Flucycloxuron
CAS No. 113036-88-7
 
 

ACTIVITY: Herbicide, Acaricide, Insecticide (benzoylurea)

CAS NAME: N-[[[4-[[[[(4-chlorophenyl)cyclopropylmethylene]amino]oxy]methyl]phenyl]amino]carbonyl]-2,6-difluorobenzamide

Structure:

Regulatory Information
(only comprehensive for the US)
US EPA Registered: No 
US EPA PC Code: 129027 
(Old US EPA PC Code: 225100)
European Commission:

Not allowed to be used as an active ingredient after July 25, 2003.

Registered use in
(includes only a limited list of countries)

Hungary
EU: Netherlands
 
Other Information
Molecular Formula: C25H20Cl F2 N3O3 
Manufacturers: Crompton Corporation 
Other Names: Andalin 2L
DU 319722,
PH 70-23,
UBI-A1335
 
Of special interest:
PAN Data 
See also Flucycloxuron, E-isomer
November 26, 2002 - European Commission: Flucycloxuron is one of 320 pesticides to be withdrawn in July 2003. Some 320 substances used in plant protection products (PPPs) - including insecticides, fungicides and herbicides - are to be withdrawn from the market by 25 July 2003 as part of the European Commission's new approach to the evaluation of active substances in plant protection products. This aims to improve safeguards to ensure that all such products in use are safe for the environment and human health. Users, wholesalers and retailers of plant protection products will need to be aware of whether the products they use or sell are likely to be withdrawn, so as to prevent them being left with stocks of unusable material. Those concerned should contact their national authority to check the authorisation status for any particular product. The Regulation (ní 2076/2002 of 20 November 2002), with the list of the 320 substances, has now been published in the Offical Journal. Ref: MIDDAY EXPRESS. News from the Press and Communication Service's midday briefing. 
Glossary of Pesticide Chemicals, October 2001. A listing of pesticides subject to analysis of residues in foods and feeds by the US Food and Drug Administration. 

Adverse Effects:

As of Dec 2003: No data available


http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=pubmed&cmd=Retrieve&dopt=AbstractPlus&list_uids=16786494&query_hl=1&itool=pubmed_docsum

Pest Manag Sci. 2006 Aug;62(8):752-8.

Hazards and uptake of chitin synthesis inhibitors in bumblebees Bombus terrestris.

Mommaerts V, Sterk G, Smagghe G.

Department of Biology, Faculty of Sciences, Free University of Brussels, Brussels, Belgium.

This research project examined the potential hazards of a major class of insect growth regulators (IGRs) to survival, reproduction and larval growth in bumblebees Bombus terrestris L. Eight chitin synthesis inhibitors (CSIs) were tested: buprofezin, cyromazine, diflubenzuron, flucycloxuron, flufenoxuron, lufenuron, novaluron and teflubenzuron. These different IGRs, which are important in the control of pest insects in greenhouses, were applied via three different routes of exposure under laboratory conditions: dermal contact, and orally via the drinking of sugar/water and via pollen. The compounds were tested at their respective maximum field recommended concentrations (MFRC) and also in dose-response assays to calculate LC(50) values. In general, none of the CSIs showed acute worker toxicity. However, there was a dramatic reduction in brood production, especially after oral treatment with pollen and sugar/water. Conspicuously, egg fertility was reduced in all treatments with diflubenzuron and teflubenzuron. In addition to egg mortality, the worker bumblebees removed larvae from the treated nest, and in most cases these individuals were dead first-second instars. Under a binocular microscope, such larvae showed an abnormally formed cuticle leading to mechanical weakness and death. In another series of experiments using (14)C-diflubenzuron and (14)C-flufenoxuron, cuticular penetration in workers was studied for a better understanding of the differences in toxicity. With (14)C-diflubenzuron, transovarial transport and accumulation in the deposited eggs supported the strong reproductive effects. Overall, the present results suggest that CSIs should be applied with caution in combination with bumblebees. The compatibility of each compound to be used in combination with B. terrestris is discussed in relation to calculated LC(50) values, routes of uptake and effects.

PMID: 16786494 [PubMed - indexed for MEDLINE]

NOTE from FAN: 6 of the 8 pesticides tested are fluorinated: diflubenzuron, flucycloxuron, flufenoxuron, lufenuron, novaluron and teflubenzuron

Abstracts from TOXNET

Behavior of benzoylurea insecticide teflubenzuron and flucycloxuron in soil environment.
Authors: KIM T-H, KIM J-E
Author Address: Dep. Agric. Chem., Kyungpook National University, Taegu 702-701, KOR.
Source: JOURNAL OF THE KOREAN AGRICULTURAL CHEMICAL SOCIETY; 36 (6). 1993. 510-516.
Abstract:
BIOSIS COPYRIGHT: BIOL ABS. The degradation and leaching pattern of benzoylurea insecticide teflubenzuron and flucycloxuron in soil environment and their effect on urease activity were investigated. The half-life of teflubenzuron was 39.1 days and 20.9 days in Chilgok and Ansim soil of nonsterilized condition, respectively, and that of flucycloxuron was 102.3 days and 50.1 days. Teflubenzuron and flucycloxuron were degraded more rapidly in Ansim soil with rich organic matter than Chilgok soil, and were degraded very slowly under sterilized condition. Their degradation seemed to be mainly mediated by microorganisms in soil. Teflubenzuron was degraded 63.2 days and 29.2 days faster than flucycloxuron under nonsterilized condition of Chilgok and Ansim soil. The inhibition of urease by the pesticides in two kinds of soil was strongly affected (37.6 42.4%) in the early stage of their treatment but hardly affected or increased a little after 120 days. The teflubenzuron and flucycloxuron remained in the

Biological activity of flucycloxuron, a novel benzoylphenylurea derivative, on Tenebrio molitor: Comparison with diflubenzuron and triflumuron.
Authors: SOLTANI N, CHEBIRA S, DELBECQUE JP, DELACHAMBRE J
Author Address: Dep. de Biologie Animale, Universite de Annaba, BP 12, 23000 Annaba, ALG.
Source: EXPERIENTIA (BASEL); 49 (12). 1993. 1088-1091.
Abstract:
BIOSIS COPYRIGHT: BIOL ABS. Flucycloxuron, a novel benzoylphenylurea (BPU) derivative, exhibited insecticidal activity when injected into newly ecdysed pupae of Tenebrio molitor. Mortality occurs because of defective adult ecdysis. Treatment caused a reduction in both cuticle thickness and incorporation of 14C-labelled precursor into chitin, although it had no significant effect on the protein synthesis. The potencies of other BPU compounds as inhibitors of chitin biosynthesis have been examined and results showed that diflubenzuron was less effective than either flucycloxuron or triflumuron.

BEE POISONING HAZARD PROSSER 1990-1991
Authors: MAYER DF, LUNDEN JD, HUSFLOEN MR
Source: BURDITT, A. K. JR. (ED.). INSECTICIDE & ACARICIDE TESTS, VOL. 18. II+405P. ENTOMOLOGICAL SOCIETY OF AMERICA: LANHAM, MARYLAND, USA.; 0 (0). 1993. 361.

 
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