] Matringe M, Camadro J M, Labbe P, et al. Protoporphtrinogen oxidase as a molecular target for diphenyl ether herbicides. Biochem. J., 1989,260: 231-235
[111] Becerril J, Duke S O. Protoporphyrin IX content with activity of photobleaching herbicides. Plant Physiol., 1989,90: 1175-1181
[112] Nicolaus B, Sandmann G, Watanabe H, et al. Herbicide-induced peroxidation: influence of light and Diuron on protoporphyrin IX formation. Pestic. Biochem. Physiol., 1989,35:192-201
[113] Matringe M, Scalla R, Effects of Acifluorfen-methyl on cucumber cotyledons: porphyrin accumulation. Pestic. Biochem. Physiol., 1988,164-172
[114] Duke S O, Becerril M J, Sherman T D, et al. The role of protoporphyrin IX in the mechanism of action of diphenyl ether herbicides. Pestic. Sci., 1990, 30: 367-378
[115] Warabi E, Usui K, Tanaka Y, et al. Resistance of a soybean cell line to oxyfluorfen by overproduction of mitochondrial protoporphyrinogen oxidase. Pest Manag. Sci., 2001, 57(8): 743-748
[116] Murata S, Kimura Y, Mabuchi T, et al. Resistance of a soybean cell line to oxyfluorfen by overproduction of mitochondrial pro Pyraflufen-ethyl: A potent protox inhibiting herbicide (Part 3): Accumulation of protoporphyrinogen IX prior to protoporphyrin IX in intact plants treated with protoporphyrinogen IX oxidase-inhibiting herbicides. Pesticide Sci., 2004, 29(3), 195-199
[117] Lehnen L P, Sherman T D, Becerril J M, et al. Resistance of a soybean cell line to oxyfluorfen by overproduction of mitochondrial pro Issue and cellular localization of Acifluorfen-induced porphyrins in cucumber cotyledons. Pestic. Biochem. Physiol., 1990,239-248
[118] Mito N, Sato R, Miyakado M, et al. In Vitro mode of action of N-phenylimide photobleaching herbicides. Pestic. Biochem. Physiol., 1991,40: 128-135
[119] Camadro J M, Matringe M, Scalla R, et al. Kinetic studies on protoporphyrinogen oxidase inhibition by diphenyl ether herbicides. Biochem., 1991, 277:17-21
[120] Jacobs J, Jacobs N J, Sherman T D, et al. Effect of Diphenyl Ether Herbicides on oxidation of protoporphyrinogen to protoporphyrin in organellar and plasma membrane enriched fractions of barley. Plant Physiol., 1991, 97: 197-203
[121] Jacobs J M, acobs N J. Prophyrin accumulation and export by isolated barley (Hordeum vulgare) plastids. Plant Physiol., 1993,101: 1181-1187
[122] Lee H J, Duke S O. Protoporphyrinogen IX-oxidase activites involved in the mode of action of peroxidizing herbicides. J. Agric. Food Chem., 1994,42: 2610-2618
