Note: Descriptions are shown in the official language in which they were submitted.
~5~3
The present invention relates to phosphoric acid phenylsulphonamide
esters, a process for their manufacture and the;r use in pest control.
According to the present invention, there is provided compounds
of the formula I
X
\ p _ ~ 2 N d (I)
wherein
R represents an alkyl group, having at most 2 carbon a~oms,
Rl represents an alkyl group having from 3 to 5 carbon atoms or an alkoxy-
alkyl group having at most 5 carbon atoms in toto,
R2 represents a hydrogen atom or an alkyl group having at most 5 carbon
; atoms,
R3 represents an alkyl group having at most 5 carbon atoms,
X and Xl, independently of one another, represent a hydrogen or a halogen
atom or an alkyl group having at most 5 carbon atoms, and
~ Y represents oxygen or sulphur.
- The invention also provides a method of combatting pests of the
` class Insecta or Acarina at a locus which comprises applying to said locus
a compound defined above.
" .
Halogen is to be understood as meaning fluorine, chlorine,
bromine or iodine, but in particular chlorine. Preferred haloalkyl groups
w~th I to S carbon atoms are Cl-CH2-CA2-, C13C- and ~3C-.
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-
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The groups cited hereinabove which are possible
for R to R3, X and Xl, may be straight-chain or branched.
Examples of such groups include: methyl, methoxy, methoxy-
methyl, ethyl, ethoxyethyl, ethylthioethyl, propyl, iso-
propyl, n-, i-, sec. and tert.butyl, n-pentyl and the iso-
mers ~hereof, allyl, methallyl, n-penten-5~yl, propargyl,
isobutinyl.
~referred compounds on account of their action
are those of the formula I, wherein R represents methyl ~`
or ethyl, Rl represents propyl, n-butyl, n-pentyl or
1 C2H50CH2CH2 , R2 represents hydrogen, methyl or ethyl, R3
-~ represents methyl or ethyl, X and Xl each represen~s hy-
~, drogen or chlorine, and Y represents oxygen or sulphur. -
Particularly preferred compounds, however, are
those of the formula I, whereln R represents ethyl, R
represents propyl, n-butyl, C2H50CH2CH~- or n-amyl, R2
and R3 each represents methyl or ethyl, X and Xl repre-
sent hydrogen or chlorine and Y represents oxygen.
The compounds of the formula I can be manufactured
according to methods which are known per se:
R 11 ~>/S02N< 2
1) C>~Cl ~ H(~ 3
(II) (III) X acid binding
agenL
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.
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) ~ S~ P-Cl. + MeO- ~ 2 <~
(II) (IV) . ~ r
Xl r~ac~ion tempera~ure 0-120~C
y X SO2N /R2
3a) > ~ 3
R0 ~ ~ -~ MeSI-I
(V) Xl
.. . .
~, y X ~R2
3b) RO\ 11 ~S02N<
Me~
.. Xl ` (VII~ reaction temperature 0-100C
(VI)
; ~. . .
~, - In the formulae II to VII, R to R3, X, Xl and
A have the meanings given in respect of the formula I,
,.
' Me represents an alkali metal, in particular sodium or
potassium, ammoni~n or alkylammonium with up to 5 carbon
atoms, and Hal represents chlorine or bromine.
Suitable acid binding agents are: tertiary
amines, e.g. trialkylamines, pyridine, dialkylanilines;
inorganic bases, such as hydroxides; carbonates and bî- ~ :
carbonates of alkali and alkaline earth metals. It is
sometimes necessary to use catalysts in the reactions, ~:
e.g. copper or copper chloride. ~:
Processes 1, 2, 3a and 3b may be carried out at ;~
- 4 -
,
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normal pressure (3a at up to lO abmospheres a~solute pres-
sure) and in solvents or diluents Suitable solvents or
diluents are e.g. ethers and e~hereal compounds, such as
diethyl ether~ dipropyl ether, dioxan, dimethoxyethane5
tetrahydrofuran; amides,such as N,N-dialkylated carboxylic
amides; aliphatic, aromatic and halogenated hydrocarbons,
in particular benzene, toluene, xylenes, chloroform, chloro-
benzene; nitriles, such as acetonitrile; dimethyl sul-
phoxide, ketones such as aeetone, methyl ethyl ketone.
