WO2011108396A1 - Oxime ether derivatives or salts thereof, and germicides for agricultural or horticultural use - Google Patents
Oxime ether derivatives or salts thereof, and germicides for agricultural or horticultural use Download PDFInfo
- Publication number
- WO2011108396A1 WO2011108396A1 PCT/JP2011/053807 JP2011053807W WO2011108396A1 WO 2011108396 A1 WO2011108396 A1 WO 2011108396A1 JP 2011053807 W JP2011053807 W JP 2011053807W WO 2011108396 A1 WO2011108396 A1 WO 2011108396A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- unsubstituted
- substituted
- alkyl
- alkyl group
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
Definitions
- the present invention relates to an oxime ether derivative or a salt thereof, and an agricultural and horticultural fungicide. More specifically, the present invention relates to a novel oxime ether derivative or a salt thereof, and an agricultural and horticultural fungicide containing as an active ingredient at least one selected from the oxime ether derivative or a salt thereof.
- control agents In the cultivation of agricultural and horticultural crops, various control agents are used against crop diseases. However, many of these control agents have insufficient control efficacy, their use is limited by the emergence of drug-resistant pathogens, cause phytotoxicity and pollution to plants, or are toxic to human fish and have an impact on the environment. It is difficult to say that it is a satisfactory control agent because of the problems such as large For this reason, there is a strong demand for the emergence of a control agent that has few such problems, has a high control effect, and can be used safely.
- Patent Document 1 oxyamine derivatives
- Patent Document 2 oxime derivatives
- Patent Document 3 oxime ether derivatives
- Patent Documents 1 to 3 The oxyamine derivatives, oxime derivatives, or oxime ether derivatives or salts thereof described in Patent Documents 1 to 3 can be easily synthesized industrially, have a high control effect, and can be used as safe control agents. It was. However, the compounds described in Patent Documents 1 to 3 require a relatively large application amount (g / ha) of the compound required for use as a control agent depending on the target disease. Due to the low permeability of the compound to crops, there was a case where a sufficient control effect was not obtained in practical use. In view of such circumstances, the present invention can be easily manufactured industrially, has a large control effect even at a low concentration and a small application amount, and has high penetrability and residual effect on many agricultural and horticultural crops.
- oxime ether derivative having a pyrazole ring group represented by the formula (I) or a salt thereof was obtained.
- These oxime ether derivatives or salts thereof can be easily produced industrially, and agricultural and horticultural fungicides containing at least one selected from these compounds as an active ingredient have a low concentration and an application rate.
- the control effect is large, the penetration and retentivity to many agricultural and horticultural crops is high, and the control effect against diseases is certain, and there is little phytotoxicity and pollution to plants, We found that it has excellent safety because it has little impact on the environment.
- the present invention has been completed by further studies based on these findings.
- the present invention includes the following aspects.
- X represents a halogen atom, a C1-8 alkyl group, a C1-8 alkoxy group, a C1-8 haloalkyl group, or a C1-8 haloalkoxy group.
- n represents the number of substitutions of X and is an integer from 0 to 4. When n is 2 or more, Xs may be the same or different.
- R 1 and R 2 each independently represents a hydrogen atom, a halogen atom, a C1-8 alkyl group, a C1-8 haloalkyl group, or an unsubstituted or substituted C3-8 cycloalkyl group. R 1 and R 2 may be bonded together to form a ring.
- R 1 and R 2 may be the same or different.
- R 3 is a hydrogen atom, a C1-8 alkyl group, a C2-8 alkenyl group, a C2-8 alkynyl group, a C1-8 haloalkyl group, a C2-8 haloalkenyl group, a C2-8 haloalkynyl group, or an unsubstituted or Represents a C3-8 cycloalkyl group having a substituent.
- R 4 represents a hydrogen atom, a C1-8 alkyl group, an unsubstituted or substituted C3-8 cycloalkyl group, a C2-8 alkenyl group, a C2-8 alkynyl group, a C1-8 haloalkyl group, a C2-8 halo. It represents an alkenyl group or a C2-8 haloalkynyl group.
- R 5 is a hydrogen atom, C1-8 alkyl group, acyl group, formyl group, C1-8 alkoxy C1-8 alkyl group, C2-8 acyloxy C1-8 alkyl group, C1-8 alkoxycarbonyl group, C1-8 alkyl
- a sulfonyl group or an unsubstituted or substituted phenylsulfonyl group is represented.
- Y represents an oxygen atom or a sulfur atom.
- Z represents a single bond, an oxygen atom, a sulfur atom, or a group represented by NR 6 .
- R 6 represents a hydrogen atom or a C1-8 alkyl group.
- Q represents an unsubstituted or substituted pyrazole ring group.
- X is a C1-8 alkyl group
- R 1 , R 2 , R 3 , R 4 and R 5 are each independently a hydrogen atom or a C1-8 alkyl group
- Y and Z are oxygen atoms
- Q is unsubstituted or substituted 1H-pyrazol-3-yl group, unsubstituted or substituted 2H-pyrazol-3-yl group, or unsubstituted or substituted 1H-pyrazol-
- m is 1, and n is 0 to 1.
- the compound of the present invention can be easily produced industrially, has a large control effect at a small application rate for many agricultural and horticultural crops, and has an excellent osmotic migration and residual effect, and therefore has a control effect against diseases. It is a novel compound useful as an active ingredient of an agricultural and horticultural fungicide that is reliable and can be used safely.
- the fungicide of the present invention has an excellent control effect even when the concentration of the compound of the present invention is low and the application amount is small, does not cause phytotoxicity or contamination on the plant body, and is toxic to human and livestock and has an impact on the environment. It is a drug with excellent safety.
- Oxime ether derivative or salt thereof The compound of the present invention is an oxime ether derivative represented by the formula (I) or a salt thereof.
- X represents a halogen atom, a C1-8 alkyl group, a C1-8 alkoxy group, a C1-8 haloalkyl group, or a C1-8 haloalkoxy group.
- n represents the number of substitutions of X and is an integer of 0 to 4, preferably an integer of 0 to 2, more preferably 1. When n is 2 or more, Xs may be the same or different.
- the halogen atom examples include a fluorine atom, a chlorine atom, and a bromine atom.
- the C1-8 alkyl group may be linear or branched. For example, methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, s-butyl group, t-butyl group, n-pentyl group, n-hexyl group, n- A heptyl group, n-octyl group, etc. are mentioned.
- the C1-8 alkoxy group may be linear or branched.
- the C1-8 haloalkyl group is not particularly limited as long as it is an alkyl group substituted with a halogen atom.
- fluoromethyl group chloromethyl group, bromomethyl group, difluoromethyl group, dichloromethyl group, dibromomethyl group, trifluoromethyl group, trichloromethyl group, tribromomethyl group, 2,2,2-trifluoroethyl group
- Examples include 2,2,2-trichloroethyl group, pentafluoroethyl group and the like.
- the C1-8 haloalkoxy group is not particularly limited as long as it is an alkoxy group substituted with a halogen atom.
- chloromethoxy group for example, chloromethoxy group, dichloromethoxy group, trichloromethoxy group, trifluoromethoxy group, 1-fluoroethoxy group, 1,1-difluoroethoxy group, 2,2,2-trifluoroethoxy group, pentafluoroethoxy group, etc.
- X is preferably a C1-8 alkyl group.
- R 1 and R 2 each independently represents a hydrogen atom, a halogen atom, a C1-8 alkyl group, a C1-8 haloalkyl group, or an unsubstituted or substituted C3-8 cycloalkyl group.
- m represents the number of repeating units in parentheses and is an integer from 0 to 8, preferably an integer from 0 to 3, more preferably an integer from 0 to 1. When m is 2 or more, R 1 and R 2 may be the same or different.
- the halogen atom, C1-8 alkyl group, and C1-8 haloalkyl group in R 1 and R 2 are the same as those described as the halogen atom, C1-8 alkyl group, and C1-8 haloalkyl group in X above. Is mentioned.
- Examples of the unsubstituted C3-8 cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group.
- Substituents for C3-8 cycloalkyl groups include: halogen atoms such as fluorine, chlorine and bromine; C1-6 alkyl groups such as methyl and ethyl groups; C1-6 alkoxy groups such as methoxy and ethoxy groups Nitro group; cyano group; and the like.
- R 1 and R 2 may be bonded together to form a ring.
- the ring may contain a hetero atom such as an oxygen atom, a sulfur atom or a nitrogen atom. Examples of such a ring include a cyclopropane ring, a cyclopentane ring, a cyclohexane ring, and a tetrahydropyran ring.
- R 3 is a hydrogen atom, a C1-8 alkyl group, a C2-8 alkenyl group, a C2-8 alkynyl group, a C1-8 haloalkyl group, a C2-8 haloalkenyl group, a C2-8 haloalkynyl group, or an unsubstituted or Represents a C3-8 cycloalkyl group having a substituent.
- C1 ⁇ 8 alkyl group for R 3 examples of C3 ⁇ 8 cycloalkyl group having C1 ⁇ 8 haloalkyl group, and an unsubstituted or substituted group, such as in the X or R 1, C1 ⁇ 8 alkyl, C1 ⁇ 8 Examples include the same haloalkyl groups and those described as unsubstituted or substituted C3-8 cycloalkyl groups.
- C2-8 alkenyl groups include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl-2 -Propenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group, 2-methyl-2-butenyl group, 1-hexenyl group, 2-hexenyl group Group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group and the like.
- C2-8 alkynyl groups include ethynyl, 1-propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 2-methyl-3-butynyl Group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 2-methyl-3-pentynyl group, 1-hexynyl group, 1,1-dimethyl Examples include a -2-butynyl group.
- the C2-8 haloalkenyl group includes a 3-chloro-2-propenyl group, a 4-chloro-2-butenyl group, a 4,4-dichloro-3-butenyl group, a 4,4-difluoro-3-butenyl group, 3 , 3-dichloro-2-propenyl group and the like.
- C2-8 haloalkynyl groups include 3-chloro-1-propynyl group, 3-chloro-1-butynyl group, 3-bromo-1-butynyl group, 3-bromo-2-propynyl group, 3-iodo-2 -Propynyl group and the like.
- R 4 represents a hydrogen atom, a C1-8 alkyl group, an unsubstituted or substituted C3-8 cycloalkyl group, a C2-8 alkenyl group, a C2-8 alkynyl group, a C1-8 haloalkyl group, a C2-8 halo. It represents an alkenyl group or a C2-8 haloalkynyl group.
- Examples of the C1-8 alkyl group in R 4 include the same as those described as the C1-8 alkyl group in X.
- Examples of the unsubstituted or substituted C3-8 cycloalkyl group in R 4 include the same as those described as the unsubstituted or substituted C3-8 cycloalkyl group in R 1 and the like. It is done.
- the C2-8 alkenyl group, C2-8 alkynyl group, C1-8 haloalkyl group, C2-8 haloalkenyl group, and C2-8 haloalkynyl group include the C2-8 alkenyl group in R 3 , Examples thereof include those described as C2-8 alkynyl groups, C1-8 haloalkyl groups, C2-8 haloalkenyl groups, and C2-8 haloalkynyl groups.
- R 5 is a hydrogen atom, C1-8 alkyl group, acyl group, formyl group, C1-8 alkoxy C1-8 alkyl group, C2-8 acyloxy C1-8 alkyl group, C1-8 alkoxycarbonyl group, C1-8 alkyl
- a sulfonyl group or an unsubstituted or substituted phenylsulfonyl group is represented.
- Examples of the C1-8 alkyl group for R 5 include the same as those described as the C1-8 alkyl group for X.
- acyl group examples include an acetyl group, a propionyl group, a pivaloyl group, a trifluoroacetyl group, a trichloroacetyl group, a benzoyl group, a 4-methylbenzoyl group, and a 2-chlorobenzoyl group.
- C1-8 alkoxy C1-8 alkyl group includes methoxymethyl group, ethoxymethyl group, i-propoxymethyl group, 1-methoxyethyl group, 2-methoxyethyl group, 1-ethoxyethyl group, 2-ethoxyethyl group, Examples include 1-methoxy-n-propyl group, 2-methoxy-n-propyl group, 3-methoxy-n-propyl group and the like.
- Examples of the C2-8 acyloxy C1-8 alkyl group include an acetoxymethyl group, an acetoxyethyl group, a propenyloxymethyl group, a pivaloyloxymethyl group, a 1-acetoxyethyl group, a 2-acetoxyethyl group, and a 1-acetoxy-n. -Propyl group and the like.
- Examples of the C1-8 alkoxycarbonyl group include methoxycarbonyl group, ethoxycarbonyl group, isopropoxycarbonyl group, n-butoxycarbonyl group, t-butoxycarbonyl group and the like.
- Examples of the C1-8 alkylsulfonyl group include a methylsulfonyl group, an ethylsulfonyl group, an n-propylsulfonyl group, and an i-propylsulfonyl group.
- Examples of the unsubstituted or substituted phenylsulfonyl group include a phenylsulfonyl group, a 4-methylphenylsulfonyl group, a 2-chlorophenylsulfonyl group, and a 2,4-dimethylphenylsulfonyl group.
- R 1 , R 2 , R 3 , R 4 and R 5 are each independently a hydrogen atom or a C1-8 alkyl group.
- Y represents an oxygen atom or a sulfur atom.
- Z represents a single bond, an oxygen atom, a sulfur atom, or a group represented by NR 6 .
- R 6 represents a hydrogen atom or a C1-8 alkyl group. Examples of the C1-8 alkyl group for R 6 include the same as those described as the C1-8 alkyl group for X.
- Y and Z are preferably oxygen atoms.
- [Q] Q represents an unsubstituted or substituted pyrazole ring group.
- the bonding position of the pyrazole ring group and the carbon having R 1 and R 2 is not particularly limited.
- Q is an unsubstituted or substituted 1H-pyrazol-3-yl group, an unsubstituted or substituted 2H-pyrazol-3-yl group, or an unsubstituted or substituted 1H-pyrazol- A 4-yl group is preferred.
- Examples of the substituent of the pyrazole ring group include a halogen atom, an unsubstituted or substituted C1-8 alkyl group, an unsubstituted or substituted C2-8 alkenyl group, an unsubstituted or substituted C2 -8 alkynyl group, unsubstituted or substituted C1-8 alkoxy group, unsubstituted or substituted C1-8 alkylthio group, unsubstituted or substituted C1-8 alkylsulfonyl group, or unsubstituted Examples thereof include a substituted or substituted C1-8 alkylsulfonyloxy group.
- halogen atom, C1-8 alkyl group, and C1-8 alkoxy group in the substituent of the pyrazole ring group are described as the halogen atom, C1-8 alkyl group, and C1-8 alkoxy group in the above X or R 1 etc. The same as
- Examples of the C1-8 alkyl group having a substituent include a chloromethyl group, a fluoromethyl group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group, and a 2,2,2-trifluoro-1-methylethyl group.
- C1-8 haloalkyl groups such as: C3-8 cycloalkyl C1-8 alkyl groups such as cyclopropylmethyl, cyclobutylmethyl, and cyclopropylethyl groups; C1-8 such as methoxymethyl, ethoxymethyl, and ethoxyethyl groups 8 alkoxy C1-8 alkyl group; cyano C1-8 alkyl group such as cyanomethyl group; nitro C1-8 alkyl group such as nitromethyl group; C1-8 alkylthio C1-8 alkyl group such as methylthiomethyl group, ethylthiomethyl group; C6-10 aryl such as benzyl group and phenethyl group Kill group; acetyloxymethyl group, C1 ⁇ 7 acyloxy C1 ⁇ 8 alkyl group such as propionyloxymethyl group; and the like.
- Examples of the C2-8 alkenyl group and C2-8 alkynyl group in the substituent of the pyrazole ring group include the same as those described as the C2-8 alkenyl group and C2-8 alkynyl group in R 3 .
- Examples of the C1-8 alkylthio group include methylthio group, ethylthio group, n-propylthio group, i-propylthio group, n-butylthio group, i-butylthio group, s-butylthio group, t-butylthio group and the like.
- Examples of the C1-8 alkylsulfonyl group include a methylsulfonyl group, an ethylsulfonyl group, an i-propylsulfonyl group, and an n-butylsulfonyl group.
- Examples of the C1-8 alkylsulfonyloxy group include a methylsulfonyloxy group, an ethylsulfonyloxy group, an i-propylsulfonyloxy group, and an n-butylsulfonyloxy group.
- particularly preferred compounds are those in which the oxime ether derivative represented by the formula (I) or a salt thereof, wherein X is a C1-8 alkyl group, R 1 , R 2 , R 3 , R 4 and R 5 is independently a hydrogen atom or a C1-8 alkyl group, Y and Z are oxygen atoms, Q is unsubstituted or substituted 1H-pyrazol-3-yl group, unsubstituted or substituted A 2H-pyrazol-3-yl group having a group or an 1H-pyrazol-4-yl group having no substituent or a substituent, wherein m is 1 and n is 0 to 1.
- geometric isomers based on carbon-nitrogen double bonds may exist, and all of these isomers are included in the present invention.
- the salt of the oxime ether derivative that is the compound of the present invention is not particularly limited as long as it is a chemically acceptable salt.
- salts of alkali metals such as lithium, sodium and potassium
- salts of alkaline earth metals such as calcium and magnesium
- salts of transition metals such as iron and copper
- organic bases such as ammonia, triethylamine, tributylamine, pyridine and hydrazine And the like.
- the compound of the present invention has an excellent bactericidal activity against a wide variety of filamentous fungi, for example, bacteria belonging to algae fungi (Oomycetes), ascomycetes (Ascomycetes), imperfect fungi (Deuteromycetes), basidiomycetes (Basidiomycetes) Therefore, it is useful as an active ingredient of agricultural and horticultural fungicides.
- the compound of the present invention can be easily produced industrially in accordance with a known method, for example, the method described in Patent Document 3.
- the structure of the produced compound can be identified and confirmed by known analytical means such as IR spectrum, NMR spectrum, mass spectrum, and elemental analysis.
- the compound of the present invention include compounds shown in Tables (1) to (3).
- the compounds in Tables (1) to (3) are for illustrative purposes, and the compounds of the present invention are not limited thereto.
- Et represents an ethyl group
- i Pr represents an isopropyl group
- n Bu represents an n-butyl group
- s Bu represents a s-butyl group
- t Bu represents a t-butyl group
- c Pr represents a cyclo A propyl group and Ac represents an acetyl group, respectively.
- the fungicide of the present invention contains at least one selected from the compounds of the present invention as an active ingredient.
- the fungicides of the present invention are bacteria belonging to a wide variety of fungi, for example, algae fungi (Oomycetes), ascomycetes (Ascomycetes), incomplete fungi (Deuteromycetes), basidiomycetes (Basidiomycetes) Excellent sterilizing power.
- algae fungi Oomycetes
- ascomycetes Ascomycetes
- Deuteromycetes incomplete fungi
- Basidiomycetes Basidiomycetes
- Excellent sterilizing power for example, algae fungi (Oomycetes), ascomycetes (Ascomycetes), incomplete fungi (Deuteromycetes), basidiomycetes (Basidiomycetes) Excellent sterilizing power.
- the fungicide of the present invention can be used by using means such as seed treatment, foliage spraying, soil application or water surface application for the control of various diseases that occur during cultivation of agricultural and horticultural crops including flower buds, turf and grass. it can.
- “sugar beet” brown spot (Cercospora beticola); “peanut” brown spot (Mycosphaerella arachidis); black astringency (Mycosphaerella berkeleyi); “cucumber” powdery mildew (Sphaerotheca fuliginea), vine blight ( Mycosphaerella melonis), Mycorrhizal disease (Sclerotiniainsclerotiorum), Gray mold disease (Botrytis cinerea), Black spot disease (Cladosporium cucumerinum), Brown spot disease (Corynespora cassicola), Seedling disease (Pythium debaryanam, Rhizoctonia solani Kuhn) Disease (Pseudomonas syringae pv.Lecrymans); “Tomato” gray mold (Botrytis cinerea), leaf mold (Cladosporium fulvum); “Nasal” gray mold (Botrytis cinerea), black
- the bactericidal agent of the present invention has an excellent bactericidal effect against bacteria that have become resistant to conventional bactericides such as benzimidazole bactericides and dicarboximide fungicides.
- conventional bactericides such as benzimidazole bactericides and dicarboximide fungicides.
- gray mold fungus Botrytis cinerea
- sugar beet brown fungus Cercospora beticola
- apple black rot fungus Venturia inaequalis
- pear black star that show resistance to benzimidazole fungicides such as thiophanate methyl, benomyl, and carbendazim
- Examples include Venturia nashicola; gray mold fungus (Botrytis cinerea) that is resistant to dicarboximide fungicides (for example, vinclozolin, procymidone, iprodione).
