JPS58192859A - 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 is halogen or methyl; Y is O or S; R<1> is difluoromethyl or 2,2,2-trifluoroethyl; R<2> is 3-8C alkyl, 3-8C alkenyl or phenyl, etc.). EXAMPLE:1-Ethyl-2-propynyl N-(3-chloro-4-difluoromethoxyphenyl)carbamate. USE:An agricultural and horticultural germicide and a controlling agent against drug-resistant germs capable of exhibiting improved effects on the control of blights, e.g. Piricularia oryzae, of rice plants and not only the preventing effects but also the remedial effects. PROCESS:An aniline derivative of formula II is reacted with a chloroformic ester of formula III in a solvent, e.g. benzene, in the presence of a dehydrochlorinating agent, agent e.g. pyridine, to give the compound of formula I in high yield. The reaction is carried out if necessary under cooling or heating at 0-150 deg.C and completed instantaneously-in 10hr.

Description

[Detailed Description of the Invention] 4: Invented, general formula [1] [In the formula, XFi halogen atom or methyl group] is J, and Y is #l! R1 represents a difluoromethyl group or -0-, a trifluoroethyl group, R14 represents a C8-08 furkyl group, a 03-08 alkenyl group, a 03-08 flukynyl group, a 04-C6 Cyclofurkyl group, monosubstituted or unsubstituted phenyl group, substituted or unsubstituted 7-ralkyl group, or halogen atom, C-04
Flukoxy group, nitro group or #'io, ~C5req
Substituted with an alkyl group 90, ~O, alkyl4. o3~
0. Alkenyl group 4 L < Fio3-C4 alkynyl group. ] The N-7 carbamate type compound, its production method, and its inclusion as an active ingredient are the main features of this compound.

Inside Ichiyabu Shiki [I]! The halogen atom represented by is fluorine, chlorine, bromine, i-do atom, etc., and the 03-C8 furkyl group represented by HIA is n.
-propyl, inpropyl.

n-butyl, s@butyl isobutyl, tart -
Butyl, n-pentyl, /-methylbutyl, /-ethylpropyl, /,-1-dimethylbutyl.

Tip 2-dimethylpropyl, n-hexyl, /-methylpentyl, /13-dimethylbutyl, /-ethyl-/
-Methylpropyl, /-methylhexyl, /-methylhebutyl groups, etc., as the 03-Cb alkenyl group, 7
Lyle, -1-butenyl, Jr-butenyl, /-methyl-1-probenyl, comethyl-2-propenyl, /-methyl-3-butenyl, J-methyl-1-butenyl, /-
Ethyl--brobenyl, /-proby--probenyl%/-butyl--probenyl, /-benzene--bropenyl group, etc., but as the 03-C8 alkynyl group, purpargyl, -1-butynyl, 3 -butynyl, /-methylpropynyl, /l/-dimethylpropynyl, /-ethylpropynyl, /-propylpropynyl, /-butylpropynyl, /-bentylbuqvinyl group, etc., 04~
Examples of the C6 leqa9kyl group include SchiffΩbutyl, cyclopentyl, and cyclohexyl groups, and examples of the substituted or unsubstituted phenyl group.

Phenyl, co-methylphenyl, J-methylphenyl groups, etc., 111-substituted f or unsubstituted 7-ralkyl groups, Hauhensyl, -1-chlorobenzyl.

J-'70 lobenzyl, dark chlorobenzyl, 2-fluorobenzyl, 3-fluoropendino 1°g fluorobenzyl, copromobenzyl.

3-bromobenzyl 1.2-methylpendino, 3-methylpenzyl, 41-methylbenzyl, -1-methoxypenzyl, 3-methoxybenzyl, q-methoxylebenzyl, -1-trifluoromethylbenzyl, 3-trifluoro Methylbenzyl.

