JPH07165514A - Composition for preventing withering of pines and prevention method - Google Patents

Abstract

PURPOSE:To obtain a composition for preventing the withering of pines caused by pine wood nematode by using an LL-F28249 compound having strong nematocidal action against pine wood nematode as an active component. CONSTITUTION:This composition for preventing the withering of pines contains an LL-F28249 compound expressed by the formula [R1 is H or CH3; R2 is CH(CH3)2 or CH3; R3 is =NOCH2 or OH) as an active component. The compound of the formula is preferably moxidectin, nemadectin, LL-F28249beta (both R1 and R2 are CH3 and R3 is OH), LL-F28249gamma (both R1 and R2 are CH3 and R3 is OH], LL-F28249X [R1 is CH2, R2 is CH(CH3)3 and R3 is OHI, etc., especially preferably moxidectin. The composition can be produced by dissolving the compound of the formula and a surfactant in a watermiscible solvent and adding water to the solution. The composition has improved water solubility of the compound of the formula to get high dispersibility of the compound in a tree. The solvent to be used in the process is e.g. methanol, ethanol and ethylene glycol.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a composition for preventing pine wilt damage caused by pine wilt disease, and also relates to a method for preventing pine wilt death using the composition.

[0002]

2. Description of the Related Art Pine nematode disease, a pine tree nematode disease that causes discoloration of the pine needles from summer to early autumn, and reddens the entire canopy about one month later, causes death. (Bursaphelenchus xylophilus) (hereinafter abbreviated as nematode) is considered to be the pathogen. In addition, this nematode is a kind of long-horned beetle, Monochamus alt.
ernatus) (hereinafter abbreviated as chamomile). From mid-May to the end of July, the sword beetle that emerged and escaped from the pine nematode disease-damaged trees of the previous year has a healthy young pine branch that holds thousands to tens of thousands of nematodes on its body and on its surface. Is eaten after (feeding for maturation). At this time, the nematode leaves the body of the chamomile and penetrates into the pine tree from the site where the chamomile was injured by ingestion and propagates.

A pine infested with nematodes exhibits an appearance of wilting symptoms in 2 to 3 months, and leaves discolor. A tree whose leaves have started to change color is called an abnormal tree.
After mating to leave offspring, laying eggs on this abnormal tree and eventually the abnormal tree dies. On the other hand, in healthy trees, the eggs of the sword beetles that are laid cannot be hatched because they are wound on the resin of the pine, and the larvae that have hatched die while being wound on the resin while feeding under the bark of the tree. . But,
Eggs of the beetle laid on an abnormal tree or dead tree weakened by the invasion of nematodes hatch without being wrapped in resin, and the larvae grow while feeding under the bark.

The fully-grown scabbard larvae protect the body from low temperatures in winter by forming a pupa chamber deep in the pine tree for the purpose of overwintering from late autumn to early winter. When the temperature rises in spring, the larvae of the beetle that wintered in the pupa chamber become pupae, and eventually emerge as adults and escape from dead trees. At this time, the nematodes gathered around the pupa chamber transfer to the emerged chamomile and are carried away from the dead tree along with the chamomile. The nematode escapes from the body of the chamomile and invades the pine tree while the chamomile carrying the nematode post-feeds on the healthy pine shoots. Eventually, this pine exhibits wilting symptoms, and the leaves begin to discolor. In this way, pine wilt disease spreads pine wilts one after another.

The following methods ((1) to (4)) are used to prevent the pine wilting from being damaged by the pine wilt disease.

(1) Extermination of larvae of chamomiles Before the emergence of chamomiles, extermination is mainly performed in the larval stage. The habitat of chamomile larvae is limited to dead trees, and the chamomile larvae can be exterminated by felling, peeling, incinerating or treating the dead trees with chemicals.
Examples of the chemical treatment include a method of spraying an organophosphorus insecticide and a carbamate insecticide, or a method of fumigation using a carbam chemical. Furthermore, methods for utilizing insect parasitic microorganisms and predatory natural enemies are being studied.

