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    1/1 Summary "Derived from 2-aminonicotonic acid ester ester, and bactericidal" The present invention provides a bactericide containing a2-aminonicotonic acid ester derivative as an active ingredient. the active ingredient is represented by the following formula [i]: 3 4 ror 5 2 rroo 6 ab 1 rrn nh 2 ï¼ »â… ï¼½ 1 (where, r represents a hydrogen atom or a group 2 alkyl c - c, r represents a hydrogen atom, an alkyl group c-c, 1 4 1 4 1 2 or r and are combined together to form an alkylene chain, 3 4 r represents a hydrogen atom or an alkyl group c-c, r 1 4 represents a hydrogen atom, a cyano group or an alkyl group c-1 5 6 c, and independently represent a hydrogen atom, a 4 atom of halogen, a c-c alkyl group, a c-c alkoxy group, a c-c alkylthio group, a c-c alkylsulfinyl group, a c-c 1 4 1 4 1 4 alkylsulfonyl group, a nitro group , a cyano group, a C1 -C4 haloalkyl group, a C1 -C4 alkoxy halogen group or a C1 -C4 haloalkylthio group, a and b 1 4 1 4 independently represent a methoxy (CH) group or an atom of nitrogen).
    公开号:BR112014032873B1
    申请号:R112014032873-0
    申请日:2013-04-02
    公开日:2019-02-12
    发明作者:Ryo Aizawa；Itaru Okada；Toshiki Fukuchi；Masahiro Hatamoto
    申请人:Agro-Kanesho Co., Ltd.；
    IPC主号:
    专利说明:

    “2-AMINONICOTINIC ACID ESTER DERIVED, AND, BACTERICIDE”
    DESCRIPTION
    TECHNICAL FIELD [001] The present invention relates to an ester derivative of acid
    2-aminonicotinic and a bactericide containing it as an active ingredient.
    FUNDAMENTALS OF THE TECHNIQUE [002] In a field of agriculture and horticulture, several bactericides designed to control a wide variety of pathogenic bacteria have been developed and used in practice.
    [003] However, conventional agricultural chemicals commonly used do not necessarily meet the requirements of their effects, spectrum of residual activities, and the like, as well as those for reducing application frequencies, application doses and the like. In addition, there is a problem with the occurrence of pathogenic bacteria that have developed resistance to commonly used conventional agricultural chemicals. For example, in growing vegetables, fruit trees, flowering plants, tea plants, barley or wheat, rice plants and the like, for example, various types of pathogenic bacteria having developed resistance to various types of bactericidal agents, such as bactericides triazole, imidazole, pyrimidine, benzimidazole, dicarboximide, phenylamide, strobilurin and the like have occurred in several regions, and the control of these resistant pathogenic bacteria is becoming increasingly difficult year by year. Therefore, the development of a new agricultural chemical, which exhibits a sufficient control effect on a wide variety of pathogenic bacteria that have developed resistance to conventional bactericides used for use in agriculture and horticulture, even at a low dose, and which has less adverse influence on medium
    2/28 environment, has been continuously required.
    [004] In order to meet these demands, several new bactericides have been proposed, but they do not necessarily satisfy the requirements described above.
    [005] Patent Document 1 describes a carboxamide derivative having a bactericidal activity and having the following structure. However, the compound described in Patent Document 1 has a carboxamide bond at position 3 of the pyridine ring, but does not have an ester bond.
    (Patent Document 1) [006] Patent Document 2 describes the following ester derivative with an amino group at position 2 of the pyridine ring as a reaction intermediate (page 265, Example 35, Compound No. 757). However, this compound has a methoxy group, but it is not a phenoxy group. In addition, this compound is described only as an intermediate in the production of a pharmaceutically active compound described in Patent Document 2, and Patent Document 2 does not describe a bactericidal activity.
    (Patent Document 2, a pharmaceutical activity) [007] Patent Documents 3 to 6 describe, as specifically synthesized compounds, ester derivatives that do not have an amino group at position 2 of the pyridine ring as follows. As their representative examples, the following compounds are exemplified. These compounds are reported to have insecticidal or herbicidal activities, but are not described
    3/28 in all these compounds that have any bactericidal activity.
    [008] Patent Document 3 describes the following compound (page 43, compound No. 1.59). However, Patent Document 3 refers to use as an insecticide, but does not describe a compound that has an amino group at position 2 of the pyridine ring.
    (Patent Document 3, an insecticidal activity) [009] Patent Document 4 describes the following compound (page 33, compounds 270 and 271). However, the patent refers to the use of Patent Document 4 as an insecticide, but does not describe a compound that has an amino group at position 2 of the pyridine ring.
    (Patent Document4, an insecticidal activity) [0010] Patent Document 5 describes the following compound (page 78, Compound No. 1.3717). However, Patent Document 5 refers to use as an herbicide, but does not describe a compound having an amino group at position 2 of the pyridine ring.
    (Patent Document 5, a herbicidal activity) [0011] Patent Document 6 describes the following compound (page 42, Compound No. 229). However, Patent Document 6 refers to use as an herbicide, but does not describe a compound that has a
    4/28 amino group at position 2 of the pyridine ring.
    (Patent Document 6, a herbicidal activity) [0012] Additionally, Patent Document 7 or
    Patent 8 describe, as specific compounds endowed with bactericidal activities, the following compounds.
    [0013] Specifically, Patent Document 7 describes the following compound (page 50, Compound No. 48). However, Patent Document 7 does not describe a compound having an amino group at position 2 of the pyridine ring.
    (Patent Document 7, a bactericidal activity) [0014] In addition, Patent Document 8 describes the following compound (page 40, Compound No. 22). However, Patent Document 8 does not describe a compound having an amino group at position 2 of the pyridine ring.
