JPH04124107A - Control agent of phycomycete plant disease, containing 2-chloronicotinic acid amide derivative as active ingredient - Google Patents
Control agent of phycomycete plant disease, containing 2-chloronicotinic acid amide derivative as active ingredientInfo
- Publication number
- JPH04124107A JPH04124107A JP24265490A JP24265490A JPH04124107A JP H04124107 A JPH04124107 A JP H04124107A JP 24265490 A JP24265490 A JP 24265490A JP 24265490 A JP24265490 A JP 24265490A JP H04124107 A JPH04124107 A JP H04124107A
- Authority
- JP
- Japan
- Prior art keywords
- group
- active ingredient
- acid amide
- agent
- plant diseases
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 201000010099 disease Diseases 0.000 title claims abstract description 23
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims abstract description 23
- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 20
- 239000004480 active ingredient Substances 0.000 title claims abstract description 10
- ZQZAHPFFZWEUCL-UHFFFAOYSA-N 2-chloropyridine-3-carboxamide Chemical class NC(=O)C1=CC=CN=C1Cl ZQZAHPFFZWEUCL-UHFFFAOYSA-N 0.000 title 1
- -1 morpholino, 2, 6- dimethylmorpholino, pyridyl Chemical group 0.000 claims abstract description 28
- DEMJOLRJLACBRX-UHFFFAOYSA-N 2-chloropyridine-4-carboxamide Chemical class NC(=O)C1=CC=NC(Cl)=C1 DEMJOLRJLACBRX-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000005843 halogen group Chemical group 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 5
- 241000233866 Fungi Species 0.000 claims description 12
- 241000195493 Cryptophyta Species 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000001064 morpholinomethyl group Chemical group [H]C([H])(*)N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims description 3
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 31
- 230000000694 effects Effects 0.000 abstract description 13
- 241000233679 Peronosporaceae Species 0.000 abstract description 12
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 abstract description 2
- 125000003943 azolyl group Chemical group 0.000 abstract description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 abstract description 2
- 125000001425 triazolyl group Chemical group 0.000 abstract description 2
- DBTDEFJAFBUGPP-UHFFFAOYSA-N Methanethial Chemical compound S=C DBTDEFJAFBUGPP-UHFFFAOYSA-N 0.000 abstract 1
- 125000006193 alkinyl group Chemical group 0.000 abstract 1
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- 230000000813 microbial effect Effects 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- 241000196324 Embryophyta Species 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000009472 formulation Methods 0.000 description 11
- 239000002904 solvent Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
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- 230000001225 therapeutic effect Effects 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
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- 239000012044 organic layer Substances 0.000 description 5
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000003905 agrochemical Substances 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
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- 230000003902 lesion Effects 0.000 description 4
- 238000000034 method Methods 0.000 description 4
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- 150000002825 nitriles Chemical class 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- NPRZWOJTSGFSBF-UHFFFAOYSA-N 2-chloropyridine-4-carbonyl chloride Chemical compound ClC(=O)C1=CC=NC(Cl)=C1 NPRZWOJTSGFSBF-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 3
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- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 240000006365 Vitis vinifera Species 0.000 description 3
- 235000014787 Vitis vinifera Nutrition 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 239000007884 disintegrant Substances 0.000 description 3
- 239000000417 fungicide Substances 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 239000004563 wettable powder Substances 0.000 description 3
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- 241001223281 Peronospora Species 0.000 description 2
- 241000233614 Phytophthora Species 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
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- 239000002671 adjuvant Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000012752 auxiliary agent Substances 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
