JPH04178362A - Urea derivative and pest controlling agent containing the same - Google Patents

Abstract

NEW MATERIAL:An urea derivative of formula I [A is NR1R2 (R1 is H, alkyl, alkoxy; R2 is alkyl, alkenyl, 4-morpholyl, phenyl, five-membered heterocyclic group having two or three of N and S atoms or benzo-condensed group thereof, nitrogen-containing six-membered heterocyclic group or benzo-condensed group thereof, cyclic amino]. EXAMPLE:3-(1,2,3,4-Tetrahydro-1-naphthyl)-1-(2-methyl-4-quinolyl)urea. USE:A pest controlling agent. The compound of formula I gives no chemical damage to useful crops. PREPARATION:A compound of formula II is reacted with a compound of formula III to provide the compound of formula I.

Description

[Detailed description of the invention] [Industrial application field] The present invention relates to pest control agents.

[Prior Art] A large amount of research has been conducted on urea derivatives useful in agriculture and horticulture, and many compounds with high physiological activity have been discovered and put into practical use.

For example, DCMU, Monuron, Linuron, Daimeron, and the like are known as herbicides. However, little is known about urea derivatives having a tetrahydronaphthyl group. Although there is a description of the herbicidal activity of urea derivatives having a tetrahydronaphthyl group in US Pat. No. 4,005,140, there is no description of the insecticidal or fungicidal activity.

[Problem to be solved by the invention]! ! Horticultural insecticides and fungicides are generally widely used and contribute to plant protection and increased crop production. However, by continuously spraying the same chemical on crops and pests, resistant bacteria and resistant pests spread, reducing the control effectiveness of the chemical and often making it impossible to use it. It's here.

Therefore, the development of a highly practical pest control agent that does not develop drug resistance and exhibits excellent control effects is eagerly awaited. An object of the present invention is to provide a novel pest control agent with high practical value.

[Means and effects for solving the problem] The present inventors have discovered that urea derivatives having a certain substituent have excellent efficacy as pest control agents, and have completed the present invention. .

That is, the present invention relates to the following general formula (I) [wherein A is N
RR (R represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, and R2 is substituted with a lower alkyl group, a lower alkenyl group, a 4-morpholyl group, a phenyl group, a lower alkyl group, a lower alkoxy group, a halogen group, etc.) a 5-membered heterocyclic ring having 2 to 3 heteroatoms selected from a nitrogen atom or a sulfur atom which may be substituted with a phenyl group, a lower alkyl group, or a mercapto group, which may be substituted with a phenyl group, a lower alkyl group, or a mercapto group; lower alkyl group, lower alkylthio group,
Represents a nitrogen-containing 6-membered heterocycle that may be substituted with a \rogen group, etc., and a benzo condensate thereof. ) or represents a cyclic amino group such as a piperidyl group. The present invention provides a pest control agent containing a urea derivative represented by the above general formula (1) as an active ingredient.

Specific examples of the urea derivatives represented by the general formula (I) according to the present invention are shown in Table 1, but the compounds of the present invention are not limited thereto.

The compound (1) in the membrane can be synthesized, for example, according to the reaction formula below.

In the above reaction formula, A in (III) in the membrane represents the same substance as in (1) in the membrane.

The above reaction is carried out in a solvent or without a solvent, preferably at 0.
°C to 150 °C, more preferably 20 °C to 100 °C
This can be carried out by reacting at a temperature of several minutes to 48 hours.

Examples of solvents include aromatic hydrocarbons such as benzene, toluene, and xylene, ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, and diethylene glycol dimethyl ether, acetone,
Ketones such as methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, dichloromethane, chloroform, carbon tetrachloride, dichloroethane, chlorobenzene,
7-logenated hydrocarbons such as dichlorobenzene, esters such as ethyl acetate and butyl acetate, acetonitrile,
Nitriles such as isobutyronitrile, dimethylformamide, dimethyl sulfoxide, etc. are used.

The amount of the reagent used in the reaction is usually 1 to 10 equivalents of the compound of general formula (m) per 1 equivalent of compound (II) in the membrane.
It is equivalent.

