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Organotin compounds in agriculture since 1980. Part 2

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Applied Organomuroliic Chemistru (1987) I 331-346
i!; Loripnand Group U K Ltd 1987
REVIEW
Organotin compounds in agriculture since 1980
Part 2." Acaricidal, antifeedant, chemosterilant
and insecticidal properties
Alan J Crowe
International Tin Research Institute, Kingston Lane, Uxbridge, Middlesex UB8 3PJ, UK
Received 7 October 1986 Accepted 12 January 1987
The object of this review paper is to provide a
guide to agrochemical research involving organotin
compounds which has been performed since 1980.
The information is presented in a tabular form and
is divided into four main sections as indicated by
the title. Each section is then subdivided to cover
the various commercial organotin compounds. A
final subsection lists investigations involving novel
compounds. An additional section covers the
effects of organotin agrochemicals on non-target
organisms. A table of the contents has been provided to enable ease of reference. Acaricidal, antifeedant, chemosterilant and insecticidal properties
are covered here. Fungicidal, bactericidal and
herbicidal aspects are covered in Part 1.
Keywords: Agrochemicals, organotin, triphenyltin, tricyclohexyltin, trineophyltin, acaricide, antifeedant, chemosterilant, insecticide, non-target
organisms
CONTENTS
Part 2-Acaricidal, antifeedant,
chemosterilant and insecticidal
properties
Introduction
Section 1 Acaricidal properties
Table 1.1 Full and common names of the mites
included in Section 1
Table 1.2 Acaricidal investigations involving
cyhexatin
Table 1.3 Acaricidal investigations involving
fenbutatin oxide
Table 1.4 Acaricidal investigations involving
azocyclotin
Table 1.5 Acaricidal investigations involving
novel organotin compounds
*Part 1: Crowe A J Appl. Organomel. Chem., 1987, 1: 143.
Section 2
Table 2.1
Table 2.2
Table 2.2.1
Table 2.2.2
Table 2.3
Table 2.4
Table 2.4.1
Table 2.4.2
Table 2.4.3
Section 3
Table 3.1
Table 3.2
Table 3.3
Antifeedant, chemosterilant and
insecticidal properties
Insects mentioned in the antifeedant,
chemosterilant and insecticidal Tables
Antifeedant properties
Antifeedant investigations involving
triphenyltin compounds, Ph,SnX
Antifeedant investigations involving
other commercial organotins
Chemosterilant properties
Insecticidal properties
Insecticidal investigations involving
triphenyltin compounds, Ph,SnX
Insecticidal investigations involving
other commercial organotins
Insecticidal investigations involving
novel organotin compounds
Effects of organotin compounds on
biological control agents and
beneficial organisms
Effects on mite predators
Effects on entomopathogenic fungi
Effects on other biological control
agents and beneficial organisms
References
INTRODUCTION
A general introduction to the actual and potential agrochemical uses of organotin compounds
was given in Part 1,* which in addition covered
the recent research into their fungicidal, bactericidal and herbicidal properties.
Mites are small, eight-legged, acarine creatures,
some species of which are phytophagous (plant
feeding) and are a constant problem in green-
332
Organotin compounds in agriculture since 1980. Part 2
houses, nurseries, and in deciduous and citrus
fruit orchards.’ These mites live exclusively on
plant sap and can cause great mechanical
damage to leaf tissues on plants. The complete
egg-to-adult cycle takes about 14 days and an
adult female lives for about three weeks during
which time she lays approxirnatcly 120 eggs,
which hatch within five days. Thus large populations of these mites can rapidly arise.
Three organotin acaricides are currently commercially available, tricyclohexyltin hydroxide
(Cyhcxatin: Plictran); bis(trineophy1tin)oxide
(Fenbutatin oxide: Vendex or Torque) and tricyclohexyltin- 1,2,4-triazole (Azocyclotin: Peropal).
All three are highly effective in the control of
phytophagous mites, and cyhexatin in particular
is widely used (for structures see Part I). These
three compounds are active against mites which
are resistant to conventiona1 acaricides such as
organophosphates,’ but show little effect on
predacious mites and other bencticial insects,
including the honey
The organotin acaricides tend to behave as
contact poisons and give highly lethal effects to
Table 1.1 Full and common names of the mites included in
Section 1
Full name
Common name
Compound”
Acuphyllu theae
Acarus siro
Aceria litchii
Aculus schlectendali
G1vnydta.p.r destructor
I’ununpchus citri
Panonychus ulmi
Paracalacarus podocarpi
Phylloroptruta oleivora
Psoroptes cuniculi
Psoroptes o vis
Rhizoglyphus robini
Sarcoptes
Tarsonemm pullidus
Tctranychus arabicus
Tctranychus cinnabarinus
Tetranychus gloveri
Tctranychus urticae
Pink
Stored product
Erinose
Apple rust
Stored product
Citrus red
Red
Rust
Citrus rust
Ear canker
Common scabies
Bulb
Itch
Strawberry
Green
Carmine
Glover’s spider
Two-spotted
spider
Hawthorn
Stored product
Stored product
C
F
C
Tetranychur viennensis
Tyrophagous iongior
Tyrophagous putrescentiae
C, F
F
N
A, C, F
C, F
A, C, F
C
C
C
C
C
A, F
N
c, F
c, F, N
C
F
F
“A, Azocyclotin (Table 1.4); C, Cyhexatin (Tablc 1.2); F,
Fenbutatin oxide (Table 1.3); N, Novel organotin (Table 1.5).