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- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
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- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 description 2
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- 239000012442 inert solvent Substances 0.000 description 2
- 238000011081 inoculation Methods 0.000 description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
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- GGHCWJWUOSNCSK-UHFFFAOYSA-N (2-chloropyridin-4-yl)methanamine Chemical group NCC1=CC=NC(Cl)=C1 GGHCWJWUOSNCSK-UHFFFAOYSA-N 0.000 description 1
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- VFQXVTODMYMSMJ-UHFFFAOYSA-N isonicotinamide Chemical class NC(=O)C1=CC=NC=C1 VFQXVTODMYMSMJ-UHFFFAOYSA-N 0.000 description 1
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- ZQEIXNIJLIKNTD-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alaninate Chemical compound COCC(=O)N(C(C)C(=O)OC)C1=C(C)C=CC=C1C ZQEIXNIJLIKNTD-UHFFFAOYSA-N 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- DVEKCXOJTLDBFE-UHFFFAOYSA-N n-dodecyl-n,n-dimethylglycinate Chemical compound CCCCCCCCCCCC[N+](C)(C)CC([O-])=O DVEKCXOJTLDBFE-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000004967 organic peroxy acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- REXRPUZAHNQWAM-KCOFNFEMSA-J zinc;manganese(2+);methyl (2s)-2-(n-(2-methoxyacetyl)-2,6-dimethylanilino)propanoate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[Zn+2].[S-]C(=S)NCCNC([S-])=S.[S-]C(=S)NCCNC([S-])=S.COCC(=O)N([C@@H](C)C(=O)OC)C1=C(C)C=CC=C1C REXRPUZAHNQWAM-KCOFNFEMSA-J 0.000 description 1
Landscapes
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は一部新規な化合物を含む2−クロロイソニコチ
ン酸アミド誘導体を有効成分として含有することを特徴
とする藻菌類による植物病害防除剤に関するものである
。[Detailed Description of the Invention] [Industrial Application Field] The present invention provides an agent for controlling plant diseases caused by algae and fungi, which is characterized by containing as an active ingredient a 2-chloroisonicotinic acid amide derivative containing a partially novel compound. It is related to.
現在、藻菌類による植物病害に対してはキャブタン、キ
ャプタホル、ジチオカーバメート系殺菌側、クロロタロ
ニルなどが広く用いられている。Currently, cabtane, captafol, dithiocarbamate fungicides, chlorothalonil, and the like are widely used to treat plant diseases caused by algal fungi.
しかし、これらの薬剤は予防効果が主であり、治療効果
がほとんどないことから、発病が認められてからの薬剤
処理による防除という場面には使用できないという欠点
をもっている。However, these drugs mainly have a preventive effect and have almost no therapeutic effect, so they have the disadvantage that they cannot be used for control by chemical treatment after the onset of the disease is recognized.
一方、その後開発されたアソルアラニン系12菌剤、た
とえばメタラキノルは治療効果もあわせもっでいるか、
既にその薬剤耐性菌の出現により、防除効果が低下して
きており問題上なっている。On the other hand, whether the asolalanine-based 12 fungal agents that have been developed since then, such as metallaquinol, also have therapeutic effects?
Due to the emergence of drug-resistant bacteria, the control effect has already been reduced and is becoming a problem.
2−クロロイソニコチン酸アミド誘導体に関しては、本
出願人により、特願平1−48609号公報において、
イネいもち病、イネ1葉枯葉に対して高い防除効果を示
すことが開示されているが、べと病や疫病などの藻菌類
による植物病害に対する防除効果については全く報告さ
れていない。Regarding 2-chloroisonicotinic acid amide derivatives, the present applicant has disclosed in Japanese Patent Application No. 1-48609,
Although it has been disclosed that it has a high control effect on rice blast and single-leaf defoliation of rice, there has been no report on its control effect on plant diseases caused by algal fungi such as downy mildew and late blight.
本発明は藻菌類による植物病害に対して、新しい作用性
を有し、予防効果、治療効果を示す殺菌剤を提供するこ
とを課題とする。An object of the present invention is to provide a fungicide that has a new action and exhibits preventive and therapeutic effects against plant diseases caused by algal fungi.
C1題を解決するための手段]
前記課題を解決するために、イソニコチン酸アミド誘導
体について鋭意研究した結果、一部新規化合物を含む以
下に示す一般式の化合物群がべと病や疫病などの藻菌類
による植物病Scこ対してずくれた予防効果、治療効果
を示すことを見い出し、本発明を完成させるに至った。Means for Solving Problem C1] In order to solve the above problem, as a result of intensive research on isonicotinamide derivatives, a group of compounds with the general formula shown below, including some new compounds, have been found to be effective against mildew, late blight, etc. The present inventors have discovered that the present invention exhibits excellent preventive and therapeutic effects against plant diseases caused by algae and fungi, leading to the completion of the present invention.
