JPH03209351A - Phenoxyethylamines and germicide for agriculture and horticulture - Google Patents

Abstract

NEW MATERIAL:Phenoxyethylamine expressed by formula I [R is 7-10C alkyl; Y<1> and Y<2> are H or methyl (excepting simultaneous methyl of Y<1> and Y<2>; Y<3> is F, Cl, Br, methoxy t-butyl or phenyl] or a salt of phenoxyethylamine expressed by formula II (HX is mineral acid of equivalent value). EXAMPLE:N-[2-(2-Methyl 4-chlorophenoxy)ethyl]-N-n-octylamine. USE:Used as a germicide for agriculture or horticulture having bacteriostatic action or bactericidal action against pathogenic bacterium of plant disease. The compound expressed by formula I has a strong anti-bacterium action with large chemical stability. The compound expressed by formula II has a wide range of utilizable disease with a long applicable period and is also able to be used for prevention or remedy. PREPARATION:For instance, phenol expressed by formula III is reacted with dibromoethane expressed by formula IV in the presence of a base to obtain a compound expressed by formula V. Next, the resultant compound is reacted with an amine expressed by formula VI to afford the compound expressed by formula I.

Description

Detailed Description of the Invention [Field of Industrial Application] The present invention relates to a novel phenoxyethylamine and its salt, and a novel fungicide for agriculture and horticulture. [Prior Art, Problems to be Solved by the Invention] Conventionally, inorganic copper agents, organic copper agents, and antibiotic pIt agents such as streptomycin have been used as fungicides against pathogenic bacteria that cause diseases of agricultural crops. However, these conventional drugs include
Because it has problems such as not being sufficiently effective for practical use and causing drug damage, it also has a strong bacteriostatic or bactericidal effect (both are sometimes collectively referred to as antibacterial effect).
There is hope for the emergence of drugs that cause less drug damage. [Means and effects for solving the problem] As a result of intensive research to solve the problems of the above-mentioned conventional technology, the present inventors discovered a novel phenoxyethylamine and its salt, and moreover, The present invention was achieved by discovering that these compounds have bacteriostatic or bactericidal effects against pathogenic bacteria that cause plant diseases. That is, the first invention is a salt of phenoxyethylamine represented by the general formula (1) and the phenoxyethylamine represented by the general formula II. [However, in each of the general formula I and the general formula
Except when both t are methyl groups, y'' is a fluorine atom, chlorine atom, bromine atom, methoxy group, tert-
Indicates butyl toad or phenyl go. Furthermore, in the general formula H, HX represents an equivalent mineral acid. ] The phenoxyethylamine represented by the general formula I in the first invention can be produced, for example, as follows. That is, ■ ■ V' VI Phenol ■ and dibromoethane ■ are reacted in the presence of a base such as sodium hydroxide in a solvent such as water, alcohol, dimethyl sulfoxide or dimethyl formamide, and then converted to compound ■, Phenoxyethylamine (2) of the present invention is obtained by reacting