Phthalide 四氯苯酞

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四氯苯酞

中文名称:四氯苯酞
英文名称:phthalide (JMAF); fthalide (JMAF, alternative spelling)
中文同义词:稻瘟酞, 稻瘟酞, 四氯苯酞,4,5,6,7-四氯-2-苯苯并(C)呋喃酮,氯百杀,热必斯,Α-羥鄰甲苯甲酸內酯酞, 4,5,6,7-四氯苯酞, 氯苯酞
IUPAC 名称: 4,5,6,7-四氯苯酞
CAS 名称: 4,5,6,7-四氯-1(3H)-异苯并呋喃酮
CAS RN: [27355-22-2]
分子式:C8H2CI4O2
分子量:271.90

理化特性:
外观与性状:白色粉末。
熔点(℃):209~210
闪点(℃):无意义
蒸气压.: 3 ´ 10-3 mPa (23 ºC)
KOW: logP = 3.01
溶解性: 水中2.5 mg/l (25 ºC). 丙酮8.3, 苯 16.8, 二恶烷 14.1乙醇1.1, 四氢呋喃19.3 (g/l, 25 ºC).
稳定性:
在at pH 2 (2.5 ppm 水溶液)中稳定12小时;
在弱碱环境中, DT50 c. 10 d (pH 6.8, 5-10 ºC, 2.0 ppm );
(pH 10, 25 ºC, 2.5 ppm 水溶液)12小时,发生 15% 开环作用;
对光热稳定。
禁配物:强氧化剂、强碱。

使用:
作用机理 :
作用机理与特点保护性杀菌剂。在稻株表面能有效地抑制附着胞形成,阻止菌丝人侵,具有良好的预防作用,但四氯苯酞在稻株体内,对菌丝的生长设有抑制作用,但能抑制病菌的再侵染。

应用:
主要用于防治水稻白叶枯病和稻瘟病。使用剂量为200~400g(a.i.)/hm2。50%可湿性粉剂64~l00g对水40~50kg喷雾可防治叶瘟病。抽穗前3~5d每亩用50%可湿性粉剂75~l00g对水75kg喷雾可防治穗瘟病。

毒理
经口:小鼠和大鼠的急性经口LD50>10000毫克/公斤。
皮肤和眼:大鼠和小鼠急性经皮LD50>10000毫克/公斤;对眼无刺激,对剃毛兔皮无刺激。
吸入:LC50(4小时),大鼠>4.1g/m3。
NOEL:(2年)大鼠2000,小鼠100 mg/kg 日摄入量。
其他:急性腹腔内LD50,雄性大鼠9780,雌大鼠15 000,小鼠10000毫克/公斤。
毒性等级:WHO(AI)U, EPA(制剂)IV

生态毒理
禽类:母鸡喂1.5毫克/公斤,喂食7天,15毫克/公斤,继续喂3天,无不良反应。
鱼类:LC50(48小时)的年轻鲤鱼>320毫克有效成分(原药或DP)/升,135毫克有效成分(50%可湿性粉剂)/升。
水蚤:LC50(3小时)>40 ppm。
海藻:EC50(96小时)羊角月牙Selenastrum capricornutum> 1000毫克/升。
蜜蜂:无毒,对蜜蜂LD50(接触)>0.4毫克/蜜蜂。
昆虫:LC50(14天)> 2000毫克/公斤 基质。

环境动态:
动物:在大鼠中,主要的代谢物是2-羟甲基-3-3,4,5,6-四氯苯甲酸及其氧化产物。
植物:在水稻中代谢为4,7-二氯苯酞和4,6,7-三氯苯酞。
土壤/环境:在土壤中的主要代谢产物是2-羟甲基-3,4,5,6-四氯苯甲酸及其氧化产物

 

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phthalide
Fungicide
FRAC 16.1, I1; MBI: reductase

  phthalide

NOMENCLATURE
Common name: phthalide (JMAF); fthalide (JMAF, alternative spelling)
IUPAC name: 4,5,6,7-tetrachlorophthalide
Chemical Abstracts name: 4,5,6,7-tetrachloro-1(3H)-isobenzofuranone
Other names: TCP
CAS RN: [27355-22-2]
Development codes: KF-32 (Kureha); Bayer 96 610

PHYSICAL CHEMISTRY
Mol. wt.: 271.9
M.f.: C8H2Cl4O2
Form: Colourless crystals.
M.p.: 209-210 ºC
V.p.: 3 ´ 10-3 mPa (23 ºC)
KOW: logP = 3.01
Solubility: In water 2.5 mg/l (25 ºC). In acetone 8.3, benzene 16.8, dioxane 14.1, ethyl alcohol 1.1, tetrahydrofuran 19.3 (all in g/l, 25 ºC).
Stability: Stable for 12 h at pH 2 (2.5 ppm aq. solution); in weak alkali, DT50 c. 10 d (pH 6.8, 5-10 ºC, 2.0 ppm aq. solution); 15% ring opening in 12 h (pH 10, 25 ºC, 2.5 ppm aq. solution). Stable to heat and light.