すなわち、本発明は一般式
%式%
〔式中、Rはハロゲン原子で置換されていてもよい低級
アルキル基、ハロゲン原子で置換されていてもよいアリ
ル基、C1〜C,アルキニル基、基−c)1.5(0)
、、R’ チオンアナトメチル基、アゾリルメチル基
、トリアゾリルメチル基、モルホリノメチル基、2,6
−ジメチルモルホリノメチル嘩、2,3−エボキンプロ
ピル基、ピリジルメチル基、2−クロロイソニコチニル
アミノメチル基または、ハロゲン原子で置換されていて
もよいヘンシル基を示し、ここでR゛は低級アルキル基
を示し、nは0または1〜2の整数を示す。]で表ねさ
れる2−クロロイソニコチン酸アミド誘導体を有効成分
として含有することを特徴とする藻菌類による植物病害
防除剤に関するものである。That is, the present invention is based on the general formula % [wherein R is a lower alkyl group optionally substituted with a halogen atom, an allyl group optionally substituted with a halogen atom, a C1-C, alkynyl group, a group - c) 1.5 (0)
,,R' thionanatomethyl group, azolylmethyl group, triazolylmethyl group, morpholinomethyl group, 2,6
-dimethylmorpholinomethyl group, 2,3-evoquinpropyl group, pyridylmethyl group, 2-chloroisonicotinylaminomethyl group, or a Hensyl group optionally substituted with a halogen atom, where R' is a lower It represents an alkyl group, and n represents 0 or an integer of 1-2. The present invention relates to an agent for controlling plant diseases caused by algal fungi, which is characterized by containing a 2-chloroisonicotinic acid amide derivative represented by the following as an active ingredient.
一般式El)において、Rがプロパルギル基以列のアル
キニル基である化合物、低級アルキルスルフィニルメチ
ル基である化合物、モルホリノメチル基である化合物、
2−クロロイソニコチニルアミノメチル基である化合物
は新規化合物である。In the general formula El), a compound in which R is an alkynyl group of the propargyl group, a lower alkylsulfinylmethyl group, a morpholinomethyl group,
Compounds that are 2-chloroisonicotinylaminomethyl groups are new compounds.
本発明の一般式CI)の化合物は以下の方法で製造する
ことができる。The compound of general formula CI) of the present invention can be produced by the following method.
I
で表わされる2−クロロイソニコチン酸クロライドを、
−綴代
%式%[
〔式中、R″はハロゲン原子で置換されていてもよい低
級アルキル基、ハロゲン原子で置換されていてもよいア
リル基、C2〜C,アルキニル基、ピリジルメチル基、
ハロゲン原子で置換されていてもよいヘンゼノル基を示
す、〕で表わされるアミン誘導体と、場合により塩基の
存在下に不活性な溶媒中で反応させることにより得られ
る。2-chloroisonicotinic acid chloride represented by I,
- % formula %[ [wherein R'' is a lower alkyl group which may be substituted with a halogen atom, an allyl group which may be substituted with a halogen atom, a C2-C, alkynyl group, a pyridylmethyl group,
It can be obtained by reacting with an amine derivative represented by ], which represents a hensenol group optionally substituted with a halogen atom, in an inert solvent, optionally in the presence of a base.