[123] Yamato S, Masanao K, Ohkawa H. Purification and characterization of a protoporphyrigen-oxidizing enzyme with peroxidase activity and light-dependent herbicide resistance in tobacco cultured cells. Pestic. Biochem. Physiol., 1994,50: 72-82
[124] Retzlaff K, Boger P. An endoplasmic reticulum plant enzyme has protoporphyrinogen IX oxidase activity. Pestic. Biochem. Physiol., 1996, 54: 105-114
[125] Ohki A, Ohki S, Koizumi K, et al. Phytotoxicity caused by peroxidizing herbicides is alleviated by 2-substituted 4,6-bis(ethylamino)-1,3,5-triazines. J. Pesticide Sci., 1997,22:309-313
[126] Dayan F E, Duke S O, Weete J D, et al. Selectivity and mode of action of carfentrazone-ethyl, a novel phenyl triazolinone herbicide. Pestic. Sci., 1997, 51: 65-73
[127] Camadro J M, Arnould S, Guen L L, et al. Characteristics of protoporphyrinogen oxidase.In:Boger P,Wakabayashi K,eds.Peroxidizing Herbicides.Berlin:Springer,1999.245-255
[128]Nandihalli U B,Duke M V,Duke S O.Quantitative structure-activityrelationship of protoporphyrinogen oxidase-inhibiting diphenyl ether herbicides.Pestic.Biochem.Physiol.,1992,43:193-211
[129]Nandihalli U B,Duke M V,Ashmore J W,et al.Enantioselectivity of protoporphyrinogen oxidase-inhibiting herbicides.Pestic.Sci.,1994,40:265-277
[130]Theodoridis G,Poss K M,Hotzman F W.Herbicidal 1-(2,4-dihalo-5- phenoxy-phenyl)-4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4triazolin-5(1H)one derivatives:synthesis and structure- activity relationships.In:Synthesis and chemistry of agrochemicals Ⅳ,ACS symposium series 584.ACS,1995.78-89
[131]Uraguchi R,Sato Y,Nakayama A,et al.Molecular shape similarity of cyclic imides and protoporphyrinogen Ⅸ.Pesticide Sci.,1997,22:314-320
[132]Sato Y,Nakayama A,Sukekawa M,et al.Molecular shape similarity between cyclic imides and protoporphyrinogen Ⅸ.Pestic.Sci.,1999,55:343-389
[133]曹程.靶标为原卟啉原氧化酶的高效除草剂品种.农药科学与管理,1997,4:25-29
[134]黄明智.环状亚胺类除草剂的研究进展.中国化工学会农药专业委员会第九届年会论文集.沈阳:中国化工学会农药专业委员会,1998.16-22
[135]石小清,沈晓霞,王阿国,等.原卟啉原氧化酶抑制剂研究与开发进展.浙江化工,2000,3 1(3):33-35
[136]张国生.原卟啉原氧化酶抑制剂类除草剂进展概况.农药科学与管理,2001,22(6):121-25
[137]周宇涵,苗蔚荣,程侣柏,等.原卟啉原氧化酶抑制剂类除草剂研究进展.农药学学报,2002,4(1):1-8
[138]王建国,赵卫光,王素华,等.原卟啉原氧化酶及其抑制剂的近期研究.农药,2002,43(8):1-4
[139]刘长令.原卟啉原氧化酶抑制剂的创制经纬.农药,2003,42(1):38-40
[140]梅新娅.原卟啉原氧化酶(Protox)抑制剂研究与开发新进展.湖北化工,2003,增刊,4-5
[141]任叶果,黄明智,侯仲轲.四氢酞酰亚胺类除草剂的研究与开发进展.精细化工中间体,2004,34(6):7-9,20
[142]苏少泉.靶标原卟啉原氧化酶除草剂的发展.农药,2005,44(8):342-346
[143]陈凯,杨华铮,李永红.新型原卟啉原氧化酶抑制剂的固相合成及生物活性研究.高等学校化学学报,2001,22(10):111-115
[144]周宇涵,苗蔚荣,程侣柏,等.取代苯基吡唑类化合物的合成及其除草活性.高等学校化学学报,2003,24(7):1225-1230
[145]周宇涵,苗蔚荣,程侣柏,等.N-芳基唑烷酮类化合物的合成及其除草活性.农药学学报,2001,3(3):71-73
[146]李斌,徐基东,满瀛,等.具有除草活性的2-(硫代)-4,5-咪唑啉三酮类化合物.中国专利,CN 00110477.2,2001-12-12
