DE2342073C3 - Use of bis (trialkyltin) oxides to control mites on crops - Google Patents

Description

Mites (acarids) cause severe damage in agriculture and horticulture. These organisms are Widespread all over the world, they are known to affect numerous horticultural and agricultural crops Crops as well as poultry and cattle.

The bis (trialkyltin) oxides are known to be toxic for insects, mites, bacteria and other harmful organisms. It is most commonly used in the literature regarding the pesticidal effect the bis- (tri-n-butyltin) oxide mentioned, since this compound is apparently optimal with regard to pesiicidal effectiveness. Bis (trin-butyltin) oxide is an excellent pesticide, however, because of its high phytotoxicity, this compound has no wider application in the Control of pests on agricultural crops, ornamentals and other crops found.

U.S. Patent No. 3,264,177 states that various compounds containing a tricyclohexyltin residue, including bis (tricyclohexyltin) oxide, can be used to kill Arachnids are suitable on plants. Compared to bis (tricyclohexyltin) oxide, the advantage of the compound provided according to the invention is, inter alia, in the improved formulability. The hexa-Cs-7-alkyl compounds are liquids, the cyclo homologues on the other hand, sparingly soluble solids. The former can therefore be more easily formulated into emulsifiable concentrates, for example when using them no blockage of the spray device can occur.

The US-PS 32 48 283 mentions the usefulness of bis (triphenyltin) oxide as a fungicide on plants.

The adducts of bis (trialkyltin) oxides with compounds such as CO ₂ , CS2 and SO2 are described in the literature as fungicides.

GB-PS 9 46 770 describes pesticides for the treatment of useful plants and seeds which contain, inter alia, bis (trialkyltin) oxides with alkyl radicals with 3 to 8 carbon atoms as active ingredients. The propyl, butyl and Ociylvefindüng (C ₃ , C ₄ and C ₈ ) are mentioned in particular, whereby the low toxicity of the butyl compound is emphasized, while the propyl compound is tested for fungicidal effects on seeds and the octyl compound for fungicidal effects on plants became.

The bis (tributyltin) oxide mentioned as preferred is, however, as already mentioned above, known to be highly phytotoxic and, according to US Pat. No. 3,222,158, even has a herbicidal effect, as is also shown on the basis of the comparative tests below.

The Bjs (triocty! Tin) oxide, on the other hand, has practical no effect on mites, as can also be seen from the comparison tests below.

All the more surprising was the finding that from the group of pesticides known bis (trialkyltin) oxides those in which the

Alkyl has 5 to 7 carbon atoms, both

are not phytotoxic as well as being good acaricidal

Have an effect. The object of the invention was to provide a

new method of combating mite infestation in plants and preventing infestation of healthy ones Plants.

This task was achieved through the use of bis (tri- [acyclic alkyl] tin) oxides, for which the Al kylrest contains 5 to 7 carbon atoms, adducts of these bis (trialkyltin) oxides and CO2, CS ₂ or SO ₂ and mixtures thereof in an acaricidally effective amount to combat the attack on plants by organisms of the Acarina class. These bis (trialkyltin) - oxides, e.g. B. the amyl and hexyl derivative are suitable although known according to US-PS 34 24 775 as active ingredients for combating agricultural pests. From this, however, could be the doctrine that Crop plants with these active ingredients straight for

jo to treat mite control purposes, not derive, but the treatment was carried out according to this publication to combat harmful organisms not specified in more detail. Thus, the known include Instructions for use also cover the treatment of

Ji herbs and the soil and had to re the treatment of useful plants in view of the generally known, mostly in the foreground fungicidal properties of the organotin compounds are preferably interpreted to the effect that

do the treatment should be for the purpose of fighting fungal diseases.

The treatment of crops for the purpose of combating other harmful organisms is not, however Subject of the invention.

Rather, the invention relates to a method for combating agricultural pests using active ingredients of the formula (RjSn) ₂ O, where R is an alkyl radical having 5 to 7 carbon atoms, or of their adducts with CO ₂ , CS ₂ or

w SO ₂ . which is characterized in that useful plants are treated with these active ingredients for the purpose of mite control.

