JPS58192858A - N-phenylcarbamate compound, its preparation and agricultural, and horticultural germicide containing the same as active constituent - Google Patents

Abstract

NEW MATERIAL:A compound of formula I (X and Y are halogen, lower alkyl or cyano, etc.; Z is O or S; R1 is lower alkyl, lower alkenyl, lower alkynyl, etc.; R2 is 1-8C alkyl, 3-8C alkenyl, lower cycloalkyl etc.; however, R2 is not propargyl when X and Y are Br at the same time, R1 is methyl and Z is 0; R2 is not ethyl when X and Y are methoxyl at the same time, R1 is methyl and Z is O; R2 is not ethyl when X and Y are ethoxyl at the same time, R1 is ethyl and Z is O). EXAMPLE:Isopropyl N-[(8-methoxy-4-ethoxy-5-chloro)phenyl]carbamate. USE:An agriclutural and horticultural germicide capable of exhibiting the germicidal effects selectively on drug-resistant germs. PROCESS:An aniline derivative of formula II is reacted with a chloroformic ester or chloroformic thioester of formula III to give the aimed compound of formula I .

Description

[Detailed description of the invention]

The present invention is based on the general formula [! [In the formula, X and Y are the same or different,] 10 gene atoms,
A lower alkyl group, a lower alkyl group, a lower alkenyl group, a lower cyanoalkenyl group, a lower alkynyl lower alkoxy group, a cyano group, or a lower alkyl substituted with at least one atom or substituent of a halogen atom, a hydroxyl group, or a cyano group. group, or represented by the following general formula (however, Rs is a lower alkyl group, a lower alkenyl group, a lower alkynyl group,
(lower) 10 represents an alkyl group. -, R1 are the same or different and represent a lower alkyl group. n represents an integer of 2, 8 or 4. R- represents a hydrogen atom or a lower alkyl group. ) is shown. 2 represents an acid atom or a sulfur atom. R1 is a lower alkyl group, a lower alkenyl group, a lower alkynyl group, or a lower alkyl substituted with at least one atom or substituent among a halotene atom, a lower alkoxy group, or a lower cycloalkyl group. Indicates the group. C is any one of 01 to C8 alkyl group, Cs-Cm alkenyl x, csNas alkynyl group, lower cycloalkyl group, lower haloalkenyl group, lower haloalkynyl group, or halogen atom, cyano group, lower An alkoxy group, a lower alkenyloxy group, a lower haloalkoxy group, a phenoxy group, a lower aralkyloxy group, a lower cycloalkyl group, and at least III groups! - child or substitution 1
A lower alkyl group substituted with. show. ] It is indicated by. An agricultural and horticultural cocoonicide characterized by an N-phenyl carbamate compound, a method for producing the same, and an agricultural and horticultural cocoonicide containing the same as an active ingredient. In the general formula [11, X and Y are preferably a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a methyl group, an ethyl group, n
-Propyl group, n-butyl group, vinyl group, l-propenyl group, 2-propenyl group, ethynyl group, methoxy group, ethoxy group, cyano 1k, 1,2-dibutyl group, hydroxymethyl group, cyanomethyl group , 2-cyanoethyl group, 2-cyanovinyl group, methoxymethyl group. Ethoxymethyl group, allyloxymethyl group, propargyloxymethyl group, 2-fluoroethoxymethyl group, methoxycarbonyl group, ethoxycarbonyl group, allyloxycarbonyl group, 2-fluoroethoxycarbonyl group, propargyloxycarbonyl group, dimethoxymethyl group, Jetoxymethyl group, ethylenedioxymethyl group,
formyl group, acetyl group, hydroxyiminomethyl group, methoxyiminomethyl group, carbamoyl group, N-methylcarbamoyl group, particularly preferably x, Y is a chlorine atom,
Bromine atom, methyl group, ethyl group, n-propyl group, methoxymethyl group, and when X is methoxy group, ethoxy group, or methoxymethyl group, Y is one chlorine atom, bromine atom, methyl group, ethyl group, n -propyl group, methoxy group, ethoxy group, cyano group, methoxymethyl group, methoxycarbonyl group, dimethoxymethyl group, a7tyl group, etc. Further, 2 preferably represents an oxygen atom. Preferred examples of Rs include a methyl group, ethyl group, allyl group, propargyl group, difluoromethyl group, and 2-chloroethyl group. C is preferably a methyl group, an ethyl group, an isopropyl group,
5ee-butyl group, allyl M, l-ethylpropyl group,
l-Methylbutyl group% 1-methylpentyl group, l-methylhebutyl group, 1-methyl-2-propenyl group, propargyl group, 2-butenyl group, 1-methyl-8-butenyl group% 1-pentyl-2-propenyl group, 1-methyl-2
-propynyl group, l-ethyl-2-propynyl group, 2-
Pronyl group, l-butyl-2-propynyl group, 1-pentyl-2-propynyl group, cyclobutyl group, 2-cyanoethyl group, 2-fluoroethyl group, 2-chloroethyl group, 2-propynyl group, 2°2.2 -) Lifluoroethyl group, 1-fluoromethyl-2-fluoroethyl group, l
-chloromethylethyl group, l-bromomethylpropyl group, l-methoxymethyl-2-chloroethyl group, 4-chloro-2-phenyl 14-chloro-2-butynyl group, 1-
Cyclopropylethyl group, 1-cyclopentylethyl group, 2-methoxyethyl group, 2-n-propoxyethyl group, 2-isopropoxyethyl group%2-allyl toxyethyl group, 2-(2-chloroethoxyethyl)ethyl group, 2 −
Benzyloxyethyl group, 1-methyl-2-methoxyethyl group, 1-methyl-gn-butoxyethyl group, 1-
Methyl-gn-butoxyethyl &, 1-methyl-2-
Examples include phenoxyethyl group. The present inventors previously described the general formula [A] [wherein Y is the same or different and represents a lower alkyl group, a lower alkoxy group, or a halogen atom. ``Bon'' indicates a methyl group or an ethyl group. However, Y does not have a chlorine atom or a bromine atom at the same time. ] The N-phenyl carbamate compound represented by is used in benzimidazole thiophanate fungicides and cyclic iridium as described below.

[Plant pathogenic images showing resistance to cocoonicides, and
and other filamentous fungi (hereinafter referred to as drug-resistant fungi).
It was found that it exhibited a selectively strong bactericidal effect. After that
As a result of the study, N- represented by the general formula [I]
Phenylcarbamate compounds also have drug resistance and resistance to
They found that it is effective and completed the present invention. N-phenylcarbamate system represented by the general formula [tl]
, the compound is benomyl[methyl 1-(butyl carbamoylate)
Le) Benzui t! Sol-2-ylcarbamate], F
Veritasol [2-(2-furyl)benzimidazole]
], thiabendazole C2-C4-thiazolyl)benz
imidazole], carpendazim [methyl benzimine]
dazole-2-ylbamate], thiophanate
Methyl [1,2-bis(8-methoxycarbonyl-2-
thiourido) benzene], thiophanate [1,2-
Bis(8-ethoxycarbonyl-2-thioureido) base
benzimidazole/thiophanate series such as
Cocoon agent or N-(8',5'-dichlorophenyl
)-1,2-dimethylcyclopropane-1゜2-dical
boximide, 8-(8', 6'-dichlorfe
Nyl)-1-isopropylcarbamoylimidasoridine
-2,4-dione, 8-(8'.5'-dichlorophenyl)-6-methyl-b-vinyl
Xazolidine-2,4-dione, ethyl (R8)-8-
(8',5'-dichlorophenyl)-6-methyl-2,
4-dioxoxazolidine-5-carboxylate
Against drug-resistant bacteria that are resistant to which cyclic imide fungicides
, is characterized by showing a selectively strong bactericidal effect. The benzimidazole/thiophanate fungicides mentioned above are
, excellent control against various pathogens parasitic on agricultural and horticultural crops.
It has been shown to be effective and has been widely used as an agricultural and horticultural fungicide since around 1970.
It was commonly used and greatly contributed to increasing crop production. and
However, if these fungicides are continuously sprayed on crops, they will
As drug-resistant bacteria become widespread, the control effectiveness of drugs decreases, and practical use becomes difficult.
Uncontrollable barking situations often occur.
came. Spraying fungicides does not provide the expected pest control effect.
If the outbreak of disease cannot be suppressed, farmers, etc.
The damage caused to drug users is enormous. more benz
Any imidazole or thiophanate fungicide
The grasshoppers that are resistant to these fungicides are also resistant to this group of pond fungicides.
It is known to be #J-resistant and exhibit so-called cross-resistance.
There is. Therefore, even if you spray Benomyl, for example, the
In fields where no effect is observed, other benzimidazoles and
Even if a thiophanate fungicide is sprayed, no control effect can be expected.
I can't do it. Ben is used in fields where drug-resistant bacteria are widespread.
Discontinued use of zimidazole/thionone fungicidal cocoonicide
However, even if you stop using it, the density of drug resistance will increase.
There are four well-known cases in which drug resistance does not decrease, and once drug resistance has developed,
If this occurs, the effects will be felt for a long time afterwards.
. In addition, drug-resistant bacteria may exhibit cross-resistance in such openings.
target by spraying other fungicides that do not
The purpose is to control the diseases caused by benzimidazole.
Which ofphanate fungicides exhibit excellent control effects?
They are extremely rare, making accurate control difficult. Cyclic imide fungicides are used to treat gray mold, gray mold, and gray mold of various oak crops.
1. It is highly effective in controlling diseases such as nuclear disease, and
Widely used as a horticultural fungicide, it is very effective in increasing crop production.
It has contributed greatly. In recent years, due to the soaring oil prices, greenhouse cultivation facilities, etc.
Forced to save on oil consumption for heating;
As a result, the gray mold fungus, which is active at low temperatures, occurs frequently and becomes a problem.
It was. The special effect of controlling gray mold in this type of bark
Cyclic imide fungicides, which are drugs, play an important role.
. It also controls gray mold to the extent that it can be substituted for this type of fungicide.
There are no known practical fungicides that are highly effective. However, in general, the same type of fungicide is used continuously.
This results in the emergence of locusts that are resistant to the drug, and the disease control effect of the drug becomes less effective.
It is said to decrease, and also in the case of cyclic imide fungicides.
It has become clear that this is no exception. In other words, if any of the above cyclic imide fungicides is
When applied continuously to crops to control mildew, cyclic imides
A gray mold fungus that is resistant to all fungicides has developed.
There are increasing numbers of cases in which the control effect has decreased. Considering the above circumstances, the present inventors have
If there is a fungicide that shows a selective bactericidal effect, drug resistance will occur.
This is because it is expected to have a high disease control effect in the field.
Efforts were made to develop a fungicide with such properties. As a result, the above-mentioned he-phenyl carbamate compound
Mulberry M#Ii selectively strong bactericidal effect on the surface
It turned out that something was true. That is, the compound of the present invention has the following properties that are clear from the test examples described below.
As such, pens imidasol thiophanate fungicide
Wild animals susceptible to or susceptible to cyclic yeast aspergicide
against diseases caused by wild bacteria (hereinafter referred to as drugs).
It does not show any control effect, but drug resistance 1!1: Disease caused by Maro
The compound of the present invention has an excellent control effect against harmful insects.
The ability of cocoons to develop against drug resistance is extremely selective.
Met. Resistance to the aforementioned benzimidazole/thiophanate fungicides
The herbicide Tearbarpan [4]
-Chloro-2-butynyl N-(8-chlorophenyl)ka
[1-methyl-2-probamate], chlorbufam [1-methyl-2-pro
Pinyl N-(8-chlorophenyl)carbamate],
Rolprofam [isopropyl N-(8-chlorophenylated)
carbamate], propham [isopropyl N-
phenylcarbamate] shows selective cocoonicidal power.
reported in (C, & Acad, 8c,
Daris, t, 289, 8'erie D
(pp. 611-698, 1979) However, the compound of the present invention is
As compared to other herbicides, benzimidazo
Much superior to thiophanate fungicide resistance
It has a high pesticidal effect and is resistant to cyclic imide-based weed killers.
It shows excellent pesticidal effect on agricultural and horticultural crops.
It has almost no toxic effects and has high practical value.
Ru. On the other hand, the herbicides mentioned above are clear from their properties as herbicides.
When sprayed on foliage, it can cause chemical damage to agricultural and horticultural crops.
It has a strong effect, and also contains benzimidazole and thiophane.
Bactericidal effects against cocoonicide and drug-resistant surfaces can also be put to practical use.
It's not that strong. The compound of the present invention is a benzimidazole thio compound as described above.