all motile stages, including adult mites. The
quiescent stages of development are usually less
sensitive to these acaricides, while eggs display
the greatest re~istance.’.~
These acaricides, which are compatible with
other pesticide^,^ are usually applied as wettable
powders which are readily dispersed in water and
can therefore be used in conventional sprayers.’
After application they are resistant to the effects
of rain’ and since they do not exhibit any
systemic action their residues rcmain on the
surface of the treated
Formulations containing low concentrations of the active ingredients produce long effective lifetimes, which may
be enhanced, if necessary, by repeat applications.
In recent years the use of broad spectrum
pesticides has come under considerable criticism
due to their lack of selectivity, which means that
both beneficiai and non-target insects are also
adversely affected. Also such pesticides are often
persistent in the environment and thus remain
toxic for long periods. In addition, excessive use
has led to a build-up of resistance to the toxic
effect of these chemicals. Research is now being
directed towards the development of compounds
which control insect pest populations by more
indirect means such as disruption of normal
maturation processes (e.g. juvenile hormone analogues) or disruption of behaviour patterns by
modifying sensory input (e.g. pheromones). Two
other
approaches
are
antifeedants
and
chemosterilants.
An antifeedant produces a cessation of feeding
by preventing the insect from recognizing the
normal host plant gustatory stimulus by inhibiting taste receptors.6 Thus the insect pest starves
to death or is eaten by predators.
During field trials to assess the fungicidal activity of triphenyltin acetate (Fentin acetate:
Brestan) it was noticed that insect feeding was
prevented on treated f01iage.~A subsequent laboratory study showed that the feeding of larvae of
the cotton leaf worm Spodoptera littoralis on
sugar beet leaves was inhibited by sublethal
amounts of both fentin acetate and triphenyltin
hydroxide (Fentin hydroxide: Duter).’ As a direct
result of this work the effects of these and other
organotins on a variety of surface-feeding insects
were in~estigated.~,
The main advantages of antifeedants over conventional techniques is that beneticiaI and nontarget insects are not affected because (i) they do
not eat the treated crop, and (ii) sub-lethal concentrations of the compounds are used. Thus
Organotin compounds in agriculture since 1980. Part 2
antifeedants may be utilized in integrated pest
control methods involving biological control
agents, such as predatory insects. In addition,
antifeedants act faster than conventional insecticides to restrict feeding damage, since an insect
may continue to feed during the time it takes for
an insecticide to kill it.
Organotins do not exhibit systemic activity
and so arc unable to. protect plants as antifeedants against sucking insects and internal leaf
eaters.'j
A chemosterilant is a chemical which interferes
with the reproductive cycle of an insect. The first
detailed report of organotins displaying this
propcrty was by Kenager," who demonstrated
that various types of insects showed diminished
or no reproduction after feeding on triphenyltin
derivatives. The majority of the subsequent
studies have concentrated on the common housefly (Musca dornestica) but a number of other
species have also been studied and promising
results
The triphenyltins appear to produce a reduction in both egg-laying and in the percentage of
larvae which hatch out. This effect, however,
appears to be reversible with time. An additional
effect of these compounds was to prolong the
larval-pupal duration. Thus in an integrated pest
control system the triphenyltins would enable
increased predation of the larvae to occur.
Both antifeedants and chemosterilants are preferred forms of insect control since sub-lethal
concentrations are used. In addition, the fact that
doses which are lethal to the pest insects are
often tolerated by non-target species suggests that
such compounds would be suitable for commercialization and it may well be that in futurc years
organotin compounds will become available for
use in one or both of these applications.
The insecticidal properties of various triorganotin compounds have been known for many
years and yet to date none of them has reached
practical use. One of the main reasons for this is
that the most potent organotin insecticides tend
to be the trimethyltins which also possess high
mammalian toxicity, which precludes their use."
Other effective organotins, with lower mammalian toxicities, such as the tributyltin derivatives, are phytotoxic and so their use would be
limited. Even the triphenyltins mentioned previously display phytotoxicity to certain crops,
although this may be reduced by formulation.2
However, the investigation of their insecticidal
properties has continued and a suitable organotin
insecticide may yet be found.
