JPS58113111A - Agent and method for exterminating bursaphelenchus lignicolus - Google Patents

Abstract

PURPOSE:To provide an agent for exterminating Bursaphelenchus lignicolus, containing a specific organophosphoric acid ester derivative as an active component, suitable for injecting into the trunk, capable of migrating rapidly in the tree, giving no phytotoxicity to the pine tree, and having low toxicity to man and animal. CONSTITUTION:The agent for exterminating Bursaphelenchus lignicolus contains the organophosphoric acid ester derivative of formulaI(R is 1-4C alkyl; R1 and R2 are H, 1-3C alkyl or phenyl, provided that R1 and R2 are not H at the same time), e.g. the compound of formula II, as an active component. The agent is applied to pine tree by injecting into the trunk. In addition to the excellent exterminating effect of Bursaphelenchus lignicolus, the compound has excellent residual effect, and prevents the withering of pine trees for at least 3 years after injecting into the trunk. The compound of formulaIcan be prepared by reacting the compound of formula III with the compound of formula IV.

Description

[Detailed Description of the Invention] The present invention relates to a drug and a method for killing pine nematode, which causes the rapid death of pines such as red pine, black pine, and ryukyu pine. . More specifically, a pine tree nematode killer characterized by containing an organophosphoric acid ester derivative represented by the following general formula [υ] as a ringing component, and a drug containing the active ingredient are applied to pine trees by trunk injection. The present invention relates to a method for killing pine tree nematode, which is characterized in that the method is applied to.

However, in the formula, R represents a lower alkyl group having 1 to 4 carbon atoms or a phenyl group.

In recent years, pines all over Japan have been suffering from widespread damage, with everything from young trees to old trees rapidly withering and dying. It has become clear that the cause of the rapid withering and death of these pines is due to the pine nematode, which is transmitted by the pine beetle.

Since then, research has been carried out on various methods to prevent pines from dying under these circumstances, such as prevention of withering through chemical treatment, purple testing for natural enemies, and selection of seedlings resistant to pine nematode. There is. Among these methods, methods for preventing the death of pines by chemical treatment include methods such as aerial spraying of preventive agents on living trees and chemical treatment of dead trees to kill the pine tree beetle, which transmits the pine tree nematode, Methods for killing pine tree nematodes include injecting chemicals into tree trunks and treating soil. Each of these methods has its advantages and disadvantages, and it is necessary to decide which method to use by taking into account the growing location of the pines, the age of the trees, the damage situation, the life history of the pine beetle, etc. The method of aerial spraying of preventive chemicals allows a wide area to be treated with chemicals in a short period of time, but on the other hand, there is a risk of destroying the natural ecosystem. In addition, the chemical treatment of dead wood is a method of killing the larvae of the pine beetle that has penetrated deep into the bodies of pines that have died due to the pine tree nematode. However, it is often ineffective, and it is nearly impossible to cut down all the dead pines and treat them with chemicals. Next, in the earthen treatment method, the amount of chemicals applied is large, approximately 1.5 to 5.0 kg per living tree, which is extremely uneconomical, and the northern part of the country is highly polluted. It is thought that. On the other hand, injecting chemicals into the trunks of living trees has a very low possibility of environmental contamination due to the chemicals, and the amount of chemicals applied is sufficient to kill the pine tree nematodes living or attempting to live inside the pine trees. It is sufficient to use the minimum number of plants required to prevent the plants from withering and dying, and it is an economically very advantageous method. This drug for tree trunk injection has an excellent pine nematode killing effect, and when applied to the trunk of a pine tree, it quickly migrates throughout the tree and does not cause any chemical damage to the pine trees to which it is applied. It is required to have a residual effect of at least 2 to 3 years and to have low toxicity to humans and livestock.

Unfortunately, however, there has been no known agent for tree trunk injection that is effective in preventing pine tree blight and satisfies all of the above conditions. For example, fensulfothion and thionazine, which are known to be effective as pine needle nematode killers, have extremely high human susceptibility.

An object of the present invention is to provide a pine nematode killer that kills pines, and a method for killing pine nematode to advantageously kill pine nematode.