Resistant to fanate cocoon agents or ringworm insecticides
Used to control drug-resistant surfaces selectively against
can be done. t=Toe+! , powdery mildew ill (Pod
osphaera Jeuootricha), scabosis
Fungus (Ven*uria tnaqualis), black
Point disease fungus (Mycosphaerella pomi)
, brown spot-(Marasorina mali),
Monilia disease fungus (8o1sroi, inlamali)
, Power + (D ”l Tonko JM Cocoon (Phyllao)
tiniakakicola), anthracnose (Gloe
osporium kaki), peach gray layer fungus (8o
1erotinta cinarea), Sclerosis fungus
(Oladosporium earpophilum
), Phomopsis s
p, ), grape botrytis fungus (Botrytis
cinarea), brown spot fungus (0eroospo
raviticola), powdery mildew (Unoin
ula necator), Elsin
oe ampelina), imw cocoon fungus Glom
areella cinguJata), sugar beet
Cereospora becioolm - (Cereospora becioolm)
), bean nut brown spot-(0ercospora
arachidieola), Kuroshibuibiso (C5rc
osporapersonata), barley sac
Erysipbegramins 11
f+sp, hordei), Aiken spot disease fungus (
0ercosporella herpotrjcho
ides ), red snow rot fungus (Fusarjulnni)
vale), wheat powdery mildew (Erysiph
e graminis f, sp6, tritiai
), cucumber powdery mildew (8phaeroth
@ca fuliginaa), 4th blight fungus (My
oosphaerella melobi Hatake), Sclerotinia
Fungus (8clerotinia sclsrotioru)
m) %Botrytis cine
rea ), Cladospori ill ( Cladospori
umcucumerjnum), tomato fungus
(Cladosporium fulvnm), gray
Mildew $1 (Botrytis cinerea)
, Coryhespora melo
ngehae), strawberry powdery mildew fungus (8phaa
rothsaa humuli ), @ Huangbyou ii
(Fusarium oxysporum f, sp,
fragarjae), onion gray rot [1
(Botrytis alli), lettuce cocoon
(5clerotinia 5olarotiorua
+), Cerulino spot fungus (0araoipora
apii), common bean endophytic fungus (Phae
oisarjopsis griseolm), hot
Botrytis oin@r#
), tobacco udon and disease bacteria (Brysiphe oic
horacearum ), rose scab fungus ( Dipl
ocarpon rosae), a mandarin orange fungus
(Elsloos fawcetti), gastric mold disease
-(Penicjllum italicum),
Penioillium mold [1]
It can be used to control drug-resistant bacteria such as
Ru. In actual fields, drug-resistant bacteria and susceptible bacteria coexist.
In case of C color, benzimidazole thione mononate
One or more types of methyl fungicides or cyclic imide fungicides
The above and the N-phenyl car represented by the present compound [I]
Can be used in combination with one or more types of bamate-based compounds.
It is possible to control both drug-resistant and sensitive bacteria at the same time.
It is possible. N-phenyl carbamate system represented by general formula [11]
As a result of further investigation of the bactericidal activity of the compound, drug resistance was detected.
be effective in controlling certain diseases with or without
There was found. The compound of the present invention can be used, for example, for rice blast disease.
Fungus (Pyrioulariaoryxae), cucumber
Pseudoperonosporac
ubensis ) % Grape Downy Mildew @ (Plas
mopars viticolm), Jackpot blight
Bacteria (Phytophthora 1nfsstans)
) Can be used to control throat. On the other hand, the compound of the present invention is highly safe for humans, livestock, and fish.
and has no practical use in agriculture and useful crops.
It has also become clear that it can be used without causing any harm.
. The compound of the present invention represented by the general formula rT1 is ethyl N-[
(8,4,5-trimethoxy)phenyl]carbamate
, ethyl N-r(8,4,5-triethoxy)phenyl
] Carbamate, Plulopacgil N-r (8,5-dibromo-4-methoxy)
Except for 8 points of phenyl]carbamate, all of them are new compounds.
Ru. These eight compounds are Arch and Pha, respectively.
rm, 272, 221-286 (1984)F
4rench Patent M 8200 D"-
Although it is described in 082-041,98g, it has no bactericidal activity.
and its usefulness as a fungicide.
is not listed. The compound of the present invention [11] can be produced by the following method. (a) General formula [I[] [In the formula, X, Y and R1 have the same meanings as above. ] The aniline hook conductor shown by the general formula [11]
and 2 have the same meanings as above. ] Chloroformic acid ester or chloroformic acid ester represented by
A production method that involves reacting with tel. This reaction involves benzene, toluene, xylene, diethyl
Ether, tetrahydrofuran, dioxane, chlorophore
aluminum, carbon tetrachloride, ethyl acetate, pyridine, dimethyl fluoride
in organic solvents such as lumamide or mixtures thereof.
Me, pyridine, triethylamine, diethylaniline
, dehydrochlorination agents such as sodium hydroxide, potassium hydroxide, etc.
The reaction can be carried out in high yield by using
For the reaction, cool or heat (0 to 150℃) as necessary.
), the process can be completed from instantaneous to 10 hours, and the yield can be improved.
You can get what you want. Aniline salt represented by the general formula [11] in the manufacturing method (&)
The conductor has the general formula [fl [wherein, X, Y and R1 have the same meanings as described above]. ] Obtained by the reduction reaction of the nitrobenzene derivative shown by
. This nitrobenzene derivative is, for example, a nitrophenol derivative represented by the general formula [VIc, in which X and Y are as described above] and a nitrophenol derivative represented by the general formula % [wherein M represents a leaving group]. R1 is as described above. ] React with the alcohol derivative or nolide shown by
It can be obtained by Here, the leaving group is denoted by
generally refers to tosyloxy, mesyloxy, or
10 Gen atoms are shown. The nitrophenol derivative represented by the general formula [ma] is
For example, Reference J, 0. G 196ffi, 27.218-226
It can be easily obtained by the method described in . Nitrophenol derivatives represented by the general formula [ma] and general
An alcohol derivative or halide represented by the formula [W] and
The condensation reaction of benzene, toluene, xylene, diethyl
ether, tetrahydrofuran, dioxane, chloro
Form, carbon tetrachloride, ethyl acetate, ethanol, isopropylene
Organic solvents such as Ropatool and dimethyl formaldehyde
Alternatively, it is carried out in water etc. or a mixture thereof. Pi
Lysine, triethylamine, caustic soda, caustic potash, charcoal
By using a dehydrohalogenating agent such as acid soda,
The reaction can be carried out in high yield if necessary.
0.5 to 10 hours by heating or cooling
The desired product can be obtained in good yield. The nitrobenzene derivative represented by the general formula [m] is
As a reduction reaction leading to the aniline rust conductor represented by [Ir]
These include platinum oxide, Raney nickel, platinum black, and f-radiu.
Catalytic reduction using catalysts such as aluminum carbon, tin, iron, and zinc
reduction using metals such as hydrochloric acid, sulfuric acid, etc.
um, lithium, aluminum, magnesium, zinc etc.
Reduction in alcoholic solution by which metal, sodium
, with zinc and alkali hydroxide or alcoholic alkali
reduction using stannous chloride, ferrous sulfate, and ferrous hydroxide.
Iron, sodium sulfide; sodium polysulfide, ammonium sulfide
Reduction using inorganic compounds such as aluminum and hydrogen sulfide, hydrazide
Reduction by hydrazine compounds such as phenylhydrazine and
You can give money, etc. Taking catalytic reduction using palladium-carbon as an example,
The reaction is benzene, toluene, ethanol, methanol,
At normal pressure in isopropanol, solvent or mixed solvent.
Or by hydrogenation under pressure. The reaction was completed in 80 minutes to 10 hours, and the target product was obtained in good yield.
Obtainable. (b) General formula [v1]! [In the formula, x, Y and R1 have the same meanings as above. ] A phenyl isocyanate derivative represented by the general formula) [wherein R2 and 2 have the same meanings as above. ] React with alcohols or thioalcohols shown in
manufacturing method. This reaction is solvent-free or is free from benzene, toluene, and xylene.
, diethyl ether, tetrahydrofuran, dioxane
, N, N-dimethylformamide, chloroform, tetracyclic
In a 811-containing solvent such as carbonized carbon A, without catalyst or with triethylene
Ruamine, N,N-diethylaniline, 1,4-diaza
Bicyclo-(2,2,2)octane as a catalyst
I can do that. The reaction is cooled or heated (0 to 50°C) as necessary.
By doing this, the process can be completed from instantaneous to 10 hours, achieving the desired goal with high yield.
can get things. Phenyl isocyanate derivative represented by general formula [■]
is an anion derivative of the general formula [1[t'b denoted by 'l]
It is best to react with phosgene in order to obtain
Ru. This reaction involves benzene, toluene, xylene, and ethyl acetate.
Organic solvents such as esters and the like are carried out in their mixtures. The reaction is
If necessary, heat from 50℃ to reflux temperature.
The process can be completed in 10 hours rather than instantaneously, and the target product can be obtained with high yield.
You can get crabs. (C) General formula [■]! 1 [In the formula, X1 group, loss and 2 have the same meaning as [1]
Ru. ] Benzaldehyde and hydroxylamine represented by
or the general formula [K] Y [wherein, X , Rr , R1 and 2 are the same as above]
have meaning. Yl is a hydroxyiminomethyl group or
Indicates a lower alkokereiminomethyl group. ] Production of N-phenyl carbamate compound represented by
Construction method. The reaction consists of benzaldehyde represented by the general formula [■]
Dissolved in an inert solvent, where an equivalent or excess amount of hydrochloride is added.
Inert solvent for xylamine or lower alkoxyamine
Add the solution. The reaction is completed in 80 minutes to 12 hours.
do. Here, the inert solvent is preferably methanol or
is ethanol. Next is the general ceremony [! ] Examples of the compounds of the present invention are
The compounds of the present invention are limited to the following:
It is not something that will be done. The compound numbers shown here are based on the formulation examples and tests below.
Commonly used in examples. Next, the present invention will be explained in more detail with reference to examples. Example 1 Isopropyl N-C (8-methoxy-4-ethoxy-6
Synthesis of -chloro)phenyl]carbamate (method (a)
(8-methoxy-4-ethoxy-5-chloro)aniline
2.0! and N,N-diethylaniline 1.61
III solution to toluene 2o-L, isopropyl chloro under water cooling
Formate 1.2N was added dropwise over 6 minutes. After leaving at room temperature 'F for 12 hours, pour into ice water and add toluene.
Extracted. The solvent was washed with water and dried with magnesium sulfate.
. The solvent was distilled off under reduced pressure, and the resulting solid material was dissolved in toluene.
Isopropyl N [(8-/)4
4-x), xy-5-chloro)phenyl]carbame
1.9 g of white crystals were obtained. (Yield 66.5%) Melting point 121-122°C Elemental analysis values N(X') C(%) H(%)
(z (%) calculation 4i1f 4.86 54.11
6.29 12.29 (as C+aH+aNOaCz
) Actual value 4.89 54.51 6.28 12.2
1 Example 2 Isopropyl N-CC8,4-jethoxy)-5-methy
fc (Method tb)
(8,4-jethoxy-5-methyl)anilino2. Of
was dissolved in 2o- toluene and added to a solution containing 1°F of phosgene.
It was added dropwise to the toluene solution at 10-20°C. It was heated gradually and refluxed for 80 minutes. Return to room temperature, condensate
was distilled off under reduced pressure to give 8,4-jethoxy-5-methylphenate.
2.21 of phenoisocyanate was obtained. without refining
, this is an isopropanol containing triethylamine IF
20- Added to the inside. 13 at room temperature! After leaving it for a while, add ice water, crack, and toluene.
Extracted with Wash the fII medium with water, and add 40% magnium sulfate.
Dry. The solvent was distilled off under reduced pressure, and the resulting solid material was dissolved in toluene.
Purified by recrystallization with
-jethoxy-5-methyl)phenyl]carbamate 2
．． I got 51. (Yield 88 from 8,4 Shedkin-6-methylanilino
%). Melting point 86-87.5℃ Elemental analysis value N(X) C(X)! ((%) calculation
Value 4.98 64.0B 8.24 (CxiH2
sNO4) Actual value 4.95 6B, 87 8.52 Example 8 Isopropyl N[(8,4-jethoxy-5-methoxy
Synthesis of iminomethyl)phenyl]carbamate (method (
Due to (+). ) isopropyl N-[(8,4-jeto
xy-5-formyl)phenyl]carbamate 0,61
It was dissolved in 20% of ethanol. Sodium hydroxide here
Um 0.821 and methoxyamine salt Ill salt 0.6 @#
A solution of 1O- in water was added. 12 hours at room temperature
After stirring, the liquid was distilled off under reduced pressure. Residue in acetic acid
Dissolved in ethyl, washed with water, and dissolved in magnesium sulfate.
Dry. After filtration, the filtrate is concentrated and the obtained solid is
Wash with sunscreen and remove isopropyl N-C (8,4-jetoxy).
-5-methoxyiminomethyl)phenyl]carbame)
0.611 was obtained. (Yield 98X) Melting point 110-111.5℃ Elemental analysis C (jt) H (%) N (%) total
Calculated value 59,24 7,46 8.64 (C+5
As H24N*Oi) Actual value 59,01 7.56 8.84 Invention
When actually applying the compound or the compound of the present invention
can be used in pure form without the addition of other ingredients, and
To make it easier to use as a fungicide, it can be mixed with a carrier and applied.
can be commonly used in filtration form e.g. powder, hydrated
agent, oil agent, emulsion, tablet, granule, fine granule, airmail,
It can also be used in threads such as Roable. The active compounds (referring to component II) are generally present in said formulations.
) to 1.0-95. OX, preferably 20~
Contains 80.0%, usually 2-100g per lOare
The application amount is appropriate. Furthermore, the concentration used is 0.00
The range of 5% to 0.5% is desirable, but the amount used,
The concentration depends on the dosage form, application time, method, location, target disease, and target crop.
Because it varies depending on the item, etc. - without regard to the range specified in U.
There is no problem with increasing or decreasing it. Additionally, other pesticides, reed repellents, plant growth regulators and insecticides
Can be used in combination with other agents, such as 8-norma
Rubworl S-Paratertiary Butyl Benzyldi
Thiocarbonoimidate% 0.0-dimethyl 0-(2゜
6-dichloro-4-methylphenyl) phosphorothioate
, N-trichloromethylthio-4-fuclohexene-
1,2-dicarboxyjt', cis-N-(111+
2.2-te)lachloroethylthio)-4-cyclohexe
-1,2-dicarboximide, polyquinone, ester
Left main, dinogethylene bisdithiocarbamate
Thick dimethyl thiocarbamate, manogannisuce
tyrene bisdithiokar imate, bis(N,,N-di
Methyl (ocarbamoyl) disulfide, tetranoyl
loinophthalonitrile, 8-hydroxyquinoline, dode
Silguanidinoacetate, 5.6-Sihydro2-methane
chill-1,4-oyasachiino-3-carboxanilide,
H'-dinololofluoromethylthio N, N-
Methyl-N'-phenylsulfamide, 1-(4-chloro)
lophenoxy)-8,8-,,)methyl-1-(1,2
, 4-triazol-1-yl)-2-butanone, methy
N-(2,6-dimethylphenyl)-N-methoquinoa
Cetyl-2-methylpurinonate, aluminum-ramethyl
Fungicides such as phosphites, 2.4-,) Chlorphenox
ciI[,2-methyl-4-chloroflephenoxy fMII
II, 2-methyl-4-chlorphenoquine vinegar # (esthetics
Phenoxy yarn leather removers such as 2, 4
-dichlorophenyl 4'-ditrophenyl ether, 2
．． 4.6-Dolichlorophenyl 4'-nitrophenyl
ter, di-chloro-4-trifluoromethylphenyl
8'-ethoxy-4'-=)lophenyl ether, 2.