Dar trifluoromethylbenzyl, t@rt -butylbenzyl, 2,3-dichlorobenzyl, λ, <<-
dichlorobenzyl, co,j-dichlorobenzyl, 2.6
- dichlorobenzyl, j, goo dichloro q benzyl, j,
! -dichlorobenzyl, 2,3-dimethylbenzyl, -
1q-dimethylbenzyl, -0S-dimethylbenzyl,
-26-dimethylbenzyl S3. Gudimethi J lebenzyl, 3,5-dimethylbenzyl, α-methylbesidyl,
α-Ethylbenzyl, α-ethynylbenzyl, phenethyl, dark q-phenethyl/a-phenylbenzyl, furfuryl, cinnamyl group, etc. have 0 to halogen atom, C□. Flukoxy group, nitro group or Fi03~C, substituted with dichlorofurkyl group 60~C4furkyl group, C3
~0. As the alkenyl group or Fi, 03-C4 alkynyl group, -1fluoroethyl, -chloroethyl,
Copromoethyl 1. ? , 2.2-triclo p-ethyl,
3-chloropropyl, /-fluoromethyl-1-fluoroethyl, /-chloromethyl-1-chloroethyl, /-
Promomethyl--promoethyl, -1J-dichloro-qpropyl% goucloro-butenyl, goubromo-butenyl, q-chloro-1-butynyl, q-promo-1-butynyl, /-methyl--methoxyethyl.

l-methyl-ethoxyethyl, /-methyl-butoxyethyl, /-methoxymethyl-chloroethyl, V-methoxy-butenyl, q-methoxy-11butynyl, -12-trobutyl, -1-methyl-conitrhopropyl, Cyclopropylmethyl, /-cyclopropylethyl, /-cyclobutylethyl, /-cyclobentylethyl, /-cyclopvirbuqpyl, etc. can be used.

The N-7-enyl carbamate compound represented by the general formula [1] is, for example, the rice potato tlIIIi! I(P
yricularia oryma*), downy mildew of yellow cucumber 1 (Pa@udoperonoapora c
ubanlsig), Potato Phytophthora blight (Phyt.
tophthora 1nfestans), groundnut brown spot @ (Cercospora arac
hldicolm), apple scab fungus (Vent
uria ins@qualig), Rice sheath blight fungus (Rhigoctonia 5olani), Pythium aphanida seedling blight (Pythium aphanida)
rmtum) % radish yellowing fungus (F'uaar
ium oxysporum L sp, r@pha
The 1% image indicates a high effectiveness in controlling ni)%.

Many synthetic organic compounds with antibacterial properties have been discovered and developed as agricultural fungicides, making a great contribution to the stable supply of agricultural products.

However, it is also true that there are many problems that need to be improved, and such problems can be classified as F! 7
1+ Insufficient removal effect, occurrence of drug-resistant bacteria, environmental pollution, etc.

The present inventors took the above points into consideration, and as a result of repeated studies on various synthetic organic compounds, they discovered that the above-mentioned N-7-enylcarbamate-based compound exhibits an excellent effect on disease control. In particular, it has not only a preventive effect but also a therapeutic effect.
When actually used in the field, it shows a stable anti-# effect ◇As a result of further studies on these N-7 carbamate compounds, some of them are benomyl[methyl/-(butylcarbamoyl)]. Penzimidazole--ylcarbamate], Fuberidazole CJ-
(2-furyl)benzimidazole], thiabendazole CJ-(+-thiazolyl)benzimidazole], carpendazim [methylbenzimidazol-1-yl
h-bamate], thiophanate methyl [/, -bis(J-methoxycarbonyl--thioureido)benzene], thiophanate [/*-2-bis(3-ethoxycarbonyl-J-thioureido)benzene], etc. Drug-resistant bacteria showing resistance to benzimidazole/thiophanate-based pesticides, procymidone (h-(J, −(
J',j'-dichlorophenyl)-/-isopropylcarba-tatylimidazolidine-, Tei-Sion], vinclozolin C3-(3',s'-dichlorophenyl)-j
-Methyl-j-vinyloxazolidine-.