The present inventors are conducting research to prevent the blight of pines, particularly by injecting chemicals into the tree trunks to kill the pine tree nematodes that live or attempt to live in the pines. I've been going there for many years. As a result, it was discovered that the compound represented by the general formula CI) kills the pine tree nematode and is highly effective in preventing the withering of pines. Moreover, the compound represented by the general formula (1,1) is
It was found to be significantly less toxic than previously known agents for tree trunk injection (such as fensulfothion and thionazine). The compound represented by the general formula (1) is a compound disclosed in West German Patent No. 115,624, but it was not known at all that this compound was effective in killing pine nematodes. The present inventors have discovered that by injecting the compound into the trunk of a pine tree, the compound quickly moves within the pine tree, kills the pine nematode, and prevents the pines from dying. I discovered that it is possible. Furthermore, it has been discovered that in addition to the vague pine tree nematode killing effect, this compound exhibits good residual efficacy and can prevent pines from dying mainly for 2 to 6 years even without tree trunk injection treatment. Therefore, the drug containing the compound represented by the general formula (1) as an active ingredient has the performance required as a drug for tree trunk injection, that is, it has a high pine tree nematode killing effect, and it has a high level of nematode killing effect. It fully satisfies the requirements of rapid migration, no chemical damage to the pines to which it is applied, and low toxicity to human stands, making it extremely useful as a chemical for preventing the blight of pines. be.

The compound represented by the general formula CI, 1 is described in MfJ West German Patent No. 115. /+24 by the following method.

However, in the formula, R, RI, and R2 are the same as those shown in the above formula (1), and M represents a paulownia atom such as sodium or potassium.

Approximately 1% of the compound represented by the general formula CI, ) is used as an active ingredient.
It contains up to 100% by weight, preferably 10 to 100% by weight. In the method for killing pine nematode of the present invention,
When applying the compound represented by the general formula CI) to pines by trunk injection method, the active ingredient (100% by weight of active ingredient), or the active ingredient in a solvent and/or surfactant at a convenient concentration for injection. It can be diluted and injected.

As a solvent, water, an organic solvent such as n-hexane,
Aliphatic hydrocarbons such as petroleum ether, aromatic hydrocarbons such as toluene and xylene, dichloromethane, 1
-Halogenated hydrocarbons such as 1,1-trichloroethane and chlorobenzene, alcohols such as methanol and ethanol, ketones such as acetone and isophorone, diethyl ether, dipropyl ether, and dioxane'-7''class゛';i+lL'*kh7game'
yl 6 amides, sulfoxides such as dimethyl sulfoxide, nitrites such as acetonitrile, etc. can be used, and these can be used alone or in combination of two or more. In addition, as a surfactant, use one type or a mixture of two or more of anionic surfactants, anionic surfactants, nonionic surfactants, and zwitterionic surfactants. can do.

Forms of preparations include aqueous solutions, wettable powders, oil solutions, and emulsions.

For the tree trunk injection method, inject into the tree trunk with a diameter of 2 to 20 mm and a depth of approximately 1.
The dropper injection method involves drilling a ~10cm hole and injecting the chemical solution into the hole using a dropper, or the chemical syringe method, which involves inserting the mouth of a container containing the chemical solution into the hole. , the ampoule syringe method, in which a hole with a depth of 5 to 10 cm is made, an ampoule containing a drug solution is inserted into the hole, and the ampoule is destroyed in the hole, a drop injection method, a mechanical press-in method, etc. The whole tree trunk can be used for injection.

When applying the pine tree nematode killer of the present invention to pines, the purpose, location, time, and tree age should be considered.

Determine the amount of medicine needed by fully considering the damage situation in the surrounding area, etc. For example, the amount of active ingredient applied per one pine tree can be exemplified as 1 to 500 ml.

EXAMPLES Next, the content of the present invention will be specifically explained with reference to Examples, but the following description is not intended to limit the present invention.

Example 1 Compound No. 1 of the present invention (see Table 1 below) (ampule with 50% acetonitrile <7aa) was injected into a black pine tree about 10 years old using an ampoule syringe for trunk injection. Two to six injection holes were made in the diameter tree and the mixture was injected into the pine tree.

Example 2 Raw material 10 of the present invention compound No. 2 (see Table 1 below)
m1 was injected into the pine tree using a dropper after making one or two injection holes in a medium-diameter Japanese black pine tree that was about 10 years old.

