NL8600440A - CONNECTION WITH PESTICIDE OPERATION. - Google Patents

Description

l i - - Compound with pesticide effect -

The invention relates to S, S-di- (tert-butyl) -ethylphosphonodithioate, pesticide preparations containing this compound as active ingredient and to the use of this compound as an insecticide and nematocide.

The compound of the invention has the formula (= 0) C-SC (CH ^) (formula 1) and exhibits a wide variety of insecticidal and nematocidal actions and has excellent stability and long-term residual action, especially in soil .

10

The compound can be used, in particular in agriculture, against adult specimens, larvae and eggs of Lepidoptera (butterflies and moths), e.g.

Heliothis spp. such as Heliothis virescens, Heliothis armigera and

Heliothis zea, Spodoptera spp. such as S. exempta, S_. littoralis, jJ. eridania, Marnes tra configurata; Earias spp. e.g.

E. insulana, Fectinophora spp. eg Pectinophora gossypiella,

Ostrinia spp. such as 0, nubilalis, Trichoplusia ni, Pieris spp. , Laphygma spp., Agrotis and Amathes spp. , ffiseana spp.,

Chilo spp. , Tryporyza spp. and Diatraes spp., 20 - -; - -

Sparganothis pilleriana, Cydia pomonella, Archips spp.,

Plutella xylostella; against adult specimens and larvae of

Coleoptera (beetles) eg Hypothenemus hamper, Hylesinus spp.,

Anthonomus grandis, Acalymma spp., Lema spp., Psylliodes spp.,

Leptinotarsa decemlineata, Diabrotica spp., Gonocephalum spp.,

Agriotes spp., Dermolepida, Lepidiota and Heteronychus spp.,

Phaedon cochleariae, Lissorhoptrus oryzophilus, Meligethes spp ,,

Ceutorhynchus spp. , Rhynchophorus and Cosmopolites spp .; Sitona spp .; against Hemiptera eg Psylla spp., Bomisia spp., Aphis spp., Myzus spp., Megoura viciae, Phylloxera spp., Adelges spp., 30 ---

Phorodon huaili, Aeneolamia spp., Nephotetti spp., Empoasca spp., '"·% F * *,% i ..

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Nilaparvata spp.,. Perkinsiella spp., Pyrilla spp., Aonidiella spp., Coccus spp., Pseudococcus spp., Helopeltis spp., Lygus spp., Dysdercus spp., Oxycarenus spp., Nezara spp., Hymenoptera e.g. Athalia spp. and Cephus spp., Atta spp .; Diptera e.g. Hylemyia 2 spp., Atherigona spp. and Chlorops spp. , Phytomyza spp.,

Ceratitis spp., Thysanoptera such as Thrips tabaci; Orthoptera such as Locusta and Schistocerca spp., Crickets eg Gryllus spp. and Acheta spp and Gryllotalpidae (crickets); Collembola e.g. Sminthurus spp. and Onychiurus spp., Isoptera, eg Qdontotermes ^ spp.,. Dermaptera eg Forficula spp. and also other arthropods of agricultural interest such as Acari (mites) e.g. Tetranychus spp., Panonychus spp. and Bryobia spp., Eriophyes spp., Polyphagotarsonemus sppv; Blaniulus spp., Scutigereila spp., Oniscus spp. and Triops spp. and also nematodes affecting plants, both roots and shoots, such as Heterodera spp., Globodera spp., Meloidogyne spp., Pratylenchus spp., Xiphinema spp. and Ditylenchus spp.

Since the action of the compound against corn rootworm (Diabrotica sp.) Is good and the residual effect in soil is long-lasting, the compound according to the invention is of particular importance for the control of corn rootworm. The duration of the residual activity in the soil of the corn rootworm compound is unexpectedly much longer than that of compounds of related chemical structure, as shown in the following test described in Example X.