"Alkyl radicals" are understood to mean straight-chain or branched radicals. When performing the In the process, the mites (acarina) get in direct contact with the organotin compound Application to the plant by direct contact with the residue left on the plant Organotin compound and by uptake of Plant tissue, which with the organotin Compound has been treated, killed. The organotin compounds used according to the invention give the plant a residue acaricidal effect, so that still days or weeks after application

ho of the active ingredient killed mites infesting the plant will.

Examples of active ingredients that can be used according to the invention are:

Bis- (tri-n-penty | tin) oxide,

Bis (tri-n-hexy | tin) oxide,

Bis (tri-n-heptyltin) oxide,

Bis (tri-2-methylbutyltin) oxide,

Bis (tri-3-methylpentyltin) oxide and

Bis (dihexy | pentyltin) oxide.
Preferred compounds are

Bis (tri-n-pentyltin) oxide,

Bis (tri-n-hexyltin) oxide and

Bis (tri-n-heptyltin) oxide. mi

Bis (tri-n-hexylzmn) oxide is particularly preferred.

Examples of adducts from bis (trialkyltin) oxides and CO ₂ , CS ₂ and SO ₂ are the adducts from

Bis (tri-n-pentyltin) oxide and CO ₂ , bis (tri-n-hexyltin) oxide and CO ₂ ,

Bis (tri-n-heptyltin) oxide and CO ₂ ,

Bis (tri-2-methylbutyltin) oxide and CO ₂ ,

Bis (tri-n-pentyltin) oxide and CS ₂ ,

Bis (tri-n-hexyltin) oxide and CS ₂ , bis (tri-n-heptyltin) oxide and CS ₂ ,

Bis (tri-2-methylbutyltin) oxide and CS ₂ ,

Bis (tri-n-pentyltin) oxide and SO ₂ ,

Bis (trimhexyltin) oxide and SO ₂ ,

Bis (tri-n-heptyltin) oxide and SO ₂ ,

Bis (tri-2-methylbutyltin) oxide and SO ₂ .
The adducts are preferred

Bis (tri-n-pentyltin) oxide and CO »,

Bis (tri-n-hexyltin) oxide and CO ₂ and

Bis (tri-n-heptyltin) oxide and CO ₂ and especially the adduct

Bis (tri-n-hexyltin) oxide and CO ₂ .
The active ingredients used according to the invention are known and can be prepared by known methods. For example, 1 mol of tin tetrachloride can be reacted with 4 mol of a Grigi: "srd reagent RMgBr (R = the alkyl radical desired in the trialkyltin oxide). The resulting tetraalkyltin compound is then converted into the trialkyltin chloride by reaction with tin tetrachloride. The trialkyltin chloride is converted by reaction with sodium hydroxide converted into bis (tri- [acyclic alkyl] tin) oxide (see also J. Appl. Chem., Vol. 6, pp. 49-55).

The bis (trialkyltin) oxide adducts used according to the invention are known and can be prepared by known methods. For example, 1 mole of tri-n-hexyltin oxide can be reacted with 1 mole of carbon dioxide. The reaction is usually carried out by bubbling the gaseous carbon dioxide ^{through the organotin compound at from 0 to 50 °} C. and normal pressure. An inert solvent such as n-heptane or xylene can be used to facilitate the reaction. The inert solvent used, if any, is removed by distillation after the reaction has ended, if γ its removal is desired. The production method described is explained in more detail in US Pat. No. 3,417,117. The invention can be applied to the control of mites (or acarina) in all crops including crops such as soybeans, green beans, tomatoes, corn, pepper, strawberries, clover, alfalfa and cotton, fruits such as citrus fruits, apples, plums, cherries, grapes and Peaches and ornamental plants such as periwinkles, azaleas, chrysanthemums, roses, carnations and gladioli can be applied. The invention is of particular advantage in plants such as soybeans, peaches and certain chrysanthemum and rose species that are treated with

40

4 ^r i pesticides are highly prone to phytotoxic reactions.