ここにいう塩基としては、トリエチルアミン、トリブチ
ルアミン、N、N−ジメチルアニリン、N−メチルモル
ホリン、ピリジン、4−ジメチルアミノピリジン等の第
3級アミン、水酸化ナトリウム、水酸化カリウム、炭酸
ナトリウム、炭酸カリウム、炭酸水素ナトリウム、水素
化ナトリウム等の無機塩基があげられる。また不活性溶
媒としては、水あるいは有機溶媒たとえばヘキサン、ヘ
プタン等の脂肪族炭化水素類、ヘンゼン、トルエン等の
芳香族炭化水素類、ノクロロメタン、クロロホルム等の
ハロゲン化炭化水素類、ジエチルエーテル、テトラヒド
ロフラン等のエーテル類、アセトン、メチルエチルケト
ン等のケトン類、アセトニトリル、プロピオニトリル等
のニトリル類酢酸エチル、プロピオン酸エステル類、ジ
メチルホルムアミド、ジメチルスルホキッド等の非プロ
トン性極性溶媒があげられ、さらに、ピリジンは上記の
塩基と溶媒を兼ねて用いることができる。また上記の溶
媒を混合して用いることもできる。反応温度および反応
時間は、−10°C〜100℃、好ましくは、O′C〜
50 ’Cの範囲、約30分〜24時間、好ましくは1
〜8時間の範囲で行われる。The bases mentioned here include tertiary amines such as triethylamine, tributylamine, N,N-dimethylaniline, N-methylmorpholine, pyridine, and 4-dimethylaminopyridine, sodium hydroxide, potassium hydroxide, sodium carbonate, and carbonic acid. Examples include inorganic bases such as potassium, sodium hydrogen carbonate, and sodium hydride. Examples of inert solvents include water or organic solvents such as aliphatic hydrocarbons such as hexane and heptane, aromatic hydrocarbons such as henzene and toluene, halogenated hydrocarbons such as nochloromethane and chloroform, diethyl ether, tetrahydrofuran, etc. ethers such as acetone, ketones such as methyl ethyl ketone, nitriles such as acetonitrile and propionitrile, aprotic polar solvents such as ethyl acetate, propionate esters, dimethylformamide, dimethyl sulfokide, and pyridine. The above base and solvent can be used together. Moreover, the above-mentioned solvents can also be used in combination. The reaction temperature and reaction time are -10°C to 100°C, preferably O'C to
50'C range, about 30 minutes to 24 hours, preferably 1
It is carried out for a period of ~8 hours.
−綴代CI)において、Rが2.3−エポキンプロビル
基の化合物は、上記方法で得られたR1がアリル基の化
合物をクロロホルム等のハロゲン化炭化水素中、m−ク
ロロ過安息香酸などの有機過酸と、室温〜100“Cで
反応させることにより得られる。- Tsuzuriyo CI), the compound in which R is a 2,3-epoquinprobyl group is prepared by adding the compound in which R1 is an allyl group obtained by the above method to an organic compound such as m-chloroperbenzoic acid in a halogenated hydrocarbon such as chloroform. Obtained by reaction with peracid at room temperature to 100"C.
一般式〔I〕においてRがR1および2,3−エポキシ
プロビル基以外の蟇である化合物は以下の各ルートで製
造することができる。Compounds in which R in the general formula [I] is a group other than R1 or a 2,3-epoxyprobyl group can be produced by the following routes.
I
I
(IV)
〔V j
SOCI□
C式中Mはカリウム、ナトリウム、アンモニウムなどの
一価の陽イオンを示し、R′は低級アルキル基を示し、
n゛は1〜2の整数に示し、Zはアゾリル基、トリアゾ
リル基、モルホリノ基、2.6−ジメチルモルホリノ基
、2−クロロイソニコチニルアミン基を示す。〕上記の
反応式で表わされるように、式CIV)で表わされるア
ミドをアルカリ金属重炭酸塩の存在下、ホルマリンと加
熱反応させることにより式(V)の化合物が得られ、こ
れをトルエン等の芳香族炭化水素類やクロロホルム等の
ハロゲン化炭化水素類を溶媒とし、塩化チオニルと加熱
反応させることにより、弐(■)の化合物が得られる。I I (IV) [V j SOCI□ C In the formula, M represents a monovalent cation such as potassium, sodium, ammonium, etc., R' represents a lower alkyl group,
n' is an integer of 1 to 2, and Z represents an azolyl group, a triazolyl group, a morpholino group, a 2,6-dimethylmorpholino group, or a 2-chloroisonicotinylamine group. ] As shown in the above reaction formula, the compound of formula (V) is obtained by heating the amide represented by formula CIV) with formalin in the presence of an alkali metal bicarbonate, and this is reacted with toluene etc. Compound 2 (■) can be obtained by heating and reacting with thionyl chloride using aromatic hydrocarbons or halogenated hydrocarbons such as chloroform as a solvent.
式CVl )の化合物をア七ト二トリル等のニトリル類
やクロロホルム等のハロゲン化炭素水素類、トルエン等
の芳香族炭化水素類を溶媒に弐MSCN(Mは前記と同
し意味を有する。〕で表わされる千オシアン酸塩と加熱
反応させることにより、式〔■〕の化合物が得られる。A compound of formula CVl) is mixed with a nitrile such as a7tonitrile, a halogenated hydrocarbon such as chloroform, or an aromatic hydrocarbon such as toluene as a solvent (M has the same meaning as above). A compound of the formula [■] is obtained by a heating reaction with a thiocyanate represented by the formula [■].