- fungicide of the present invention is applied include sugar beet brown spot, wheat powdery mildew, rice blast, apple black spot, cucumber gray mold, peanut brown spot and the like.
- the fungicide of the present invention is a highly safe drug with little phytotoxicity, low toxicity to fish and warm-blooded animals.
- the fungicide of the present invention is used in a form that can be taken by general agricultural chemicals, that is, in the form of agrochemical preparations such as wettable powders, granules, powders, emulsions, aqueous solvents, suspensions, and wettable granules. May be.
- Additives and carriers used for solid preparations include vegetable powders such as soybean flour and wheat flour, mineral fine powders such as diatomaceous earth, apatite, gypsum, talc, bentonite, pyrophyllite and clay, benzoic acid Organic and inorganic compounds such as soda, urea and mirabilite can be mentioned.
- Solvents used for liquid formulations include kerosene, xylene and petroleum aromatic hydrocarbons, cyclohexane, cyclohexanone, dimethylformamide, dimethyl sulfoxide, alcohol, acetone, trichloroethylene, methyl isobutyl ketone, mineral oil, vegetable oil, Water etc. are mentioned.
- a surfactant can be added as necessary in order to take a uniform and stable form.
- the surfactant that can be added is not particularly limited.
- alkylphenyl ether added with polyoxyethylene alkyl ether added with polyoxyethylene, higher fatty acid ester added with polyoxyethylene, polyoxyethylene Sorbitan higher fatty acid ester added with polyoxyethylene, nonionic surfactant such as tristyryl phenyl ether added with polyoxyethylene, sulfate ester salt of alkylphenyl ether added with polyoxyethylene, alkylbenzene sulfonate, sulfuric acid of higher alcohol
- Examples include ester salts, alkyl naphthalene sulfonates, polycarboxylates, lignin sulfonates, formaldehyde condensates of alkyl naphthalene sulfonates, and isobutylene-maleic anhydride copolymers.
- the wettable powder, emulsion, flowable powder, aqueous solvent and granular wettable powder thus obtained are diluted with water to a predetermined concentration and sprayed on plants in the form of a solution, suspension or emulsion. Used in the way. Powders and granules are used as they are sprayed on plants.
- the amount of the active ingredient in the fungicide of the present invention is usually preferably 0.01 to 90% by weight, more preferably 0.05 to 85% by weight, based on the whole preparation.
- the application amount of the fungicide of the present invention varies depending on weather conditions, formulation form, application magnetism, application method, application place, disease to be controlled, target crop, etc., but usually 1 to 1,000 g of active ingredient compound per hectare, 10 to 100 g is preferred.
- the applied concentration is 1 to 1000 ppm, preferably 10 to 250 ppm.
- fungicides in addition to the compounds of the present invention, other fungicides, insecticides / acaricides, synergists and the like can also be mixed with the fungicides of the present invention.
- Typical examples of other fungicides, insecticides, acaricides, and plant growth regulators that can be used in combination are shown below.
- Fungicide Captan, phorpet, thiuram, ziram, dineb, manneb, mancozeb, propineb, polycarbamate, chlorothalonil, quintosen, captaphor, iprodione, prosaimidin, vinclozolin, fluoroimide, thymoxanyl, mepronil, flutolanil, pencyclon, oxycarboxyl, fosetyl aluminum, Propamocurve, triadimephone, triadimenol, propiconazole, diclobutrazole, viteltanol, hexaconazole, microbutanyl, flusilazole, metconazole, etaconazole, fluotrimazole, cyproconazole, epoxyconazole, flutriaphene, beconazole , Diniconazole, cyproconazole, phenalimol, triflumizole, prochlor , Imaza
- Insecticides and acaricides Organophosphorus and carbamate insecticides: Fenthion, Fenitrothion, Diazinon, Chlorpyrifos, ESP, Bamidthione, Fentoate, Dimethoate, Formothion, Marathon, Trichlorfone, Thiomethone, Phosmet, Dichlorvos, Acephate, EPBP, Methyl parathion, Oxydimethone methyl, Ethion, Salicione, Cyanophos, Fenthion, Salon Methidathione, Sulprophos, Chlorfenvinphos, Tetrachlorbinphos, Dimethylvinphos, Propafos, Isophenphos, Ethylthiomethone, Profenofos, Piracrofos, Monocrotophos, Adinfosmethyl, Aldicarb, Mesomil, Thiodicarb, Carbofuran, Carbosulfan, Benhracarb, Furatiocarb Propoxy
- Pyrethroid insecticides Permethrin, cypermethrin, deltamethrin, fenvalerate, fenpropatoline, pyrethrin, allethrin, tetramethrin, resmethrin, dimethrin, propraslin, phenothrin, protorin, fulvalinate, cyfluthrin, cyhalothrin, flucitrinate, etofenprox, cycloprotorin, thoramethrin , Silafluophene, brofenprox, aclinasrin, etc.
- Benzoylurea and other insecticides Diflubenzuron, chlorfluazuron, hexaflumuron, triflumuron, tetrabenzuron, flufenoxuron, flucycloxuron, buprofezin, pyriproxyfen, metoprene, benzoepin, diafenthiuron, acetamiprid, imidacloprid, nitenpyram, fipronil, cartap , Thiocyclam, bensultap, nicotine sulfate, rotenone, metaldehyde, machine oil, microbial pesticides such as BT and entomopathogenic viruses.
- Nematicides Phenamifos, phostiazates, etc.
- Acaricide Chlorbenzilate, phenisobromolate, dicophore, amitraz, BPPS, benzomate, hexithazox, fenbutazin oxide, polynactin, quinomethionate, CPCBS, tetradiphone, avermectin, milbemectin, clofentedin, cihexatin, pyridaben, fenpyroximate, tebufenpyrad, thiomidibene Dienochlor etc.
- Plant growth regulator Gibberellins (eg, gibberellin A3, gibberellin A4, gibberellin A7), IAA, NAA and the like.
- the compound of the present invention was produced according to the method described in Patent Document 3. Some of the produced compounds of the present invention are shown in Tables (4) to (6) together with physical property values. The NMR data is shown in Table (7).
- formulation examples of the fungicide of the present invention are shown below, but the additives and addition ratios are not limited to these formulation examples, and can be varied in a wide range. Moreover, the part in a formulation Example shows a weight part.
- Formulation Example 1 Wetting agent Oxime ether derivative compound of the present invention 40 parts Clay 48 parts Dioctyl sulfosuccinate sodium salt 4 parts Lignin sulfonic acid sodium salt 8 parts or more uniformly mixed and finely pulverized, active ingredient 40% Get a wettable powder.
- Emulsion Oxime ether derivative compound of the present invention 10 parts Solvesso 200 53 parts Cyclohexanone 26 parts Calcium dodecylbenzenesulfonate 1 part Polyoxyethylene alkylallyl ether 10 parts Mixing and dissolving the above, an emulsion containing 10% active ingredient obtain.
- Formulation Example 3 Powder A oxime ether derivative compound of the present invention 10 parts Clay 90 parts The above is uniformly mixed and finely pulverized to obtain a powder of 10% active ingredient.
- Formulation Example 4 Granule Oxime ether derivative compound of the present invention 5 parts Clay 73 parts Bentonite 20 parts Dioctyl sulfosuccinate sodium salt 1 part Potassium phosphate 1 part After the above is well ground and mixed, water is added and kneaded well Granulation and drying to obtain granules with 5% active ingredient.
- Suspension agent Oxime ether derivative compound of the present invention 10 parts Polyoxyethylene alkylallyl ether 4 parts Polycarboxylic acid sodium salt 2 parts Glycerin 10 parts Xanthan gum 0.2 parts Water 73.8 parts Is pulverized wet until it becomes 3 microns or less to obtain a suspension with 10% active ingredient.
- Formulation Example 6 Granule wettable powder Oxime ether derivative compound of the present invention 40 parts Clay 36 parts Potassium chloride 10 parts Alkylbenzenesulfonic acid sodium salt 1 part Lignin sulfonic acid sodium salt 8 parts Formaldehyde condensate of alkylbenzenesulfonic acid sodium salt 5 parts or more After mixing the mixture uniformly and finely pulverizing, add an appropriate amount of water and knead to make a clay. The clay-like product is granulated and then dried to obtain a wettable powder containing 40% of the active ingredient.
- Control value (%) (1 ⁇ / ⁇ ) ⁇ 100 ⁇ corresponds to the amount of fungal infection in the treated plant, ⁇ corresponds to the amount of fungal infection in untreated (control) plants.
- a control value of 0% means that the level of infection of the treated plants is consistent with that of the untreated control plants, and an effect of 100% means that the treated plants were not infected at all.
- the apple scab control test was conducted using compound numbers 1, 2, 3, 4, 5, 6, 7, 9, 10, 11, 12, 13, 14, 15, 16, 17, in Tables (4) to (6).
- the oxime ether derivative compounds of 18, 19, 20, 21, 22, 23, 24, 25, 26, and 27 were used. As a result, all the compounds showed an excellent control value of 75% or more.
- Test Example 2 Wheat powdery mildew control test A wettable powder prepared according to the formulation of Formulation Example 1 was diluted with water to adjust the active ingredient concentration to 100 ppm. The diluent was sprayed on wheat seedlings (variety “Chihoku”, 1.0-1.2 leaf stage) grown in an unglazed pot. The leaves were then air dried. The conidia of wheat powdery mildew (Erysiphe graminis f.sp.tritici) were shaken off and inoculated in a greenhouse at 22-25 ° C. for 7 days. The lesion appearance state on the leaf was compared with no treatment, and the control effect was examined.
- the wheat powdery mildew prevention test was conducted using compound numbers 1, 3, 4, 5, 7, 11, 12, 13, 16, 17, 18, 19, 20, 21, 22, 23, Tables (4) to (6). 24, 25, 26, and 27 oxime ether derivative compounds were carried out. As a result, all the compounds showed an excellent control value of 75% or more.
- Test Example 3 Wheat red rust control test A wettable powder produced according to the formulation of Preparation Example 1 was diluted with water to adjust the active ingredient concentration to 100 ppm. The diluent was sprayed on wheat seedlings grown in an unglazed pot (variety “Noribayashi No. 61”, 1.0-1.2 leaf stage). The leaves were then air dried. The wheat spores (Puccinia recondita) summer spores were shaken and inoculated, and kept in a greenhouse at 22-25 ° C. for 10 days. The lesion appearance state on the leaf was compared with no treatment, and the control effect was examined.
- the compound of the present invention can be easily produced industrially, has a large control effect at a small application rate for many agricultural and horticultural crops, and has an excellent osmotic migration and residual effect, and therefore has a control effect against diseases. It is a novel compound useful as an active ingredient of an agricultural and horticultural fungicide that is reliable and can be used safely.
- the fungicide of the present invention has an excellent control effect even when the concentration of the compound of the present invention is low and the application amount is small, and does not cause phytotoxicity or pollution to the plant body. It is a drug with excellent safety and less influence.
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Novel oxime ether derivatives represented by general formula (I) or salts thereof; and germicides for agricultural or horticultural use, which each contain at least one compound selected from among these compounds as an active ingredient. In general formula (I), X is C1-8 alkyl or the like; n represents the number of substituents X and is an integer of 0 to 4; R1 and R2 are each independently hydrogen or the like; m represents the number of repeats of a unit in parentheses and is an integer of 0 to 8; R3 is C1-8 alkyl or the like; R4 is C1-8 alkyl or the like; R5 is hydrogen or the like; Y is oxygen or sulfur; Z is oxygen or the like; and Q is a substituted or unsubstituted pyrazole-ring group.
Description
本発明は、オキシムエーテル誘導体またはその塩、並びに農園芸用殺菌剤に関する。より詳細に、本発明は、新規なオキシムエーテル誘導体またはその塩、並びに該オキシムエーテル誘導体またはその塩から選ばれる少なくとも1種を有効成分として含有する農園芸用殺菌剤に関する。
本願は、2010年3月1日に、日本に出願された特願2010-044194号に基づき優先権を主張し、その内容をここに援用する。 The present invention relates to an oxime ether derivative or a salt thereof, and an agricultural and horticultural fungicide. More specifically, the present invention relates to a novel oxime ether derivative or a salt thereof, and an agricultural and horticultural fungicide containing as an active ingredient at least one selected from the oxime ether derivative or a salt thereof.
This application claims priority on March 1, 2010 based on Japanese Patent Application No. 2010-044194 filed in Japan, the contents of which are incorporated herein by reference.
本願は、2010年3月1日に、日本に出願された特願2010-044194号に基づき優先権を主張し、その内容をここに援用する。 The present invention relates to an oxime ether derivative or a salt thereof, and an agricultural and horticultural fungicide. More specifically, the present invention relates to a novel oxime ether derivative or a salt thereof, and an agricultural and horticultural fungicide containing as an active ingredient at least one selected from the oxime ether derivative or a salt thereof.
This application claims priority on March 1, 2010 based on Japanese Patent Application No. 2010-044194 filed in Japan, the contents of which are incorporated herein by reference.
農園芸作物の栽培では、作物の病害に対して種々の防除薬剤が使用されている。しかしながらこうした防除薬剤の多くは、その防除効力が不十分である、薬剤耐性の病原菌の出現によりその使用が制限される、植物体に薬害や汚染を生ずる、若しくは人畜魚類に対する毒性や環境への影響が大きい、などの不具合があるため、十分に満足できる防除薬剤とは言い難い。そのため、かかる不具合が少なくて、防除効果が高く、安全に使用できる防除薬剤の出現が強く望まれている。
In the cultivation of agricultural and horticultural crops, various control agents are used against crop diseases. However, many of these control agents have insufficient control efficacy, their use is limited by the emergence of drug-resistant pathogens, cause phytotoxicity and pollution to plants, or are toxic to human fish and have an impact on the environment. It is difficult to say that it is a satisfactory control agent because of the problems such as large For this reason, there is a strong demand for the emergence of a control agent that has few such problems, has a high control effect, and can be used safely.
本発明に関連して、オキシアミン誘導体(特許文献1)、オキシム誘導体(特許文献2)、若しくはオキシムエーテル誘導体(特許文献3)などが提案されている。
In connection with the present invention, oxyamine derivatives (Patent Document 1), oxime derivatives (Patent Document 2), oxime ether derivatives (Patent Document 3), and the like have been proposed.
特許文献1~3に記載されているオキシアミン誘導体、オキシム誘導体、若しくはオキシムエーテル誘導体またはその塩は、工業的に容易に合成でき、防除効果が高く、安全に使用できる防除薬剤として使用できるものであった。しかし、特許文献1~3に記載されている化合物は、防除薬剤として使用する際に必要とする化合物の施用量(g/ヘクタール)が、対象病害によっては比較的多く必要であり、また農園芸作物に対する化合物の浸透移行性が低いため実用面において十分な防除効果が得られない場合があった。
このような実情に鑑み、本発明は、工業的に容易に製造でき、低い濃度で且つ施用量が少なくても防除効果が大きく、また多くの農園芸作物に対する浸透移行性と残効性が高く、病害に対する防除効果が確実で、且つ安全に使用できる農園芸用殺菌剤の有効成分となりうる、新規オキシムエーテル誘導体またはその塩、並びに農園芸用殺菌剤を提供することを課題とするものである。 The oxyamine derivatives, oxime derivatives, or oxime ether derivatives or salts thereof described in Patent Documents 1 to 3 can be easily synthesized industrially, have a high control effect, and can be used as safe control agents. It was. However, the compounds described in Patent Documents 1 to 3 require a relatively large application amount (g / ha) of the compound required for use as a control agent depending on the target disease. Due to the low permeability of the compound to crops, there was a case where a sufficient control effect was not obtained in practical use.
In view of such circumstances, the present invention can be easily manufactured industrially, has a large control effect even at a low concentration and a small application amount, and has high penetrability and residual effect on many agricultural and horticultural crops. It is an object of the present invention to provide a novel oxime ether derivative or a salt thereof, and an agricultural and horticultural fungicide, which can be an active ingredient of an agricultural and horticultural fungicide that has a reliable disease control effect and can be used safely. .
このような実情に鑑み、本発明は、工業的に容易に製造でき、低い濃度で且つ施用量が少なくても防除効果が大きく、また多くの農園芸作物に対する浸透移行性と残効性が高く、病害に対する防除効果が確実で、且つ安全に使用できる農園芸用殺菌剤の有効成分となりうる、新規オキシムエーテル誘導体またはその塩、並びに農園芸用殺菌剤を提供することを課題とするものである。 The oxyamine derivatives, oxime derivatives, or oxime ether derivatives or salts thereof described in Patent Documents 1 to 3 can be easily synthesized industrially, have a high control effect, and can be used as safe control agents. It was. However, the compounds described in Patent Documents 1 to 3 require a relatively large application amount (g / ha) of the compound required for use as a control agent depending on the target disease. Due to the low permeability of the compound to crops, there was a case where a sufficient control effect was not obtained in practical use.
In view of such circumstances, the present invention can be easily manufactured industrially, has a large control effect even at a low concentration and a small application amount, and has high penetrability and residual effect on many agricultural and horticultural crops. It is an object of the present invention to provide a novel oxime ether derivative or a salt thereof, and an agricultural and horticultural fungicide, which can be an active ingredient of an agricultural and horticultural fungicide that has a reliable disease control effect and can be used safely. .
本発明者らは上記課題を解決すべく鋭意検討した。その結果、式(I)で表される、ピラゾール環基を有する新規なオキシムエーテル誘導体またはその塩を得るに至った。そして、これらオキシムエーテル誘導体またはその塩は、工業的に容易に製造できること、また、これらの化合物から選ばれる少なくとも1種を有効成分として含有する農園芸用殺菌剤が、低い濃度で且つ施用量が少なくても防除効果が大きいこと、多くの農園芸作物に対する浸透移行性と残効性が高いため病害に対する防除効果が確実であること、および植物体への薬害や汚染が少なく人畜魚類に対する毒性や環境への影響が少ないので安全性に優れること、を見出した。本発明は、これらの知見に基づきさらに検討を重ねることによって、完成するに至ったものである。
The present inventors diligently studied to solve the above problems. As a result, a novel oxime ether derivative having a pyrazole ring group represented by the formula (I) or a salt thereof was obtained. These oxime ether derivatives or salts thereof can be easily produced industrially, and agricultural and horticultural fungicides containing at least one selected from these compounds as an active ingredient have a low concentration and an application rate. At least, the control effect is large, the penetration and retentivity to many agricultural and horticultural crops is high, and the control effect against diseases is certain, and there is little phytotoxicity and pollution to plants, We found that it has excellent safety because it has little impact on the environment. The present invention has been completed by further studies based on these findings.
すなわち、本発明は以下の態様を包含するものである。
That is, the present invention includes the following aspects.
〔1〕 式(I)で表されるオキシムエーテル誘導体またはその塩(以下、本発明化合物と表記することがある)。
[1] An oxime ether derivative represented by the formula (I) or a salt thereof (hereinafter sometimes referred to as the present compound).
〔式(I)中、Xはハロゲン原子、C1~8アルキル基、C1~8アルコキシ基、C1~8ハロアルキル基、またはC1~8ハロアルコキシ基を表す。nはXの置換数を表わし且つ0~4のいずれかの整数である。nが2以上の場合、X同士は、同一であっても、相異なっていてもよい。
R1およびR2はそれぞれ独立して、水素原子、ハロゲン原子、C1~8アルキル基、C1~8ハロアルキル基、または無置換の若しくは置換基を有するC3~8シクロアルキル基を表す。R1とR2とが一緒になって結合して環を形成してもよい。mは括弧内の単位の繰返し数を表わし且つ0~8のいずれかの整数である。mが2以上の場合、R1同士、R2同士は、同一であっても、相異なっていてもよい。
R3は、水素原子、C1~8アルキル基、C2~8アルケニル基、C2~8アルキニル基、C1~8ハロアルキル基、C2~8ハロアルケニル基、C2~8ハロアルキニル基、または無置換の若しくは置換基を有するC3~8シクロアルキル基を表す。
R4は、水素原子、C1~8アルキル基、無置換の若しくは置換基を有するC3~8シクロアルキル基、C2~8アルケニル基、C2~8アルキニル基、C1~8ハロアルキル基、C2~8ハロアルケニル基、またはC2~8ハロアルキニル基を表す。
R5は、水素原子、C1~8アルキル基、アシル基、ホルミル基、C1~8アルコキシC1~8アルキル基、C2~8アシルオキシC1~8アルキル基、C1~8アルコキシカルボニル基、C1~8アルキルスルホニル基、または無置換の若しくは置換基を有するフェニルスルホニル基を表す。
Yは、酸素原子または硫黄原子を表す。
Zは、単結合、酸素原子、硫黄原子、またはNR6で示される基を表す。R6は、水素原子若しくはC1~8アルキル基を表す。
Qは、無置換の若しくは置換基を有するピラゾール環基を表す。〕 [In the formula (I), X represents a halogen atom, a C1-8 alkyl group, a C1-8 alkoxy group, a C1-8 haloalkyl group, or a C1-8 haloalkoxy group. n represents the number of substitutions of X and is an integer from 0 to 4. When n is 2 or more, Xs may be the same or different.