The organotin compounds are used as acaricides formulated and applied in the same way as for plant protection products in general is common. So they are preferably incorporated into aericide mixtures, which are used in agricultural Pesticides, customary inert carriers and one or more of the organotin compounds contained, (Under inert carrier a solvent or a dry mass-giving M'Hel understood that has practically no acaricidal effect, but the possibility of diluting the Organotin compound offers.) Such acaricidal mixtures allow the application of the organotin Compounds on the plants in any amount in a convenient and controllable manner In the way that is common practice with agricultural pesticides. The mixtures or formulations can contain solids such as e.g. B. dusts, granules or wettable powders or liquids such as solutions, aerosols or emulsions. For application to plants, the mixtures contain im generally about 50 to 60,000 ppm of the organotin compound, depending on the amount per hectare applied amount. When using conventional methods of application, the concentration is Organotin compound in the mixtures generally about 50 to 3000 and preferably about 125 to 1500 ppm. When using the so-called "Low Volume" (LV) and "Ultra Low Volume" (ULV) Application processes, which have become increasingly important in recent years, lies in the Concentration of the organotin compound generally between 1200 and 36,000 ppm and preferably between about 2400 and 30,000 ppm. Regardless of the application method, the Amount of organic tin compound applied in the order of magnitude between about 0.112 to about 3.36 kg / ha and preferably between about 0.224 and about 2.24 kg / ha, depending on the type of plant, foliage density and severity of the miloenbefaiis. In order to facilitate the handling of large quantities, the Active ingredients generally formulated as concentrates that are inert with water, solvents or other Carriers can be diluted to the desired concentration just prior to use.

Dusts are obtained by treating the organotin compounds with a solid inert carrier such as talc, clay, silica, pyrophilite or the like. Mixed. Granular formulations are obtained by using granular carriers such as attapulgites or vermiculites, usually with particle sizes between 0.3 and 1.5 mm, with the organotin compounds, usually in a suitable solvent present dissolved, impregnated or by adding a solid inert support with a formulation of the Coated compounds in the form of a wettable powder. Wettable powders that are immersed in water or oil Achieving any concentration of the organotin compounds can be dispersed obtained by incorporating wetting agents into concentrated dusts.

The organotin compounds according to the invention are in customary organic solvents such as Kerosene, xylene, Stoddard solvent, acetone and the like. Sufficiently soluble so that they can be used directly as solutions or dispersions in these solvents can be used. Often such solutions or

Dispersions of the acaricide applied as aerosols under overpressure. Liquid preferred according to the invention Acarizidgemisehe are emulsifiable concentrates which contain the organic tin compound, an emulsifier and contain a solvent as the inert carrier. Such concentrates can be based on water and / or oil the concentration to be diluted for the application of the active ingredient to plants in the form of a spray it is asked for. The emulsifiers in these concentrates consist of surfactants that can be anionic, nonionic, cationic, ampholytic or zwitterionic. Make the emulsifiers usually about 0.1 to 30% by weight of the concentration. They can be used individually or in mixtures will. Examples of suitable anionic surfactants are the alkali metal and alkaline earth metals B. sodium and calcium) salts of fatty alcohol sulfates with 8 to 18 carbon atoms in the fatty chain and the alkali metal and alkaline earth metal (e.g. sodium and calcium) salts of alkyl benzene sulfonates with 9 to 15 carbon atoms in the alkyl chain. Examples of suitable nonionic surfactants The means are the polyethylene oxide condensate of fatty alcohols, the fatty chain of which has about 8 to 22 carbon atoms and in which about 5 to 25 moles of ethylene oxide are present per mole of fatty alcohol; examples of suitable cationic surface-active agents are the dimethyl dialkyl ammonium salts with alkyl chains of about 8 to 18 carbon atoms and a halogen as salt-forming anion. Examples of suitable ampholytic surfactants are the derivatives aliphatic secondary or tertiary amines in which one of the aliphatic substituents is about 8 to Has 18 carbon atoms and one substituent is an anionic, water-solubilizing group, e.g. B. a Sulphate, sulphonate or carboxyl radical. Specific Examples of ampholytic surfactants are sodium 3-dodecylaminopropionate and the Sodium 3-dodecylaminopropane sulfonate. examples for suitable zwitterionic surfactants are the derivatives of aliphatic quaternary ammonium compounds, in which an aliphatic radical has about 8 to 18 carbon atoms and one radical has one anionic water-solubilizing group. Specific examples of zwitterionic surfactants The agents are 3- (N, N-dimethyl-N-hexadecylammonio) propane-1-sulfonate and the J- (N, N-dimethyl-N-hexadecylainmonio) -2-hydroxy-propane-1-sulfonate. Numerous other suitable surfactants are described in McCutcheon's Detergents and Emulsifiers (1972), Allured Pub. Co., Ridgewood, N.J. Suitable solvents for the emulsifiable concentration are z. B. hydrocarbons such as benzene, toluene, xylene, kerosene and Stoddard solvents as well as halogenated hydrocarbons such as chlorobenzene, chloroform, fluorotrichloromethane and dichlorodifluoromethane. The solvents can be used individually or in mixtures.