The compound of the present invention is effective as an active ingredient of a pest control agent, particularly as a fungicide for agriculture and horticulture, and is effective as a fungicide for rice blast disease (P.
yrtcular4a oryzae), sheath blight (R
hiZOetonia 5OIani), apple powdery mildew (Podosphaera Ieucotric
ha), Venturia 1naequ
alis), pear scab (Venturia na
shieola), Monilia disease (Sclerosini)
a maxi), oyster anthracnose (Gloeospori)
um kaki), Momo Tennenbyou (Sc I ero)
t 1nia cinerea), scabosis (Cla.
dosporium carpophilum), grape gray mold (Botrytis cinerea)
, Elsinoe ampelina ,
Late rot (Glomerella cingulata)
, Cercosporabetic
ola), bean nut brown spot (Cercospor
a arachjdicola), black astringency (Cer.
cospora personata), barley powdery mildew (Erysjphe gramjnis f, s
P. hordei), eye spot disease (Cerc.
osporel Iaherpotriehoides
), Fusarium n1vale
), :I wheat powdery mildew (Erysiphe gr
a+n1nisf', sp, tritici) s
Puccinja recondita
, Pseudoperonospor
a cubenSiS), powdery mildew (Sphaero
theca fuliginea), vine blight (Myc
osphaerella ll1elonis), Botrytis cinerea, Cladosporiumeucumerinu
m), tomato late blight (Phytophthora 1n)
festans), leaf mold (Cladospori
um fulvum), gray mold (Botryti
s cinerea), Spha powdery mildew (Spha
erotheca humuli) - Botrytis cinerea, Erysiphe cjchoracea
rum), ノ(Diplocarpan)
rosae), citrus scab (Elsinoe)
f'awcetit), blue mold (Penjchill)
iulTljtalicum), green mold (Peni
It exhibits excellent effects against pathogenic bacteria such as Cilljum digitatum).

In addition, the compound of the present invention has excellent control effects against insects and mites that are harmful to agriculture and horticulture, such as armyworm, weevils, cucumber beetles, beetles, green peach aphids, and mites such as two-spotted spider mites and spider mites. It also shows excellent control effects against nematodes such as nematodes. The compounds of the present invention can be safely used on useful crops such as rice and wheat without causing any phytotoxicity.

In the pest control agent of the present invention, the urea derivative represented by the general formula (1) can be used as it is, but it is usually mixed with a solid carrier, liquid carrier, surfactant or other formulation auxiliary, It is used in formulations such as wettable powders, emulsions, granules, and powders. These preparations contain the urea derivative represented by the above general formula (I) as an active ingredient in a weight ratio of 0.1 to 99.
．． 9%, preferably 1 to 99%. The solid carrier includes
Kaolin clay, attapulgite clay, bentonite, acid clay, pyrophyllite, talc, diatomaceous earth,
Calcite, corn cob flour, walnut flour, urea, ammonium sulfate, synthetic hydrous oxide, silicon, etc., are finely powdered or granular.Liquid carriers include aromatic hydrocarbons such as xylene, isopropanol, ethylene glycol, and cellosolve. alcohols such as acetone, cyclohexanone, isophorone, vegetable oils such as soybean oil, cottonseed oil, dimethyl sulfoxide, acetonitrile, water, etc.

Surfactants used for emulsification, dispersion, wetting, etc. include alkylaryl sulfonates, dialkyl sulfosuccinates, polyquine ethylene alkylaryl ether phosphate ester salts, alkyl sulfate ester salts, naphthalene sulfonic acid formalin condensation. Examples include anionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene polyoxypropylene block copolymer, and nonionic surfactants such as sorbitan fatty acid ester. Formulation adjuvants include lignin sulfonate, alginate, polyvinyl alcohol, gum arabic, CMC (carboxymethylcellulose), PAP (isopropyl acid phosphate), and the like.