Goudion], Serinal [ethyl (R,8)-J-(
J,j-dichlorophenyl)-S-methyl-,4I-
We have additionally discovered that the compound of the present invention exhibits a strong killing effect selectively against drug-resistant bacteria that are resistant to cyclic imide fungicides such as dioxazolidine-j-carboxylate. Therefore, the compound of the present invention has drug-resistant properties. It is also extremely useful as a fungicidal agent.

In actual cases where drug-resistant bacteria usually occur, there are cases where most of the bacteria are drug-resistant, and cases where there is a mixture of resistant and susceptible bacteria. Either of these may be used alone, or may be used in combination with benzimidazole/thiophanate-based pesticides or cyclic imide-based pesticides, or in combination. -Especially effective against drug-susceptible bacteria. When a single plane is used as a wetting agent, as is clear from Date's test example, K, the above-mentioned N
- A significantly high disease control effect was found when used in combination with 7 or more types of phenyl carbamate fungicides and 7 or more types of benzimidazole/thiophanate fungicides or Vim-like imide fecicides. ◎ Therefore, the agricultural and horticultural soda-killing composition according to the present invention has high practical value as a fungicide that exhibits an excellent pesticidal effect in any field. - The compound C1) of the present invention is a new compound and , for example, can be produced by the following method @ (a) - Formula [1] [wherein X and R1 have the same meaning as above]
] Aniline derivatives represented by the general formula [-]R”y8a
t (1) [wherein, Y and Bg
has the same meaning as above. ] A manufacturing method of reacting with a chloroformic acid ester represented by

This reaction is carried out in an organic solvent such as benzene, toluene, xylene, diethyl ether, tetrahydrofuran, dioxane, chloroform, carbon tetrachloride, ethyl acetate, pyridine, dimethylform 7t#1, or a mixture thereof; pyridine, triethylamine, Diethyl 7 niline.

One reaction can be carried out in high yield by using a dehydrochlorinating agent such as sodium hydroxide or potassium hydroxide.

The reaction is cooled or heated (0 to 750°C) as necessary.
], it is completed in 7θ hours from # time, and the yield is
You can get what you want.

The 7-nilin cast conductor represented by the general formula [Otori] in manufacturing method (a) is represented by the general formula (IV) [wherein, X and R1 are the same as described above]. It is obtained by the reduction reaction of a nitrobenzene cod conductor, which has a taste.

This nitrobenzene derivative is described, for example, in Document J, Or
g, Cham, , Lj JOO9 (/f4θ) and the method described in JP-A-56-36tI47.

(b) General formula (V)! [In the formula, X and R1 have the same meanings as above.] A phenyl isocyanate derivative represented by
v1] R"YI ((Vl) [In the formula, Y and 2 have the same meanings as -j above] Production method O in which the reaction is performed with an alcohol or thiol represented by Or benzene, toluene.

The reaction can be carried out in an organic solvent such as xylene, diethyl ether, tetrahydrofuran, dioxane, dimethylformamide, dichloroform, or carbon tetrachloride without a catalyst or with a catalyst such as pyridine, triethylamine, or diethyl chloride. By cooling or heating (o-5oQ) depending on the temperature, the reaction is completed in 70 hours from time H.

The target product can be obtained in good yield.