In the following examples, acaricidal and phytotoxic effects were determined by the following test methods determined:

Test procedure I

Young (approx. J to 4 weeks old) were tested Fully develop soybean seeds with at least 8 13 liters used per planter. As an organism of Class Acarinn, the two-spot mite Tetranydius urticae was used.

Initial kill

A mite population of 25 mites is grown for 3 days on a 3-leaf tuft of Tesl plants allowed to grow. After 3 days, each plant is then sprayed with 15 ml of the acaricidal mixture living adult and immature mites were counted at different time intervals after spraying.

Residue activity

The plants are acaricidal with 15 ml

Mixture sprayed per plant. The next day, a 3-leaf tuft of each soybean plant with 10

Ȇ mites infected. Be at certain time intervals living adult and immature mites were counted.

Backward activity (washed off)

This test measures residue activity under conditions where the plant is between the Spraying and washing off the time of the mite infestation with water (so that rain or very

jo high humidity can be simulated). The plants are first sprayed with 15 ml of the acaricide mixture per plant. The next day each will Tufts of leaves to be infected by mites are sprayed with 25 ml of water and allowed to dry. To

j5 drying becomes a 3-leaf tuft of each soybean plant infected with 10 mites. At certain time intervals the living become fully grown and immature mites counted.

In each test, untreated comparative

4fi plants kept next to the test plants and equally infected with mites.

example 1

Emulsified concentrates were made from the following ingredients:

Active ingredient
Calcium LAS *)
TAEn ")
Xylene

189.25 g
31.94 g
31.94 g

200.48 g

*) Calcium salt of linear alkylbenzenesulfonate with alkyl chains with an average of 12 carbon atoms.
j5 "') Condensation product from 1 mol of tallow alcohol and 11 mol of ethylene oxide.

In the formulation labeled A, the active ingredient consisted of bis (tri-n-butyltin) oxide, in formulation

bo B was bis (trinhexyltin) oxide as the active ingredient. the Mixtures were diluted with water to the use concentration and afterwards on soybean plants Above test method tested for acaricidal and phytotoxic effects. The from Tables I to! V

b5 apparent results show that the bis (tri-n-hexyltin) oxide In the beginning, as a residue, excellent acaricidal effect with low plant phytotoxicity developed.

Table I.

formulation Active ingredient Initial Mortification (Number of remaining living I. 0 2 Il Mites) Conc I and 1 i tration Days after application of the active ingredient Πα 31 / 19 / (ppm) 0 16 / 0 18th Experiment No. 1 0 19 a, 30 / innumerable A iButyl derivative) 62.5 16a Leaves fallen B (mexyl derivative) 125 24 « 0 0 20 / 0 Comparison*) - 2.1 « 23 a countless Experiment No. 2 0 0 A (butyl derivative) 125 30 a 17a innumerable (Leaves fallen) (17 days) B (llexylderiviit) 250 Πα (0) (17 days) Comparison*) 24 a (innumerable) (17 days)

*> Infected with 25 mites but not treated with test compound.

a - adult mites.

ι - immature mites.

Uncountable - because of / u large numbers.

