Fentrazamide 四唑酰草胺

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四唑酰草胺

CAS号: 158237-07-1
英文名称: fentrazamide
化学名称:4-(2-氮苯基)-5-氧-4,5-二氧-四唑-1-羧酸环已基-乙基-酰胺
其他名称:拜田净,四唑草胺, yrc 2388
分子式:C16H20ClN5O2
分子量:349.82

理化性质:纯品为无色结晶体,熔点79℃,蒸气压为5× 1012Pa(20℃)。分配系数LogP=4.01;溶解度(毫克/升,20℃):水2.3,异丙醇32000,二甲苯250000。

毒性 : 据中国农药毒性分级标准,拜田净属低毒除草剂。大鼠急性经口LD50大于5000毫克/千克,大鼠急性经皮LD50大于5000毫克/千克,大鼠急性吸入LC50(4小时)大于5000毫克/ 升。本品对兔眼晴和兔皮肤无刺激。鱼毒LC50(48小时,毫克/升):鲤鱼3.2,虹鳟3.4;水蚤LC50(3小时)大于10毫克/升。Ames等试验呈阴性,无致突变性。

作用特点 及杀草谱: 50%拜田净可湿性粉剂是拜耳公司在中国市场新近推出的全新化学结构的因唑啉酮类高效水田除草剂。可被植物的根、茎、叶吸收并传导到根和芽顶端的分生组织,抑制其细胞分裂,生长停止,组织变形,使生长点、节间分生组织坏死,心叶由绿变紫色,基部变褐色而枯死,从而发挥除草作用。 拜田净对杂草有高度的选择性,对水稻安全,并有良好的保护环境和生态的特性。 适用于水稻(移栽田、抛秧田、直播田)。防治禾本科杂草(稗草、千金子)、莎草料杂草(异型莎草、牛毛毡)和阔叶杂草(鸭舌草)等。水稻直播田苗后、移栽田插秧后0~10天、抛秧田抛秧后0~7天,在稗草苗前至2.5叶期施药,每亩用50%拜田净可湿性粉剂13~26克(有效成分6.5~13克),毒土法或喷雾均可。使用毒土法时,需保证土壤湿润即田间有薄水层,以保证药剂能均匀扩散。
拜田净可以与苄嘧磺隆等磺酰脲类的防阔叶杂草除草剂混用,同时防治多年生莎草料杂草和某些难防治的阔叶杂草。

剂型:50%拜田净可湿性粉剂 ,还有颗粒剂、悬浮剂等剂型。还与氟嘧磺隆、吡嘧磺隆复配。

生产方法:

 

生产情况:国内未见四唑酰草胺的生产报道。

其他:日本拜耳农化公司1992年开发,1994.02.25申请中国专利,CN1045958C(1),CN1130126C(5),尚在保护期,即将到期。

 

 

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fentrazamide
Herbicide
HRAC K3 WSSA 15; tetrazolinone

  Fentrazamide

NOMENCLATURE
Common name fentrazamide (BSI; pa ISO)
IUPAC name 4-(2-chlorophenyl)-N-cyclohexyl-N-ethyl-4,5-dihydro-5-oxo-1H-tetrazole-1-carboxamide
Chemical Abstracts name 4-(2-chlorophenyl)-N-cyclohexyl-N-ethyl-4,5-dihydro-5-oxo-1H-tetrazole-1-carboxamide
CAS RN [158237-07-1] Development codes YRC 2388; BAY YRC 2388 (Bayer); NBA 061

PHYSICAL CHEMISTRY
Mol. wt. 349.8 M.f. C16H20ClN5O2 Form Colourless crystals. M.p. 79 °C V.p. 5 ´ 10-5 mPa (20 °C) KOW logP = 3.60 (20 °C) Henry 7 ´ 10-6 Pa m3 mol-1 (calc.) S.g./density 1.30 (20 °C) Solubility In water 2.3 mg/l (20 °C). In n-heptane 2.1, isopropanol 32, dichloromethane and xylene >250 (all in g/l, 20 °C). Stability DT50 (pH 5) >300 d, (pH 7) >500 d, (pH 9) c. 70 d (all 25 °C). In pure water, photolysis DT50 c. 20 d; in natural water, c. 10 d (both 25 °C).