(2) Prevention of aftergrowth of adult sorghum C. Infestation of nematodes can be prevented by preventing aftergrowth of adult sorghum. For this purpose, the insecticide is sprayed before the emergence of the sword beetle, which is sprayed from the ground or from the air by a helicopter.

(3) Method of preventing death by treatment with single tree chemicals Before nematode infection is expected, nematodes are injected by injecting a nematicidal agent into pine trees or applying it to soil. It is a method of directly exterminating. Currently, mesulfenphos, morantel tartrate, and levamisole hydrochloride are used as agents for tree trunk injection. Ethyl thiomethone, methomyl, aldeikarub, etc. were effective as soil application agents, but none of them has been put to practical use.

(4) Breeding of resistant pine In order to create a resistant pine that does not die even when infected with nematodes, selective breeding, cross breeding, expression of induced resistance by attenuated nematodes, etc. have been studied. Although these methods have been gradually successful, they are expected to take considerable time to be technically established.

[0010]

Each of the techniques for controlling pine wilt disease described above has advantages and disadvantages. Regarding felling, peeling, incineration, and chemical treatment for the purpose of exterminating larvae of beetles, there is a problem because the labor force necessary for thorough treatment is insufficient. In addition, although the preventive spraying of insecticides for the purpose of preventing post-feeding of adult shavings is an effective control method, its implementation is subject to various restrictions depending on the surrounding conditions.

[0011] The treatment of a single tree with a trunk injection agent involves spraying an anti-posterior drug of kamikiri such as shrines, large trees in temples or parks, pine trees in urban areas, or pine trees in general gardens, which are important for environmental preservation. This is an effective method that has been implemented in difficult places and when there is a possibility of infection even after preventive spraying. However, they still have problems in terms of occurrence of phytotoxicity due to tree trunk injection, stability and sustainability of effects, and further investigation is required. Therefore, the object of the present invention is to
It is an object of the present invention to overcome the above problems and provide a composition for preventing damage to pine trees with stable effects.

[0012]

As a result of intensive studies to solve these problems, the present inventors have found that the LL-F28249 compound of the following structural formula has a strong insecticidal activity against pine wood nematodes. I found something.

[0013]

[Chemical 3]

[0014]

[Chemical 4]

LL-F2824 used in the present invention
Examples of the 9-based compound include the above compounds, and among them, moxidectin is particularly preferable. The composition for preventing pine wilting of the present invention is a composition containing the compound as an active ingredient, which is injected into a tree trunk and translocated in the tree, whereby the infected nematode acts in the tree. It can be killed before the start to prevent the death of pine trees.

LL-F2824 used in the present invention
Nine compounds are Streptomyces cyaneogriseus sp. Noncyanog, a fungus isolated and cultured from South Australian soil.
LL-F28249, which is a metabolite produced by enus.
The milbemycin-based compound having acaricidal activity produced by a bacterium different from the above bacterium is clearly different. LL
-F28249 compounds are known to be effective for treating and preventing parasitism in animals including humans, but moxidectin, a derivative of nemadectin (LL-F28249α), is used as a prophylactic agent for canine heartworm. Has been done. However, there is no finding that the LL-F28249 compound was used to control pine wilt disease to prevent pine tree death. On the other hand, all of the LL-F28249-based compounds have very low solubility in water, so even if they are dissolved in an organic solvent and injected into the pine tree, the dispersibility in the tree is poor and there is a problem with the nematode exterminating effect. was there.

The composition of the present invention improves the solubility of the LL-F28249 compound in water and facilitates the injection into the pine tree, and makes the compound well dispersed in the tree and stable. It is effective in exterminating the disease. The composition of the present invention contains LL-F28249-based compound as an active ingredient, and is composed of at least one of water or / and a solvent, a surfactant and the like, or a combination thereof.

The solvent used in the composition of the present invention may be one that is easily miscible with water. For example, methanol,
Lower alcohols such as ethanol, polyhydric alcohols such as ethylene glycol, propylene glycol, diethylene glycol, 1,3-butylene glycol, isoprene glycol, polar solvents such as acetone, acetonitrile, tetrahydrofuran, ethylene glycol monomethyl ether, etc. Glycol ethers,
Examples thereof include glycol esters such as ethylene glycol monoacetate and dioxane.