this compound (2) with amine (2) in a solvent such as alcohol, dimethyl sulfoxide or dimethylformamide in the presence of a hydrogen bromide scavenger. The salt of phenoxyethylamine represented by the general formula II in the first invention can be obtained, for example, by reacting the phenoxyethylamine (2) described above with a mineral acid. The mineral acid used at this time is not particularly limited, but may be either gas or liquid, and typical examples include hydrochloric acid, bromic acid, iodic acid, sulfuric acid, nitric acid, and phosphoric acid. ．． HX in the general formula (■) corresponds to the acetic acid used during production. Further, in the production of these salts, although a reaction solvent is not always necessary, commonly used reaction solvents such as alcohols, ethers and esters, and water can also be used as reaction solvents. There is no particular restriction on the reaction temperature during salt production, but when gaseous mineral acid is used, the loss of mineral acid can be reduced by setting the reaction temperature to a low temperature such as 0°C. All of the phenoxyethylamine salts of the first invention are solid at room temperature to room temperature, and are recovered from the reaction solution by ordinary solid-liquid separation means such as filtration and centrifugation, and the recovered crystals are washed and alcoholic if desired. Alternatively, it can be purified by recrystallization from water. The physical properties of the phenoxyethylamine represented by the general formula (1) and the phenoxyethylamine salt represented by the general formula II in the present invention are shown in Table 1 and Table 2, respectively. Table 1 Physical properties of phenoxyethyl axi 1st row Compound numbers Yl, Y1. Y! and from the second row onward in the order of R ■ state, melting point. Boiling point etc.■ NMR measurement value '[1-NMR (CDCIs)
δpp■H CHs Cl −
(CHz) b-CHs■ Colorless oil Boiling point 139
～140℃70.5110g ■ 0.91(t-1ik
e, 3H). 1.35 (s, IOH). 1.39(s,
IH). 2.35 (s, 3B), 2.69
(t, J=6Hz, 2B). 2. 98 (t
, J=5Hz. 2H), 4.04 (t, J=5H
z. 2H). 6.5-6.7 (m, 2H), 7.20
(d, J=8Hz, 18)2H CHs
Cl 1 (CHz). -CHs■ Colorless oil Boiling point 140-145℃/0.4v++Hg■
0.89 (t-1ike, 38), 1.31 (m.12
H), 1.52 (brs.1), 1 2.35 (s, 3H), 2.69 (t, J
=6Hz, 2H), 3.00 (t, J-5H
z, 2B) 4.09 (t.J=5Hz.2H). 6.
6-6.8 (w.21). 7.20 (d, J=8Hz,
IH)H CB! CI-(
CFIt)l-C}13■ Colorless oil Boiling point 149
~155℃/0.3mwHg■ 0.88(t-1i
ke, 3B), 1.29 (w, 14B), 1.55 (s
, 10). 2.33 (s. 3B), 2.66
(t, J=6Hz. 2H). 2.97 o,
J=5Hz, 2H)4.02 ct, J=5Hz,
2H). 6.6-6.8 (*. 2B),
7. 17 (d. J=8Hz, 18)H
CHs Cl -(CHO)*-C
Hs■ Colorless oil Boiling point 156-160℃/0.3
m-8 ■ 0.87 (t-1ike.3H), 1.2
7 (m, 16H), 1.53 (s, IH), 2.33
(s, 3B), 2.66 (t, J=6Hz.
2B), 2. 96 (t, J=5+1z.
211), 4.02 (t, J=5Hz. 2H
), 6.6-6.8 (m, 28), 7.
16 (d. J=5Hz. IH) CL H
Cl - (Cllt) b-CH
s Colorless oil Boiling point 122-126°C/0.1
110g ■ 0.89 (tiike.3}1), 1.
31 (m.10H). 1.51 (s, IH)2. 18
(s, 3H), 2.67 (t, J=6Hz,
2H). 2.99 (t, J=5Hz. 21
{) , 4.02 (t, J=5Hz. 2H) , 6
．． 6-7.2(m, 3H)6 CHs H
Cl - (CHz) q-CI{
s■ Colorless oil, boiling point 139-145"C/O.
hm}Ig■ 0.88 (t-like, 3H),
1.291. w, 12H), 1.70(s,
IH), 3 4 5 2.18 (s. 38). 2. 69 (t,
J=6Hz+2H), 2.98 (t, J-5
Hz, 28). 4.02 (t, J-5Hz, 28)
,6.6-7.2(si.3H)CHsH
