JPH0465043B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention comprises at least one macrolide compound selected from B-41 group antibiotics, C-076 group antibiotics, and 22,23-dihydro C-076 group derivatives, and a compound represented by the following general formula (). The present invention relates to an acaricidal composition containing at least one compound as an active ingredient. (In the formula, X represents an oxygen atom or a sulfur atom,
Y represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, or a halogen atom). B-41 group antibiotics are Streptomyces spp.
-41-146 strain (deposited with the Institute of Microbial Technology, Agency of Industrial Science and Technology as Microbiology Research Institute No. 1438)
It includes compounds isolated from cultures of and having the following formula or the structural formula.

【table】

[Table] A ₁ , A ₂ , A ₃ , A ₄ , B ₁ , B ₂ , B ₃ of B-41 above,
C ₁ and C ₂ and the acaricidal uses of these compounds are described in JP-A-50-29742, and compounds with α and β numbers are described in J. Antibiotics 29(3), 76-14~
76-16 and 76-35 to 76-42 of the same magazine 29(6). Further, B-41D and its acaricidal use are described in JP-A-56-32481, B-41E and F and their acaricidal use are described in JP-A-57-77686, and B-41G and its acaricidal use are described in JP-A-57-77686. is published in Japanese Patent Application Publication No. 1987-
It is stated in Publication No. 120589. The B-41 group antibiotic is the B-14-146 strain (the mycological properties of which are described in JP-A No. 50-29742), which have been conventionally used to culture Streptomyces bacteria. The culture medium, under aerobic conditions, approx.
After culturing at 28°C for 5-10 days, the culture was separated with diatomaceous earth, and the resulting cake was mixed with methanol and then n-
Extract with hexane to obtain an oily substance, which is then fractionated by applying it to a silica gel column. C-076 group antibiotics and 22,23-dihydro C
The -076 group derivatives include compounds having the following structural formula.

