Pheromones and Semiochemicals of Oryzaephilus surinamensis (Coleoptera: Silvanidae), the Sawtoothed grain beetle

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Semiochemicals of Oryzaephilus surinamensis, the Sawtoothed grain beetle

Phylum:	Arthropoda
Subphylum:	Uniramia
Class:	Insecta
Order:	Coleoptera
Family:	Silvanidae
Subfamily:	Silvaninae
Genus:	Oryzaephilus
Tribe:
Author:	Linnaeus

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Semiochemical(s):

Hoetling S

2015

Org. Lett.

17:

5004

cucujolide XI

�Relative ratio of the component�

�(*) indicates that compound is active�

A �Category of the chemical signal

A -	Attractant
Al -	Allomone
K -	Kairomone
P -	Pheromone
Sy -	Synomone�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

Germany

Hoetling S

2014

Chem. Eur. J.

20:

3183

cucujolide X

�Relative ratio of the component�

�(*) indicates that compound is active�

A �Category of the chemical signal

A -	Attractant
Al -	Allomone
K -	Kairomone
P -	Pheromone
Sy -	Synomone�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

Germany

R-cucujolide V

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

Collins LE

2007

J. Stored Prod. Res.

43:

E2-9Ald

�Relative ratio of the component�

�(*) indicates that compound is active�

A �Category of the chemical signal

A -	Attractant
Al -	Allomone
K -	Kairomone
P -	Pheromone
Sy -	Synomone�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

4-ethylacetophenone

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

Pierce AM

1991b

J. Chem. Ecol.

17:

581

delta1-octen-3-ol

�Relative ratio of the component�

�(*) indicates that compound is active�

K �Category of the chemical signal

A -	Attractant
Al -	Allomone
K -	Kairomone
P -	Pheromone
Sy -	Synomone�

H �Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

3me-4OH

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

delta1-8-3Kt

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

octan-3-ol

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

8-3Kt

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

2-phenylethanol

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

ethyl alcohol

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

White PR

1989

J. Chem. Ecol.

15:

999

cucujolide IV

4.4 �Relative ratio of the component�

�(*) indicates that compound is active�

P �Category of the chemical signal

A -	Attractant
Al -	Allomone
K -	Kairomone
P -	Pheromone
Sy -	Synomone�

M �Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

Agg. pheromone

cucujolide IX

1 �Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

cucujolide V

2 �Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

delta1-octen-3-ol

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

8-3Kt

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

9Ald

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

Pierce AM

1987

J. Chem. Ecol.

13:

1525

R-cucujolide IV

�Relative ratio of the component�

�(*) indicates that compound is active�

P �Category of the chemical signal

A -	Attractant
Al -	Allomone
K -	Kairomone
P -	Pheromone
Sy -	Synomone�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

Agg. pheromone

cucujolide V

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

cucujolide IX

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

cucujolide III

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

Oehlschlager AC

1987

J. Chem. Ecol.

13:

1543

R-cucujolide IV

�Relative ratio of the component�

�(*) indicates that compound is active�

P �Category of the chemical signal

A -	Attractant
Al -	Allomone
K -	Kairomone
P -	Pheromone
Sy -	Synomone�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

Agg. pheromone

R-cucujolide V

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

Stubbs MR

1985

J. Chem. Ecol.

11:

565

acetic acid

�Relative ratio of the component�

�(*) indicates that compound is active�

K �Category of the chemical signal

A -	Attractant
Al -	Allomone
K -	Kairomone
P -	Pheromone
Sy -	Synomone�

H �Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

isobutyric acid

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

4Acid

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

2me-4Acid

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

caproic acid

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

Pierce AM

1985

J. Agric. Food Chem.

33:

848

cucujolide IV

�Relative ratio of the component�

�(*) indicates that compound is active�

P �Category of the chemical signal

A -	Attractant
Al -	Allomone
K -	Kairomone
P -	Pheromone
Sy -	Synomone�

M �Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

Agg. pheromone

cucujolide IX

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

cucujolide V

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

Mikolajczak KL

1984

J. Chem. Ecol.

10:

