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guazatine acetates
Editor	I.G. Ferris
Entity code	GUACE
CAS registry No.	115044-19-4
Family	Alkylamines
Functions	Fungicide, Bird Repellent, Antifeedant
Chemical name	acetates of a mixture of the reaction products from polyamines [comprising mainly octamethylenediamine, iminodi(octamethylene)diamine, octamethylenebis(imino-octamethylene)diamine, and carbamonitrile (IUPAC) (EN)
Synonyms
Trade names	Panoctine (KenoGard); Panolil (KenoGard); Radam (KenoGard); Kenopel (KenoGard, Pennwalt)
Other names
Last updated	20/2/2009

Fate
Under laboratory conditions, soil degradation as measured by ¹⁴CO₂ evolution was slow with an extrapolated DT₅₀ half-life of 400-600 days. The use of ¹⁴C-octyl or -guanidino groups indicated that degradation was via dequanidations, which was considered the rate limiting step.
Guazatine was strongly adsorbed to all soil types irrespectively organic matter content. Adsorption increased with increasing clay content and cation exchange capacity.
Up to 1.3% of applied ¹⁴C-Guazatine was detected in leachate following application equivalent to 1.2 kg ai/ha.

Toxicology
Mammals: Acute oral LD50 for rats ca. 227-300 mg/kg. Acute percutaneous LD50 for rats >1000, rabbits 1176 mg/kg. In 2-year feeding trials, no-effect level for rats and dogs was 200 mg/kg diet. Non-teratogenic and non-carcinogenic (rats).

Detection

Sampling

Methods
Guazatine has been determined by a total residue method based on conversion to the
corresponding triamine, bis(8-amino-octyl)amine, which also occurs as a metabolite. Modern analytical methods using octane-1,8-diyldiguanidine (GG), one of the main components of guazatine, as a marker are more specific.

MRLs

Uses
Seed treatment for control of Septoria nodorum, Tilletia caries, Fusarium spp., and Helminthosporium spp. in cereals and maize (also acts as a bird repellent). Control of Pyricularia oryzae (rice blast) in rice, Cercospora spp. in groundnuts and soybean, Septoria spp. in wheat, and pineapple disease in sugar cane. Also used as a post-harvest dip for seed potatoes, citrus fruit, and pineapples.

Notes
Guazatine acetates are derivatives of guazatine [108173-90-6]. The approved common name guazatine was originally defined as applying to N,N‴-(iminodi-8,1-octanediyl)bis[guanidine] (BSI used the name guanoctine from 1970-1972). It is now known that the material marketed commercially is a reaction mixture that is produced by the amidination of technical iminodi(octamethylene)diamine, commercial guazatine containes numerous guanidines, in which the amino and imino groups of the polyamine chain form part, and polyamines; many of these bases are fungicidal. A replacement common name, iminoctadine [13516-27-3] has been established for 1,1′-(iminodioctamethylene)diguanidine. (Pesticide Manual, 1994).

Bibliography
UK PSD guazatine report 1992 (http://www.pesticides.gov.uk/PSD_PDFs/Evaluations/053_guazatine.pdf)
JMPR guazatine report 1997 http://www.fao.org/ag/AGP/AGPP/Pesticid/JMPR/Download/97_rep/Report97.pdf

Mode of action
Fungicide with bird-repellent properties. Guazatine acetates affect the membrane function of fungi.

Ecotoxicology
Birds: LD₅₀ for Japanese quail 0.638 ml/kg bw equivalent to 429 mg ai/kg bw. LD₅₀ for pigeons 82 mg/kg with emetic effect.
Fish: LC₅₀ for Oncorhynchus mykiss was 23 m/l 48 h and 19 mg/l 96 h.
Aquatic invertebrates: The acute oral toxicity of guazatine acetate to Daphnia magna was about 0.1 mg/l and NOEC 3 µg/l.
Bees: Not toxic to bees when used as directed.
Other organisms: LC₅₀ (14 d) for worms > 1000 mg/kg.

Plant metabolism & residues
When ¹⁴C-guazatine was applied to the leaf surface or the fruit of apples (brushing with 0.05 or 0.1 kg ai/hl) its translocation was extremely limited. Autoradiography showed no observable movement in the leaves or fruit.
The uptake of ¹⁴C-guazatine by winter wheat was low from 1.05 g/kg seed treatments. At the first harvest the mean uptake into the plants was 0.07% of the applied radioactivity, equivalent to 0.18 mg/kg as guazatine. At maturity the ¹⁴C in the plants still represented 0.07% of the applied radioactivity but because of growth dilution the concentrations in the plants from the treated and control plots were similar and all mean values were less than 0.05 mg guazatine equivalents/kg.

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