Tahelle Il Active ingredient
concentration Residual activity (number of remaining
Days after application of the active ingredient I. 10 Mites) formulation (ppm) 0 17th 7a innumerable Experiment No. 1 62.5 10a 4 a 16 / Leaves fallen A (butyl derivative) 125 1Oo 7a innumerable 21 / B (hexyl derivative) - 10a innumerable Comparison * ι 8a 65 / Experiment No. 2 125 10a 2a 0 (Leaves fallen)
(16 days) Λ ι butyl derivative) 250 10a 9a 55 β + /
(together) (0) (16 days) B (Hex>! Derivative ι - IOe (innumerable)
(16 days) Comparison*)

*) Infected with 10 mites, but without treatment with test compound.

a - fully grown mites ι - immature mites Uncountable = weeen 7 over number.

Table III

Formulation rune

Active ingredient concentration

ippm)

Residual activity washed off (number of remaining mites)

Days after application of the active ingredient
0 1 10

17th

Experiment No. I. 62.5 10a 3a A (butyl derivative) 125 10a 10a B (hexyl derivative) - 10a 9a Comparison*)

innumerable leaves fallen

100 / uncountable

innumerable innumerable

continuation Active ingredient Active ingredient 23 42 073 10 10 + i 2 1 plants) 17th 9 formulation concentration concentration (together) 9 / 4.5 (Leaves fallen) (ppm) (ppm) 0.5 11th (16 days) 3 / 0 (3 a, 4 /) (16 days) Veri-jch No. 2 125 62.5 Residual activity washed off (number of remaining mites) 70 « 5 (innumerable) A (butyl derivative) 125 4th 0.5 (16 days) 250 - Phytotoxicity (on average of 0.5 0 : B (hexyl derivative) - Days after application of the active ingredient 0 ; Comparison*) 125 0 I. 5 without treatment 250 Days after drug application 1-1.5 *) Infected with IO mites, however - lOo 9a 0 I. 0 a = adult mites. / = immature mites. ^: Uncountable = because of too large a number. 10a 8fl 0 4 i
5 Table IV
■ 5 1Oi / 8a 0 1 I formulation 0 0 18th with test connection. i 0 3 5 0 0.5 1.5 j Experiment no. 1 0 0 0 I A (butyl derivative) I B (hexyl derivative) (5) (17 days) ] Comparison *) (1.5) (17 days) Experiment No. 2 (0) (17 days) A (butyl derivative) B (hexyl derivative) Comparison*)

*) Without test connection.

Phytotoxicity rating 0 to 5;

0 = no damage, 5 = severe damage, plant / leaves practically destroyed.

Example 2

In formula B of Example 1, the bis (tri-n-hexyltin) oxide is replaced by an equivalent amount by weight of the following organotin compounds, with essentially the same results being achieved by the mite control practically equal to or better than with the mixture A and the Phytotoxicity are lower than with mixture A. The following compounds are used: bis (tri-n-pentyltin) oxide, bis- (tri-n-heptyltin) oxide, bis- {tri-2-methyIbutyltin) oxide, bis- (tri-3-methylpentyltin) oxide, bis (dihexylpentyltin) oxide, the adducts of bis (tri-n-pentyltin) oxide and CO2, bis- (tri-n-hexyltin) oxide and CO ₂ , bis- (tri-n- heptyltin) oxide and CO2, bis (tri-2-methyIbutyltin) oxide and CO ₂ , bis (tri-n-pentyltin) oxide and CS ₂ , bis- (tri-n-hexylz! nn) -ox ! d and CS ₂ , bis (tri-n-heptyltin) oxide and CS ₂ , bis (tri-2-methylbutyltin) oxide and CS ₂ ,

Bis (tri-n-pentyltin) oxide and SO2,
Bis (tri-n-hexyltin) oxide and SO ₂ ,
Bis (tri-n-heptyltin) oxide and SO2,
Bis (tri-2-methylbutyltin) oxide and SO ₂ .
a second series of tests was carried out to explain the invention.

Test method Il

Were lima bean plants with 50 to 100 adult strawberry spider mites (Tetranychus atlanticus) infected, the infected plants were then immersed in solutions of the test material, and the mortality of the adult spider mite was recorded

Example 3

Following the procedure of Example 1 were emulsifiable Concentrates manufactured The active ingredient in formulation B consisted of bis (tri-n-hexyltin) oxide, in formulation C from bis (tri-n-pentyltin) oxide and in

Formulation D from bis (tri-n-heptyltin) oxide. The results of the experiments with strawberry spider mites at the stated concentrations can be seen from Table V. They show that the above compounds can be used as Acaricides are effective. No phytotoxicity was observed.