4-dichlorophenyl 4'-nitro-8'-methoxyf
phenyl ether, 2゜4-dichlorophenyl -methoxy
diphenyl such as cyclocarbonyl-4'-nitrophenyl ether
phenyl ether type remover, 2-talol-4,6-pisue
tylamino-1,8.5-) riazine, 2-chloro-4
-ethylamino-6-itubrobylamino 1,8.5
-triazine, 2-methylthio-4,6-pisethyl-a
Minnow 1.8.5-) riazine, 2-methylthio-4,
6-pisisopropylamino-1.8゜5-triazine
Triazine herbicides such as 8-(8,4-dichlorophene)
8-(8,4-dimethyl)-1,1-methylurea, 8-(8,4-dimethylurea
lorophenyl)-1-methoxy-1-methylurea, 1
-(α,α-dimethylbenzyl)-8-p-tolylure
A, 1-(2-benzothiazolyl)-1,8-dimethyl
Urea herbicides such as urea, isopropyl N-(8-chloro)
(ruphenyl)carbamate, methyl N-(8,4-dimethyl)
Carnomamate-based WI such as lorphenyl) carbamate
Herbal medicine, 8-(4-chlorobenzyl)N,N-diethyl
Ruthiol carbamate, 8-ethyl N, N-hexame
thiol carbamates such as tyrefthiol carbamate)
i herbicidal fi, 8.4-dichloropropionanilide. 2-chloro-N-methoxymethyl-2',6'-diethyl
Ruacetanilide, 2-chloro-2r. 6'-diethyl-N-(butoxymethyl)-acetani
Lido, 2-chloro-2',6'-diethyl-N-(n-
propoxyethyl) athoanilide, N-chloroacetyl
Ru-N-(2,6-diethylphenyl)glycineethyl
Acid anilide herbicides such as esters, b-bromo-8-se
Candary-butyl-6-methyluracil, to 8-cyclo
Uracil series such as xyl-5,6-)limethylene uracil
Herbicide, 1,1'-dimethyl-4,4'-bipyridinium
Pyridinium salt herbicides such as muchloride, N-(phosphatide)
honomethyl)glycine, N,N-bis(phosphonomethyl)
) glycine, 0-ethyl 0-(2-nitro-6-methyl
phenyl)N-old-candalybutylphosphoroamidothio
ate, 8-(2-methyl-1-piperidylcarbonyl
methyl)0.0-di-n-probyldithiophosphate
, 8-(2-methyl-1-piperidylcarbonylmethyl
)0.0-diphenyl or di-n-propyldithiophor
Phosphorus herbicides such as sphate, α, α, α-trifluoro
rho2,6-sinitro N,N-dipropyl-P-tolu
Toluidine series such as Idine 1 [[M, 5-tertiary
Chil-8-(2,4-dichloro-6-itupropoxif)
enyl)-1,8゜4-oxacyapurin-2-one,
8-isopropyl-(IH)-2,1,8-benzothia
Diazin-(8H)-one-2,2-dioxide, α-
(β-naphthoxy)propionoanilide, 4-(2,
4-)Chlorobenzoyl)-1,8-dimethylpyrazo
l-5-yl p-toluenesulfonate, II-(meth)
quincarbonylamino)phenyl 8-methylphenylka
-bamate, 4-amino-8-methyl-6-phenyl-
1゜2.4-triazine, 0.0-dimethyl 0-(4-
Nitro-8-methylphenyl) phosphorothioate, 0
-(4-cyanophenyl)0゜0-dimethylphosphorothi
Oate, Q-(4-cyanophenyl)0-ethylphene
Nylphosphonothioate, 0,0-dimethyl 8-(N-
Methylcarbamoylmethyl)phosphorodithioate, 2
-methoxy-4H-1,8,2-benzodioxaphospho
Phosphorus-2-sulfide, 0.0-dimethyl 8-C1-e
Toxicarbonyl-1-phenylmethyl)phosphoroditi
Organophosphorus insecticides such as oeate, a-cyano-8-phene
Noxybenzyl 2-(4-chlorophenyl)isovalere
8-phenoxybenzyl 2,2-dimethyl-8-
(2,2-dichlorovinyl)cyclopropanecarboxy
rate, α-cyano-8-phenoxybenzyl 2.2-
Dimethyl-8-(2゜2-dibromovinyl)cyclopro
Mixed with pyrethroid insecticides such as pancarboxylate.
Can be used in combination, and both have the same pest control effect as each single agent.
It is expected that there will be no reduction in
It is something that will be done. Next, test examples and formulation examples will be given.
The usefulness as an ornamental pesticide will be further clarified. Commercially available fungicides used in the following Test Examples 1 to 9 and
Control compounds are shown in Table 2. & 2 * (b)
'0 Note (1) s (c) 〃 (d) # (・) Note (1)・The properties of the compound synthesized for comparison are) Mug
r1culture Biological Chem
istry 11g volume 5 pages 1707jj - 1719
(1971) Note (8) Commercially available herbicide Sho (4) Commercially available cocoon agent test example 1 Cucumber powdery mildew control effect of 90TntW
In a plastic pot, add some sandy loam and add a cucumber (
Seeds: Sagami half day) were sown. This was grown for 8 days at room temperature.
, cucumber seedlings with expanded cotyledons were obtained. This child (it child)
Droplets of the test compound in emulsion or permanent form are diluted with water.
It was sprayed on foliage until a sufficient amount adhered to the leaf surface. After air-drying the chemical solution,
Video shows drug-resistant or susceptible cucumber powdery mildew @i
(8phnerotbeca1°uligiaea
) was inoculated by spraying with a conidial suspension. put this in the greenhouse
After cultivation for 10 days and disease onset, the disease state was observed.
. % storage was calculated by the method of Fki. That is, θ depending on the appearance of lesions on the investigated leaves. It is classified into the index of 0.5.1.2.4, and the onset of disease is determined by the following formula.
The degree was calculated. (Infection index) (Infection status) 0 Leaf f
No tSS or lesions were observed on f1lIF. 05 ・l! On my face! Bacterial flora on less than 5 sides of the side
Or notice lesions. 1 Less than 20% of the leaf area on the leaf surface - clusters or lesions
Recognize. 2 -Less than 50% of leaf area
Recognize. 4...1J4Iiii upper number 1# 50% or more of area
plexuses or lesions are observed. ), the control value is calculated from the following formula: t:. As a result, as shown in Table 8, the compound of the present invention showed no drug resistance.
When inoculated, it shows an excellent control effect and can be used against drug-sensitive surfaces.
It does not show any control effect when planted.) On the other hand, commercially available
of benomyl, thiophanate methyl, carbenodam
Both have no control effect when inoculated with drug-resistant species.
Excellent control effect when inoculated with drug-susceptible species.
Indicated. Chemical structure tested for comparison @similar U compound
Commercially available sterilizers with similar chemical structures are inoculated on either side.
Even when tested, it showed almost no control effect. , /''/' Chapter 8 Table 1 Hypoallergenic compounds Self-@component Drug resistance- Drug sensitivity-
1# Hiki 4 inoculation fL-'a - No. in case of inoculation
: (pPm)1 control value (X) control value (X)”
200 100 (J7
2υlJ, 100 01
number la 200 97
01 &' 2 (101000 19110100υ 20 200 100
022 2υo(loo. 24 200 100
028 2 (10' 97
tJ291 200; too
. al 1 200: 94
υ32 200 97
03B 200' 100
086 200
97 0:, 50 200
97 051 20
0 100 0i52
200 97. 0.54 2
00 100 0□ '55 200 100 0□ 157 200 too
. 58 2001 100'
0. 59 200' 10
0 j O'62 200
100' 01 Compound @ Self-component/aM resistance-, drug sensitivity #
#i when tangent;
<pp...)1 control value)')'control - (%) 68
200 100 07
0 zoo' 100 ' 0
71 200, 100
. 73 zoo 100
074 200'100'
. 77 200 10o
c179 200 100
0?50 200'lOQ
086 200 100
088 200' g4
090, 200 10g
091 200 100
[192200970 99200'lOo' 0.102
200 100' 0.
108 20Ll 100
0'105 2t) 0 100
0109 200 100
01110 200
100 01111
200 100 0:
112 200 100
0□ '116 200 100
0117 200 100
0jl18 200 100
0 river 19 '200 100 0
・:122:200i100' 124: 200 j 100 1
0t compound Active ingredient: Drug sensitive area
The number (ppH1), the pest control value) □ the pest control value (
%) ■ +27 200 ・ ioo
0129 200 100
0130 2t10 1QQ
Ul;Ill 10
100 0132 2
00 100 0H (32
0010010 13↓ 200 100
01a3 200 100
・0188 200 1
00 0140 200
100 0141 200
100 1 0142 10
100 0143
10 100 1 0146
200 1ot) IQ147,
200, 100, 01
52 200' 100
0 Test Example 2 Sugar beet brown spot JPiVi mackerel effect 9
Fill a 0-41 volume plastic pot with sandy loam and place it in a pot.
The seeds were sown. After 20 days of cultivation in a greenhouse, an emulsion or
A droplet of a water-diluted solution of the test compound in the form of a wettable powder is distributed on the leaf surface.
Sprayed on leaves and foliage until care was taken. Chemical resistance in young butterflies after air-drying the chemical solution
or susceptible sugar beet brown spot - (Cercospor
a baticolm) conidia Ken II! Spray a
Mist inoculation. Cover this with a vinyl power bar and use it in humid conditions.
After cultivating for 10 days in a greenhouse, the disease state was observed.
Ta. The disease onset investigation method and control value calculation were carried out in the same manner as Test Example 1.
became. As a result, as shown in Table 4, the present invention was similar to the results of Test Example 1.
The compound has an excellent control effect when inoculated with drug-resistant
On the contrary, the commercial fungicides benomyl and thiophane
tomethyl and carpendazim inoculate drug-susceptible
Excellent control effect was shown in case of t. Provided for comparison
Compounds with similar chemical structures and (1, compounds with similar structures)
Commercially available emasculators are almost always E, no matter which terminal is connected.
It did not show any B-removal effect. Table 4 Test Example 8 Pear scab control effect: 90% peat moss and sandy loam in a plastic pot.
Pack the mixed soil and collect seeds from pear fruits (variety: Chojube)
The seeds were sown. This is grown in a greenhouse for 20 days, and the resulting seedlings are treated with emulsion or
A droplet of a water diluted solution of the test compound in the form of a wettable powder is applied to the leaf surface.
Sprayed on leaves until attached. Drug-resistant or susceptible pear scab fungus on young seedlings after air-drying the chemical solution
(Venturia naihicola)
A spore suspension was spray inoculated. This was done under humid conditions at 20°C.
for 8 days, followed by 20 days under fluorescent light at 20°C.
cultivated and infected. The disease detection method and control value calculation were the same as in Test Example 1.
Ta. As a result, as shown in Table 1915, the compound of the present invention showed drug resistance.
It shows an excellent control effect when inoculated on the surface, and on the other hand, commercially available sterilization
The agents benomyl and thiophanate methyl are drug-type
showed excellent control effects when inoculated with /'' 7/ / Table 6 Compounds (Active ingredients: 1 drug to increase drug resistance - 1 concentration to increase susceptibility)
Number i (if inoculated twice)
ppm)l control value (X)i control value (%)・89
200 1 ss 0104
200 100
0106 200' 100
0106 200 100
0107 200
91 0108 1 200
100 0110
200' 100
0, compound 11 component 1 drug Ml resistance - i drug sensitivity -
When inoculated once: Number when inoculated
(ppoll), prevention #d (%), control value (%) 17
4 200 1 100 0181
200, 100 0218
200 " 100 0 Benomyl
200 0 100 Exam Ga 4 Beenuts
Brown spot control effect Fill a 100-volume plastic pot with sandy loam, and
Natsutsu (variety: Nichiba semi-erect) was sown. 14 in the greenhouse
An emulsion or wettable powder is applied to the seedlings obtained after cultivating for several days.
Add a water diluted solution of the test compound to 10 liters per bottle and sprinkle with stem and leaf powder
I clothed it. After the chemical solution is air-dried, seedlings are exposed to chemical-resistant or sensitive bacteria.
Cercospora arachi
dicola) was applied to the spore suspension. Cover this with a vinyl cover to create a multi-condition, and put it in a greenhouse.
After cultivating for 10 days, diseased dragons were observed. How to investigate the onset of the disease
The method and calculation of control value were performed in the same manner as in Test Example 1. As a result, as shown in Table 6, the compound of the present invention showed no drug resistance.
