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Chemical Identification
Common Name
Cyprodinil
中文通用名
嘧菌环胺
IUPAC
4-cyclopropyl-6-methyl-N-phenylpyrimidin-2-amine
CAS
4-cyclopropyl-6-methyl-N-phenyl-2-pyrimidinamine
CAS No.
121552-61-2
Molecular Formula
C14H15N3
Molecular Structure
Category
Activity
Fungicide.
Cyprodinil controls ascomycete and deuteromycete fungi. It is a systemic fungicide with preventative and curative activity and is particularly useful for early-season applications. The product has residual activity of up to 10 days in apples. Following foliar application, cyprodinil rapidly penetrates the leaves and therefore has good rainfastness. It is distributed throughout leaf tissue and is translocated acropetally in the xylem. The product’s activity is best exploited at lower a temperature. Syngenta recommends that it is applied at GS 30-32 in cereals and from early-season to late-flowering in apples. In all cases, the company recommends limited number of sprays or in mixtures with a fungicide with different mode of action to prevent the build-up of resistance.
In field trials, no phytotoxicity to target crops has been observed with the exception of sweet cherries and some tomato varieties where crop tolerance might be critical. Syngenta recommends its use in IPM programmes.
CropUse
Crop uses:
cereals, soft fruits, top fruits, stone fruits, pome fruits, almonds, grapes, barley

Wheat

600-750 g ai/ha

Barley

375-600 g ai/ha

Apples

15-37.5 g ai/hl

Premix
Fludioxonil+cyprodinil
Cyprodinil+Tebuconazole
Cyprodinil+Boscalid
Cyprodinil+Thiophanate-methyl
Cyprodinil+Procymidone
Water dispersible granules. Premix Parters: ametryn; anilofos; atrazine; bentazone cyanazine; bromoxynil; bromoxynil propanil; butachlor; carfentrazone-ethyl; carfentrazone-ethyl dicamba mecoprop-P; cinidon-ethyl; clopyralid; clopyralid dicamba; dicamba; dicamba dichlorprop; dicamba fluroxypyr; dicamba MCPA; dicamba mecoprop; dicamba mecoprop MSMA; dicamba mecoprop-P; dicamba mecoprop-P sulfentrazone; dicamba metsulfuron-methyl; dicamba picloram; dicamba quinclorac sulfentrazone; dichlorprop; dichlorprop mecoprop; dichlorprop mecoprop-P; dichlorprop-P; diuron MSMA; fenoxaprop-P-ethyl MCPA; fluroxypyr; fluroxypyr MCPA; gibberellic acid 1-naphthaleneacetic acid; glyphosate; ioxynil; MCPA; MCPA mecoprop; mecoprop; mecoprop-P; metsulfuron-methyl; 1-naphthaleneacetic acid; picloram; piperophos; prometon; propanil; triclopyr;

Type

AI concn

Water-dispersible granule (WG)

75% (w/w)

?

50% (w/w)

Wettable powder (WP)