333
The main advantages of the organotin agrochemicals are considered to be their low phytotoxicity; compatibility with other pesticides;
ability to undergo environmental degradation;
and a generally low toxicity to non-target organisms. This latter property is being investigated
with rcspect to integrated pest control, where
biological control agents, such as mite predators
and entomopathogenic fungi or bacteria, are used
in combination with organotins. Research in this
area is collated in Section 3.
SECTION 1 ACARlClDAL PROPERTIES
The full and common names of the mites included in this scction are listed in Table 1.1. The
acaricidal investigations of the commercial organotins appear in Tables 1.2-1.4 and are listed
alphabetically with regard to the crop on which
they were tcsted. The studies involving novel
organotins, Table 1.5, are divided into tricyclohexyltin derivatives (1.5.1); anionic complexes
(1.5.2) and miscellaneous compounds (1.5.3).
SECTION 2 ANTIFEEDANT,
CHEMOSTERILANT AND
INSECTICIDAL PROPERTIES
Table 2.1 gives the names of all the insects on
which these studies have been performed and
indicates in which Table they appear.
Antifeedant properties arc listed, alphabetically
with respect to the insect on which the tests were
performed, in Table 2.2, which is divided into
two subsections: triphenyltins (2.2.1) and other
commercial organotins (2.2.2).
Chemosterilant investigations are listed in
Table 2.3.
Insecticidal studies are given in Table 2.4
which is divided into three subsections: triphenyltin compounds (2.4.1) other commercially
available organotins (2.4.2) and novel organotins
(2.4.3).
SECTION 3 EFFECTS O F ORGANOTIN
COMPOUNDS ON BIOLOGICAL
CONTROL AGENTS A N D BENEFICIAL
ORGAN I S M S
In Tables 3.1, mite predators, and 3.2, entomopathogenic fungi, the biological control agents
are listed alphabetically. The third and final
Table of this section includes a variety of other
non-target species.
Table 1.2 Acaricidal investigations involving Cyhexatin
Comments
Reference
A . schlerkrendalr
A . schlechtendali
Applied as a 25% wettable powder at a rate of 280gna-I gave control
Was only effective when applied post-blossom
A . schlechtendali
P. ulmi
P. uimi
T. urticae
Controlled both mites. Best time to apply was found to be pink flower bud
stage
A single spray controlled the mite 95-98%
Application of 1.8g per tree in spray volumes ranging from 0.225 to
9.0 dm3 per tree gave complete control
Controlled mites by Y G l O O % and protected trees for 1.5-2.0 months
Under field conditions was highly effective
A four-spray system incorporating a cyhexatin-sumicidin mixture
controlled the mite, as well as codling moth, and resulted in greatly
increased fruit yields
Superior oil in early spring and cyhexatin wcrc most commonly used
control materials in 18/19 commercial orchards in Ohio, during 197911980
respcctively
Cyhexatin was the most predominantly used acaricide in 36 Pennsylvanian
commercial orchards during 1978/1979
At 0.1% gave 100% kill
Spraying with 200dm3 0.3% cyhexatin per ha controlled mites by ca 96%.
Also prevented oviposition of the mite and the bollworm
Treatments of 0.4 and O.8lb per 100gal. gave good control of both
species"
Gave 6@80% control; other chemicals were superior
Was used in first spray in combination with rubigan to combat Oidum and
mitcs
I .6 k g ha-' gave completc control of organophosphorus-resistant mites
A single spray with 0.2% kept mites below damaging level during an entire
season
At 0.05% gave promising results in minimizing infestation
Gave partial control after foliar spraying
Under field conditions was highly effective
12
13
14
Crop/Product Mite
T.urtieae
T. urticae
T. riennemis
Mites
Mites
Cattle
Cotton
P. ovis
T.urticae
Eggplant
T. gluveri
T. urticae
R. rubini
Mites
Gladiolus
Grape
Grape
Intensive
gardens
Litchi
Orange
Pear
Pig
Podocarpu.r
macrophyllus
Rabbit
Roses
P. ulmi
P. ulmi
A . litchii
P. oleivora
T.urticae
Sarcoptes
P. podocarpi
P.cuniculi
T. urticae
Strawberry
T.urticae
Strawberry
Strawberry
T. urticae
T. pallidus
Tea
A . iheae
Vine
T. urticae
Vine
Vine
Vine
T. urticae
T. urticap
T. urlicae
One or two sprayings with 0.1% controlled the mite in 34-month-old pigs
Population of this important pest in nursery and landscape culture in
Florida was reduced to i 1 mite per leaf after a single application
At 0.01% gave 100% kill
The control of powdery mildew or of the mite was not affected when
applied in combination with Bayleton, neither was thc mixture phytotoxic
in the greenhousc
Of 23 pesticides lested cyhexatin consistently gave the best results
A two-year greenhouse study showed cyhexatin to be an effective miticide
Dipping transplants in 0.2% solution controlled the mite and increased
transplant survival rate
Spraying twice as a 50% wettable powder at 500-1000gha-1 gave control
for eight weeks
Controlled mite 100% as determined 20 days post treatment. Was
espccially effective due to its high ovicidal activity
Under field conditions was highly effective
Three New Caledonian strains were found to be susceptible to cyhexatin
Concentrations of 0.0254).5% were preferred for controlling mobile stages
and periodic application did not cause resistance
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
18
31
32
22
33
34
35
36
37
38
18
39
40
aImperial measures were given in the original reference. For conversion to SI units, I Ib=0.454kg; 100gal. =455dm3.