Example I; Taste

The compounds tested had the general 2q formula:

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-3- R (X) P (1X1) (X2R1) (X3R2) CIA)

Compound 00 - 2 - 1 - 3 - 2 A Et - OS t-butyl S t-butyl ^ B Et - OS n-propyl S t-butyl C Et - 0 S iso-propyl S t-butyl D Et - 0 S iso-butyl S t-butyl E Et - 0 S n-butyl S t-butyl E Me - 0 S n-propy. 1 S t-butyl 10 G Et - ES t-butyl 0 iso-propyl H Et - SS t -butyl 0 t-butyl I Et 0 0 S t-butyl S t-butyl j Et 0 0 S t-butyl S sec-butyl 15

Compound A is the compound of the invention B is compound No. 2 of U.S. Patent 4,472,390 20 C is compound No. 7 of U.S. Patent 4,472,390 D is compound No. 9 of U.S. Patent 4,472,390 E Compound No. 10 of U.S. Patent 4,472,390 F is Compound No. 12 of U.S. Patent 4,472,390 G is Example 8 of U.S. Patent 4,268,508.30 H is a Compound A-related compound in U.S. Patent No. 4,268,508 Γ is compound no. 11 of PCX patent application no.

WO 83/008870 • 5-4 J is compound no. 10 of PCT patent application no.

WO 83/008870

Research on residual effect and persistence against corn rootworm ^ (Diabr ° tica sp.)

Research method

The soil used was a clay loam with a water content of about 23% of the oven dry weight (determined by drying a sample at 110 ° C for 24 hours). All concentrations of the test compound treatments were expressed as parts per million (ppm) of the oven dry weight of the soil. Before treatment with the test compound, the soil was passed through a 3.5 mm orifice screen.

The test compound was dissolved in dimethyl ketone to such concentrations that the addition of 1 ml aliquots of the solution to soil samples equivalent to 100 g of oven dry soil, concentrations of 0.1 and 0.5 ppm, and in some cases, 0.05 ppm of the test compound.

Soil samples equivalent to 500 g oven-dried soil were placed in polyethylene bags and 5 ml solution of the test compound in dimethyl ketone with the

desired concentration of test compound was added. The 2S

The contents of the bags were then thoroughly mixed. The bags were then opened for 1 hour to allow dimethyl ketone vapor to exit.

Soil samples from the bags were taken immediately. tested for activity against Diabrotica undecimpunctata (0 ° day).

The remaining soil was then stored in closed dark glass jars at 24 ° C. Further samples were taken and examined on the 7th, 14th, 21st, 28th, 42nd, 56th, 70th, and 84th days after treatment with the test compound, with the soil again 1 Λ

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- i - 5 - was mixed before the sample was taken out.

The action against Diabrotica was determined by the following method:

Diabrotica was grown on maize seedlings at 25 ° G.

About 20 g of treated soil was placed in a 25 x 75 mm glass vial containing 2.5 ml of distilled water and a sprouted maize seedling with good root development. 5 Diabrotica 5-day old larvae were placed on the ground and any larva that did not burrow into the ground after a few minutes was replaced until all larvae burrowed into the ground. The vial was covered with a mesh cover and kept at 25 ° C for 4 days. Each treatment was performed in quadruplicate, g g g 15 to 42 days, and the treatments on 56, 70 and

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84 days were run in duplicate. After the four-day period, the samples were examined. The numbers of dead and live larvae were counted and the average mortality rate of the larvae was calculated from the quadruple treatments compared to untreated controls.

An average mortality rate of 90 or more indicates a sufficient control level of Diabrotica sp larvae.

The results obtained are shown in the following 25 Tables A and B.

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From the above results, the following can be seen: (1) At a concentration of 0.5 ppm, Compound A gave an adequate level of control of Diabrotica larvae for more than six times as long as Compound B.

It has been shown that compound A gave a sufficient control level up to and including the 42nd day, while compound B on the 7th day no longer gave a sufficient control level. Even at a concentration five times greater (0.5 ppm), compound B between the 28th and 42δ days no longer gave a sufficient control level. In addition, Compound A through the 14 day gave a sufficient control level even at the low concentration of 0.05 ppm, while, as noted above, Compound B even at twice the concentration.

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(0.1 ppm) no longer gave adequate control on the 7 day.

(2) At a concentration of 0.1 ppm, Compound A gave sufficient control levels of Diabrotica larvae for more than six times as long as Compound C.

It has been shown that compound A up to and including the 42 day gave a sufficient control level, while • Θ compound C no longer gave an average mortality rate of 90% on the 7 day. At half this concentration (0.05 ppm), Compound A through the 14th day gave a sufficient control level, while Compound C did not reach this activity level even on the 0th day.

