JPS5940156B2 - New imidazothiazolium salts - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION This invention relates to new imidazothiazolium salts of value as nematicides.

That is, the general formula 4 Θ □ (]) C=Y (wherein, R represents a lower alkyl, lower alkenyl or phenyl group, X represents...a rogen atom, Y represents an oxygen atom or a sulfur atom, - --1 indicates a saturated bond or a double bond.

) provides novel imidazothiazolium salts represented by:

These compounds are 6-phenylimidazo[2,1-b
] A derivative having an ionic structure derived from thiazoles, 4Θ □ (■) (wherein, X represents a halogen atom, and 1-1 represents a saturated or double bond.

) and RNCY(■) (wherein, R represents a lower alkyl, lower alkenyl or phenyl group, and Y represents an oxygen atom or a sulfur atom.

) in a suitable solvent at 20-150°C.
Preferably, it is synthesized by reacting at 30 to 100°C.

The solvent used is dimethyl sulfoxide, dimethyl formamide, etc., which do not participate in the reaction, and the reaction is completed in several hours at most.

The reaction products are recovered by standard methods. That is, if the product is precipitated from the solution at the end of the reaction, it is collected by filtration, and if the product is dissolved, the product is collected by distilling off the solvent under reduced pressure. Next, a specific synthesis example will be shown.

Synthesis example 1 2,3,5,6-tetrahydro-6-phenylene
iN-Methylcarbamoyl)imidazo[2,1-b]thiazolium chloride (A) 2,3,5,6-tetrahythro-6-phenylimidazo[2,1-b]thiazolium chloride 6.0f7 (0.024m01 ) for 40m
1 dimethyl sulfoxide, and 2.17 (0.036 m01) of this solution was added dropwise.

After the dropwise addition, the mixture was stirred at 80°C for 3 hours, and then the solvent was distilled off under reduced pressure. The remaining transparent oil eventually crystallized, which was washed with acetone and collected by filtration, and then recrystallized with isopropanol to produce crystals with a yield of 4.5y (yield 63%) and a melting point of 239-24FC (decomposed). I got it. Elemental analysis value Calculated value as Cl3Hl6N3ClOS (%) C1
: 11.90; S: 10.76 Experimental value (%) Cl: 1
1.77; S: 10.65 Synthesis example 25,6-dihythro-6-phenyl-methylthiocarbamoyl)
Imidazo[2.1b')thiazolium chloride (B)
5,6-dihythro 6-phenylimidazo [2,1-b
] Thiazolium chloride 7.07 (0.029m01
) was dissolved in 50ml dimethyl sulfoxide, and this solution was dissolved in 2.9y petatylthioisocyanate (0.04m01
) was added dropwise.

After the dropwise addition, the mixture was stirred at 80° C. for 3 hours and then cooled, and the precipitated crystals were filtered out. By recrystallizing this with ethanol, the yield was 8.17 (yield 90%) and the melting point was 179-181℃.
(Decomposition) White crystals were obtained.

Elemental analysis value Calculated value as Cl3Hl4N3ClS2 (
%) C1: 11.37; S: 20.56 Experimental value (%)
Cl: 11.31; S: 20.70 Synthesis example 35.6
-Dihythro-6-phenylated Jyo-iN allylthiocarbamoyl)imidazo[2.1-b]thiazolium chloride (05.6-dihythro-6-phenylimidazo[2.
1-b] Thiazolium chloride 6,07 (0.025
m01) in 40ml dimethyl sulfoxide, and to this solution was added allylthioisocyanate 2.57 (0.02
5m01) was added dropwise.

After the dropwise addition, the mixture was stirred at 80° C. for 3 hours, and then the solvent was distilled off under reduced pressure. The remaining oil eventually crystallized and was washed with acetone and filtered to obtain crystals with a yield of 5.27 (62% yield) and a melting point of 164°C (decomposed). Elemental analysis value Calculated value (%) as Cl, Hl6N3ClS2 C
l: 10.49; S: 18.98 Experimental value (%) Cl
:10,19:S:18,77 Synthesis example 45,6-dihythro6-phenyl-JyoiN methylcarbamoyl)imidazo[2,1-b]thiazolium chloride (T)5
・6-dihythro 6-phenylimidazo [2.1-b]
Thiazolium chloride 7.0y (0.029m01)
was dissolved in 50 ml of dimethyl sulfoxide, and this solution contained 2.87 (0.052 m01) of petatilysocyanate.
was dripped.

After the dropwise addition, the mixture was stirred at 50°C for 3 hours, and then the solvent was distilled off under reduced pressure. Crystals of 8.27 were obtained, and by recrystallizing them from isopropanol, white crystals with a yield of 70y (82% yield) and a melting point of 191-2°C (decomposed) were obtained.

Elemental analysis value Calculated value as Cl3Hl4N3ClOS (
%) CI: 11.98; S: 10.84 Experimental value (%
) Cl: 11,86; S: 10.69 Synthesis example 55.
6-Dihydro 6-phenylated (Phenylcarbamoyl)-imidazo[2.1b]thiazolium chloride (P5.6-Dihydro6-phenylimidazo[2.
1-b] Thiazolium chloride 6.0y (0,025
m01) in 40 ml dimethyl sulfoxide, and this solution hephenyl isocyanate 3.07 (0.025
m01) was added dropwise.

After the dropwise addition, the mixture was stirred at 60°C for 3 hours, and then the solvent was distilled off under reduced pressure. The residue was recrystallized with isofukomapanol to obtain crystals with a yield of 3.2y (yield 36%) and a melting point of 124-5°C (decomposition). Elemental analysis value Cl8Hl6N3Cl
Calculated value as OS (%) Cl: 9.91; S: 896
Experimental values (%) Cl: 9.75; S: 8.80 A. B. C.D. A test was conducted to confirm the effectiveness of nematocide on the new imidazothiazolium salts of E.

That is, each test drug is made into an aqueous solution with a predetermined concentration, and 20 ml of the obtained drug solution is divided into a diameter of 9.5 CTr and a height of 1.5 cTr.
Transfer to a L petri dish and add Panagrellus S to this.
A solution containing approximately 500 PP (self-active nematodes) was injected, and the number of dead insects was measured at regular intervals.

The results are shown in the table below. As shown in the table, These imidazothiazoliu All the salts showed good insecticidal properties.

Claims (1)

[Claims] 1 General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (In the formula, R represents a lower alkyl, lower alkenyl, or phenyl group, and ----- represents a saturated bond or a double bond.) A novel imidazothiazolium salt represented by