【table】

[Table] The above C-076 group antibiotics are Streptomyces avermitilis C-076.
Obtained from a culture of the production bacterium (NRRL8165),
Antimicrob.Agents Chemother, 15, (3), 361~
367 (1979), and its acaricidal use is
Abstr.150.Progr.Abstr.53rd Annu.Meet.Am.
As stated in Soc.Parasitol.76. 22,23-dihydro C-076 derivatives and their production method are disclosed in Japanese Patent Application Laid-open No. 1983
-Described in Publication No. 61198. In the general formula (), when Y is a lower alkyl group, a lower alkoxy group or a halogen atom, they are preferably a methyl group, a methoxy group or a chlorine atom, respectively. Among the compounds having the formula (), particularly preferred compounds are as follows. The numbers assigned to each compound are referenced in the description below. (1) 3-cyclohexylcarbamoyl-4-methyl-5-phenyl-2-oxazolidone (2) 3-cyclohexylcarbamoyl-4-methyl-5-(4-methoxyphenyl)-2-oxazolidone (3) 3-cyclohexyl Carbamoyl-4-methyl-5-(4-methylphenyl)-2-thiazolidone(4) 3-cyclohexylcarbamoyl-5-(4
-chlorophenyl)-4-methylthiazolidone All of the above preferred compounds are trans-forms, and the method for producing the compound of formula () and its acaricidal use are disclosed in JP-A-56-51463 and JP-A-57-50982. It is stated in the No. By the way, the Tetranychus and Panonychus genera are representative types of spider mites that cause great damage to agricultural crops. Representative examples of Tetranychus include the two-spotted spider mite, Kanzawa spider mite, and false red spider mite; representative examples of the Panonychus genus include the orange spider mite and the apple spider mite. The antibiotics according to the invention are not necessarily effective against all developmental stages of any species. In other words, B41 group antibiotics are effective against two-spotted spider mites at all stages of development, but they are less ovicidal against orange spider mites, and C-076 group and
The 22,23-dihydro C-076 group antibiotics have high larvicidal properties, but generally have poor ovicidal properties against all types of spider mites. Furthermore, when all of the antibiotics described here are sprayed alone on plants in the field, they easily decompose on the plants and lose their effectiveness. Therefore, in controlling the orange spider mite, it is possible to rapidly reduce the density of spider mites immediately after spraying, but the disadvantage is that the larvae that hatch from eggs survive and the density recovers quickly. Also, for two-spotted spider mites, if the spraying is not uniform and there is no direct contact with the chemical during spraying, C-076, which has poor ovicidal properties, may be used.
group, 22,23-dihydro C-076 group as well as B41
Similarly, group antibiotics cannot be expected to have a long-term density suppression effect with rapid density recovery. On the other hand, the compound of the general formula () has high efficacy against eggs, larvae and nymphs of mites, but
Not effective against adult insects. Therefore, it is not possible to rapidly reduce the growth density of spider mites immediately after spraying, which becomes the source of the next generation of mites, and it cannot be expected to suppress the density over a long period of time. Therefore, even with the compound of formula (), in order to have a residual effect on the eggs laid by adult insects that survived after spraying, or the larvae that hatched from these eggs, it is necessary to treat the compound at a high concentration. , not economical. As a result of various studies, the present inventors have found that when the above-mentioned macrolide compound and the compound of formula () are used together, an unexpectedly high degree of synergistic effect is exerted in suppressing mite density over a long period of time. They discovered this and completed the present invention. The above-mentioned macrolide compounds are known to act as neurotoxins, and this is thought to be the reason for their high adulticidal activity. moreover,
The same compound is also known to inhibit chitin synthesis (J. Antibiotics, 1984, 37 , 797-801).
Therefore, it acts not only as a neurotoxin but also as a growth inhibitor against the stage before the mite becomes an adult, that is, the larva or nymph, and as a result of these actions, acaricidal activity is expressed. It is thought that the On the other hand, as mentioned above, the compound of formula () is
Since it is specifically effective only against eggs, larvae, and nymphs, it is thought that the acaricidal activity is expressed through some sort of growth-inhibiting effect. The acaricidal composition of the present invention does not simply compensate for the difference in activity due to the difference in the stage of the mites with both drugs in a complementary manner, and therefore does not exhibit an additive effect; It shows an unexpectedly high synergistic effect that far exceeds the expected effect. Although the reason for such a synergistic effect is not clear, it is presumed that it is the result of the interaction of the mechanisms of action of the above-mentioned drugs. Such a synergistic effect is observed in a wide range of blending ratios of both drugs, and when the compound of formula () is added in an amount of about 0.1 to 10 parts by weight, and in addition about 0.5 to 5 parts by weight, per 1 part by weight of the macrolide compound. It is most strongly expressed in ratio. The most preferred combination of both drugs is that the macrolide compound is B-41α ₁ (A ₃ ), B-41α ₃ (A 4 ), B-41α 3 (A ₄ ),
-41D, C-076B _1a , C-076B _1b or 22, 23-
dihydro C-076B _1a or B _1b , and the compound of the above formula () is a compound
This is a case where either (3) or (4) is true. The acaricidal composition of the present invention can be prepared by mixing at least one of the above-mentioned compounds with a suitable carrier or diluent and, if necessary, usual adjuvants commonly used in acaricides, to form an emulsion. It can be prepared into various dosage forms such as wettable powders, powders, and flowable preparations. Suitable liquid carriers include mineral oil, petroleum, kerosene, xylene, cyclohexane, cyclohexanone, dimethylformamide, dimethyl sulfoxide, alcohols, acetone, water, etc., and solid carriers include vegetable powder, kaolin, bentonite, etc. , acid clay, talc, diatomaceous earth, alumina, activated carbon, etc. are suitable, and one or more of these may be used. Auxiliary agents include various types of surfactants. For example, nonionic surfactants (polyoxyethylene alkylaryl ether, polyoxyethylene sorbitan monolaurate, etc.),
Cationic surfactants (alkyldimethylbenzylammonium chloride, alkylpyridinium chloride, etc.), anionic surfactants (alkylbenzenesulfonates, ligninsulfonates, higher alcohol sulfates), amphoteric surfactants (alkyldimethylbetaine, dodecylaminoethylglycine, etc.). These adjuvants may be used alone or as a mixture of two or more. It is also possible to mix and use other active ingredients such as herbicides, insecticides, and fungicides that do not impair the activity of the composition of the present invention. In particular, even greater effects can be expected by incorporating machine oil. Next, the composition of the present invention will be specifically explained by giving formulation examples and test examples. All parts in the text indicate parts by weight. Formulation Example 1 B-41α ₃ (A ₄ ) 1 part Compound No. 3 1 part Xylene 40 parts Dimethylformamide 40 parts Paracol KPS (emulsifier, trade name) 18 parts The above ingredients were uniformly mixed and dissolved to obtain an emulsion. Formulation example 2 B-41α ₁ (A ₃ ) 1 part Compound No. 2 5 parts Mineral oil 30 parts Silicic anhydride 26 parts Sodium dodecylbenzenesulfonate 8 parts Siegrite 30 parts The above are mixed uniformly and crushed to form a wettable powder. I got it. Test Example 1 A comparison test was conducted on the control effects of the combination product of the present application and each single agent against citrus spider mites at the Miyagawa Wase Unshu tangerine orchard for 7th grade students. That is, a chemical agent diluted to a predetermined concentration was uniformly sprayed on a tangerine tree using a power sprayer. 50 per tree just before spraying and every week after spraying
Leaves were randomly sampled and female adult insects living there were counted. The test was conducted in two consecutive sessions with one tree and one section. In addition, the control efficiency for 4 weeks (refer to Research on Drug Resistance of Fruit Tree Spider Mites, Plant Protection Association (1984), p. 3) was determined. The results are shown in Table 1.