(3) Even at a concentration of 0.5 ppm, Compound D did not provide sufficient control level of 30 Diabrotica larvae on the 28th day, whereas Compound A, on the other hand

twice as long, up to and including the 42 day, at a five times lower concentration (0.1 ppm) gave sufficient control. At a concentration of 0.1 ppm, compound D

- 10 - even at the 0th day no sufficient control, while compound A gave sufficient control at this concentration up to and including the 42 day, and even at a five times lower concentration (0.05 ppm) up to and including gave sufficient control on the 14 day.

(4) At a concentration of 0.5 ppm, compound E on the 7th day no longer gave sufficient control level of Diabrotica larvae, while compound A gave sufficient control even at a five times lower concentration (0.1 ppm) for more than six times longer, up to and including 42 days.

Even at a ten-fold lower concentration (0.05 ppm), Compound A gave twice as long, until the 14th day, then control by Compound E at 0.5 ppm. At a concentration of 0.1 ppm, 15 th compound E showed little or no activity even on the 0 day, while compound A at this concentration up to the 42 day showed a sufficient control level and even at half this concentration (0, 05 ppm) until the 14 day gave a sufficient control level.

(5) At a concentration of 0.5 ppm, compound F did not provide sufficient control level of Diabrotica larvae on the 14 day, while compound A at a five-fold lower concentration (0.1 ppm) at least three times longer, up to and by 42 days, gave adequate control.

Even at a ten times lower concentration (0.05 ppm), compound A gave twice as long sufficient. β ♦ · ♦ control, up to and including the 14 day. At a concentration of 0.1 ppm, compound F did not reach a sufficient control level even on the 0 day, while compound A at this concentration up to and including the 42 day reached a level of 1 to 30 ....

effective control level, and even at half this concentration (0.05 ppm) up to the 14 day gave an adequate control level.

(6) Neither compound G nor compound H gave a sufficient control level of Diabrotica larvae even at the 0 day at concentrations of 0.5 ppm and 0.1 ppm, while compound A up to the 42 and the 14 day gave a sufficient control level, at concentrations that were only one fifth (0.1 ppm) and one tenth (0.05 ppm), respectively, of the highest concentration (0.5 ppm) of compound G and compound H tested.

(7) At a concentration of 0.1 ppm, compound I did not give a sufficient control level against Diabrotica larvae even on the 0th day, while compound A at this concentration gave sufficient control up to the 42 day. Even at a concentration five times lower (0.05 ppm), Compound A gave adequate control up to 14 days. At a concentration of 0.5 ppm, Compound I no longer gave a sufficient control level on the 56 day, while Compound A at that concentration gave sufficient control up to the 84 day. Compound A gave sufficient control even at a five times lower concentration (0.1 ppm) for a period comparable to that obtained by compound I at a five times greater concentration (0.5 ppm).

(8) Even at a concentration of 0.5 ppm, compound J

no more sufficient control level of Diabrotica larvae on the 14 day, while compound A at a five times lower concentration (0.1 ppm) gave sufficient control at least three times longer, up to the 42 day, and with a ten times lower concentration (0.05 ppm) twice as long, until the 14th day, gave an adequate control level. At a concentration of 0.1 ppm, compound J did not give -12- sufficient1 control even on the Qth day, while compound A gave sufficient control at that concentration up to the 42nd day and even at a concentration five times lower (0 0.05 ppm) up to the 14 day provided sufficient control.

(9) At a concentration of 0.1 ppm, compound A gave a sufficient control level of Diabrotica larvae, which control level persisted more than six times longer, i.e. at least up to the 42nd day, IQ as the most persistent of the comparative compounds at 0.1 ppm (compound B and compound C), which compounds at that concentration on the 7th day no longer gave a sufficient control level of Diabrotica, while - none of the other seven control compounds even Ί5 on the 0th day had a sufficient control level of

Diabrotica gave.

(10) Regarding the average mortality rate of Diabrotica found at a concentration of 0.1 ppm on the 21st, 28th and 42nd days, the results in Table 2o A show that Compound A was six times more effective than Compound on the 21 day. C and nine times more effective than compound D. On the 28th day, Compound A was nine and a half times more effective than Compound C and nineteen times more effective than Compound D. The other seven Comparative Compounds showed no effect on the 21st and 28th day. On the 42nd day, an average mortality rate of Diabrotica of 90% was found for compound Δ, while all nine comparator compounds showed no activity on the 42nd day. The results in Tables A and B clearly demonstrate the unexpected and significant advantage of Compound A over the nine Comparative Compounds both in the persistence of a sufficient control level of Diabrotica and in the activity against Diabrotica at given times after application of the test compounds. This is demonstrated particularly well by considering the results obtained at a concentration of 0.1 ppm of test compound, whereby a sufficient control level of Diabrotica with compound A was obtained at least until the 42nd day, while a comparative compound at this concentration ( Compound C) no longer gave adequate control on the 14th day, a comparative compound (Compound B) did not give sufficient control on the 7th day, and the remaining seven comparative compounds did not achieve sufficient control even on the 0 day. Even at a five times higher concentration (0.5 ppm), only two of the comparative