    (Patent Document 8, a bactericidal activity) [0015] On the other hand, Patent Documents 9 to 14 specifically describe the following compounds endowed with pharmaceutical activities. In detail, Patent Document 9 describes the following
    5/28 compound (page 42, Example 186). However, Patent Document 9 does not describe a compound having an amino group at position 2 of the pyridine ring. In addition, the compound in Patent Document 9 is only presented as a pharmaceutically active substance.
    (Patent Document 9, a pharmaceutical activity) [0016] In addition, Patent Document 10 specifically describes the following compound (page 32, the compound on the right in the reaction scheme of step 3). However, this compound is only described as a reaction intermediate, and Patent Document 10 describes a compound having an amino group at position 2 of the pyridine ring.
    (Patent Document 10, a pharmaceutical activity) [0017] Patent Document 11 describes the following compound as a pro-3-nicotinoil (page 17). However, Patent Document 11 does not describe a compound having an amino group at position 2 of the pyridine ring. In addition, the compound in Patent Document 11 is only described as a pharmaceutically active substance.
    (Patent Document 11, a pharmaceutical activity) [0018] Patent Document 12 describes the following compound (page 51, E step 1). However, Patent Document 12 describes this
    6/28 compound only as an intermediate product, but does not describe a compound that has an amino group at position 2 of the pyridine ring. In addition, the compound of Patent Document 11 is only described as a pharmaceutically active substance.
    (Patent Document 12, a pharmaceutical activity) [0019] Patent Document 13 describes the following compound (page 56 (I-17-B)). However, Patent Document 13 does not describe a compound having an amino group at position 2 of the pyridine ring. In addition, the compound in Patent Document 13 is only described as a pharmaceutically active substance.
    (Patent Document 13, a pharmaceutical activity) [0020] Patent Document 13 describes the following compound (page 93, the synthesis scheme). However, Patent Document 13 describes this compound as a single intermediate, but does not describe a compound having an amino group at position 2 of the pyridine ring. In addition, the compound in Patent Document 13 is only described as a pharmaceutically active substance.
    (Patent Document 14, a pharmaceutical activity)
    7/28
    [0021] Non-Patent Document 1 refers to a compound
    pharmaceutically active which is used as a therapeutic agent for Chagas disease. Non-Patent Document 1 describes a pharmaceutically active compound having a phenoxybenzyloxy backbone. However, Non-Patent Document 1 does not describe a compound having this structure into which 2-aminonicotinic acid is introduced. PREVIOUS TECHNICAL DOCUMENTS
    Patent Document
    [0022] Patent Document 1: JP-A-2010-083861 [0023] Patent Document 2: WO 2008/082490 [0024] Patent Document 3: WO 2004/056735 [0025] Patent Document 4: WO 2002/002515 [0026] Patent Document 5: WO 2000/015615 [0027] Patent Document 6: JP-A-2004-051628 [0028] Patent Document 7: WO 1994/029267 [0029] Patent Document 8: WO 1998/033772 [0030] Patent Document 9: EP 1995-650961 [0031] Patent Document 10: WO 1998/057946 [0032] Patent Document 11: WO 2003/101980 [0033] Patent Document 12: WO 2007/133561 [0034] Patent Document 13: WO 2010/029461 [0035] Patent Document 14: WO 2011/083304
    Non-patent document
    [0036] Non-Patent Document 1: Joumal of Medicinal Chemistry,
    43, page 1826 (2000)
    SUMMARY OF THE INVENTION
    Problem to be solved
    [0037] The present invention is to provide a new compound
    useful for controlling a wide variety of bacteria, and in particular for
    8/28 provide a compound that exhibits a high control effect on a wide variety of bacteria that are tolerant to conventional bactericides, as well as to provide a compound that also has a low dose effect, and therefore has a high safety with fewer problems, such as residual toxicity, environmental pollution and the like.
    Means to solve the problem [0038] The present inventors have carried out intensive studies to solve the above problem, and, as a result, have found that the derivative of the 2-aminonicotinic acid ester defined by the following formula has the properties that can satisfy the above requirements, and thus completed the present invention.
    [0039] That is, the present invention relates to a 2-aminonicotinic acid ester derivative represented by the following formula [I]:
    R 3 OR 4
    NH 2
    [I] (where:
    R 1 represents a hydrogen atom or a C 1-4 alkyl group,
    R 2 represents a hydrogen atom, a C1-C4 alkyl group, or R 1 and R 2 are combined together to form:
    or
    R 3 represents a hydrogen atom or a C 1-4 alkyl group,
    9/28
    R 4 represents a hydrogen atom, a cyano group or a C1-C4 alkyl group,
    R 5 and R 6 independently represent a hydrogen atom, a halogen atom, a C1-C4 alkyl group, a C1-C4 alkoxy group, a C1-C4 alkylthio group, a C1-C4 alkylsulfinyl group, a CiC4 group alkylsulfonyl, a nitro group, a cyano group, a C1-4 haloalkyl group, a C1-C4 alkoxy halogen group or a C1-C4 haloalkyl group
    A and B independently represent a methyl group (CH) or a nitrogen atom (hereinafter also referred to as the present compound), as well as a bactericide comprising the same as an active ingredient.
    EFFECTS OF THE INVENTION [0040] The present compound has an excellent effect on a wide variety of bacteria.
    EMBODIMENTS FOR CARRYING OUT THE INVENTION [0041] Hereinafter, the present invention will be described in more detail.
    [0042] In the present compound represented by the formula [I], the C1-C4 alkyl groups represented by R 1 , R 2 , R 3 , R 5 and R 6 include, for example, a methyl group, an ethyl group, a group n-propyl, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group and the like. The halogen atoms represented by R 5 and R 6 include, for example, a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
    [0043] C1-C4 alkoxy groups represented by R 5 and R 6 include, for example, a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, an isobutoxy group, an sec-butoxy group and a tert-butoxy group.