R 1 and R 2 each independently represents a hydrogen atom, a halogen atom, a C1-8 alkyl group, a C1-8 haloalkyl group, or an unsubstituted or substituted C3-8 cycloalkyl group. R 1 and R 2 may be bonded together to form a ring. m represents the number of repeating units in parentheses and is an integer from 0 to 8. When m is 2 or more, R 1 and R 2 may be the same or different.
R 3 is a hydrogen atom, a C1-8 alkyl group, a C2-8 alkenyl group, a C2-8 alkynyl group, a C1-8 haloalkyl group, a C2-8 haloalkenyl group, a C2-8 haloalkynyl group, or an unsubstituted or Represents a C3-8 cycloalkyl group having a substituent.
R 4 represents a hydrogen atom, a C1-8 alkyl group, an unsubstituted or substituted C3-8 cycloalkyl group, a C2-8 alkenyl group, a C2-8 alkynyl group, a C1-8 haloalkyl group, a C2-8 halo. It represents an alkenyl group or a C2-8 haloalkynyl group.
R 5 is a hydrogen atom, C1-8 alkyl group, acyl group, formyl group, C1-8 alkoxy C1-8 alkyl group, C2-8 acyloxy C1-8 alkyl group, C1-8 alkoxycarbonyl group, C1-8 alkyl A sulfonyl group or an unsubstituted or substituted phenylsulfonyl group is represented.
Y represents an oxygen atom or a sulfur atom.
Z represents a single bond, an oxygen atom, a sulfur atom, or a group represented by NR 6 . R 6 represents a hydrogen atom or a C1-8 alkyl group.
Q represents an unsubstituted or substituted pyrazole ring group. ]
R1およびR2はそれぞれ独立して、水素原子、ハロゲン原子、C1~8アルキル基、C1~8ハロアルキル基、または無置換の若しくは置換基を有するC3~8シクロアルキル基を表す。R1とR2とが一緒になって結合して環を形成してもよい。mは括弧内の単位の繰返し数を表わし且つ0~8のいずれかの整数である。mが2以上の場合、R1同士、R2同士は、同一であっても、相異なっていてもよい。
R3は、水素原子、C1~8アルキル基、C2~8アルケニル基、C2~8アルキニル基、C1~8ハロアルキル基、C2~8ハロアルケニル基、C2~8ハロアルキニル基、または無置換の若しくは置換基を有するC3~8シクロアルキル基を表す。
R4は、水素原子、C1~8アルキル基、無置換の若しくは置換基を有するC3~8シクロアルキル基、C2~8アルケニル基、C2~8アルキニル基、C1~8ハロアルキル基、C2~8ハロアルケニル基、またはC2~8ハロアルキニル基を表す。
R5は、水素原子、C1~8アルキル基、アシル基、ホルミル基、C1~8アルコキシC1~8アルキル基、C2~8アシルオキシC1~8アルキル基、C1~8アルコキシカルボニル基、C1~8アルキルスルホニル基、または無置換の若しくは置換基を有するフェニルスルホニル基を表す。
Yは、酸素原子または硫黄原子を表す。
Zは、単結合、酸素原子、硫黄原子、またはNR6で示される基を表す。R6は、水素原子若しくはC1~8アルキル基を表す。
Qは、無置換の若しくは置換基を有するピラゾール環基を表す。〕 [In the formula (I), X represents a halogen atom, a C1-8 alkyl group, a C1-8 alkoxy group, a C1-8 haloalkyl group, or a C1-8 haloalkoxy group. n represents the number of substitutions of X and is an integer from 0 to 4. When n is 2 or more, Xs may be the same or different.
R 1 and R 2 each independently represents a hydrogen atom, a halogen atom, a C1-8 alkyl group, a C1-8 haloalkyl group, or an unsubstituted or substituted C3-8 cycloalkyl group. R 1 and R 2 may be bonded together to form a ring. m represents the number of repeating units in parentheses and is an integer from 0 to 8. When m is 2 or more, R 1 and R 2 may be the same or different.
R 3 is a hydrogen atom, a C1-8 alkyl group, a C2-8 alkenyl group, a C2-8 alkynyl group, a C1-8 haloalkyl group, a C2-8 haloalkenyl group, a C2-8 haloalkynyl group, or an unsubstituted or Represents a C3-8 cycloalkyl group having a substituent.
R 4 represents a hydrogen atom, a C1-8 alkyl group, an unsubstituted or substituted C3-8 cycloalkyl group, a C2-8 alkenyl group, a C2-8 alkynyl group, a C1-8 haloalkyl group, a C2-8 halo. It represents an alkenyl group or a C2-8 haloalkynyl group.
R 5 is a hydrogen atom, C1-8 alkyl group, acyl group, formyl group, C1-8 alkoxy C1-8 alkyl group, C2-8 acyloxy C1-8 alkyl group, C1-8 alkoxycarbonyl group, C1-8 alkyl A sulfonyl group or an unsubstituted or substituted phenylsulfonyl group is represented.
Y represents an oxygen atom or a sulfur atom.
Z represents a single bond, an oxygen atom, a sulfur atom, or a group represented by NR 6 . R 6 represents a hydrogen atom or a C1-8 alkyl group.
Q represents an unsubstituted or substituted pyrazole ring group. ]
〔2〕 XがC1~8アルキル基であり、R1、R2、R3、R4およびR5がそれぞれ独立に水素原子またはC1~8アルキル基であり、YおよびZが酸素原子であり、Qが無置換の若しくは置換基を有する1H-ピラゾール-3-イル基、無置換の若しくは置換基を有する2H-ピラゾール-3-イル基、または無置換の若しくは置換基を有する1H-ピラゾール-4-イル基であり、mが1であり、且つnが0~1である、前記〔1〕に記載のオキシムエーテル誘導体またはその塩。
[2] X is a C1-8 alkyl group, R 1 , R 2 , R 3 , R 4 and R 5 are each independently a hydrogen atom or a C1-8 alkyl group, and Y and Z are oxygen atoms , Q is unsubstituted or substituted 1H-pyrazol-3-yl group, unsubstituted or substituted 2H-pyrazol-3-yl group, or unsubstituted or substituted 1H-pyrazol- The oxime ether derivative or the salt thereof according to [1] above, which is a 4-yl group, m is 1, and n is 0 to 1.
〔3〕 前記〔1〕または〔2〕に記載のオキシムエーテル誘導体またはその塩から選ばれる少なくとも1種を有効成分として含有する農園芸用殺菌剤(以下、本発明殺菌剤と表記することがある。)。
[3] An agricultural and horticultural fungicide containing as an active ingredient at least one selected from the oxime ether derivatives or salts thereof according to [1] or [2] (hereinafter sometimes referred to as the present invention fungicide) .)
本発明化合物は、工業的に容易に製造することができ、多くの農園芸作物に対して、少ない施用量で防除効果が大きく、浸透移行性と残効性が優れるために病害に対する防除効果が確実で、しかも安全に使用できる農園芸用殺菌剤の活性成分として有用な新規化合物である。
The compound of the present invention can be easily produced industrially, has a large control effect at a small application rate for many agricultural and horticultural crops, and has an excellent osmotic migration and residual effect, and therefore has a control effect against diseases. It is a novel compound useful as an active ingredient of an agricultural and horticultural fungicide that is reliable and can be used safely.
本発明殺菌剤は、本発明化合物の濃度が低く且つ施用量が少なくても、優れた防除効果を有し、植物体に薬害や汚染を生じることがなく、人畜魚類に対する毒性や環境への影響が少ない、安全性に優れる薬剤である。
The fungicide of the present invention has an excellent control effect even when the concentration of the compound of the present invention is low and the application amount is small, does not cause phytotoxicity or contamination on the plant body, and is toxic to human and livestock and has an impact on the environment. It is a drug with excellent safety.
このような本発明が有する効果は、特許文献1~3の知見から予測することは困難であり、特に低い濃度で且つ施用量が少なくても防除効果が大きく、多くの農園芸作物に対して浸透移行性や残効性が高いため病害に対する防除効果が確実である、という効果は特許文献3から予測することはできない。
Such an effect of the present invention is difficult to predict from the knowledge of Patent Documents 1 to 3, and has a large control effect even at a low concentration and a small application amount, and is effective for many agricultural and horticultural crops. From the patent document 3, it is impossible to predict the effect that the effect of controlling the disease is certain due to the high permeability and residual effect.
(1)オキシムエーテル誘導体またはその塩
本発明化合物は、式(I)で表されるオキシムエーテル誘導体またはその塩である。 (1) Oxime ether derivative or salt thereof The compound of the present invention is an oxime ether derivative represented by the formula (I) or a salt thereof.
本発明化合物は、式(I)で表されるオキシムエーテル誘導体またはその塩である。 (1) Oxime ether derivative or salt thereof The compound of the present invention is an oxime ether derivative represented by the formula (I) or a salt thereof.
[ X ]
式(I)中、Xはハロゲン原子、C1~8アルキル基、C1~8アルコキシ基、C1~8ハロアルキル基、またはC1~8ハロアルコキシ基を表す。nはXの置換数を表わし且つ0~4のいずれかの整数、好ましくは0~2のいずれかの整数、より好ましくは1である。nが2以上の場合、X同士は、同一であっても、相異なっていてもよい。 [X]
In the formula (I), X represents a halogen atom, a C1-8 alkyl group, a C1-8 alkoxy group, a C1-8 haloalkyl group, or a C1-8 haloalkoxy group. n represents the number of substitutions of X and is an integer of 0 to 4, preferably an integer of 0 to 2, more preferably 1. When n is 2 or more, Xs may be the same or different.
式(I)中、Xはハロゲン原子、C1~8アルキル基、C1~8アルコキシ基、C1~8ハロアルキル基、またはC1~8ハロアルコキシ基を表す。nはXの置換数を表わし且つ0~4のいずれかの整数、好ましくは0~2のいずれかの整数、より好ましくは1である。nが2以上の場合、X同士は、同一であっても、相異なっていてもよい。 [X]
In the formula (I), X represents a halogen atom, a C1-8 alkyl group, a C1-8 alkoxy group, a C1-8 haloalkyl group, or a C1-8 haloalkoxy group. n represents the number of substitutions of X and is an integer of 0 to 4, preferably an integer of 0 to 2, more preferably 1. When n is 2 or more, Xs may be the same or different.
ハロゲン原子としては、フッ素原子、塩素原子、臭素原子などが挙げられる。
C1~8アルキル基は、直鎖状であっても、分岐していてもよい。例えば、メチル基、エチル基、n-プロピル基、i-プロピル基、n-ブチル基、i-ブチル基、s-ブチル基、t-ブチル基、n-ペンチル基、n-ヘキシル基、n-ヘプチル基、n-オクチル基などが挙げられる。
C1~8アルコキシ基は、直鎖状であっても、分岐していてもよい。例えば、メトキシ基、エトキシ基、n-プロポキシ基、i-プロポキシ基、n-ブトキシ基、i-ブトキシ基、s-ブトキシ基、t-ブトキシ基、n-ペンチルオキシ基、n-ヘキシルオキシ基などが挙げられる。
C1~8ハロアルキル基は、ハロゲン原子で置換されたアルキル基であれば特に制限されない。例えば、フルオロメチル基、クロロメチル基、ブロモメチル基、ジフルオロメチル基、ジクロロメチル基、ジブロモメチル基、トリフルオロメチル基、トリクロロメチル基、トリブロモメチル基、2,2,2-トルフルオロエチル基、2,2,2-トリクロロエチル基、ペンタフルオロエチル基などが挙げられる。
C1~8ハロアルコキシ基は、ハロゲン原子で置換されたアルコキシ基であれば特に制限されない。例えば、クロロメトキシ基、ジクロロメトキシ基、トリクロロメトキシ基、トリフルオロメトキシ基、1-フルオロエトキシ基、1,1-ジフルオロエトキシ基、2,2,2-トリフルオロエトキシ基、ペンタフルオロエトキシ基などが挙げられる。
これらのうち、XはC1~8アルキル基であることが好ましい。 Examples of the halogen atom include a fluorine atom, a chlorine atom, and a bromine atom.
The C1-8 alkyl group may be linear or branched. For example, methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, s-butyl group, t-butyl group, n-pentyl group, n-hexyl group, n- A heptyl group, n-octyl group, etc. are mentioned.
The C1-8 alkoxy group may be linear or branched. For example, methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, i-butoxy group, s-butoxy group, t-butoxy group, n-pentyloxy group, n-hexyloxy group, etc. Is mentioned.
The C1-8 haloalkyl group is not particularly limited as long as it is an alkyl group substituted with a halogen atom. For example, fluoromethyl group, chloromethyl group, bromomethyl group, difluoromethyl group, dichloromethyl group, dibromomethyl group, trifluoromethyl group, trichloromethyl group, tribromomethyl group, 2,2,2-trifluoroethyl group, Examples include 2,2,2-trichloroethyl group, pentafluoroethyl group and the like.
The C1-8 haloalkoxy group is not particularly limited as long as it is an alkoxy group substituted with a halogen atom. For example, chloromethoxy group, dichloromethoxy group, trichloromethoxy group, trifluoromethoxy group, 1-fluoroethoxy group, 1,1-difluoroethoxy group, 2,2,2-trifluoroethoxy group, pentafluoroethoxy group, etc. Can be mentioned.
Of these, X is preferably a C1-8 alkyl group.
C1~8アルキル基は、直鎖状であっても、分岐していてもよい。例えば、メチル基、エチル基、n-プロピル基、i-プロピル基、n-ブチル基、i-ブチル基、s-ブチル基、t-ブチル基、n-ペンチル基、n-ヘキシル基、n-ヘプチル基、n-オクチル基などが挙げられる。
C1~8アルコキシ基は、直鎖状であっても、分岐していてもよい。例えば、メトキシ基、エトキシ基、n-プロポキシ基、i-プロポキシ基、n-ブトキシ基、i-ブトキシ基、s-ブトキシ基、t-ブトキシ基、n-ペンチルオキシ基、n-ヘキシルオキシ基などが挙げられる。
C1~8ハロアルキル基は、ハロゲン原子で置換されたアルキル基であれば特に制限されない。例えば、フルオロメチル基、クロロメチル基、ブロモメチル基、ジフルオロメチル基、ジクロロメチル基、ジブロモメチル基、トリフルオロメチル基、トリクロロメチル基、トリブロモメチル基、2,2,2-トルフルオロエチル基、2,2,2-トリクロロエチル基、ペンタフルオロエチル基などが挙げられる。
C1~8ハロアルコキシ基は、ハロゲン原子で置換されたアルコキシ基であれば特に制限されない。例えば、クロロメトキシ基、ジクロロメトキシ基、トリクロロメトキシ基、トリフルオロメトキシ基、1-フルオロエトキシ基、1,1-ジフルオロエトキシ基、2,2,2-トリフルオロエトキシ基、ペンタフルオロエトキシ基などが挙げられる。
これらのうち、XはC1~8アルキル基であることが好ましい。 Examples of the halogen atom include a fluorine atom, a chlorine atom, and a bromine atom.
The C1-8 alkyl group may be linear or branched. For example, methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, s-butyl group, t-butyl group, n-pentyl group, n-hexyl group, n- A heptyl group, n-octyl group, etc. are mentioned.
The C1-8 alkoxy group may be linear or branched. For example, methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, i-butoxy group, s-butoxy group, t-butoxy group, n-pentyloxy group, n-hexyloxy group, etc. Is mentioned.
The C1-8 haloalkyl group is not particularly limited as long as it is an alkyl group substituted with a halogen atom. For example, fluoromethyl group, chloromethyl group, bromomethyl group, difluoromethyl group, dichloromethyl group, dibromomethyl group, trifluoromethyl group, trichloromethyl group, tribromomethyl group, 2,2,2-trifluoroethyl group, Examples include 2,2,2-trichloroethyl group, pentafluoroethyl group and the like.
The C1-8 haloalkoxy group is not particularly limited as long as it is an alkoxy group substituted with a halogen atom. For example, chloromethoxy group, dichloromethoxy group, trichloromethoxy group, trifluoromethoxy group, 1-fluoroethoxy group, 1,1-difluoroethoxy group, 2,2,2-trifluoroethoxy group, pentafluoroethoxy group, etc. Can be mentioned.
Of these, X is preferably a C1-8 alkyl group.
[ R1、R2 ]
R1およびR2はそれぞれ独立して、水素原子、ハロゲン原子、C1~8アルキル基、C1~8ハロアルキル基、または無置換の若しくは置換基を有するC3~8シクロアルキル基を表す。mは括弧内の単位の繰返し数を表わし且つ0~8のいずれかの整数、好ましくは0~3のいずれかの整数、より好ましくは0~1のいずれかの整数である。mが2以上の場合、R1同士、R2同士は、同一であっても、相異なっていてもよい。 [R 1, R 2]
R 1 and R 2 each independently represents a hydrogen atom, a halogen atom, a C1-8 alkyl group, a C1-8 haloalkyl group, or an unsubstituted or substituted C3-8 cycloalkyl group. m represents the number of repeating units in parentheses and is an integer from 0 to 8, preferably an integer from 0 to 3, more preferably an integer from 0 to 1. When m is 2 or more, R 1 and R 2 may be the same or different.
R1およびR2はそれぞれ独立して、水素原子、ハロゲン原子、C1~8アルキル基、C1~8ハロアルキル基、または無置換の若しくは置換基を有するC3~8シクロアルキル基を表す。mは括弧内の単位の繰返し数を表わし且つ0~8のいずれかの整数、好ましくは0~3のいずれかの整数、より好ましくは0~1のいずれかの整数である。mが2以上の場合、R1同士、R2同士は、同一であっても、相異なっていてもよい。 [R 1, R 2]
R 1 and R 2 each independently represents a hydrogen atom, a halogen atom, a C1-8 alkyl group, a C1-8 haloalkyl group, or an unsubstituted or substituted C3-8 cycloalkyl group. m represents the number of repeating units in parentheses and is an integer from 0 to 8, preferably an integer from 0 to 3, more preferably an integer from 0 to 1. When m is 2 or more, R 1 and R 2 may be the same or different.
R1およびR2における、ハロゲン原子、C1~8アルキル基、およびC1~8ハロアルキル基としては、前記Xにおけるハロゲン原子、C1~8アルキル基、およびC1~8ハロアルキル基として記述したものと同じものが挙げられる。
無置換のC3~8シクロアルキル基としては、シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基、シクロヘプチル基、シクロオクチル基などが挙げられる。
C3~8シクロアルキル基の置換基としては、フッ素原子、塩素原子、臭素原子などのハロゲン原子;メチル基、エチル基などのC1~6アルキル基;メトキシ基、エトキシ基などのC1~6アルコキシ基;ニトロ基;シアノ基;などが挙げられる。
R1とR2とは一緒になって結合して環を形成してもよい。該環には、酸素原子、硫黄原子や窒素原子などのヘテロ原子が含まれていてもよい。かかる環としては、シクロプロパン環、シクロペンタン環、シクロヘキサン環、テトラヒドロピラン環などが挙げられる。 The halogen atom, C1-8 alkyl group, and C1-8 haloalkyl group in R 1 and R 2 are the same as those described as the halogen atom, C1-8 alkyl group, and C1-8 haloalkyl group in X above. Is mentioned.
Examples of the unsubstituted C3-8 cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group.
Substituents for C3-8 cycloalkyl groups include: halogen atoms such as fluorine, chlorine and bromine; C1-6 alkyl groups such as methyl and ethyl groups; C1-6 alkoxy groups such as methoxy and ethoxy groups Nitro group; cyano group; and the like.
R 1 and R 2 may be bonded together to form a ring. The ring may contain a hetero atom such as an oxygen atom, a sulfur atom or a nitrogen atom. Examples of such a ring include a cyclopropane ring, a cyclopentane ring, a cyclohexane ring, and a tetrahydropyran ring.
