Ovipositional Deterrent against Liriomyza trifolii
425
(
1
½
CD OD): 24.8 t (C-3), 35.8 t (C-2), 40.6 t (C-4) and
3
eggs of Liriomyza trifolii within chrysanthemum, celery
and tomato leaves. J. Econ. Entomol., 75, 383–384
(1982).
81.4 s (COOH). LC-MS (APCI-positive) m=z: 104
þ
þ
M þ Hꢁ , 122 ½M þ H þ H Oꢁ and 145 ½M þ H þ
2
þ
3) Tokumaru, S., and Abe, Y., Interspecific hybridization
between Liriomyza sativae Blanchard and L. trifolii
H2O þ Naꢁ .
(
4
Burgess) (Diptera: Agromyzidae). Appl. Entomol. Zool.,
0, 551–555 (2005).
(
2S,4R)-4-Hydroxy-1-methyl-2-pyrrolidine carboxylic
2
2
ꢃ
acid (2). Amorphous solid. ½ꢂꢁ
¼ ꢂ44:1 (c ¼ 1:2,
D
4
)
Saito, T., Outbreak of Liriomyza trifolii Burgess in Japan
and its control. Plant Protection (in Japanese with
English abstract), 47, 123–124 (1993).
1
H2O). H-NMR (D2O) ꢃ: 2.07 (1H, dt, J ¼ 4:4, 12.4 Hz,
H-3a), 2.30 (1H, dd, J ¼ 7:6, 12.4 Hz, H-3b), 2.87 (3H,
s, N-Me), 3.01 (1H, br-d, J ¼ 13:2 Hz, H-5a), 3.77 (1H,
dd, J ¼ 4:4, 13.2 Hz, H-5b), 4.01 (1H, br-t, J ¼ 7:6 Hz,
5) Murphy, S. T., and Lasalle, J., Balancing biological
control strategies in the IPM of New World invasive
Liriomyza leafminers in field vegetable crops. Biocont.
News Info., 20, 91N–104N (1999).
13
H-2), 4.45 (1H, d, J ¼ 2:0 Hz, H-4); C-NMR (D2O) ꢃ:
3
7
8.9 t (C-3), 43.8 q (N-Me), 63.3 t (C-5), 70.1 d (C-4),
0.7 d (C-2) and 173.4 s (COOH). LC-MS (APCI-
6
)
Saito, T., Oishi, T., Isawa, A., and Ikeda, F., Effect of
temperature, photoperiod, and host plant on development
and oviposition of Liriomyza trifolii (Burgess). Jpn. J.
Appl. Entomol. Zool. (in Japanese with English abstract),
þ
þ
positive) m=z: 146 ½M þ Hꢁ , 168 ½M þ Naꢁ and 184
þ
½
M þ Kꢁ .
3
9, 127–134 (1995).
Preparation of (2S,4R)-4-hydroxy-1-methyl-2-pyrro-
7
)
Isawa, A., Saito, T., and Ikeda, F., Effect of host plant
and temperature on reproduction of American serpentine
leafminer, Liriomyza trifolii (Burgess). Jpn. J. Appl.
Entomol. Zool. (in Japanese with English abstract), 43,
41–48 (1999).
lidine carboxylic acid (2). To a solution of L-hydrox-
yproline (1 g, 7.63 mmol) in water (5 ml) were added
acetic acid (8.5 ml) and 37% aqueous formaldehyde
1
4)
(
0.66 ml, 23.8 mmol).
The resulting mixture was
stirred under H2 atmosphere in the presence of PtO2
8) Tryon, E. H., Poe, S. L., and Cromroy, H. L., Dispersal
of vegetable leafminer onto a transplant production
range. Flo. Entomol., 63, 292–296 (1980).
ꢃ
(
87 mg, 0.383 mmol) at 30 C for 12 h. The catalyst was
filtered away, and the resulting filtrate was evaporated
under reduced pressure. The residue was diluted with
acetone, and the precipitate was isolated by filtration to
give (2S,4R)-4-hydroxy-1-methyl-2-pyrrolidine carbox-
9
)
Kashiwagi, T., Horibata, Y., Mekuria, D. B., Tebayashi,
S., and Kim, C., Ovipositional deterrent in the sweet
pepper, Capsicum annuum, at the mature stage against
Liriomyza trifolii (Burgess). Biosci. Biotechnol. Bio-
chem., 69, 1831–1835 (2005).