    [0044] The C1-C4 alkylthio represented by R 5 and R 6 include, for example
    For example, a methylthio group, an ethylthio group, a n-propylthio group, an isopropylthio group, an n-butylthio group, an iso-butylthio group, a sec-butylthio group, and a tert-butylthio group.
    [0045] C1-C4 alkylsulfinyl groups represented by R 5 and R 6 include, for example, a methylsulfinyl group, an ethylsulfinyl group, an n-propylsulfinyl group, an isopropylsulfinyl group, an n-butylsulfinyl group, an isobutylsulfinyl group, sec-butylsulfinyl group, and a tert-butylsulfinyl group.
    [0046] C1-C4 alkylsulfonyl groups represented by R 5 and R 6 include, for example, a methylsulfonyl group, an ethylsulfonyl group, an n-propylsulfonyl group, an isopropylsulfonyl group, an nbutylsulfonyl group, an isobutylsulfonyl group, a sec group -butylsulfonyl and a tert-butylsulfonyl group.
    [0047] The haloalkyl C1-C4 groups represented by R 5 and R 6 include, for example, a monofluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a monochloromethyl group, a dichloromethyl group, a trichloromethyl group, a monobromomethyl group, dibromomethyl group, a tribromomethyl group, a 1-fluoroethyl group, a 2-fluoroethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a 2-chloro-2,2-difluoroethyl group, a group 1-chloroethyl, a group 2-chloroethyl, a group 2,2-dichloroethyl, a group 2,2,2-trichloroethyl, a group 1bromoethyl, a group 2-bromoethyl, a group 2,2-dibromoethyl, a group
    2,2,2-tribromoethyl, a 2-iodoethyl group, a pentafluoroethyl group, a 3-fluoropropyl group, a 3-chloropropyl group, a 3-bromopropyl group, a 1,3-difluoro-2-propyl group, a group 3,3,3-trifluoropropyl, a group
    1.3- dichloro-2-propyl, a 1,1-l, l-trifluoro-2-propyl group, a l-chloro-3fluoro-2-propyl group, a 1,1,1,3,3,3-hexafluoro- 2-propyl, a group
    1.1.1.3.3.3- hexafluoro-2-chloro-2-propyl, a 2,2,3,3,3-pentafluoropropyl group, a heptafluoroisopropyl group, a heptafluoro-n group
    11/28 propyl, a 4-fluorobutyl group, a 4,4,4-trifluorobutyl group, a nonafluoro-n-butyl group, and a nonafluoro-2-butyl group.
    [0048] C1-C4 haloalkoxy groups represented by R 5 and R 6 include, for example, a monofluoromethoxy group, a difluoromethoxy group, a trifluoromethoxy group, a monochloromethoxy group, a dichloromethoxy group, a trichloromethoxy group, a monobromomethoxy group, dibromomethoxy group, a tribromomethoxy group, a 1-fluoroethoxy group, a 2-fluoroethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a 2-chloro-2,2-difluoroethoxy group, a 1-chloroethoxy group, 2-chloroethoxy group, 2,2-dichloroethoxy group, 2,2,2-trichloroethoxy group, 1-bromoethoxy group, 2-bromoethoxy group, 2,2-dibromoethoxy group, 2 group , 2,2-tribromoethoxy, a 2-iodoethoxy group, a pentafluoroethoxy group, a 3-fluoropropoxy group, a 3-chloropropoxy group, a 3bromopropoxy group, a 1,3-difluoro-2-propoxy group, a 3.3 group , 3trifluoropropoxy, a 1,3-dichloro-2-propoxy group, a 1,1-trifluoro-2propoxy group, a l-chloro-3-fluoro-2-propoxy group, a group 1,1,1,3 , 3,3hexafluoro-2-propoxy, a group po l, l, l, 3,3,3-hexafluoro-2-chloro-2-propoxy, a 2,2,3,3,3-pentafluoropropoxy group, a heptafluoroisopropoxy group, a heptafluoro-n-propoxy group, a 4-fluorobutoxy group, 4,4,4trifluorobutoxy group, nonafluoro-n-butoxy group, and nonafluoro-2butoxy group.
    The haloalkylthio groups represented by R 5 and R 6 include, for example, a monofluoromethylthio group, a difluoromethylthio group, a trifluoromethylthio group, a monochloromethylthio group, a dichloromethylthio group, a trichloromethylthio group, a monobromomethylthio group, a dibromomethio group a tribromomethylthio group, a 1-fluoroethylthio group, a 2-fluoroethylthio group, a 2,2-difluoroethylthio group, a 2,2,2trifluoroethylthio group, a 2-chloro-2,2-difluoroethylthio group, a 1-chloroethylthio group, a 2-chloroethylthio group, a 2,2-dichloroethylthio group, a 2,2,2
    12/28 trichlorethylthio, a 1-bromoethylthio group, a 2-bromoethylthio group, a
    2,2-dibromoethylthio, a 2,2,2-tribromoethylthio group, a 2-iodoethylthio group, a pentafluoroethylthio group, a 3-fluoropropylthio group, a 3-chloropropylthio group, a 3-bromopropylthio group, a 1,3-difluoro- 2-propylthio, a 3,3,3-trifluoropropylthio group, a 1,3-dichloro-2-propylthio group, a 1,1-l-trifluoro-2-propylthio group, a l-chloro-3-fluoro- 2-propylthio, a 1,1,3,3-hexafluoro-2-propylthio group, a 1,1,3,3-hexafluoro-2-chloro2-propylthio group, a 2 group, 2,3,3,3-pentafluoropropylthio, a heptafluoroisopropylthio group, a heptafluoro-n-propylthio group, a 4fluorobutylthio group, a 4,4,4-trifluorobutylthio group, a nonafluoro-nbutylthio group, and a nonafluoro-2-butylthio group .