無置換のC3~8シクロアルキル基としては、シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基、シクロヘプチル基、シクロオクチル基などが挙げられる。
C3~8シクロアルキル基の置換基としては、フッ素原子、塩素原子、臭素原子などのハロゲン原子;メチル基、エチル基などのC1~6アルキル基;メトキシ基、エトキシ基などのC1~6アルコキシ基;ニトロ基;シアノ基;などが挙げられる。
R1とR2とは一緒になって結合して環を形成してもよい。該環には、酸素原子、硫黄原子や窒素原子などのヘテロ原子が含まれていてもよい。かかる環としては、シクロプロパン環、シクロペンタン環、シクロヘキサン環、テトラヒドロピラン環などが挙げられる。 The halogen atom, C1-8 alkyl group, and C1-8 haloalkyl group in R 1 and R 2 are the same as those described as the halogen atom, C1-8 alkyl group, and C1-8 haloalkyl group in X above. Is mentioned.
Examples of the unsubstituted C3-8 cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group.
Substituents for C3-8 cycloalkyl groups include: halogen atoms such as fluorine, chlorine and bromine; C1-6 alkyl groups such as methyl and ethyl groups; C1-6 alkoxy groups such as methoxy and ethoxy groups Nitro group; cyano group; and the like.
R 1 and R 2 may be bonded together to form a ring. The ring may contain a hetero atom such as an oxygen atom, a sulfur atom or a nitrogen atom. Examples of such a ring include a cyclopropane ring, a cyclopentane ring, a cyclohexane ring, and a tetrahydropyran ring.
[ R3 ]
R3は、水素原子、C1~8アルキル基、C2~8アルケニル基、C2~8アルキニル基、C1~8ハロアルキル基、C2~8ハロアルケニル基、C2~8ハロアルキニル基、または無置換の若しくは置換基を有するC3~8シクロアルキル基を表す。 [R 3]
R 3 is a hydrogen atom, a C1-8 alkyl group, a C2-8 alkenyl group, a C2-8 alkynyl group, a C1-8 haloalkyl group, a C2-8 haloalkenyl group, a C2-8 haloalkynyl group, or an unsubstituted or Represents a C3-8 cycloalkyl group having a substituent.
R3は、水素原子、C1~8アルキル基、C2~8アルケニル基、C2~8アルキニル基、C1~8ハロアルキル基、C2~8ハロアルケニル基、C2~8ハロアルキニル基、または無置換の若しくは置換基を有するC3~8シクロアルキル基を表す。 [R 3]
R 3 is a hydrogen atom, a C1-8 alkyl group, a C2-8 alkenyl group, a C2-8 alkynyl group, a C1-8 haloalkyl group, a C2-8 haloalkenyl group, a C2-8 haloalkynyl group, or an unsubstituted or Represents a C3-8 cycloalkyl group having a substituent.
R3におけるC1~8アルキル基、C1~8ハロアルキル基、および無置換の若しくは置換基を有するC3~8シクロアルキル基としては、前記XまたはR1などにおける、C1~8アルキル基、C1~8ハロアルキル基、および無置換の若しくは置換基を有するC3~8シクロアルキル基として記述したものと同じものが挙げられる。
C1 ~ 8 alkyl group for R 3, examples of C3 ~ 8 cycloalkyl group having C1 ~ 8 haloalkyl group, and an unsubstituted or substituted group, such as in the X or R 1, C1 ~ 8 alkyl, C1 ~ 8 Examples include the same haloalkyl groups and those described as unsubstituted or substituted C3-8 cycloalkyl groups.
C2~8アルケニル基としては、ビニル基、1-プロペニル基、2-プロペニル基、1-ブテニル基、2-ブテニル基、3-ブテニル基、1-メチル-2-プロペニル基、2-メチル-2-プロペニル基、1-ペンテニル基、2-ペンテニル基、3-ペンテニル基、4-ペンテニル基、1-メチル-2-ブテニル基、2-メチル-2-ブテニル基、1-ヘキセニル基、2-ヘキセニル基、3-ヘキセニル基、4-ヘキセニル基、5-ヘキセニル基などが挙げられる。
C2~8アルキニル基としては、エチニル基、1-プロピニル基、プロパルギル基、1-ブチニル基、2-ブチニル基、3-ブチニル基、1-メチル-2-プロピニル基、2-メチル-3-ブチニル基、1-ペンチニル基、2-ペンチニル基、3-ペンチニル基、4-ペンチニル基、1-メチル-2-ブチニル基、2-メチル-3-ペンチニル基、1-ヘキシニル基、1,1-ジメチル-2-ブチニル基などが挙げられる。
C2~8ハロアルケニル基としては、3-クロロ-2-プロペニル基、4-クロロ-2-ブテニル基、4,4-ジクロロ-3-ブテニル基、4,4-ジフルオロ-3-ブテニル基、3,3-ジクロロ-2-プロペニル基などが挙げられる。
C2~8ハロアルキニル基としては、3-クロロ-1-プロピニル基、3-クロロ-1-ブチニル基、3-ブロモ-1-ブチニル基、3-ブロモ-2-プロピニル基、3-ヨード-2-プロピニル基などが挙げられる。 C2-8 alkenyl groups include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl-2 -Propenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group, 2-methyl-2-butenyl group, 1-hexenyl group, 2-hexenyl group Group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group and the like.
C2-8 alkynyl groups include ethynyl, 1-propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 2-methyl-3-butynyl Group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 2-methyl-3-pentynyl group, 1-hexynyl group, 1,1-dimethyl Examples include a -2-butynyl group.
The C2-8 haloalkenyl group includes a 3-chloro-2-propenyl group, a 4-chloro-2-butenyl group, a 4,4-dichloro-3-butenyl group, a 4,4-difluoro-3-butenyl group, 3 , 3-dichloro-2-propenyl group and the like.
C2-8 haloalkynyl groups include 3-chloro-1-propynyl group, 3-chloro-1-butynyl group, 3-bromo-1-butynyl group, 3-bromo-2-propynyl group, 3-iodo-2 -Propynyl group and the like.
C2~8アルキニル基としては、エチニル基、1-プロピニル基、プロパルギル基、1-ブチニル基、2-ブチニル基、3-ブチニル基、1-メチル-2-プロピニル基、2-メチル-3-ブチニル基、1-ペンチニル基、2-ペンチニル基、3-ペンチニル基、4-ペンチニル基、1-メチル-2-ブチニル基、2-メチル-3-ペンチニル基、1-ヘキシニル基、1,1-ジメチル-2-ブチニル基などが挙げられる。
C2~8ハロアルケニル基としては、3-クロロ-2-プロペニル基、4-クロロ-2-ブテニル基、4,4-ジクロロ-3-ブテニル基、4,4-ジフルオロ-3-ブテニル基、3,3-ジクロロ-2-プロペニル基などが挙げられる。
C2~8ハロアルキニル基としては、3-クロロ-1-プロピニル基、3-クロロ-1-ブチニル基、3-ブロモ-1-ブチニル基、3-ブロモ-2-プロピニル基、3-ヨード-2-プロピニル基などが挙げられる。 C2-8 alkenyl groups include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl-2 -Propenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group, 2-methyl-2-butenyl group, 1-hexenyl group, 2-hexenyl group Group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group and the like.
C2-8 alkynyl groups include ethynyl, 1-propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 2-methyl-3-butynyl Group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 2-methyl-3-pentynyl group, 1-hexynyl group, 1,1-dimethyl Examples include a -2-butynyl group.
The C2-8 haloalkenyl group includes a 3-chloro-2-propenyl group, a 4-chloro-2-butenyl group, a 4,4-dichloro-3-butenyl group, a 4,4-difluoro-3-butenyl group, 3 , 3-dichloro-2-propenyl group and the like.
C2-8 haloalkynyl groups include 3-chloro-1-propynyl group, 3-chloro-1-butynyl group, 3-bromo-1-butynyl group, 3-bromo-2-propynyl group, 3-iodo-2 -Propynyl group and the like.
[ R4 ]
R4は、水素原子、C1~8アルキル基、無置換の若しくは置換基を有するC3~8シクロアルキル基、C2~8アルケニル基、C2~8アルキニル基、C1~8ハロアルキル基、C2~8ハロアルケニル基、またはC2~8ハロアルキニル基を表す。 [R 4]
R 4 represents a hydrogen atom, a C1-8 alkyl group, an unsubstituted or substituted C3-8 cycloalkyl group, a C2-8 alkenyl group, a C2-8 alkynyl group, a C1-8 haloalkyl group, a C2-8 halo. It represents an alkenyl group or a C2-8 haloalkynyl group.
R4は、水素原子、C1~8アルキル基、無置換の若しくは置換基を有するC3~8シクロアルキル基、C2~8アルケニル基、C2~8アルキニル基、C1~8ハロアルキル基、C2~8ハロアルケニル基、またはC2~8ハロアルキニル基を表す。 [R 4]
R 4 represents a hydrogen atom, a C1-8 alkyl group, an unsubstituted or substituted C3-8 cycloalkyl group, a C2-8 alkenyl group, a C2-8 alkynyl group, a C1-8 haloalkyl group, a C2-8 halo. It represents an alkenyl group or a C2-8 haloalkynyl group.
R4における、C1~8アルキル基としては、前記Xにおける、C1~8アルキル基として記述したものと同じものが挙げられる。
R4における、無置換の若しくは置換基を有するC3~8シクロアルキル基としては、前記R1などにおける、無置換の若しくは置換基を有するC3~8シクロアルキル基として記述したものと同じものが挙げられる。
R4における、C2~8アルケニル基、C2~8アルキニル基、C1~8ハロアルキル基、C2~8ハロアルケニル基、およびC2~8ハロアルキニル基としては、前記R3における、C2~8アルケニル基、C2~8アルキニル基、C1~8ハロアルキル基、C2~8ハロアルケニル基、およびC2~8ハロアルキニル基として記述したものと同じものが挙げられる。 Examples of the C1-8 alkyl group in R 4 include the same as those described as the C1-8 alkyl group in X.
Examples of the unsubstituted or substituted C3-8 cycloalkyl group in R 4 include the same as those described as the unsubstituted or substituted C3-8 cycloalkyl group in R 1 and the like. It is done.
In R 4 , the C2-8 alkenyl group, C2-8 alkynyl group, C1-8 haloalkyl group, C2-8 haloalkenyl group, and C2-8 haloalkynyl group include the C2-8 alkenyl group in R 3 , Examples thereof include those described as C2-8 alkynyl groups, C1-8 haloalkyl groups, C2-8 haloalkenyl groups, and C2-8 haloalkynyl groups.
R4における、無置換の若しくは置換基を有するC3~8シクロアルキル基としては、前記R1などにおける、無置換の若しくは置換基を有するC3~8シクロアルキル基として記述したものと同じものが挙げられる。
R4における、C2~8アルケニル基、C2~8アルキニル基、C1~8ハロアルキル基、C2~8ハロアルケニル基、およびC2~8ハロアルキニル基としては、前記R3における、C2~8アルケニル基、C2~8アルキニル基、C1~8ハロアルキル基、C2~8ハロアルケニル基、およびC2~8ハロアルキニル基として記述したものと同じものが挙げられる。 Examples of the C1-8 alkyl group in R 4 include the same as those described as the C1-8 alkyl group in X.
Examples of the unsubstituted or substituted C3-8 cycloalkyl group in R 4 include the same as those described as the unsubstituted or substituted C3-8 cycloalkyl group in R 1 and the like. It is done.
In R 4 , the C2-8 alkenyl group, C2-8 alkynyl group, C1-8 haloalkyl group, C2-8 haloalkenyl group, and C2-8 haloalkynyl group include the C2-8 alkenyl group in R 3 , Examples thereof include those described as C2-8 alkynyl groups, C1-8 haloalkyl groups, C2-8 haloalkenyl groups, and C2-8 haloalkynyl groups.
[ R5 ]
R5は、水素原子、C1~8アルキル基、アシル基、ホルミル基、C1~8アルコキシC1~8アルキル基、C2~8アシルオキシC1~8アルキル基、C1~8アルコキシカルボニル基、C1~8アルキルスルホニル基、または無置換の若しくは置換基を有するフェニルスルホニル基を表す。
R5におけるC1~8アルキル基としては、前記XにおけるC1~8アルキル基として記述したものと同じものが挙げられる。
アシル基としては、アセチル基、プロピオニル基、ピバロイル基、トリフルオロアセチル基、トリクロロアセチル基、ベンゾイル基、4-メチルベンゾイル基、2-クロロベンゾイル基などが挙げられる。
C1~8アルコキシC1~8アルキル基としては、メトキシメチル基、エトキシメチル基、i-プロポキシメチル基、1-メトキシエチル基、2-メトキシエチル基、1-エトキシエチル基、2-エトキシエチル基、1-メトキシ-n-プロピル基、2-メトキシ-n-プロピル基、3-メトキシ-n-プロピル基などが挙げられる。
C2~8アシルオキシC1~8アルキル基としては、アセトキシメチル基、アセトキシエチル基、プロポニルオキシメチル基、ピバロイルオキシメチル基、1-アセトキシエチル基、2-アセトキシエチル基、1-アセトキシ-n-プロピル基などが挙げられる。
C1~8アルコキシカルボニル基としては、メトキシカルボニル基、エトキシカルボニル基、イソプロポキシカルボニル基、n-ブトキシカルボニル基、t-ブトキシカルボニル基などを挙げられる。
C1~8アルキルスルホニル基としては、メチルスルホニル基、エチルスルホニル基、n-プロピルスルホニル基、i-プロピルスルホニル基などが挙げられる。
無置換の若しくは置換基を有するフェニルスルホニル基としては、フェニルスルホニル基、4-メチルフェニルスルホニル基、2-クロロフェニルスルホニル基、2,4-ジメチルフェニルスルホニル基などが挙げられる。 [R 5]
R 5 is a hydrogen atom, C1-8 alkyl group, acyl group, formyl group, C1-8 alkoxy C1-8 alkyl group, C2-8 acyloxy C1-8 alkyl group, C1-8 alkoxycarbonyl group, C1-8 alkyl A sulfonyl group or an unsubstituted or substituted phenylsulfonyl group is represented.
Examples of the C1-8 alkyl group for R 5 include the same as those described as the C1-8 alkyl group for X.
Examples of the acyl group include an acetyl group, a propionyl group, a pivaloyl group, a trifluoroacetyl group, a trichloroacetyl group, a benzoyl group, a 4-methylbenzoyl group, and a 2-chlorobenzoyl group.
C1-8 alkoxy C1-8 alkyl group includes methoxymethyl group, ethoxymethyl group, i-propoxymethyl group, 1-methoxyethyl group, 2-methoxyethyl group, 1-ethoxyethyl group, 2-ethoxyethyl group, Examples include 1-methoxy-n-propyl group, 2-methoxy-n-propyl group, 3-methoxy-n-propyl group and the like.
Examples of the C2-8 acyloxy C1-8 alkyl group include an acetoxymethyl group, an acetoxyethyl group, a propenyloxymethyl group, a pivaloyloxymethyl group, a 1-acetoxyethyl group, a 2-acetoxyethyl group, and a 1-acetoxy-n. -Propyl group and the like.
Examples of the C1-8 alkoxycarbonyl group include methoxycarbonyl group, ethoxycarbonyl group, isopropoxycarbonyl group, n-butoxycarbonyl group, t-butoxycarbonyl group and the like.
Examples of the C1-8 alkylsulfonyl group include a methylsulfonyl group, an ethylsulfonyl group, an n-propylsulfonyl group, and an i-propylsulfonyl group.
Examples of the unsubstituted or substituted phenylsulfonyl group include a phenylsulfonyl group, a 4-methylphenylsulfonyl group, a 2-chlorophenylsulfonyl group, and a 2,4-dimethylphenylsulfonyl group.
R5は、水素原子、C1~8アルキル基、アシル基、ホルミル基、C1~8アルコキシC1~8アルキル基、C2~8アシルオキシC1~8アルキル基、C1~8アルコキシカルボニル基、C1~8アルキルスルホニル基、または無置換の若しくは置換基を有するフェニルスルホニル基を表す。
R5におけるC1~8アルキル基としては、前記XにおけるC1~8アルキル基として記述したものと同じものが挙げられる。
アシル基としては、アセチル基、プロピオニル基、ピバロイル基、トリフルオロアセチル基、トリクロロアセチル基、ベンゾイル基、4-メチルベンゾイル基、2-クロロベンゾイル基などが挙げられる。
C1~8アルコキシC1~8アルキル基としては、メトキシメチル基、エトキシメチル基、i-プロポキシメチル基、1-メトキシエチル基、2-メトキシエチル基、1-エトキシエチル基、2-エトキシエチル基、1-メトキシ-n-プロピル基、2-メトキシ-n-プロピル基、3-メトキシ-n-プロピル基などが挙げられる。
C2~8アシルオキシC1~8アルキル基としては、アセトキシメチル基、アセトキシエチル基、プロポニルオキシメチル基、ピバロイルオキシメチル基、1-アセトキシエチル基、2-アセトキシエチル基、1-アセトキシ-n-プロピル基などが挙げられる。
C1~8アルコキシカルボニル基としては、メトキシカルボニル基、エトキシカルボニル基、イソプロポキシカルボニル基、n-ブトキシカルボニル基、t-ブトキシカルボニル基などを挙げられる。
C1~8アルキルスルホニル基としては、メチルスルホニル基、エチルスルホニル基、n-プロピルスルホニル基、i-プロピルスルホニル基などが挙げられる。
無置換の若しくは置換基を有するフェニルスルホニル基としては、フェニルスルホニル基、4-メチルフェニルスルホニル基、2-クロロフェニルスルホニル基、2,4-ジメチルフェニルスルホニル基などが挙げられる。 [R 5]
R 5 is a hydrogen atom, C1-8 alkyl group, acyl group, formyl group, C1-8 alkoxy C1-8 alkyl group, C2-8 acyloxy C1-8 alkyl group, C1-8 alkoxycarbonyl group, C1-8 alkyl A sulfonyl group or an unsubstituted or substituted phenylsulfonyl group is represented.
Examples of the C1-8 alkyl group for R 5 include the same as those described as the C1-8 alkyl group for X.
Examples of the acyl group include an acetyl group, a propionyl group, a pivaloyl group, a trifluoroacetyl group, a trichloroacetyl group, a benzoyl group, a 4-methylbenzoyl group, and a 2-chlorobenzoyl group.
C1-8 alkoxy C1-8 alkyl group includes methoxymethyl group, ethoxymethyl group, i-propoxymethyl group, 1-methoxyethyl group, 2-methoxyethyl group, 1-ethoxyethyl group, 2-ethoxyethyl group, Examples include 1-methoxy-n-propyl group, 2-methoxy-n-propyl group, 3-methoxy-n-propyl group and the like.
Examples of the C2-8 acyloxy C1-8 alkyl group include an acetoxymethyl group, an acetoxyethyl group, a propenyloxymethyl group, a pivaloyloxymethyl group, a 1-acetoxyethyl group, a 2-acetoxyethyl group, and a 1-acetoxy-n. -Propyl group and the like.
Examples of the C1-8 alkoxycarbonyl group include methoxycarbonyl group, ethoxycarbonyl group, isopropoxycarbonyl group, n-butoxycarbonyl group, t-butoxycarbonyl group and the like.
Examples of the C1-8 alkylsulfonyl group include a methylsulfonyl group, an ethylsulfonyl group, an n-propylsulfonyl group, and an i-propylsulfonyl group.
Examples of the unsubstituted or substituted phenylsulfonyl group include a phenylsulfonyl group, a 4-methylphenylsulfonyl group, a 2-chlorophenylsulfonyl group, and a 2,4-dimethylphenylsulfonyl group.
本発明においては、R1、R2、R3、R4およびR5がそれぞれ独立に水素原子またはC1~8アルキル基であることが好ましい。
In the present invention, it is preferable that R 1 , R 2 , R 3 , R 4 and R 5 are each independently a hydrogen atom or a C1-8 alkyl group.
[ Y、Z ]
Yは、酸素原子または硫黄原子を表す。
Zは、単結合、酸素原子、硫黄原子、またはNR6で示される基を表す。
R6は、水素原子、またはC1~8アルキル基を表す。R6におけるC1~8アルキル基としては、前記XにおけるC1~8アルキル基として記述したものと同じものが挙げられる。
本発明では、YおよびZが酸素原子であることが好ましい。 [Y, Z]
Y represents an oxygen atom or a sulfur atom.
