JPS61194092A - S,s-di(tert-butyl)ethylphosphonodithioate - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to S,S-di(tert-butyl)ethylphosphonodithioate, insecticidal compositions containing it as an active ingredient, and its use as an insecticide and nematocide. It concerns something.

The compound of the present invention has the formula: CH3CH2-P(=(3)[-3
C(CH3)3]1 (Formula 1), it exhibits a wide range of activities as an insecticide and nematocide, and has excellent stability, especially in soil.
ty) and long-term residual activity (Iona residuala
1 activity).

The compounds of the invention can be used, in particular in agriculture, against adults, larvae and eggs of the butterfly moth 1111 Q (Leaidopte'ra), such as: for example,
Ieliothis Vi
reSCenS ) (tobacco budworm
), Heliothis armigera (tleiothis
armigera) and Heliothis zea (Heli
Heliothis species, such as Othis zea),
Exempta (S, e■7), Nis litoralis (S,
1ittoralis) (Egyptian c.
cottonworm).

Nis eridania (S, eridania) (
Spodoptera species such as southernarmyworn+).

Hamestra: Configurata
Conrig Wangdan A) (Bertha Arllywo)
rm) ; Earias species 1 such as E, 1nsulana > (Eg
yptian bol1born+), Pcctinophora.

Species 1 For example, Bekujinohora gossiibiera
european cornborcr), Trichoplusia ni
(cabbage Ioper), vinylis (Pie
ris) species (Cabba(le '1ions), Rafigma species (ariywora+s),
jrotis (A! jrotis) and amate (A! jrotis)
cutworms.

One, Wiseana species (porina)
moth), Chilo species (rice 5)
tes borer), Tripoliza (LD) Uni B
'-) species and Diatraea species (s
sugar cane borers and rice bo
rers), Subarganodis bileriana (Spar
anthis pilleriana ) (ora
pe berry moth), Shigia bomonella (C
idta polon+311a) (codlin
g 110th), fruit trec tortrix moths
), Plutella xii 1] Stella (Plutella x
phantom jl punishment upper loe) (diamond back n+o
th). Similarly, for example, Hibotenemus hampei (coffee b)
erry borer), Hylesinus
us) species (bark beetles), Anthonomus grandi
s) (cotton boll weevil).

cucumber bee
tles).

Lema species, Thyriodes species.

Leptinotarsa decemlineata (1eptinot)
arsa decemlineata ) (Colo
rado potato bee mouth 0).

DiabrOtiCa species (c
orn r, ootwormS), gonocephalum (falsewire worms)
, Agriotes species (wireworms)
, Darmole ida, Rebigiota (Kaikuchi Ako V'-) and Heteronicus (He
ter.

(formerly W te arubs), fu? Edon・
Cochleariae (Phaedon cochleari)
ae ) (mustard beetle), Listurhobutrus oryzophyllus (rice *ater weevi
l), Melligetis species (pOIIen b)
eetleS), Sectorhy
nchus) species, Rhynchophorus (Rhynchol)
)horus) and Cosmobolites (Cosmopo
I ites ) species (root weevils)
; Sitona species (1) ea and b
ean WeeVilS), Coleoptera (C
It can be used against adults and larvae of A. oleoptera (beetles). For example, Sipe (ps
ylla) species, Beiisia species, Aphis species, Mizus species, Hegoura viciae
, Phylloxera species,
Adelges (^de1ges) species.

7 as Phorodon humuli
) (hoDdamson aphid), Aeneolamia sp., Nephotettix sp. (rice1e)
af hoppers), Emboas power (n 肚且)
)seed.

Nilaparvata species, Perkinsiel Ia species, Virilla (
b'yu1su,) seeds.

Aonidiella species (red 5)
cales), -Uchucus (COCCus) species, Pseudococcus (Pseud.

coccus) species, Heropertis species (
mosquito bugs), Lygus
) species, Disdercus (1ydanwata! 工 sJ''-) species,
Oxycarenus (■■arenus) species, Nezara (5c
zara) Species-like Hemiptera
; Athalia species and Ceph7s (
ttymcnoptera such as Cephus species (saw flies) and tear cutting ants; Species and cololobus (ch+.

shoot Hies, leaf m1ners, fruit
Diptera, such as Flies; Thysanoptera, such as Tribus tabaci; Thysanoptera, such as Locusta and Schi
5 tocerca locusts.