    [0050] In addition, R 4 represents a hydrogen atom, a cyano group or a C1-C4 alkyl group, and examples of C1-C4 alkyl groups include alkyl groups represented by R 1 , R 2 , R 3 , R 5 and R 6 .
    [0051] The present compound is a new compound that has not been described in any prior art document and can be produced, for example, according to the following reaction scheme from known starting compounds.
    Reaction scheme
    R 4
    [m]
    (where, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , A and B are the same as defined in formula [I] above).
    [0052] The 2-aminonicotinic acid ester derivative represented by the general formula [I] of the present invention can be produced by reacting the 2-aminonicotinic acid derivative represented by the general formula [II] with the alcohol derivative represented by the general formula [ III] in an inert solvent in the presence of a condensing agent and a base.
    13/28 [0053] The compounds [II] and [III] here are already known compounds or compounds that can be easily synthesized from compounds known to those skilled in the art.
    [0054] The reaction is conducted at a reaction temperature in the range normally -20 ° C - 120 ° C, preferably 0 ° C - 40 ° C, during a reaction time in the range normally 0.2 hours at 24 hours, preferably 1 hour to 5 hours. The phenoxybenzyl alcohol derivative represented by the general formula [III] is normally used in the range of 1 to 5 times per mol, preferably 1 to 1.5 times per mol by the 2-aminonicotinic acid derivative represented by the general formula [II] .
    [0055] Examples of the condensing agents used in the reaction include, for example, diethyl phosphorocyanidate (DEPC), carbonyldiimidazole (CDI), 1,3-dicyclohexylcarbodiimide (DCC), l-ethyl-3- (3-dimethylaminopropyl) carbodiimide, chloroformiates, 2-chloro-1-methylpyridinium and the like, and the amount of the condensing agent used is usually in the range of 1 to 3 times per mole, preferably 1 to 1.5 times per mole by acid derivative 2 -aminonicotinic represented by the general formula [II].
    [0056] The bases include, for example, inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate and potassium bicarbonate; acetates such as sodium acetate and potassium acetate; metal alkoxides, such as potassium tbutoxide, sodium methoxide, sodium ethoxide; tertiary amines, such as triethylamine, diisopropylethylamine and 1,8-diazabicyclo [5.4.0] undec-7eno; nitrogen-containing aromatic compounds such as pyridine, dimethylaminopyridine and the like. The amount of base used is normally in the range of 1 to 10 times in mole, preferably 1 to 2 times per mole per mole of the 2-aminonicotinic acid derivative represented by the general formula [II].
    [0057] A solvent may or may not be used in the reaction, but if
    14/28 a solvent is used, the solvent is not particularly limited as long as it does not significantly inhibit the reaction. A wide variety of solvents can be used and suitable examples. The solvents to be used include, for example, cyclic ethers or chain such as dimethyl ether, diethyl ether, diisopropyl ether, dibutyl ether, tetrahydrofuran and dioxane; aromatic hydrocarbons such as benzene, toluene and xylene; halogenated hydrocarbons, such as methylene chloride, chloroform, carbon tetrachloride; nitriles such as acetonitrile; esters such as methyl acetate, ethyl acetate and butyl acetate; polar solvents, such as N, N-dimethylformamide, N, N-dimethylacetamide, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolidinone; and the like. These inert solvents can be used alone or in a mixture.
    [0058] After the reaction, the desired compound can be easily isolated from the reaction system containing it using a conventional method. The desired compound can be prepared by purification by, for example, recrystallization, column chromatography and the like.
    [0059] The 2-aminonicotinic acid derivative represented by the general formula [II] used for the reaction can be easily synthesized from a known compound, for example, according to the method described in JP-A-2010-083.861 ( Patent Document 1).
    [0060] The alcohol derivative represented by the general formula [III] used for the reaction can be easily synthesized from a known compound, for example, according to the method described in the Joumal of Medicinal Chemistry, Vol. 43, page 1826 ( 2000) (Non-Patent Document 1).
    [0061] The present compound can be used to control diseases of, fruit trees, for example, an avocado tree, an apricot tree, a fig tree, an iyokan orange tree, an ume tree, a mandarin tree
    15/28 satsuma, a cherry tree, a persimmon tree, a kabosu tree, a kiwi tree, a plum tree, a pear tree, a tankan mandarin tree, a dekopon mandarin tree, an Asian pear tree, a summer orange tree, a nectarine tree, a hassaku orange tree, a papaya tree, a loquat tree, a grape tree, a grapefruit tree, a mango tree, a peach tree, a cider tree, an apple tree, a lemon tree and similar: grains, for example, barley, wheat, paddy rice, a corn, an adlay, a rye, Okabo (rice grown in dry matter) and the like; potatoes, for example, sweet potatoes, the potato, an edible colocasia, a yam and the like; vegetables, for example, an azuki bean, a strawberry, a common bean, a pea, an okra, a turnip, a pumpkin, a cabbage, a cucumber, a burdock, a cowpea, a pickling melon, a watermelon, a celery, a broad bean, a radish, a soy, an onion, a beet, a pepper, a wax gourd, a tomato, an eggplant, a bitter melon, a carrot, a leek, a Chinese cabbage, a parsley , a pepper, sponge cucumber, a melon, a lettuce and the like; industrial crops, for example, sugar cane, a lawn, tobacco, tea, rapeseed, hopand and the like; flowering plants, for example, a hydrangea, a carnation, a gerbera, a gazania, a chrysanthemum, a dandelion, a marigold, a sage, a perennial soap, a sweet pea, a statice, a saintpaulia , a dahlia, a fléolo, delphinium, a prairie gentian, a verbena, a sunflower, a rose, a begonia, a petunia, a poinsettia, a lilac, a gentian, a rosemary and the like; trees, for example, acacias, maple, holm oaks, a katsura, a paulownia, a Keyaki, cherry trees, chinkapins, azaleas, camellias, oaks, alders and willows.