Z represents a single bond, an oxygen atom, a sulfur atom, or a group represented by NR 6 .
R 6 represents a hydrogen atom or a C1-8 alkyl group. Examples of the C1-8 alkyl group for R 6 include the same as those described as the C1-8 alkyl group for X.
In the present invention, Y and Z are preferably oxygen atoms.
Yは、酸素原子または硫黄原子を表す。
Zは、単結合、酸素原子、硫黄原子、またはNR6で示される基を表す。
R6は、水素原子、またはC1~8アルキル基を表す。R6におけるC1~8アルキル基としては、前記XにおけるC1~8アルキル基として記述したものと同じものが挙げられる。
本発明では、YおよびZが酸素原子であることが好ましい。 [Y, Z]
Y represents an oxygen atom or a sulfur atom.
Z represents a single bond, an oxygen atom, a sulfur atom, or a group represented by NR 6 .
R 6 represents a hydrogen atom or a C1-8 alkyl group. Examples of the C1-8 alkyl group for R 6 include the same as those described as the C1-8 alkyl group for X.
In the present invention, Y and Z are preferably oxygen atoms.
[ Q ]
Qは、無置換の若しくは置換基を有するピラゾール環基を表す。該ピラゾール環基と、R1およびR2を有する炭素との結合位置は特に限定されない。Qは、無置換の若しくは置換基を有する1H-ピラゾール-3-イル基、無置換の若しくは置換基を有する2H-ピラゾール-3-イル基、または無置換の若しくは置換基を有する1H-ピラゾール-4-イル基であるのが好ましい。 [Q]
Q represents an unsubstituted or substituted pyrazole ring group. The bonding position of the pyrazole ring group and the carbon having R 1 and R 2 is not particularly limited. Q is an unsubstituted or substituted 1H-pyrazol-3-yl group, an unsubstituted or substituted 2H-pyrazol-3-yl group, or an unsubstituted or substituted 1H-pyrazol- A 4-yl group is preferred.
Qは、無置換の若しくは置換基を有するピラゾール環基を表す。該ピラゾール環基と、R1およびR2を有する炭素との結合位置は特に限定されない。Qは、無置換の若しくは置換基を有する1H-ピラゾール-3-イル基、無置換の若しくは置換基を有する2H-ピラゾール-3-イル基、または無置換の若しくは置換基を有する1H-ピラゾール-4-イル基であるのが好ましい。 [Q]
Q represents an unsubstituted or substituted pyrazole ring group. The bonding position of the pyrazole ring group and the carbon having R 1 and R 2 is not particularly limited. Q is an unsubstituted or substituted 1H-pyrazol-3-yl group, an unsubstituted or substituted 2H-pyrazol-3-yl group, or an unsubstituted or substituted 1H-pyrazol- A 4-yl group is preferred.
前記ピラゾール環基の置換基としては、ハロゲン原子、無置換の若しくは置換基を有するC1~8アルキル基、無置換の若しくは置換基を有するC2~8アルケニル基、無置換の若しくは置換基を有するC2~8アルキニル基、無置換の若しくは置換基を有するC1~8アルコキシ基、無置換の若しくは置換基を有するC1~8アルキルチオ基、無置換の若しくは置換基を有するC1~8アルキルスルホニル基、または無置換の若しくは置換基を有するC1~8アルキルスルホニルオキシ基などを挙げることができる。
Examples of the substituent of the pyrazole ring group include a halogen atom, an unsubstituted or substituted C1-8 alkyl group, an unsubstituted or substituted C2-8 alkenyl group, an unsubstituted or substituted C2 -8 alkynyl group, unsubstituted or substituted C1-8 alkoxy group, unsubstituted or substituted C1-8 alkylthio group, unsubstituted or substituted C1-8 alkylsulfonyl group, or unsubstituted Examples thereof include a substituted or substituted C1-8 alkylsulfonyloxy group.
ピラゾール環基の置換基におけるハロゲン原子、C1~8アルキル基、およびC1~8アルコキシ基としては、前記XまたはR1などにおける、ハロゲン原子、C1~8アルキル基、およびC1~8アルコキシ基として記述したものと同じものが挙げられる。
The halogen atom, C1-8 alkyl group, and C1-8 alkoxy group in the substituent of the pyrazole ring group are described as the halogen atom, C1-8 alkyl group, and C1-8 alkoxy group in the above X or R 1 etc. The same as
置換基を有するC1~8アルキル基としては、クロロメチル基、フルオロメチル基、トリフルオロメチル基、2,2,2-トリフルオロエチル基、2,2,2-トリフルオロ-1-メチルエチル基などのC1~8ハロアルキル基; シクロプロピルメチル基、シクロブチルメチル基、シクロプロピルエチル基などのC3~8シクロアルキルC1~8アルキル基; メトキシメチル基、エトキシメチル基、エトキシエチル基などのC1~8アルコキシC1~8アルキル基; シアノメチル基などのシアノC1~8アルキル基; ニトロメチル基などのニトロC1~8アルキル基; メチルチオメチル基、エチルチオメチル基などのC1~8アルキルチオC1~8アルキル基; ベンジル基、フェネチル基などのC6~10アリールC1~8アルキル基; アセチルオキシメチル基、プロピオニルオキシメチル基などのC1~7アシルオキシC1~8アルキル基; などが挙げられる。
Examples of the C1-8 alkyl group having a substituent include a chloromethyl group, a fluoromethyl group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group, and a 2,2,2-trifluoro-1-methylethyl group. C1-8 haloalkyl groups such as: C3-8 cycloalkyl C1-8 alkyl groups such as cyclopropylmethyl, cyclobutylmethyl, and cyclopropylethyl groups; C1-8 such as methoxymethyl, ethoxymethyl, and ethoxyethyl groups 8 alkoxy C1-8 alkyl group; cyano C1-8 alkyl group such as cyanomethyl group; nitro C1-8 alkyl group such as nitromethyl group; C1-8 alkylthio C1-8 alkyl group such as methylthiomethyl group, ethylthiomethyl group; C6-10 aryl such as benzyl group and phenethyl group Kill group; acetyloxymethyl group, C1 ~ 7 acyloxy C1 ~ 8 alkyl group such as propionyloxymethyl group; and the like.
ピラゾール環基の置換基におけるC2~8アルケニル基、およびC2~8アルキニル基としては、前記R3における、C2~8アルケニル基、およびC2~8アルキニル基として記述したものと同じものが挙げられる。
Examples of the C2-8 alkenyl group and C2-8 alkynyl group in the substituent of the pyrazole ring group include the same as those described as the C2-8 alkenyl group and C2-8 alkynyl group in R 3 .
C1~8アルキルチオ基としては、メチルチオ基、エチルチオ基、n-プロピルチオ基、i-プロピルチオ基、n-ブチルチオ基、i-ブチルチオ基、s-ブチルチオ基、t-ブチルチオ基などが挙げられる。
Examples of the C1-8 alkylthio group include methylthio group, ethylthio group, n-propylthio group, i-propylthio group, n-butylthio group, i-butylthio group, s-butylthio group, t-butylthio group and the like.
C1~8アルキルスルホニル基としては、メチルスルホニル基、エチルスルホニル基、i-プロピルスルホニル基、n-ブチルスルホニル基などが挙げられる。
Examples of the C1-8 alkylsulfonyl group include a methylsulfonyl group, an ethylsulfonyl group, an i-propylsulfonyl group, and an n-butylsulfonyl group.
C1~8アルキルスルホニルオキシ基としては、メチルスルホニルオキシ基、エチルスルホニルオキシ基、i-プロピルスルホニルオキシ基、n-ブチルスルホニルオキシ基などが挙げられる。
Examples of the C1-8 alkylsulfonyloxy group include a methylsulfonyloxy group, an ethylsulfonyloxy group, an i-propylsulfonyloxy group, and an n-butylsulfonyloxy group.
本発明化合物の中で、特に好ましい化合物は、式(I)で表されるオキシムエーテル誘導体またはその塩において、XがC1~8アルキル基であり、R1、R2、R3、R4およびR5がそれぞれ独立に水素原子またはC1~8アルキル基であり、YおよびZが酸素原子であり、Qが無置換の若しくは置換基を有する1H-ピラゾール-3-イル基、無置換の若しくは置換基を有する2H-ピラゾール-3-イル基、または無置換の若しくは置換基を有する1H-ピラゾール-4-イル基であり、mが1であり、且つnが0~1であるものである。
Among the compounds of the present invention, particularly preferred compounds are those in which the oxime ether derivative represented by the formula (I) or a salt thereof, wherein X is a C1-8 alkyl group, R 1 , R 2 , R 3 , R 4 and R 5 is independently a hydrogen atom or a C1-8 alkyl group, Y and Z are oxygen atoms, Q is unsubstituted or substituted 1H-pyrazol-3-yl group, unsubstituted or substituted A 2H-pyrazol-3-yl group having a group or an 1H-pyrazol-4-yl group having no substituent or a substituent, wherein m is 1 and n is 0 to 1.
本発明のオキシムエーテル誘導体には、炭素-窒素二重結合に基づく幾何異性体(シス-トランス異性体)が存在し得るが、これらの異性体はすべて本発明に含まれる。
In the oxime ether derivative of the present invention, geometric isomers based on carbon-nitrogen double bonds (cis-trans isomers) may exist, and all of these isomers are included in the present invention.
本発明化合物であるオキシムエーテル誘導体の塩は、化学的に許容される塩であれば、特に制限されない。例えば、リチウム、ナトリウム、カリウムなどのアルカリ金属の塩;カルシウム、マグネシウムなどのアルカリ土類金属の塩;鉄、銅などの遷移金属の塩;アンモニア、トリエチルアミン、トリブチルアミン、ピリジン、ヒドラジンなどの有機塩基の塩;などが挙げられる。
The salt of the oxime ether derivative that is the compound of the present invention is not particularly limited as long as it is a chemically acceptable salt. For example, salts of alkali metals such as lithium, sodium and potassium; salts of alkaline earth metals such as calcium and magnesium; salts of transition metals such as iron and copper; organic bases such as ammonia, triethylamine, tributylamine, pyridine and hydrazine And the like.
本発明化合物は、広範囲の種類の糸状菌、例えば、藻菌類(Oomycetes)、子嚢菌類(Ascomycetes),不完全菌類(Deuteromycetes)、担子菌類(Basidiomycetes)に属する菌に対し優れた殺菌力を有するので、農園芸用殺菌剤の有効成分として有用である。
The compound of the present invention has an excellent bactericidal activity against a wide variety of filamentous fungi, for example, bacteria belonging to algae fungi (Oomycetes), ascomycetes (Ascomycetes), imperfect fungi (Deuteromycetes), basidiomycetes (Basidiomycetes) Therefore, it is useful as an active ingredient of agricultural and horticultural fungicides.
本発明化合物は、公知の方法、例えば特許文献3に記載の方法に準拠して、工業的に容易に製造することができる。製造された化合物の構造は、IRスペクトル、NMRスペクトル、マススペクトル、元素分析などの公知の分析手段により、同定、確認することができる。
The compound of the present invention can be easily produced industrially in accordance with a known method, for example, the method described in Patent Document 3. The structure of the produced compound can be identified and confirmed by known analytical means such as IR spectrum, NMR spectrum, mass spectrum, and elemental analysis.
本発明化合物としては、具体的に例えば、表(1)~表(3)に示す化合物が挙げられる。但し、表(1)~表(3)の化合物は例示のためのものであって、本発明化合物はこれによってこれらのみに限定されるものではない。
なお、表中の、Etはエチル基を、iPrはイソプロピル基を、nBuはn-ブチル基を、sBuはs-ブチル基を、tBuはt-ブチル基を、cPrはシクロプロピル基を、Acはアセチル基を、それぞれ表す。 Specific examples of the compound of the present invention include compounds shown in Tables (1) to (3). However, the compounds in Tables (1) to (3) are for illustrative purposes, and the compounds of the present invention are not limited thereto.
In the table, Et represents an ethyl group, i Pr represents an isopropyl group, n Bu represents an n-butyl group, s Bu represents a s-butyl group, t Bu represents a t-butyl group, and c Pr represents a cyclo A propyl group and Ac represents an acetyl group, respectively.
なお、表中の、Etはエチル基を、iPrはイソプロピル基を、nBuはn-ブチル基を、sBuはs-ブチル基を、tBuはt-ブチル基を、cPrはシクロプロピル基を、Acはアセチル基を、それぞれ表す。 Specific examples of the compound of the present invention include compounds shown in Tables (1) to (3). However, the compounds in Tables (1) to (3) are for illustrative purposes, and the compounds of the present invention are not limited thereto.
In the table, Et represents an ethyl group, i Pr represents an isopropyl group, n Bu represents an n-butyl group, s Bu represents a s-butyl group, t Bu represents a t-butyl group, and c Pr represents a cyclo A propyl group and Ac represents an acetyl group, respectively.
(2)農園芸用殺菌剤
本発明殺菌剤は、本発明化合物から選ばれる少なくとも1種を有効成分として含有するものである。 (2) Agricultural and horticultural fungicide The fungicide of the present invention contains at least one selected from the compounds of the present invention as an active ingredient.
本発明殺菌剤は、本発明化合物から選ばれる少なくとも1種を有効成分として含有するものである。 (2) Agricultural and horticultural fungicide The fungicide of the present invention contains at least one selected from the compounds of the present invention as an active ingredient.
本発明殺菌剤は、本発明化合物と同様に、広範囲の種類の糸状菌、例えば、藻菌類(Oomycetes)、子嚢菌類(Ascomycetes),不完全菌類(Deuteromycetes)、担子菌類(Basidiomycetes)に属する菌に対し優れた殺菌力を有する。
The fungicides of the present invention, like the compounds of the present invention, are bacteria belonging to a wide variety of fungi, for example, algae fungi (Oomycetes), ascomycetes (Ascomycetes), incomplete fungi (Deuteromycetes), basidiomycetes (Basidiomycetes) Excellent sterilizing power.
本発明殺菌剤は、花卉、芝、牧草を含む農園芸作物の栽培に際し発生する種々の病害の防除に、種子処理、茎葉散布、土壌施用または水面施用などの手段を用いることにより使用することができる。
The fungicide of the present invention can be used by using means such as seed treatment, foliage spraying, soil application or water surface application for the control of various diseases that occur during cultivation of agricultural and horticultural crops including flower buds, turf and grass. it can.
例えば、「テンサイ」の褐斑病(Cercospora beticola); 「ラッカセイ」の褐斑病(Mycosphaerella arachidis)、黒渋病(Mycosphaerella berkeleyi); 「キュウリ」のうどんこ病(Sphaerotheca fuliginea)、つる枯病(Mycosphaerella melonis)、菌核病(Sclerotinia sclerotiorum)、灰色かび病(Botrytis cinerea)、黒星病(Cladosporium cucumerinum)、褐斑病(Corynespora cassicola)、苗立枯病(Pythium debaryanam、Rhizoctonia solani Kuhn)、斑点細菌病(Pseudomonas syringae pv.Lecrymans); 「トマト」の灰色かび病(Botrytis cinerea)、葉かび病(Cladosporium fulvum); 「ナス」の灰色かび病(Botrytis cinerea)、黒枯病(Corynespora melongenae)、うどんこ病(Erysiphe cichoracearum)、すすかび病(Mycovellosiella nattrassii); 「イチゴ」の灰色かび病(Botrytis cinerea)、うどんこ病(Sohaerotheca humuli)、炭そ病(Colletotrichum acutatum、Colletotrichum fragariae); 「タマネギ」の灰色腐敗病(Botrytis allii)、灰色かび病(Botrytis cinerea)、白斑葉枯病(Botrytis squamosa); 「キャベツ」の根こぶ病(Plasmodiophora brassicae)、軟腐病(Erwinia carotovora); 「インゲン」の菌核病(Sclerotinia sclerotiorum)、灰色かび病(Botrytis cinerea); 「りんご」のうどんこ病(Podosphaera leucotricha)、黒星病(Venturia inaequalis)、モニリア病(Monilinia mali)、腐らん病(Valsa mali)、斑点落葉病(Alternaria mali)、赤星病(Gymnosporangium yamadae)、輪紋病(Botryosphaeria berengeriana)、炭そ病(Colletotrichum gloeosprioides)、褐斑病(Diplocarpon mali); 「カキ」のうどんこ病(Phyllactinia kakicola)、炭そ病(Gloeosporium kaki)、角斑落葉病(Cercospora kaki); 「モモ・オウトウ」の灰星病(Monilinia fructicola); 「ブドウ」の灰色かび病(Botrytis cinerea)、うどんこ病(Uncinula necator)、晩腐病(Glomerella cingulata); 「ナシ」の黒星病(Venturia nashicola)、赤星病(Gymnosporangium asiaticum)、黒斑病(Alternaria kikuchiana); 「チャ」の輪斑病(Pestalotia theae)、炭そ病(Colletotrichum theae-sinensis); 「カンキツ」のそうか病(Elsinoe fawcetti)、青かび病(Penicillium italicum)、緑かび病(Penicillium digitatum)、灰色かび病(Botrytis cinerea)、黒点病(Diaporthe citri)、かいよう病(Xanthomonas campestris pv.Citri); 「コムギ」のうどんこ病(Erysiphe graminis f.sp.tritici)、赤かび病(Gibberella zeae)、赤さび病(Puccinia recondita)、褐色雪腐病(Pythium iwayamai)、紅色雪腐病(Monographella nivalis)、眼紋病(Pseudocercosporella herpotrichoides)、葉枯病(Septoria tritici)、ふ枯病(Leptosphaeria nodorum)、雪腐小粒菌核病(Typhula incarnata)、雪腐大粒菌核病(Myriosclerotinia borealis)、立枯病(Gaeumanomyces graminis); 「オオムギ」の斑葉病(Pyrenophora graminea)、雲形病(Rhynchosporium secalis)、裸黒穂病(Ustilago tritici、U.nuda); 「イネ」のいもち病(Pyricularia oryzae)、紋枯病(Rhizoctonia solani)、馬鹿苗病(Gibberella fujikuroi)、ごま葉枯病(Cochliobolus niyabeanus); 「タバコ」の菌核病(Sclerotinia sclerotiorum)、うどんこ病(Erysiphe cichoracearum); 「チューリップ」の灰色かび病(Botrytis cinerea); 「ベントグラス」の雪腐大粒菌核病(Sclerotinia borealis); 「オーチャードグラス」のうどんこ病(Erysiphe graminis); 「ダイズ」の紫斑病(Cercospora kikuchii); 「ジャガイモ・トマト」の疫病(Phytophthora infestans); 「キュウリ」のべと病(Pseudoperonospora cubensis); 「ブドウ」のべと病(Plasmopara viticola)などの、花卉、芝、牧草を含む農園芸作物の栽培で発生する種々の病害の防除に使用することができる。
For example, “sugar beet” brown spot (Cercospora beticola); “peanut” brown spot (Mycosphaerella arachidis); black astringency (Mycosphaerella berkeleyi); “cucumber” powdery mildew (Sphaerotheca fuliginea), vine blight ( Mycosphaerella melonis), Mycorrhizal disease (Sclerotiniainsclerotiorum), Gray mold disease (Botrytis cinerea), Black spot disease (Cladosporium cucumerinum), Brown spot disease (Corynespora cassicola), Seedling disease (Pythium debaryanam, Rhizoctonia solani Kuhn) Disease (Pseudomonas syringae pv.Lecrymans); “Tomato” gray mold (Botrytis cinerea), leaf mold (Cladosporium fulvum); “Nasal” gray mold (Botrytis cinerea), black blight (Corynespora melongenae), powdery mildew Mildew (Erysiphe cichoracearum), mildew (Mycovellosiella nattrassii); “strawberry” gray mold (Botrytis cinerea), powdery mildew (Sohaerotheca humuli) , Anthracnose (Colletotrichum acutatum, Colletotrichumariafragariae); gray rot of onion (Botrytis allii), gray mold (Botrytis cinerea), leafy blight (Botrytis squamosa); brassicae), soft rot (Erwinia carotovora); ”carrot nuclei (Sclerotinia sclerotiorum)”, gray mold (Botrytis cinerea); “apple” powdery mildew (Podosphaera leucotricha), black scab (Venturia inaequalis), monilia Disease (Monilinia mali), rot disease (Valsa mali), spotted leaf disease (Alternaria mali), red star disease (Gymnosporangium yamadae), ring rot (Botryosphaeria berengeriana), anthracnose disease (Colletotrichum gloeosprioides), brown spot disease (Diplocarpon) ); “Oyster” powdery mildew (Phyllactinia kakicola), anthracnose (Gloeosporium kaki), keratodeciduous leaf disease (Cercospora kaki); “peach sweet cherry” ash Disease (Monilinia fructicola); “Grape” gray mold disease (Botrytis cinerea), powdery mildew (Uncinula necator), late rot (Glomerella cingulata); “pear” black star disease (Venturia nashicola), red star disease (Gymnosporangium asiaticum) ), Black spot disease (Alternaria kikuchiana); “cha” ring spot disease (Pestalotia theae), anthracnose disease (Colletotrichum theae-sinensis); “citrus” scab (Elsinoe fawcetti), blue mold disease (Penicillium italicum) , Green mold disease (Penicillium digitatum), gray mold disease (Botrytis cinerea), black spot disease (Diaporthe citri), scab (Xanthomonas campestris pv. Citri); “wheat” powdery mildew (Erysiphe graminis f. Sp. Tritici) , Red mold (Gibberella zeae), red rust (Puccinia recondita), brown snow rot (Pythium iwayamai), red snow rot (Monographella nivalis), eye spot disease (Pseudocercosporella herpotrichoides), leaf blight (Septoria tritici), dry blight (Leptosphaeria nodorum), snowy rot micronucleus nuclear disease (Typhula incarnata), snow rot large mycobacterial disease (Myriosclerotinia borealis), blight (Gaeumanomyces graminis); (Pyrenophora graminea), cloud disease (Rhynchosporium secalis), naked scab (Ustilago tritici, U.nuda); rice blast (Pyricularia oryzae), blight (Rhizoctonia solani), idiotic seedling (Gibberella fujikuroi) , Sesame leaf blight (Cochliobolus niyabeanus); “Tobacco” sclerotia (Sclerotinia sclerotiorum), powdery mildew (Erysiphe cichoracearum); “Tulip” gray mold (Botrytis cinerea); Nuclear disease (Sclerotinia borealis); “Orchardgrass” powdery mildew (Erysiphe graminis); “Soybean” purpura (Cercospora kikuchii); “Potato tomato” plague (Ph ytophthora infestans); “cucumber” downy mildew (Pseudoperonospora cubensis); “grape” downy mildew (Plasmopara viticola), etc. to control various diseases that occur in the cultivation of agro-horticultural crops including flowers, turf and grass Can be used for
また、本発明の殺菌剤は、ベンズイミダゾール系殺菌剤やジカルボキシイミド系殺菌剤などの従来の殺菌剤に対して耐性を有するようになった菌に対しても優れた殺菌効果を有する。係る耐性菌としては、チオファネートメチル、ベノミル、カルベンダジムなどのベンズイミダゾール系殺菌剤に耐性を示す灰色かび病菌(Botrytis cinerea)やテンサイ褐斑病菌(Cercospora beticola)、リンゴ黒星病菌(Venturia inaequalis)、ナシ黒星病菌(Venturia nashicola);ジカルボキシイミド系殺菌剤(例えば、ビンクロゾリン、プロシミドン、イプロジオン)に耐性を示す灰色かび病菌(Botrytis cinerea)などが挙げられる。
In addition, the bactericidal agent of the present invention has an excellent bactericidal effect against bacteria that have become resistant to conventional bactericides such as benzimidazole bactericides and dicarboximide fungicides. As such resistant bacteria, gray mold fungus (Botrytis cinerea), sugar beet brown fungus (Cercospora beticola), apple black rot fungus (Venturia inaequalis), pear black star that show resistance to benzimidazole fungicides such as thiophanate methyl, benomyl, and carbendazim Examples include Venturia nashicola; gray mold fungus (Botrytis cinerea) that is resistant to dicarboximide fungicides (for example, vinclozolin, procymidone, iprodione).