Some of the starting materials of the formulae II
and V are known compounds which can be manufactured in
analogous manner by known methods. The compounds of the
formula I display a broad biocidal activity and are there-
fore suitable for combating various plant and animal pests
and as plant growth regulators. Surprisingly, however, the
~, compounds of the formula possess insecticidal and acarici- -
dalt properties which are superior to those of known,
analogoas compounds, and they may be used against all de
velopment stages, e.g. eggs, larvae, pupae, nymphs and
addults, of insects and representatives of the order
Acarina, for example against insects of the families:
' Tettigonidae Tenebrionidae
Gryllidae Chrysomelidae
,. . .
Gryllotalpidae Bruchidae -
Blattidae Tineidae
.
Reduviidae Noctindae
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~ OIS~ 3
Phyrrhocoriae Lymatriidae
Ci~icidae Pyralidae
Delphacidae Culicidae
Aphididae Tipulidae
Diaspididae Stomoxydae
Pseudococcidae Trypetidae
" Scarabaeidae Muscidae
Dermestidae Calliphoridae and
Coccinellidae Pulicidae
Acarida of the families:
Ixodidae
Argasidae
I Tetran~chidae and
- Dermanyss_ ae.
The insecticidal or acaricidal act:ion can be substantially broadened
and adapted to the particular circumstances by the addition of other insecti-
cides and/or acaracides.
: ' .
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- The active substances of the formula I are also suitable for
combating representatives of the division Thallophyta, e.g. viruses~ bacteria
and fungi. They thus possess fungicidal properties against~phytophathogenic
fungi on various cultivated plants, such as cereals, maize, rice, vegetables,
ornamental plants, fruit trees, vines, farm products, etc.
With the new active substances it is possible to control or destroy
fungi occurring on fruit, blossom, leaves, stems, tubers and roots, and from
which parts of plants which grow later then also remain free. The active
substances of the formula I are active in particular against phytop~atogenic
10fungi belonging to the following classes: Oomycetes, Zygomycetes, Ascomycetes,
Basidiomycetes, Denteromycetes.
In addition, the new active substances can also be used for treating
seeds, fruit, tubers etc., and the protecting them from fungus infections, for
example from smut fungi of all kinds, such as Ustilaginales, e.g. Ustilago,
Tilletia, Urocystis, Turbicinia and Phoma types.
In addition to the above cited acaricides and insecticides, it is
also possible to admix the active substances of the formula I with, for
example, bactericides, fungistatic agents, baceteriostatic agents, nematocides
end/or fungioldes, in o der to broaden the aotivity ~peotrum.
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Furthermore, the compounds of the formula I are suitable for combat-
ing plant pathogenic nematodes.
The compounds of the formula I may be used as pure active substance
or together with suitable carriers and/or additives. Suitable carriers and
additives can be solid or liquid and correspond to the substances convention-
ally used in formulation technique such, for example, as solvents dispersants,
wetting agents, adhesives, thickeners, binders and/or fertilisers.
For application, the compounds of the formula I may be processed
to dusts, emulsion concentrates, granules, dispersions, sprays, to solutions,
or suspensions in the conventional formulation which is commonly employed in
application technology. Mention may also be made of "cattle dips" and
"spray races", in which aqueous preparations are used.
The ~gents according to the invention are manufactured in known
manner by intimately mixing and/or grinding active substances of the
formu]a I with the suitable carriers, optionally with the addition of dis-
persants or solvents ~hich are inert towards the active substances. The
active substances
~:
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may take and be used in the following forms:
Solid forms:
Dusts, scattering agents, granules, coated granules,
impregnated granules and homogeneous granulesn
~iquid forms:
a) active substances which are dispersable in water;
wettable powders, pastes, emulsions;
b) solutions.
To manufacture solid forms (dusts, scattering agents),
the active substances are mixed with solid carriers. Suitable
carriers are, for example: kaolin, talcum, bolus, loess, chalk,
~ limestone, ground limestone, attaclay, dolomite, diatomaceous -
- earth, precipitated silica, alkaline earth silicates, sodium
and potassium aluminum silicates (feldspar and mica), calcium
and magnesium sulphates7 magnesium oxide, ground synthetic
materials, fertilisers~ for example ammoniu~ sulphate, ammonium
phosphate~ ammonium nitrate, urea, ground vegetable products~ -
such as corn meal, bark dust, sawdust, nutshell meal, cellulose
powder, residues of plant extractions, activated charcoal etc.
