Thifluzamide 噻氟菌胺

中文通用名称; 噻氟菌胺
英文通用名称: trifluzamide （ISO建议名）
商品名称: GreatamGranual，宝穗
化学名称:
2’ ,6 ’ -二溴-2-甲基-4’ -三氟甲氧基-4-三氟甲基-1,3-噻二唑-5-羧酰苯胺
2’ ,6 ’ -dibromo-2-methyl-4’ -trifluoromethoxy-4-trifluoromethyl-1,3-thiazole-5-
carboxanilide

CA主题索引名及CAS登录号:
N-[2,6-dibromo-4-(trifluoromethoxy)phenyl]-2-methyl-4-(trifluoromethyl)-5-thia-
zolecarboxamide
[130000-40-7]
化学结构类型: 噻唑酰胺类
理化性质: 纯品为白色至浅棕色粉状固体；熔点177.9~178.6℃；溶解度(20℃) 水1.6mg/l；分配系数 LogP＝4.1；在 pH=5~9时稳定。
毒性:
大鼠急性经口L D50：>5000mg/kg； 大鼠急性经皮L D50：>5000mg/kg；大鼠吸入LC50：>1.4mg/l空气；本品对兔眼睛有中度刺激，对兔皮肤有轻微刺激。Ames试验呈阴性，小白鼠微核试验为阴性。鹌鹑、野鸭L C50：>5620ppm；鱼L C50(96小时,mg/l)：大翻车鱼鲤鱼1.2，鲤鱼2.9， 虹鳟1.3；水蚤 LC50(48小时)：2.9mg/l。
制剂: 25％W P、 20％SC、 50％S C、50％S G、0.85％D P、15％F S
作用机理: 琥珀酸酯脱氢酶抑制剂即在真菌三羧酸循环中抑制琥珀酸酯脱氢酶的合成。
适宜作物: 水稻、禾谷类作物和草坪
对作物安全性: 推荐剂量下对作物安全、无药害
防治对象: 对丝核菌属、柄锈菌属、黑粉菌属、腥黑粉菌属、伏革菌属和核腔菌属等致病真菌有活性，对担子菌纲真菌引起的病害如立枯病等有特效。
应用:
thifuzamide既可用于水稻、禾谷类作物和草坪等的茎叶处理(使用剂量为125~250克有效成分/公顷)，又可用于禾谷类作物和非禾谷类作物拌种处理( 7~30克有效成分/ 100千克种子)，具有广谱活性且防效优异。
对稻纹枯病有优异的防效，茎叶喷雾处理或施颗粒剂(抽穗前50~20天)，用量分别为130、140克有效成分/公顷，活性优于戊菌隆(330、560克有效成分/公顷)。田间药效试验结果表明对禾谷类锈病有很好的活性，使用剂量为125~250克有效成分/公顷。
以7~30克有效成分/ 100千克种子进行种子处理，对黑粉菌属和小麦网腥黑粉菌亦有很好的防效。对花生枝腐病和锈病有活性(280~560克有效成分/ 100千克种子)。对马铃薯茎溃疡病有很好的效果 (50克有效成分/ 100千克种子)，活性优于戊菌隆和甲基立枯磷。

合成方法:
以三氟乙酰乙酸乙酯为起始原料，经氯化、合环、水解、酰氯化制得酰氯，此酰氯
与以对氨基酚为起始原料制得的( I )反应即得目的物：

主要原料与中间体: 三氟乙酰乙酸乙酯、对氨基酚、氟化氢
分析方法: G C或HPLC
开发公司: 孟山都公司研制，现有罗门哈斯公司进行商品化开发 。
在我国登记情况: 该品种已向国家石油和化学工业局申请行政保护。

thifluzamide
Fungicide
FRAC 7, C2; carboxamide

NOMENCLATURE
Common name thifluzamide (BSI, pa E-ISO, ANSI)
IUPAC name 2',6'-dibromo-2-methyl-4'-trifluoromethoxy-4-trifluoromethyl-1,3-thiazole-5-carboxanilide
Chemical Abstracts name N-[2,6-dibromo-4-(trifluoromethoxy)phenyl]-2-methyl-4-(trifluoromethyl)-5-thiazolecarboxamide
CAS RN [130000-40-7] Development codes MON 24000 (Monsanto); RH-130 753 (Rohm & Haas)