The application amount of the pest control agent of the present invention varies depending on the type of compound used, target pest, outbreak tendency, degree of damage, environmental conditions, dosage form used, etc. When used, the active ingredient should be 0.1 to 5 dazzles per 10 ar, preferably 0.3 to 1 kg.
It is best to choose from a range of. In addition, when used in a final liquid state such as an emulsion or a wettable powder, 0.1 to 1100
00 ppm, preferably from 10 to 3000 ppm.

[Examples] Hereinafter, the present invention will be specifically explained with reference to Examples, but the present invention is not limited thereto.

Example 1 Synthesis of 3-(1,2,3,4-tetrahydro-1-naphthyl)-1-(2-methyl-4-quinolyl)urea (Compound No. 21) 4-Amino-2-methylquinoline 0. 0.52 g of 1.2.3.4-tetrahydro-1-naphthylisocyanate was added to a solution of 47 g dissolved in 15 ml of a mixed solvent of benzene and dimethylformamide with stirring. After the addition, thermal reflux was performed. After the reaction was completed, the reaction mixture was washed with dilute hydrochloric acid, water, and saturated brine. After drying and concentration over anhydrous sodium sulfate, 0.46 g of 3-(1,2,3,4-tetrahydro-1-naphthyl)-1-(2-methyl-4-quinolyl)urea was obtained.

Melting point: 182-184°C IR (KB r, cm-1): 330029
001640'H-NMR (DMSO-dt3, δp
pm): 1.8-2.0 (m, 4H), 2.7-3
．． 0 (m, 5H), 4.9-5.1 (m, LH), 7.
Table 2 shows representative examples of compounds of the present invention obtained by similar methods and their physical properties.

Example 2 (Irrigation agent) 10 parts by weight of the compound (1) of the present invention was added to water as a carrier material.
87.3 parts by weight of Clyte [trade name, manufactured by Kokusui Kogyo Co., Ltd.], 11.35 parts by weight of Neoperex [trade name, manufactured by Kao Atlas Co., Ltd.] as a surfactant, and Tsurupol 800
A [trade name, manufactured by Toho Chemical Industries, Ltd.] is mixed and ground with 1.35 parts by weight to obtain a 10% hydrating powder.

Example 3 (Emulsion) 25 parts by weight of the compound (2) of the present invention, 65 parts by weight of benzene, and 10 parts by weight of Tsurpol 800A as a surfactant were mixed and dissolved to obtain a 25% emulsion.

Example 4 (Powder) 2 parts by weight of the compound (3) of the present invention, ±5 parts by weight of diatoms, and 93 parts by weight of clay are uniformly mixed and ground to obtain a powder.

Example 5 (granules) 10 parts by weight of the compound of the present invention (4) was mixed and pulverized with 50 parts by weight of bentonite, 35 parts by weight of Kunilite [trade name, manufactured by Kokusui Kogyo Co., Ltd.], and 5 parts by weight of Tsurupol 800A as a surfactant. After that, 10 parts by weight of water was added, stirred uniformly, extruded through a sieve hole with a diameter of 0.7+am, and after drying,
Cut into 2 mm lengths to obtain 10% granules.

Example 6 Test of disease control effect on Curly cucumber Seeds (variety: Sumo Hanshiro) were sown in 8 cm x 8 cm plastic pots and allowed to grow for 3 weeks. A hydrating powder prepared according to Example 2 was diluted with water to a predetermined concentration, and 2 ml per pot was sprayed onto the seedlings. After air drying,
Cucumber and diseased bacteria (Psudoperospora c)
ubensis) inoculated with spores at 125°C and relative humidity 1.
It was placed in a constant temperature room for 24 hours.

Thereafter, they were placed in a greenhouse, and 7 days after inoculation, the degree of damage was investigated using the following formula, and the control value was calculated.

Damage level (%) - N N: Total number of leaves examined nO No disease nl: Number of affected leaves with a lesion area rate of less than 25% 02: Number of affected leaves with a lesion area rate of 25 to 50% n3: Lesion area rate 50-75
Number of diseased leaves in % n4: Number of diseased leaves with lesion area ratio of 75 or more Control value (%) - (, - Damage degree of treated area) XI. .