The phenyl isocyanate derivative represented by the general formula EV) can be obtained by reacting the aniline conductor represented by the general formula (1) with phosgene. to do O implementation t'//-ethyl J-propynyl N-(3-
Synthesis of chloro-q-difluoromethoxyphenyl) carnocoumate (according to method (a)) j-chloroQ-Q-difluoromethoxyaniline/, 93
11 and diethylaniline i, sy in toluene SOa
Dissolved in / and cooled with water /-ethyl-provinyl
Roformate/, 1 Bftj minutes. The fireflies were stirred for θ hours, placed in ice water, and shaken out with Aete JL. Washed with water and dried with @WX magnesium, the powder was evaporated to obtain an oily substance, qsyt.
Purified by gel column chromatography using a mixture of 7 setsone and /-ethyl-provinyl N
-(J-chloro-+-difluoromethoxyphenol)
Obtained white crystals of 2.76F (yield?
0.9chi〉Melting point 36-3, j'C Elemental analysis value 0 (To) H(Ki M(4) Min (Shi) Calculated value
5/, /I/ J,? ff +, 6/ /
/, b7 (as C engineering 3H1g○tF2N03) real 81
11 f4 J/, 47 y, os y
, ss /i, s3 real mfl J, e-dichlorobenzyl N -(J-chloroda-difluoromethoxyphenyl)carbamate synthesis l1K (method (according to BL) triethylamine/l and co, 4t-dichlorobenzyl alcohol/, lff acetic acid 3-chloro-q-difluoromethoxyphenylisocyanate co, -t was added dropwise to the mixture and stirred for about 6 hours in the 0 room, poured into ice water, and extracted with ether.Washed with water and extracted with ether.
Coarse crystals 3 are obtained by distilling off the ridge bath 1 dried with l&magnesium.
．． Got 5P. This is a mixture of hexane and 7 setone #
It was prepared using silica gel column chromatography using a hood, and was then purified using silica gel column chromatography.
White crystals of difluoromethokyrephenyl) carbamate J, JP were obtained (Ig? rate lθ, 7ch) melting point 11-6
TS℃ Elemental analysis value 0 (a) Group M (support) 02 (calculated value 4j
j, invasion -, JM J, JJ -ru JJ (Cx?x
o”lsνtzNO5) Actual −j value tr5.3
1 2.4b jJJ j4.79 Next, examples of the compounds of the present invention represented by the general formula [1] obtained in the same manner as in Example 2 and 2 are given below. The compounds are not limited to these only. The compound numbers shown here are commonly used in the following formulation examples and test examples.

When actually applying the compound of the present invention obtained in this way, it can be used in pure form without adding other ingredients, or it can be mixed with a carrier to make it easier to use as a fungicide. It can be applied in any of the commonly used forms such as powders, wettable powders, oils, emulsions, gunpowders, granules, fine granules, aerosols, flowables, etc. Also, N according to the present invention can be applied. - When using a mixture of /f11 or more of a phenyl carbamate compound and / or more of the above-mentioned benzimidazole superior thiophanate fungicide] or a beak-shaped imide fungicide, these should be mixed in a weight ratio. / : It can be mixed with a carrier so as to contain a mixed copper content of o, i to IO, and then formulated and applied to the shadow line as described above.

Generally included in the formulation is ri! 8 o-qs, o %, preferably 2.0-0. θ Chi [Including, normal / per Q R ~
The application amount of ioo g is appropriate. Furthermore, the concentration used is o, oos whisper to 0. j- range is desirable, but since these usage amounts and concentrations vary depending on the dosage form, application time, method, location, target disease, target crop, etc., the product number may be increased or decreased without being limited to the above range. Compound 1 listed in Table 1 is shown in A, and the following compounds are shown in A to ■.

Test Example 1 of Phoximide Gougeone-Carpoxylate Rice (variety: Kinki No. 33) was sown in a plastic pot with a rice blast control effect of 90 dWI in a rice cultivation tube. This was grown in a greenhouse, and a water-diluted solution of the test compound in emulsion form was sprayed on the foliage of seedlings at the 311I stage obtained until the droplets sufficiently adhered to the leaf surface. After air-drying the rice blast fungus (P7rioul)
A spore suspension of ar1aorysa.) was inoculated by spraying. After 3 days in a laboratory, RC, and humid conditions, the disease state was observed. The disease severity was calculated by the following method. That is, depending on the degree of disease appearance on the questionnaire, 0, 0.
3 @ / eko, categorized into 41+ exponents and issued by the following formula! f tube was calculated.

(Sickness line) (Sickness state) O fist...os
Bacterial flora or lesions tiI are placed on surface iii in an area less than j of the scooped area on surface #4.

/ @*@*・Kli and lesions t7 less than 1% of the leaf area are observed on the middle leaf surface.

J...Leaf area on axis collection plane SO- less than K11ll1
1il or 1 lesion was observed.

Da・Conflict・・There are more bacteria on the leaf surface than the leaf area
Or lesions are recognized.

Next, the control value was calculated using the following formula.