Crickets such as Gryrus
Gryllotalpidae (Gryllotalpidae) and Gryllotalpidae (
Orthoptera (mole crickets)
hOptera): Sm1nthur
us) species and Onychilarus species (spri
Collembola (Collemb. ngtaiIs)
ola); Odontotermes
es ) species (ters+1tes) of Isoptera (t
soptera) ;Forficara (Forf icu
Ia) species (earwigs)-like Hymenoptera (Dc
rvaptcra) and agriculturally important arthropods (art
hropods), such as Tetranicus
ychus) species, Panonycus species and Bryobia species (LJdany0tech) species (spiderlt).
es), Er1ophyes species (
gallmites), Polyphagotarsones (P
olyl hagotarsonen+us) Species: Blaniulus Seeds (mill)
ipcdes), Scuti erre
lla) species (symphilids), oniscus (O
niscus) species (wo.

dlice) and Triobus (J) species (crustac
ea)-like mites (Acari) (n+1tes),
Furthermore, nematodes that are harmful to plants, such as cystic nematodes (CySt nematodes), parasitize both roots and young shoots (shoots).
latodes) (heterodera (t(eteroder)
a) species, Globodera species), root-knot neIllatodes
) (Lesion nellatodes)
(Prat 1enchus species), daoaer nen+atodes
) (Xifinema species) and small nematodes (eelworms) that parasitize stems and bulbs (
It can be used against Ditilencus (Fujiangumi Hus species).

Corn root rotter (Diabrotica)
The compounds of the invention are of particular interest for the control of corn rootworm due to their good activity against corn rootworms (Ttca) species and their long residual activity in the soil. As shown in Example 1 below, the duration of residual activity of the compounds of the present invention against corn root rot in soil is unexpectedly superior to the duration of residual activity of compounds with related chemical structures. It is something that

(Margin below) Example 1: 1 ri The test compound has the following formula:

R(X)P(=X')(X2R')(X3R2) (I
A) AEt-OSt-Butyl St-ButylBEt
-O3n-propyl S 〃CEt-OSiso-S
〃 Propyl Dot-O3iso-S 〃 Butyl [[t-08n-Butyl S 〃FHe-O3n
-Propyl S GEt-5St-butyl 0
Iso-propyl HEt-3St-butyl Ol-butyl TEt00
St-butyl St-butyl JEtOO3t-butyl S 5ec-butyl compound Compound A is a compound of the present invention.

B is No. of U.S. Patent No. 4,472,390;
This is the compound No. 2.

C is No. of U.S. Patent No. 4,472,390;
7 compound.

O is No. of U.S. Patent No. 4,472,390,
This is the compound No. 9.

E is No. of U.S. Patent No. 4,472,390;
10 compounds.

F is No. of U.S. Patent No. 4,472,390;
There are 12 compounds.

G is Example 8 of U.S. Pat. No. 4,268,508
It is a compound of

11 is a compound A compound described in US Pat. No. 4,268,508.

1 G; tPcT W Permit It l No 83100
No. 8870 (7) Compound No.

It is 11.

J is compound No. of PCT patent application No. 10831008870.

It is 10.

The soil used was clay foam containing approximately 23% moisture by oven dry weight (samples were
(Determined by drying at 110°C for 4 hours). All rates for treatments with test compounds were expressed in parts per billion (ppg+) of oven dry weight of soil.

Prior to treatment with test compounds, the soil was passed through a 3.511 m hole screen. 0.1 to 0 when an amount of solution 11Ii is added to a soil sample equal to 100 g oven dry weight.
．． 5 ppm, 0. Test compounds were dissolved in dimethyl ketone to give a test compound concentration of 5 ppm O.