334
335
Organotin compounds in agriculture since 1980. Part 2
Table 1.3 Acaricidal investigations involving Fenbutatin oxide
Crop
Mite
Comments
Reference
Apple
Controlled both mites. The best time of application was the pink flower
bud stage
Concentrations of 750 1100g ha- I gave good control of all three species
14
Apple
A . schlechtendali
P. ulmi
A. schlechtenduli
P. ulmi
T urticae
7: urticae
17
Beans
7: urticur
Eggplant
Grapefruit
T gloveri
T. urticur
P. oleivoru
Mites were controlled by 90-lOOP: and trees were protected for 1.5-2.0
months
In combination with 2-sec-butylphenyl-N-methylcarbamate,
curbed the
mites
Applications o f 1 and 2 Ib per 100 gal. gave good control of both mites"
Irish shamrock
T. urticae
Orange
Pear
Podocarpus
rnucrophyllus
Soya beans
Strawberries
Vine
Wheat
T. urticae
P. podocarpi
T. arabicus
7. urlicae
T. urticae
A . siro
G . destrucror
T. longior
T. putrescentiae
T. urticae
Applied at 10 week intervals, 2.0lbacre-' gave full season mite
suppression"
Formulations containing 3 M 0 g d m - 3 controlled both mites and eggs for
I 2 weeks in greenhouses
A slight incrcasc in the photosynthesis rate of leaves was observed after
treatment
Was less effective than cyhexatin
The population of this important mite pest in nursery and landscape
culture in Florida was reduced to < 1 mite per leaf by a single application
Mite numbers were reduced
Was usually effective but cyhexatin performed better
Was less effective than cyhexatin
At 20ppm was unable to give complete mortality to any of these stored
product mites
Found to be faster-acting than cyhexatin and azocyclotin. It killed more
than 50% of the mites in 24 h
41
42
24
43
44
45
18
32
46
34
18
47
48
"Imperial measures were given in the original reference. For conversion to S1 units, 1 Ib = 0.454 kg; 100gal. = 455 dm3,
1 acre 0.405 ha.
Table 1.4 Acaricidal investigations involving Azocyclotin
Crop
Mite
Comments
P. ulmi
T. arubicus
Excellent control was exhibited in greenhouse experiments
Produced a reduction in the mite population
Reference
~~~~~
Apple
Soya beans
49
46
Organotin compounds in agriculture since 1980. Part 2
336
Table 1.5
Acaticidal investigations involving novel organotin compounds
1.5.1
Tricyclo hexyltin derivatives, Cy Sn X
,
X
Comments
Referencc
__ .-
~.
.
Y
-
R
Y =o,s
-0.
R
- 0 C O .C(Me,)(CH,),CH,
-0CO. (CHMe,)CH . C6H,. CMe,-4
-OCO . CH,S
3
'N i'NH E t (and similar)
Acaricidal and insecticidal activity was claimed
50
28 such compounds were effective miticides at S00ppni
A suspension containing 250 ppm completely controlled
7: urticae
Useful as a miticide for oranges
51
52
At 100ppm gave 100% kill of T urticae adults after 2 days
54
Was effective against 7: urticae
The orlho derivative at 0.15 or 0 . 2 n m 0 l d m - ~on bean resulted in
loo?: mortality of 7: urcicur after 48 h
No phytotoxicity was observed at 2 4 t 1 m o l d m - ~
At 0.0075, 0.01 and 0.01257< on bean gave l000/;, mortality of T
urticae after 48 h. No phytotoxicity was observed
55
56
53
N 3
NHEt
- 0 C O . C6H5
-0CO. C,H,. NH,
-0S0,.
