The United States of America As Represented by the Secretary of

University of Iowa Research Foundation

Biotechnology Research and Development Corporation

James B Gloer

Patrick F Dowd

Donald T Wicklow

Jodi A Laakso

Mark R TePaske

Ali A Alfatafta

Gail M Staub

Florecita S deGuzman

Gilbert N Belofsky

Brad L Rinderknecht

Carbonarins A, B, C, D, E, F, G, and H have been isolated from the sclerotia of the fungus Aspergillus carbonarius. The carbonarius are effective for controlling Coleopteran and Lepidopteran insects. The carbonarins have the structure: ##STR1## wherein: R.sub.1 is a hydrogen atom or a hydroxy group; R.sub.2 is a hydrogen atom or a methoxy group; R.sub.3 is a hydrogen atom or a naphthopyrone group; and X is an oxygen atom or an NH group.

Carbonarin antiinsectan metabolites

Carbonarins A, B, C, D, E, F, G, and H have been isolated from the sclerotia of the fungus Aspergillus carbonarius. The carbonarins are effective for controlling Coleopteran and Lepidopteran insects. The carbonarins have the structure: ##STR1## wherein: R.sub.1 is a hydrogen atom or a hydroxy group; R.sub.2 is a hydrogen atom or a methoxy group; R.sub.3 is a hydrogen atom or a naphthopyrone group; and X is an oxygen atom or an NH group.

Shearinines A, B and C, and 21-Isopentenylpaxilline are ascostromatal metabolites of the fungus Eupenicillium shearii. These indole alkaloid compounds are effective for controlling Coleopteran and Lepidopteran insects and the fall armyworm, Spodoptera frugiperda.

Indole antiinsectan metabolites from the ascostromata of Eupenicillium

Sulpinine C, secopenitrem B and 10-oxo-11,33-dihydropenitrem B indole compounds have been isolated from the sclerotia of the fungi Aspergillus sulphureus. Aflatrem B has been isolated from the sclerotia of the fungi Aspergillus flavus, and 14-hydroxypaspalinine and 14-(N,N-dimethylvalyloxy)paspalinine have been isolated from the sclerotia of the fungi Aspergillus nomius. The indole compounds are effective for controlling Coleopteran and Lepidopteran insects.

Indole antiinsectan metabolites

Diketopiperazine compounds designated N-methylepiamauromine, epiamauromine and cycloechinulin have been isolated from the sclerotia of the fungi Aspergillus ochraceus. The compounds are effective for controlling Coleopteran and Lepidopteran insects. The compounds have the structures: ##STR1## wherein: R is a hydrogen atom or a methyl group, such that the compound formed when R is a hydrogen atom is designated epiamauromine and the compound formed when R is a methyl group is designated N-methylepiamauromine; and cycloechinulin has the structure: ##STR2##

N-methylepiamauromine, epiamauromine and cycloechinulin antiinsectan

A novel N-methoxy-2-pyridone designated leporin A has been isolated from the sclerotia of the fungus, Aspergillus leporis. Leporin A is characterized by the structural formula ##STR1## and is effective for controlling Lepidopteran insect pests.

Leporin A, an antiinsectan fungal metabolite

A diketopiperazine compound designated cycloechinulin has been isolated from the sclerotia of the fungi Aspergillus ochraceus. The compound is effective for controlling Coleopteran and Lepidopteran insects. Cycloechinulin has the structure: ##STR1##

Cycloechinulin antiinsectan metabolite

A tetrahydroquinoline alkaloid compound named 'aspernomine' has been isolated from the sclerotia of the fungus Aspergillus nomius. Aspernomine has the structure: ##STR1## and is effective for controlling Lepidopteran insects.

Aspernomine, an antiinsectan metabolite

Indole compounds named 'sulphinine' and 'secopenitrem' have been isolated from the sclerotia of from fungi Aspergillus sulphureus. An indole compound named 'aflatrem B' has been isolated from the sclerotia of the fungi Aspergillus flavus. The compounds are effective for controlling Coleopteran and Lepidopteran insects.

Sulpinine, secopenitrem B and aflatrem B antiinsectan metabolites

Indole diterpene compounds named 'radarin' have been isolated from the sclerotia of the fungus Aspergillus sulphureus. The radarins are effective for controlling Lepidopteran insects, and have the structures: ##STR1## wherein the compound formed when R is a hydroxyl group is designated radarin A and the compound formed when R is a hydrogen atom is designated radarin C; and ##STR2## wherein the compound formed when R is a hydrogen atom is designated radarin D and the compound formed when R is a hydroxyl group is designated radarin B.

Radarin antiinsectan metabolites

A novel indole diterpene compound named 'nominine' has been isolated from the sclerotia of the fungus, Aspergillus nomius. Nominine is characterized by the structural formula ##STR1## and is effective for controlling Lepidopteran and Coleopteran insect pests.

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James B Gloer