A soil sample equal to an oven dry weight of 5005F was placed in a polyethylene bag and 5 d of a test compound solution in dimethyl ketone containing the desired concentration of test compound was added. The bag whites were then thoroughly mixed. The bag was then opened for 1 hour to allow dimethyl ketone vapor to dissipate.

Immediately remove the soil sample from the bag using DiabrOtiCaun.
decimpunctata) (day 0). Pour the remaining soil into a sealed brown glass jar.
After storage at 4°C and treatment with the test compound, further samples were removed and tested on 7th, 14th, 21st, 28th, 42nd, 56th, 70th, and 84th days. . Note that the soil was remixed before taking out the sample.

Activity against corn caterpillars was determined as follows.

Corn caterpillars were reared on maize seeds (SeedlingS) at 25°C.

2.5- distilled water and roots were well developed and sprouted (St)
Approximately 20 g of treated soil was placed in a 25X75 wrapped glass vial containing corn seeds.

Five 5-day-old corn caterpillar larvae were placed on the soil, and those that did not burrow into the soil after a few minutes were replaced, until all the larvae were buried in the soil. I did it like that. The tube (vial) was covered with a wire mesh lid and maintained at 25° C. for 4 days. Each treatment was repeated four times up to the 42nd day, and twice on the 56th, 70th, and 84th days. After 4 days, the samples were examined, the number of dead and live larvae were counted, and the average larval mortality was calculated from the four replicate treatments compared to the untreated control.

Those exhibiting an average percentage of 90 or higher are those with a satisfactory level of larval control of corn diabrotica species.

The results obtained are shown in the surface finish and Table 3 below.

From the above results, the following was clarified.

(1) 0. At a concentration of lppm, compound ^ is compound B
provided a satisfactory level of control of corn diabrotica larvae over 6 times longer than that of the present invention.

That is, Compound A showed a satisfactory level of inhibition until day 42, whereas Compound B could no longer provide a satisfactory level of inhibition after 1 day. 5x concentration (0
, 5 ppm), Compound B
It became impossible to provide a satisfactory level of suppression during the day. Furthermore, Compound A provided satisfactory levels of inhibition up to day 14, even at concentrations as low as 0.05 ppi. On the other hand, like Shinki, compound B was unable to provide satisfactory suppression at 78 points even at double concentration (0.1 ppm).

■ At a concentration of o, ippm, Compound A provided satisfactory levels of corn sheet caterpillar control over six times longer than Compound C. That is, while compound provided satisfactory levels of inhibition until day 42, Compound C failed to achieve an average percent mortality of 90% by day 78. Even at half this concentration (0.05 ppm),
Compound A gave satisfactory results up to day 14, while compound C did not achieve this level even at day 08.

■ Even at a concentration of o, 5pp-, compound 0 is 28
Compound A was unable to provide satisfactory control of corn sheetworm larvae by day 11 (11J), whereas in contrast Compound A was found to be at one-fifth the concentration (0.1 ppn+
) gave satisfactory inhibition for twice as long, up to 42 days. 0. At a concentration of lppm, the compound is θ
On the other hand, the compound ^ gave satisfactory inhibition at this concentration until day 42, and at one-fifth the concentration (0.05 pp
Even in m), satisfactory suppression was given up to the 141=lth point.

(4) By day 7, at a concentration of 0.5 ppm, Compound F was no longer able to provide a satisfactory level of control of corn caterpillars, whereas at a concentration of one-fifth (0.1 ppm) ), compound ^ provided satisfactory inhibition for more than 6 times as long, up to day 42. Compound^, at 0.5 ppm, exerted an inhibitory effect for up to 14 days, twice as long as that which could be achieved with compound [. 0
．． At a concentration of 1 ppa+, Compound F showed little activity even on day 0.

On the other hand, 0. At a concentration of lppm, Compound A is 42
A satisfactory level of inhibition was given up to the 14th day, and even at half the concentration (0.05 ppm), a satisfactory level of inhibition was given up to the 14th day.