[147]周宇涵,苗蔚荣.四取代苯基噁唑烷酮类除草剂.中国专利,CN 00126117.7,2001-01-24
[148]李彦龙,王俊春.取代苯基噁唑烷酮类除草剂.中国专利,CN 01117477.3,2001-12-26
[149]周宇涵,苗蔚荣.取代苯基五元氮杂环类除草剂.中国专利,CN 02143654.1,2003-03-19
[150]洪露,王风云,倪珏萍,等.一种取代苯基杂环类化合物除草剂.中国专利,CN 00112213.4,2000-10-04
[151]刘长令,张宗俭,刘晓楠,等.取代三唑、咪唑、吡唑类除草剂.中国专利,CN 00110501.9,2001-12-26
[152]李斌,徐基东,徐龙鹤,等.苯甲酸基不饱和羧酸酯类除草剂.中国专利,CN 00110478.0,2001-12-12
[153]李斌,徐基东.具有除草活性的3-(2-氟-4,5,6-取代苯基)-1,3-喹唑啉-2,4-二酮类化合物.中国专利,CN 00123348.3,2002-06-26
[154]李斌,徐基东.具有除草活性的3-(2-氟-4,5,6-取代苯基)-1,3-苯并嘧啶-4-酮类化合物.中国专利,CN 00123349.1,2002-06-26
[155]徐基东,李斌.具有除草活性的3-取代苯基-1,2,3-苯并三嗪-4-酮类化合物.中国专利,CN 00123023.9,2002-04-24
[156]侯仲轲,任叶果,黄明智,等.一种具有生物活性的杂环取代苯并噁嗪环类化合物.CN 03118226.7,2003-09-17
[157]陈凯.基于药效团模型的新型靶酶抑制剂的设计、合成、生物活性及膦酰基烯酮硫代缩醛的反应研究:[博士学位论文].天津:南开大学,2001
[158]李爱秀,王瑾玲,缪方明.原卟啉原氧化酶抑制剂的三维药效团研究.计算机与应用化学,2002,19(3):335-338
[159]李爱秀,王瑾玲,缪方明.距离比较法(DISCO)构建原卟啉原氧化酶抑制剂药效团模型.化学学报,1999,57:1226-1232
[160]高爽,叶非.靶标酶在除草剂研究与开发中的应用.农药科学与管理,2005,26(1):25-29
[161] Dayan F E, Duke S O. Overview of protoporphyrinogen oxidase-inhibiting herbicides. In: Proceeding of Brighton Crop Prot. Conf.—Weeds. Surrey: British Crop Protection Council, 1997, 83-92
[162] Duke S O, Dayan F E, Yamamoto M, et al. Protoprophyrinogen oxidase inhibitors—their current and future roles. In: Proceeding of second international Weed Control Congress. Copenhagen, 1996. 775-780
[163] Nagano E. Herbicidal efficacy of protoporphyinogen oxidase inhibitors. In: Boger P, Wakabayashi K, eds. Peroxidizing Herbicides. Berlin: Springer, 1999. 293-302
[164] Nandihalli U B, Duke S O. Structure-activity relationship of protoporphyrinogen oxidase inhibiting herbicides. ACS Symp. Ser. 559 (Prophyric Pesticides), 1994, 133-146
[165] Hayashi Y, Furusaki A, Tagashira M. Crystal structure and postemergent herbicidal activity of geometrical isomers of methyl [[[1-[5-[2-chloro-4-(trifluoro- methyl) phenoxy]- 2-nitrophenyl]-2-methoxy-ethylidene]amino]oxy]acetate. J. Agric. Food Chem., 1991,38:2086-2089
[166] Lyga J W, Chang J H, Theodoridis G. Structural replacements for the benzoxa- zinone protox inhibitors. Pesticide Sci., 1999, 55: 281-287
[167] Wakabayashi K. Molecular design of cyclicimide herbicides using biorational approaches. Pesticide Sci., 1988,13: 337-361
[168] Lyga J W, Patera R M, Theodoridis G, et al. Synthesis and quantitative structure- activity relationships of herbicidal N-(2-Fluoro-5- methoxyphenyl)-3,4,5,6-tetra- hydrophthalimides. J. Agric. Food Chem., 1991, 39: 1667-1673
[169] Ishida S, Hirai K, Kohno H, et al. Protoporphyrinogen-IX oxidase inhibition by N- (2,4,5-trisubstituted phenyl)-3,4,5,6- tetrahydrophthalimides. Pesticide Sci., 1997, 22: 299-302