Cl-CHgCB(CJs)-C4
B,■ Colorless oily substance Buddha point 150-152℃/0.3
mmHg ■ 0.88 (t-13ke.6H), 1.2
9 (+++, 9H), 1.43 (s.IB). 2.15
(s, 3}1) , 2.55 (d, J-5H
z, 28). 2.93 (t, J-5Hz.
2H). 3.95 (t, J=5Hz, 21), 6.5
-7.2(s+,3B)CHs H
Cl-C(CHs) zcHzcccHx)
s Colorless oil Boiling point 150-155℃ 70.3
1 mug■ 1.00 (s.9H). 1.13(s
．． 6H). 1.43(s.2B), 1.43
(s. 1B), 2. 13(s, 3B). 2
．． 90(t, J-582.28), 3.94(
t, J=5Hz. 2B), 6.5-7.1 (m.
3H) CHi H Cl − (C
L) s-CHi■ Colorless oil Boiling point 160-162
'C/0.2 questions Hg ■ 0.88 (t, J=6Hz, 3
B), 1.27 (m, 148), 1.56 (s.IB)
,2. 17 (s, 3B). 2. 66 (t
, J=6Hz, 2H), 2.98(t, J=
5Hz. 28) ,4.00(t,J=5Hz,28
), 6.6-7.2 (m, 38) 10 GHz
H Cl − (CIllg)
? -CH3■ Colorless oil Boiling point 172-175℃/
0.2+*mHg■ 0.87 (tichimokuke, 38),
1.25 (m, 16H), 1.52 (s.111), 7 8 9 2. 16 (s, 3H), 2.65 (t,
J=6Hz, 2H), 2.98 (t, J=5
Hz, 2H). 4.00 (t. J=5Hz.
2H). 6.6-7.2 (s+, 3H)H
H t-Bu − (CHz
)． -CFIs■ Colorless oil Boiling point 176-18
0℃70.2■-og■0.88(t-1ike.3
H), 1.30 (m, 211). 1.75 (s, IH)
．． 2.67 (t, J-6Hz. 2H). 3.
00 (t, J=5Hz, 2H). 4.08 (
t, J=5Hz. 2H). 6.84 (d+m
, J=9Hz. 2H) ,7.33(ds, J=9
Hz, 28) 12 H H Br
-CClh)t-CH! ■ Colorless oil, boiling point 179
～183℃/0.1amHg■ 0.87(t-1ik
e. 3H). 1.29 (m.12B), 1.44 (s,
1}1), 2.64 (t.J=6Hz, 2H), 2.9
5 (t, J = 5Hz, 2H), 4.00 (t, J = 5H
z, 2H), 6.77 (dm, J=9Hz, 2H), 7
．． 33 (da, J=9Hz.2B) H H OCR3 −(CH
z)? -CH3 ■ Colorless columnar crystals Melting point 34-35℃ ■ 0.87 (t-1ike, 38), 1.30 (*,
12H). 1.48(s, 11{), 2. 74 (t
, J=6Hz. 2}1) , 2.95(t, J
=5Hz, 28), 3.71 (s. 3H)
, 3.99 (t, J=5Hz.2H). 6.77 (s
,4R)14Hl{ phenyl
-(CHa)t-(jlil1 13 ■ Colorless columnar crystals Melting point 43-45°C ■ 0.88 (
t-1ike. 3B). 1.30 (s, 12B). 1.
51 (s.IH), 2.68 (t, J=6Hz.2H)
, 3.02 (t, J=51'lz.2H). 4.10 (
t, J=5Hz. lMl). 6.97 (da, JJHz
．． 2B>, 7.2-7.6 (-, 711) 15 8 H F - (CL)
t-CL■ Colorless oil boiling point 160-163°C/0.
6sdg ■ 0.87 (t-1ike.31'l), 1
．． 29(a+.12B). 1.54 (s, 1B), 2.
65 (t.J=6Hz.2H). 2.96 (t, J=5
Hz. 2H), 4.01 (t, J=5Hz.2H)
, 6.8-7.1 (m, 4H) (hereinafter referred to as blank space) The second invention also provides a phenoxyethylamine represented by the general formula I and a salt of the phenoxyethylamine represented by the general formula II. This is an agricultural and horticultural fungicide characterized by containing an effective amount of at least one of the following. [However, in each of the general formula I and the general formula group), Y3 is a fluorine atom, a chlorine atom, a bromine atom,
Indicates a methoxy group, tert-butyl group or phenyl group. Furthermore, in the general formula (2), HX represents an equivalent amount of mineral acid. ] The phenoxyethylamine represented by the general formula ■ and the phenoxyethylamine salt represented by the general formula II (these phenoxyethylamines and their salts may be hereinafter collectively referred to as phenoxyethyl amines) are XanthOmOnaS genus 1, such as canker-causing bacteria, and Corynebacterium, such as tomato canker-causing bacteria.
It not only shows strong bacteriostatic and bactericidal effects against bacteria of the genus Rium, but also shows strong antibacterial action against pathogens of other plant diseases. All of these phenoxyethylamines are chemically stable due to their chemical structures and can withstand long-term storage.