■ At a concentration of 0.5 ppm, Compound F was no longer able to provide a satisfactory level of control of corn caterpillar larvae by day 14, whereas at a concentration of 5° lower (0, 101) rA) gave satisfactory inhibition to the compound for at least three times as long, up to day 42, and even at one-tenth the concentration (0.05 ppm), the compound showed satisfactory inhibition up to day 14. It gave a satisfactory suppression that lasted twice as long. At a concentration of 0°lppm, the compound
Satisfactory suppression levels were not achieved even on day one. On the other hand, at this concentration, Compound A gave a satisfactory level of inhibition until day 42, and even at half that concentration (0,0
Even at a concentration of 5 ppm), a satisfactory level of inhibition was achieved until the 14th day.

■ 0.5 ppm of either Compound G or Compound 11
At concentrations of + and 0.1 pp-, even No. 08 did not provide satisfactory levels of corn caterpillar caterpillar control. On the other hand, Compound A was only one-fifth of the highest concentration (0.1 ppm) of Compounds G and H tested (0.1 ppm).
) and 1/10 (0.05 ppm) gave satisfactory levels of inhibition until day 42 and day 14, respectively.

At a concentration of ω O,ippm, Compound I was unable to provide a satisfactory level of control of corn caterpillar larvae even on day 0. On the other hand, at this concentration, compound A gave satisfactory inhibition until day 42, and even at one-fifth the concentration (0.05 ppm), compound A gave satisfactory inhibition until day 14. gave.

At 0.5 pps 1 degree, Compound I was no longer able to provide a satisfactory level of inhibition by day 56, whereas at this concentration, the compound provided satisfactory inhibition until day 84, with one-fifth of the Even at concentrations (0.1 ppm), 5
It gave satisfactory inhibition for a period comparable to that obtained with double the concentration (0.5 ppm) of compound ①.

(8) Even at a concentration of 0.5 ppm, Compound J was no longer able to provide a satisfactory level of control of corn caterpillar larvae by day 14. on the other hand,
Compound A at one-fifth of the concentration (0.1 ppm) gave satisfactory inhibition at least three times as long, up to 42 days, and 1
At one-tenth the concentration (0.05 ppm), Compound A gave a satisfactory level of inhibition that lasted twice as long, up to 14 days. 0. At a concentration of 1 ppm, Compound J fails to give satisfactory inhibition even on day 0, while at this concentration Compound A gives satisfactory inhibition until day 42, with a fifth The concentration of (0,051) Elm
) gave satisfactory suppression until the 14th day.

■ 0. At a concentration of 1 ppm, the compound has a 0.1 ppm concentration until at least day 42. It provided satisfactory control levels of corn caterpillar caterpillars for more than 6 times the longest duration of the comparison compounds (compounds B and C) at lppm. Compounds B and C, at this concentration, are no longer able to provide satisfactory levels of control of corn grubs by day 7 - the seven universal comparison compounds are no longer able to provide satisfactory levels of control of corn grubs even at day 0. It also did not give a satisfactory level of inhibition.

@0.1ppm (7) Concentration Nickel 21.2Lt3
From the results shown in Table I, regarding the average percent mortality of corn sheet metal caterpillars obtained in order D42B, 2
On day 1 Compound A is 6 times more active than Compound C and 9 times more active than Compound Ri, and on Day 28 Compound A is 9.5 times more active than Compound C and Compound It was 19 times more active than 4242, and seven other compounds had ceased to be active by that date, while 4242
It can be seen that by day 42, all nine comparison compounds had lost activity by day 42, whereas the compounds exhibited an average percent mortality of corn sheet caterpillars of 90%. The results in Tables 1 and 1 demonstrate that the compounds were effective both in terms of persistence of satisfactory levels of control of corn sheet metal caterpillars and in terms of activity against cane rootworm at specified times after application of the test compound. clearly shows that it has unexpected and substantial advantages over the other nine comparison compounds. This is particularly well demonstrated when considering the results obtained at a test compound concentration of O,lppm, at which
Compound C) gave a satisfactory level of control of sorghum rootworm until at least day 42, while one of the comparison compounds, compound C), was able to provide satisfactory control on day 14 at this concentration. One of the comparison compounds (Compound B) was no longer able to provide satisfactory inhibition on day 78, and the remaining seven compounds were unable to achieve satisfactory inhibition even on day 0. Ta. 5
Even at twice the concentration (0,501) l), only two comparison compounds (compounds C and
(0.1 pp ■) gave satisfactory inhibition for the same or slightly longer period of time as indicated; again, compounds C and ■ were no longer able to give satisfactory inhibition by the 56th day. , while the compound ^ is 8 at a concentration of 0.5 ppm.
Satisfactory control was given on the fourth day and above. Example 2 below
7 further details the valuable properties of S,S-di(tert-butyl)ethylphosphonodithioate (Compound A) as an insecticide and nematocide.