Compounds (Compound C and Compound I) have sufficient control for as long as, or slightly longer than, the time obtained with Compound A at the five times lower concentration of 0.1 ppa, PD

but even here, compounds C and I no longer provided adequate control on the 56 day, at a concentration of 0.5 ppm, while compound A "gave adequate control even after the Δ S4 day.

The following Examples 2 to 7 further illustrate the valuable insecticidal and nematocidal properties of S, S-di (tert-butyl) ethylphosphonodithioate (Compound A).

Example II: Control of maize root worm on field maize

Compound A formulated as a 10% granule was banded at the time of sowing a piece of soil with field corn contaminated with corn rootworm in rows. The corn plants were later uprooted and their roots were assessed for damage caused by rootworm (Diabrotica spp.) With a conventional root rating scale, with 6.0 the maximum pest infestation and 1.0 the absence of visible represents damage. The amounts used below are those of compound A in kilograms per hectare (kg / ha). The following results were obtained: Applied Assessment of the roots quantities _ (kg / ha) Replicates means

Connection A A B C D

0.84 '2.1 2.2 2.1 1.8 2.05 15 0.56 2.6 2.1 2.4 1.9 2.25 0.28 2.8 2.8 2.9 2.3. 2.70 untreated control 5.9 5.9 4.9 3.6 5.08 20 _

The low ratings of the carrots obtained in the treatments with Compound A compared to those of the untreated controls demonstrate the great effectiveness of this compound against corn rootworm.

Example III: Control of maize maize on field maize Compound A formulated as a 20% granule was applied at a rate of 1.12 kg / ha as a tire or in a furrow on a piece of ground containing field maize. Maize had been affected with both maize applications being carried out at the time of row sowing. The effectiveness of the treatment against maize maggot (Hylemyia platura) was later determined by pupae 5 along counting test lengths of a row, The numbers found in the treated soil plots were reported as a percentage of the numbers found in the untreated controls The following results were obtained:

Compound A found pupae as percentage 10 in 1.12 kg / ha of the pupae found in the control applied as a band 15 applied in a front 15

The reduction of the pupae by 85% and 70% respectively demonstrates the strong effect of compound A against maize maggots.

20

Example IV: Combating crickets in peat

Compound A formulated as a 20% granule was applied to peat infested with crickets (Gryllotalpidae species) in amounts equivalent to 5.56 and 11.2 kg / ha of Compound A.

The soil mounds formed by the insects were reported before and after the treatment. The following results were obtained: 30

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Compound A Untreated (kg / ha) control 5.6 11.2 5 number of soil heaps pre-treatment 13.8 7.3 after treatment 2.8 8.3 before treatment 10 »3 15.0 after-treatment 1.5 17.0 10 ______

The large reduction in soil heap numbers from pre-treatment to post-treatment counts demonstrates the utility of Compound A in controlling crickets.

Example V: Control of pea and bean calender larvae on beans in the field

Compound A, formulated as a 10% granule, was applied to the soil in two trials around emerging field beans that were sown in the spring in a plot of soil affected with pea and bean calenders in amounts equivalent to 1 kg / ha and 2 kg / ha of compound A. Test 1 was repeated four times and test 2 was repeated three times. About 7 weeks later, the plants were uprooted and the numbers of calender larvae on the roots were counted. The results were expressed as the mean percent reduction in the number of larvae compared to untreated control plants. The following results were obtained:

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- 17-

Compounding A Percentage reduction in the number of larvae (kg / ha) Test 1 Test 2 2 90.2 92 1 53.3 93.75 5

The large reduction in larvae populations obtained with compound A, in particular in the amount of 2 kg / ha in Test 1 and Test 2 and in the amount of 1 kg / ha in Test 2, shows the effectiveness of this compound against pea and bean calender larvae.