When inoculated, it shows an excellent control effect, and on the contrary, commercially available fungicides
Benomyl and thiophanate methyl are drug-receptive to -
showed excellent control effects when inoculated with Table 6 Compound @1 active ingredient drug #drug sensitivity □1
i'If vaccinated Number if vaccinated' (p
pm) Pest control value quotient of ') Pest control value (%) 6 200
100 07 200,
100 013 2o0
1QQ 01(J
200, 100 012
'200', g7
. +5 10 100 01
9 21J0 100
0202001H. 22 200', 1go
. 24 20 (l g 8029
200 100 032
200' 100 08
6 10 100 088
200 94 0 compound
Item Effective acid content, drug Il$1 resistance- drug-susceptible surface □ #1 degree: when inoculated, rose when inoculated No.:
(ppl j control value ν control value (%) 101
200' 100 0102
200 100 0105
10' 100 0) 109 1 200 100 01
10 200 100 011
7 200 100 0184
200 100 011
2 (JO1000 141'200 100 1 0142
200' 100 014
6 200' 100 01
65 200 100 018
3 200 100 0z12
, 200' 100 0 trials
Experimental example 5 Cucumber gray mold control effect! 81Oydg.
Fill a plastic bot with myojido and add a cucumber (item a).
1: Sagami half day) 4 times. Cultivate this for 8 days at humidity 4.
And got a cucumber that Senyaku expanded. I love this video
or water dilution of the test compound in wettable powder form. Since 1O- per point, MU! I visited several cities. Sangxin wind drying, movement
Kyutsuri gray mold disease resistant to mulberry cutting or steamed rice
B&tryL+ne+nerea)-IkI,!
Glue a J piece (diameter 5cm) to a leaf dat and inoculate it (7f piece).
. This was placed under 20C high temperature conditions for 8 days. I looked at the man who was suffering from anxiety. Transmission-★Method and
Calculation of the control value was performed in the same manner as in Test Example 1. As a result, as shown in Table 187, the invention of things is
If the property is tangent to the
Benomyl wayobithi (phanate methyl is a drug)
If the receptivity box is tangential, excellent nr: the control effect is small 1:. Table 7, 5 200' 91,
07 200 100,
01B:200'96'
0 compounds, active ingredients, drug-resistant bacteria, drug-susceptible bacteria, S
Number for when polarized and inoculated (p
pln) 'Fh excluding price meat) Prevention value (copy) 17
200 88 018 2
00' 88 019 2θ0
100 020 200
100' 021 200
97 022, 200 1
00 028 200 88
024 200 100
025 200 97
028 200 97
029' 200 100 0
81' 200 94 082
200 97 088
200 88 084 2
00 84 085 200
91 01
・ 119 ' 200 1 100
01(l lx2o, 200 1 100 ・
01 1 1
121' 200 100:
0 ・'122 1 (1,880 1 Compound Self-active ingredient Concentrates drug-resistant bacteria and drug-resistant bacteria)
Degree If tangent If inoculated〕）No.
(pp+n) vj mackerel value (u,') Pest control value
(%) 124 200 1υ00125
200 94 0126
200 94 n127
200 10u 0128
10 100 0129
200 100 (J130
200 100 0181
200 100
01a2 200 100
0183 200 100
0184 200 100
0185 200 100
01'd6 200 100
0Ia7 200 10 (101
88200, 1000, 145,200, 100, 0 (11 115112oo; too 1 o
□ 1st compound Self-active ingredient Drug resistance Drug GI susceptibility
#11 Sumire: If you have a book, if you are impure.
IJ) 4- -1 IP・u)'lu) Prevention-F-
〇Method Prevention -W (%) 155 10
91 0156 200
□, 970 157 2 (101000. 158200 100, 0159
200 too 0
160 200 100 016
1 200 100
0162 200 100, 011
200 100 0+6
4 200 100 0165
200 100 0166 2
00 100 0167
200 100 016
8 200 100
0+69 200 100
0:16.1 □. . (1ooo. 188 200 100 1
01 1
-189' 200 100 1
019Q'200 100'
Ol --- 19120011000 194200, 100・0'196
200 100 0. 197 200 97,
0198 200 94 1
0 '199 200 10
0 0 '200 200
100' 0201 200
100 ・0202 2
00 100 0 'Test
Experimental example 6 Cucumber vine blight control effect A 90gLt plastic post was filled with sandy loam,
Cucumbers (variety: Aiyoko Hanichi) were sown. m'i this
After cultivation for 8 days, cucumbers with expanded cotyledons were obtained. this
1 seedling Emulsion or water dilution of the test compound in the wettable powder layer
1O was applied per pot and sprayed on the foliage. After chemical solution air drying
, Cucumber vine wilt IP4 with drug resistance or sensitivity to young sapons
g1 (Mycosphaerella m5loni
Glue the bacterial flora section (diameter 6 cm) of s) onto the leaf surface and attach it.
I planted a seed. This was kept in a humid environment at 25℃ for 4 days, and the disease developed.
After treatment, the disease layer was observed. @Disease investigation δ method and control
Calculation of the value was performed in the same manner as in Test Example 1. As a result, as shown in Table 8, the compound of the present invention showed a drug resistance value.
When inoculated, it shows an excellent control effect, and on the contrary, commercially available fungicides
benomyl and thiophanate methyl are drug-friendly
showed excellent control effects when inoculated with 8th Table 1 64 2oo i too
. Test Example 7 Effect on controlling mandarin blue mold disease After washing mandarin fruit (product sI: Unshu) thoroughly with water and air drying it.
, an emulsion of the compound of the present invention or a control commercially available drug was diluted with water.
It was immersed in a chemical solution with a predetermined concentration for 1 minute. After air-drying, two cutlets of drug-resistant or sensitive blue mold lp4@
(Pen+c+l1iuro+talicum)
Conidia were soaked in water and sprayed on the fruit surface.
. After inoculating one room in M room for 14 days, check the severity of the disease as shown in F.
Investigated using disease index of 0.1.2, 8, 4.5.
did. (Stage stage) (Stage index) Lesions
is not recognized 020 next to the surface of the fruit
Lesions are observed below X l〃 20-40
Lesions are observed on the mushrooms 2〃 40-60
〃 8〃 60-80
〃 4〃 80% or more
5 Calculation of disease severity and control value
The test was carried out in the same manner as in Test Example 1. As a result, as shown in Table 9, the compounds of the present invention inhibit drug-resistant bacteria.
When inoculated, it has an excellent control effect, but on the other hand, commercially available
@l benomyl and thiophanate methyl and thia
Bendazole has excellent efficacy when inoculated on drug-susceptible surfaces.
It showed a pesticidal effect. / Table 9 Compound 1 Active ingredient 1. Increasing mulberry injection resistance and drug sensitivity
Number of vaccinations: Number (
ppm) Control value of i (X) Control value (%) 7'20
0 100 0', 8
200 100 015 20
0 100 019
200 100 020
200 100 0
22 10 1t10
024 200 100
028 200 1
00 029 200
100 086 20
0 100 040
200 97 0
Test Example 8 Rice blast control effect A 90-volume plastic pot was filled with rice soil.
Rice (product 11 + Kinki No. 88) was sown. Do this in a greenhouse
A test compound in emulsion form was applied to the 8-leaf stage larvae obtained by cultivation.
Droplets of diluted liquid in water! ! Spray the leaves until it fully adheres to the surface.
After leaving the cloth under humid conditions at 28°C for 8 days, symptoms appeared.
I observed the situation. The disease onset investigation method and control value calculation were carried out in the same manner as Test Example 1.
It was. As a result, as shown in Table 10, the compounds of the present invention showed excellent protection.
It showed a removal effect. 910 Table Test Row 9 Phytotoxicity Test on Crops Fill a 150-capacity plastic pot with sandy loam, and
Wheat (Product 11: Norin No. 61), Rimbu (Shogoku: Kogyoku),
Sow each of the bean nuts (variety: Chiba semi-erect),
Grown in a greenhouse. Emulsion or wettable powder form is applied to the obtained seedlings.
A water diluted solution of the test compound was sprayed on the palm leaves. After spraying, warm up again.
After cultivating for 10 days, the presence or absence of phytotoxicity was determined based on the following criteria.
The investigation was conducted according to the standards. Standards (degree) of drug damage (symptoms) - No abnormalities. (10) Abnormalities caused by chemical damage are observed in some of the crops. Masu: Abnormalities caused by chemical damage are observed throughout the crop. ÷ The plant dies due to medicinal buds. As is clear from Table 11, the compounds of the present invention
No harmful effect on crops was observed, and the chemical used as a control
A commercially available herbicide with a similar structure was found to have phytotoxic effects. / Table 11 Next, N-phenyl carbamate compounds which are compounds of the present invention
(I) and benzimidazole/naof-7nate series
One in the mixing row with agent II and cyclic imide fungicide.
state Benzene used in the following test examples and arrangement examples
Midazole thionolate fungicides and cyclic eids
Thread killing agent 1 is No. 12.)a. 12th crystal b 12-(0,8-methyl test example i
o Cucumber powdery mildew control effect 90-volume Plasti
Fill a pot made with sandy loam, and add cucumber (variety: Sagamihan).
day) was sown. This was cultivated at room temperature for 8 days, and the cotyledons expanded.
I got a video of an open cucumber. This young fungus is emulsified or hydrated.
A droplet of a water diluted solution of the test compound in dosage form is placed on a leaf.
Sprayed on the leaves until a certain amount was attached. After the chemical solution is air-dried, the young bacteria are exposed to
Cucumber powdery mildew @i (5phaeroLhaa&f
ul + g + nea) drug resistance-wayo and susceptibility-
The resulting conidial suspension was inoculated by spraying. This was placed in a greenhouse and cultivated for 10 days to develop the disease, and then the disease appeared.
The shape was observed. The method of onset and location and calculation of control value were carried out in the same manner as the trial mNl.
It was. As a result, as shown in Table 13, the present compound Q no.
Kato, compound person, IB), icl, M,
f average. +F+, A, @ mixed and sprayed
If so, spray them alone (7)
The pest control effect was observed. Test fill Tomato gray mold control effect 90-vol.
Fill a plastic pot with Myokakai soil and add tomatoes (item A1).
= Fortune! No. 2) was sown. This was cultivated in a greenhouse for 4 days,
Obtained the 411th Tomato Samurai. This can be added in emulsion or hydrated form.
A water diluted solution of the test compound of
Sprayed on foliage. II liquid-liquid after air-drying botrytis blight di (Bo
trytis cinerea) drug resistance-and
Conidial liquid obtained by mixing susceptible bacteria was spray inoculated.
. The cylinder developed after being placed in the device for 6 days under 20LfM room conditions.
observed. The disease onset investigation method and control value calculation were carried out in the same manner as Test Example 1.
became. As a result, as shown in Table 14, if any of the compounds of the present invention
, compound (I), (J), (g), or gradient
When sprayed in combination with other substances, when sprayed alone
A superior pest control effect was obtained compared to $ 14 Table 2' 100 142 15 ' 100 182 ・
20 0 15 1 1 22 100 1 8854
20i0 59 100' 32105
LOG 88105
・20 0110
'100 '40117 1
100 88117 1
20:. , , -, , -----, -----, I
-1;-blasphemy -do-2-o-i. 1. o-1
5g-+4; 20+50:
100 ;. −−−−１−−■ −−、、、−、J、、
,, -! 105+1 1 20+50
' 100 1105tJ ' 20+
50'160:110+J',
20+50 '100117↑1
, 20+60 ・100:117+K
l20+60: 100. 141+I 20+50 100
'181)-1'20+50'
100 □ Formulation Example 1 Powder 2 parts of the compound of the present invention 2, 88 parts of clay and 10 parts of talc
If you thoroughly grind and mix the parts, you will get a powder with a base ingredient content of 2%.
. Formulation Example 2 Wettable powder: 80 parts of Compound 15 of the present invention, diatomaceous earth 4511A. 20 parts of white carbon, wetting agent (sodium lauryl sulfate
) 8 parts and dispersant (calcium lignin sulfonate)
By thoroughly grinding and mixing the two parts, a hydrating agent with a base ingredient content of 80X can be obtained.
obtain. Formulation Example 8 Wettable powder: 50 parts of Compound 5 of the present invention, 46 parts of diatomaceous earth, 11 moisturizers (A
2.5 parts of calcium alkylbenzenesulfonate) and
Add 2.5 parts of dispersant (calcium lignin sulfonate)
By pulverizing and mixing, a wettable powder with a base ingredient content of 5ON is obtained. Formulation Example 4 Emulsion 10 parts of the compound 22 of the present invention, 80 parts of cyclohexanone and
and emulsifier (polyoxyethylene alkyl allyl ether)
Blending Example 5 Powder 2 parts of the compound of the present invention 107, 88 parts of clay and talc
10Ii! If you grind and mix well, you will get a powder with a base ingredient content of 2X.
get the agent. Formulation Example 6 Wettable powder: 80 parts of Compound 54 of the present invention, 45 parts of diatomaceous earth, small wide powder
20 parts of carbon, 8 parts of wetting agent (sodium lauryl sulfate) and
2 parts of Diffusion i@I (calcium lignin sulfonate)
By thoroughly grinding and mixing, a wettable powder having a base ingredient content of 80X can be obtained. Formulation Example 7 Wettable powder 50 parts of the present compound 164, diatom ±45 parts, moisture 117
11 (calcium alkylbenzenesulfonate) 2.5
part and dispersant (calcium lignin sulfonate)2.
By thoroughly grinding and mixing 5 parts, a hydrating agent with a base ingredient content of 50X can be obtained.
obtain. Formulation Example 8 Milk 1 part of Compound 101 of the present invention, Cyclohexatsuno 80I
l and emulsifier (polyoxyethylenoalkyl allyl)
If you combine 10ml and 1M, you will get an emulsion with a main ingredient content of 10~
obtain. Formulation Example 9 Powder 2 parts of the present compound 44, 88 parts of clay and 1 part of talc
If 0 parts are thoroughly ground and mixed, a powder with a base ingredient content of 2% can be obtained.
Ru. Formulation Example 1O Wettable powder: 80 parts of the compound 79 of the present invention, ±45 parts of diatom, white powder.