Example 3 25 parts of the present invention compound No. 3 (see Table 1 below), 25 parts by weight of methanol, and 50 parts by volume of xylene were added,
300 ml of the well-mixed solution was injected into a large-diameter Japanese black pine tree, about 50 years old, by making 2 to 6 injection holes using a drop injection method.

Next, the efficacy test results and toxicity test results of the drug of the present invention are shown below.

Test 1 A 6-year-old Japanese black pine (diameter at ground level 1.0-1.5 a.m., seedling weight: 100-200 g) was transplanted into a clay pot with a diameter of 24 cm in early spring, and after confirming rooting, in June
11 to N015, and comparative drugs ad to test wood 1.
0.1 g of each drug substance was injected into the trunk of the tree using a dropper injection method. One month after the injection, the tips of the 2-year-old branches of the test trees were cut off, rubber bushings were attached, and 15,000 cultivated pine nematodes were attached to each test tree. The withering situation survey was conducted in Kamitsukuda in November. The results are shown in Table 1.

Table 1 Test 2 Targeting a stand of black pine trees that are 60 years old, with an average tree height of 10 m, and an average diameter at breast height of 10 cm, the test trees that were determined to be healthy by the small circle resin pressure determination method in May 1979 were Invention compounds No. 61 to No. 3, drug substance and comparative drug a
Two injection holes of 50 m and 1% were made for each test tree, and approximately 30,000 pine-nosed nematodes were inoculated per test tree. The withering situation survey was conducted in early November 1979. The results are shown in Table 2.

Test 6 All of the Japanese black pines that survived Test 2 were determined to be healthy trees in June 1980 using the small circle resin pressure determination method. Therefore, for these surviving Japanese black pines, holes were drilled into the trunks at a height of 3 m above the ground, and approximately 30,000 cultivated pine nematodes were grafted onto each test tree. The withering situation survey was conducted in early November 1980. The results are shown in Table 2.

Test 4 In June 1981, all of the Japanese black pines 4d that survived Test 6 were determined to be healthy trees by the small circle resin pressure determination method. Therefore, we targeted the remaining Japanese black pines by drilling holes in the trunks at a height of 6 m above ground and culturing pine wood nematodes at a rate of approximately 30,000 per tree.
Head inoculated. The condition of withering was conducted in early November 1981. The results are shown in Table 2.

Test 5 Table 6 shows the results of the acute oral sex test on mammals.

Table 3 (Note) Compound No. of the present invention, l-Ha, 3 and comparative drugs a and d are the same as in Table 2.

Patent Applicant Nippon Carlit Co., Ltd. (1. Procedural Amendment Written by June 28, 1980 Commissioner of the Patent Office Shima 1) Haruki Tono 1, Indication of Case 1982 Patent Application No. 209585 Pine Tree Nematode Killer and method of killing 5. Person making the amendment 4. Date of the amendment order ``Scope of Claims'' column and ``Detailed Description of the Invention'' column of the specification of the invention.

1. In the "Claims" section of the description of the contents of the amendment, add the following line to the "Invention, except when R1*R2 are hydrogen at the same time."

(Attachment) "Claims" 1. A nematode killer characterized by containing an organic phosphate ester derivative represented by the following general formula as an active ingredient.

In the formula, R represents a lower alkyl group having 1 to 4 carbon atoms, and R1
+ R2 is hydrogen, which may be the same or different, and has 1 carbon number
~3 lower alkyl group or phenyl group.

λ A method for killing pine tree nematode characterized by □ comprising applying a drug containing an organic phosphate derivative represented by the following general formula as an active ingredient to pines by trunk injection method.

In the formula, R represents a lower alkyl group having 1 to 4 carbon atoms, and R1
+ R2 is hydrogen, which may be the same or different, and has 1 carbon number
~3 lower alkyl group or phenyl group.

Claims (1)

[Scope of Claims] 1. A nematode killer characterized by containing an organic phosphate derivative represented by the following general formula as an active ingredient. However, in the formula, R represents a lower alkyl group having 1 to 4 carbon atoms or a phenyl group. 2. A method for killing pine tree nematode, which comprises applying a drug containing an organic phosphate derivative represented by the following general formula as an active ingredient to pines by trunk injection. However, in the formula, R represents a lower alkyl group having 1 to 4 carbon atoms or a phenyl group.