Surfactants used in the composition of the present invention include, for example, anionic sulfates such as alkyl sulfates, alkane sulfonic acids, alkylbenzene sulfonic acids, alkyl phosphates, N-acyl sarcosine salts, N-acylalanine salts and succinates are alkylamines as cationic surfactants,
Alkyltrimethylammonium salts, dialkyldimethylammonium salts, alkyldimethylbenzylammonium salts and alkylpyridinium salts are used as nonionic surfactants in polyoxyethylene castor oils, polyoxyethylene hydrogenated castor oils, polyoxyethylene alkyl ethers, polyoxyethylene alkyl ethers, and polyoxyethylene alkyl ethers. Oxyethylene alkyl phenyl ethers, polyoxyethylene alkyl phenyl ether formaldehyde condensates, polyethylene glycol fatty acid esters, polyoxyethylene polyoxypropylene alkyl ethers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, polyoxyethylene sorbitol Fatty acid esters, polyglycerin fatty acid esters, sucrose fatty acid esters and propylene Glycol mono fatty acid esters are further amino acids as amphoteric surface active agent, there is a carboxy betaines and sulfobetaines and the like.

Further, it is an essential requirement that a nonionic surfactant be contained as a surfactant, and among the above nonionic surfactants, polyoxyethylene hydrogenated castor oils, polyoxyethylene alkyl ethers, polyoxy Particularly preferred are ethylene polyoxypropylene alkyl ethers, polyoxyethylene sorbitan fatty acid esters, polyoxyethylene sorbitol fatty acid esters, polyglycerin fatty acid esters, and sucrose fatty acid esters.

The amount of each component of the composition of the present invention can be appropriately changed, but the active ingredient (LL-F28249 type compound) can be adjusted to 0.
1 to 50% by weight, preferably 1 to 10% by weight, surfactant 1 to 50% by weight, preferably 1 to 20% by weight, water 10 to 80% by weight, preferably 10 to 70% by weight, solvent It may be contained in an amount of 10 to 80% by weight, preferably 10 to 70% by weight. Further, the respective components of the composition of the present invention can be compounded by any method,
For example, when the solubility of the active ingredient in water is improved by a method of adding water after dissolving the active ingredient and the surfactant in a solvent, the composition of the present invention having excellent dispersibility in a tree can be easily produced. can do.

When applied to pine trees, the application rate of the composition of the present invention can be appropriately changed depending on the purpose, time, tree age and damage condition. For application, a method of boring a hole in the trunk of a pine tree and injecting the composition of the present invention through the hole can be employed.

[0023]

EXAMPLES Next, the contents of the present invention will be specifically described by way of examples, but the present invention is not limited to these.

Example 1 (Anti-pinewood nematode activity test) LL-F2824
Among the 9 compounds, moxidectin was tested for anti-nematode activity by the following method. In order to compare the compound of the present invention with the anti-nematode activity, morantel tartrate,
A similar test was conducted for mesulfenphos, levamisole hydrochloride and control. Table 1 shows the test results
Shown in.

Test Method On the entire surface of the potato dextrose agar medium in a petri dish,
Botrytis cinerea flora was formed and used as a test petri dish. 0.15 ml of a drug solution having a predetermined concentration was added to a cotton ball placed in the center of the test petri dish, and a pinewood nematode suspension (10000 heads / ml) was added to 0.15 m.
1 and then incubated at 25 ° C for 5 days and then B
The area of the food scar portion of the otrytis cinerea flora was measured.
The drug solution was prepared by dissolving 0.1 g of the drug in 3 g of POE (50) hydrogenated castor oil and 6 g of propylene glycol,
It was prepared by adding water to 100 ml and diluting it to a predetermined concentration with water.

[0026] For Shokukon portion of the area (S) of the Shokukon portion is circular, measures the diameter (D), was calculated by the equation of S = πD ^2/4. The anti-nematode activity was calculated by the following formula. Anti-nematode activity (%) = 100-area ratio (%) of the scar portion to the inner area of the petri dish

[0027] The control is a solution obtained by removing the drug from the drug solution.