Example 4

The formulation according to Example I was applied in the test method of Example 3 to the To demonstrate the effectiveness of the COr adduct on bis (tri-n-hexyltin) oxide. Table VI shows the effect of this compound against adult strawberry spider mites at the specified concentrations. In the In formulation B, the active ingredient consisted of bis (tri-nhexyl / .inn) oxide, in formulation E of the CC ^ adduct of bis (tri-n-hexyltin) oxide. The results show that the adduct is an excellent acaricide. It Virtually no phytotoxicity was observed.

Table V

Adult spider mite mortality after 5 days (mean 3 repetitions)

ίο

formulation

% Mortality

0.05% (w / v) 100 C. 100 B. 92 D. 0.025% (w / v) 100 C. 100 B. Il D. 0.0025% (w / v) 100 C. 97 B. 0 D. 0.001% (w / v) 81 C. 85 B. 0 D. Table VI

Adult spider mite mortality

formulation

% Mortality

0.005% (w / v)
B.
E. 100
100 0.0005% (w / v)
B.
E. 62
100 0.00005% (w / v)
B.
E. 13th
32

Example 5

To prove that the compounds according to the invention, i. H. with alkylresia with 5 to 7 C-atoms, which are superior to those with less than 5 and more than 7 C-atoms, were the following experiments carried out.

Young soybean plants (variety Wayne) and cotton plants (variety Coker 4104) is used. Each experiment was carried out with 3 soybean plants and 3 cotton plants, the plants using a "Preva!" sprayer with 15 ml of solution, the concentration of bis (trialkyltin) oxide from the respective table can be seen, were sprayed. During the experiment, two-sided Spider mites used.

Experiments A, B and C illustrate the akari / idc effect of bis- (tri-n-butyltin) oxide (TBTO). Bis (trin-pentyltin) oxide (TPeTO), bis- (tri-n-hexyltin) -oxicl (THTO), bis- (tri-n-heptyltin) oxide (THeTO) and bis- (tri-n-octyltin) oxide (TOTO). The phytotoxic effect of these compounds can be derived from experiments D and E emerged.

In Experiment A, 17 to 22 mites were left in each group infested from 3 soybean plants. 3 days after infestation, the plants were exposed to the active ingredient solution sprayed. The remaining mites were counted on the days indicated in the table.

In experiment B 3 leaves per soybean plant were marked and isolated by means of a substance, so that it prevents mites from spreading from a particular leaf to the rest of the plant. ) ede plant is then sprayed with 15 ml of treatment solution. The following day, each group of 3 plants with 10 Mites infected. On the following days, the mites (per group of 3 plants) counted.

Experiment C corresponds to experiment B, but you worked with cotton plants and only one Sheet marked and isolated.

Experiments D and E give the phytotoxicity of the compounds used in experiments A to C. again. The procedure was as in Experiment A. The plants were subjectively rated using on a scale from 0 to 5, with 0 indicating no damage and 5 indicating plant death mean. The values given are the mean values of 3 plants.

Experiment F. Emulsifiable concentrates of the following composition were produced:

Active ingredient

TaIg-O- (C ₂ H ₄ OX ₁ -H
Xylene

189.25 g
31.94 g

31.94 g
200.48 g

These concentrates were diluted with water to the use concentration and their acaricidal and phytotoxic effect on soybean plants in 2 test series according to the explanations on page 9 of the present description (test method I). The active ingredient in the first concentrate existed from bis (tri-n-hexy! tin) oxide, in the second concentrate from the CO2 adduct of bis (tri-n-hexyltin) oxide. the Table IX shows the results.