    [0062] Diseases to be treated include fungi, bacteria and phytopathogenic actinomycetes, and especially include, Pyricularia oryzae, Cochliobolus miyabeanus, Rhizoctonia solani, Burkholderia glumae,
    16/28
    Xanthomonas oryzae pv. oryzae, Acidovorax avenae subsp. avenae, Erinia pineapple, Pseudomonas fuscovaginae, Burkholderia plantarii and the like of a rice plant; Erysiphe graminis, Gibberella zeae, Puccinia striiformis, P. graminis, P. recondita, P. hordei, Typhula sp, Micronectriella nivalis, Ustilago tritici, U. nuda, Tilletia caries, Pseudocercosporella herpotrichoides, Rhynchosporum triapsis teres, [0063] Helminthosporium zonatum Ikata, Pseudomonas syringae pv.
    Japonica and the like of barley or wheat; Diaporthe citri, Elsinoe fawcetti, Penicillium digitatum, P. italicum, Phytophthora citrophthora, P. nicotianae, Phyllosticta citricarpa, Xanthomonas campestris pv. citri and the like of citrus fruits; Monilinia mali, Waltz mali, Podosphaera leucotricha, Alternaria mali, Venturia inaequalis, Mycospherella pomi, Colletotrichum acutatum, Botryosphaeria berengeriana, Gymnosporangium yamadae, Monilinia fructicola and the like of an apple tree; Venturia nashicola, V. pirina, Alternaria kikuchiana, Gymnosporangium haraeanum, Monilinia fructigena and the like of an Asian pear tree; Monilinia fructicola, Cladosporium carpophilum, [0064] Phomopsis sp, Xanthomonas campestris pv. pruni and the like of a peach tree; Elsinoe ampelina, Colletotrichum acutatum, Uncinula necator, Phakopsora ampelopsidis, Guignardia bidwellii, Plasmopara viticola, Monilinia fructigena, Cladosporium viticolum, Agrobacterium viris and the like of a grape tree; Gloeosporium kaki, Cercospora kaki, Mycoshaerella nawae and the like of a persimmon tree;
    [0065] Cercospora kikuchii, Elsinoe glycines, Diaporthe phaseolorum var. oyae, Pseudomonas savastanoi pv. glycinea, Xanthomonas campestris pv.glycines and the like of a soybean; Colletotrichum lindemthianum, Pseudomonas pv savastanoi. phaseolicola, Xanthomonas campestris pv.
    17/28
    Phaseoli and the like of a bean; Cercospora personata, Cercospora arachidicola and the like of a peanut; Erysiphe pisi and the like of a pea; Colletotrichum lagenarium, Sphaerotheca fuliginea, Oidiopsis taurica, Didymella bryoniae, Fusarium oxysporum, Pseudoperonospora cubensis, Phytophthora sp., Pythium sp., Pseudomonas syringae pv. lachrymans, Xanthomonas campestris pv. cucuribitae and similar melons; Alternaria solani, Cladosporium fulvum, Phytophthora infestans, Ralstonia solanacearum, [0066] Clavibacter michiganense subsp. michiganense, Pseudomonas corrugata, Erwinia carotovora subsp. Carotovora and the like of a tomato; Phomopsis vexans, Erysiphe cichoracearum, Ralstonia solanacearum and the like of an eggplant; Alternaria japonica, Cercosporella brassicae, Xanthomonas campestris pv. campestris, Erwinia carotovora subsp. carotovora, Pseudomonas syringae pv. marginalis and similar vegetables of the cruciferous family; Puccinia allii and the like of a leek; Alternaria solani, Phytophthora infestans, Rhizoctonia solani, Erwinia carotovora subsp. carotovora, Erwinia carotovora subsp. atroseptica, Ralstonia solanacearum, Streptomyces mange, Streptomyces acidiscabies and the like of a potato; Sphaerotheca humuli, Ralstonia solanacearum, Pseudomonas marginalis pv. marginalis, Xanthomonas campestris, Xanthomonas fragariae and the like of a strawberry; Exobasidium reticulatum, Elsinoe leucospila, Pseudomonas syringae pv. theae, Ralstonia solanacearum, Xanthomonas campestris pv. theicola and the like of a tea plant;
    [0067] Longipes Alternaria, Erysiphe cichoracearum, Colletotrichum tabacum, Peronospora tabacina, Phytophthora nicotianae, Erwinia carotovora subsp. Carotovora and the like of a tobacco; Cercospora beticola, Aphanomyces cochliodes and the like of a beet; Alternaria dauci, Rhizobacter dauci, Streptomyces scabies and the like of a carrot;
    18/28
    Diplocarpon rosae, Sphaerotheca pannosa, Agrobacterium tumefaciens and the like of a rose; Septoria chrysanthemi-indici, Puccinia horiana, Agrobacterium tumefaciens and the like of a chrysanthemum; Botrytis cinerea, Sclerotinia sclerotiorum and the like from different cultures, but diseases for the bacteria described here are not limited.