1.5.2
NH,
57
Tricyclohexyltin mercaptides showed acaricidal properties
58
Comments
Referencc
kill of 7: cinnuburinus larvae was achieved with a
25 ppm treatment
Controlled 7: urricae and 7: cinnabarinus at SO and 25 ppm
respectively on bean plants
Controlled T urticue on beans within eight days
Behaved as a simultaneous fungicide and miticide. Controlled 7:
urticae on bean and downy mildew on grape
59
Anionic complexes
Complex
LMe,NCH,CH,Br]
and analogues
' [Cy,SnCIBr]
[Me,NCH,CH,Br]+[Ph,SnCIBr]
and similar
Bis(dicyclohexylneophy1tin)oxide
Tricyclopentyltin hydroxide
Trioctyltin fluoride
~
-
At 250ppm controlled P. cilri on mandarin for 30 days and was not
phytotoxic
60
61
62
63
337
Organotin compounds in agriculture since 1980. Part 2
Table 2.1 Insects mentioned in the antifeedant, chemostcrilant and insecticidal tables
Insect
Table
Aedes aegypti
Anthonornous grandis
Aphis fabae
Aphra.rtaria pertinutue
Attagenus megatoma
Callo.rohruchus chinensis
Carpocapsa
Ceratitis rapitata
Chilo sicppressalis
Cholndovskya viridana
Chrotogonous trachypterus
Cotton boll worm
Diacrisia ubliqua
Epilachnu vigin/ioc/opunciu~u
Grcen peach aphids
Helinrhis
Keiferiu Iyrnpersirellu
Lasioderma sericorne
Leptinotarsa deremlinmta
Mindarus cibietinris
Musca dnrnesiico
Pupilio demoleus
Periplanatu americanu
Plusiu pepunis
Pluiella xylostella
Polyphagot arsonem~~s
Porthervia di.vpar
Prodenia
Scirpophaga incertulas
Spodoptera litioralis
Tcrmite
Tetranychus chinensi,s
Tetrunychu.r urticcw
Triboliuni castcineuni
Tribolium confusurn
Triclioplusia ni
Trogoderma gmnarium
2.4
2.4
2.4
2.4
2.4
2.4
2.4
2.3. 2.4
2.4
2.4
2.2, 2.4
2.3
2.2
2.2
2.4
2.4
2.4
2.4
2.2
2.4
2.3. 2.4
2.2
2.4
2.2
2.4
2.4
2.2
2.4
2.2
2.2, 2.4
2.4
2.4
2.3
2.4
2.2, 2.4
2.4
2.4
3 38
Organotin compounds in agriculture since 1980. Part 2
Table 2.2 Antifeedant properties
2.2.1
Antifeedant investigations involving triphenyltin compounds, Ph,SnX
X
Insect
Comments
Reference
OAc
Chrotogonus trachypterus
(surface grasshopper)
Diacrisia obliqua
At 0.4”/, was lethal and loo”/, mortality was recorded within 48 h
Significant protection was afforded at 0.025-0.2x
Treatment with 0.09% Ph,SnCI provided the maximum protection for
sugar beet foliage. Both compounds increased top, roo1 and sucrose
yield
The hydroxide was superior to the acetate and was most effective at
0.05%
Feeding of final-instar grubs was inhibited by 0.0125-0.1% treatments
(at 0.2-0.4”/:the acetate was 100% lethal)
In laboratory studies feeding was reduced by 95%, while in small field
plots the larval densities were reduced. Beetle populations on potato
were significantly reduced in a commercial-scale experiment and fewer
insecticide applications were required for control where the hydroxide
was used regularly
Triphenyltin chloride ranked first in both antifeedant (against larvae)
properties and field persistence on plants and was followed by the
acetate
The feeding activity of first-instar larvae was inhibited 5&70”/;; by
applications of 0.0241%. The percentage of deaths due to starvation
increased with higher concentrations
The chloride was the most active. Larval growth retardation was
believed to be due to antifeedant effect
64
C1
OH
OAc
OH
OAc
Diacrisia ohliqua
OH
Epilachna
tiigintioctopunctata
Leptinotarra
decemlineata
(Colorado beetle)
CI
OAc
Papilio demoleus
and Plusia pepanis
OH
Scir pophaga
incertulas
CI
CY
(2-OHCy)
Tribolium
confusum
(Confused flour beetle)
2.2.2
65
66
67
68
69
70
71
Antifeedant investigations involving other commercial oiganotins
Compound
Insect
Comments
Reference
Cyhexatin
Porthetria dispar
(Gypsy moth)
Caterpillar development was retarded
72
An antifeedant effect was observed when applied to cotton leaves
73
Azocyclotin Spodoptera littoralis
(cotton leafworm)
Table 2.3 Chemosterilant properties
Compound
Insect
Comments
Fentin hydroxide
Ceratitis capitata
(Mediterranean fruit fly)
Fentin acetate
Fentin hydroxide
Musca dornestica
(housefly)
Cyhexatin
Cyhexatin
7: urticae (spider mite)
and cotton boll worm
7: urticae
A promising sterilizing agent of female flies treated as larvae;
2&400 ppm reduced the number of daily deposited eggs,
decreased the hatchability percentage of eggs and reduced the
reproductive potential
At 0.1% level the process of vitellogenesis was inhibited and
ovaries were only in second phase of development at 5-10days,
whereas controls had mature eggs present
Prevented oviposition of both
Fentin hydroxide
L urticae
Gave 100% control. Was especially effective due to its high
ovicidal activity
Caused suppression of the reproductive potential of female
mites
Reference
74, 75
76
23
38
77
Organotin compounds in agriculture since 1980. Part 2
339