本発明殺菌剤の適用が好ましい病害としては、テンサイの褐斑病、コムギのうどんこ病、イネのいもち病、リンゴ黒星病、キュウリの灰色かび病、ラッカセイの褐斑病などが挙げられる。また本発明殺菌剤は薬害が少なく、魚類や温血動物への毒性が低く、安全性の高い薬剤である。
Favorable diseases to which the fungicide of the present invention is applied include sugar beet brown spot, wheat powdery mildew, rice blast, apple black spot, cucumber gray mold, peanut brown spot and the like. The fungicide of the present invention is a highly safe drug with little phytotoxicity, low toxicity to fish and warm-blooded animals.
本発明殺菌剤は、一般の農薬のとり得る形態、即ち、水和剤、粒剤、粉剤、乳剤、水溶剤、懸濁剤、顆粒水和剤などの農薬製剤の形態で使用するものであってもよい。
The fungicide of the present invention is used in a form that can be taken by general agricultural chemicals, that is, in the form of agrochemical preparations such as wettable powders, granules, powders, emulsions, aqueous solvents, suspensions, and wettable granules. May be.
固形の製剤とする場合に使用する添加剤及び担体としては、大豆粉、小麦粉などの植物性粉末、珪藻土、燐灰石、石こう、タルク、ベントナイト、パイロフィライト、クレーなどの鉱物性微粉末、安息香酸ソーダ、尿素、芒硝などの有機及び無機化合物が挙げられる。
Additives and carriers used for solid preparations include vegetable powders such as soybean flour and wheat flour, mineral fine powders such as diatomaceous earth, apatite, gypsum, talc, bentonite, pyrophyllite and clay, benzoic acid Organic and inorganic compounds such as soda, urea and mirabilite can be mentioned.
液体の製剤とする場合に使用する溶剤としては、ケロシン、キシレン及び石油系の芳香族炭化水素、シクロヘキサン、シクロヘキサノン、ジメチルホルムアミド、ジメチルスルホキシド、アルコール、アセトン、トリクロロエチレン、メチルイソブチルケトン、鉱物油、植物油、水などが挙げられる。
Solvents used for liquid formulations include kerosene, xylene and petroleum aromatic hydrocarbons, cyclohexane, cyclohexanone, dimethylformamide, dimethyl sulfoxide, alcohol, acetone, trichloroethylene, methyl isobutyl ketone, mineral oil, vegetable oil, Water etc. are mentioned.
これらの製剤には、均一かつ安定な形態をとるために、必要に応じ界面活性剤を添加することができる。
添加することができる界面活性剤としては特に限定はないが、例えば、ポリオキシエチレンが付加したアルキルフェニルエーテル、ポリオキシエチレンが付加したアルキルエーテル、ポリオキシエチレンが付加した高級脂肪酸エステル、ポリオキシエチレンが付加したソルビタン高級脂肪酸エステル、ポリオキシエチレンが付加したトリスチリルフェニルエーテルなどの非イオン性界面活性剤、ポリオキシエチレンが付加したアルキルフェニルエーテルの硫酸エステル塩、アルキルベンゼンスルホン酸塩、高級アルコールの硫酸エステル塩、アルキルナフタレンスルホン酸塩、ポリカルボン酸塩、リグニンスルホン酸塩、アルキルナフタレンスルホン酸塩のホルムアルデヒド縮合物、イソブチレン-無水マレイン酸共重合体などが挙げられる。 In these preparations, a surfactant can be added as necessary in order to take a uniform and stable form.
The surfactant that can be added is not particularly limited. For example, alkylphenyl ether added with polyoxyethylene, alkyl ether added with polyoxyethylene, higher fatty acid ester added with polyoxyethylene, polyoxyethylene Sorbitan higher fatty acid ester added with polyoxyethylene, nonionic surfactant such as tristyryl phenyl ether added with polyoxyethylene, sulfate ester salt of alkylphenyl ether added with polyoxyethylene, alkylbenzene sulfonate, sulfuric acid of higher alcohol Examples include ester salts, alkyl naphthalene sulfonates, polycarboxylates, lignin sulfonates, formaldehyde condensates of alkyl naphthalene sulfonates, and isobutylene-maleic anhydride copolymers.
添加することができる界面活性剤としては特に限定はないが、例えば、ポリオキシエチレンが付加したアルキルフェニルエーテル、ポリオキシエチレンが付加したアルキルエーテル、ポリオキシエチレンが付加した高級脂肪酸エステル、ポリオキシエチレンが付加したソルビタン高級脂肪酸エステル、ポリオキシエチレンが付加したトリスチリルフェニルエーテルなどの非イオン性界面活性剤、ポリオキシエチレンが付加したアルキルフェニルエーテルの硫酸エステル塩、アルキルベンゼンスルホン酸塩、高級アルコールの硫酸エステル塩、アルキルナフタレンスルホン酸塩、ポリカルボン酸塩、リグニンスルホン酸塩、アルキルナフタレンスルホン酸塩のホルムアルデヒド縮合物、イソブチレン-無水マレイン酸共重合体などが挙げられる。 In these preparations, a surfactant can be added as necessary in order to take a uniform and stable form.
The surfactant that can be added is not particularly limited. For example, alkylphenyl ether added with polyoxyethylene, alkyl ether added with polyoxyethylene, higher fatty acid ester added with polyoxyethylene, polyoxyethylene Sorbitan higher fatty acid ester added with polyoxyethylene, nonionic surfactant such as tristyryl phenyl ether added with polyoxyethylene, sulfate ester salt of alkylphenyl ether added with polyoxyethylene, alkylbenzene sulfonate, sulfuric acid of higher alcohol Examples include ester salts, alkyl naphthalene sulfonates, polycarboxylates, lignin sulfonates, formaldehyde condensates of alkyl naphthalene sulfonates, and isobutylene-maleic anhydride copolymers.
このようにして得られた水和剤、乳剤、フロアブル剤、水溶剤、顆粒水和剤は水で所定の濃度に希釈して、溶解液、懸濁液あるいは乳濁液の形態で植物に散布する方法で使用される。また、粉剤・粒剤はそのまま植物に散布する方法で使用される。
The wettable powder, emulsion, flowable powder, aqueous solvent and granular wettable powder thus obtained are diluted with water to a predetermined concentration and sprayed on plants in the form of a solution, suspension or emulsion. Used in the way. Powders and granules are used as they are sprayed on plants.
本発明殺菌剤中における有効成分量は、通常、製剤全体に対して、好ましくは0.01~90重量%、より好ましくは0.05~85重量%である。
The amount of the active ingredient in the fungicide of the present invention is usually preferably 0.01 to 90% by weight, more preferably 0.05 to 85% by weight, based on the whole preparation.
本発明殺菌剤の施用量は、気象条件、製剤形態、施用磁気、施用方法、施用場所、防除対象病害、対象作物などにより異なるが、通常1ヘクタール当たり有効成分化合物量にして1~1,000g、好ましくは10~100gである。
The application amount of the fungicide of the present invention varies depending on weather conditions, formulation form, application magnetism, application method, application place, disease to be controlled, target crop, etc., but usually 1 to 1,000 g of active ingredient compound per hectare, 10 to 100 g is preferred.
水和剤、乳剤、懸濁剤、水溶剤、顆粒水和剤などを水で希釈して施用する場合、その施用濃度は1~1000ppm、好ましくは10~250ppmである。
When a wettable powder, emulsion, suspension, aqueous solvent, granular wettable powder or the like is diluted with water and applied, the applied concentration is 1 to 1000 ppm, preferably 10 to 250 ppm.
本発明殺菌剤には、本発明化合物のほかに、他の殺菌剤、殺虫・殺ダニ剤、共力剤などを混合することもできる。
In addition to the compounds of the present invention, other fungicides, insecticides / acaricides, synergists and the like can also be mixed with the fungicides of the present invention.
混合して使用できる他の殺菌剤、殺虫剤、殺ダニ剤、植物生長調節剤の代表例を以下に示す。
Typical examples of other fungicides, insecticides, acaricides, and plant growth regulators that can be used in combination are shown below.
殺菌剤:
キャプタン、フォルペット、チウラム、ジラム、ジネブ、マンネブ、マンコゼブ、プロピネブ、ポリカーバメート、クロロタロニル、キントーゼン、キャプタホル、イプロジオン、プロサイミドン、ビンクロゾリン、フルオロイミド、サイモキサニル、メプロニル、フルトラニル、ペンシクロン、オキシカルボキシン、ホセチルアルミニウム、プロパモカーブ、トリアジメホン、トリアジメノール、プロピコナゾール、ジクロブトラゾール、ビテルタノール、ヘキサコナゾール、マイクロブタニル、フルシラゾール、メトコナゾール、エタコナゾール、フルオトリマゾール、シプロコナゾール、エポキシコナゾール、フルトリアフェン、ベンコナゾール、ジニコナゾール、サイプロコナゾーズ、フェナリモール、トリフルミゾール、プロクロラズ、イマザリル、ペフラゾエート、トリデモルフ、フェンプロピモルフ、トリホリン、ブチオベート、ピリフェノックス、アニラジン、ポリオキシン、メタラキシル、オキサジキシル、フララキシル、イソプロチオラン、プロベナゾール、ピロールニトリン、ブラストサイジンS、カスガマイシン、バリダマイシン、硫酸ジヒドロストレプトマイシン、ベノミル、カルベンダジム、チオファネートメチル、ヒメキサゾール、塩基性塩化銅、塩基性硫酸銅、フェンチンアセテート、水酸化トリフェニル錫、ジエトフェンカルブ、メタスルホカルブ、キノメチオナート、ビナパクリル、レシチン、重曹、ジチアノン、ジノカップ、フェナミノスルフ、ジクロメジン、グアザチン、ドジン、IBP、エディフェンホス、メパニピリム、フェルムゾン、トリクラミド、メタスルホカルブ、フルアジナム、エトキノラック、ジメトモルフ、ピロキロン、テクロフタラム、フサライド、フェナジンオキシド、チアベンダゾール、トリシクラゾール、ビンクロゾリン、シモキサニル、シクロブタニル、グアザチン、プロパモカルブ塩酸塩、オキソリニック酸、ヒドロキシイソオキサゾール、イミノクタジン酢酸塩など。 Fungicide:
Captan, phorpet, thiuram, ziram, dineb, manneb, mancozeb, propineb, polycarbamate, chlorothalonil, quintosen, captaphor, iprodione, prosaimidin, vinclozolin, fluoroimide, thymoxanyl, mepronil, flutolanil, pencyclon, oxycarboxyl, fosetyl aluminum, Propamocurve, triadimephone, triadimenol, propiconazole, diclobutrazole, viteltanol, hexaconazole, microbutanyl, flusilazole, metconazole, etaconazole, fluotrimazole, cyproconazole, epoxyconazole, flutriaphene, beconazole , Diniconazole, cyproconazole, phenalimol, triflumizole, prochlor , Imazalyl, pefrazoate, tridemorph, fenpropimorph, triphorin, butiobate, pyrifenox, anilazine, polyoxin, metalaxyl, oxadixyl, furalaxyl, isoprothiolane, probenazole, pyrrolnitrin, blasticidin S, kasugamycin, validamycin, dihydrostreptomycin sulfate , Benomyl, carbendazim, thiophanate methyl, hymexazole, basic copper chloride, basic copper sulfate, fentin acetate, triphenyltin hydroxide, dietofencarb, metasulfocarb, quinomethionate, binapacryl, lecithin, baking soda, dithianon, dinocup, phenaminosulfur, Dichromemedin, guazatine, dodin, IBP, edifenphos, mepanipyrim, fermzone, Rikuramido, methasulfocarb, fluazinam, Etokinorakku, dimethomorph, pyroquilon, tecloftalam, fthalide, phenazine oxide, thiabendazole, tricyclazole, vinclozolin, cymoxanil, cyclobutanyl, guazatine, propamocarb hydrochloride, oxolinic acid, hydroxy isoxazole, etc. iminoctadine acetate.
キャプタン、フォルペット、チウラム、ジラム、ジネブ、マンネブ、マンコゼブ、プロピネブ、ポリカーバメート、クロロタロニル、キントーゼン、キャプタホル、イプロジオン、プロサイミドン、ビンクロゾリン、フルオロイミド、サイモキサニル、メプロニル、フルトラニル、ペンシクロン、オキシカルボキシン、ホセチルアルミニウム、プロパモカーブ、トリアジメホン、トリアジメノール、プロピコナゾール、ジクロブトラゾール、ビテルタノール、ヘキサコナゾール、マイクロブタニル、フルシラゾール、メトコナゾール、エタコナゾール、フルオトリマゾール、シプロコナゾール、エポキシコナゾール、フルトリアフェン、ベンコナゾール、ジニコナゾール、サイプロコナゾーズ、フェナリモール、トリフルミゾール、プロクロラズ、イマザリル、ペフラゾエート、トリデモルフ、フェンプロピモルフ、トリホリン、ブチオベート、ピリフェノックス、アニラジン、ポリオキシン、メタラキシル、オキサジキシル、フララキシル、イソプロチオラン、プロベナゾール、ピロールニトリン、ブラストサイジンS、カスガマイシン、バリダマイシン、硫酸ジヒドロストレプトマイシン、ベノミル、カルベンダジム、チオファネートメチル、ヒメキサゾール、塩基性塩化銅、塩基性硫酸銅、フェンチンアセテート、水酸化トリフェニル錫、ジエトフェンカルブ、メタスルホカルブ、キノメチオナート、ビナパクリル、レシチン、重曹、ジチアノン、ジノカップ、フェナミノスルフ、ジクロメジン、グアザチン、ドジン、IBP、エディフェンホス、メパニピリム、フェルムゾン、トリクラミド、メタスルホカルブ、フルアジナム、エトキノラック、ジメトモルフ、ピロキロン、テクロフタラム、フサライド、フェナジンオキシド、チアベンダゾール、トリシクラゾール、ビンクロゾリン、シモキサニル、シクロブタニル、グアザチン、プロパモカルブ塩酸塩、オキソリニック酸、ヒドロキシイソオキサゾール、イミノクタジン酢酸塩など。 Fungicide:
Captan, phorpet, thiuram, ziram, dineb, manneb, mancozeb, propineb, polycarbamate, chlorothalonil, quintosen, captaphor, iprodione, prosaimidin, vinclozolin, fluoroimide, thymoxanyl, mepronil, flutolanil, pencyclon, oxycarboxyl, fosetyl aluminum, Propamocurve, triadimephone, triadimenol, propiconazole, diclobutrazole, viteltanol, hexaconazole, microbutanyl, flusilazole, metconazole, etaconazole, fluotrimazole, cyproconazole, epoxyconazole, flutriaphene, beconazole , Diniconazole, cyproconazole, phenalimol, triflumizole, prochlor , Imazalyl, pefrazoate, tridemorph, fenpropimorph, triphorin, butiobate, pyrifenox, anilazine, polyoxin, metalaxyl, oxadixyl, furalaxyl, isoprothiolane, probenazole, pyrrolnitrin, blasticidin S, kasugamycin, validamycin, dihydrostreptomycin sulfate , Benomyl, carbendazim, thiophanate methyl, hymexazole, basic copper chloride, basic copper sulfate, fentin acetate, triphenyltin hydroxide, dietofencarb, metasulfocarb, quinomethionate, binapacryl, lecithin, baking soda, dithianon, dinocup, phenaminosulfur, Dichromemedin, guazatine, dodin, IBP, edifenphos, mepanipyrim, fermzone, Rikuramido, methasulfocarb, fluazinam, Etokinorakku, dimethomorph, pyroquilon, tecloftalam, fthalide, phenazine oxide, thiabendazole, tricyclazole, vinclozolin, cymoxanil, cyclobutanyl, guazatine, propamocarb hydrochloride, oxolinic acid, hydroxy isoxazole, etc. iminoctadine acetate.
殺虫・殺ダニ剤:
有機燐およびカーバメート系殺虫剤:
フェンチオン、フェニトロチオン、ダイアジノン、クロルピリホス、ESP、バミドチオン、フェントエート、ジメトエート、ホルモチオン、マラソン、トリクロルホン、チオメトン、ホスメット、ジクロルボス、アセフェート、EPBP、メチルパラチオン、オキシジメトンメチル、エチオン、サリチオン、シアノホス、イソキサチオン、ピリダフェンチオン、ホサロン、メチダチオン、スルプロホス、クロルフェンビンホス、テトラクロルビンホス、ジメチルビンホス、プロパホス、イソフェンホス、エチルチオメトン、プロフェノホス、ピラクロホス、モノクロトホス、アジンホスメチル、アルディカルブ、メソミル、チオジカルブ、カルボフラン、カルボスルファン、ベンフラカルブ、フラチオカルブ、プロポキスル、BPMC、MTMC、MIPC、カルバリル、ピリミカーブ、エチオフェンカルブ、フェノキシカルブ、EDDPなど。 Insecticides and acaricides:
Organophosphorus and carbamate insecticides:
Fenthion, Fenitrothion, Diazinon, Chlorpyrifos, ESP, Bamidthione, Fentoate, Dimethoate, Formothion, Marathon, Trichlorfone, Thiomethone, Phosmet, Dichlorvos, Acephate, EPBP, Methyl parathion, Oxydimethone methyl, Ethion, Salicione, Cyanophos, Fenthion, Salon Methidathione, Sulprophos, Chlorfenvinphos, Tetrachlorbinphos, Dimethylvinphos, Propafos, Isophenphos, Ethylthiomethone, Profenofos, Piracrofos, Monocrotophos, Adinfosmethyl, Aldicarb, Mesomil, Thiodicarb, Carbofuran, Carbosulfan, Benhracarb, Furatiocarb Propoxyl, BPMC, MTMC, MIPC, Kalbarri Le, Pirimi curve, Ethiophene carb, Phenoxy carb, EDDP.