Therefore, the agricultural and horticultural fungicides of the second invention, combined with the strong bacteriostatic and bactericidal effects of these phenoxyethylamines, make agricultural and horticultural fungicides that use this compound as an effective ingredient impractical. It's expensive.

In the agricultural and horticultural fungicide of the second invention, all of its active ingredients, such as phenoxyethyl alcohols, have a broad antibacterial spectrum. Therefore, the Jl horticultural fungicide of the second invention can be used, for example, for citrus canker disease, rice leaf blight, peach borer bacterial disease, cabbage black rot, lettuce spot bacterial disease, melon brown spot bacterial disease, and soybean leaf scorch disease. It is effective in controlling a wide range of plant diseases caused by various pathogens, including tomato canker and tomato canker. The effectiveness of the agricultural and horticultural fungicide of the second invention is as follows:
Compared to phenoxyethylamine, phenoxyethylamine salts are preferred because they are easier to recover and therefore easier to produce, and have stronger antibacterial activity.

The agricultural and horticultural fungicide of the second invention can be prepared by using the novel compound of the first invention, and by a method known per se.
Prepared into any dosage form that can be adopted as conventionally used agricultural and horticultural chemicals, especially agricultural and horticultural fungicides, such as liquids, emulsions, flowables (sols), powders, driftless (DL) powders, and granules. be able to.

As the carrier used in these preparations, those commonly used for agricultural and horticultural chemicals can be used, and there are no particular limitations.

For example, representative examples of solid carriers include mineral powders such as kaolin, hentonite, clay, talc and permiculite, vegetable powders such as wood flour, starch and microcrystalline cellulose, petroleum resins, polyvinyl chloride, ketone resins and dammargum. Representative examples of liquid carriers include water, alcohols such as methyl alcohol, ethyl alcohol, n-7' propyl alcohol, iso-propyl alcohol, butanol, ethylene glycol, and benzyl alcohol. ,toluene,
Aromatic hydrocarbons such as benzene, xylene, ethylbenzene and methylnaphthalene, halogenated hydrocarbons such as chloroform, carbon tetrachloride, dichloromethane, chloroethylene, monochlorobenzene, trichlorofluoromethane and dichlorofluoromethane, ethyl ether, Ethers such as ethylene oxide and dioxane, ketones such as acetone, methyl ethyl ketone, cyclohexanone and methyl isobutyl ketone, esters such as ethyl acetate, butyl acetate and ethylene glycol acetate, acid amides such as dimethylformamide and dimethylacetamide, dimethyl sulfoxide, etc. sulfoxides, alcohol ethers such as ethylene glycol monomethyl ether and ethylene glycol monoethyl ether, aliphatic or alicyclic hydrocarbons such as n-hexane and cyclohexane, industrial gasolines such as petroleum ether and solvent naphtha, and paraffins. , petroleum distillates such as kerosene and diesel oil.

Moreover, various surfactants can also be used.

Representative examples of surfactants include nonionic surfactants such as polyoxyethylene alkyl ethers and polyoxyethylene alkyl esters, anionic surfactants such as alkylbenzene sulfonates and alkyl sulfates, laurylamine and stearyl. Examples include cationic surfactants such as trimethylammonium chloride and amphoteric surfactants such as betaine carboxylic acids and sulfuric acid esters.

There is no particular restriction on the content of the compound of the first invention in the above-mentioned preparation, but in practice it is usually 0.001 to 95wt!
The amount (indicated as a compound represented by the general formula (2); the same applies hereinafter) is preferably about 0.01 to 90 wt1. For example, in practice, it is usually about 0.01 to 5 wtχ for powders, DL powders, and grains, and about 1 to 75-tχ for permanent agents, liquids, and emulsions.

The preparations prepared in this way can be applied as is, for example in powders, driftless formulations and granules.
Permanent preparations, solutions, emulsions and flowable preparations are diluted with water or an appropriate solvent before application.