Table 2.4 Insecticidal properties
Insecticidal investigations involving triphenyltin compounds, Ph,SnX
2.4.1
X
Insect
Comments
Reference
CI
Callosobruchus
chinensis
(stored product pest)
Both compounds caused >90”/, mortality. An increase in
rate of germination of red gram ( c m j a n ) seeds from 60 to
2 70% and a decrease in seed loss weight from 19.2 to S 5%
were observed
Showed high larvicidal activity. Prolonged larval duration,
reduced full grown larval weight, reduced weight of pupae
treated as larvae, decreased the percentage emergence of
adults treated as larvae, and also reduced the life span of
these emerged adults
At 0.47; was lethal and 100% mortality was recorded within
48 h
78
-
OH
OH
Ceratitus capitata
(Mediterranean fruit fly)
OAc
Chrotogonous
trachypterus
(surface grasshopper)
Keiferia lycopersicella
(tomato pinworm)
OH
Termite
CI
2.4.2
Survival and development of larvae were reduced in
laboratory experiments. While in the field, there was a
reduction of foliage and fruit damage on tomato plants
A piece of pine board coated with a PVC formulation
containing the chloride was not attacked during 1 yr in a
termite nest. Hence potential use as electric cable insulation
and building material
75
64
79
80
Insecticidal investigations involving other commercial organolins
Compound
Insect
Cyhexatin
Aphrastasia pectinutue and
Cholodovskya oiridana (insect
pests of Canadian spruce)
Cyhexatin
Carpocapsa
(codling moth)
Cyhexatin
Cyhexatin
Weliothis and
Prodenia
(moths)
Keiferia lycopersicella
(tomato pinworm)
Comments
_
_
~
At 0.8:~; gave 98-100% control of both species
~
19
In combination with permethrin gave good control of both
and doubled the cotton yield
82
Survival and development of larvae were reduced in
laboratory experiments. While in the field, reduction of
foliage and fruit damage on tomato plants was seen
79
83
Mindarus abietinus
(balsam twig aphid)
Only slight toxicity was shown
Fenbutatin oxide
Aedes aegypti
Insecticidal properties are claimed
Use as a slow-release larvicide. At 20 and lO0ppb LC,, for
larvae occurred 5 2 days. At 200 ppb LCs0 occurred in 7
days. Larval development was partially blocked at 20 ppm
and totally blocked at 2 100ppm
A composition containing TBTP >4, TBTCI > 2, TBTO > 1,
and chlordene > 3 parts is a termite control agent and
rodenticide
Tributyltin
chloride,
oxide and phthalate
(mosquito)
rermite
81
A four-spray system incorporating a mixture of cyhexatin
and sumicidin controlled the moth as well as mites and
resulted in greatly increased apple yields
Cyhexatin
Tributyltin
fluoride
Reference
42
84,R5
86
Organotin compounds in agriculture since 1980. Part 2
340
Table 2.4.3 Insecticidal investigations involving novcl organotin compounds
2.4.3.1
Insecticidal inbestigations involving tricylohexyltin compounds. Cy,SnX
X
Reference
Comments
~
-0CO
(CR'CHR") (synthetic polymers)
POCO. R
-0C'O C',H,
-S(CH,), ,CH, (and similar mercaptides)
2.4.3.2
~~
~
~~~~~~~~~~~~
4 t 0.05 w t ", gave 1002, kill of houseflies after 3 h whereas
azocyclotin gave only 407; kill
87
At SOpprn gave 7@100x, kill of Spodopteru littorafis larvae
88
For example, Cy,Sn methacrylate was impregnated on to a filter
paper disc which was then placed into a jar containing 100
termites. all of which died within 48 h
Materials forinulated from synthetic resins or natural or synthetic
rubbers and tricyclohexyltin compounds were not attacked by
termites ovcr a two-year period
Twenty-eight such compounds were effective insccticides
Was effective against Polyphagot nrsonemus and Plutella xylostella
Show insecticidal properties
89
90
51
55
58
Insecticidal investigations involving other organotin compounds
Compound
Comments
Reference
Tributyltin sucrose phthalatc
Gave maximal activity against the mosquito Aedes uegypti
fourth-instar larvae
91
Tricyclopentyltin fluoride
At 400ppm gave 1009, control of the cabbage looper Trichoplusia
92
ti i
Hcxamct hyldistannane
Tested as a fumigant against the stored product pests Atragenus
megutomci (black carpet beetle); Lusiodermn sericorne (cigarette
beetle) and Triholeuni c o ~ f l s u (confused
m
ff our bcetle). It was more
effective than methyl bromide. when exposed in free space and in a
Me,Sn(CH2),NH CO NH . C O . C,H,CI-2
At 50ppm gave 76100%
Q
NH, CR =CHR'
R,R'= H. Me,Sn
R+R'
kill o f Spodoprera littoralis larvae
93
94
A mixture of the cis and trans isomers gave 92-1007c:
mortality against larvae or eggs of Spodoptera littoralis
95
The cis isomer at 0.27; gave 9@100% mortality of Spodoptera
litrorulis larvae within 24 h. Similar results were obtained againsl
.4eties argypti larvae. and adults o f Musca domesticit and Aphis
96
fahat.