    [0068] The present compound can be used in a wide variety of formulations. In order to prepare these formulations, a wide variety of pesticide adjuvants used conventionally in the technical field of bactericidal agents for agriculture and horticulture can be used appropriately. Bactericidal formulations for agriculture and horticulture include, for example, an emulsifiable concentrate, a wettable powder, a water-dispersible granulate, a water-soluble powder, a soluble concentrate, a dusting powder, a suspension concentrate (fluid) , a dry fluid, a fine granulate, a granulate, a tablet, a solution in oil, a propellant, an aerosol and the like. Naturally, one or more compounds present can be combined as an active ingredient.
    [0069] Such pesticide adjuvants can be used for the purposes, for example, of improving the effects of bactericidal agents for agriculture and horticulture, and of improving dispersion stability and the like. Pesticide adjuvants include, for example, a carrier (a diluent), a spreader, an emulsifier, a wetter spreader, a dispersant, a disintegrating agent and the like. Liquid carriers include, water, aromatic hydrocarbons, such as toluene and xylene, alcohols, such as methanol, butanol and glycol, ketones, such as acetone, amides such as dimethyl formamide, sulfoxides such as dimethyl sulfoxide, methyl naphthalene, cyclohexane , animal and vegetable oils, fatty acids and the like. In addition, solid carriers include, clay, kaolin, talc, diatomaceous earth, silica, calcium carbonate, montmorillonite, bentonite, feldspar,
    19/28 quartz, alumina, sawdust, nitrocellulose, starch, gum arabic and the like.
    [0070] As a dispersant and emulsifier, conventional surfactants can be used, and they include, anionic surfactants such as higher alcohol sodium sulfates, stearyl trimethyl ammonium chloride, polyoxyethylene phenyl alkyl ethers and lauryl betaine; cationic surfactants, non-ionic surfactants, amphoteric surfactants; and the like. In addition, a spreader; a wetter spreader, such as dialkyl sulfosuccinates; a binder such as carboxymethyl cellulose and polyvinyl alcohol; a disintegrator such as sodium lignosulphonate, sodium lauryl sulphate and the like can be used.
    [0071] The amount of the present compound to be contained in the bactericidal agent for agriculture and horticulture as an active ingredient is, for example, from 0.01 to 99.5% by weight, preferably from 0.5 to 90% by weight. pasta. The amount can be appropriately determined based on several conditions, such as types of formulations, methods of application and the like. The bactericidal agent for agriculture and horticulture can be prepared in such a way that it contains an active ingredient in an amount of, for example, about 0.5 to 20% by weight, preferably 1 to 10% by weight in the case of a sprinkling powder, about 1 to 90% by mass, preferably from 10 to 80% by mass, in the case of a wetting powder and about 1 - 90% by mass, preferably from 10 - 40% by mass in the case of an emulsifiable concentrate.
    [0072] In the case of an emulsifiable concentrate, for example, an emulsifiable concentrate can be prepared by mixing a solvent and a surfactant with the present compound as an active ingredient, and then the concentrate can be diluted to a concentration predetermined with water by the use to be applied. In the case of a wettable powder, the present compound as an active ingredient, a carrier
    20/28 solid and a surfactant are mixed to obtain a liquid concentrate, and then the concentrate can be diluted to a predetermined concentration with water using the application to be applied. In the case of a dusting powder, the present compound as an active ingredient, a solid carrier and the like are mixed and the resulting mixture can be applied as is, and in the case of a granule, the present compound as an active ingredient, a solid carrier, surfactant and the like are mixed and granulated to obtain a formulation that can be applied as is. In this case, however, the methods for preparing the above formulations are not limited to those described above and can be appropriately chosen by those skilled in the art depending on types of active ingredients and an application purpose and the like.
    [0073] The bactericidal agent for agriculture and horticulture can also contain an active ingredient, such as another optional bactericidal agent, an insecticide, an acaricide, herbicide, a plant growth regulator, a fertilizer, a soil conditioner and the like. mixed in addition to the present compound as an active ingredient. The methods of applying the bactericidal agent comprising the present compound is not particularly limited and its methods of application that can be used include, leaf application, application to the soil, smoking in plants, stem smoking and the like. For example, in the case of foliar application, a solution in a concentration range, for example, from 5 to 1000 ppm, preferably from 10 to 500 ppm, can be used in an applied amount of, for example, about 50 to 700 liters for 10 ares. In the case of application to the soil, a solution with a concentration range of 5 to 1000 ppm can be used in an applied amount of about 0.1 to 1 liter per 1 m 2 .
    EXAMPLES [0074] Hereinafter, the present invention will be described in more detail
    21/28 detail by reference to Examples, Preparation Examples and Examples of
    Test, but the scope of the present invention is not limited by these Examples, Preparation Examples and Test Examples at all.
    <Example 1> Synthesis of 2-phenoxybenzyl 2-aminonicotinate [0075] 0,200 g of 2-phenoxybenzyl alcohol, 0.230 g of l-ethyl-3- (3dimethylaminopropyl) carbodiimide and 0.146 g of 4-dimethylaminopyridine were added to a solution of 0.138 g of 2-aminonicotinic acid in methylene chloride, and the mixture was heated under reflux for 3 hours. After cooling to room temperature, the mixture was extracted with methylene chloride, and the aqueous layer was further extracted with methylene chloride. The organic layers were combined and dried over anhydrous sodium sulfate. After concentration under reduced pressure, the resulting residue was purified by silica gel column chromatography to obtain 0.180 g of Compound No. 1, as an oil, which is described in Table 1 below. In addition, other compounds of the present invention have been synthesized in a similar way. Table 1 below shows the compounds of the present invention that were produced in a similar manner to that of Example 1.