Furthermore, the agricultural and horticultural fungicide of the second invention can be used in combination with other agricultural and horticultural fungicides, herbicides, insecticides, plant growth regulators, fertilizers, and the like.

The agricultural and horticultural fungicide of the second invention can be applied as is or after being diluted to the foliage of crops, or applied to the surface of water, water, the surface of soil, or the inside of soil.

The application amount of the 71 horticultural fungicide of the second invention varies depending on the type of target disease, degree of disease, type 1 of the target crop, application site, application method, application time, type of dosage form, etc., and cannot be specified in general. However, as an effective amount, as a compound represented by the general formula (■) of the first invention (in the case of the general formula H of the first invention, it is converted to the general formula (■)), per 10 ares, powder, drift The weight is 2 to 6 kg for anti-resist agents and granules (both with an active ingredient concentration of about 3wt!), and for permanent agents, liquids, emulsions, and flowable agents (all with an effective ingredient concentration of about 20wtX). ,0.
The compound of the first invention, which is used by diluting ~3 kg in 100 to 500 f water, has a strong antibacterial effect and also has high chemical stability due to its chemical structure. Also, general formula I
Compounds designated by I have particularly strong antibacterial effects. Therefore, the agricultural and horticultural fungicide of the second invention can be used against a wide range of common diseases, has a long application period, and can be used not only for the prevention but also for the treatment of plant diseases. [Example] The present invention will be explained in more detail with reference to Examples. The present invention is not limited to these examples. Example I Synthesis of N-[2-(2-methyl-4-chlorophenoxy)ethyl]-N-n-octylane (compound 6) or 2-(2-methyl-4-chlorophenoxy)ethylbro 2.50g (10.0mmol) of ethanol 3
Dissolve in 0+d and add 1.06 anhydrous sodium carbonate to this.
g (10.0 mmol) and n-octyluane a 3.8
7 g (30.0 mmof) was added and heated under reflux on an oil bath for 6 hours. After cooling, the reaction mixture was poured into 100+d of water and extracted with chloroform (20mxx3). After drying the organic layer over magnesium sulfate, the solvent was distilled off and the residue was subjected to silica gel column chromatography (H
2. Purify with ethanol:chloroform=3:97).
27 g (76% yield) of the title compound was obtained as a colorless oil. The physical properties of this compound were as follows. That is, "C NMR (CDCIs): 14.06 (q), 16.04 (q). 2
2.65 (t). 27.32 (t), 29
．． 27 (t). 29.52 (t). 30.
19 (t), 31.83 (t). 48.82
Ct>. 49.82 (t). 67.99 (t
), 112.20(d), 125.13(s)
．． 126.26(d), 128.52(s). 1
30.28(d). 155.50 (s) ppm infrared absorption spectrum (oil film method): vviax 2920', 2860".1595".
1455", 1240". IL85".1125'.1
035", 865', 800"CI+-' Mass spectrum: ex/e 297(M", 18!).29B(M"+
1.3%), 299 (M”+2.6χ), 19B (1
1%). 156 (15%). 142 (10
0! )． 56 (13%). 44 (55z)
．． Ultraviolet absorption spectrum (f!t01): λ+sax
203 (33.500). 229 (16.800)
．． 280 (2,700), 287 ”h (2,38
0) nm elemental analysis: Calculated value as C+JzsCINO C: 68.55 H: 9.47 N: 4.
70(X) Actual value C: 6B. 69 H:9.45 N:4,99
(Z) Example 2 N- r2- (4-methoxyphenoxy)ethyl]-
The combination of N-n-octylamine (compound 13) 2-(4
-Methoxyphenoxy)ethylbrothide 1.16g (
5.00 mmal) in 15M1 ethanol,
Add to this 106g of anhydrous sodium carbonate (10, Ommo
l) and n-octylamine 2.00g (15.5mm
ol) and heated under reflux on an oil bath for 8 hours. After cooling, the reaction mixture was poured into 50-m water and chlorowater lum C20
dX3). After drying the organic layer over magnesium sulfate, the solvent was distilled off, and the residue was subjected to silica gel column chromatography (developing agent: chloroform; ethyl acetate: nitrogen: ethanol-30).
:17:50:3)? Purified, 0.98g (yield 70%)
) was obtained as colorless columnar crystals.