COMMERCIALISATION
History: Fungicide reported by K. Nambu (Jpn. Pestic. Inf., 1972, No. 10, p. 73) and by K. Wagner & H. Scheinflug (Pflanzenschutz-Nachr. (Engl. Ed.), 1975, 28, 210). Introduced by Kureha Chemical Co., Ltd in 1971 and manufactured by a process licensed from Bayer AG.
Patents: JP 575584 to Kureha; DE 1643347 to Bayer
Manufacturers: Kureha

APPLICATIONS
Biochemistry: Anti-penetrant action with melanin biosynthesis inhibition (reduction of 1,3,8-trihydroxynaphthalene).
Mode of action: Foliar fungicide with protective action.
Uses: Control of rice blast (Pyricularia oryzae), at 200-450 g/ha.
Formulation types: DP; SC; WP.
Compatibility: Incompatible with pesticides which are strongly alkaline.
Selected products: 'Rabcide' (Kureha);
mixtures: 'Blasin' (+ ferimzone) (Sumitomo Chemical Takeda); 'Hinorabcide' (+ edifenphos) (Nihon Bayer)

OTHER PRODUCTS
Mixtures: 'Hustler' (+ validamycin+ cartap hydrochloride+ clothianidin+ ferimzone) (Sumitomo Chemical Takeda); 'Kasai' (+ kasugamycin hydrochloride hydrate) (Hokko); 'Kasu-rabcide' (+ kasugamycin hydrochloride hydrate) (Hokko); 'Kasu-rab-sumibassa' (+ fenitrothion+ fenobucarb+ kasugamycin hydrochloride hydrate) (Hokko); 'Kasu-rab-valida-sumi' (+ validamycin+ fenitrothion+ kasugamycin) (Hokko); 'Kasu-rab-validatrebon' (+ validamycin+ etofenprox+ kasugamycin hydrochloride hydrate) (Hokko); 'Mon-Rab Trebon F' (+ etofenprox+ flutolanil) (Nihon Nohyaku)

ANALYSIS
Product: analysis is by glc with TCD.
Residues: may be determined by glc with ECD (H. Nagayoshi et al., Bull. Agric. Chem. Inspect. Stn., 1973, 13, 27). Details available from Kureha Chemical Industry Co., Ltd.

MAMMALIAN TOXICOLOGY
Reviews: J. Pestic. Sci., 15(2), 311-314 (1990).
Oral: Acute oral LD50 for rats and mice >10 000 mg/kg.
Skin and eye: Acute percutaneous LD50 for rats and mice >10 000 mg/kg; non-irritating to eyes and shaved skin of rabbits.
Inhalation: LC50 (4 h) for rats >4.1 g/m3.
NOEL: (2 y) for rats 2000, mice 100 mg/kg diet (M. Ishida & K. Nambu, J. Pestic. Sci., 3, 10-26).
Other: Acute i.p. LD50 for male rats 9780, female rats 15 000, mice 10 000 mg/kg.
Toxicity class: WHO (a.i.) U; EPA (formulation) IV

ECOTOXICOLOGY
Birds: No effect on hens fed 1.5 mg/kg for 7 days, and for another 3 days at 15 mg/kg.
Fish: LC50 (48 h) for young carp >320 mg a.i. (as tech. or DP)/l, 135 mg a.i. (as 50% WP)/l.
Daphnia: LC50 (3 h) >40 ppm.
Algae: EC50 (96 h) for Selenastrum capricornutum >1000 mg/l.
Bees: Non-toxic to bees; LD50 (contact) >0.4 mg/bee.
Worms: LC50 (14 d) >2000 mg/kg substrate.

ENVIRONMENTAL FATE
Animals: In rats, principal metabolites are 2-hydroxymethyl-3,4,5,6-tetrachlorobenzoic acid and its oxidation products.
Plants: 4,7-Dichlorophthalide and 4,6,7-trichlorophthalide are formed in rice.
Soil/Environment: Principal metabolites in soil are 2-hydroxymethyl-3,4,5,6-tetrachlorobenzoic acid and its oxidation products (K. Aoki et al., Jpn. Pestic. Inf., 1979, 36, 32).