Tebufenozide is an

insecticide Insecticides are substances used to kill insects. They include ovicides and larvicides used against insect eggs and larvae, respectively. Insecticides are used in agriculture, medicine, industry and by consumers. Insecticides are claimed to b ...

that acts as a

molting hormone Ecdysone is a prohormone of the major insect molting hormone 20-hydroxyecdysone, which is secreted from the prothoracic glands. It is of steroidal structure. Insect molting hormones (ecdysone and its homologues) are generally called ecdysteroids. ...

. It is an

agonist An agonist is a chemical that activates a receptor to produce a biological response. Receptors are cellular proteins whose activation causes the cell to modify what it is currently doing. In contrast, an antagonist blocks the action of the ago ...

of the

ecdysone receptor The ecdysone receptor is a nuclear receptor found in arthropods, where it controls development and contributes to other processes such as reproduction. The receptor is a non-covalent heterodimer of two proteins, the EcR protein and ultraspiracle ...

that causes premature molting in larvae. It is primarily used against

caterpillar Caterpillars ( ) are the larval stage of members of the order Lepidoptera (the insect order comprising butterflies and moths). As with most common names, the application of the word is arbitrary, since the larvae of sawflies (suborder Sym ...

pests. Because it has high selectivity for the targeted pests and low toxicity otherwise, the company that discovered tebufenozide,

Rohm and Haas Rohm and Haas Company is a manufacturer of specialty chemicals for end use markets such as building and construction, electronic devices, packaging, household and personal care products. Headquartered in Philadelphia, the company is organized i ...

, was given a Presidential Green Chemistry Award for its development. It has been characterised, along with RH-2485, as a bisacylhydrazine.Dhadialla TS, Carlson GR, Le DP: "New Insecticides with ecdysteroidal and juvenile hormone activity"
in ''Annual Review of Entomology'' 43(1):545-69 · February 1998 Its environmental

half-life Half-life (symbol ) is the time required for a quantity (of substance) to reduce to half of its initial value. The term is commonly used in nuclear physics to describe how quickly unstable atoms undergo radioactive decay or how long stable ato ...

varies according to where it is released and under what conditions, but can be said to be on the order of months. It has been used for "an insect growth regulator, to control leaf-eating

insects Insects (from Latin ') are pancrustacean hexapod invertebrates of the class Insecta. They are the largest group within the arthropod phylum. Insects have a chitinous exoskeleton, a three-part body (head, thorax and abdomen), three pairs of j ...

that cause damage or death in

trees In botany, a tree is a perennial plant with an elongated stem, or trunk, usually supporting branches and leaves. In some usages, the definition of a tree may be narrower, including only woody plants with secondary growth, plants that are u ...

. Tebufenozide is the active ingredient in"

Bayer Bayer AG (, commonly pronounced ; ) is a German multinational corporation, multinational pharmaceutical and biotechnology company and one of the largest pharmaceutical companies in the world. Headquartered in Leverkusen, Bayer's areas of busi ...

's MIMIC "formulation, which controls forest defoliator pests such as

gypsy moth ''Lymantria dispar'', also known as the gypsy moth or the spongy moth, is a species of moth in the family Erebidae. ''Lymantria dispar'' is subdivided into several subspecies, with subspecies such as ''L. d. dispar'' and ''L. d. japonica'' bei ...

tent caterpillar Tent caterpillars are moderately sized caterpillars, or moth larvae, belonging to the genus ''Malacosoma'' in the family Lasiocampidae. Twenty-six species have been described, six of which occur in North America and the rest in Eurasia. Some s ...

s, budworms,

tussock moth The Lymantriinae (formerly called the Lymantriidae) are a subfamily of moths of the family Erebidae. The taxon was erected by George Hampson in 1893. Many of its component species are referred to as "tussock moths" of one sort or another. The cat ...

s and

cabbage looper The cabbage looper (''Trichoplusia ni'') is a medium-sized moth in the family Noctuidae, a family commonly referred to as owlet moths. Its common name comes from its preferred host plants and distinctive crawling behavior. Cruciferous vegetable ...