PHYSICAL CHEMISTRY
Composition Tech. is 96.4% nominal purity. Mol. wt. 528.1 M.f. C13H6Br2F6N2O2S Form White to light brown powder. M.p. 177.9-178.6 ºC V.p. 1.008 ´ 10-6 mPa (20 ºC) KOW logP = 4.16 (pH 7) S.g./density 2.0 (26 °C) Solubility In water 1.6 mg/l (pH 5.7), 7.6 mg/l (pH 9) (20 ºC). Stability Stable to hydrolysis at pH 5.0-9.0 Aqueous photolysis DT50 3.6-3.8 d. pKa 11.0-11.5 (20 °C) F.p. >177 °C

COMMERCIALISATION
History Reported by P. O'Reilly et al. (Proc. Br. Crop Prot. Conf. - Pests Dis., 1992, 1, 427). Initially developed by Monsanto Co. and sold to Rohm & Haas Co. (now Dow AgroSciences) in 1994. First marketed in Korea in 1997. Manufacturers Dow AgroSciences

APPLICATIONS
Biochemistry Inhibition of succinate dehydrogenase in the tricarboxylic acid cycle. Mode of action Rapidly absorbed by roots and leaves and translocated throughout the plant, when applied as a foliar spray or a soil drench. Uses Control of a wide range of Basidiomycete fungi on rice, cereals, field crops and turf, by foliar application and as a seed treatment. It is particularly effective for foliar treatment of Rhizoctonia, Puccinia and Corticium, and for seed treatment of Ustilago, Tilletia and Pyrenophora. Applied as a foliar treatment in rice at 50-150 g/ha; higher rates (200-300 g/ha) are required when used in rice as a seedling box treatment. Registered for use in rice (Japan, China, Korea), turf (Japan) and potatoes (Latin America). Formulation types FS; SC; WG; WP. Selected products: 'Greatam' (Dow AgroSciences, Nissan); 'Pulsor' (Dow AgroSciences)

OTHER PRODUCTS
Discontinued products: 'Beaton' * (Dow AgroSciences); 'Thicarbanil' * (Dow AgroSciences)

MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for rats >6500 mg/kg. Skin and eye Acute percutaneous LD50 for rabbits >5000 mg/kg. Slightly irritating to eyes and skin (rabbits). Not a skin sensitiser. Inhalation LC50 (4 h) for rats >5 g/l. NOEL For rats 1.4 mg/kg daily, mice 9.2 mg/kg daily, for dogs 10 mg/kg daily. ADI RfD 0.014 mg/kg daily Other Negative in the Ames test; negative for oncogenicity.

ECOTOXICOLOGY
Birds Oral LD50 for bobwhite quail and mallard ducks >2250 mg/kg. Dietary LC50 for bobwhite quail and mallard ducks >5620 mg/kg. Fish LC50 (96 h) for bluegill sunfish 1.2, rainbow trout 1.3, carp 2.9 mg/l. Daphnia EC50 (48 h) 1.4 ppm. Algae EC50 for green algae 1.3 mg/l. Bees LD50 (oral) for honeybees >1000 ppm; (contact) >100 mg/bee. Worms LC50 >1250 mg/kg.

ENVIRONMENTAL FATE
Animals Extensively metabolised by five primary pathways. Plants Thifluzamide resides in the leaf mainly as the parent molecule. Soil/Environment Does not degrade readily by hydrolysis. Microbial degradation in soil is slow. Mobility potential in soil is low.