20 parts of carbon, 8 parts of wetting agent (lauryl sulfate sorter) and
Add 2 parts of a dispersant (calcium lignin sulfonate)
By pulverizing and mixing, a wettable powder with a base ingredient content of 80% can be obtained. Formulation Example 11 Wettable powder 50 parts of the present compound 29, diatomaceous earth 451i, 8111
(Calcium alkylbenzenesulfonic acid '7A) 2.5m
l and dispersion # (calcium lignin sulfonate)2.
By thoroughly grinding and mixing 6 parts, it becomes a hydrating agent of Ji5ON containing the main ingredient.
get. Formulation Example 12 Emulsion 1 part of Compound 81 of the present invention, 80 parts of cyclohexanone and
and emulsifier (polyoxyethylene alkyl allyl ether)
If 10 parts are combined, the main ingredient content is 1ON.
Obtain emulsion. Formulation Example 18 1 part of powder compound (15), 1 part for compound, 88 parts of clay,
By thoroughly pulverizing and mixing 10 parts of talc and talc, the main ingredient content becomes 2.
Obtain % powder. Blend Example 14 Powder Reduction material (105) 2%, Compound (2 parts uniformly, Clay 8%)
If 6 parts and 10 parts of talc are thoroughly ground and mixed, -F,
4! A powder with an I content of 4X is obtained. Formulation Example 15 Wettable powder compound (141) 20 m, compound (J) 10 parts, silicon
45 parts of algae, 20 parts of white carbon, wetting agent (Lauri)
8 parts of dispersant (lignin sulfonic acid sorter) and 8 parts of dispersant (lignin sulfonic acid
If you thoroughly grind and mix 2 parts of calcium), the main ingredient content will be 80.
% hydration agent. Formulation example 16 Hydrating agent combination! (181) 10 m, chemical = thing (B)4os,
Silica 11 45 parts, 1ml JR1 (alkylbenzene
2.5 parts of calcium sulfonate) and a dispersant (lignin
By thoroughly grinding and mixing 2.5 parts of calcium sulfonate,
A hydrating agent with a base ingredient content of 50% is obtained. Formulation example 17 Wettable powder compound (54) 25 parts, compound mountain 60 parts, diatomaceous earth 181
1. 1111 fl of wet (alkylbenzenesulfonic acid calcium)
8.6 parts of dispersant (lignin sulfonate)
Lucium) 8.511S is crushed and mixed to contain the main ingredient.
A hydrating agent with an amount of 76% is obtained. Formulation example 18 Wettable powder compound (105) 20 parts, Compound ■80 parts, Powdered Shiro
40 parts sugar, 6 parts white carbon, wetting agent (lauryl sulfate)
8 parts of acid soda) and dispersant (lignin sulfonic acid calcium)
By thoroughly pulverizing and mixing 2 parts of Si), the main ingredient content will be 60%.
Obtain a hydrating powder. Procedural amendment (spontaneous) February 2, 1988, Chief of the Agency, Kazuo Wakasugi, 1, Indication of the case, 1988 Patent H @ 7576s g2, Invention
Name N-phenyl carbamate compound, its production method and
Agricultural and artistic experimental agent 8 containing it as an active ingredient Relationship with the case of the person making the amendment Patent applicant address Address of Osaka Kata 1-ku Kitahama 1-chome lb. Name
<209) Sumitomo Chemical Co., Ltd. Representative Director Takeshi Kamigata 4, Agent address: 5-16 Kitahama, Higashi-ku, Osaka Procedural amendment (
Voluntary) July 7, 1980 L-J l, Indication of the case 1982 Patent application No. 7574j 2 Name of the invention
N-phenyl carbamate compound, its production method, and
Agricultural cough medicine 3 containing it as an active ingredient, and its relationship with the amended case Patent applicant address: 5-chome, Kitahama, Higashi-ku, Osaka
) Sumitomo Chemical Co., Ltd. Representative Hijikata
Takeshi 4, Agent address: 6 Akiji, 5-1 Kitahama, Higashi-ku, Osaka, Contents of amendment: Specification No. 1 submitted in procedural amendment dated July 2, 1988
In the table on page θ1, in the column of physical constants for compound number λ01, / J/! u/, j/A2"-mp41~69℃" is corrected. Written amendment to the above procedure (voluntary) Patent Officer Kazuo Chikusugi1, Indication of the case 1982 Patent-M7F17682, Name of the invention N-phenyl carbamate compound, method for making the same, and
Agricultural pesticide containing it as an active ingredient 8 Relationship with the supplementary case Patent applicant address Address 5-161i Kitaei, Shizuku-ku, Osaka City Name Name
(209) Hijikata, Representative of Sumitomo Chemical Industries, Ltd.
Take 4 agent address: Kitahama 5-chome lb-6, Kiwahito-ku, Osaka, revised pair
the claims of the technical specification and the detailed description of the invention;
Column 6, Contents of amendment (1) 4(2) Correct the scope of claim as shown in the attached sheet
Procedural amendment (written specification) No. 88 dated July 7, 1986
Jj 1!8th line from the bottom between [show,] and 1] 1
Insert a note. [However, X and Y are both bromine atoms and R1 is methyl
group and 2 is wI bulk atom, R2 is propal
R1 is not a gyl group, but X and Y are methoxy groups at the same time
is a methyl group and 2 is an oxygen atom, Ri is
R1 is not a thyl group, but an ethoxy group of X and Y at the same time.
is an ethyl group and 2 is a # group, R2 is an ethyl group.
It is not a chill group (, X1Y is a halogen atom and R1 is a halogen atom)
It is a lower alkyl group which may be substituted with f at the ion atom.
, and when 2 is a sulfur atom, R2 is a methyl group or an ethyl group.
It is not a group, and X#Y is a halogen atom, lower alkali
Kyl group or lower alkoxy group, R1 is lower alkyl group
and when K2 is an oxygen atom, R2 has the general formula -W-
C-R] (in the formula, W+ represents an alkylene group, and R7 represents an alkyl group)
show. ) is not a substituent. ” (21, No. 42
1, the 9th line and the 1st O line of the map say ``wild-''.
Correct each to "wild fungus." (3) Complete the compound number 10 column in Table 1 of Section 59) i.
and delete it. b4) After the column of compound number 21g in Table 1 of the same No. 110
Add the lower F to
Correct it. (6) In Table 4 on page 148, the column for compound number 21 and
Insert the following between the column for control compound (a). [(7) Table 5 of No. 146 Negative, Table 6 of No. 169 Negative of the same
In Table 97 on page 157 of the same, the column for compound number IO is changed accordingly.
Examine all of them. (8) Compound number 218 in Table 7 of No. 169 Negative
Insert the following into the darkness between the column and the column for Benomyl. (9) Compound number lO in Table 8 on page 171 of the same
Delete all fields. Claims (1) General formula [wherein, X and Y are the same or different, a halogen atom, a
alkyl group, lower alkynyl group, lower cyanoalkeni group
group, lower alkynyl group, lower alkoxy group, cyano group
or halogen atom, hydroxyl group or cyano group
a lower substituted with at least one atom or substituent of
alkyl group, or a single substituent represented by the following general formula;
-CH20Rs, -COORaCORg, -CIL
:N-OR@, -CO-Nu-R@ (however, Rs
is a lower alkyl group, a lower alkenyl group, is alkynyl
group, lower haloalkyl group uR4, ms is the same - or
Differently, it represents a lower alkyl group. n is 2.8 or 4
Indicates an integer. 8. represents a hydrogen atom or a lower alkyl group
. ) is shown. 2 represents an oxygen atom or a sulfur atom. R1 is lower alkyl group, lower alkenyl group, lower alkyl group
Any of nyl group, halogen atom, lower alkoxy group
At least one atom of cy group or lower cycloalkyl group
represents a lower alkyl group substituted with a substituent or a substituent. R2
is a 01-C8 alkyl group, a C3-C8 alkenyl group
, C3-C8 alkynyl group, lower cycloalkyl group,
Either lower haloalkenyl group or lower haloalkynyl group
or halogen atom, cyano group, lower alkoxy group
, lower alkenyloxy group, lower haloalkoxy group,
Phenoxy group, lower aralkyloxy group, lower cycloal
substituted with at least 41 atoms or substituents of the kill group
represents a substituted lower alkyl group. However, if X and Y
At the same time, R1 is a methyl group in the bromine atom, and 2 is oxygen
The atoms and Jk, R2 are not propargyl groups, but X and
and X are both a methoxy group and R1 is a methyl group, and
When 2 is an oxygen atom, lL2 is not an ethyl group, but
and Y are both an ethoxy group and R1 is an ethyl group, and
When 2 is an oxygen atom, R2 is not an ethyl group.
. ] An h-phenyl carbamate compound represented by the following. (2) In general formula 6, X and Y are the same or different, a butyl atom, chlorine
atom, bromine atom, atom, child, methyl group, ethyl group,
n-propyl group, n-butyl group, vinyl group, l-prope
Nyl group, 2-propenyl group, ethynyl group, methoxy group,
Ethoxy group, cyano group, 1,2-dibromoethyl group,
Droxymethyl group, cyanomethyl group, 2-cyanoethyl
group, 2-cyanovinyl group, methoxymethyl group, ethoxy
Methyl group, 7lyluoquinemethyl group, propargyloxy
Methyl group, 2-fluoroethoxymethyl group, methoxyca
carbonyl group, ethoxycarbonyl group, allyloxycarboxylic group
Bonyl group, 2-fluoroethoxycarbonyl group, proba
Lugyloxycarbonyl group, dimethoxymethyl group,
Toxymethyl group, ethylenedioxymethyl group, formyl group
group, acetyl group, hydroxyiminomethyl group, methoxy
iminomethyl group, carbamoyl group, N-methylcarbamo
Indicates the yl group. R1 is a methyl group, ethyl group, n-propyl group, allyl group
, propargyl group, 2-butenyl group, 8-butenyl group,
8-butynyl group, difluoromethyl group, 2-chloroethyl group
group, 2.2゜2-trifluoroethyl group, 2-methoxy
R2 represents an ethyl group or a cyclopropylmethyl group.
, methyl group, ethyl group, isopropyl group, bec-butylene
group, allyl group, l-ethylpropyl group, 1-ethyl-
2-propynyl group, 1-methyl-2-propynyl group, l
-methyl-butyl group, l-methyl-pentyl group, l-methyl
thyl-heptyl group, l-methyl-2-propenyl group,
Lopargyl group, 2-butenyl group, l-methyl-8-butene
Nyl &, 1-pentyl-2-propenyl group, 2-butini
l &, 8-bunanyl group, l-methyl-8-butynyl group,
l-butyl-2-propynyl group, l-pentyl-2-propynyl group
Ropinyl group, cyclobutyl group, 2-cyanoethyl group, 2
-Fluoroethyl group, 2-chloroethyl group, 2-bromo
Ethyl group. 2.2.2-trifluoroethyl group, l-fluoromethi
-2-fluoroethyl i,l-chloromethylethyl group
, l-promomethylpOpi)LM, 1-methoxymethyl
-2-chloroethyl group, 4-chloro-2-butenyl group,
4-chloro-2-butynyl group, 1-cyclopropylethyl group
group, l-cyclopentylethyl group, 2-n-propo
xyethyl group, 2-isopropoxyethyl group, 2-aryl
2-methoxyethyl group, 2-methoxyethyl &, 2-(2-
chloroethoxy)ethyl group, 2-benzyloxyethyl
group, l-methyl-2-methoxyethyl group, 1-methyl-
2-n-butoxyethyl group, l-methyl-2-phenokyl group
Indicates ethyl group. 2 represents an oxygen atom or a sulfur atom. However, X and Y
is a bromine atom, R1 is a methyl group, and G2 is an acid
The elementary atom iRl is not a propargyl group, but
Y is a methoxy group and R1 is a methyl group, and
is an oxygen atom, R2 is not an ethyl group (,
Y is an ethoxy group, R1 is an ethyl group, and 2
is an oxygen atom, R2 is not an ethyl group, and
, Y), and when 2 is #l elementary atom, R2 is 2-button.
In the first paragraph of the patent claim shown in
Carbamate compounds. (3) General formula [wherein, X and Y are the same or different, chlorine atom, bromine atom]
child, one elementary atom, methyl group, ethyl group, n-propyl group
, 1-propenyl group, vinyl group, allyl group, ethynyl group
, methoxy group, cyano group, 1,2-dibromoethyl group,
Methoxymethyl group, methoxycarbonyl group, dimethoxy
Methyl group, jetoxymethyl group. Indicates an acetyl group and a methoxyiminomethyl group. ILl hamethyl group, ethyl group, allyl group, propargyl group
group, difluoromethyl group, and 2-chloroethyl group. R2 is a methyl group, ethyl group, isopropyl group, 5eG-
Butyl group, allyl group, l-ethylpropyl &, 1-ethyl group
-2-propynyl group, 1-methyl-2-propynyl group
, l-methyl-2-proveniJvM, -propalkyl group
, 2-butenyl group, 2-butynyl group, 1-methyl-8-
Butynyl group, 2-cyanoethyl group, l-fluoro-methylene group
-2-fluoroethyl group, 1-fluoromethyl-2-
Fluoroethyl group, l-chloromethylethyl group,
Toxymethyl-2-chloroethyl group, 4-chloro-2-
Butynyl group, l-cyclopropylethyl group, 2-'' (2
-chloroethoxy)ethyl group, 1-methyl-2-methoxy
Ethyl group, ■-methyl-2-methoxyethyl group, ■-
Indicates methyl-2-n-butoxy ether group. however
, X and Y are both bromine atoms and R1 is a methyl group
When, auxiliary is not a propargyl group, and X and Y are
At the same time, when R1 is a methoxy group and R1 is a methyl group, R2 is
Instead of an ethyl group, X and X are simultaneously ethoxy
Claim No. 1 in which R1 is an ethyl group
N-phenyl carbamate system according to item 1 or item 2
Compound. (4) General formula [wherein, when X is a methoxy group or an ethoxy group, Y is a salt
elementary atom, bromine atom, methyl group, ethyl group, n-propyl
group, methoxy group, ethoxy group, Schiff) group, methoxymethy
group, methoxycarbonyl group, dimethoxymethyl group,
Indicates an acetyl group. R1 is ethyl group, allyl group, propane group
Indicates alkyl group and 2-chloroethyl group. Phantom is methyl group, ethyl group, isopropyl group, 5ee-butyl group
thyl group, allyl group, l-methyl-2-propenyl group, l
-Methyl-2-propynyl group, propargyl group, 2-methyl
Anoethyl group, 2-butynyl group, 4-chloro-2-butyl group
Indicates a nyl group and a l-methyl-2-methoxyethyl group. Ta
However, X and Y are both ethoxy groups, and R1 is an ethoxy group.