Physical Properties
Molecular weight:225.3; Physical form:Fine beige powder, with a weak odour. Density:1.21 (20 °C); Melting point:75.9 °C; Vapour pressure:5.1×10-1 mPa (crystal modification A); 4.7×10-1 mPa (crystal modification B) (both 25 °C); Henry constant:6.6×10-3 to 7.2×10-3 Pa m3 mol-1 (calc., depending on crystal modification); Partition coefficient(n-octanol and water):logP = 3.9 (pH 5.0), 4.0 (pH 7.0), 4.0 (pH 9.0) (25 °C); pKa:4.44, weak base; Solubility:In water 20 (pH 5.0), 13 (pH 7.0), 15 ( pH 9.0) (all in mg/l, 25 °C). In ethanol 160, acetone 610, toluene 460, n-hexane 30, n-octanol 160 (all in g/l, 25 °C).; Stability: Hydrolytically stable: DT50 in pH range 4-9 (25 °C) >>1 y. Photolysis DT50 in water 0.4-13.5 d.??Solubility (25°C): in acetone 610 g/l, ethanol 160 g/l, toluene 460 g/l, n-hexane 30 g/l, n-octanol 160 g/l.
Toxicology
Oral: Acute oral LD50 for rats >2000 mg/kg. Percutaneous:Acute percutaneous LD50 for rats >2000 mg/kg. Non-irritant to eyes and skin (rabbits). Skin sensitiser (guinea pigs). Inhalation:LC50 (4 h) for rats >1200 mg/m3 air.?
Environmental Profile
Ecotoxicology: Algae:EbC50 (72 h) for Scenedesmus subspicatus 0.75 mg/l.Bees:LD50 (48 h, oral) >316 μg/bee; LC50 (48 h, contact) >101 mg/bee. Birds:LD50 for mallard ducks and bobwhite quail >2000 mg/kg(quail, mallard). LC50 (8 d) for mallard ducks and bobwhite quail >5200 ppm.Daphnia:LC50 (48 h) 0.033-0.10 mg/l. Fish:LC50(96 h) for rainbow trout 0.98-2.41 mg/l, carp 1.17 mg/l, bluegill sunfish 1.07-2.17 mg/l, sheepshead minnow 1.25 mg/l, catfish 1.03 mg/l. Worms: LC50 (14 d) for Eisenia foetida 192 mg/kg.Other aquatic spp.:EC50 for Lemna gibba 7.71, Mysidopsis spp. 0.008 mg/l.Other beneficial spp.:Harmless to Poecilus cupreus, Episyrphus and mites (IOBC). Environmental fate: Animals:After oral administration, cyprodinil is rapidly absorbed and almost completely eliminated with urine and faeces. Metabolism proceeds by 4-hydroxylation of the phenyl and 5-hydroxylation of the pyrimidine rings, followed by mono- or di-sulfation. Residues Soil:In soil, the compound dissipated with DT50 20-60 d at normal soil humidities and soil temperatures, whereby formation of bound residues represents the major route for dissipation. Plant:In tomatoes, the metabolism of cyprodinil proceeded mainly via hydroxylation of the 6-methyl group of the pyrimidine ring, as well as hydroxylation of the phenyl and pyrimidine rings.
WATER SOLUBILITY: At 25°C: 20 mg/l (pH 5), 13 mg/l (pH 7), 15 mg/l (pH 9) .?

Mallard duck

LD50 >500 mg/kg Virginia quail LD50 >2,000 mg/kg

Bluegill sunfish

LC50 3.2 ppm Bobwhite quail LD50 >2,000 mg/kg

Daphnia magna

LC50 32.8 ppb Rainbow trout [96 hrs] LC50 2.41 ppm

Fathead minnow

NOEC 0.23 ppm Bee [contact] LD50 >101 mg/bee

Mysid shrimp

LC50 8.14 ppb Earthworm LD50 >111 g/kg soil

Skeletonema costatum

EC50 1.97 ppm

Fate in :

The data in the table above are from acute studies.
Cyprodinil is practically non-toxic to birds, small mammals, bees and earthworms. It is moderately toxic to fish and very highly toxic to freshwater and marine invertebrates.

Fate in soil:
The half-life of cyprodinil in soil is 20-60 days; it is only slightly mobile in soil and the risk of contamination of ground water is low.
Fate in aqueous systems:
Cyprodinil is photolysed in water; the half-life is less than 14 days. It is not readily hydrolysed.
The major route of dissipation for cyprodinil in the environment is considered by the US EPA to be aerobic soil metabolism. It is characterised by EPA as 'slightly persistent to persistent' in soil, 'persistent' in sediments and 'moderately persistent to persistent' in water/sediment. Anaerobic soil and water/sediment studies indicated no biotransformation under anaerobic conditions. The product shows strong sorption to soil and low mobility.

Transport Information
Signal Word:CAUTION; Hazard Class:III (Slightly hazardous)

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