As is clear from the test results in Table 1, the LL-F28249 compound of the present invention exhibits anti-nematode activity at a drug concentration lower than that of the conventional tree trunk injection agents, morantel tartrate, mesulfenphos and levamisole hydrochloride. Was given.

Example 2 (Test for Prevention of Mortality by Pine Seedlings) Among LL-F28249 series compounds, a test for prevention of mortality by pine saplings (5th grade) was conducted on a solubilized formulation and a non-solubilized formulation of moxidectin by the following method. did. As in Example 1, the test was also conducted on morantel tartrate, mesulfenphos, levamisole hydrochloride, and the drug non-injection section. The composition of the injectable preparation is shown in Table 2, and the result of the pine seedling mortality prevention test is shown in Table 3.
Shown in.

Test method [0030] About 2 weeks after injecting the formulation of Table 2, the formulation of morantel tartrate, the formulation of mesulfenphos and the formulation of levamisole hydrochloride into the pine tree, a highly toxic pine tree nematode (S6-
1) 1 ml of a suspension (10000 heads / ml) was inoculated, and the effect of preventing mortality was determined after about 2 months.

[0031] * HCO-40: POE (40) hydrogenated castor oil

[0032] Morantel tartrate formulation: Greenguard Eight (Pfizer Pharmaceuticals Inc.) Mesulfenphos formulation: Nemanone injection (Nippon Bayer Agrochem) Levamisole hydrochloride formulation: Century Injection (Hodogaya Chemical Co., Ltd.)

As is clear from the test results of Table 3, the solubilized preparation of the LL-F28249 compound of the present invention is a lower drug than the non-solubilized preparation of the compound, the morantel tartrate preparation, mesulfenphos and levamisole hydrochloride preparation. The amount of pine saplings was found to be effective in preventing mortality.

[0034]

INDUSTRIAL APPLICABILITY The composition of the present invention exhibits excellent anti-nematode activity at a low dose as compared with other tree trunk injection preparations (for example, morantel tartrate, mesulfenphos and levamisole hydrochloride). It is extremely effective for the death of pine trees caused by insect diseases. Also, the composition of the present invention is LL-F2824.
Since the solubility of the 9-based compound in water is improved, the medicinal effect of the compound can be spread in the pine tree body, and the pine tree can be effectively prevented from being damaged by pine nematode disease. Furthermore, since the method for preventing pine tree death according to the present invention is carried out by injecting an effective amount of the LL-F28249-based compound into the trunk of a pine tree and transposing it into the tree, nematodes can be easily exterminated.

Claims (6)

[Claims] 1. LL-F28 represented by the following structural formula:
A composition for preventing pine damage, which comprises a 249-based compound as an active ingredient. [Chemical 1] [Chemical 2] 2. The composition for preventing death of pine trees according to claim 1, wherein the LL-F28249-based compound is moxidectin. 3. The LL-F28249 compound according to claim 1 and a surfactant containing a nonionic surfactant are dissolved in a solvent miscible with water, and then water is added to the compound. A composition for preventing pine tree death, which has improved water solubility and is excellent in dispersibility in a tree. 4. A polyoxyethylene hydrogenated castor oil, polyoxyethylene alkyl ether, polyoxyethylene polyoxypropylene alkyl ether, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene sorbitol fatty acid as the nonionic surfactant. The composition for preventing pine damage according to claim 3, which comprises at least one selected from the group consisting of esters, polyglycerin fatty acid esters and sucrose fatty acid esters. 5. The solvent miscible with water is methanol,
Containing at least one or more selected from the group consisting of ethanol, ethylene glycol, propylene glycol, diethylene glycol, 1,3-butylene glycol, isoprene glycol, acetone, acetonitrile, tetrahydrofuran, dioxane, glycol ethers and glycol esters. The composition for preventing pine tree death according to claim 3 or 4. 6. A pine tree nematode (Bursaphelenchus xylophil) is injected into a trunk of a pine tree by injecting an effective amount of the composition for preventing pine tree death according to any one of claims 1 to 5 and transposing into the tree body.
us)), a method for preventing the death of pine trees.