[170] Ishida S, Iida T, Kohno H., et al. Comparison of phytotoxicities between 4-fluo- rinated and non-fluorinated 2-chloro-5-(3,4,5,6-tetrahy- drophthalimido)benzoates. Pesticide Sci., 1999,24: 28-32
[171] Iida T, Uchida A, Uraguchi R, et al. Peroxidizing phytotoxicities of 1,2-dialkyl- 1,2,4-triazolidines and 3,4-dialkyl-1,3,4-thiadiazolidines. Pesticide Sci., 1997, 22: 303-308
[172] Chang J H, Lyga J W. Preparation of tetrazolinone herbicides. US 4734124, 1988-03-29
[173] Hirai K, Yano T, Matsukawa T, et al. Synthesis and herbicidal activity of new oxazolidinedione derivatives. Pesticide Sci., 1999,24: 156-169
[174]Hiraki M,Ohki S,Sato Y,et al.Protoporphyrinogen-Ⅸ oxidase inhibitors:Bioactivation of thiadiazolidines.Pestic.Biochem.Physiol.,2001,70:159-167
[175]Miyamoto Y,Ikeda Y,Wakabayashi K.Synthesis and phytotoxic activities of N-substituted phenyl isothiazolone derivatives.Pesticide Sci.,2003,28:293-300
[176]Meazza G,Bettarini F,Porta P L,et al.Synthesis and herbicidal activity of novel heterocyclic protoporphyrinogen oxidase inhibitors.Pest.Manag.Sci.,2004,60:1178-1188
[177]Nagano H,Haga T,Sato M,et al.Tetrahydrophthalimides and their herbicidal use.US 4640707,1987-02-03
[178]Ohta H,Suzuki S,Watanabe H.N-(p-chlorophenyl)-3,4,5,6-tetrahydrophthalimide.Agr.Biol.Chem.1976,40(4),745-751.
[179]Ohta H,Jikihara T,Wakabayashi K.Quantative structure-active study of herbicidal N-aryl 3,4,5,6 tetrahydrophthalimides and related cyclic imides.Pestic.Biochem.Physiol.1980,14,153-160.
[180]Kwon J W,Armbrust K L,Grey T L.Hydrolysis and photolysis of flumioxazin in aqueous buffer solutions.Pest.Manag.Sci.,2004,60:93-43
[181]Wong J L,Fuchs D S.Reactivities and electronic aspects of diazomethane methylation of uracil and its methyl derivatives.J.Org.Chem.1971,36,848-850.
[182]Gambacorta A,Farah M E,Tofani D.HSAB drive chemoselectivity in alkylation of uracil derivatives.Tetrahedron 1999,55,12615-12628.
[183]杨瑞娜,孙雨安,邝爱燕,等.四氢酞酰环状亚胺类除草剂的开发进展.农药,2001,40(10):7-9,11
[184]Duke S O,Lydon J,Becerril J M,et al.Protoporphyrinogen oxidase-inhibiting herbicides.Weed Science,1991,39:465-473
[185]Haga T,Nagano E,Sato R,et al.Tetrahydrophthalimide derivatives,their production and use.EP 0322401,1989-06-28
[186]Stetter J,Santel H,Schmidt R,et al.N-arylpyrroline-2,5-diones.EP 0288789,1988-11-02
[187]Nagano E,Hashimoto S,Yoshida R,et al.Tetrahydrophthalimide compounds,and their production and use.EP 0083055,1983-07-06
[188]George Y S,Essam D F.Synthesis and properties of somw new N,N-disubstituted thiorueas of biological interest.J.Heterocycl.Chem.1985,22(1),137-140.