【table】

[Table] Test Example 2 A tangerine seedling with 20 leaves left was inoculated with 5 female adult citrus spider mites, left for 2 days to lay eggs on the leaves, and then the female adults were removed. Five other female adults were inoculated on the fifth day from the first inoculation date (second inoculation), and the female adults were removed two days later. Similarly, a third inoculation (5 female adults) was performed on the 12th day from the first inoculation date, and the female adults were removed 2 days later. In this manner, on the 14th day from the first inoculation date, nymphs, hatched larvae, eggs just before hatching, and eggs just after spawning remained on the leaves, but no adult females were present. On the 14th day after the first inoculation, the tangerine seedlings were uniformly sprayed with the chemical using a small power sprayer. After treatment, the mandarin orange seedlings were left in a greenhouse for 3 weeks, after which the surviving female adults were counted. Each test group was tested in triplicate, and the effectiveness of the drug was calculated using the following formula. Effectiveness (%) =
Number of female adults in untreated area - Number of female adults in treated area/Number of female adults in untreated area x 100 The results are shown in Table 2.

[Table] As is clear from Test Examples 1 and 2 above,
It can be seen that the combination formulation of the present invention has synergistically enhanced efficacy against adult insects and efficacy against eggs, larvae, and nymphs compared to each single formulation.

Claims (1)

[Scope of Claims] 1 At least one macrolide compound selected from B-41 group antibiotics, C-076 group antibiotics, and 22,23-dihydro C-076 group derivatives, and the following general formula () At least one of the compounds represented by
Acaricidal composition containing seeds as an active ingredient: (In the formula, X represents an oxygen atom or a sulfur atom,
Y represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, or a halogen atom). 2 The compound of general formula () is 3-cyclohexylcarbamoyl-4-methyl-5-phenyl-2
-Oxazolidone, 3-cyclohexylcarbamoyl-4-methyl-5-(4-methoxyphenyl)
-2-oxazolidone, 3-cyclohexylcarbamoyl-4-methyl-5-(4-methylphenyl)-2-thiazolidone or 3-cyclohexylcarbamoyl-5-(4-chlorophenyl)-4
- The acaricidal composition according to claim 1, which is the trans isomer of methyl-2-thiazolidone. 3 The macrolide compound is B-41α ₁ (A ₃ ),
The acaricidal composition according to claim 1, which is B-41α ₃ (A ₄ ) or B-41D.