When it is a thyl group, 11 is ethyl. ] Claims @lJJ[, @paragraph 1 or section 2]
Item 8 is a softening N-phenyl carbamate compound. (5) General formula [wherein, X and Y are the same or different, chlorine atom, bromine atom]
child, methyl group, ethyl group, n-propyl group, methoxymethane
Represents a thyl group, R1 is an ethyl group, an allyl group, a propal
Indicates a gyl group and a 2-chloroethyl group. R2 is a methyl group,
Ethyl group, isopropyl group, 5ee-butyl group, allyl group
group, 1-methyl-2-propenyl group, l-methyl-2-
propynyl group, propargyl group, 2-cyanoethyl group,
2-butynyl group, 4-chloro-2-butynyl group, l-methyl
Indicates thyl-2-methoxyethyl group. j2% X
1&, R2 is not a 2-butynyl group. ]
N according to claim 1, 2 or fm8
-Phenyl carbamate compounds. (6) 'I of the compound shown in claim 4
Y is a chlorine atom, a methyl group, a methoxymethyl group, or
A compound that is a cyano group. (7) Scope of patent l11tX [changes shown in paragraph 15]
Among the compounds, X and Y are the same or different, chlorine atom, metal
A compound that is a thyl group or a methoxymethyl group. (81%% of the compound shown in item 6 of the patent scope)
” is an ethyl group.
A compound in which R1 is an ethyl group. QQ General formula [In the formula, X and Y are the same or different, a halogen atom, a
alkyl island, lower alkenyl group, lower cyanoalkeni
group, lower alkynyl group, lower alkoxy group, cyano group
or halogen atom, hydroxyl group or cyano group
a lower substituted with at least one atom or substituent of
alkyl group, or a substituent represented by the following general formula;
-CH10R3, -COOR3. C0NB-bens, -CH=NORg (however, R
3 is lower alkyl group, lower alkenyl group, lower alkynyl group
represents a lower haloalkyl group. R4 and ILIs are the same
- or, differently, a lower alkyl group. n is 2.8 or
indicates an integer of 4. - is a hydrogen atom or a lower alkyl group
shows. ) is shown. R1 is a lower alkyl group, a lower alkenyl group, a lower
alkynyl group, halogen atom, lower alkynyl group, or halogen atom, lower alkynyl group,
At least one of alkoxy groups or lower cycloalkyl groups
Indicates a lower alkyl group substituted with 5 atoms or substituents
. ] and the general formula % formula % [wherein R2 is a C1-C8 alkyl group, a C3-C8 alkyl group]
Alkenyl group, 03-CB alkynyl group, lower cyclo
Alkyl group, lower haloalkenyl <It class haloal
Either a quinyl group, a halogen atom, a cyano group,
Lower alkoxy group, lower alkenyloxy group, lower 71
0 alkoxy group, phenoxy group, lower araloxy group,
At least one atom of the lower cycloalkyl group or
Indicates a lower alkyl group substituted with a substituent. 2 is oxygen source
indicates a sulfur atom or a sulfur atom. ] Chloroformic acid ester or chloroformic acid thioester represented by
[In the formula, X, Y,
The set R2,Z has the same meaning as above. however
, X and Y are both bromine atoms and R1 is a methyl group,
, and when 2 is an oxygen atom, R2 is a propargyl group
No, X and Y are methoxy groups and R1 is methyl group.
and when 2 is an oxygen atom, R2 is an ethyl group
No, X and Y are ethoxy groups and R1 is ethyl group.
and when there are two oxygen atoms, R2 is an ethyl group
Production of N-phenyl carbamate compounds represented by
Law. (b) General formula lower cyanoalkenyl group, lower alkynyl group, lower alkyl group
Either a koxy group or a cyano group, or
At least one of Jlf child, hydroxyl group or cyano group
a lower furkyl group substituted with a substituent or a substituent, or
Substituents represented by the general formula; -CHzORa, -C
OOR3. -CONH-Ri, -CH:N0Ra (however,
Recommendations are lower alkyl 1, lower alkenyl group, lower alkynyl group
represents a lower haloalkyl group. R4 and R4 are the same or
are different and indicate a lower alkyl group. n is 2, 8 or
Indicates an integer of 4. Rs is a hydrogen atom or a lower alkyl group
show. ) is shown. R1 is a lower alkyl group, a lower alkenyl group, a lower
alkynyl group, halogen atom, lower alkynyl group, or halogen atom, lower alkynyl group,
At least one of alkoxy groups or lower cycloalkyl groups
The parent atoms indicate a lower alkyl group substituted with & substituent
, ] phenylisonane r-ms body and general
Formula [In the formula, 2 is I! ! 8R2 indicating a bulky atom or a sulfur atom is
C1-C8 alkyl group, 03-C8 alkenyl group,
C3-C8 alkynyl i, ia cycloalkyl group, low
Either the class cyloalkyl group or the lower haloalkynyl group,
Or halogen atom, cyano group, lower alkoxy group, lower
alkenyloxy group, lower halalkoxy group, phenol
xy group, lower aralkyloquine group, lower cycloalkyl
substituted with at least a tl- atom or substituent among the groups
represents a lower alkyl group. ] Alcohol derivative or thioalcohol derivative represented by
A general formula characterized by reacting with [wherein, X, Y, R1, R2, Z
have the same meaning. However, X and Y are bromine atoms at the same time.
When R1 is a methyl group and 2 is an oxygen atom,
R2 is not a propargyl group (, X and Y are
Toxy group, R1 is a methyl group, and 2 is an oxygen atom
When R2 is not an ethyl group and X and Y are simultaneously ethyl
Toxy group, R1 is ethyl group, and 2 is oxygen atom
When, R2 is not an ethyl group, and 2 is a sulfur group
When a child, R2 is not a substituent. ] A method for producing an N-phenyl carbamate compound represented by
. (b) General formula N atom, lower alkyl group, lower alkenyl group, lower sia
noalkenyl a, lower alkynyl group, lower alkoxy
group, cyano group, halogen atom, hydroxyl group
or substituted with at least one atom or substituent of the cyano group
substituted lower alkyl group, or the level shown in the general formula below.
-CH20R3, -COORa. -CONfi-Rs, -CB=NORg (however
, R3 is a lower alkyl group, a lower alkenyl group, a lower alkyl group,
Indicates a quinyl group or a lower haloalkyl group. R4 and Rs are the same
- or, differently, represents a lower alkyl group. n is 2.8 or
represents a 4c integer, R- is a water bulk atom or lower alkyl
Indicates a group. ) is shown. R1 is a lower alkyl group, a lower alkenyl group, a lower
alkynyl group, halogen atom, lower alkynyl group, or halogen atom, lower alkynyl group,
At least one of alkoxy groups or lower cycloalkyl groups
Substituted with atoms or substituents! This represents a lower alkyl group.
The aniline derivative represented by ] is reacted with phosgene.
General formula obtained by [where R1, X and Y have the same meanings as above]. ] A phenyl isocyanate derivative represented by the general formula [wherein 2 represents an oxygen atom or a sulfur atom]. R2 is a C1-C8 alkyl group, 03-C11 alkyl group
Nyl group, 03-C8 alkynyl group, lower cycloalkyl group
group, lower haloalkenyl group, lower haloalkynyl group.
Either or halogen atom, cyano group, lower alkyl
xy group, lower alkenyloxy group, lower haloalkoxy group
group, phenoxy group, lower aralkyloxy group, lower
At least 1m atoms or substituents of the loalkyl group
Indicates a substituted lower alkyl group. ] An alcohol derivative or a thialfur derivative represented by
[In the formula, X, Y * Rt e R2a Z Ha front]
has the same meaning as described above, except that X and Y are
When R1 is a methyl group and 2 is an oxygen atom,
Y-lL! is not a propargyl group, tt=1 or
and Y are both a methoxy group and iLt is a methyl group,
and when 2 is an oxygen atom, R2 is ethyl group and 2<
+ Kiboodan 1 and Y are ethoxy groups and the group is ethyl group
, and 2 is an oxygen atom.
R at rogen atom, lower alkyl group or lower alkoxy group
When 1 is a lower alkyl group and 2 is an oxygen atom,
R2 has the general formula -W-C"=C-)L? (wherein, W is
It represents an alkylene group, and R7 represents an alkyl group. )in
Not the substituent shown. ] A method for producing an N-7-enyl carpamate compound represented by
4 (To) General formula [wherein, X is a halogen atom, a lower alkyl group, a lower alkyl group]
Kenyl group, lower cyanoalkenyl group, lower alkynyl group
, lower alkoxy group, cyano group, or halo
At least one atom of a gen atom, a hydroxyl group, or a cyano group
a lower alkyl group substituted with a substituent or a substituent, or
ii Hou group represented by the general formula; CH20R3゜-CO
Rs, -CH=N-ORi, -CONHR
g (However, R8 is a lower alkyl group, lower alkenyl h
, lower alkynyl group, lower haloalkyl group. fL
a, ms are the same or different, lower alkyl group
vinegar. D indicates 2.8 or 4. ) Lm is an atom or
Represents any lower alkyl group. ) is shown. 2 represents an oxygen atom or a sulfur atom. R1 is lower alkyl group, lower alkenyl group, lower alkyl group
Either of the nyl groups, halogen atoms, lower alkoxy
At least one atom of cy group or lower cycloalkyl group
Indicates a lower alkyl group substituted with a child or a substituent. R
2 is a 01-C8 alkyl group, 03-C, alkenyl
1ca-Cs alkynyl group, lower cycloalkyl group,
Either lower haloalkenyl a or lower cyloalkyl group
or halogen atom, cyano group, lower alkoxy group
, lower alkenyloxy group, lower haloalkoxy group,
Phenoxy group, lower aralkyloxy group, lower cycloal
At least one atom of the kill group is substituted with a substituent.
represents a substituted lower alkyl group. ] 6N-phenyl carbamate compound and hydro
React with xylamine or lower alkoxyamine
A general formula characterized in that, in the formula, X, lx, R
2 and Z have the same meaning as above. Yl is hydroxy
Indicates an iminomethyl group or lower alkoxyiminomethyl group.
vinegar. ] Production of N-phenylcarbamate compound represented by
Law. (b) General formula % formula % [In the formula, X and Y are the same or different, a halogen atom, a
alkyl group, lower alkenyl group, lower cyanoalkeni group
group, lower alkynyl group, lower alkoxy group, cyano group
or halogen atom, hydroxyl group or cyano group
Substituted with at least one atom or substituent
class alkyl group, or fIt substituent represented by the following general formula
;-CH20R3,-COOR3゜-CI(=N-UR
s, -Co-NH-11s (however, R3 is lower
Alkyl group, lower alkenyl i, ia alkynyl group, lower
represents a haloalkyl group. R4, ms are the same or different
and lower alkyl funds. n represents 2, 8 or 4,
R6 represents either a water ice atom or a lower alkyl group
Was. ) is shown. 2 represents an oxygen atom or a sulfur atom. R1 is lower alkyl group, lower alkenyl group, lower alkyl group
Any of the nyl group, or 710yn atom, lower alkoxy
At least one of the xyl group or lower cyfucoalkyl group
1 represents a lower alkyl group in which 4 is replaced with an atom or substituent
．． R2 is C1-C8 alkyl fi, C3-C8 alkyl
Kenyl group, C3-C8 alkynyl & lower cycloal
Kill group, lower haloalkenyl group, lower haloalkynyl group
or halogen atom, cyano group, lower alkali
Koxy group, lower alkenyloxy group, lower haloalkoxy group
Cy group, phenoxy group, lower aralkyloxy group, lower silicon group
At least one atom or substitution in the chloroalkyl group
The lower alkyl substituted with a group is not an ethyl group, but an
and Y at the same time? Nose - Mar Port 1 - T - Fire Zen
-Ma-voice-Li-yo-ka-) -Z-ps,]
A pesticide for agricultural roofing that contains % mold. ) General formula [wherein, X and Y are the same or different, a halogen atom, a
alkyl group, lower alkenyl group, lower cyanoalkeni group
Group i Class alkynyl group, lower alkoxy group, cyano group
or halogen atom, hydroxyl group or cyano group
lower substituted with at least one atom or substituent of
an alkyl group or a 1f substituent represented by the following general formula;
-CH20R3, -00013. -CH=h-ORs, -CO-Nu-R・(just
However, the intuition is lower alkyl group, lower alkenyl M, lower alkyl group.
Indicates a quinyl group or a lower haloalkyl group. R4, R4, is
Same or different, represents a lower alkyl group. ! 1 is 2.
Shows 8 or 4. Rc is a hydrogen atom or a lower alkyl group
Represents either. ) is shown. 2 represents an oxygen atom or a sulfur atom. lLl is a lower alkyl group, a lower alkenyl group, a lower alkyl group,
Any of the quinyl groups, halogen atoms, lower alkyl
At least one of the xy group or lower cycloalkyl group
Indicates a lower alkyl group substituted with an atom or a substituent. R
2 is 01-C8 alkyl group, C3-Cs alkenyl
group, C3-C8 alkynyl i,atecycloalkyl
group, lower haloalkenyl group, lower haloalkynyl group.