    Table 1
    R 5
    R 6
    22/28
    NO. R 1 R * R 3 R 4 W ιτιρ (¾) 1 H H H H 0-0 0 -Ü Oil 11 2 CH 3 H H H128-131 3 H H H H102-103 4 CHj H H H ‘V ° O 99-100 5 H H H H ΊΧΟ 116-1 18 6 f C «3 H H H τχο 107-109 7 H H H CHj ’Ό ° Ό Oil 2 > 3 CH 3 H H CHg ’Ό ° Ό Oil 3 > 3 H H H ch 3 Oil 4 ^ 10 CH g H H ch 3 ‘1X0 96-87 11 H H H CN * Ό ° Ό Oil 5 * 12 ch 3 H H CN * Ότ ° Ό 146-148 13 ch 3 H H H 0ι 0 £ Γ ' 84-9S 14 ch 3 H H H • χχσ ™ ’ 107-109 15 CHj H H H * τχσ α 111-113
    23/28 ci
    16 CH S H H H U 0 JJ 85-87 17 ch 3 H H H χχο 115-117ch 3 16 ch 3 H H H Xyò 106-108 19 CH S H H H w 89-91 20 ch 3 H H H * O o xX Hs 114-116 21 ch 3 H H H *O. 0 J7 CF ' '- β > Oil 22 ch 3 H H H 'XVO' OCF ' 129-130 23 CH a H H H161-162 24 ch 3 H H H XC 8 ”' 166-167 25 ch 3 H H H153-155 26 ch 3 H H H106-108 27 ch 3 H H H104-106 28 ch 3 H H H * ιχα ΒΓ 133-135 29 ch 3 H H H136-138 30 ch 3 H H H113-120 31 CKj H H H ’ΪΧχΤ 143-145 32 CHs H H H122-124
    24/28
    c 2 h 5 H H H CH (CH 3 ) 2 H H H ch 3 ch 3 H H c 2 h 5 ch 3 H H ch 3 H ch 3 H nH H OH H H H H H ch 3 H H H H H H H ch 3 H H H H H H H H H H H ch 3 H H H ch 3 H H H ch 3 H H H ch 3 H H H
    111-113
    73-75
    123-125
    87-89
    126-127
    148-150
    121-123
    117-119
    106-108
    83-84
    120-122
    134-136
    118-119
    120-121
    111-112
    140-142
    94-96 [0082]
    Next, Preparation Examples will be shown. We
    25/28
    Preparation Examples, parts represent parts by mass.
    Preparation Example 1: Emulsifiable concentrate [0083] A compound of the present invention (10 parts), xylene (60 parts), N-methyl-2-pyrrolidone (20 parts) and Sorpol 3005X (mixture of a nonionic surfactant and a anionic surfactant, TOHO Chemical Industry Co., Ltd., Japan, a trade name) (10 parts) were mixed uniformly and dissolved to give an emulsifiable concentrate.
    Preparation Example 2: Wetting powder - 1 [0084] The compound of the present invention (20 parts), Nipsil NS-K (white carbon, Tosoh Silica Corporation, Japan, a trade name) (20 parts), kaolin clay (kaolinite , Takehara KAGAKU KOGYO CO., LTD., Japan, a trade name) (70 pieces), Sanx P-252 (sodium lignosulfonate, NIPPON PAPER INDUSTRIES CHEMICAL Div., Japan, trade name) (5 parts) and Runox P- 65L (an alkylaryl sulfonate, TOHO Chemical Industry Co., Ltd., Japan, a trade name) (5 parts) were uniformly mixed and ground by an air mill to obtain a wettable powder.
    Preparation Example 3: Wetting powder - 2 [0085] The compound of the present invention (20 parts), Nipsil NS-K (20 parts), kaolin clay (50 parts), RunoxlOOOC (a condensed salt of naphthalenesulfonic acid, TOHO Chemical Industry Co., Ltd., Japan, a trade name) (5 parts) and Sorpol 5276 (a nonionic surfactant, TOHO Chemical Industry Co., Ltd., Japan, a trade name) (5 parts) were uniformly mixed and ground by means of an air mill to obtain a wettable powder.
    Preparation Example 4: Suspension Concentrate (Flowable) - 1 [0086] The compound of the present invention (20 parts) was dispersed in a previously mixed mixture of propylene glycol (5 parts), Sorpol
    26/28
    7933 (an anionic surfactant, TOHO Chemical Industry Co., Ltd., Japan, a trade name) (5 parts) and water (50 parts), to make a slurry mixture, and then the slurry mixture was wet milled by means of Dyno-Mill (Shinmaru Enterprises Corporation, Japan), and to the resulting material, a well-mixed dispersion of xanthan gum (0.2 parts) in water (19.8 parts) was added to obtain a suspension concentrate (flowable).
    Preparation Example 5: Suspension Concentrate (Flowable) - 2 [0087] A compound of the present invention (20 parts), Newkalgen
    FS-26 (a mixture of dioctyl sulfosuccinate and polyoxyethylene tristyryl phenyl ether, TAKEMOTO OIL & FAT Co. Ltd., Japan, a trade name) (5 parts), propylene glycol (8 parts) and water (50 parts) were pre -mixed to obtain a slurry mixture and then the slurry mixture was wet milled by means of Dyno-Mill (Shinmaru Enterprises Corporation, Japan). Then, the xanthan gum (0.2 parts) was mixed well and dispersed in water (16.8 parts) to give a gelatinous material and the gelatinous material was sufficiently mixed with the ground slurry to obtain a suspension concentrate. (flowable).
    [0088] Next, the following Test Examples will prove that the present compounds are useful as an active ingredient in a bactericide. In Test Examples, the present compounds used are shown by their numbers of the compounds described in Table 1, and a compound used as a comparative control is shown by the following compound (a compound described in the Examples of Patent Document 1).