As a result, as shown in Table 1, the compound of the present invention had a control value of 1; Show (7)

Notes to Table 2 (1) i-Sales MIli agent Plastic pots were filled with sandy loam, and cucumbers (success: Aoyahanshiro) were sown, one seed per pot. This was cultivated in a greenhouse for 9 days to obtain cucumber seedlings with expanded cotyledons. A water-diluted solution of the test compound in the form of an emulsion was sprayed on the foliage of the seedlings so that the 4# solution was sufficiently attached to the seedlings. mulberry'
ffIML dried cucumber and diseased bacteria on young seedlings (P@*udo
A conidial suspension of Peronospora cuben (1 m field) was sprayed with 9A mist. This was placed under a humid column for 3 days, and then exposed to 20°C fluorescent lamp illumination for 3 days to induce disease, and the bowl-shaped spines were observed. The investigation method and calculation of control value will be tested;/
I did the same thing.

As shown in Table 3, the results showed that the compound of the present invention had an excellent pesticidal effect.

Table 1 Animal experiment example 3 Powdery mildew control effect of Kineweed 0 - Wotsume in sandy loam soil and Kineweed (variety: Aikigyushiro) were sown in customer's plastic pots. I sang this in a greenhouse for several days, and obtained a collection of young cucumber seedlings. Apply a water diluted solution of the test compound in emulsion or hydrated form to these young seedlings using a tube to ensure that the liquid acid is sufficiently attached to #(3). The 0 chemical solution J I had hoped for! Cucumber udonko hat with drug resistant or sensitive seedlings after L transfer @ (5
pha@rot-1eeeaful1ginea)
A suspension of conidia was inoculated by spraying. The plants were placed in a greenhouse and cultivated for /θ days to develop the disease, and then the disease state was observed.

Illness! The inspection method and calculation of control value were performed in the same manner as in Test Example.

As a result, as shown in Table 9, the compound of the present invention showed an excellent control effect when inoculated with drug-resistant bacteria, but did not show any control effect when inoculated with drug-susceptible bacteria. On the other hand, none of the commercially available fungicides benomyl, thiophanate methyl, and carpendazim showed any control effect when inoculated with drug-resistant bacteria.
When inoculated with drug-susceptible bacteria, excellent control effects were shown.

Compounds with a similar chemical structure and commercially available herbicides with a similar chemical structure used for comparison did not exhibit #1 Tondo control 57J Vermilion, regardless of which bacteria were inoculated.

Note (1) Compound properties synthesized for comparison - commercially available herbicide SWEP Note (I), BCPC (chlorbufam),
, Experimental Example DA Cucumber gray mold control effect 901 volumes of plastic pots were filled with sandy loam, and cucumbers (variety: Sumo Hanshiro) were sown. Cultivate this at 7i1 temperature for 5 days,
I obtained a cucumber with expanded cotyledons. An emulsion or a water-diluted solution of the test compound for water use was sprayed onto the seedlings until the liquid was sufficiently attached to the leaf surface. Drug-resistant or IIA-susceptible cucumber gray mold fungus (Botr)
ytlm cln@rea) Ill +J+ piece (Nikkatsura jshin) was pasted on the top of the plate and made into an oil. This is 20″
The horse mackerel was kept under humid conditions for 3 days, and the horse mackerel was observed after the onset of disease.

The method for investigating the onset of the disease and the calculation of the control value were completed in the test example / and 1 town strain.

As shown in Table 5, the imported electrolyte of the present invention showed an excellent control effect when exposed to a chemical agent, and on the contrary, commercially available insecticides showed an excellent control effect. i
The agents benomyl and thiophanate methyl have a mulberry effect of 52.
90 Test Example S Is Kikucuri powdery mildew control effect showing excellent control effect when inoculated with Powdery mildew? Fill a θml plastic pot with sandy loam, and add cucumbers (product &=
Sagami Hanpaku) was sown. This was grown in a greenhouse for several days to obtain cucumber seedlings with expanded cotyledons. The seedlings were sprayed with a water-diluted solution of the test compound in the form of an emulsion or a wettable powder until the liquid part fully adhered to the collection surface.
The conidial spores obtained by mixing 1 gln@a) of drug-resistant bacteria and Sensu Hakuzono were cultured. The plants were cultivated in a greenhouse for 10 days to develop the disease, and then the disease state was observed. @ Disease inspection method and calculation of control value were performed in the same manner as in Test Example.