Ph,SnNCSc T M E N
(TMEN = tetramethylethylene diainide)
Ph,Snh, L
Ph,SnS('(SMelNNCI H)
(and other Schiff base complexeb)
Controlled flies Chilo suppressalis and mite Tetranychus chinensis a1
500 ppm
97
Showcd high activity against the cockroach Periplanata umericanu
98
The parent azide and its coinplcxcs (with various ligands L) were
effective against Periplanata americana. Complexes with oxygen
donor ligands tended to show highest activity
99
Insecticidal activity is claimed
100, 101
Show highcr activity against cockroach Periplannta americnna than
Ph,SnCI
102
Organotin compounds in agriculture since 1980. Part 2
341
Table 2.4.3.2 (continued)
Compound
(MeC,H,I ,SnCI . L,,
L=Ph,PO, P ~ : I z = OI ,
C'F,
Reference
Comments
~
~~
~~
Gave maximal activity against fourth-instar larvae of the mosquito
Aedes aegypti
92
R=SnRu, at O.Ol'3; in acetone gave loo?:, kill of 25 houseflies
R = SnPh, and SnCy, are also claimed
103
At 100-400 ppm killcd IOO?;, Spodoptera litrornlis L, larvae and
Anthonnnious graridis adults
Controlled green peach aphids on marigold at 250ppm
104
Gave maximal activity against fourth-instar larvae of the
mosquito Aedes acqypti
92
Such complexes exhibit higher activity than either parent
towards adult cockroaches Periplanata arnericana
106
Compound is toxic (contact) to the stored product pests,
Trogoderinir grunciriirm and Trihuliuni cusfancuni. LD,, values were
0.61 127; and 0.6432')<, respectively
107
C'F3
ROP(O)(OSnR,)H
( R Me, Ph, Cy)
BuMe,SiiCI
[and other R,R',,-,,SnCI
Me,OctSnOAc
Et,OctSnOAc
~
-
[R-N
]2[ICH,),,SnX2X,]'-
ln=4. 5. X X'=hnlogen or NCS)
Ph
N-"
Bu
P+
N-N
Ph -6i 'Ph
105
Table 3.1 Effects on mite predators
Compound
Predator
Comments
~-
Cyhexatin
Fenbutatin oxide
Azocyclotin and
Cq hexatin
Anrhlyseius hibens
A . hiheris
4.rhari
Fenbutatin oxide
Cyhexatin
A . ehari
Azocyclotin
A . fiwlundicus
Azocyclolin
Cyhexatin
Fenbutatin oxide
4 . pofenfillue
Arocyclotin
Coccinrllu septenipunctutu
Euseius hihisci
E. hibisci
Cyhexatin
Fenbutatin oxide
4.fiillacis
A . potentillae
A . potentillae
Cyhexatin
Metaseinulus occrdentalis
Azocyclotin
Phvroseiuius persiwiilis
Cyhexatin
P. persindis
Reference
~~
Was found to be moderately toxic
Considered to be harmless
108
Both showed low toxicity to adult females, but were
highly toxic to eggs and immature stages for 10 days after
treatment
Was not toxic
At 0.2 g dm prolonged the hatching time of eggs from 2
to 8 days. but 100% hatch occurred. Residues c a s e d an
avoidance (repellency) and also suppressed egg deposition
U'as considered to be moderately toxic
At 0.03759:, gave 88% mortality (cf. C. q ~ t e i n p u n c ~ t r ~ t r )
Was harmful to this mite
Was found to be moderately toxic
Classified as harmless
109
At 0.0375% was spared or was only moderately affected
Showed high toxicity towards mite
Showed low toxicity
Was moderately- toxic to two different strains
Compound was used to adjust spider mite:predator ratio
to assist the control of the mite by M . occidenralis
Classified as harmless
Recommended to be used in zonjunction with this
beneficial mite
Considered to be harmless
Showed low toxicity (0-290/:, mortality)
105
109
110
111
112
1 I3
108
108
112
114
114
115
II6
48
1 I7
48
118
342
Organotin compounds in agriculture since 1980. Part 2
Table 3.1 (continued)
Compound
Predator
Comments
Fenbutatin oxide
P. persirnilis
Showed low toxicity ( 6 2 9 % mortality)
Classified as harmless, despite showing appreciable (50%)
adult toxicity
Could be safely used in combination with this beneficial
mite
Ar 0.2 g dm- prolonged the hatching time of eggs from
-2 to 8 days but 100% hatch occurred. Residues causcd
an avoidance (repellence) and also suppressed egg
deposition.