Example VI: Test to determine the effectiveness against white sugarcane larvae. Compound A was dissolved in acetone and this solution was used to treat soil amounts to obtain some known concentrations of the compound in the soil. After the solvent had evaporated, the treated soil was placed in glass pots (about 110 g of soil per pot). 20 pots were prepared for each concentration. Each pot then received a white sugarcane larva, Lepidiota frenchi, in the third stage. Larva mortality was determined 28 days later. The following results were obtained:

Amount of Mortality Rate Applied, adjusted Compound A in mg / kg soil for the mortality rate of the controls 0.5 47 1.0 89 30 2.0 95 4.0 100 8.0 100> «- 18 -

The results obtained demonstrate the strong insecticidal activity of compound A against white sugarcane larvae.

Example VII: Study of nematocidal effect :; (a) Ditylenchus dj psaci (stem and ball nematodes)

The nematodes were grown in a greenhouse on alfalfa plants (cv. Du Puits). Two or three months after the original infection, the plants were harvested and washed, after which the eggs and larvae of the nematodes were obtained by dipping the ruptured stems and leaves in water. After a sieving, a seed suspension in distilled water was prepared containing about 150 larvae per ml.

Equal parts of unpolluted soil sieved to a particle size of 1 to 2 mm and river sand were mixed. Test compound A, previously dispersed in distilled water using Tween 80, was added to aliquots of this soil to obtain the required series of dilutions of compound A into the soil.

200 ml plastic pots were partially filled with coarse untreated sand on which 100 alfalfa seeds were sown per pot. The pots were then filled with chemically treated soil, except in the case of untreated controls using untreated soil. Each jar was wetted from above with 5 ml of the nematode suspension so that each jar received about 750 larvae. The pots were kept at an optimum moisture content for the germination of the seed and the growth of the plants.

Twelve to fourteen days later, the alfalfa seedlings were harvested and examined for infestation by nematodes. The effectiveness of each treatment was determined as the percentage reduction of infestation compared to the untreated controls. The following results were obtained in two runs: 5 ___

Amount applied Percent reduction of compound A (kg / ha) tasting compared to controls

Test 1 Test 2 10 100 100 50 100 100 25 80 100 10 50 70 5 50 80 15 1 60 O'- "means" not tested in this amount used in this test ") 20 (b) Meloidogyne incognita (Carrot Knob nema tode)

The culture was held on tomato plants in a greenhouse. A standard root knot nematode graft suspension of about 1500 eggs per milliliter of distilled water was prepared from washed, macerated and sieved roots. At least 10 to 15% of the eggs were in the embryonic larval stage.

The soil prepared for the tests consisted of a mixture of equal parts of river sand, peat and uncontaminated soil, which mixture was prepared by hand mixing

used to be. This soil was seeded with enough egg suspension to obtain about 30,000 eggs per liter of soil. Connection A

%

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Was dissolved in acetone and adsorbed on a small amount of Attaklei, after which the acetone was removed by evaporation. Except for the untreated control soil, amounts of soil were then hand mixed with the treated Attaklei to obtain the required series of dilutions of the test compound in the final batches of soil.

Two pots were filled from each load of soil. These were wetted and kept in a humid atmosphere for two weeks. Two small tomato plants (cv.

Marmande) were then transplanted into each pot and kept in a greenhouse for an additional four weeks.

The plants were then harvested and washed, after which the root galls were counted. The effectiveness of each treatment was determined from the percentage reduction in bile formation compared to the untreated controls. The following results were obtained in two experiments: Applied amount of Percent reduction of compound A (kg / ha) tasting compared to controls

Test 1 Test 2 100 100 25 50 100 100 25 100 100 10 100 90 5 50 0 1 - 0 30 _ ("-" means "not tested for this amount used in this test") 1 »3 1 ί

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The above results demonstrate the high activity level against Ditylenclus dipsaci and the very high activity level against Meloidogyne incognita of compound A1

The compound according to the invention can be prepared by methods known per se. Preferably, the compound of the invention is prepared from an ethylphosphon halide starting material. The ethylphosphonhalide is reacted with 2-methylpropane-2-thiol in the presence of a base to obtain the compound of the invention.

