Fludioxonil 咯菌腈，咯菌酯

咯菌腈

英文名：Fludioxonil
产品名称：咯菌腈; 咯菌酯; 4-(2,2-二氟-1,3-苯并二氧戊环-4-基)吡咯-3-腈[1]
分子式：C12H6F2N2O2
分子量：248.18

作用机理
作用机理咯菌腈的作用机理与拌种咯相同，通过抑制葡萄糖磷酰化有关的转移，并抑制真菌菌丝体的生长，最终导致病菌死亡。作用机理独特，与现有杀茵剂无交互抗性。属非内吸性的广谱杀菌剂。

应用
适宜作物小麦、大麦、玉米、豌豆、油菜、水稻、观赏作物、硬果、蔬莱、葡萄和草坪等。 对作物安全性推荐剂量下对作物安全、无药害。

防治对象
作为叶面杀菌剂用于防治雪腐镰孢菌、小麦网腥黑穗菌、立枯病菌等，对灰霉病有特效；作为种子处理剂：主要用于谷物和韭谷物类作物中防治种传和土传病菌如链格孢属、壳二孢属、曲霉属、镰孢菌屑、长蠕孢屑、丝核菌属及青霉属菌等。具体病害如下：小麦腥黑穗病、雪腐病、雪霉病、纹枯病、根腐病、全蚀病、颖枯病、秆黑粉病“，大麦条纹病、网斑病、坚黑穗病、雪腐病，“玉米青枯病、茎基腐病、猝倒病；棉花立枯病、红庸病、炭疽病、黑根病、种子腐烂病；大豆立枯病、根腐病（镰刀菌引起）；花生立祜病、茎腐病；水稻恶苗病、胡麻叶斑病、早期叶瘟病、立枯病；油菜黑斑病、黑胫病；马铃薯立枯病、疮痂病；蔬菜枯萎病、炭疽病、褐斑病、蔓枯病。

使用方法
主要用作种子处理，使用剂量为2.5～lOg（a.i.）/l00kg种子，，也可用于茎叶处理，防治苹果树、蔬菜、大田作物和观赏作物病害使用剂量为250～500g（a.i．）/hm2，.防治草坪病害使用剂量为400～800g（a.i.）/hm2；防治收获后水果病害使用剂量为30～60g（a.i.）/hL。种子处理操作及具体使用方法如下：

手工拌种
手工拌种准备好桶或塑料袋，将制剂用水稀释（一般稀释到1～2L/l00kg种子，大豆0.6～0.9L/l00kg种子），充分混匀后倒在种子上，快速搅拌或摇晃，直至药液均匀分布到每粒种子上（根据颜色判断）若地下害虫严重可加常用拌种剂混匀后拌种。

机械拌种
机械拌种根据所采用的拌种力学性能及作物种子，桉不同的比例把制剂加水稀释好即可拌种。例如：国产拌种机一般药种比为1：60，可将制剂加水稀释至1660ml/l00kg（大豆为lL/l00kg种子以内）；若采用进口拌种机，一般药种比为1：（80～120），可将制剂加水调配至800～1250ml/l00kg种子的程度即可开机袢种。

制剂
制剂DS、ES、SC、WG、WP。如50%水分散粒剂；l0%粉剂；50%可湿性粉剂等。
大麦、小麦、玉米、花生、马铃薯每l00kg种子用2.5%制剂100～200或10%制剂25～50ml（有效成分2.5～5g）；
棉花每l0Okg种子用2.5%制剂100～400ml，或10%制剂25～l00ml（有效成分2.5～l0g）；
大豆每l00kg种子用2.5%制剂200～40Oml，或10%制剂50～l00ml（有效成分5～l0g）；
水稻每l00kg种子用2.5%制剂200～800ml，或10%制剂50～200ml（有效成分5～20g）；
油菜每l00kg种子用2.5%制剂600ml或10%制剂150ml（有效成分15g）；
蔬莱每l00kg种子用2.5%制剂400～800ml，或10%制剂100～200ml（有效成分10～20g）。