COMMERCIALISATION
History Discovered by Nihon Bayer Agrochem K.K. in 1992 and reported by L. Yasui et al. (Proc. 1997 Br. Crop Prot. Conf. - Weeds, 1, 67). Developed by Bayer AG. Manufacturers Bayer CropScience

APPLICATIONS
Biochemistry Cell division inhibitor. Primary target site may be in fatty acid metabolism. Basis of selectivity is positional; fentrazamide is adsorbed to the surface soil layer and is not touched by the growing point of transplanted rice seedlings. Mode of action Inhibits cell division in root and meristem, causing cessation of growth and distortion of elongated tissue. Uses Control of barnyardgrass (Echinochloa spp.) and annual sedges, from weed pre-emergence up to 3-leaf stage, in rice. Can also be applied at transplanting stage. Formulation types GF; GR; SC; WG. Selected products: 'Lecs' (Bayer CropScience); mixtures: 'Innova GR 75' (+ bensulfuron-methyl) (Nihon Bayer); 'Lecspro' (+ propanil) (Bayer CropScience)

OTHER PRODUCTS
'Bai Tian Jing' (Bayer CropScience); 'Dongsimae' (Bayer CropScience) mixtures: 'Agalia' (+ cyclosulfamuron+ daimuron) (Bayer CropScience, BASF); 'Bigsure' (+ cyclosulfamuron+ daimuron) (Bayer CropScience, BASF); 'Donichi' (+ imazosulfuron+ daimuron) (Bayer CropScience, Sumitomo Chemical Takeda, SDS Biotech KK); 'Doublestar' (+ pyrazosulfuron-ethyl) (Bayer CropScience); 'Inebrite' (+ azimsulfuron+ bensulfuron-methyl) (Bayer CropScience); 'Innova GR 51' (+ bensulfuron-methyl+ daimuron) (Nihon Bayer); 'Innova L SC' (+ bensulfuron-methyl+ daimuron) (Nihon Bayer); 'Innova SC' (+ bensulfuron-methyl) (Nihon Bayer); 'Leading' (+ imazosulfuron) (Nihon Bayer); 'Naegamae' (+ cyclosulfamuron) (Misung); 'Smart' (+ benzobicyclon+ benzofenap) (SDS Biotech KK, Bayer CropScience)

MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for rats >5000 mg/kg. Skin and eye Acute percutaneous LD50 for rats >5000 mg/kg. Not an eye or skin irritant (rabbits); not a skin sensitiser (guinea pigs). Inhalation LC50 for rats >5000 mg/m3. NOEL For rats 10.3, mice 28.0, dogs 0.52 mg/kg b.w. ADI 0.005 mg/kg b.w. (Japan). Other Not mutagenic or teratogenic.

ECOTOXICOLOGY
Birds Acute oral LD50 (14 d) for Japanese quail and bobwhite quail >2000 mg/kg. Fish LC50 (96 h) for carp 3.2, rainbow trout 3.4 mg/l. Daphnia LC50 (24 h) >10 mg/l. Algae EpC50 (72 h) for green algae 6.04 mg/l; no long-term impact on algae, quick recovery. Other aquatic spp. LC50 (96 h) for freshwater shrimps 6.5, Corbicula mussels >100 mg/l. Bees LD50 (topical) for honeybees >150 mg/bee. Worms LC50 (14 d) for Eisenia foetida >1000 mg/kg dry substrate. Other beneficial spp. NOEC for silkworms 100 ppm.

ENVIRONMENTAL FATE
Animals The main pathway of biotransformation proceeded via hydrolytic cleavage of the parent compound. Plants Metabolism was investigated in rice plants under paddy conditions; no parent compound was detected in any plant fraction. Soil/Environment Under paddy soil conditions, fentrazamide was rapidly eliminated from the water phase and thoroughly degraded and mineralised in the submerged soils. In field and laboratory trials under paddy conditions, the calculated half-lives were in the range of a few days and several weeks, respy. Based on Koc values, fentrazamide can be classified as immobile.