Either or halogen atom, cyano group, lower alkyl
xy group, lower alkenyloxy group, lower haloalkoxy group
group, phenoxy group, lower aralkyloxy group, lower
At least one atom or substituent of a loalkyl group
represents a lower alkyl group substituted with However, X and
Y is 1 town of bromine] 6 at the same time, 3-4-fu,! death
Part 2
T h-')-,,,;;,,2-Z-bS!
-IPII, $'F p, -? -h s -hot water
x and Y are simultaneously etho-
Ki Voice-11 Snoring-Gin 4” Seat! k 'j &"'
Q-i town-h--ka-te λ-mau... ! ! L turtle” 59
Point j, R21;
Even if R1 is substituted with a halogen atom
A good lower alkyl atom, a lower alkyl group
or a lower alkoxy group and R1 is a lower alkyl group.
, and when 2 is an oxygen atom, R2 has the general formula -W-CmiC-R? (In the formula, W represents an alkylene group.
, R7 is a substituent represented by D ) representing an alkyl group
It is effective to use N-phenyl carb<mate compounds shown in
The scope of patent M, which is characterized by containing as a component,
Benzimidazole thiophanate type according to item 14
Carbonicide-resistant soda or cyclic imide-based fungicide-resistant bacteria control agent. Sakaki General formula [In the formula, X and Y are the same or different, Norogen atom,
Lower alkyl group, lower alkenyl group, lower cyanoalke
Nyl group, lower alkynyl group, lower alkoxy group, cyano
any of the groups, or a halogen atom, a hydroxyl group, or a cyano
a group substituted with at least one atom or substituent;
alkyl group, or represented by the following general formula -CON)iR
s (However, Ra is a lower alkyl group, a lower alkenyl group
, lower alkynyl group, lower haloalkyl group. R4
, Rs are the same or different and represent a lower alkyl group. U
indicates 2.8 or 4, Re is a water bulk atom or a lower atom
Represents any alkyl group. ) is shown. al is a lower alkyl group, a lower alkenyl group, a lower
alkynyl group, halogen atom, lower alkynyl group, or halogen atom, lower alkynyl group,
At least one of alkoxy groups or lower cycloalkyl groups
atoms or R2 is a C1-Ca alkyl group, C3-C8
alkenyl group, 03-CI alkynyl group, lower cyclo
Loalkyl group, lower haloalkenyl group, lower haloalkyl group
or a halogen atom, a cyano group, or a lower
Alkoxy group, lower alkenyloxy group, lower haloal
koxy group, phenoxy fi, lower aralkyloxy group,
At least one atom of the lower cycloalkyl group or
The lower a substituted with a substituent is a methyl group, and the
When 2 is # element, R-2 is not an ethyl group but
and Y are both an ethoxy group and R1 is an ethyl group, and
#2 is an oxygen atom, R2 is not an ethyl group, it is Y or halo
Gen atom, lower alkyl group or lower -W-CmiC-Rt
(In the formula, W represents an alkylene group, and iL7 is an alkylene group.
Indicates a group. ) is not a substituent. ] Types of N-phenyl carbamate compounds represented by
In addition to the above, pensimidazole/thiophanate fungicides
% indicates that it contains one or more of these as active ingredients.
Agriculture! Disinfectant composition for one line. 0 general formula [wherein, X and Y are the same or different, a halogen atom, a
alkyl group, lower alkenyl group, lower cyanoalkeni group
group, lower alkynyl group, lower alkoxy group, cyano group
or halogen atom, hydroxyl group or cyano group
lower substituted with at least one atom or substituent of
An alkyl group or a substituent represented by the following general formula;
-C1l1120R3, -COOR3. -Cki=N-ORi, -CO-NH-R@(ta
However, R3 is a lower alkyl group, a lower alkenyl group, a lower
Indicates an alkynyl group or a lower haloalkyl group. R4, Rs.
are the same or different and represent a lower alkyl group. n is 2.
Shows 8 or 4. R@ is a hydrogen atom or a lower alkyl group
Raise one of them. ) is shown. 2 represents a #I atom or a sulfur atom. R, is lower alkyl group, lower alkenyl group, lower alkyl group
Any of nyl group, halogen atom, lower alkoxy group
At least one atom of cy group or lower cycloalkyl group
represents a lower alkyl group substituted with a substituent or a substituent. R2
is a C1-Cs alkylkenyl group, a C3-Cs alkynyl group, lower cyclo
Alkyl group, lower haloalkenyl group, lower haloalkyny
or halogen atom, cyano group, lower
Alkoxy group, lower alkenyloxy group, lower haloal
koxy group, phenoxy group, lower aralkyloxy group, lower
At least ill atoms of the class cycloalkyl group or
is lower alkyl substituted with a substituent, and 2 is a sulfur group
The child's j, R2 is methyl. When 2 is an oxygen atom, R2 is
ls of N-phenyl carbamate compounds represented by the general formula
The above and one or more types of cyclic imide general soda agents are used as active ingredients.
1. A composition for use in a certain farm, characterized by comprising:

Claims (1)

[Scope of Claims] (1) General formula [wherein X and Y are the same or different, halogen atom, lower alkyl group, lower alkenyl x, lower cycloalkyl group, lower alkynyl crystal, lower alkoxy group, cyano or lower alkyl substituted with at least one atom or substituent among a halogen atom, a hydroxyl group, or a cyano group.1. or a substituted JiJ- represented by the following general formula
CsiORm. -0OL) Ri, -CB<H:, -0■<
”:;((]h+)n, shout-9-C■=N-(JR
@ - ( represents an alkyl group. n represents an integer of 2, 8 or 4. VL6 represents a hydrogen atom or a lower alkyl group). 2 represents an oxygen atom or a sulfur atom. 1LlI represents an alkenyl group, a lower arginyl group, or a lower alkyl group substituted with at least one atom or substituent 1 among atom, lower alkoxy group, or lower cycloalkyl group. Any of the following: 01-CI Al 1 CIt-C8 alkenyl group, Cm-C- alkynyl group, lower cycloalkyl lh, g-class haloalkenyl i, am haloalkynyl group, or a halogen atom. Cyano group, lower Alkoxy group, lower alkenyloxy &
, me haloalkoxy group, phenokidim, lower aralkyloxy group, and lower cycloalkyl group.
represents a lower alkyl group substituted with 2 atoms or substituents, provided that when X and Y are both a bromine atom, R1 is a methyl group, and 2 is an oxygen atom, Rg is not a propargyl group, and When X and Y are both methoxy groups, kLl is a methyl group, and 2 is an oxygen atom, @
, R1 is not an ethyl group, X and Y are both ethoxy groups, R1 is an ethyl group, and 2 and 2 are not ethyl groups. ] An N-7-enylcarbamate compound represented by the following. (2) General formula [where x and Y are the same or different, fluorine atom, chlorine atom, bromine atom, iodine atom, methyl group, ethyl group, n
-Propyl group, n-butyl group, vinyl chloride, l-propenyl group, 2-propenyl group, ethynyl 1, methquine group, ethoxy group, cyano &, 1,2-dibromoethyl group, hydroxymethyl 1, noatzmethyl group, 2 -cyanoethyl group, 2-noanovinyl 1, methoxymethyl group, ethoxymethyl group, allyl oxine methyl group, propargyl oxine methyl group, 2-fluoroethoxymethyl group, methquin carbonyl group, ethoxycarbonyl group, allyl oxine carbonyl group, 2 -Fluoroethoxycarbonyl group, propargylox7carbonyl group, jetoxymethyl group, jetoxymethyl group, ethylenodiokylemethyl group, formyl group, acetyl group, hydroxyiminomethyl 1, methquinoiminomethyl group, carbamoyl group, N -Represents a methylcarbamoyl group. R1 is a methyl group, ethyl 1, n-propyl group, allyl group, flopargyl group, 2-butenyl group, 8
-butenyl M, a-butynyl group, difluoromethyl group,
2-chloroethyl group, 212.2-)lifluoroethyl group, 2-methoxyethyl group, and cyclopropylmethyl group. Rm is a methyl group, an ethyl group, an isopropyl group,
5ee-butyl group, allyl group, l-ethylpropyl &
, 1-ethyl-2-propynyl group, 1-methyl-2-propynyl Jk, 1-methyl-butyl group, l-methyl-penothyl &, t-methyl-hebutyl M, 1-methyl-2
-propenyl group, propargyl group, 2-butenyl 1,l
-Methyl-8-butenyl group, l-pentyl-2-propenyl group, 2-butynyl group, 8-butynyl group, 1-methyl-8-butynyl group, 1-butyl-2-propynyl group, 1
-pentyl-2-propynyl group, cyclobutyl group, 2-
Cyanoethyl group, 2-fluoroethyl group, 2-chloroethyl group, 2-bromoethyl &, 2゜2.2-trifluoroethyl group, l-fluoromethyl-2-fluoroethyl group, 1-chloromethylethyl group, 1- 70 momethylbrobyl group, 1-methoxymethyl-2-chloroethyl group, 4
-”Rolow 2-funyl group, 4-chloro-2-butynyl group, 1-cyclopropylmethyl group, 1-cyclope/thylethyl group, 2-n-propoxyethyl group, 2-isopropoquinethyl group, 2-allyloquino Ethylum, 2-methoxyethyl group, 2-(2-chloroethquino)ethyl group,
2-benzyloxyethyl group, l-methyl-2-methoxyethyl group, 1-methyl-2-n-methoxyethyl group,
Indicates a 1-methyl-2-phenoxyethyl group. 2 represents an oxygen atom or a sulfur atom. t: t, X and Y are both a bromine atom, fLl is a methyl group, and 2 is an oxygen atom, and 2 is not a propargyl group; group, and when 2 is an oxygen atom, the loss is not an ethyl group, but also
and Y is an ethoxy group and R1 is an ethyl group,
and when 2 is an oxygen atom, lh is not an ethyl group. ] The N-phenyl carbamate compound according to claim 1, which is represented by: (8) General formula [wherein X, Yl, i are the same or different, chlorine atom, bromine atom, iodine atom, ethyl group, ethyl group, n-propyl group, 1-propenyl group, vinyl group, allyl group , ethynyl 1, metquin group, ethoxy group, cyan M, 1. 2-dibromoethyl group, methoxyethyl group, methoxycarbonyl group, dimethoxymethyl group, dimethoxymethyl group, acetyl group, methoxyiminomethyl group, R1
represents methyl group, ethyl group, allyl group, flopargyl group, difluoromethyl group %2-chloroethyl group, R1 represents methyl crystal, ethyl group, isopropyl group, 5ea-butyl 1, allyl group, l-ethylpropyl group, 1 -ethyl-2
-propynyl group, 1-methyl-2-propynyl &, 1-
Methyl-2-propenyl group, propargyl group, 1-butenyl M, 2-butynyl group, 1-methyl-8-butynyl group, 2-cyanoethyl &, 1-fluoromethyl-2-fluoroethyl group, l-fluoromethyl-2 -Fluoroethyl group, l-chloromethylethyl 4.1-methoquinomethyl-2-chloroethyl! , 4-'rolo-2--/thinyl group, l-cyclopropylethyl! , 2-(2-'70ethyne)ethyl &, 1-methyl-2-methoxyethyl 1
, l-methyl-2-methoxyethyl group, l-methyl-2
-True-1-rubutoxyethyl M. However, since X and Y are both R atoms and R+ is a methyl group, the stone is pro-(not a lugyl group, and also X and Y
is simultaneously a methoxy group and R1 is a methyl group), R
1 is not an ethyl group, and furthermore, X and Y are not ethyl groups at the same time. ] Claims 1 or 1 to I [N-phenyl car according to item 2] (mate compound) (4) General formula [wherein, when X is a methoxy group or an ethoxy group, Y represents a chlorine atom, a bromine atom, an ethyl group, an ethyl group, an n-propyl group, a methoxy group, an ethoxy group, a cyano group, a methoxymethyl group, a methoxycarbonyl group, a dimethoxymethyl group, or an acetyl group. R1 represents an ethyl group; It represents an allyl group, a flopargyl group, and a 2-chloroethyl group.R1 is a methyl group,
Ethyl group, isopropyl group, 5ea-butyl group, allyl group, 1-methyl-2-propenyl group, 1-methyl-2-
propynyl l propargyl group, 2-noanoethyl group,
2-butynyl group, 4-chloro-2-butynyl group, 1-methyl-2-methoxymethyl group; N- as defined in claim 1, 2 or 8, where RB is ethyl group and is represented by 1 (A0).