. These are all pests of the order

Lepidoptera Lepidoptera ( ) is an order (biology), order of insects that includes butterfly, butterflies and moths (both are called lepidopterans). About 180,000 species of the Lepidoptera are described, in 126 Family (biology), families and 46 Taxonomic r ...

." It has been used against the sugarcane borer, although the population grows immunity. In California, the substance was used chiefly for crops of

head lettuce Lettuce (''Lactuca sativa'') is an annual plant of the family Asteraceae. It is most often grown as a leaf vegetable, but sometimes for its stem and seeds. Lettuce is most often used for salads, although it is also seen in other kinds of food ...

celery Celery (''Apium graveolens'') is a marshland plant in the family Apiaceae that has been cultivated as a vegetable since antiquity. Celery has a long fibrous stalk tapering into leaves. Depending on location and cultivar, either its stalks, lea ...

raspberries The raspberry is the edible fruit of a multitude of plant species in the genus ''Rubus'' of the rose family, most of which are in the subgenus '' Idaeobatus''. The name also applies to these plants themselves. Raspberries are perennial with w ...

cauliflower Cauliflower is one of several vegetables in the species ''Brassica oleracea'' in the genus ''Brassica'', which is in the Brassicaceae (or mustard) family. It is an annual plant that reproduces by seed. Typically, only the head is eaten – the ...

, and

tomatoes The tomato is the edible Berry (botany), berry of the plant ''Solanum lycopersicum'', commonly known as the tomato plant. The species originated in western South America, Mexico, and Central America. The Mexican Nahuatl word gave rise to th ...

for processing. A 1994 study conducted by the

Canadian Forest Service The Canadian Forest Service (CFS; french: Service canadien des forêts) is a sector of the Canadian government department of Natural Resources Canada. Part of the federal government since 1899, the CFS is a science-based policy organization responsi ...

in laboratory conditions concluded that the substance was very stable in

acidic In computer science, ACID ( atomicity, consistency, isolation, durability) is a set of properties of database transactions intended to guarantee data validity despite errors, power failures, and other mishaps. In the context of databases, a sequ ...

and neutral buffers at 20 °C, hydrolytic degradation was dependent on pH and temperature, sunlight photodegradation was observed at a slower rate than ultraviolet photodegradation, and that

microbial metabolism Microbial metabolism is the means by which a microbe obtains the energy and nutrients (e.g. carbon) it needs to live and reproduce. Microbes use many different types of metabolic strategies and species can often be differentiated from each other ...

and photolysis are the two main degradative routes for tebufenozide in natural aquatic systems.tandfonline.com: "Degradation kinetics of tebufenozide in model aquatic systems under controlled laboratory conditions"
''Journal of Environmental Science and Health, Part B: Pesticides, Food Contaminants, and Agricultural Wastes'', Volume 29, 1994 - Issue 6, Pages 1081-1104 The final degradation products of tebufenozide are various

alcohols In chemistry, an alcohol is a type of organic compound that carries at least one hydroxyl () functional group bound to a saturated carbon atom. The term ''alcohol'' originally referred to the primary alcohol ethanol (ethyl alcohol), which is ...

carboxylic acids In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an R-group. The general formula of a carboxylic acid is or , with R referring to the alkyl, alkenyl, aryl, or other group. Carboxylic ...

and

ketone In organic chemistry, a ketone is a functional group with the structure R–C(=O)–R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group –C(=O)– (which contains a carbon-oxygen double bo ...

s of low toxicity.Roberts TR et al, "Metabolic Pathways of Agrochemicals: Part 2: Insecticides and Fungicides"
p820 (Royal Society of Chemistry, 2007)

Derivatives

Furan tebufenozide

In 2010, laboratory tests and field tests were performed on furan tebufenozide. The results were on the order of one hundred days.Cong Guo et al
"Degradation of furan tebufenozide in laboratory and field trials"
in ''Science China Chemistry'' August 2010, Volume 53, Issue 8, pp 1818–1824

References

{{insecticides Insecticides Hydrazides Tert-butyl compounds