注意事项
1.对水生生物有毒，勿把剩余药物倒入池塘、河流。
2.农药泼洒在地，立即用沙、锯末、干土吸附，把吸附物集中深埋。曾经泼洒的地方用大量清水冲洗。回收药物不得再用。
3.经处理种子绝对不得用来喂禽畜，绝对不得用来加工饲料或食品。
4.用剩种子可以贮放3年，但若已过时失效，绝对不可把种子洗净作饲料及食品。
5.播后必须盖土。

安全措施
1.施药前请详细阅读产品标签，按说明使用。
2.施药时要穿戴防护用具，避免与药剂直接接触。
3.施药后换洗被污染的衣物，妥善处理废弃包装物。
4.药剂应原包装贮存于阴凉、干燥且远离儿童、食品、饲料及火源的地方。
5.中毒解救：无专用解毒剂，若不慎溅入眼中及皮肤上，用大量清水冲洗即可。若误服，应立即送医院对症治疗。

fludioxonil
Fungicide
FRAC 12, E2; phenylpyrrole

NOMENCLATURE
Common name fludioxonil (BSI, pa E-ISO)
IUPAC name 4-(2,2-difluoro-1,3-benzodioxol-4-yl)pyrrole-3-carbonitrile
Chemical Abstracts name 4-(2,2-difluoro-1,3-benzodioxol-4-yl)-1H-pyrrole-3-carbonitrile
CAS RN [131341-86-1] Development codes CGA 173506 (Ciba-Geigy)

PHYSICAL CHEMISTRY
Mol. wt. 248.2 M.f. C12H6F2N2O2 Form Yellowish crystals. M.p. 199.8 ºC V.p. 3.9 ´ 10-4 mPa (25 ºC) KOW logP = 4.12 (25 ºC) Henry 5.4 ´ 10-5 Pa m3 mol-1 (calc.) S.g./density 1.54 (20 °C) Solubility In water 1.8 mg/l (25 ºC). In acetone 190, ethanol 44, toluene 2.7, n-octanol 20, hexane 0.01 g/l (25 ºC). Stability Practically no hydrolysis at 70 ºC between pH 5 and 9. pKa pKa1 <0; pKa2 c. 14.1

COMMERCIALISATION
History Announced by Ciba-Geigy AG (now Syngenta AG) as a novel fungicide for seed treatment (Proc. Br. Crop Prot. Conf. - Pests Dis., 1990, 2, 825-830) and foliar use (ibid., pp. 399-406). First sales in 1993 as a cereal seed dressing and in 1995 as a foliar fungicide, both in France. Patents EP-206999; US 4705800 Manufacturers Syngenta

APPLICATIONS
Biochemistry Mode of action is believed to be the same as for fenpiclonil. Inhibits MAP kinase, in osmotic signal transduction. Mode of action Non-systemic product with long residual activity. Uptake into the plant tissues and curative properties are generally limited. Inhibits mainly the germination of conidia and, to a lesser extent, the germ tube and mycelial growth. Uses As a seed treatment, for control of Fusarium spp., Microdochium, Rhizoctonia, Tilletia, Pyrenophora and Septoria in both cereal and non-cereal crops, at 2.5-10 g/100 kg. As a foliar fungicide, for control of Botrytis, Monilinia, Sclerotinia, and Alternaria in grapes, stone fruit, berry crops, vegetables, and ornamentals, at 250-500 g/ha; also on turf, against Fusarium, Helminthosporium, Rhizoctonia, Sclerotinia and Typhula, at 400-800 g/ha. Also as a post-harvest treatment on stonefruit at 30-60 g/hl against Botrytis, Monilinia and Penicillium. Formulation types DS; FS; SC; WG; WP. Selected products: 'Celest' (seed treatment) (Syngenta); 'Géoxe' (foliar) (Syngenta); mixtures: 'Maxim XL' (+ metalaxyl-M) (seed treatment) (Syngenta); 'Maxim' (+ metalaxyl) (seed treatment) (Syngenta); 'Switch' (+ cyprodinil) (foliar) (Syngenta)

