Porphyric Insecticides - Chlorophyll Biosynthesis and Technological Applications - page 428

Table 18.14 Effects of ALA, and substituted pyridiniums, 2-oxypyridines and pyrroles on Proto
accumulation and larval death in T . ni

Proto content
(nmol/100 mg
protein)

Larval mortality after
6 days in the greenhouse
(%) Treatment a Entry Template

1.4abc b 1 Pyridinium Control 1.7a

2 ALA 2.2bcd 3.3a

3 1-(3-Sulfopropyl)

pyridinium hydroxide

2.4 cd 0.0a

4 Above + ALA 4.4de 0.0a

5 Bis-N-methylacridinium

nitrate

5.6e 21.7b

6 Above + ALA 10.9f 65.0c

1,1 0 -Diethyl-2,4 0 -cyanine
iodide

7 58.1 h 75.0c

8 Above + ALA 87.0 h 85.0 cd

1,1 0 -Diethyl-4,-
4 0 -carbocyanine iodide

9 3.5a 96.7d

10 Above + ALA 21.9 g 93.3d

11 Oxypyridine 1,5-Isoquinolinediol 1.0a 1.7a

12 Above + ALA 3.7de 33.0bb

13 Isocarbostyril 1.2ab 1.7a

14 Above + ALA 16.3 fg 86.7 cd

15 Pyrrole 4,5,6,7-Tetrahydroindole 1.3abc 1.7a

16 Above + ALA 2.6 cd 1.7a

17 ter-Butyl 4-acetyl-3,5-

dimethyl-2-pyrrole-
carboxylate

1.3abc 0.0a

18 Above + ALA 2.7d 20.4b

19 3-Ethyl-2-methyl-4,5,6,7-

tetrahydroindole-4-one

0.9a 0.0a

20 Above + ALA 10.0f 83.3 cd

Correlation coefficient 0.76

Level of significance 0.1 %

Adapted from Gut and Rebeiz Gut et al. ( 1993 )
a Treatment consisted of control diet lacking any added ALA or modulator, diet containing 4 mM
ALA, 3 mMmodulator or 4 mM ALA + 3 mMmodulator, in a randomized complete block design
with three replicates. Percent larval death was arcsine transformed prior to statistical analysis
b Means followed by the same letter within a column are not significantly different at the 5 % level
of significance

ALA and modulator were required for activity (Tables 18.14 and 18.15 ).
8-Hydroxyquinoline and the NO 2 substituted analog, 8-hydroxy-5-nitroquinoline
in which the hydrogen atom at position 5 of the macrocycle was replaced by an
NO 2 group was inactive (Fig. 18.7 , Table 18.15 , # 3-6). When the nitro group was

replaced by a sulfonyl group, as in 8-hydroxyquinoline-5-sulfonic acid, substantial
insecticidal activity was observed (Fig. 18.7 ; Table 18.15 , # 9, 10). Further substi-
tution with a 4-sulfo-1-naphtylazo group at position 7 of the macrocycle as in
8-hydroxy-7-(4-sulfo-1-naphthylazo)-5-quinoline-sulfonic acid resulted in a minor