,titx: Sorghum Sorghum Suppression When drilling seeds into the soil of a small area of a corn field infested with corn sheet caterpillars, 1.
Compound A, formed into 0% granules, was applied in the form of a band. The corn plants are later handled and their roots are placed on a conventional root rating scale (root rating 5ca).
le) (where 6.0 is the maximum pest infection of 1.
(0 indicates no visible damage), the damage caused by the corn sheet metal worm was evaluated. The application rates shown below are for Compound A (Ig/ha). I got the following results.

Application rate Root rating (K/ha Liha compound AA B CD O1842,12,2' 2.1 1.8 2.05
G, 5B 2.6 2.1 2.4 1.9 2
．． 250.28 2.8 2.8 2.9 2.3
2.70 Unprocessed 5.9 5.9
4.9 3.6 5.08 Control The lower root rating obtained for the compound in comparison to the untreated control indicates that this compound has high efficacy against corn sheet metal caterpillar.

When sowing seeds, use 20% granules (aranu).
le) Infecting seed corn maggots with Compound A formed into a strip or in-furrow of the soil in a small area of a corn field, resulting in an application rate of Compound A of 1.12 to 9/ha. It was applied as follows. Seed tow, sorghum (Hillemia black: HVIellia)
The treatment effect on I) latura was later determined by counting the number of fly ants along the length of a row of samples. The number found in the treated subarea was recorded as a percentage of the number found in the untreated control area. The following results were obtained.

Compound A Ant control found (1°12
Kg/ha) percentage banding treatment
15 Sushi white treatment 30 Compound A decreased by 85% and 10%, respectively.
showed high activity against seed corn maggots.

Example 4: Mole cr in soil (turf)
Gr 1 lota (Gr 1 lota) was applied to the compound formed into granules at an application rate equivalent to 5.6 and 11.2 Aig/ha of Compound A, respectively.
It was applied to lawns infected with L.I.D. The number of mounds created by the insect was recorded at the treatment front;
The following results were obtained.

Mound number Compound A (Kg/ha) 5.6 11.2 Untreated control Before treatment 1
3.8 After 7.3 processing 2.8
8.3 Before processing 1G, 3 15.0 After processing
1.5 17.0 The significant decrease in the number of mounds from before to after treatment indicated that Compound A was useful for suppressing mole keratin.

Compound A, formulated into 10% granules, was administered to small areas infected with bean weevil and pea weevil in the soil of a bean field at the beginning of spring, at a rate of IN9/h, respectively.
Two trials were carried out at comparable rates of 1.5 Ky/ha and 2 Ky/ha.

Test 1 was repeated 4 times and test 2 was repeated 3 times in the subarea.

After about seven weeks, the plants were uprooted and the number of weevil larvae attached to the roots was counted. The results are expressed below as the average percent reduction in larval numbers compared to untreated control plants.

Compound^ % reduction in larval numbers (Kg/ha) Test 1 Test 22
90.2 92 1 53, 3 93°75 In particular, the large increase in the number of larvae caused by Compound A obtained at the application rate of 27rg/ha in Tests 1 and 2 and the application rate of IK9/ha in Test 2 The reduction indicates that this compound is effective against bean weevil and pea weevil.