As a result, as shown in Table 6, the scratching force of the N-phenyl carbamate compound according to the present invention and benzimidazole
By applying a mixture of any of the thiophanate-based pesticides, a clearly higher pesticidal effect was achieved than when each agent was applied alone.

Test Example 6 Tomato Gray Mold Control Effect: Sandy loam jujube and tomatoes (variety: Fukuju-go) were sown in plastic pots at θ1 valley. This was cultivated in a greenhouse for q weeks to obtain q leaf stage tomato fungi. The leaves were destroyed in a trench where a water-diluted solution of a wettable powder form of the 5-5 compound was sufficiently applied to the leaf surface. 8 Lμ grade conidia were inoculated by mixing G-G dry scissors, Botrytls clnersa drug needle candy, and burr-receptive powder. This is -θ°C multi-t multi-thread 9
After I had a child under my care, I checked to see if he had developed an illness. The calculation of the origin, the charm method and the pesticidal value is the test result + l / and 16! I did it in memory.

That l? Since then, by using the Nh according to the present invention, as in the 7th and 7th revolutions, it has become clear that compared to the H river, P/l has been solved.

Formulation example/2 parts of powder compound (S;/), 5 parts of clay and 97 tal
If 0 parts are thoroughly mixed as a powder, a powder with a main ingredient content of 2- is obtained.

Formulation example - 30 parts of hydrating compound (2, 2), 0 parts of diatomaceous earth, 0 parts of white carbon, 1 part of wetting agent (lauryl soda) and 7S parts of dispersing agent (calcium lignin sulfonate) If they are thoroughly ground and mixed, an irrigation agent with a base ingredient content of 3θ can be obtained.

Formulation Example 3 0 parts of hydrating agent compound (57) j, J parts of silica clay, 2S parts of wetting agent (calcium alkylbenzenesulfonate) and 2.5 parts of dispersing agent (ligninsulfone-calcium) were thoroughly ground and mixed. In this way, an irrigation agent with a main agent content of Sochi is obtained.

Formulation example 70 parts of emulsion compound (3θ), 0 parts of cyclohexanone, and emulsifier (polyoxyethylene furkyl 7lyl ether)
If 70 parts are mixed, main cutting mixture example j powder agent compound (27) / part, compound (g)) / s1 clay 5
Part g and 970 parts of tal were thoroughly ground and mixed to obtain a powder having a main ingredient content of d and 2S.

Formulation Example 6 Wettable powder compound vJ (7A), 20 parts, compound powder 30 parts, powdered SilI sugar '10@, white carbon J part, wet button agent (sodium lauryl silicate) 3 parts, and fraction A11 (lignin Calcium sulfonate), #tj3 can be thoroughly ground and mixed to produce an irrigation agent with a base ingredient content of j0. .

Donation ψ17 Hydrating agent compound * (///) 30 parts, Compound (F') -0 parts, Silica clay 93 ml, Wetting agent (calcium flukylbenzenesulfonate) 2js and Dispersing agent (calcium lignin sulfonate) ), if the lj part is well ground and mixed, use a cap containing royal agent j0
Obtain Chi's irrigation agent.

In the formulation example, hydrating agent compound (Ri J) jθ parts, compound (G) j, 5 parts,
Parts of diatomaceous earth, 3.5 parts of a wetting agent (calcium alkylbenzenesulfonate), and 3.5 parts of a dispersing agent (calcium ligninsulfonate) J and jfhl are thoroughly ground and mixed to obtain an irrigation agent with a base agent content of 7j%.