有機燐およびカーバメート系殺虫剤:
フェンチオン、フェニトロチオン、ダイアジノン、クロルピリホス、ESP、バミドチオン、フェントエート、ジメトエート、ホルモチオン、マラソン、トリクロルホン、チオメトン、ホスメット、ジクロルボス、アセフェート、EPBP、メチルパラチオン、オキシジメトンメチル、エチオン、サリチオン、シアノホス、イソキサチオン、ピリダフェンチオン、ホサロン、メチダチオン、スルプロホス、クロルフェンビンホス、テトラクロルビンホス、ジメチルビンホス、プロパホス、イソフェンホス、エチルチオメトン、プロフェノホス、ピラクロホス、モノクロトホス、アジンホスメチル、アルディカルブ、メソミル、チオジカルブ、カルボフラン、カルボスルファン、ベンフラカルブ、フラチオカルブ、プロポキスル、BPMC、MTMC、MIPC、カルバリル、ピリミカーブ、エチオフェンカルブ、フェノキシカルブ、EDDPなど。 Insecticides and acaricides:
Organophosphorus and carbamate insecticides:
Fenthion, Fenitrothion, Diazinon, Chlorpyrifos, ESP, Bamidthione, Fentoate, Dimethoate, Formothion, Marathon, Trichlorfone, Thiomethone, Phosmet, Dichlorvos, Acephate, EPBP, Methyl parathion, Oxydimethone methyl, Ethion, Salicione, Cyanophos, Fenthion, Salon Methidathione, Sulprophos, Chlorfenvinphos, Tetrachlorbinphos, Dimethylvinphos, Propafos, Isophenphos, Ethylthiomethone, Profenofos, Piracrofos, Monocrotophos, Adinfosmethyl, Aldicarb, Mesomil, Thiodicarb, Carbofuran, Carbosulfan, Benhracarb, Furatiocarb Propoxyl, BPMC, MTMC, MIPC, Kalbarri Le, Pirimi curve, Ethiophene carb, Phenoxy carb, EDDP.
ピレスロイド系殺虫剤:
ペルメトリン、シペルメトリン、デルタメスリン、フェンバレレート、フェンプロパトリン、ピレトリン、アレスリン、テトラメスリン、レスメトリン、ジメスリン、プロパスリン、フェノトリン、プロトリン、フルバリネート、シフルトリン、シハロトリン、フルシトリネート、エトフェンプロクス、シクロプロトリン、トロラメトリン、シラフルオフェン、ブロフェンプロクス、アクリナスリンなど。 Pyrethroid insecticides:
Permethrin, cypermethrin, deltamethrin, fenvalerate, fenpropatoline, pyrethrin, allethrin, tetramethrin, resmethrin, dimethrin, propraslin, phenothrin, protorin, fulvalinate, cyfluthrin, cyhalothrin, flucitrinate, etofenprox, cycloprotorin, thoramethrin , Silafluophene, brofenprox, aclinasrin, etc.
ペルメトリン、シペルメトリン、デルタメスリン、フェンバレレート、フェンプロパトリン、ピレトリン、アレスリン、テトラメスリン、レスメトリン、ジメスリン、プロパスリン、フェノトリン、プロトリン、フルバリネート、シフルトリン、シハロトリン、フルシトリネート、エトフェンプロクス、シクロプロトリン、トロラメトリン、シラフルオフェン、ブロフェンプロクス、アクリナスリンなど。 Pyrethroid insecticides:
Permethrin, cypermethrin, deltamethrin, fenvalerate, fenpropatoline, pyrethrin, allethrin, tetramethrin, resmethrin, dimethrin, propraslin, phenothrin, protorin, fulvalinate, cyfluthrin, cyhalothrin, flucitrinate, etofenprox, cycloprotorin, thoramethrin , Silafluophene, brofenprox, aclinasrin, etc.
ベンゾイルウレア系その他の殺虫剤:
ジフルベンズロン、クロルフルアズロン、ヘキサフルムロン、トリフルムロン、テトラベンズロン、フルフェノクスロン、フルシクロクスロン、ブプロフェジン、ピリプロキシフェン、メトプレン、ベンゾエピン、ジアフェンチウロン、アセタミプリド、イミダクロプリド、ニテンピラム、フィプロニル、カルタップ、チオシクラム、ベンスルタップ、硫酸ニコチン、ロテノン、メタアルデヒド、機械油、BTや昆虫病原ウイルスなどの微生物農薬など。 Benzoylurea and other insecticides:
Diflubenzuron, chlorfluazuron, hexaflumuron, triflumuron, tetrabenzuron, flufenoxuron, flucycloxuron, buprofezin, pyriproxyfen, metoprene, benzoepin, diafenthiuron, acetamiprid, imidacloprid, nitenpyram, fipronil, cartap , Thiocyclam, bensultap, nicotine sulfate, rotenone, metaldehyde, machine oil, microbial pesticides such as BT and entomopathogenic viruses.
ジフルベンズロン、クロルフルアズロン、ヘキサフルムロン、トリフルムロン、テトラベンズロン、フルフェノクスロン、フルシクロクスロン、ブプロフェジン、ピリプロキシフェン、メトプレン、ベンゾエピン、ジアフェンチウロン、アセタミプリド、イミダクロプリド、ニテンピラム、フィプロニル、カルタップ、チオシクラム、ベンスルタップ、硫酸ニコチン、ロテノン、メタアルデヒド、機械油、BTや昆虫病原ウイルスなどの微生物農薬など。 Benzoylurea and other insecticides:
Diflubenzuron, chlorfluazuron, hexaflumuron, triflumuron, tetrabenzuron, flufenoxuron, flucycloxuron, buprofezin, pyriproxyfen, metoprene, benzoepin, diafenthiuron, acetamiprid, imidacloprid, nitenpyram, fipronil, cartap , Thiocyclam, bensultap, nicotine sulfate, rotenone, metaldehyde, machine oil, microbial pesticides such as BT and entomopathogenic viruses.
殺線虫剤:
フェナミホス、ホスチアゼートなど。 Nematicides:
Phenamifos, phostiazates, etc.
フェナミホス、ホスチアゼートなど。 Nematicides:
Phenamifos, phostiazates, etc.
殺ダニ剤:
クロルベンジレート、フェニソブロモレート、ジコホル、アミトラズ、BPPS、ベンゾメート、ヘキシチアゾクス、酸化フェンブタスズ、ポリナクチン、キノメチオネート、CPCBS、テトラジホン、アベルメクチン、ミルベメクチン、クロフェンテジン、シヘキサチン、ピリダベン、フェンピロキシメート、テブフェンピラド、ピリミジフェン、フェノチオカルブ、ジエノクロルなど。 Acaricide:
Chlorbenzilate, phenisobromolate, dicophore, amitraz, BPPS, benzomate, hexithazox, fenbutazin oxide, polynactin, quinomethionate, CPCBS, tetradiphone, avermectin, milbemectin, clofentedin, cihexatin, pyridaben, fenpyroximate, tebufenpyrad, thiomidibene Dienochlor etc.
クロルベンジレート、フェニソブロモレート、ジコホル、アミトラズ、BPPS、ベンゾメート、ヘキシチアゾクス、酸化フェンブタスズ、ポリナクチン、キノメチオネート、CPCBS、テトラジホン、アベルメクチン、ミルベメクチン、クロフェンテジン、シヘキサチン、ピリダベン、フェンピロキシメート、テブフェンピラド、ピリミジフェン、フェノチオカルブ、ジエノクロルなど。 Acaricide:
Chlorbenzilate, phenisobromolate, dicophore, amitraz, BPPS, benzomate, hexithazox, fenbutazin oxide, polynactin, quinomethionate, CPCBS, tetradiphone, avermectin, milbemectin, clofentedin, cihexatin, pyridaben, fenpyroximate, tebufenpyrad, thiomidibene Dienochlor etc.
植物生長調節剤:
ジベレリン類(例えばジベレリンA3、ジベレリンA4、ジベレリンA7)、IAA、NAAなど。 Plant growth regulator:
Gibberellins (eg, gibberellin A3, gibberellin A4, gibberellin A7), IAA, NAA and the like.
ジベレリン類(例えばジベレリンA3、ジベレリンA4、ジベレリンA7)、IAA、NAAなど。 Plant growth regulator:
Gibberellins (eg, gibberellin A3, gibberellin A4, gibberellin A7), IAA, NAA and the like.
次に、実施例を示して、本発明を具体的に説明する。但し、本発明は以下の実施例により何ら限定されることはない。
Next, the present invention will be specifically described with reference to examples. However, the present invention is not limited to the following examples.
本発明化合物は、特許文献3に記載の方法に準拠して製造した。製造された本発明化合物の一部を表(4)~(6)に物性値と併せて示す。また、NMRデータを表(7)に示す。
The compound of the present invention was produced according to the method described in Patent Document 3. Some of the produced compounds of the present invention are shown in Tables (4) to (6) together with physical property values. The NMR data is shown in Table (7).
次に、本発明殺菌剤の製剤実施例を以下に示すが、添加物および添加割合は、これら製剤実施例に限定されるものではなく、広範囲に変化させることが可能である。また、製剤実施例中の部は重量部を示す。
Next, formulation examples of the fungicide of the present invention are shown below, but the additives and addition ratios are not limited to these formulation examples, and can be varied in a wide range. Moreover, the part in a formulation Example shows a weight part.
製剤実施例1 水和剤
本発明のオキシムエーテル誘導体化合物 40部
クレー 48部
ジオクチルスルホサクシネートナトリウム塩 4部
リグニンスルホン酸ナトリウム塩 8部
以上を均一に混合して微細に粉砕し、有効成分40%の水和剤を得る。 Formulation Example 1 Wetting agent Oxime ether derivative compound of the present invention 40 parts Clay 48 parts Dioctyl sulfosuccinate sodium salt 4 parts Lignin sulfonic acid sodium salt 8 parts or more uniformly mixed and finely pulverized, active ingredient 40% Get a wettable powder.
本発明のオキシムエーテル誘導体化合物 40部
クレー 48部
ジオクチルスルホサクシネートナトリウム塩 4部
リグニンスルホン酸ナトリウム塩 8部
以上を均一に混合して微細に粉砕し、有効成分40%の水和剤を得る。 Formulation Example 1 Wetting agent Oxime ether derivative compound of the present invention 40 parts Clay 48 parts Dioctyl sulfosuccinate sodium salt 4 parts Lignin sulfonic acid sodium salt 8 parts or more uniformly mixed and finely pulverized, active ingredient 40% Get a wettable powder.
製剤実施例2 乳剤
本発明のオキシムエーテル誘導体化合物 10部
ソルベッソ200 53部
シクロヘキサノン 26部
ドデシルベンゼンスルホン酸カルシウム塩 1部
ポリオキシエチレンアルキルアリルエーテル 10部
以上を混合溶解し、有効成分10%の乳剤を得る。 Formulation Example 2 Emulsion Oxime ether derivative compound of the present invention 10 parts Solvesso 200 53 parts Cyclohexanone 26 parts Calcium dodecylbenzenesulfonate 1 part Polyoxyethylene alkylallyl ether 10 parts Mixing and dissolving the above, an emulsion containing 10% active ingredient obtain.
本発明のオキシムエーテル誘導体化合物 10部
ソルベッソ200 53部
シクロヘキサノン 26部
ドデシルベンゼンスルホン酸カルシウム塩 1部
ポリオキシエチレンアルキルアリルエーテル 10部
以上を混合溶解し、有効成分10%の乳剤を得る。 Formulation Example 2 Emulsion Oxime ether derivative compound of the present invention 10 parts Solvesso 200 53 parts Cyclohexanone 26 parts Calcium dodecylbenzenesulfonate 1 part Polyoxyethylene alkylallyl ether 10 parts Mixing and dissolving the above, an emulsion containing 10% active ingredient obtain.
製剤実施例3 粉剤
本発明のオキシムエーテル誘導体化合物 10部
クレー 90部
以上を均一に混合して微細に粉砕し、有効成分10%の粉剤を得る。 Formulation Example 3 Powder A oxime ether derivative compound of the present invention 10 parts Clay 90 parts The above is uniformly mixed and finely pulverized to obtain a powder of 10% active ingredient.
本発明のオキシムエーテル誘導体化合物 10部
クレー 90部
以上を均一に混合して微細に粉砕し、有効成分10%の粉剤を得る。 Formulation Example 3 Powder A oxime ether derivative compound of the present invention 10 parts Clay 90 parts The above is uniformly mixed and finely pulverized to obtain a powder of 10% active ingredient.
製剤実施例4 粒剤
本発明のオキシムエーテル誘導体化合物 5部
クレー 73部
ベントナイト 20部
ジオクチルスルホサクシネートナトリウム塩 1部
リン酸カリウム 1部
以上をよく粉砕混合し、水を加えてよく練り合せた後、造粒乾燥して有効成分5%の粒剤を得る。 Formulation Example 4 Granule Oxime ether derivative compound of the present invention 5 parts Clay 73 parts Bentonite 20 parts Dioctyl sulfosuccinate sodium salt 1 part Potassium phosphate 1 part After the above is well ground and mixed, water is added and kneaded well Granulation and drying to obtain granules with 5% active ingredient.
本発明のオキシムエーテル誘導体化合物 5部
クレー 73部
ベントナイト 20部
ジオクチルスルホサクシネートナトリウム塩 1部
リン酸カリウム 1部
以上をよく粉砕混合し、水を加えてよく練り合せた後、造粒乾燥して有効成分5%の粒剤を得る。 Formulation Example 4 Granule Oxime ether derivative compound of the present invention 5 parts Clay 73 parts Bentonite 20 parts Dioctyl sulfosuccinate sodium salt 1 part Potassium phosphate 1 part After the above is well ground and mixed, water is added and kneaded well Granulation and drying to obtain granules with 5% active ingredient.
製剤実施例5 懸濁剤
本発明のオキシムエーテル誘導体化合物 10部
ポリオキシエチレンアルキルアリルエーテル 4部
ポリカルボン酸ナトリウム塩 2部
グリセリン 10部
キサンタンガム 0.2部
水 73.8部
以上を混合し、粒度が3ミクロン以下になるまで湿式粉砕し、有効成分10%の懸濁剤を得る。 Formulation Example 5 Suspension agent Oxime ether derivative compound of the present invention 10 parts Polyoxyethylene alkylallyl ether 4 parts Polycarboxylic acid sodium salt 2 parts Glycerin 10 parts Xanthan gum 0.2 parts Water 73.8 parts Is pulverized wet until it becomes 3 microns or less to obtain a suspension with 10% active ingredient.
本発明のオキシムエーテル誘導体化合物 10部
ポリオキシエチレンアルキルアリルエーテル 4部
ポリカルボン酸ナトリウム塩 2部
グリセリン 10部
キサンタンガム 0.2部
水 73.8部
以上を混合し、粒度が3ミクロン以下になるまで湿式粉砕し、有効成分10%の懸濁剤を得る。 Formulation Example 5 Suspension agent Oxime ether derivative compound of the present invention 10 parts Polyoxyethylene alkylallyl ether 4 parts Polycarboxylic acid sodium salt 2 parts Glycerin 10 parts Xanthan gum 0.2 parts Water 73.8 parts Is pulverized wet until it becomes 3 microns or less to obtain a suspension with 10% active ingredient.
製剤実施例6 顆粒水和剤
本発明のオキシムエーテル誘導体化合物 40部
クレー 36部
塩化カリウム 10部
アルキルベンゼンスルホン酸ナトリウム塩 1部
リグニンスルホン酸ナトリウム塩 8部
アルキルベンゼンスルホン酸ナトリウム塩のホルムアルデヒド縮合物
5部
以上を均一に混合して微細に粉砕後,適量の水を加えてから練り込んで粘土状にする。粘土状物を造粒した後乾燥し、有効成分40%の水和剤を得る。 Formulation Example 6 Granule wettable powder Oxime ether derivative compound of the present invention 40 parts Clay 36 parts Potassium chloride 10 parts Alkylbenzenesulfonic acid sodium salt 1 part Lignin sulfonic acid sodium salt 8 parts Formaldehyde condensate of alkylbenzenesulfonic acid sodium salt 5 parts or more After mixing the mixture uniformly and finely pulverizing, add an appropriate amount of water and knead to make a clay. The clay-like product is granulated and then dried to obtain a wettable powder containing 40% of the active ingredient.
本発明のオキシムエーテル誘導体化合物 40部
クレー 36部
塩化カリウム 10部
アルキルベンゼンスルホン酸ナトリウム塩 1部
リグニンスルホン酸ナトリウム塩 8部
アルキルベンゼンスルホン酸ナトリウム塩のホルムアルデヒド縮合物
5部
以上を均一に混合して微細に粉砕後,適量の水を加えてから練り込んで粘土状にする。粘土状物を造粒した後乾燥し、有効成分40%の水和剤を得る。 Formulation Example 6 Granule wettable powder Oxime ether derivative compound of the present invention 40 parts Clay 36 parts Potassium chloride 10 parts Alkylbenzenesulfonic acid sodium salt 1 part Lignin sulfonic acid sodium salt 8 parts Formaldehyde condensate of alkylbenzenesulfonic acid sodium salt 5 parts or more After mixing the mixture uniformly and finely pulverizing, add an appropriate amount of water and knead to make a clay. The clay-like product is granulated and then dried to obtain a wettable powder containing 40% of the active ingredient.
本発明殺菌剤の活性を確認するための試験を以下のように行った。
なお、防除効果は下記のアボット(Abbot)の式から防除価として算出した。
防除価 (%)= (1 - α/β) × 100
αは、処理された植物の菌類感染量に対応し、
βは、無処理(対照)の植物の菌類感染量に対応する。
防除価0%は、処理された植物の感染レベルが、未処理の対照植物のそれと一致することを意味し、効果100%は処理された植物が全く感染しなかったことを意味する。 A test for confirming the activity of the fungicide of the present invention was performed as follows.
The control effect was calculated as a control value from the following Abbot formula.
Control value (%) = (1−α / β) × 100
α corresponds to the amount of fungal infection in the treated plant,
β corresponds to the amount of fungal infection in untreated (control) plants.
A control value of 0% means that the level of infection of the treated plants is consistent with that of the untreated control plants, and an effect of 100% means that the treated plants were not infected at all.
なお、防除効果は下記のアボット(Abbot)の式から防除価として算出した。
防除価 (%)= (1 - α/β) × 100
αは、処理された植物の菌類感染量に対応し、
βは、無処理(対照)の植物の菌類感染量に対応する。
防除価0%は、処理された植物の感染レベルが、未処理の対照植物のそれと一致することを意味し、効果100%は処理された植物が全く感染しなかったことを意味する。 A test for confirming the activity of the fungicide of the present invention was performed as follows.
The control effect was calculated as a control value from the following Abbot formula.
Control value (%) = (1−α / β) × 100
α corresponds to the amount of fungal infection in the treated plant,
β corresponds to the amount of fungal infection in untreated (control) plants.
A control value of 0% means that the level of infection of the treated plants is consistent with that of the untreated control plants, and an effect of 100% means that the treated plants were not infected at all.