These substances can either be used alone or in admixture with
one ano~her.
-~ Granules can be very easily manufactured by dissolving -
an active substance of the formula I in an organic solvent
and app~ying the resulting solution to a granulated material~ for
example attapulgite, SiO2, granicalcium~ bentonite~ etc. and then -~
evaporating the sol~ent.
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Polymer granu]es can also be manufac-tured by mixing
the active substances of the formula I with polymerisable
compounds (urea/formaldehyde; dicyandiamide/formaldehyde;
melamine/formaldehyde or others), whereupon a mild poly-
merisation is carried out that does not affect the active sub-
stances and in the process of which the granulation is carried
out during the gel formation. It is more advantageous to
impregnate finished, porous polymer granules (urea/formal-
dehyde, polyacrylonitrile, polyester or others) which have a
specific surface area and a favourable predeterminable adsorp-
tion/desorption ratio, with the active substances, for example
in the form of their solutions (in a low boiling solvent) and
to remove the solvent. Polymer granules of this kind`in the
form of microgranules having a bulk density of 300 g/litre
to 600 g/litre can also be manufactured with the aid of atom-
isers. The dusting can be carried out from aircraft over ex-
tensive areas of cultures of useful plants.
It is also possible to obtain granules by compact-
ing ~he carrier with the active substance and carriers and
~0 subsequently co~minuting the product.
To these mixtures can also be added additives which ~rlh
stabilize the active substance and/or non-ionic, anionic and
cationic surface active substances, which, for example, im-
prove the adhesion of the active ingredients on plants or parts
of plants (adhesives and agglutinants~ and/or ensure a better
wettability (wetting agents) and dispersibility (dispersing
,
--10--
.. . .
, . . . .
~SO15~3
agents). Examples of suitable adhesives are the following:
olein/chaIk mixture, cellulose derivates~ (methyl cellulose,
carboxymethyl cellulose), hydroxyethyl glycol ethers of mono-
alkyl and diaIkyl phenols having 5 to 15 ethylene o~ide radi-
cals per molecule and 8 to 9 carbon atoms in the alkyl radi-
cal, lignin sulphonic acids, their alkali metal and alkaline
earth metal salts, polyethylene glycol e~hers (carbowaxes~,
fatty alcohol polyethylene glycol ethers having 5 to 20
ethylene oxide radicals per molecule and 8 to 18 carbon atoms
in the fatty alcohol moiety, condensation products of ethylene
oxide/propylene oxide, polyvi~yl pyrrolidones, polyvinyl al-
cohols, condensation products of urea and formaldehyde, and
- also latex products.
The water-dispersible concentrates of the active sub-
stance, i.e~ wettable powders, pastes and emulsifiable con- ~ -
centrates, are agents which can be dil~ted with water to any
- concentration desired~ They consist of active substance,
carrier, optionally additives which stabilize the active sub-
stance, surface-active substance and anti-foan agents and,
'
optionally, solvents.
~ettable powders and pastes are obtained by mixing
and grinding the active substances with d~spersing agents and
pulverulent carriers in suitable apparatus until homogeneity
is attained. Suitable carriers are, for example, those men-
tioned for the solid forms of application. In some cases it is
.,
. .
i. : . , . ,: . ,
,., "
5~;3
advantageous to use mixtures of dif~erent carriers. As dispers-
ing agents there can be usedg ~or exampleg condensation pro-
ducts of sulfonated naphthalene and sulfonated naphthalene deri-
vatives with formaldehyde, condensation products of naphtha-
lene or naphthalene sulfonic acids with phenol and formalde-
hyde, as well as alkali, ammonium and alkaline earth metal
salts of lignin sulfonic acid, in addition, alkylaryl sulfonates,
alkali and alkaline earth metal salts of dibutyl naphthalene
sulfonic acid, fatty alcohol sulfates such as salts of sulfated
hexadecanols, heptadecanols, octadecanols, and salts of sulfated
fatty alcohol glycol ethers, the sodium salt of oleoyl ethionate,
the sodium salt of oleoyl methyl tauride, ditertiary acetylene
glycols, dialkyl dilauryl ammonium chloride and fatty acid al-
kali and alkaline earth metal salts.