[189]茹呈杰,龚富生.酰基硫脲化合物的合成及其生理活性.应用化学,1994,11(3),92-95.
[190]郭佃顺,黄汝骐,高蓉华.N-取代三氯乙酰胺合成新脲类化合物及其生物活性 的研究(Ⅰ).高等学校化学学报,1996,17(2),255-257.
[191]郭佃顺,黄汝骐,高蓉华.N-取代三氯乙酰胺合成N,N-多亚甲基双(N-(4-氯苯基)脲.合成化学,1996,4(1),91-92.
[192]杨华铮.农药分子设计.北京:科学出版社,2003.125-144
[193]刘长令.世界农药大全-除草剂卷.北京:化学工业出版社,2002.387
[194]Eckert H,Forster B.Triphosgen,a crystalline phosgene substitute.Angew.Chem.Int.Ed.Engl.,1987,26:894-895
[195]Organic chemical for research and development 2003-2004.Germany:ABCR GmbH & Co.KG,2003.345,1244
[196]李润卿,范国梁,渠荣遴.有机结构波谱分析.天津大学出版社,天津,2002:203.
[197]邓胜娄,陈茹玉,杨秀凤.1,3-双芳氧乙酰基-1,3,2-二氮磷杂环戊烷-2-硫(硒)化代合物的合成及除草活性研究.高等学校化学学报,2001,22(11),1833-1837.
[198]贺红武,汪军,刘钊杰.具有生物活性的有机磷化合物的研究-[(取代)芳氧基乙酰氧基]烷基膦酸.应用化学,1994,11(4),21-24.
[199]殷树梅.植物生长调节剂P-703的合成.山东化工,1988,(1),28.
[200]袁德茂.芳氧基乙酸的合成.农药,1988,27(6),13.
[201]卿凤翎.芳氧基乙酸的三相催化合成.化学试剂,1989,11(4),250.
[202]李英俊,付兴吉.超声波辐射固-液相芳氧(硫)基羧酸的合成.应用化学,1993,10(6),97-98.
[203]唐除痴,李煜昶,陈彬.农药化学.天津:南开大学出版社,1998:L522-530.
[204]李超,覃章兰,李秀文,等.4-甲基-苯磺酸-2-氧-2-[3-(5-芳基-[1,3,4]噁二唑-2-基)-硫脲]-乙基酯的合成及生物活性研究.有机化学,2005,25(5),587-590.
[205]杨新玲,张钟宁.一类新型酰基脲化合物的设计合成及生物活性.高等学校化学学报,1997,18(3),395-398.
[206]柏再苏,王大翔.新杂环农药的研究发展及合成方法.北京:化学工业出版社,2004:363.
[207]张一宾.世界酰胺类除草剂发展概述.农化新世纪,2006,(5):23
[208]Sawada Y,Yanai T,Nakagawa H,et al.Synthesis and insectididal activity of benzoheterocyclic analogues of N-benzoyl-N-(tert-butyl)benzohydrazide.Pest.manage.Sci.2003,59,25.
[209]Michlotti E L,Young D H.Heterocyclic N-acetonylbenzamides and their use as fungicides.EP 1 229037,2002-08-07
[210]Agrade A,Singh R,Li H,et ai.2,4-Pyrimidineamine compounds.WO 0513996,2004-05-18
[211]Katayama T,Kawamura S,Sanemitsu Y,et al.Pyridazin-3-one derivatives,their use,and intermediates for their production.WO 9707104,1997-02-27
[212]Hoelscher P,Rehwinkel H,Jaroch S.Benzoxazine and benzothiazine derivatives and hteir use in pharmaceuticals.WO 9912915,1999-03-18
[213]Schallner O,Schwarz H G.,Hoischen D,et al.Substituted benzo-nitro-heterocycles and use thereof as herbicides.WO 0206277,2002-01-24
[214]黄春艳,陈铁保,王宇,等.丙炔氟草胺土壤处理防除春玉米田杂草效果初报.中国农学通报,2001,17(6),88-90.