Phenylcanomate compounds. (5) General formula [wherein X and Y are the same or different from 1, and represent a chlorine atom, a bromine atom, a methyl group, an ethyl group, an n-propyl group, or a methoxymethyl group. R1 is an ethyl group, an ant J Shibrow, a blow<+regyl group,
Indicates a 2-chloroethyl group. aS (Yomethyl group, ethyl group, isopropyl group, 5ee-butyl group, allyl group, 1-methyl-2-propenyl group, 1-methyl-2-propynyl group, pr'' (ru A' group, 2-cyanoenal group, 2-funanyl group, 4-loro-2-butynyl group, 1
-Methyl-2-methoxymethyl group. ] A combination of N-phenylcarbamate yarns comprising claim 181, claim 2, or Hs + σ. (6) Among the compounds shown in claim 4,
A compound in which 1 is a salt Xi, a methyl group, a methoxymethyl group, or a cyano group. (7) Among the compounds shown in Claim 5 of the Special IFF, a compound in which X and Y are the same or different and are a chlorine atom, a methyl group, or a methoxymethyl group. (8) A compound in which ILt is an ethyl group, which is the other side of the compound shown in item 6 of the scope of patent purchase. (9) Among the compounds shown in claim 7, a compound in which the loss is an ethyl group. (10) General formula Geno atom, lower alkyl group, lower alkenyl group, (mM
7-noalkenyl group, lower alkyl group, lower alkokene group, cyano group, or at least one atom of halogen atom, hydroxyl group or cyano group or substituted M5
A lower alkyl group substituted with It, or a 1M group represented by the general formula F; -CH20Ri. -C01Ls, -(Kyuho L[-fLi, -
Cm2No) La (Tagoshi, R1 is a lower alkyl group,
Lower alkenyl group, lower alkynyl group, a-class halolkyl group. iL4 and Ra are the same or different and represent a lower alkyl group; n represents an integer of 2.8 or 4; R6 represents a hydrogen atom or a lower alkyl group. ) is shown. hl is a lower alkyl group, a lower alkenyl group, a lower alkynyl group, or at least one of a halogen atom, a lower alkoxy group, or a lower cycloalkyl group.
represents a lower alkyl group substituted with 5 atoms or substituents. ] An aniline braided conductor represented by the general formula % formula % C, where R1 is an alkyl group of 01 to Ca, an alkenyl group of 01 to Cm, an alkynyl group of Cm to C-, a lower cycloalkyl group, a lower haloalkenyl a lower haloalkynyl group, or at least one of a halogen atom, a cyano group, a lower alkoxy group, a lower alkenyloxy group, a lower haloalkoxy group, a phenoxy group, a lower aralkyloxy group, or a lower cycloalkyl group. represents a lower alkyl group substituted with an atom or substituent. 2 represents an oxygen atom or a sulfur atom. ] [wherein X, Y, R1, Rm, Zl! 11
It has the same meaning as the description above. t, X and Y, 6 (at the same time, Rs is a bromine atom,
2 is an oxygen atom, Rm is not a brono<A gyl group, and X and Y are simultaneously methoxy groups and R
When 1 is a methyl group and 2 is ≦ an oxygen atom, 1 is not an ethyl group, and furthermore, X and Y are both ethoxy groups and R1 is a methyl group and Z is an oxygen atom. , not a ethyl group.] 'Qy, a method for producing an h-phenyl carnimate compound. (U) General formula [wherein, X and Y are the same or different, a norogeno atom,
Substituted with any of a lower alkyl group, a lower alkenyl group, a lower cyanoalkenyl group, a lower alkynyl group, a lower alkoxy group, a cyano group, or at least 1@ atoms or substituents among a halogen atom, a hydroxyl group, or a cyano group. lower alkyl group, or a substituent H- represented by the following general formula
(1mORm. −(XJR@, −(X)Nu−R@, −100 million = NUR@
(However, Rs represents a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a 4ffi haloalkyl group. & , fLi are the same or different and represent a lower alkyl group, Ill is an integer of 2.8 or 4 , R- represents a hydrogen atom or a lower alkyl group). R1 is a lower alkyl group, a lower alkenyl group, a lower alkynyl group, or at least one of a halogen atom, a lower alkoxy group, or a lower cycloalkyl group
represents a lower acyl group substituted with 5 atoms or substituents. ] A phenyl isocyanate derivative represented by the general formula [wherein 2 represents an oxygen atom or a sulfur atom]. Recommendations include an alkyl group of 01 to CI, an alkenyl group of Cs to C@, an alkynyl group of Cs to Cm, a lower alkyl group, a lower haloalkenyl crystal, a lower haloalkynyl group, or a halogen atom, cyano Ik, Low grade 71L
: Represents a lower alkyl group substituted with at least lIl atoms or substituents among 1xy group, lower alkenyloxy group, lower Isroalkoxy group, phenoxyi, lower alkyloxy group, and lower cycloalkyl group. ] A general formula characterized by reacting with an alcohol derivative or a thioalcohol haze conductor represented by
! 111 has the same meaning as mentioned above. However, X and Y
b (simultaneously a bromine atom and R1 is a methyl group, and force) 2
is an oxygen atom and the R meaning is prono (not a rugyl group,
In addition, when X and Y forces 5 are simultaneously methoxy groups, R1 is a methyl group, and 2 is an oxygen atom, Ill is an ethyl group and not 1, and furthermore, When it is an ethyl group and 2 is an oxygen atom,
Tsutomu is not a methyl group. ] A method for producing an N-phenylcano (mate compound) represented by the general formula [wherein, A substituent represented by the general formula below, lower alkyl substituted with at least 1 of a lower alkoxy group, a cyano group, or a substituent of at least 1 of 10 atoms, a hydroxyl group, or a cyano group. , -CutORm. -(X)R@, -(X)NH-fLi, -CH=N
OKs (r: dashi, meaning lower alkynyl group, lower alkynyl group, lower alkynyl group, lower) 10 indicates an alkyl group. R4 and Rs are the same or (very different, and represent a lower alkyl group. nl represents an integer of 2.8 or 4. R4 represents a hydrogen atom or a lower alkyl group as I), Rt represents a lower alkyl group. Alkyl group, lower alkenyl 1,
It represents a lower alkyl group substituted with at least one atom or substituent of a lower alkynyl group, a halogen atom, a lower alkoxy group, or a lower cycloalkyl group. ] A general formula obtained by reacting an aniline conductor represented by the following with phosgene: [wherein, R1, X and Y have the same meanings as above. ] A phenyl isocyanate derivative represented by the general formula [wherein 2 represents an oxygen atom or a sulfur atom]. Rx HaC+ -CI+(7) 7 Ru4 Ru group, (E
a -Ca (1) Fluke=LeJi, CaNO3
an alkynyl group, a lower cycloalkyl group, a lower haloalkenyl group, a lower haloalkynyl group, or a halogen atom, a cyano group, a lower alkoxy group, a lower alkenyloxy group, a lower haloalkoxy group, a phenoxy group,
aEil represents a lower alkyl group substituted with at least one atom or substituent among aralkyloxy group and lower cycloalkyl group. ] General formula characterized by reacting with the alcohol derivative or thioalcohol derivative shown in Q [wherein, X, Y, Rt, loss and 2 have the same meanings as above. However, when X and Y are both bromine groups and the button is a methyl group, and G2 is Kyoko Shunsu, Rt is not a propargyl group, and also, when X and Y are simultaneously a methkin group and R1 is a methyl group, , when G2 is an oxygen atom, Rt is not an ethyl group, when X and Y are both ethoxy groups and R1 is an ethyl group, and when G2 is an @ atom, a is not an ethyl group. ] A method for producing an N-phenylcarbamate compound represented by the following. (1B) General formula [wherein, A lower alkyl group substituted with at least one atom or substituent in the cyano group, or 100Nfi) La (where Rm is a lower alkyl group or a lower alkenyl group) , represents a lower alkyl group or a lower haloalkyl group.R4,
R5 are the same or different and represent a lower alkyl group. n represents 2.8 or 4. a- represents either a hydrogen atom or a lower alkyl group. ). 2 indicates sI hydrogen atom indicates sulfur accompaniment. fLt is a lower alkyl crystal, a lower alkenyl group, a lower alkynyl group, or at least 61 of 710 genomic atoms, a lower alkokino group or a lower cycloalkyl group (
Indicates a lower alkyl group substituted with an atom or substituent of II, chest is Ut, cs is alkyl, C$ is alkenyl, xi is alkynyl 4, lower cycloalkyl 1, lower haloalkynyl group, Any @-class haloalkynyl group, or at least one of an rXX rosin group, a cyano group, a lower alkoxy group, a lower alkenyloxy group, a lower '10 alkoxy group, a phenoxy group, a lower aralkyloxy group, a lower cycloalkyl group N represented by (indicates a lower alkyl group substituted with a child or substituent)
- General formula characterized by reacting a phenyl carbamate compound with hydroxylamine or lower alkoxyamine [wherein, X, R1, and 2 have the same meanings as above. Yl represents hydroxyiminomethyl Ii or a lower alkoxyiminomethyl group.] A method for producing an N-7-enylcarbamate compound represented by the following. (4) General formula [wherein, , a lower alkyl group substituted with at least one atom or substituent among a halogen atom, a hydroxyl group, or a cyano group, or a substituent represented by the following general formula? −
CHlORs. R4 −C0U”a * −CH(o IL, e LHN
, o〉(CHrin. -CORg, -CH=N-ORg, -cO-N
H-Rg (wherein, Rs represents a lower alkyl group, lower alkenyl group, lt-class alkynyl group, 11E-class haloalkyl group, R4 and Rg are the same or different and represent a lower alkyl group. n is 2.8 or 4)凰 represents either a hydrogen atom or a lower alkyl group). 2 represents an oxygen atom or a sulfur atom. R1 represents a lower alkyl group, a lower alkenyl group, a lower alkynyl group, or a lower alkyl group substituted with at least one atom or substituent among a halogen atom, a lower alkoxy group, or a lower cycloalkyl group. . Rs.
is an alkyl group from Ct to C, an alkenyl group from Cm to C8, an alkynyl group from C to C$, a lower cycloalkyl group,
At least one of a lower haloalkenyl group, a lower haloalkynyl group, a halogen atom, a cyano group, a lower alkoxy group, a lower alkenyloxy group, a lower haloalkoxy group, a phenoxy group, an aa aralkyloxy group, a lower cycloalkyl group Indicates a lower alkyl group substituted with one atom or substituent. ] An agricultural and horticultural fungicide characterized by containing an N-phenylcarbamate compound represented by the following as an active ingredient. 06) General formula [wherein X and Y are the same or different, and are any of a halogen atom, a lower alkyl group, a lower alkynyl group, a lower cyanoalkenyl group, a lower alkyl group, a lower alkoxy group, a cyano group, or , a lower alkyl substituted with at least one atom or substituent among a halogen atom, a hydroxyl group, or a cyano group, or a substituted compound represented by the following general formula -CH
! ORI. -COIL・, -CH=N-01L@, -CO-N
H-Ra (where, jLs represents a lower alkyl group, lower alkenyl group, lower alkynyl group, or lower haloalkyl group; jLs and Rg are the same or different and represent a lower alkyl group; n is 2.1 or 4; 1- represents either a hydrogen atom or lower alkyl 1). Zlt@I! Indicates an atom or a sulfur atom. R1 is lower alkyl 1, a lower alkenyl group, a lower alkynyl group, or at least 1III of a halogen group, a lower alkoxy group, or a lower cycloalkyl group
represents a lower alkyl group substituted with an atom or substituent. An alkyl group of 01 to C-, an alkenyl group of Cm to C8, an alkynyl group of Us to C Hatake, a lower cycloalkyl group, a lower haloalkenyl group, a lower haloalkynyl group, or a halogen atom, a cyano group , lower alkoxy group, lower alkenyloxy group, lower haloalkoxy group,
phenoxy m, a low m aralkyloxy group, a lower cycloalkyl group, which represents a lower alkyl group substituted with at least one atom or substituent. The agent for controlling cocoons resistant to a dizimidazole/thiophanate fungicide or a cyclic imide fungicide resistant cocoon according to claim H, characterized in that: General formula [wherein, X and Y are the same or different, and are either a halogen atom, a lower alkyl group, a lower alkenyl group, a lower alkoxy group, or a cyano group, or a halogen atom, a hydroxyl group, or a cyano group. A lower alkyl group substituted with at least an atom of ta or a substituent, or a substituent H-CHmORm represented by the following general formula. 70jLa 7U\ -COORm, -CH\ORi"kL\o, (cm dew) 8--CORg, -Ckl=N-01Ls,
-CONHRs (wherein, Rs represents a lower alkyl group, lower alkenyl group, lower alkynyl 1, or lower haloalkyl group; R4 and Rs are the same or different and represent a lower alkyl group; n represents 2, 8, or 4) , intuition represents either a hydrogen atom or a lower alkyl group). The group represents a lower alkyl group, a lower alkenyl group, a lower alkynyl group, or a lower alkyl group substituted with at least one atom or substituent 1 among a halogen atom, a lower alkoxy group, or a lower cycloalkyl group. R14iC1-Cm alkyl group, Os-Cs alkenyl group, Cm-CI alkynyl group, lower cycloalkyl group, lower haloalkenyl group, lower haloalkynyl group, or halogen atom, cyano group, lower alkoxy group , lower alkyl group substituted with at least one atom or substituent among lower alkenyloxy group, lower haloalkoxy group, phenoxy group, lower aralkyloxy group, and lower cycloalkyl group, N-
An agricultural and horticultural cocoonicidal composition characterized by containing as active ingredients one or more types of phenyl carbamate type compounds and one or more types of benzimidazole/thiophanate type fungicides. (!7) General formula [wherein, a lower alkyl group substituted with a group, or a substituted -CO- represented by the following general formula
Nti-ILs (However, 8 units are lower alkyl groups, lower alkenyl groups,
R4 represents a lower alkynyl group or a lower haloalkyl group
, Ri are the same or different and represent a lower alkyl group, n
indicates 2.8 or 4. IL@ represents either a hydrogen atom or a lower alkyl group. ) is shown. 2 represents an oxygen atom or a sulfur atom. 11LI is a lower alkyl group, a lower alkenyl group, a lower alkynyl group, or 1. 10 Indicates a lower alkyl group substituted with at least one atom or substituent of a Ken atom, a lower alkoxy group, or a lower cycloalkyl group. R2 is any one of an 01-C8 alkyl group, a C1-centered C8 alkenyl group, a Ca-Cs alkynyl group, a lower cycloalkyl group, a lower haloalkenyl group, a lower haloalkynyl group, or a halogen atom, a cyano group, or a lower It represents a lower alkyl group substituted with at least one atom or substituent among an alkoxy group, a lower alkenyloxy group, a lower haloalcoquine group, a phenoxy group, a lower aralkyloxy group, and a lower cycloalkyl group. ]
- A cocoonicidal composition for farm smoke, comprising as active ingredients one or more phenyl carbamate compounds and one or more cyclic imide fungicides.