式(Vl)の化合物をア七ト二トリル等のニトリル類、
テトラヒドロフラン等のエーテル類、ジメチルホルムア
ミド等の非プロトン性極性溶媒を溶媒とし、場合により
、トリエチルアミン、ピリジン等の有機塩基、水酸化ナ
トリウム、水素化ナトリウム等の無機塩基の存在下、式
Z1([Zは前記と同し意味を有する。]で表わされる
化合物と反応させることにより一般式(IXIの化合物
が得られる。The compound of formula (Vl) is a nitrile such as a7tonitrile,
Formula Z1 ([Z has the same meaning as above.] A compound of the general formula (IXI) can be obtained.
さらに弐〔Vl)の化合物を、メタノール等のアルコー
ル類、またはアセ]・ニトリル等のニトリル類中、アル
カリ金属アルコラード、アルカリ金属水素化物、アルカ
リ金属炭酸塩等の塩基の存在下、低級アルキルチオール
類と反応させることにより、−綴代〔■〕の化合物が得
られ、この化合物をクロロホルム等のハロゲン炭化水素
溶媒中、m−クロロ過安息香酸等の有機過酸で酸化する
ことにより、−i式(Xlの化合物が得られる。Further, the compound 2 [Vl] is mixed with a lower alkylthiol in an alcohol such as methanol, or a nitrile such as acenitrile, in the presence of a base such as an alkali metal alcoholade, an alkali metal hydride, or an alkali metal carbonate. By reacting with, a compound of -Tsuzuriyo [■] is obtained, and by oxidizing this compound with an organic peracid such as m-chloroperbenzoic acid in a halogenated hydrocarbon solvent such as chloroform, -i formula (Compound Xl is obtained.
反応化合物から目的物を単離するには水洗後、有機層を
減圧濃縮する等の通常の後処理を行い、必要に応じ、さ
らに、再結晶、カラムクロマトグラフィー等により精製
を行う。To isolate the target product from the reaction compound, after washing with water, usual post-treatments such as concentration of the organic layer under reduced pressure are performed, and if necessary, further purification is performed by recrystallization, column chromatography, etc.
本発明防除剤が優れた防除効果を示す藻菌類による植物
病害としては、ブドウのべと病(P lasmopar
e viLicota) 、ウリ類のべと病(P 5
eudoperonospora cubensis)
、アブラナ科野菜のべと病(P eronosp、:+
ra brassicae) 2ギのべと病(Per
onospora destrutor) 、ホウレン
草のべと病(P eronospora 5pinac
iae)ダイズのべと病(P eronospora
manshuirca)、ソラマメのべと病(P er
onospora viciae)、ホップのべと病(
P 5eudopernospora husuli)
トマト、キュウリの灰色疫病(P 1iytophth
ora(、apsjci)、ジャガイモ、1−マド、ナ
スの疫病(P hytophthora、 1nfes
tans)、パイナツプルの疫病(P hytopht
hora cinnasoni)、タバコの疫病(P
hytophthora n1cotiana var
、 n1cotiana)、ビシューム属菌等による各
種作物の立枯病等が挙げられる。Plant diseases caused by algae and fungi for which the control agent of the present invention exhibits an excellent control effect include downy mildew of grapes (Plasmopar
e viLicota), downy mildew of cucurbits (P5
eudoperonospora cubensis)
, downy mildew of cruciferous vegetables (Peronosp, :+
ra brassicae) 2. Downy mildew (Per.
onospora destructor), downy mildew of spinach (Peronospora 5pinac)
iae) downy mildew of soybean (Peronospora
manshuirca), broad bean downy mildew (Per
onospora viciae), hop downy mildew (
P5eudopernospora husuli)
Gray late blight of tomatoes and cucumbers (P1iytophth)
ora (apsjci), potato, phytophthora, phytophthora, 1nfes
tans), pineapple blight (P hytopht)
hora cinnasoni), tobacco blight (P
hytophthora n1cotiana var
, n1cotiana), damping-off of various crops caused by bacteria of the genus Bysum, etc.