OTHER PRODUCTS
'Atlas' (seed treatment) (Syngenta); 'Medallion' (Syngenta); 'Saphire' (foliar) (Syngenta); 'Savior' (foliar) (Syngenta); 'Scholar' (post-harvest) (Syngenta) mixtures: 'Apron Maxx' (+ metalaxyl-M) (Syngenta); 'Austral Plus' (+ tefluthrin+ anthraquinone) (Syngenta); 'Botryl' (+ cyprodinil) (ornamentals) (Syngenta); 'Celeste Orge' (+ tebuconazole+ anthraquinone+ cyprodinil) (seed treatment, France) (Syngenta); 'Helix' (+ metalaxyl-M+ thiamethoxam+ difenoconazole) (Syngenta); 'Landor CT' (+ tebuconazole+ difenoconazole) (seed treatment, Germany) (Syngenta); 'Maxim Apron' (+ metalaxyl) (Syngenta); 'Maxim MZ' (+ mancozeb) (Syngenta); 'Maxim Star' (+ cyproconazole) (Syngenta); 'Solitär' (+ tebuconazole+ cyprodinil) (seed treatment) (Syngenta); 'Wakil XL' (+ metalaxyl-M+ cymoxanil) (Syngenta); 'Arena C' (+ tebuconazole) (seed treatment, Germany) (Bayer CropScience); 'Justeet' (+ fenhexamid) (Japan) (Bayer CropScience) Discontinued products: 'Elyxor' * (Novartis); 'Wispect' * (Novartis) mixtures: 'Elyxor Star' * (+ tefluthrin+ anthraquinone) (Novartis)

ANALYSIS
Product by glc. Residues by hplc with u.v. detection. Details from Syngenta.

MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for rats and mice >5000 mg/kg. Skin and eye Acute percutaneous LD50 for rats >2000 mg/kg. Non-irritating to eyes and skin (rabbits). Non-sensitising to skin (guinea pigs). Inhalation LC50 (4 h) for rats >2.6 mg/m3 air. NOEL (2 y) for rats 40 mg/kg b.w. daily; (1.5 y) for mice 112 mg/kg b.w. daily; (1 y) for dogs 3.3 mg/kg b.w. daily. ADI 0.033 mg/kg b.w. Other Not teratogenic, not mutagenic, not oncogenic. Toxicity class WHO (a.i.) U (company classification)

ECOTOXICOLOGY
Birds Acute oral LD50 for mallard ducks and bobwhite quail >2000 mg/kg. LC50 for mallard ducks and bobwhite quail >5200 ppm. Fish LC50 (96 h) for bluegill sunfish 0.31, catfish 0.63, common carp 1.5, rainbow trout 0.5 mg/l. Daphnia LC50 (48 h) 1.1 mg/l. Algae EC50 (72 h) for Scenedesmus subspicatus 0.93 mg/l; (120 h) for Selenastrum capricornutum 0.092 mg/l. Bees Non-toxic; LD50 (48 h, oral) >329 mg/bee; LC50 (48 h, contact) >101 mg/bee. Worms LC50 (14 d) for Eisenia foetida >1000 mg/kg soil. Other beneficial spp. No long-term substantial reduction in major groups of zooplankton, bentic macro-invertebrates, emergent insects, peryphyton or phytoplankton; no negative effects on Aleochara, Poecilus, Coccinella, Orius, Aphidius and Typhlodromus.

ENVIRONMENTAL FATE
Animals Rapidly absorbed from the gastrointestinal tract into the general circulation and rapidly and almost completely excreted, via the faeces. The dominant metabolic pathway is oxidation of the pyrrole ring at the 2-position. A minor pathway is hydroxylation of the phenyl ring. All metabolites are excreted as conjugates, mainly as glucuronides. Plants Metabolism proceeds via the oxidation of the pyrrole ring, opening of the pyrrole ring and pyrrolidine carboxylic acid metabolite. In general, the compound is extensively metabolised to more than 10-15 minor metabolites. Soil/Environment Formation of bound residues is the major route for dissipation in soil; DT50 (lab.) 140-350 d, (field) 10-25 d. In leaching and adsorption/desorption experiments, the compound proved to be immobile in soil. Photolytic DT50 in water 9-10 d (natural sunlight).