Suitable anti-~oam agents are silicones.
The active subs*ances are mixed, ground, sieved and
strained with the additives cited hereinabove in such a manner, -
that~ in wettable pow~ers, the solid par~icle size of ~rom 0.02
to 0.04 and in pastes, of 0~03 is not exceeded. To produce emul-
sifiable concentrates and pastes, dispersing agents such as those
cited above, organic solvents and water are used. Examples of
suitable solvents are: alcohols, benzene, xylene, toluene,
dimethyl sulfoxide, and mineral oil fractions boiling between
120 and 350 C. The solvents must be practically odourless~ -
not phytotoxic, inert to the active substances.
. ~
.
; -12-
:,
,, . - ~ . .. . . . . .
.
Furthermore~ the agents aeeording to the invention
- ean be applied in the form of solutions. For this purpose the
aetive substanee or several aetive substanees of the general
; formula I are dissolved in suitable organie solvents, mixtures
of solvents or in water. Aliphatie and aromatic hydroearbons,
chlorinated derivatives thereof, al~yl naphthalenes, and min-
eral oils singly or in admixture with each other, can be used
as organic solvents.
The content of active substanee in the above des-
cribed agents is between 0.1% to 95%, in whieh eonneetion it
should be mentioned that, in the ease of application from air-
craft or some other suitable means of application, it is pos-
sible to use coneentrations of up to 99.5% or even pure
active substanee.
, The active substances of the formula I can, for
; ~ example, be formulated as follows:
Dusts
, The following substances are used to manufacture a) a 5% and
;, b) a 2% dust:
a) 5 parts of aetive substanee
95 parts of taleum
b~ 2 parts of aetive substance
1 part of highly disperse siliea
97 parts of taleum
The aetive subs~anees are mi~ed with the earriers and ground.
, . . .
, :~
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-13-
.
;i3
Granules
The following substances are used to produce 5% granules:
5 parts of acti.ve substance,
0.25~parts of epichlorohydrin,
0.25 parts of cetyl polyglycol ether,
3.50 parts of polyethylene glycol,
91 parts of kaolin (particle size 0.3 - 0.8 mm)0
The active substance is mixed with epichlorohydrin
and dissolved with 6 parts of acetone; the polyethylene
glycol and cetyl polyglycol ether are then added. The thus
obtained solution is sprayed on to kaolin, and the acetone
subsequently evaporated in vacuo.
Wettable po~der:
.
The following constituents are used for the preparation of
a) a 40%, b) and c) a 25%, and d) a lC% wettable powder:
a)40 parts of active substance,
5 parts of sodium lignin sulphonate,
1 part of sodium dibutyl-naphthalene sulphonate,
54 parts of silica acid.
b)25 parts of active substance,
4,5 parts of calcium lignin sulphonate
1.9 parts of Champagne chaIk/hydroxyethyl cellulose
mixture (1:1)
1.5 parts of sodium dibutyl naphthalene sulphonate,
19.5 parts o silica acid,
19.5 parts of Champagne chalk,
-14-
. ' ' ' , . . ; : '. ' .' ': '
28.1 parts of kaolin.
c) 25 parts of active substance,
2.5 parts of isooctylphenoxy-polyoxyethylene-ethanol,
~, 197 parts of Champagne chalk/hydroxyethyl
cellulose mixture (l~
8~3 parts of sodium aluminium silicate,
16.5 parts of Ideselguhr,
46 parts of kaolin
d) 10 parts of active substance9
3 parts of a mixture of the sodium salts of
saturated fatty alcohol sulphates,
parts of naphthalenesulphonic acid/formaldehyde
condensate,
82 parts of kaolin.
The active substances are intimately mixed, in suitable
mixers, with the additives, the mixture being then ground in
the appropriate mills and rollers. Wettalble powders areobtained
which can be diluted with water to give suspensions of any
desired concen~ration.