Procedural Amendment (Voluntary) February 1980 Double Date n-Dear Director-General of the Agency 1 $ Item υ Indication Showa No. 157 Year Patent Axle No. 76749 2 Kuraaki υ Name 8J, 117x Nyl Force - Bamate Compound, Its manufacturing method and its active ingredient as a pesticide for agricultural use 3 Supplement 1 ■Relationship with the case study Patent applicant 5-15 Kitahama, Higashi-ku, Osaka (Representative of 209i Kayu Kagaku Ogyo Co., Ltd.) Each Kamigata Takeshi 4 agent

Claims (1)

[Scope of Claims] (c) General formula [wherein, Show HR
is 0. ~08 alkyl group, O5~08 alkenyl group, 0
3-C8 alkynyl group, 04-06 cycloalkyl group. 11 substituted or unsubstituted phenyl group 1M substituted or unsubstituted 11
Fusuma aralkyl group or halogen atom, C~0. Flukoxy group, nitro group or tj: (represents 0□-0.furkyl group substituted with 3-05 dichlorofurkyl group, 03-0.alkenyl group or 03-C or flukynyl group).
N-phenyl carbamate compound represented by 0 rho general formula [wherein, X represents a halogen atom or a methyl group, R1
has 11 difluoromethi groups. Aniline derivatives represented by the general formula % [wherein, YF'i oxygen or Fi sulfur atom, R2 digit C3-C8 alkyl group, C3-C8 alkenyl Base, 03
~08 alkynyl group, 04-C6 lecroalkyl group, 1
Mono-substituted or Vi-unsubstituted phenyl group. Substituted or unsubstituted aralkyl group or C-0. Flukoxy group, nitro group, or #i03
~05 Cycloalkyl group-substituted O-C, alkyl group, 03-04 fluorenyl i or 03-o4 alkynyl group represented by t] General A method for producing an N-7-enyl carbamate compound represented by the formula: [wherein X, Y, R1 and R11 have the same meanings as above]. [In the formula, X represents a halogen atom or a methyl group, and RI
Fi represents a difluoromethyl group or -1J, J-1, a difluoroethoxyle group. ] 114 phenyl isocyanates represented by the general formula [where Y represents oxygen or a sulfur atom, and R2 represents 03-
08 furkyl group, 03-o8 alkenyl group, 03-C8
Furkynyl group, 04-06 cyclofurkyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted 7-ralkyl group or halogen atom, C□-0. C-0. substituted with a flukoxy group, a nitro group, or a 03-06 cyclofurkyl group. Furkyl group, 03-0. Flukenyl group or 03-0. The alcohol size represented by O] representing a flukynyl group is a general formula [where X, Y, R1 O! HRg has the same meaning as described above.] Method for producing N-7-enylcarbamate compounds represented by ◎ [In the formula, X represents a halogen atom or a methyl group,
i indicates bulk or sulfur atom. R1 represents a difluoromethyl group or FiJ, J, J-trifluoroethyl group,
, 04-06 cycloalkyl 4° Substituted or unsubstituted phenyl group, substituted or #'i unsubstituted aralkyl group or halogen atom, 0□-C4 alkoxyl group, nitro group or C3-C, cycloalkyl group substituted f5c Yu~
C, furkyl group, 03-01 alkenyl group or Fi
03-C4 alkynyl group. ] Expressed with! Shiru N-
IIkrill artistic fungicide containing the 7th grade nyl carbamate compound as an active ingredient
;j Indicates oxygen or sulfur atom. R1 represents a difluoromethyl group or a mono, co, --trifluoroethyl group, R"Fi03~C. Alkyl group, 03~08 alkenyl group, 03~08 flukynyl a, O, ~O, cycloalkyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted III!7 ralkyl group or halogen atom, C, -04 flukoxy group, nitro J14.L<Fi03~C5C~C,furkyl group substituted with dichlorofurkyl group%03 7 or more types of N-7 enylca)-bamate compounds represented by ~0.0.0.flukenyl group or 03-04 alkyl group) and benzimidazole/thiophanate type pesticides or Viyang imide type pesticides. The special feature is that it contains 7 or more of the above-mentioned ingredients as active ingredients.