    ç
    Compound A (Patent Document 1)
    Test Example 1: A test on Botrytis cinerea (gray mold) from a cucumber
    27/28 [0089] A cucumber plant (a plant variety: Sagami
    Han-shiro) 12 days after sowing was prepared for the test. Parts of the cotyledons of the cucumber plant were cut leaving about 2 cm of their rachis. In addition, a plastic box with a size of 32 cm x 24 cm x 4.5 cm (length x width x height), at the bottom of which a paper towel sufficiently moistened with water was established, and on the paper towel a mesh with legs was placed, was prepared. In the mesh, the cut-out parts described above of cotyledons were placed in such a way that the leaves were horizontal. For the central part of each cotyledon, 50 μΐ of a spore suspension (1 x 10 6 spores / ml) of Botrytis cinerea, from a cucumber was added dropwise. Then, each cotyledon was covered with a 6 mm diameter paper disc. In addition, an emulsion prepared according to Preparation Example 1 above was diluted with a 0.02% aqueous solution of Tween 20 in demineralized water to prepare a diluent of a predetermined concentration. 50 μΐ of diluent was dropped on each paper disc. The plastic box with a lid was placed under a 20 ° C condition for 72 hours, and then the diameter of each lesion was measured and the control rate for Botrytis cinerea (gray mold) from a cucumber was calculated from according to the following equation. The results are shown in Table 1.
    Control rate (%) = [(diameter of the lesion in the treatment region / diameter of the lesion in the non-treatment region)] x 100
    Table 2
    28/28
    BdtrytiS Cinerea (gray mold) from a cucumber
    NO. Control cone (ppm) (¾)
    5 25 100 6 25 100 13 25 100 14 25 100 15 25 100 17 25 100 18 25 100 19 25 100 20 25 100 27 25 100 34 25 100 35 25 100 36 25 100 40 25 100 41 25 100 43 25 100 4S 25 100 47 25 100 49 25 100 THE 25 54
    [0090] As shown in Table 2 above, the present compound exhibits a higher bactericidal activity when compared to that of compound A.
    权利要求:
    Claims (2)
    [1]
    1. Derived from 2-aminonicotinic acid ester, characterized by the fact that it is represented by the following formula [I]:
    R 3 OR 4
    NH 2 [I] (where:
    R 1 represents a hydrogen atom or a C1-C4 alkyl group, R 2 represents a hydrogen atom, a C 1 C 4 alkyl group, or R 1 and R 2 are combined together to form:
    or
    R 3 represents a hydrogen atom or a C 1-4 alkyl group,
    R 4 represents a hydrogen atom, a cyano group or a C1-C4 alkyl group,
    R 5 and R 6 independently represent a hydrogen atom, a halogen atom, a C1-C4 alkyl group, a C1-C4 alkoxy group, a C1-C4 alkylthio group, a C1-C4 alkylsulfinyl group, a CiC4 group alquilsulfonila, a nitro group, a cyano group, a haloalkyl group CiC 4, a halogeno C1-C4 alkoxy or C1-C4 haloalkylthio,
    A and B independently represent a methyl group (CH) or a nitrogen atom).
    [2]
    2. Bactericide, characterized by the fact that it comprises the 2-aminonicotinic acid ester derivative as defined in claim 1 as an active ingredient.
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    同族专利:
    公开号 | 公开日
    CA2877235A1|2014-01-09|
    RU2015103515A|2016-08-20|
    UA111542C2|2016-05-10|
    WO2014006945A1|2014-01-09|
    AU2013284775A1|2015-01-29|
    CN104520273B|2016-08-24|
    ES2665561T3|2018-04-26|
    CN104520273A|2015-04-15|
    BR112014032873A2|2017-06-27|
    IN2014DN10806A|2015-09-04|
    PT2871180T|2018-05-08|
    MA37825B1|2016-06-30|
    CA2877235C|2016-09-20|
    EP2871180A1|2015-05-13|
    CL2014003643A1|2015-07-31|
    CO7240428A2|2015-04-17|
    RU2599725C2|2016-10-10|
    US20150175551A1|2015-06-25|
    HUE037765T2|2018-09-28|
    PL2871180T3|2018-08-31|
    KR20150042781A|2015-04-21|
    MA20150409A1|2015-11-30|
    JPWO2014006945A1|2016-06-02|
    EP2871180B1|2018-03-21|
    ZA201500742B|2016-09-28|
    EP2871180A4|2016-02-24|
    KR101629767B1|2016-06-13|
    AU2013284775B2|2015-09-17|
    US9096528B2|2015-08-04|
    JP6114958B2|2017-04-19|
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    法律状态:
    2018-03-27| B06F| Objections, documents and/or translations needed after an examination request according art. 34 industrial property law|
    2018-12-04| B15K| Others concerning applications: alteration of classification|Free format text: AS CLASSIFICACOES ANTERIORES ERAM: C07D 213/80 , A01N 43/40 , A01P 3/00 Ipc: C07D 213/80 (1974.07), C07D 215/54 (1974.07), C07D |
    2019-01-08| B09A| Decision: intention to grant|
    2019-02-12| B16A| Patent or certificate of addition of invention granted|Free format text: PRAZO DE VALIDADE: 20 (VINTE) ANOS CONTADOS A PARTIR DE 02/04/2013, OBSERVADAS AS CONDICOES LEGAIS. (CO) 20 (VINTE) ANOS CONTADOS A PARTIR DE 02/04/2013, OBSERVADAS AS CONDICOES LEGAIS |
    优先权:
    申请号 | 申请日 | 专利标题
    JP2012150421|2012-07-04|
    JP2012-150421|2012-07-04|
    PCT/JP2013/060061|WO2014006945A1|2012-07-04|2013-04-02|2-aminonicotinic acid ester derivative and bactericide containing same as active ingredient|
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