301

E2-9Ald

�Relative ratio of the component�

�(*) indicates that compound is active�

A �Category of the chemical signal

A -	Attractant
Al -	Allomone
K -	Kairomone
P -	Pheromone
Sy -	Synomone�

M&F �Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

E2E4-9Ald

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

6Ald

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

7Ald

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

8Ald

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

E2-7Ald

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

furfural

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

3Ald

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

formaldehyde

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

O'Donnell

1983

J. Chem. Ecol.

357

3Ald

�Relative ratio of the component�

�(*) indicates that compound is active�

A �Category of the chemical signal

A -	Attractant
Al -	Allomone
K -	Kairomone
P -	Pheromone
Sy -	Synomone�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

Reference(s):

Ho�tling, S., Bittner, C., Tamm, M., Da�hn, S., Collatz, J., Steidle, J. L. M., and Schulz, S. 2015. Identification of a grain beetle macrolide pheromone and its synthesis by ring-closing metathesis using a terminal alkyne. Org. Lett. 17:5004-5007.

Ho�tling, S., Haberlag, B., Tamm, M., Collatz, J., Mack, P., Steidle, J. L. M., Vences, M., and Schulz, S. 2014. Identification and synthesis of macrolide pheromones of the grain beetle Oryzaephilus surinamensis and the frog Spinomantis aglavei. Chem. Eur. J. 20:3183-3191.

Collins, L.E., Bryning, G.P., Wakefield, M.E., Chambers, J., and Cox, P.D. 2007. Progress towards a multi-species lure: identification of components of food volatiles as attractants for three storage beetles. J. Stored Prod. Res. 43:53-63.

Pierce, A.M., Pierce, H.D., Jr., Borden, J.H., and Oehlschlager, A.C. 1991b. Fungal volatiles: semiochemicals for stored-product beetles (Coleoptera: Cucujidae). J. Chem. Ecol. 17:581-597.

White, P.R., Chambers, J., Walter, C.M., Wilkins, J.P.G., and Millar, J.G. 1989. Saw-toothed grain beetle Oryzaephilus surinamensis (L.) (Coleoptera: Silvanidae). Collection, identification, and bioassay of attractive volatiles from beetles and oats. J. Chem. Ecol. 15:999-1013.

Oehlschlager, A.C., King, G.G.S., Pierce, H.D., Jr., Pierce, A.M., Slessor, K.N., Millar, J.G., and Borden, J.H. 1987. Chirality of macrolide pheromones of grain beetles in the genera Oryzaephilus and Cryptolestes and its implications for species specificity. J. Chem. Ecol. 13:1543-1554.

Pierce, A.M., Pierce, H.D., Jr., Oehlschlager, A.C., Czyzewska, E., and Borden, J.H. 1987. Influence of pheromone chirality on response by Oryzaephilus surinamensis and Oryzaephilus mercator (Coleoptera: Cucujidae). J. Chem. Ecol. 13:1525-1542.

Pierce, A.M., Pierce, H.D., Jr., Oehlschlager, A.C., and Borden, J.H. 1985. Macrolide aggregation pheromones in Oryzaephilus surinamensis and Oryzaephilus mercator (Coleoptera: Cucujidae). J. Agric. Food Chem. 33:848-852.

Stubbs, M.R., Chambers, J., Schofield, S.B., and Wilkins, J.P.G. 1985. Attractancy to Oryzaephilus surinamensis (L.) of volatile materials isolated from vacuum distillate of heat-treated carobs. J. Chem. Ecol. 11:565-581.

Mikolajczak, K.L., Zilkowski, B.W., Smith, C.R., Jr., and Burkholder, W.E. 1984. Volatile food attractants for Oryzaephilus surinamensis (L.) from oats. J. Chem. Ecol. 10:301-309.

O'Donnell, M.J., Chambers, J., and McFarland, S.M. 1983. Attractancy to Oryzaephilus surinamensis (L.), saw-toothed grain beetle, of extracts of carobs, some triglycerides and related compounds. J. Chem. Ecol. 9:357-374.

Citation: El-Sayed AM 2024. The Pherobase: Database of Pheromones and Semiochemicals. <http://www.pherobase.com>.
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