Was considered to be moderately toxic
Cyhexatin
Typhlodromus occidentalis
Cyhexatin
7: pyri
Fenbutatin oxide
Cyhexatin
Fenbutatin oxide
7: pyri
~
-
Reference
’,
Showed low toxicity and was suitable for corrective
treatment in combination with T pyri.
Classified as harmless
Showed low toxicity to beneficial entomoacariphages on
cotton
Was non-toxic to arthropod predators of 7: urlicae on
peanut
11x
48
117
110
108
119
108
23
120
Table 3.2 Effects on entomopathogenic fungi
Fungus
Comments
Reference
Fentin acetate
Pentin acctate
Beaurwia bassiana
Entomophfhoraaphidis
In vitro was inhibiting by contact and by spraying
121
122
Fentin h ydroxidc
Neozygites floridana
Fentin hydroxide
Nomuraea rileyi
Pcntin acetate
Fentin acetate
Fenbutatin oxide
Paecilomyces farinosus
VerriciNium lecanii
V . lecanii
Compound
~
_
_
In combination with maneb at a concentration recommended
for field use, the mixture inhibited germination of conida and
furthermore the fungus was killed. A decrease in infectivity of
E. uphidis on living pea aphids (Aphis pisum) was observed 6 h
after topical application. This activity was still present 48 h
after treatment
The efficacy of this fungus which infects T. urticae was
unaffected
Infection of lepidoptera larvae with this fungus was inhibited
to some degree
Was unaffcctcd
fn vitro was inhibiting by contact, but not by spraying
Had little effect on spore germination and mycelial growth in
vitro
121, 123
124
121
121
125
Organotin compounds in agriculture since 1980. Part 2
343
Table 3.3 Effects on other biological control agents and beneficial organisms
Compound
Organism
Comments
Reference
Cyhexatin and
Fenbutatin oxide
Cyhexatin
Aphidoletes aphidimym
aphid predator
Spiders
Both compounds showed low toxicity
126.
127
Cyhexatin
Spider, Chiracanthium
miidei, predator of
S. littoralis
Anthocris nemoralis,
valuablc predator
of pcar Psvlla
Cote.ria melnnoscelus,
larval parasite of the
gypsy moth
Was amongst the armoury of insecticideslacaricides,
which reduced the spider populations (hunters being more
affectcd than web-buildcrs). used in Quebec apple
orchards during 1979-1981
Did not kill spiders at a dose as high as 30mgg '
body weight
Very low toxicity was shown when it was examined on its
own or in combination with benzomate, and il was
classified as harmless
Had minimal effects on larval survival, adult
longevity and progeny production of the parasite
With low doses of B. thuringiensis it retards caterpillar
growth and so would enable greater parasitization by C'.
tnelanoscelus to occur
Was considercd to be harmless
129
Cyhexatin
Cyhcxatin
Fenbutatin oxide
Cyhcxatin and
Fenbutatin oxide
Fenbutatin oxide
Cyhcxatin
Encarsia formosa,
greenhouse white fly parasitc
Pygadeuon trichnps,
arthropod parasite
(ichneumon)
Trichogramma cacoeciae
egg parasite
Bacillus thuringiensis,
larval growth retarder
Fentin acetate
Rhizobia, nitrogen-fixing
root-nodule bacteria
Fentin hydroxide
Colletotrichum
glnenspnroides aeschynomene,
microbial herbicide
Fentin acetate
Eisenia foetida
earth worm
Fentin acetate
Lumhricus terrestris
earth worm
Honey bee
Honey bee
Cyhexatin
Fenbutatin oxide
Fentin acelate
Fentin hydroxide
Fentin acetate
Redwinged blackbirds
Redwinged blackbirds
Coturnix quail
128
130
131
Cyhexatin at 0.1% and fenbutatin oxide at 0.05% were
both classifed as harmless
132
Was observed to be harmless towards adult parasites
133
No harmful erfects were observed. Cyhexatin itself
retarded larval growth and so incrcased parasitization by
B. thuringiensis, since this can only successfully attack
small hosts
Concentrations of 700pgcm-' were required to
completely inhibit growth. This was less inhibitory than
other pesticides studied
At 0.56 kgha-' did not reduce disease development of
C.g.a. on northern joint vetch (Aeschyomene virginica)
and so is suitable for integrated control programes of A.
virginica in rice
A formulation with maneb was found to have an LC,,
of 27 mg kg- ' (dry weight of soil substrate)
In combination with maneb was found to have an LC,,
of 44mgkg- (dry weight of soil substrate)
Showed low toxicity
Was non-toxic by ingestion and slightly toxic by contact
Had an acute oral LD,,> lOOmgkg-' and an avian
repellency value R , , > 17;
LD,,> 100mgkg-'; R,,>l%
LD,* 10G117mgkg-'
130
134
135
136, 137
138
139
140
141
141
141
344
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