The compound was dissolved in acetone and a certain amount of soil was treated with this solution to obtain a known concentration of the compound in the soil. After evaporating the solvent, the treated soil was loaded into glass jars (approximately 1103 soils per jar). Twenty jars were prepared for each concentration. Then add canefight gloves to each jar (Video French: Le 1d
iota rrenchi) 1/3 instar (insta
The larvae of r) were collected. After 28 days, the mortality rate of the larvae was measured and the following results were obtained.

Application rate to compound corrected with control (rI
tg/K9 soil) Mortality rate mo, 5
47 1.0 89 2.0 95 4.0 100 8.0 100 The obtained results show that Compound A has strong insecticidal activity against cane phytograb.

LMJJU: -,” a) Dit Ienchus
di S cello-) (Small nematode that attaches to stems and roots) Greenhouse nematode 7) Lt 7 Full 77
a; 1ucerne plant). Two to three months after the initial infection, the plants were cut and the nematode eggs and larvae collected therefrom were soaked in water and washed. After sieving, an inoculum suspension containing approximately 150 larvae per d was prepared using distilled water.

Equal amounts of uncontaminated soil and river sand, which had been sieved into particles with a size of 1 to 2 ml, were mixed. To this batch of soil was added the compound previously dispersed in distilled water via Tween 80 to dilute the chemical to the required range in the soil.

Plastic plant pots with a capacity of 200 d were partially filled with untreated coarse sand, and 100 alfalfa seeds per pot were sown on top. The pots were then filled with chemically treated soil. However, untreated soil was used as a control. A 5- nematode suspension was poured into 8 pots, giving about 750 larvae to 8 pots. The pots were kept at optimal humidity for seeds to germinate and plants to grow.

After 12-14 days, alfalfa seeds were harvested and examined for infection with nematodes. The effect of each treatment was measured as a percent reduction compared to the untreated control. The following results were obtained in the two tests.

Application rate of compound compared to control 7, - Yay, decrease (/(g/ha
) Test 1 Test 2 (-'' indicates not tested) b) Root-knot nematode (Root-knot nematode)
matode) (meloidcine incognita; (He
roidogyneincO(lnita)' was reared on tobacco plants in a greenhouse. A standard root-knot nematode inoculum suspension containing about 1500 eggs per d of distilled water was prepared from the washed, macerated and sieved roots. At least 10-15% of the eggs are embryonic larvae (embryon 1cIar
val) stage.

The soil prepared for the test consisted of a hand mix of equal parts river sand, beet and uncontaminated soil. 11 to this
Enough egg suspension was inoculated to give approximately 30,000 eggs per soil. The compound was dissolved in acetone and absorbed into Attacla V, and then the acetone was removed by evaporation. Other than untreated control soil,
The soil batch was mixed by hand with the treated Attaclay to ensure the desired range of dilution of test chemicals in the final soil batch.

Two pots were filled from each soil batch.

This was poured with water and maintained in a humidified atmosphere for 21 hours.

Small tomato plants (Harmande) 2
The books were transplanted into 8 pots. This was maintained in the greenhouse for an additional 4 weeks.

The plants were harvested and washed to determine the percentage reduction in root galling. The following results were obtained in two tests.

Application rate of compound^ compared to control 1<-1>Kehler reduction (N9/
ha) Test 1 Test 2 (II II does not indicate that it has not been tested.) The above results indicate that the compound has high level activity against Ditilencus jibusashi and Meloidoscine incognita. Ta.

The compounds of the invention can be prepared in a manner known per se (
By "methods known per se" herein are meant methods used hitherto or described in the chemical literature). Preferably, the compounds of the invention are prepared starting from ethylphosphonic acid halide. Ethylphosphonic acid halide is reacted with 2-methylpropane-2-thiol in the presence of a base to obtain the compounds of the invention.