Emulsifiable concentrates:
The following substances are used to produce a) a 10%
and b) a 25% emulsifiable concentrate:
a) lO parts of active substance~
3.4 parts of epoxidised vegetable oil, -~
.. .:
3.4 parts of a combination emulsifier consisting
of fatty aloohol polygIyool ether and ~lkyl-
. ~
- 15 _
,:
~ S~?563
arysulphonate calcium salt,
40 parts of dimethylformamide,
43~2 parts of ixylene~
b) 25 parts of active substance
2.5 parts of epoxidised vegetable oil,
10 parts of an aIkylarylsulphonate/fatty alcohol-
polyglycol ether mixture
5 parts of dimethylformamide7
57.5 parts of ~ylene.
From these concentrates it is possible to produce,
by dilution with water~ emulsion of any desired concentration.
~ Spray:
:: The following constituents are used to prepare a 5% spray:
5 parts of active substance,
:: 1 part of epichlorohydrin,
94 parts of benzine (~oilin.g limits 160 - 190 C). :~: :
,
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E X A M P L E
Manufacture of O-e~hyl-S-pro~yl-0-~4'-N~
dimethylsulphonamiclo-phenyl~-thiol-phosphoric-acid ester
. .
To a suspension of 14.4 g of 4-N,N-dimethyl-
sulphonamidophenol in llO ml of benzene are added 7.2 g
of triethylamine. W~lile stirring constantly, 14.5 g of
O-ethyl-S-n propylchlorothiophosphate are added drop-
wise. T~e mixture is stirred for 12 hours at room tem-
perature, when washed with water, 3% sodium carbonate
1 10 solution and again with water, and dried o~er anhydrous
sodium ~ulphate. --~
The benzene is distil]ed off and the residue
, - ,
purified by means of molecular distillation (135C/
0,001 Torr) to give the compound of the formula -
~ : O
C2H50~ ll ~==~
; C~H.~S > ~ S02~ H3)2 nD . 1,5298
:''
The following compounds are also manufactured
in analogous manner:
' ' ,''
.,
.. . .
63
y 2` 3
RO>II ~S02N< 2
RlS ~ 3
6 5
.
R Rl R2 IR3 Y ¦ 2 3 5 6
C2H5- (n)CI~H9- CH~- jCH~- 0 H H H H n20 = 1,5268
C2H5- C2H50CH2CH2- CH3- CH3- 0 H H H H nD = 1,5335
C2H5~ ( ) 3 7 CH~- CH3- 0 Cl H H H nD = 1,5378
C2H5- ( ) 3 7 C2H5- C2H5- 0 H H H H nD = 1,5238
C2H5- (n)C3H7- CH3- CH3- S Cl ¦H H H nD = 13 5593
C2T15- 3 7 C2H5- C2H5- S H H H H Smp.: 64C
C2H5- (n)c3H7- CH3- CH3- S H H H H n20 = 1,5514
C2H5- (n)C3H7- CH3- CH3- S Cl HCl H nD = 1,5710
C2H5- ( 5 11 CH3- CH3- S H HH H nD = 1,5393
C2H5- ( ) 3 7 CH3- CH3- 0 H 1 H H nD = 1,5390
C2H5- (n)C3H7_ CH3~ CH3- Cl H Cl H nD - 1,5381
C2H5- (n)C3H7- CH3- CH3- CH3 H H H
C2H5- ~n)C3H7 CH~- CH3- 0 H CH3 H H
C2H5- (n)C3H7- H CH3- 0 H H H H .
C2H5- (n)C3H7- H H 0 Cl H H H
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A) Insecticidal ingest poison action
Tobacco and potato plants are sprayed with a 0Oo5% aqueous emulsion
(obtained from a 10% emulsifiable concentrate)
After the coating has dried, Egyptian cotton leaf worms (Spodoptera
littoralis~ are settled on the tobacco plants and Colorado potato beetle
larvae (Leptino~arsa decemlineata) on the potato plants. The test is carried
out at 24C and 60% relative humidity. In the above test, the compounds
according to Example 1 display ingest poison action against Spcdoptera
littoralis and Leptinotarsa decemlineata.