[215]黄春艳,陈铁保,王宇,等.丙炔氟草胺茎叶处理防除春玉米田阔叶杂草效果评价.杂草科学,2001,2:25-26.
[216]杨剑波,庞怀林,黄超群.氟咯草酮的合成研究.精细化工中间体,2005,35(4):24-27.
[217]Hayes N V,Brabch G K.The acidic dissociation constants of phenoxyacetic acid and its derivatives.J.Amer.Chem.Soc.,1943,65:1555-1564
[218]Haga T,Nagano H,Sato M,et al.Benzoxazine derivatives.JP 61140570,1986-06-27
[219]Haga T,Nagano H,Sato M,et al.Nitrobenzoxazine derivatives.JP 61140571,1986-06-27
[220]Haga T,Nagano H,Sato M,et al.4-Substituted nitrobenzoxazine derivatives.JP 61140572,1986-06-27
[221]Haga T,Nagano H,Sato M,et al.Aminobenzoxazine derivatives.JP 61140573,1986-06-27
[222]Hsu A C.Benzoxazolone compounds and the use thereof as microbicides.US 5102898,1992-04-07
[223]阳海,庞怀林,等.催化加氢合成6-氨基-7-氟-4-取代-2H-苯并[6][1,4]噁嗪-3(4H)-酮.精细化工,2006,23(11):1142-1144
[224]黄引,庞怀林,等.雷尼镍催化加氢合成7-氟-4-取代-2H-苯并[6][1,4]噁嗪-3(4H)-酮.精细化工中间体,2006,36(4):28-29
[225]庞怀林,阳海,尹笃林,等.N-(取代)-6-(3-氯-4-氯甲基-2-氧吡咯烷-1-基)-7-氟-3,4-二氢-2H-[1,4]苯并噁嗪-3-酮衍生物的合成与生物活性研究.有机化学,2007,27(9):1130-1136
[226]Miriam B,Luca Forti,Franco G,et al.Halogen atom transfer radical cyclization of N-allyl-N-benzyl-2,2-dihaloamides to 2-pyrrolidinoes,pomoted by Fe~0-FeCl_3 or CuCl-TMEDA.Tetrahadron,1997,53(41):14031-14042.
[227]Franco G,Franco B,Luca F,et al.The influence of benzylic protection and allylic substituents on the CuCl-TMEDA catalyzed rearrangement of N-Allyl-N-Benzyl -2,2-Dihaloamides to γ-Lactams.Application to the stereoselective synthesis of Pilotactam.Tetrahadron,1999,55:5839-5852.
[228]Hughes D,Peace J E.Preparation ofpyrazolecarboxamides as novel insecticides.WO 200585234,2005-7-15
[229]李斌,白丽萍,等.1-[7-氟-4-炔丙基-1,4-苯并噁嗪-3-酮-6-基]-3-正丙基-2-硫代咪唑啉三酮的合成及其除草活性.现代农药,2005,4(3):19-20
[230]Xu,Shangcheng;Wan,Qin;et al.Synthesis and insecticidal activity of 2-(p-chloroph- enyl)pyrrole-3-carbonitriles.南京农业大学学报,2004,27(4):110-113
[231]Aylvie M,Muriel R.,et al.The possible role of hydroxylation in the detoxification of atrazine in the detoxification ofatrazine in mature vetiver(Chrysopogon zizanioides Nash)grown in hydroponics.Journal of Biosciences,2005,60(5/6):427-434
[232]Ho Sik,K.;Seong Uk,L..Synthesis ofpyrazolyl-1,4-benzoxazine derivatives.Journal of the korean Chemical Society,2004,48(4):451-455
[233]Katsutoshi F,Yasushi N,et al.Preparation of haloalkenes and their use as pesticides.JP 200636706,2006-02-09
[234]Peter H,Hartmut R.Benzoxazine and benzothiazine derivatives and their use as nitric oxide synthase inhibitors.WO9912915,1999-03-18
[235]Yoshihiro K,Hidetatsu I,et al.Preparation of condensed pyrimidinone derivatives as herbicides.JP 2000247975,2000-09-12
[236]Huang M Z,Huang K L.Synthesis and herbicidal activity of 2-(7-fluoro-3-oxo-3,4-dihydro-2H-benzo[b][1,4]orazin-6-yl)isoindoline-1,3-diones.J.Agric.Food Chem.2005,53:7908-7914.