本発明化合物を藻菌類による植物病害防除剤の有効成分
として使用する場合、本発明化合物を1種又は2種以上
使用してもよい。When the compound of the present invention is used as an active ingredient of an agent for controlling plant diseases caused by algae and fungi, one or more compounds of the present invention may be used.
本発明化合物を藻菌類による植物病害防除剤として使用
する場合、使用目的に応してそのままか、または効果を
助長あるいは安定にするために農薬補助剤を混用して、
農薬製造分野において一般に行われている方法により、
わ)荊、細粒剤、粒荊、水和剤、フロアブル剤および乳
剤等の製造形態にして使用することができる。When the compound of the present invention is used as a control agent for plant diseases caused by algae and fungi, depending on the purpose of use, it may be used as is, or it may be mixed with an agrochemical adjuvant to enhance or stabilize the effect.
By the method commonly used in the agricultural chemical manufacturing field,
iii) It can be used in the form of manufacturing forms such as mulberry, fine granules, granules, wettable powders, flowable tablets, and emulsions.
これらの種々の製剤は実際の使用に際しては直接そのま
ま使用するか、または水で所望の濃度に希釈して使用す
ることができる。In actual use, these various formulations can be used directly or diluted with water to a desired concentration.
ここにいう農薬補助剤としては担体(希釈剤)およびそ
の他の補助剤たとえば展着剤、乳化剤、湿展剤、分散剤
、固着剤、崩壊剤等をあげることができる。Examples of the agrochemical auxiliary agent herein include carriers (diluents) and other auxiliary agents such as spreading agents, emulsifiers, wetting agents, dispersants, fixing agents, and disintegrants.
液体担体としてはトルエン、キシレン等の芳香族炭化水
素、メタノール、ブタノール、グリコール等のアルコー
ル類、アセトン等のケトン類、ジメチルホルムアミド等
のアミド類、ジメチルスルホキシド等のスルホキシド類
、メチルナフタレン、ンクロヘキサン、動植物油、脂肪
酸、脂肪酸エステル等があげられる。Liquid carriers include aromatic hydrocarbons such as toluene and xylene, alcohols such as methanol, butanol and glycol, ketones such as acetone, amides such as dimethylformamide, sulfoxides such as dimethyl sulfoxide, methylnaphthalene, nclohexane, animals and plants. Examples include oil, fatty acids, fatty acid esters, etc.
固体担体としてはクレー、カオリン、タルク、珪藻土、
ンリカ、炭酸カルシウム、モンモリロナイト、ヘントナ
イト、長石、石英、アルミナ、鋸屑等があげられる。Solid carriers include clay, kaolin, talc, diatomaceous earth,
Examples include calcium carbonate, montmorillonite, hentonite, feldspar, quartz, alumina, and sawdust.
また乳化剤または分散剤としては通常界面活性剤が使用
され、たとえば高級アルコール硫酸ナトリウム、ステア
リルトリメチルアンモニウムクロライド、ポリオキシエ
チレンアルキルフェニルエーテル、ラウリルベタイン等
の陰イオン系界面活性剤、陽イオン系界面活性剤、非イ
オン系界面活性剤、両性イオン系界面活性剤があげられ
る。In addition, surfactants are usually used as emulsifiers or dispersants, such as anionic surfactants such as higher alcohol sodium sulfate, stearyltrimethylammonium chloride, polyoxyethylene alkylphenyl ether, lauryl betaine, and cationic surfactants. , nonionic surfactants, and amphoteric surfactants.
展着剤としてはポリオキシエチレンノニルフェニルエー
テル、ポリオキンエチレンラウリルエーテル等が、湿展
剤としてはポリオキシエチレンノニルフェニルエーテル
、ジアルキルスルホサクシネート等が、固着剤としては
カルボキシメチルセルローズ、ポリビニルアルコール等
が、崩壊剤としてはりゲニンスルホン酸ナトリウム、ラ
ウリル硫酸ナトリウム等があげられる。Spreading agents include polyoxyethylene nonylphenyl ether, polyoxene ethylene lauryl ether, etc. Wetting agents include polyoxyethylene nonylphenyl ether, dialkyl sulfosuccinate, etc., and fixing agents include carboxymethyl cellulose, polyvinyl alcohol, etc. However, examples of disintegrants include sodium pyrogenin sulfonate and sodium lauryl sulfate.
