Fungicide

FRAC  Y; multi-site: inorganic

NOMENCLATURE

Common name oxine-copper (BSI, JMAF); oxine copper (E-ISO); oxine-Cu (alternative E-ISO, (m) F-ISO); oxine-cuivre ((m) F-ISO); oxyquinoléate de cuivre (France); copper 8-quinolinolate (Canada)

IUPAC name bis(quinolin-8-olato-O,N)copper; cupric 8-quinolinoxide 

Chemical Abstracts name bis(8-quinolinato-N1,O8)copper 

Other names copper oxyquinolate  CAS RN [10380-28-6]  EEC no. 233-84-19  Development codes Ro 17-0099/000 (Dr Maag); CGA 281881 (Ciba-Geigy) 

PHYSICAL CHEMISTRY

Mol. wt. 351.9  M.f. C18H12CuN2O2  Form Olive-green powder.  M.p. Decomposes above 270 ºC  V.p. 4.6 ´ 10-5 mPa (25 ºC) (EEC A.4)  KOW logP = 2.46 (distilled water, 25 ºC).  Henry 2.31 ´ 10-4 Pa m3 mol-1 (calc.)  S.g./density 1.63 (20 °C)  Solubility In water 0.07 mg/l (pH 7, 25 ºC). In methanol 116, n-hexane <0.01 (both in mg/l, 25 ºC).  Stability DT50 60-96 h (pH 7.0). Chemically inert. Stable to u.v. light. 

COMMERCIALISATION

History The fungicidal properties of this complex of copper with quinolin-8-ol, the latter known by the trivial name oxine, reported by D. Powell (Phytopathology, 1946, 36, 572).  Manufacturers Syngenta; Tomono

APPLICATIONS

Mode of action Non-systemic, protective fungicide.  Uses Seed treatment for control of glume blotch, bunt, and snow mould of wheat; Cercospora, Phoma, and Pythium spp. in beet; Alternaria and Botrytis spp. in flax; Alternaria and Phoma spp. in oilseed rape; Sclerotinia sclerotiorum in sunflowers; and leaf spot on beans and peas; application rates range from 20-100 g/100 kg seed; also for control of leaf spot on celery; and scab and canker on pome fruit. Also used for sealing wounds and pruning cuts on trees, and for treatment of fruit- and potato-handling equipment.  Phytotoxicity Non-phytotoxic when used as directed. Not to be used on copper-sensitive plants.  Formulation types DS; PA; SC; WP.  Selected tradenames: 'Okishindo' (Tomono); 'Quinolate' (Syngenta); 'Quinondo' (Agro-Kanesho)

OTHER TRADENAMES

'Seed Guard' (Vapco) Discontinued names mixtures: 'Austral' * (+ anthraquinone+ tefluthrin) (seed treatment) (La Quinoléine); 'Kasumin Bordeaux' * (+ copper oxychloride+ kasugamycin hydrochloride hydrate) (Hokko)

ANALYSIS

Product analysis by reaction with sulfuric acid and standard methods for estimation of copper (AOAC Methods, 1984, 6.015-6.016; CIPAC Handbook, 1970, 1, 226; ibid., 1983, 1B, 1915, 1918).  

MAMMALIAN TOXICOLOGY

IARC ref. 15  class 3  Oral Acute oral LD50 for rats 4700, mice 9000 mg/kg.  Skin and eye Acute percutaneous LD50 for rats >2000 mg/kg. Non-irritating to skin; irritating to eyes (rabbits).  Inhalation LC50 for rats 150 mg/m3 air.  NOEL (2 y) for rats 2, dogs 5 mg/kg diet; (80 w) for mice 400 mg/kg diet.  ADI 0.02 mg/kg.  Other Non-carcinogenic, non-mutagenic and non-teratogenic.  Toxicity class WHO (a.i.) III (Table 5); EPA (formulation) I (water-base); II, III (petroleum solvent-base) 

ECOTOXICOLOGY

Birds LD50 (8 d) for bobwhite quail 618, mallard ducks >2000 mg/kg. LC50 (8 d) for bobwhite quail 3428, mallard ducks >2000 mg/kg.  Fish LC50 (96 h) for bluegill sunfish 21.6, rainbow trout 8.94 mg/l.  Daphnia LC50 (48 h) 177 mg/l.  Algae EC50 (5 d) 2.20-15.4 mg/l.  Bees Non-toxic to bees. 

ENVIRONMENTAL FATE