The physical properties of this compound were as follows. That is, melting point 34-35°C "C-NMR (CDCI,); 14.06 (q). 22.65 (t). 27.38 (t
). 29.27(t). 29.55 (t), 30.19
(t). 31.83(t), 49.03(t). 49.
9Ht). 55.6Hq), 68.18(t), 114
．． 6H2C. d). 115.53 (2C, d). 153
．． 00(s). 153.88(s)pp Infrared absorption spectrum (oil film method): vvaax 2930".2860". 1510
",1460". 1230', 1135".1110"
+1035",825"+760".735"Cl
Mass spectrum: Vale 279 (M", 18%), 280 (M"
+1.4X), 180 (IOX), 156 (100χ
), 142 (70X), 56 (13χ), 44 (
62X). Ultraviolet absorption spectrum (EtOH): λs+ax 201 (18,400), 226 (16
, 100). 289 (4.590), 29B” (3,2
80) nm Elemental analysis: Calculated value C as C+JzJOt: 73.
07 8:10.46 N:5.01(!) Actual value C:73.36 }1:10.20 N:4.8
1(χ) Formulation example 1 (permanent agent) Ingredients Part by weight Compound 2
20 Lignosulfonic acid 3 Polyoxyethylene alkyl allyl ether 2 Diatom ± 75 The above components were mixed uniformly to obtain a permanent agent containing an effective amount of 20% by weight. Formulation example 2 (powder) Ingredients Parts by weight Compound 23 Calcium stearate 1 silicic acid anhydride powder 1 clay
48 Talc 47 A certain amount of the above was mixed uniformly to obtain a powder containing 3% by weight of active ingredient. Test Example 1 Antibacterial test against plant pathogenic bacteria The antibacterial activity of phenoxyethylamine and phenoxyethylamine salts against various plant pathogenic bacteria was investigated.

That is, cabbage black rot fungus Xanthomor+as
cas-pestris pv. campestr
is, Citrus canker pathogen X. ca*pestris p
v. citri, rice bacterial leaf blight X. camp-e
atris pv. oryzaes }Corynebacterius+ michig
anense pv. sichiganense,
Chinese cabbage soft rot fungus Erwinia carotovor
a pv. Using P. carotovora as a test bacterium, the growth inhibition effect of the bacterium on an agar plate was investigated.

A test compound was mixed into a potato decoction medium supplemented with Bebuton, and a 2-fold dilution series was prepared with a maximum concentration of 100 ppm.
Agar plates were prepared by pouring the mixture into a veterinary dish. The test bacteria were inoculated onto an agar plate, and after culturing at 28°C for 2 days,
The presence or absence of bacterial growth was investigated.

The results are shown in Table 3.