According to an inventive feature, the compound of formula 1 is prepared by the process of using an ethylphosphonhalide of the general formula ΟΗ ^ ΟΗ2 ~ Ρ (= 0) (- Χ) -Χ ^ (general formula 2), wherein X is a halogen -15 represents an atom, preferably chlorine, and represents a halogen atom, preferably chlorine, or a tert-butylthio group ZSCCCH 2), react with generally two molar equivalents of 2-methylpropane-2-thiol when X 1 represents a halogen atom , or generally 1 molar equivalent of 2-methyl-20-propane-2-thiol as a tert-butylthio group, in the presence of a base, or with the alkali metal salt of the thiol, for example, the sodium salt.

The process proceeds according to the following reaction schemes A and B: 25

Reaction scheme A (X ^ represents a halogen atom) ch3ch2-p (= o) (-x) - ^ + 2 ch3c (sh) (ch3) ch3 (2A) 30 2 base ^ CH ^ Ï ^ -P ^ Oj ^ - SCCCEj). ^ + 2 base. HX / HX1

CD

Reaction scheme BCX ^ represents -SC (CH3) 3 / i '* -22- CH3CH2-P (= 0) (- X) -SC (CH3) 3 + CH3C (SH) (CH3) CH3 (2B) base ^ CH3CE2 -P (= 0) / lSC (CE3) ^ 2 + base. HX 5 (1) where X and X ^ have the meaning defined above. The reaction represented by reaction scheme A is preferred for the preparation of the compound of the formula 1.

The process is advantageously carried out at a temperature of about 0 ° C to 100 ° C in an organic solvent with an alkali metal salt of the thiol, which is prepared from the thiol and an alkali metal, e.g. sodium, or hydride thereof or a alkali metal hydroxide, for example sodium hydroxide.

Suitable organic solvents are, for example, benzene, toluene, cyclohexane, tetrahydrofuran, dimethylformamide, 2-butanone and acetone (dimethyl ketone).

2q Compounds of general formula 2 can be prepared by methods known per se. For example, the compounds of general formula 2A can be prepared by the methods described by Morita et al, Tetrahedron Letters, 28, 2522-6 (1978), Morita et al, Chemistry Letters (1980), 435-8, British U.S. Patent 1,374,757 and Pianfetti and Quin, J.Amer.Chem.Soc., J54, 851 (1962), and the compounds of general formula 2B can be prepared according to the method described in published British Patent Application No. 2087891A. 2-Methylpropane-2-3q thiol can be prepared according to the method described by Dobbin, J. Chem. Soc., 57, 641.

The compound of the invention is effective at low concentrations as an insecticide and / or nemato-

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Because it requires only small amounts of the compound for effective control, it is generally impractical to use the compound directly as such. It is therefore desirable that the compound be used in the form of insecticidal or nematocidal compositions comprising S, S-di (tert-butyl) ethylphosphonodithioate in combination with, and preferably homogeneously dispersed in, one or more compatible agriculturally acceptable diluents or carriers and / or surfactants (ie, diluents or carriers and / or surfactants that are accepted in the art as suitable substances for use in insecticidal or nematocidal preparations and that are compatible with the active ingredient).

Suitable formulations comprising the active compound according to the invention may be liquid dispersions or emulsions, preferably with 0.001-1Z w / v of the active compound. Since the active compound is substantially insoluble in water, it is desirable to add an inert, non-phytotoxic organic solvent to obtain a concentrate, which preferably comprises 2-75% w / v of the active compound and which is readily an aqueous medium can be dispersed to form a uniform dispersion of the active compound suitable for use. The compositions usually also include a surfactant. For example, an effective liquid composition can be prepared with the active compound, acetone or ethanol, water and a surfactant such as Tween-20 (polyoxyethylene sorbitan monolaurate) or any of the other suitable surfactants.

The preparations containing the active compound can also be prepared in solid form, for example powdered or granulated. The active compound can be, for example, mixed with a suitable solid carrier such as kaolin, bentonite, talc and the like, or incorporated into suitable grannies, for example of mineral clays, for example attapulgite, mantor morillonite, silica or meerschaum. 2 Preferably, the powdered preparations comprise 0.5-252 g / g of the active compound; the granular formulations preferably comprise 1-25% w / w of the active compound.

Compositions comprising the active compound may also include other pesticidal active ingredients, for example insecticides, nematocides and fungicides, for example thiofanox, carbofuran, aldicarb and benomyl.

In order to control insects and nematodes, the active compound is generally applied at the site where the insect or nematode coating is to be controlled. J2 is applied in an amount from about 0.1 kg to about 25 kg of active compound per ha. Under ideal conditions, depending on the pest to be controlled, the smallest amount can provide suitable protection. On the other hand, adverse weather conditions, pest resistance and other factors may require the active ingredient to be used in larger amounts.

