Fluoxastrobin 氟嘧菌酯

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Fluoxastrobin 氟嘧菌酯

CAS号: 361377-29-9
英文名称: FLUOXASTROBIN
IUPAC: (E)-{2-[6-(2-chlorophenoxy)-5-fluoropyrimidin-4-yloxy]phenyl}(5,6-dihydro-1,4,2-dioxazin-3-yl)methanone O-methyloxime
CAS: (1E)-[2-[[6-(2-chlorophenoxy)-5-fluoro-4-pyrimidinyl]oxy]phenyl](5,6-dihydro-1,4,2-dioxazin-3-yl)methanone O-methyloxime
化学名称为: { 2 -〔6- (2 -氯苯氧基 ) - 5 -氟嘧啶 - 4 -基氧〕苯基 } (5 ,6-二氢 - 1,4 ,2 -二嗪 - 3-基 )甲酮O -甲基肟
中文名称: 氟嘧菌酯
中文同义词:
CBNumber: CB6505916

分子式: C21H16ClFN4O5
分子量: 458.83
MOL File: 361377-29-9.mol

理化性质:
1.纯品为白色结晶固体。
2.m.p.75℃,蒸气压6×10-10Pa(20℃)。
3.分配系数2.86。
4.20℃ pH值7时在水中溶解度2.29 mg/L,在土壤中降解半衰期为16~119d。

毒性数据:
大鼠急性经口LD502500mg/kg,大鼠急性经皮LD50>2000mg/kg。对兔眼睛有刺激作用,对兔皮肤无刺激作用,对豚鼠皮肤无致敏作用。对大鼠或兔未发现胚胎毒性、繁殖毒性和致畸作用,无致癌作用和神经毒性。鹌鹑经口LD50>2000mg/kg,鳟鱼LC50>0.44mg/L (96h), 水蚤EC500.48mg/L (48h),蚯蚓LC50>1000mg/kg土, 蜜蜂LD50>843 μg/只。

生产工艺:
1.中间体的制备: 以2-氟并二酸二乙酯和邻羟基苯乙酸甲酯为原料,分别经如下反应,获氟嘧菌酯合成的两个重要中间体。
2.氟嘧菌酯的合成: 通过如下两种方法合成氟嘧菌酯。
其中最后一步的具体操作如下。
在20℃,将136.8g (0.56mol)4-(2-氯苯氧基)-5,6-二氟嘧啶加入到135.3g (0.56mol) 3-[1-(2-羟基苯基)-1-(甲氧氨基)-甲基]-5,6-二氢-1,4,2-二噁嗪和197.6g碳酸钾于460mL乙腈混合溶液中,温度升至31℃。并于50℃搅拌反应6h,然后室温搅拌过夜,将混合液倒入2.3L冰水中,搅拌反应5h,过滤,水洗,干燥得到260g (97.8%)氟嘧菌酯,m.p.为75℃。
过124.1g (0.333mol)3-{1-[2-(4,5-二氟嘧啶-6-基氧基)-苯基]-1-(甲氧氨基)-甲基}-5,6-二氢-1,4,2-二噁嗪、42.8g (0.333mol)邻氯苯酚、46g(0.333mol) 碳酸钾和3.3g氯化亚酮于1L DMF的混合液加热到100℃过液;减压脱溶后冷却至20℃,加入乙酸乙酯和水,分出有机层,干燥、过滤、羊城压脱溶后得到148.2g (97%)氟嘧菌酯。

作用原理:
氟嘧菌酯:
制剂10%乳油(EC),其他剂型在砑究中。
作用机理与特点同嘧菌酯及其他甲氧基丙烯酸酯类杀菌剂一样,氟嘧菌酯的作用机理也是线粒体呼吸抑制剂,即通过在细胞色素b和C1间电子转移抑制线粒体的呼吸。作用于线粒体呼吸的杀菌剂较多,但甲氧基丙烯酸酯类化合物作用的部位(细胞色素b)与以往所有杀菌剂均不同,因此防治对甾醇抑制剂(sterolinhibitors)、苯基酰胺类(phenylamides)、二羧酰胺类(dicarboximides)和苯并咪唑类(benzimidazoles),产生抗性的菌株有效。
氟嘧菌酯应用适期广,无论在真菌侵染早期如孢子萌发、芽管生长以及侵入叶部,还是在菌丝生长期都能提供非常好的保护和治疗作用;但对孢子萌发和初期侵染最有效。因具有的优异的内吸活性,它能被快速吸收,并能在叶部均匀地向顶部传递,故具有根好的耐雨水冲刷能力。