B) S~stemic insecticidal action
To dete~mine the systemic action, rooted bean plants (Vicia fabae)
are put into a 0.01% aqueous active substance solution (obtained from a 10%
emulsifiable concentrate~. After 24 hours, aphids (Aphis fabae) are placed
on the parts of the plant above the soil. The aphids are protected from
contact and gas action by means of a special device. The test is carried
i out at 24C and 70% relative humidity. In the above tests the compounds
according to ~xample I displayed good insecticidal ingest poision action and
systemic insecticidal action.
Example 3
~; Action a~ nst Chilo Suppressalis
Six rice plants at a time of the variety Caloro were transplanted
into plastic pots (diameter at the top = 17 cm) and reared to a height of
about 60 cm. Infestation with Chilo suppressalis larvae (Ll: 3-4 mm long)
took place 2 days after application of the active substance in granule form
to the paddy water (rate of application: 8 kg of active substance per
hectare). Evaluation of the insecticidal action took place 10 days after
application of the granules.
The compounds according to Example 1 were active in the above test
against Chilo suppressalis.
19
.
' ~ , ,', ,
Example 4
Action against so l insects
Sterilised compos~ earth was homogeneously mixed with a wettable
powder containing 25% of active substance so that there resulted a rate of
application of 8 kg of active substance per hectare.
Young zucchetti plants (Cucumis pepo~ were pwt into plastic pots
with the treated soil (3 plants per pot; diameter of pot = 7 cm). Each pot
was infected immediately afterwards with 5 Aulacophora femoralis and Pachnoda
or Chortophila larvae. The control was carried out 4, 8, 16, and 32 days
after depositing the larvae.
At 80-100% kill after the first control, a fresh infestation with 5
larvae each was carried out in the same soil sample with 3 new 3ucchetti
plants~ If the activity was less than 80%, the remaining larvae remained in
the soil sample until the control immediately following. If an active sub-
, stance at a rate of application of 8 kg/ha still effected a 100% kill, a fur-
ther control with 4 and 2 kg of active subs~ance per hectare was carried out.
In the above test, the compounds according to Example I displayed
action against Aulacophora fermoralis, Pachnoda and Chortophila larvae.
-~ ample 5
Actio _against ticks
A) ipicephalus bursa
In each of two test series 5 adult ticks and 50 tick larvae are
counted into a glass tube and immersed for 1 to 2 minutes in 2 ml of an
aqueous emulsion from an emulsion series each containing 100, 10, 1 and 0.1
ppm of test substance. The tube is then sealed with a standardised cotton
wool plug and placed on its head, so that the active substance emulsion can
be adsorbed by the cotton wool~
In the case of the adults evaluation takes place after 2 weeks~ and
in that of the larvae after 2 days~ Each test is repeated twice.
The compounds according to Example 1 act in the above test against
adults and la~ae of Rhipicephalus bursa.
~ - 20 -
. . . . . .. . . . .
~6~5~5~3
B) Boophilus microplus (larvae)
Tests are carried out in each case with 20 OP-sensitive larvae
using an analogous dilution series as in the case of test A. (The resistance
relates to the tolerability of Diazinon)~
The compounds according to Example 1 act in these tests against
sensitive and OR resistant larvae of Boophilus microplus.
Acaricidal action
- ' ,
Phaseolus vulgaris (dwarf beans) have an infested piece of leaf
from a mass culture of Tetranychus urticae placed on them 12 hours before the
test for the acaricidal action. The mobile stages which have passed over are
sprayed with the emulsified test preparations from a chromatography atomiser
so that the spra~ broth does not run offO The number of living and dead
larvae7 adults and eggs are evaluated after 7 days under a steroscopic
microscope and the results expressed in percentages. During the ''interimll,
the treated plants are kept in greenhouse compartments at 25C.
The compounds according to Example 1 are active in the above test
against eggs, larvae and adults of Tetranychus urticae.
Example 7
.
~
To test the action against soil nematodes, the active substance (in
a concentration of 50 ppm) is applied to and intimatel~ mixed with soil
infected with root gall nematodes (Meliodogyne arenaria). Immediately after-
wards, tomato cuttings areplanted in the thus prepared soil in a series of
tests and after a waiting time of 8 days tomato seeds are sown in another test
- series.
In order to assess the nematocidal action~ the galls present on the
roots are counted 28 days after planting and sowing. The compounds according
to Example display good action against Meliodogyne arenaria~
_ 21 -
, ;; ~ , .