Table VIf

(Number of remaining mites)

i. J "t L · \ JI -J

formulation Effective loft 25OTpM 250 ipm 125 tpm Days O after application of the active ingredient O 4th 0 8th 4th 11th 14th 0 ' please 18th Bis (tri-n-alkyltin) oxide Concentration 25OTpM 25OTpM 125 tpm 1 O 0 5 0 17th 25OTpM 25OTpM 125 tpm I. O 2 (I. 7th 26th Leaves fallen 9 U Test Method A - Soybean Plants 250 tpm 25OTpM 125 tpm 6th 4th 20th 86 0 70 39 η TBTO (butyl derivative) 25OTpM 25OTpM 125 tpm 13th Il 72 0 innumerable 68 0 TPeTO (pentyl derivative) O O O 14th 15th > 100 12th > 100 0 TIITO Ulev. 'Derivative) Method B - Soybean Plants Test Method C - Cotton Plants 0 > IOO Puff egg 61 TIIeTO (heptyl derivative) IBIO TBTO 4th 0 8th 17th 52 TOTO (OUyl derivative) TPcTO TPeTO 3 4th 6th 4th I. comparison Tino THTO 6th I. 18th 26th 0 TIIeTO THeTO 5 6th 27 60 4th 9 TOTO TOTO 8th 6th 76 84: 34 0 comparison comparison 9 9 58 4? 42 > 100 > 100 10 8th 4th 4th > 100 3 0 6th 4th 1 0 17th 36 > 100 8th 3 29 77 0 IO 8th 56 > 100 0 8th 8th 0 32 > 100

Table VIII

Phytotoxicity (on average of 3 plants)

formulation Active ingredient - soybean plants Days after Ingredient-consuming 4th 8th Il 14th 18th Bis (tri-n-alkyltin) oxide concentration 25OTpM 250 ppm I. 2 5.0 5.0 5.0 5.0 5.0 Test procedure D - 250 ppm 3.7 4.2 4.5 4.5 5.0 TBTO 250 ppm 4.5 4.5 1.0 1.5 1.5 1.5 1.5 TPeTO 250 ppm 3.0 3.5 0.5 0.5 0.5 0.5 1.5 THTO 0 1.0 1.0 0.5 0.5 0.5 0.5 1.0 THeTO - cotton plants 0.5 0.5 0 0 0 0 0 TOTO 250 ppm 0.5 0.5 comparison 250 tpm 0 0 1.5 2.0 2.5 2.5 2.0 Test method E - 25OTpM 0.5 1 1.2 1.2 0.2 TBTO 250 tpm 1.5 1.5 0 0.2 0.2 0.5 0.2 TPeTO 250 ppm 0.5 0.5 0 0.2 0 0 0 THTO 0 0 0 0 0 0 0.5 0.5 THeTO 0 0 0 0 0 0 0 TOTO η
\ j 0 comparison 0 0

15th 23 42 073 Residue activity (number of remaining mites) 250 ppm 10 0.5 5 4th 7th 16 15th 3 18th THTO 250 ppm 10 0 3 0 Table IX F - soybean plants THTO ■ CO ₂ 125 tpm 10 0 8th 4th 8th 84 15th Test procedure WirkstolT- THTO 125 tpm 10 0 4th 1 0 20th 0 formulation Bis (tri-n-alkyltin) oxide concentration Days after Active substance application THTO · C0 _: 62.5 ppm 10 0 9 5 4th 100 100 THTO 62.5 ppm 10 0 9 1 1 10 100 75 1 2 THTO · CO ₂ (on average of 3 plants) 8th 8th 100 Phytotoxicity 250 tpm 04 8th 7th 18th 2.0 100 THTO 250 ppm 0.5 0 14th THTO · CO ₂ 125 tpm 04 1.0 2.0 49 2.0 2, ( THTO 125 tpm 0 0.5 1.0 15th 1.0 ι ,; THTO · CO ₂ 62.5 ppm 0 1.0 14th 100 0.5 2, ( THTO 62.5 ppm 0 0.5 0.5 31 0.5 1,( THTO · CO ₂ 0.5 0.5 0, i 0 0.5 2.0 Ο, ί 1.5 2.0 1.0 0.5 0.5

Claims (1)

Claim; Process for combating agricultural pests using active ingredients of the formula (RjSn) ₂ O, in which R is an alkyl radical having 5 to 7 carbon atoms, or of their adducts with CO ₃ , CS ₂ or SO ₂ , characterized in that these active ingredients Treated crops for the purpose of mite control.