According to a feature of the invention, the compound of formula (■) has the formula: CHCH
-P(=(3)(-X)-X' (Formula II) [wherein, X
represents a halogen atom, preferably chlorine, ×1 halogen atom, preferably chlorine, or a tert-butylthio group [5
When Xl is a halogen atom, generally 2 mol equivalent of 2-methyl-propane-2-thiol and Xl are te
The rt-butylthio radical is generally prepared in a process that involves reacting one molar equivalent of 2-methyl-propane-2-thiol in the presence of a base or with a thiol alkali metal salt, such as sodium.

The process proceeds according to the following reaction mechanisms Δ and B.

Reaction mechanism A (Xl represents a halogen atom) CH, C
M, -P(=(3)(-X)-X +2CHJC(31
1) (C1 A C ■ 3 (IIA) 2 bases 11-→CH, CH2-P (=0) [-3C (CH3)
3], +2 base HX/HX reaction 1 structure B (X bar 5
C(CI+3)J represents)CH3C12-P(=(3)
(-X)-3C(CH几〇H3C(SH)(CH3
)Cl et al. (IIB) Aim1Ct13CH□-P(=0)[-3C(CH3)3
12 +W=劃IX(I) In the above formula, X and ×1 have been defined so far. The reaction described in Reaction Scheme A is a preferred method for preparing the compound of Formula 1.

The process is carried out at temperatures between about 0 and 100°C between a thiol and an alkali metal, such as sodium, or its halide, or an alkali metal hydroxide.

For example, it is carried out in an organic solvent using an alkali metal salt of a thiol prepared from 1 cum of sodium hydroxide.

Suitable organic solvents include, for example, benzene.

Toluene, cyclohexane, tetrahydrofuran.

These include dimethylformamide, 2-butanone and acetone (dimethylketone).

Compounds of formula (1) can be prepared by methods known per se. For example, the compound of formula
S), vol. 28, pp. 2522-2526 (1978
), Chemistry Letter (Chcn+1stry L
Pianfetti and Quin.

Journal of the American Chemical Society (J, Amer, Chell, Soc,
), Vol. 84, p. 851 (1962).

Compounds of formula IrB are disclosed in British Patent Application Publication No. 208789/
It can be prepared by the method described in No.A. 2-methyl-
Propane-2-thiol was prepared by Dobbin, J. Chew, Soc. 5
It can be prepared by the method described in Vol. 7, p. 641.

The compounds of the invention are effective as insecticides and/or nematicides at low concentrations. Direct application of this compound alone is generally impractical since it has an inhibitory effect in small amounts. Therefore, the compound is compatible (comp
agriculturally acceptable diluent or carrier and/or surfactant (i.e., suitable for use in insecticide or nematicide compositions in the art and compatible with the active ingredient). of S,S-di(tert-butyl)ethyl phosphonodithioate, preferably homogeneously dispersed in combination with is desirable.

Application compositions containing the compounds of the invention as active compounds may preferably be dispersions or emulsions containing from about 0.001% to about 1x to about . Since the active compound is substantially water-insoluble, an inert, non-phytotoxic (non-phytotox+c) organic solvent is added thereto, preferably so that the active compound is present at a concentration of about 2x to about 75% w/
It is desirable that the concentration be such that it can be rapidly dispersed in an aqueous medium to form a homogeneous dispersion of the active compound for application. The composition usually also contains a surfactant. For example, an active liquid composition can be prepared using the active compound, acetone or ethanol, and Tween 20 (polyoxyethylene sorbitan monolaurate) or any other suitable surfactant.

The composition containing the active compound can also be solid, for example in powder or granule form. For example, the active compounds are kaolinite (niao++n+te), bentonite.

Mixed with a suitable solid carrier such as talc or the like or mineral clays such as attapulgite, montmorillonite, diatomite or sepiolite.
+011te). Powder compositions containing from about 0.5% to about 25% W/W of the active compound and granular compositions containing from about 1% to about 25% of the active compound are preferred.

The active compound may also contain other insecticidal ingredients, such as insecticides,
Nematicides and fungicides, such as thiophanox (th
iofanox), carbofur
an), aldicarb and benomyl.