2
2
ꢃ
ylic acid (1.02 g, 92%) as a powder. ½ꢂꢁ
¼ ꢂ82:9
D
1
(
c ¼ 1:0, H2O). H-NMR (D2O) ꢃ: 2.08 (1H, dt, J ¼
1
0) Kashiwagi, T., Mikagi, E., Mekuria, D. B., Boru, A. D.,
Tebayashi, S., and Kim, C., Ovipositional deterrent on
mature stage of sweet pepper, Capsicum annuum,
against Liriomyza trifolii (Burgess). Z. Naturf., 60C,
739–742 (2005).
4
3
5
:0, 14.0 Hz, H-3a), 2.32 (1H, dd, J ¼ 7:2, 14.0 Hz, H-
b), 2.88 (3H, s, N-Me), 3.02 (1H, br-d, J ¼ 13:2 Hz, H-
a), 3.78 (1H, dd, J ¼ 4:0, 13.2 Hz, H-5b), 4.03 (1H,
br-t, J ¼ 8:0 Hz, H-2), 4.46 (1H, d, J ¼ 2:0 Hz, H-4).
1
3
1
1
1
1
1) Masahito, W., Hideyuki, H., Kentaro, M., Kiyoto, K.,
Takumi, T., Hana, H., and Fangyu, W., Metabolic
pathways of ꢁ-aminobutyric acid (GABA). Osaka Ika
Daigaku Zasshi, 60, 1–16 (2001).
C-NMR (D O) ꢃ: 38.9 t (C-3), 43.8 q (N-Me), 63.3 t
2
(
C-5), 70.1 d (C-4), 70.7 d (C-2) and 173.4 s (COOH).
Cytidine or 4-amino-1-ꢀ-D-ribofuranosyl-2(1H)-pyri-
2) Suk-Heung, O., Yeon-Jong, M., and Chan-Ho, O.,
2
2
ꢃ
midinone (3). White powder. ½ꢂꢁ
¼ þ26:9 (c ¼ 1:2,
D
ꢁ
-Aminobutyric acid (GABA) content of selected un-
cooked foods. Nutraceuticals and Food, 8, 75–78
2003).
1
H2O). H-NMR (D2O) ꢃ: 3.62 (1H, d, J ¼ 12:4 Hz, H-
0
0
0
5
4
5
7
(
(
a), 3.74 (1H, d, J ¼ 12:8 Hz, H-5 b), 3.94 (1H, s, H-
(
0
0
), 4.01 (1H, s, H-3 ), 4.12 (1H, d, J ¼ 3:2 Hz, H-2 ),
3) Shelp, B. J., Van, C., Owen, R., and Bown, A. W.,
Gamma aminobutyrate, from intellectual curiosity to
practical pest control. Can. J. Bot., 81, 1045–1048
(2003).
4) Kawamoto, I., Shimoji, Y., Kanno, O., Kojima, K.,
Ishikawa, K., Matuyama, E., Ashida, Y., Shibayama, T.,
Fukuoka, T., and Ohya, S., Synthesis and structure-
activity relationships of novel parenteral carbapenems,
CS-023 (R-115685) and related compounds containing
an amidine moiety. J. Antibiotics, 56, 565–579 (2003).
0
.71 (1H, br-s, H-1 ), 5.86 (1H, d, J ¼ 5:2 Hz, H-5),
13
.65 (1H, d, J ¼ 7:2 Hz, H-6). C-NMR (D2O): 61.3 t
0
0
0
0
0
C-5 ), 69.8 d (C-3 ), 74.5 d (C-2 ), 84.4 d (C-4 ), 90.9 d
C-1 ), 96.8 d (C-5), 142.2 d (C-6), 158.1 s (C-2) and
1
66.6 s (C-4). LC-MS (APCI-positive) m=z: 244
þ
þ
þ
½
M þ Hꢁ , 262 ½M þ H þ H2Oꢁ and 282 ½M þ Kꢁ .
ꢂ
LC-MS (APCI-negative) m=z: 242 ½M ꢂ Hꢁ .
References
15) Sciuto, S., Chillemi, R., Piattelli, M., and Impellizzeri,
G., The identification of 4-hydroxy-N-methylproline in
the red alga Chondria coerulescens:spectral information.
Phytochemistry, 22, 2311–2312 (1983).
16) Nakayama, T., Honda, K., Omura, H., and Hayashi, N.,
Oviposition stimulants for the tropical swallowtail
butterfly, Papilio polytes, feeding on a rutaceous plant,
Toddalia asiatica. J. Chem. Ecol., 29, 1621–1634
1
)
)
Dogimont, C., Bordat, D., Pages, C., Bissot, N., and
Pitrat, M., One dominant gene conferring the resistance
to the leafminer, Liriomyza trifolii (Burgess) Diptera:
Agramyzidae in melon (Cucumis melo L.). Euphytica,
105, 63–67 (1999).
Parrella, M. P., and Robb, K. L., Technique for staining
2