Damage level in untreated area In this test, the compound 21 of the present invention showed a high control value at an active compound concentration of 200 ppm.

Example 7 Tomato late blight control effect test Tomato seeds (
Variety: Fukuju) was sown and grown for 3 weeks. An irrigation agent prepared according to Example 2 was diluted with water to a predetermined concentration, and 2 ml per pot was sprayed onto the seedlings. After air drying, tomato late blight fungus (Phytophthora fnfestan)
s) and placed in a constant temperature room at 25°C and 100% relative humidity for 24 hours. The plants were then placed in a greenhouse and the damage level was investigated 7 days after inoculation. The damage level investigation method and control value calculation method were the same as in Example 6.

In this test, compounds of the invention 17.19.21.24
．． 25, 26 and 27 showed high control values at an active compound concentration of 600 ppm.

Example 8 Wheat powder control effect test Wheat seeds (
Variety: Norin No. 61) was sown and grown in a greenhouse for 10 days. An irrigation agent prepared according to Example 2 was diluted with water to a predetermined concentration, and 2 ml per pot was sprayed onto the seedlings.

After air drying, wheat powdery mildew fungus (Erysjphae g.
raminis isp, tritici) and placed in a constant temperature room at 25° C. and 100% relative humidity for 24 hours. The plants were then placed in a greenhouse and the damage level was investigated 7 days after inoculation. The damage assessment method and control value calculation method were the same as in Example 6.

In this test, compounds 7 and 24 of the present invention were tested at 600p
It showed a high control value at an active compound concentration of pm.

Example 9 Wheat rust control effect test Wheat seeds (
Variety: Norin No. 61) was sown and grown in a greenhouse for 10 days. A hydrating powder prepared according to Example 2 was diluted with water to a predetermined concentration, and 2 ml per pot was sprayed onto the seedlings.

After air drying, wheat rust fungus (Puccinia reco
inoculated with conidia of M. ndita) at 20°C and relative humidity 1.
It was placed in a constant temperature room for 24 hours. Thereafter, the plants were placed in a greenhouse, and the number of lesions was investigated 7 days after inoculation, and the control value was calculated using the following formula.

Control value (%) - Average number of lesions in non-sprayed area In this test, compounds 18.24 and 27 of the present invention
A high control value was shown at an active compound concentration of 600 ppm.

Example 10 Efficacy test against corn leaf beetles 25 g of soil was spread on a filter paper with a diameter of 1 Q cm, the compound of the present invention was dissolved in a mixed solvent of acetone/methanol/water, and a surfactant (Triton X-100) was added. A chemical solution adjusted to a predetermined concentration was sprayed. After drying, the soil has an inner diameter of 7
．． It was placed in a 6 cm plastic cup, 2 ml of water was added, and 2 corn seeds were planted. Djabrotica undeeimpun
ctata howardi) about 50,270 eggs
ml of water and inoculated into the soil, the cup was covered with a lid and left in a thermostat with lighting at 30°C. 10 after leaving
The survival of the larvae was observed on the day, and the survival rate was determined.

In this test, compound 22 of the invention showed high insecticidal activity at an active compound concentration of 600 ppm.

Claims (2)

[Claims] (1) General formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (I) [In the formula, A is NR_1R_2 (R_1 represents a hydrogen atom, lower alkyl group, or lower alkoxy group, and R_2 is
A nitrogen atom or sulfur that may be substituted with a phenyl group, a lower alkyl group, a mercapto group that may be substituted with a lower alkyl group, a lower alkenyl group, a 4-morpholyl group, a phenyl group, a lower alkyl group, a lower alkoxy group, a halogen group, etc. 5-membered heterocycles having 2 to 3 heteroatoms selected from atoms and benzo-fused products thereof, or 6-membered nitrogen-containing rings which may be substituted with lower alkyl groups, lower alkylthio groups, halogen groups, etc. Represents a heterocycle and its benzo fused product. ) or represents a cyclic amino group such as a piperidyl group. ] A urea derivative represented by. (2) A pest control agent containing the urea derivative according to claim 1 as an active ingredient.