For the control of insects and nematodes, the active compound is usually applied to the area where it is desired to prevent their infection at a dosage of approximately
, iKy to about 25 Kg. Under ideal conditions, lower application rates may provide adequate protection depending on the pest to be controlled, whereas in adverse weather conditions,
Depending on pest resistance and other factors, it may be necessary to use larger proportions of the active ingredient.

If the pest is soil-borne, the active compound-containing agent is distributed evenly over the area to be treated by any known method. If desired, it can be applied generally to fields or areas where crops are grown, or in the vicinity of plants or species to be protected from infection. The active ingredient can be washed into the soil by water application over the area or can be left to the natural action of precipitation. During or after application, if desired, the agent may be applied mechanically in the soil, for example by plowing or plowing.
discing) Lt can be dispersed. Application is before sowing,
This can be done at the time of sowing, after sowing, or before or after germination.

The following examples detail the preparation of compounds of the invention.

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

2-Methyl-propane-2-thiol (14,1111
0.1251101) was added dropwise over 15 minutes while maintaining the temperature below 5°C. The mixture was then stirred at room temperature overnight. Next, ethylphosphophone R2 chloride (7,3
5-g, 0.05 mol) in dry tetrahydrofuran (10 d) for 30 min and cooled in a water bath.
Addition was made while maintaining the temperature below 5°C. The mixture was stirred at room temperature for 5 hours and allowed to stand overnight.

Add toluene (200m), then water (200m)
was added and the layers were separated. The toluene layer was washed with a 2N aqueous sodium hydroxide solution (100 m) and water (100 m),
Dry, soak, and evaporate to form an oily S,S-di(te).
rt-butyl)ethylphosphonodithioate (8,12
9, yield 69%).

The structure of the product was determined by phosphorus-NMR (6 to 85% phosphoric acid).
5. Single beak on Opp) and proton NMR
(Tetramethylsilane as internal standard) [Singlet, 1. lppm and 1.6ppH [5C(CH,
3) 3), 2 triplets, 1.1pDI,
1.3 DDll (P CH29 days) and Multib L, tt, 2.2 pDll (P-OH2CH3)]
confirmed by. Integration of proton NMR results confirmed the structure as described.

The following examples are illustrative of compositions of the invention.

Example 9 A granule composition comprising S,S-di(tert-edge)Lt)ethylphosphonodithioate 10% Ill/W propylene glycol 5% w/w attapulgite 24/48 mesh particles 85% w/w , S,S-di(tert-butyl)ethylphosphonodithioate and propylene glycol and this was applied to attapulgite particles at a pressure of 2 bar through a flat-fan nozzle while mixing in a horizontal drum blender. It was prepared by spraying. After all of the liquid was sprinkled onto the particles, mixing was continued for approximately 10 minutes until the liquid was completely absorbed into the particles and the particles were homogeneous. The particles thus obtained are corn worms;
It can be applied to control sites of infection with Diabrotica species at a rate of 3Ks/ha.

Granules containing 20% w/w S,S-di(tert-butyl)ethylphosphonodithioate may be similarly prepared.

Claims (5)

[Claims] (1) S,S-di(tert-butyl)ethylphosphonodithioate. (2) A method for controlling insects and nematodes comprising applying an insecticidal amount of S,S-di(tert-butyl)ethylphosphonodithioate to the insects and nematodes or to their habitat. (3) A method for controlling corn rootworms, which comprises supplying an insecticidal amount of S,S-di(tert-butyl)ethylphosphonodithioate into soil. (4) A composition comprising an effective amount of S,S-di(tert-butyl)ethylphosphonodithioate as an insecticide or nematocide, and an inert organic solvent or solid carrier that is not harmful to plants. (5) General formula: CH_3CH_2-P(=O)(-X)
-X^1 [In the formula, X represents a halogen atom, X^1 represents a halogen atom or a tert-butylthio group] When X^1 represents a halogen atom, 2 molar equivalents of the ethylphosphonic acid halide When X^1 represents tert-butylthio, 1 molar equivalent of 2-methane-propane-2
- S comprising reacting a thiol in the presence of a base,
A method for producing S-di(tert-butyl)ethylphosphonodithioate.