应用使用:
适宜作物与安全性禾谷类作物、马铃薯、蔬菜和咖啡等,推荐剂量下对作物安全、对地下水、环境安全。
防治对象氟嘧茵酯具有广谱的杀菌活性,对几乎所有真菌纲(子囊菌纲、担子菌纲、卵菌纲和半知菌类)病害如锈病、颖祜病、网斑病、白粉病、霜霉病等数十种病害均有很好的活性。
使用方法氟嘧菌酯主要用于茎叶处理,使用剂量通常为50~30Og(a.i.)/hm2。氟嘧菌酯具有速效和持效期长双重特性,对作物具有很好的相容性,适当的加工剂型可进一步提高其通过角质层进人叶部的渗透作用。尽管它通过种子和根部的吸收能力较差,但用作种子处理剂时,对幼苗和种传和土传病害虽具有很好的杀灭和持效作用,不过对大麦白粉病或网斑病等气传病害则无能为力。
在75~l00g(a.i.)/hm2剂量下茎叶喷雾,氟嘧菌酯对咖啡锈病具有优异防效。
在100~200g(a.i.)/hm2剂量下茎叶喷雾,氟嘧菌酯对马铃薯早疫病等有优异防效,对晚疫病有很好的防效;对蔬莱叶斑病等具有优异防效,对霜霉病有很好的防败。
在200g(a.i.)/hm2剂量下茎叶喷雾,氟嘧菌酯对禾谷类作物叶斑病、颖祜病、褐锈病、条锈病、云纹病、褐斑病、网班病具有优异防效,对白粉病有很好的药效,并能兼治全蚀病。
氟嘧菌酯作禾谷类作物种子处理剂时处理浓度为5~l0g(a.i.)/l00kg种子,对雪霉病、腥黑穗病和坚黑穗病等种传和土传病害有优异防效,并能兼治散黑穗病和叶条纹病。

 

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fluoxastrobin

IUPAC: (E)-{2-[6-(2-chlorophenoxy)-5-fluoropyrimidin-4-yloxy]phenyl}(5,6-dihydro-1,4,2-dioxazin-3-yl)methanone O-methyloxime
CAS: (1E)-[2-[[6-(2-chlorophenoxy)-5-fluoro-4-pyrimidinyl]oxy]phenyl](5,6-dihydro-1,4,2-dioxazin-3-yl)methanone O-methyloxime
Reg. No.: 361377-29-9
Formula: C21H16ClFN4O5
Activity: fungicides
Chemical Class: strobilurins, methoxyacrylates
Structure:

fluoxastrobin
PHYSICAL AND CHEMICAL PROPERTIES
Technical fluoxastrobin is a white, crystalline solid. It is essentially insoluble in water (solubility of 0.0023 g/L in water at pH 7), but is highly soluble in dichloromethane, polyethylene glycol 400, acetone, ethyl acetate, acetonitrile, and dimethylsulfoxide. Technical fluoxastrobin has a melting point of 103-105°C, and a log Pow of 2.85 at 20°C. It does not dissociate in water at pH 4 to 9 and has a vapor pressure of 5.63x10-10 Pa at 20°C.

USE PATTERN AND FORMULATIONS
Pests/Application Sites:
Fluoxastrobin is a new strobilurin-type fungicidal active ingredient (a.i.) for the control of fungal diseases such as early blight, late blight, leaf spots, leaf rust, and Rhizoctonia solani. Fluoxastrobin has been registered for foliar use on peanuts, tuberous and corm vegetables, leaf petiole vegetables, fruiting vegetables, and turf, as well as seed treatment for potato, peanut and turf. Turf applications are labeled for professional pest control operators only, not for homeowners.

Types of Formulations:
Fluoxastrobin will be marketed in its technical form (94.8% a.i., a white crystalline solid) for use in formulations, and as the formulation HEC 480 SC Fungicide (40.3% a.i., an off- white suspension concentrate, Bayer CropScience).

Types and Methods:
HEC 480 SC Fungicide (Bayer CropScience) can be applied by chemigation or by ground or aerial spray, post-emergence. For seed treatment it is applied by slurry or mist type equipment.

Application Rates:
For foliar treatment of agricultural crops, HEC 480 SC (Bayer CropScience) fungicide can be applied up to 4 - 6 times per season at rates of 0.12 to 0.18 lb a.i./A , 7- to 14-day application intervals, and a maximum seasonal application rate of 0.72 lb a.i./A (including seed treatment use); PHIs range from 3 to 14 days. For turf, HEC 480 SC fungicide (Bayer CropScience) is applied up to 4 times per season at application rates of 0.27 to 0.55 lb a.i./A, a minimum 21-day application interval, and a maximum seasonal application rate of 2.2 lb a.i./A. For seed treatment on peanuts and potato seed pieces, HEC 480 SC is applied using slurry or mist-type equipment at a rate of up to 0.010 lb a.i./CWT.
Carrier: Water

HAZARD CHARACTERIZATION
Acute Toxicity
Fluoxastrobin technical has a low order of acute toxicity based on its classification in Toxicity Category III (LD50 > 2000 mg/kg) via the oral and dermal routes, and Toxicity Category IV by the inhalation route of exposure. Fluoxastrobin is a moderate eye irritant (Toxicity Category III), but is neither a dermal irritant nor a sensitizer.
The end use product HEC 480 SC Fungicide is an emulsifiable concentrate. This product has a very low order of acute toxicity based on its classification in Acute Toxicity Category IV for all exposure routes.

Refer to:http://www.epa.gov/pesticides/chem_search/reg_actions/registration/fs_PC-028869_01-Nov-05.pdf