[237]刘长令.对羟基苯基丙酮酸酯双氧化酶抑制剂的研究进展.农药.1999,38(2):5-9.
[238]苏少泉.HPPD-开发除草剂品种的新靶标.农药.2000,39(5):4-7.
[239]叶贵标.除草剂作用机理分类法及其应用.农药科学与管理.1999,20(1):32-35.
[240]吴彦超,胡方中,杨华铮.HPPD抑制剂的研究进展.农药学学报.2001,3(3):1-10.
[241]杨丽,张荣全,叶非.对羟苯基丙酮酸双氧化酶抑制剂的研究进展.现代农药.2003,2(5):1-4.
[242]Jayasree V,Rong A,et al.Preparation of benzopyran and related analogs for treating retinoid responsive disorders using selective inhibitors of CYP26A and CYP26B.WO 200558301,2005-5-8
[243]Christoph L,Andrew E,et al.Preparation of substituted pyridines as herbicides.WO 200558831,2005-06-30
[244]Yuji N,Makiko S.Preparation oftriketone compounds,2-benzoylcyclohexane-1,3-diones and enol esters thereof as herbicides.WO 2005118530,2005-12-15
[245]Andreas V A,Lothar W,et al.Preparation of benzoylcyclohexanedionen derivative herbicides.US 2005282710,2005-12-22
[246]Sebastlan,W.;Renaud,B.;et al.Preparation of(3-alkoxypropyl)pyridinyl ketones with herbicidal activities.WO 200666871,2006-06-27
[247]张永华.对氯苯甲酸的合成.天津大学学报,2001,34(3):389-391.
[248]李祥龙,庞怀林,杨剑波.2-硝基-4-甲砜基苯甲酸的合成方法.精细化工间体,2004,34(6):18-20.
[249]Brown S M.Process for the preparation of acylated cyclic 1,3-dicarbonyl compounds.GB9803458,1990-06-10.
[250]SMART 5.0 and SAINT 4.0 for Windows NT:Area Detector Control and Integration Software.Madison:Bruker Analytical X-ray Systems,Inc.1998
[251]Sheldrick G M.SHELXTL:Structure Determination Software Programs.Madison:Bruker Analytical X-ray System,Inc.1997
[252]邓立刚,徐炳祥,姚斌.碘代炔丙基氧羟基丙氨酸甲酯合成方法的改进.化学世界,1997,38(11):589-590.
[253]Utsunomiya A,Nakamura M,Kuwatsuka T,et al.Process for the preparation of iodo alkynyl earbamates.US 5183927.1993-02-02.
[254]Punjia N,Fungicidal compounds,compositions and processes.US 4325966.1982-04-20.
[255]Nagano,E.;Haga,T.;Sato,R.;et al.Tetrabydrophtalimides,and their production and use.EP 170 191.1986-02-05.
[256]吴兆民,刘华俊,陈红艳,等.一氯化碘的乙酸溶液制法改进.化学试剂,2002,24(1):33-34.
[257]陈红艳,吴兆民.一氯化碘乙酸溶注解对芳香化合物碘化的研究.山西师范大学学报(自然科学版),2003,17(3):43-47.