(試験例1)リンゴ黒星病防除試験
製剤実施例2の処方に従って製造した乳剤を水で希釈し、有効成分濃度100ppmに調整した。該希釈剤を、素焼きポットで栽培したリンゴ幼苗(品種「国光」、3~4葉期)に散布した。次いで、室温で自然乾燥した。リンゴ黒星病菌(Venturia inaequalis)の分生胞子を接種し、明暗を12時間毎に繰り返す20℃、高湿度の室内に2週間保持した。葉上の病斑出現状態を無処理と比較調査し、防除効果を調べた。
リンゴ黒星病防除試験を、表(4)~(6)の化合物番号1、2、3、4、5、6、7、9、10、11、12、13、14、15、16、17、18、19、20、21、22、23、24、25、26、および27のオキシムエーテル誘導体化合物について行った。その結果、いずれの化合物も75%以上の優れた防除価を示した。 (Test Example 1) Apple scab control test The emulsion produced according to the formulation of Formulation Example 2 was diluted with water to adjust the active ingredient concentration to 100 ppm. The diluent was sprayed on apple seedlings grown in an unglazed pot (variety “Kokumi”, 3-4 leaf stage). Next, it was naturally dried at room temperature. Conidia spores of Venturia inaequalis were inoculated and kept in a room at 20 ° C. and high humidity for 2 weeks, repeating light and dark every 12 hours. The lesion appearance state on the leaf was compared with no treatment, and the control effect was examined.
The apple scab control test was conducted using compound numbers 1, 2, 3, 4, 5, 6, 7, 9, 10, 11, 12, 13, 14, 15, 16, 17, in Tables (4) to (6). The oxime ether derivative compounds of 18, 19, 20, 21, 22, 23, 24, 25, 26, and 27 were used. As a result, all the compounds showed an excellent control value of 75% or more.
製剤実施例2の処方に従って製造した乳剤を水で希釈し、有効成分濃度100ppmに調整した。該希釈剤を、素焼きポットで栽培したリンゴ幼苗(品種「国光」、3~4葉期)に散布した。次いで、室温で自然乾燥した。リンゴ黒星病菌(Venturia inaequalis)の分生胞子を接種し、明暗を12時間毎に繰り返す20℃、高湿度の室内に2週間保持した。葉上の病斑出現状態を無処理と比較調査し、防除効果を調べた。
リンゴ黒星病防除試験を、表(4)~(6)の化合物番号1、2、3、4、5、6、7、9、10、11、12、13、14、15、16、17、18、19、20、21、22、23、24、25、26、および27のオキシムエーテル誘導体化合物について行った。その結果、いずれの化合物も75%以上の優れた防除価を示した。 (Test Example 1) Apple scab control test The emulsion produced according to the formulation of Formulation Example 2 was diluted with water to adjust the active ingredient concentration to 100 ppm. The diluent was sprayed on apple seedlings grown in an unglazed pot (variety “Kokumi”, 3-4 leaf stage). Next, it was naturally dried at room temperature. Conidia spores of Venturia inaequalis were inoculated and kept in a room at 20 ° C. and high humidity for 2 weeks, repeating light and dark every 12 hours. The lesion appearance state on the leaf was compared with no treatment, and the control effect was examined.
The apple scab control test was conducted using compound numbers 1, 2, 3, 4, 5, 6, 7, 9, 10, 11, 12, 13, 14, 15, 16, 17, in Tables (4) to (6). The oxime ether derivative compounds of 18, 19, 20, 21, 22, 23, 24, 25, 26, and 27 were used. As a result, all the compounds showed an excellent control value of 75% or more.
(試験例2)コムギうどんこ病防除試験
製剤実施例1の処方に従って製造した水和剤を水で希釈し、有効成分濃度100ppmに調整した。該希釈剤を、素焼きポットで栽培したコムギ幼苗(品種「チホク」、1.0~1.2葉期)に散布した。次いで、葉を風乾させた。コムギうどんこ病菌(Erysiphe graminis f.sp.tritici)の分生胞子を振り払い接種し、22~25℃の温室で7日間保持した。葉上の病斑出現状態を無処理と比較調査し、防除効果を調べた。
コムギうどんこ病防除試験を表(4)~(6)の化合物番号1、3、4、5、7、11、12、13、16、17、18、19、20、21、22、23、24、25、26、および27のオキシムエーテル誘導体化合物について行った。その結果、いずれの化合物も75%以上の優れた防除価を示した。 (Test Example 2) Wheat powdery mildew control test A wettable powder prepared according to the formulation of Formulation Example 1 was diluted with water to adjust the active ingredient concentration to 100 ppm. The diluent was sprayed on wheat seedlings (variety “Chihoku”, 1.0-1.2 leaf stage) grown in an unglazed pot. The leaves were then air dried. The conidia of wheat powdery mildew (Erysiphe graminis f.sp.tritici) were shaken off and inoculated in a greenhouse at 22-25 ° C. for 7 days. The lesion appearance state on the leaf was compared with no treatment, and the control effect was examined.
The wheat powdery mildew prevention test was conducted using compound numbers 1, 3, 4, 5, 7, 11, 12, 13, 16, 17, 18, 19, 20, 21, 22, 23, Tables (4) to (6). 24, 25, 26, and 27 oxime ether derivative compounds were carried out. As a result, all the compounds showed an excellent control value of 75% or more.
製剤実施例1の処方に従って製造した水和剤を水で希釈し、有効成分濃度100ppmに調整した。該希釈剤を、素焼きポットで栽培したコムギ幼苗(品種「チホク」、1.0~1.2葉期)に散布した。次いで、葉を風乾させた。コムギうどんこ病菌(Erysiphe graminis f.sp.tritici)の分生胞子を振り払い接種し、22~25℃の温室で7日間保持した。葉上の病斑出現状態を無処理と比較調査し、防除効果を調べた。
コムギうどんこ病防除試験を表(4)~(6)の化合物番号1、3、4、5、7、11、12、13、16、17、18、19、20、21、22、23、24、25、26、および27のオキシムエーテル誘導体化合物について行った。その結果、いずれの化合物も75%以上の優れた防除価を示した。 (Test Example 2) Wheat powdery mildew control test A wettable powder prepared according to the formulation of Formulation Example 1 was diluted with water to adjust the active ingredient concentration to 100 ppm. The diluent was sprayed on wheat seedlings (variety “Chihoku”, 1.0-1.2 leaf stage) grown in an unglazed pot. The leaves were then air dried. The conidia of wheat powdery mildew (Erysiphe graminis f.sp.tritici) were shaken off and inoculated in a greenhouse at 22-25 ° C. for 7 days. The lesion appearance state on the leaf was compared with no treatment, and the control effect was examined.
The wheat powdery mildew prevention test was conducted using compound numbers 1, 3, 4, 5, 7, 11, 12, 13, 16, 17, 18, 19, 20, 21, 22, 23, Tables (4) to (6). 24, 25, 26, and 27 oxime ether derivative compounds were carried out. As a result, all the compounds showed an excellent control value of 75% or more.
(試験例3)コムギ赤さび病防除試験
製剤実施例1の処方に従って製造した水和剤を水で希釈し、有効成分濃度100ppmに調整した。該希釈剤を、素焼きポットで栽培したコムギ幼苗(品種「農林61号」、1.0~1.2葉期)に散布した。次いで、葉を風乾させた。コムギ赤さび病菌(Puccinia recondita)の夏胞子を振り払い接種し、22~25℃の温室で10日間保持した。葉上の病斑出現状態を無処理と比較調査し、防除効果を調べた。
コムギ赤さび病防除試験を表(4)~(6)の化合物番号1、3、4、5、7、8、9、10、11、12、13、14、15、16、17、18、19、20、21、22、23、24、25、26、および27のオキシムエーテル誘導体化合物について行った。その結果、いずれの化合物も75%以上の優れた防除価を示した。 (Test Example 3) Wheat red rust control test A wettable powder produced according to the formulation of Preparation Example 1 was diluted with water to adjust the active ingredient concentration to 100 ppm. The diluent was sprayed on wheat seedlings grown in an unglazed pot (variety “Noribayashi No. 61”, 1.0-1.2 leaf stage). The leaves were then air dried. The wheat spores (Puccinia recondita) summer spores were shaken and inoculated, and kept in a greenhouse at 22-25 ° C. for 10 days. The lesion appearance state on the leaf was compared with no treatment, and the control effect was examined.
Wheat red rust control test was conducted using compound numbers 1, 3, 4, 5, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 in Tables (4) to (6). , 20, 21, 22, 23, 24, 25, 26, and 27 oxime ether derivative compounds. As a result, all the compounds showed an excellent control value of 75% or more.
製剤実施例1の処方に従って製造した水和剤を水で希釈し、有効成分濃度100ppmに調整した。該希釈剤を、素焼きポットで栽培したコムギ幼苗(品種「農林61号」、1.0~1.2葉期)に散布した。次いで、葉を風乾させた。コムギ赤さび病菌(Puccinia recondita)の夏胞子を振り払い接種し、22~25℃の温室で10日間保持した。葉上の病斑出現状態を無処理と比較調査し、防除効果を調べた。
コムギ赤さび病防除試験を表(4)~(6)の化合物番号1、3、4、5、7、8、9、10、11、12、13、14、15、16、17、18、19、20、21、22、23、24、25、26、および27のオキシムエーテル誘導体化合物について行った。その結果、いずれの化合物も75%以上の優れた防除価を示した。 (Test Example 3) Wheat red rust control test A wettable powder produced according to the formulation of Preparation Example 1 was diluted with water to adjust the active ingredient concentration to 100 ppm. The diluent was sprayed on wheat seedlings grown in an unglazed pot (variety “Noribayashi No. 61”, 1.0-1.2 leaf stage). The leaves were then air dried. The wheat spores (Puccinia recondita) summer spores were shaken and inoculated, and kept in a greenhouse at 22-25 ° C. for 10 days. The lesion appearance state on the leaf was compared with no treatment, and the control effect was examined.
Wheat red rust control test was conducted using compound numbers 1, 3, 4, 5, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 in Tables (4) to (6). , 20, 21, 22, 23, 24, 25, 26, and 27 oxime ether derivative compounds. As a result, all the compounds showed an excellent control value of 75% or more.
本発明化合物は、工業的に容易に製造することができ、多くの農園芸作物に対して、少ない施用量で防除効果が大きく、浸透移行性と残効性が優れるために病害に対する防除効果が確実で、しかも安全に使用できる農園芸用殺菌剤の活性成分として有用な新規化合物である。
The compound of the present invention can be easily produced industrially, has a large control effect at a small application rate for many agricultural and horticultural crops, and has an excellent osmotic migration and residual effect, and therefore has a control effect against diseases. It is a novel compound useful as an active ingredient of an agricultural and horticultural fungicide that is reliable and can be used safely.
また、本発明殺菌剤は、本発明化合物の濃度が低く且つ施用量が少なくても、優れた防除効果を有し、植物体に薬害や汚染を生じることがなく、人畜魚類に対する毒性や環境への影響が少ない、安全性に優れる薬剤である。
In addition, the fungicide of the present invention has an excellent control effect even when the concentration of the compound of the present invention is low and the application amount is small, and does not cause phytotoxicity or pollution to the plant body. It is a drug with excellent safety and less influence.
Claims (3)
- 式(I)で表されるオキシムエーテル誘導体またはその塩。
R1およびR2はそれぞれ独立して、水素原子、ハロゲン原子、C1~8アルキル基、C1~8ハロアルキル基、または無置換の若しくは置換基を有するC3~8シクロアルキル基を表す。R1とR2とが一緒になって結合して環を形成してもよい。mは括弧内の単位の繰返し数を表わし且つ0~8のいずれかの整数である。mが2以上の場合、R1同士、R2同士は、同一であっても、相異なっていてもよい。
R3は、水素原子、C1~8アルキル基、C2~8アルケニル基、C2~8アルキニル基、C1~8ハロアルキル基、C2~8ハロアルケニル基、C2~8ハロアルキニル基、または無置換の若しくは置換基を有するC3~8シクロアルキル基を表す。
R4は、水素原子、C1~8アルキル基、無置換の若しくは置換基を有するC3~8シクロアルキル基、C2~8アルケニル基、C2~8アルキニル基、C1~8ハロアルキル基、C2~8ハロアルケニル基、またはC2~8ハロアルキニル基を表す。
R5は、水素原子、C1~8アルキル基、アシル基、ホルミル基、C1~8アルコキシC1~8アルキル基、C2~8アシルオキシC1~8アルキル基、C1~8アルコキシカルボニル基、C1~8アルキルスルホニル基、または無置換の若しくは置換基を有するフェニルスルホニル基を表す。
Yは、酸素原子または硫黄原子を表す。
Zは、単結合、酸素原子、硫黄原子、またはNR6で示される基を表す。R6は、水素原子若しくはC1~8アルキル基を表す。
Qは、無置換の若しくは置換基を有するピラゾール環基を表す。〕 An oxime ether derivative represented by the formula (I) or a salt thereof.
R 1 and R 2 each independently represents a hydrogen atom, a halogen atom, a C1-8 alkyl group, a C1-8 haloalkyl group, or an unsubstituted or substituted C3-8 cycloalkyl group. R 1 and R 2 may be bonded together to form a ring. m represents the number of repeating units in parentheses and is an integer from 0 to 8. When m is 2 or more, R 1 and R 2 may be the same or different.
R 3 is a hydrogen atom, a C1-8 alkyl group, a C2-8 alkenyl group, a C2-8 alkynyl group, a C1-8 haloalkyl group, a C2-8 haloalkenyl group, a C2-8 haloalkynyl group, or an unsubstituted or Represents a C3-8 cycloalkyl group having a substituent.
R 4 represents a hydrogen atom, a C1-8 alkyl group, an unsubstituted or substituted C3-8 cycloalkyl group, a C2-8 alkenyl group, a C2-8 alkynyl group, a C1-8 haloalkyl group, a C2-8 halo. It represents an alkenyl group or a C2-8 haloalkynyl group.
R 5 is a hydrogen atom, C1-8 alkyl group, acyl group, formyl group, C1-8 alkoxy C1-8 alkyl group, C2-8 acyloxy C1-8 alkyl group, C1-8 alkoxycarbonyl group, C1-8 alkyl A sulfonyl group or an unsubstituted or substituted phenylsulfonyl group is represented.
Y represents an oxygen atom or a sulfur atom.
Z represents a single bond, an oxygen atom, a sulfur atom, or a group represented by NR 6 . R 6 represents a hydrogen atom or a C1-8 alkyl group.
Q represents an unsubstituted or substituted pyrazole ring group. ] - XがC1~8アルキル基であり、R1、R2、R3、R4およびR5がそれぞれ独立に水素原子またはC1~8アルキル基であり、YおよびZが酸素原子であり、Qが無置換の若しくは置換基を有する1H-ピラゾール-3-イル基、無置換の若しくは置換基を有する2H-ピラゾール-3-イル基、または、無置換の若しくは置換基を有する1H-ピラゾール-4-イル基であり、mが1であり、且つnが0~1である、請求項1に記載のオキシムエーテル誘導体またはその塩。 X is a C1-8 alkyl group, R 1 , R 2 , R 3 , R 4 and R 5 are each independently a hydrogen atom or a C1-8 alkyl group, Y and Z are oxygen atoms, and Q is An unsubstituted or substituted 1H-pyrazol-3-yl group, an unsubstituted or substituted 2H-pyrazol-3-yl group, or an unsubstituted or substituted 1H-pyrazol-4- The oxime ether derivative or a salt thereof according to claim 1, which is an yl group, m is 1, and n is 0 to 1.
- 請求項1または2に記載のオキシムエーテル誘導体またはその塩から選ばれる少なくとも1種を有効成分として含有する農園芸用殺菌剤。 An agricultural and horticultural fungicide containing as an active ingredient at least one selected from the oxime ether derivatives or salts thereof according to claim 1 or 2.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2010044194A JP2013100234A (en) | 2010-03-01 | 2010-03-01 | Oxime ether derivative or salt thereof and agriculture and horticulture fungicide |
JP2010-044194 | 2010-03-01 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2011108396A1 true WO2011108396A1 (en) | 2011-09-09 |
Family
ID=44542052
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2011/053807 WO2011108396A1 (en) | 2010-03-01 | 2011-02-22 | Oxime ether derivatives or salts thereof, and germicides for agricultural or horticultural use |
Country Status (2)
Country | Link |
---|---|
JP (1) | JP2013100234A (en) |
WO (1) | WO2011108396A1 (en) |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2003231672A (en) * | 2001-08-03 | 2003-08-19 | Nissan Chem Ind Ltd | Oxime type compound or its salts and bactericide for agriculture and horticulture |
JP2004168683A (en) * | 2002-11-19 | 2004-06-17 | Nippon Soda Co Ltd | Oxyamine derivative, production intermediate and fungicide for agriculture and horticulture |
WO2009075112A1 (en) * | 2007-12-11 | 2009-06-18 | Nippon Soda Co., Ltd. | Oxime ether derivative and bactericide for agricultural and horticultural use |
-
2010
- 2010-03-01 JP JP2010044194A patent/JP2013100234A/en active Pending
-
2011
- 2011-02-22 WO PCT/JP2011/053807 patent/WO2011108396A1/en active Application Filing
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2003231672A (en) * | 2001-08-03 | 2003-08-19 | Nissan Chem Ind Ltd | Oxime type compound or its salts and bactericide for agriculture and horticulture |
JP2004168683A (en) * | 2002-11-19 | 2004-06-17 | Nippon Soda Co Ltd | Oxyamine derivative, production intermediate and fungicide for agriculture and horticulture |
WO2009075112A1 (en) * | 2007-12-11 | 2009-06-18 | Nippon Soda Co., Ltd. | Oxime ether derivative and bactericide for agricultural and horticultural use |
Non-Patent Citations (1)
Title |
---|
ARIMOTO, M. ET AL.: "Semisynthetic beta-lactam antibiotics. IV. Synthesis and antibacterial activity of 7beta-[2-(hetero aromatic methoxyimino)-2-(2-aminothiazol-4-yl)acetamido] cephalosporins", JOURNAL OF ANTIBIOTICS, vol. 41, no. 12, 1988, pages 1795 - 1811 * |
Also Published As
Publication number | Publication date |
---|---|
JP2013100234A (en) | 2013-05-23 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5587970B2 (en) | Tetrazolyl oxime derivative or salt thereof, and fungicide | |
JP5133985B2 (en) | Tetrazoyl oxime derivatives and plant disease control agents | |
JPH10324687A (en) | Pyrrole compound, production and agricultural and horticultural microbicide | |
JP5215321B2 (en) | Oxime ether derivatives and agricultural and horticultural fungicides | |
JP2005145840A (en) | Condensed heterocyclic derivative and agricultural and horticultural fungicide | |
KR101372606B1 (en) | Tetrazoyl oxime derivative, salt thereof, and plant disease control agent | |
WO2010018676A1 (en) | Oxime ether derivative and bactericide for agricultural and horticultural use | |
EP1362850A1 (en) | Oxime ether compound and agricultural or horticultural bactericide | |
JP5542452B2 (en) | Tetrazoyloxime derivatives and salts thereof, and plant disease control agents | |
JP5322296B2 (en) | Method for using plant disease control agent containing tetrazoyloxime derivative | |
JP2014156402A (en) | Bipyridine compound and antimicrobial agent | |
JP2002212157A (en) | Acylaminosalicylic acid derivative, method for producing the same and agricultural and horticultural fungicide | |
JP2007008891A (en) | Hydrazinecarboxylic acid derivative and germicide for agriculture and horticulture | |
WO2011108396A1 (en) | Oxime ether derivatives or salts thereof, and germicides for agricultural or horticultural use | |
JPWO2004011445A1 (en) | Aminosalicylic acid amide derivative, production method and agricultural and horticultural fungicide | |
JP2007161621A (en) | Nitrogen-containing heterocyclic compound and agricultural/horticultural fungicide | |
JP2004323516A (en) | 3-acylaminosalicyclic acid amide derivative, method for producing the same and agricultural and horticultural bactericidal agent | |
JP2013006771A (en) | Oxime ether derivative or salt thereof, and agricultural/horticultural fungicide | |
JP2006327973A (en) | Derivative of aryl heterocyclic compound and bactericide for agriculture and horticulture | |
JP2009149598A (en) | Azine derivative, and agricultural and horticultural fungicide | |
JP2000026471A (en) | 11-formyl-indolo[1,2-b][1,2]benzisothiazole and microbicidal agent for agricultural and horticultural purposes | |
JP2003048876A (en) | Thioamide derivative and agricultural horticultural antimicrobial agent | |
JP2008290945A (en) | Aryl heterocyclic derivative and bactericide for agricultural and horticultural use | |
US20040072826A1 (en) | Organic compound having cyano group and insecticides/miticides | |
JP2004067565A (en) | Carbamate compound, method for producing the same and agricultural and horticultural fungicide |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 11750508 Country of ref document: EP Kind code of ref document: A1 |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
122 | Ep: pct application non-entry in european phase |
Ref document number: 11750508 Country of ref document: EP Kind code of ref document: A1 |
|
NENP | Non-entry into the national phase |
Ref country code: JP |