When the pests are in the ground, the preparation containing the active compound is spread evenly over the area to be treated in a usual manner. The preparation can, if desired, be in the field or the area on which the crop grows generally or close to the seed or plant which must be protected against attack.

The active ingredient can be rinsed into the ground by spraying water over the area; this can also be left to the natural action of the rain. During or after application, the preparation can, if desired, be mechanically spread into the soil, for example with a plow or a

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j - 25 - V -1 disc. The preparation can be applied before planting, during planting, after planting but before sprouting or after sprouting.

The following example illustrates the preparation 5 ...

of the compound according to the invention:

Example VIII: Preparation of S, S-di (tert-butyl) ethylphosphonodithioate

Sodium hydride (3.0 g, 0.125 mol) was suspended in dry tetrahydrofuran (70 ml) at 0 ° C. 2-

Methylpropane-2-thiol (14.1 ml, 0.125 mol) was then added dropwise over 15 minutes, keeping the temperature below 5 ° C. The mixture was then stirred at room temperature overnight, after which ethylphos-15 fondichloride (7.35 g, 0.05 mol) in dry tetrahydrofuran (10 ml) was added over 30 minutes, the temperature being below 35 ° C was kept by cooling with a water bath. The mixture was stirred at room temperature for 5 hours and then left overnight.

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Toluene (200ml) was added followed by water (200ml) and the layers separated. The toluene layer was washed with 2N aqueous sodium hydroxide solution (100ml) and water (100ml) then dried, filtered and evaporated to yield S, S-di (tert-25.

butyl) ethylphosphonodithioate in the form of an oil, (8.72 g) (69% yield).

The structure of the product was confirmed by phosphorus NMR (nuclear magnetic resonance spectrum) (single peak at 65.0 ppm with respect to 85% phosphoric acid), and by proton NMR (tetramethylsilane as internal standard): / singlet at 1.6 ppm / SCfCH 2), two triplets at 1.1 ppm and 1.3 ppm (P-CH 2 CH 3) and a multiplet at 2.2 ppm (P-CH 2 CE) 7 y-. ... f Ί

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Integration of the proton magnetic spectrum was consistent with the depicted structure.

The following example illustrates preparations according to the invention: 5

Example IX

A granulated preparation of: S, S-di (tert-butyl) ethylphosphonodithioate ................. 10% w / g propylene glycol ........... .............................. 5% w / w. | Q attapulgite granules of 0.295 / 0.701 mm ..... ............ 85% w / w was prepared by mixing the S, S-di (tert-butyl) ethylphosphonodithioate and propylene glycol and spraying the mixture through a flat fan nozzle with a 2 bar pressure on the attapulgite granules while mixing in a horizontal drum mixer. After all of the liquid had been sprayed onto the granules, mixing was continued for about 10 minutes until the liquid was completely absorbed and the granules were homogeneous. The granules thus obtained can be applied in an amount of 3 kg per ha to 2q a place affected by Diabrotica spp, to control these species.

Granules containing 20% w / w S, S-di (tert-butyl) ethyl phosphonodithioate can be prepared in a similar manner.

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Claims (6)

1. S, S-Di (tert-butyl) ethylphosphonodithioate. 2. Method for controlling insects and nematodes, characterized in that S, S-di (tert-butyl) ethylphosphonothioate is applied to the insects and nematodes or to their environment. Process for controlling rootworm, characterized in that S, S-di (tert-butyl) -ethylphosphonodithioate is introduced into the soil. 4. Insecticidal or nematocidal action composition, characterized in that it comprises S, S-di (tert-butyl) ethylphosphonodithioate in a dosage form suitable for such use. 5. A composition according to claim 4, characterized in that it comprises an inert, non-cytotoxic organic solvent and / or a solid carrier. 6. Process for the preparation of S, S-di (tert-butyl) ethylphosphonodithioate, characterized in that an ethylphosphonhalide of the general formula CH ^ C ^ -Pi ^ O) (-X) -Xj, wherein X is a halogen atom and X ^ 20 represents a halogen atom or a tert-butylthio group, react with two molar equivalents of 2-methylpropane-2-thiol if X1 represents a halogen atom, or one molar equivalent of 2-methylpropane-2-thiol as X- | represents a tert-butylthio group in the presence of a base. 25