The compounds of the present invention exhibited strong antibacterial activity against cabbage black rot, citrus canker, rice leaf blight, and tomato canker. (Margin below) Table 3 Antibacterial test against plant pathogenic bacteria Minimum inhibitory concentration (.ppm) 12.5 12.5 6.3 6.3 12.5 6.3 50 50 25 25 6.3 6.3 25 12 .5 25 12.5 25 25 6.3 6.3 12.5 6.3 50 100 25 25 6.3 12.5 50 12.5 25 25 32 1.6 1.6 1.6 6.4 3 .2 12.5 25 50 12.5 1.6 3.2 12.5 12.5 50 12.5 25 12.5 3.2 3.2 12.5 6.3 25 50 6.3 6.3 6.3 12.5 50 50 50 25 25 100 25 50 12.5 50 >100 〉l00 100 〉100 100 12.5 50 100 25 50 Streb Hontomycin 12.5 6,3 12.5 6.3 6. 3 6.3 50 6.3 25 12.5 6.3 12.5 12.5 6.3 12.5 50 6.3 25 25 1.6 3.2 . 3.2 1.6 3.2 50 6.3 6.3 6.3 6.3 1.6 6.3 6.3 12.5 50 6.3 6.3 50 50 〉100 12.5 25 12 .5 50 100 25 Test Example 2 Citrus Canker Disease Control Test A leaf piece approximately 1 cm square was cut from a Natsumi orange leaf, and the leaf piece was immersed in a chemical solution prepared to a predetermined concentration for 20 minutes.The leaf piece was then removed from the chemical solution and the chemical solution was air-dried. After that, the leaf pieces were inoculated with a suspension of citrus canker bacteria (approximately 10"/1) using a needle. The inoculated leaf pieces were placed in a Petri dish lined with moist filter paper, and after incubation at 28°C for 10 days, the onset of the disease was investigated. The degree of morbidity was determined according to the following formula.In addition, the occurrence of drug damage was determined by visual observation.The results are shown in Table 4.In the above formula, nyu: attack index O n1: attack index 1 nx: Disease index 2 0 Go 2 Disease index 3 NEW Number of leaf pieces (no disease) Number of leaf pieces (slightly diseased) Number of leaf pieces (moderate disease) Number of leaf pieces (severe disease) Number of leaf pieces (margin below) 4th Table: Citrus canker disease control test 300 300 300 300 300 300 300 300 300 300 300 300 300 300 300 300 300 14.3 0.0 14.3 22.2 16.7 0.0 13.3 10.0 26.7 3.3 6.7 0.0 14.3 20.0 0.0 13.3 20.8 ± ± ± ± No tomycin treatment 66.7 Test Example 3 Rice bacterial leaf blight control test Growth in pots with a diameter of 6 cm An aqueous solution of the test compound prepared at a predetermined concentration was sprayed on rice (cultivar Koshihikari) at the 5-leaf stage. One day later, a suspension of rice bacterial wilt disease prepared at 10"/d was inoculated into leaves.

Three weeks after inoculation, the lesion length was measured and the control value was calculated using the following formula. The results are shown in Table 5. (Margin below) Table 5 Rice leaf blight control test 500 500 500 500 500 500 500 500 500 500 500 500 75.6 90.0 88.2 80.5 96.3 75.6 90.0 88.2 95 .1 90.0 96.3 75.6 *Commercial control drug test example 4 Soft rot control test A radish disk with a diameter of 2 cm and a thickness of 1 cm was prepared and immersed in a chemical solution prepared at a prescribed concentration for 1 hour. This Φ radish disk was taken out from the aqueous solution of the test compound, air-dried, a bacterial solution was poured into the center of the disk, and the disk was heated to 28°C for 24 hours.
After the period of time, the degree of disease onset was investigated, and the control value was calculated using the following formula. The results are shown in Table 6.

Table 6 Soft rot control test *Commercial control drug C Effect of invention]

Claims (2)

[Claims] (1) Phenoxyethylamine represented by general formula I and a salt of the phenoxyethylamine represented by general formula II. ▲There are mathematical formulas, chemical formulas, tables, etc.▼ I ▲There are mathematical formulas, chemical formulas, tables, etc.▼ II [However, in each of General Formula I and General Formula II, R is an alkyl group with 7 to 10 carbon atoms, Y^ 1 and Y^2 are the same or different from each other and are a hydrogen atom or a methyl group (except when both Y^1 and Y^2 are methyl groups), Y^2 is a fluorine atom, a chlorine atom, a bromine atom, Indicates a methoxy group, tert-butyl group or phenyl group. Moreover, in general formula II, HX represents an equivalent mineral acid. ] (2) An agricultural and horticultural fungicide characterized by containing as an active ingredient at least one of phenoxyethylamine represented by general formula I and a salt of the phenoxyethylamine represented by general formula II. ▲There are mathematical formulas, chemical formulas, tables, etc.▼ I ▲There are mathematical formulas, chemical formulas, tables, etc.▼ II [However, in each of General Formula I and General Formula II, R is an alkyl group with 7 to 10 carbon atoms, Y^ 1 and Y^2 are the same or different from each other and are a hydrogen atom or a methyl group (except when both Y^1 and Y^2 are methyl groups), Y^3 is a fluorine atom, a chlorine atom, a bromine atom, Indicates a methoxy group, tert-butyl group or phenyl group. Moreover, in general formula II, HX represents an equivalent mineral acid. ]