いずれの製剤もそのまま単独で使用できるのみならず、
他の農園芸用殺菌剤、殺虫剤、植物生長調節側、殺ダニ
剤と混合して使用することもできる。Not only can each formulation be used alone, but
It can also be used in combination with other agricultural and horticultural fungicides, insecticides, plant growth regulators, and acaricides.
本発明藻2類によるM物病害防除剤における有効成分化
合物含量は、製剤形態、施用する方法、その他の条件に
よって種々異なり場合によっては有効成分化合物のみで
もよいが、通常は0.5〜95%(重り好ましくは2〜
70%(重量)の範囲である。The active ingredient compound content in the M disease control agent caused by algae type 2 of the present invention varies depending on the formulation form, application method, and other conditions. In some cases, only the active ingredient compound may be used, but it is usually 0.5 to 95%. (Weight preferably 2~
It is in the range of 70% (by weight).
本発明は殺菌剤は、を効成分濃度が好ましくは10〜4
000ppmで植物の茎葉に散布することができ、土壌
に散布する場合はを助成分散布量は0.02〜10 k
g / l Oa カ好マシイ。In the present invention, the disinfectant preferably has an active ingredient concentration of 10 to 4.
000ppm can be sprayed on the foliage of plants, and when spraying on soil, the dispersion amount is 0.02~10k
g/l Oa Strong.
本発明に係る藻菌類による植物病害防除剤は、べと病や
疫病に対して優れた予防効果、治療効果を有し、さらに
薬剤耐性菌の出現により防除効果が低下している場面に
おいても十分な防除効果が期待できる。The plant disease control agent using algae and fungi according to the present invention has excellent preventive and therapeutic effects against downy mildew and late blight, and is also sufficient even in situations where the control effect is reduced due to the appearance of drug-resistant bacteria. A great pest control effect can be expected.
このように本発明に係る藻菌類による植物病害防除11
f’l ;ま優れ1こ特性を具備しており有用である。In this way, plant disease control 11 caused by algae and fungi according to the present invention
f'l ; It has one excellent characteristic and is useful.
以下に2−クロロイソニコチン酸アミド誘導体の参考合
成例をあげて具体的に示す。A reference synthesis example of a 2-chloroisonicotinic acid amide derivative will be specifically described below.
参考合成例I
N−(1,1−ジメチル−2−プロピニル)2−クロロ
イソニコチン酸アミド(No、 7 )の合成:
1.1−ジメチルプロパルギルアミン1.39g(16
,7ミリモル)、トリエチルアミン1,67g(16,
5ミリモル)、エーテル30mの溶液に、0°Cに保ち
なから2−クロロイソニコチン酸クロライド2.64g
(15ミリモル)を滴下し、さらに室温で5時間撹拌し
た。反応終了後水にあけ、酢酸エチルで抽出した。Reference Synthesis Example I Synthesis of N-(1,1-dimethyl-2-propynyl)2-chloroisonicotinic acid amide (No. 7): 1.39 g (16
, 7 mmol), triethylamine 1,67 g (16,
5 mmol), 2.64 g of 2-chloroisonicotinic acid chloride in a solution of 30 ml of ether kept at 0°C.
(15 mmol) was added dropwise, and the mixture was further stirred at room temperature for 5 hours. After the reaction was completed, it was poured into water and extracted with ethyl acetate.
有機層を飽和食塩水で洗浄し、無水硫酸ナトリウムで乾
燥した後、溶媒を留去し、得られた粗生成物をンリカゲ
ルクロマトグラフィーにより精製して、N−(L、1−
ジメチル−2−プロピニル) 2− クロロイソニコ
チン酸アミド2、71. g (収率81.2%)を得
た。After washing the organic layer with saturated brine and drying over anhydrous sodium sulfate, the solvent was distilled off, and the resulting crude product was purified by phosphoric gel chromatography to obtain N-(L, 1-
dimethyl-2-propynyl) 2-chloroisonicotinic acid amide 2, 71. g (yield 81.2%) was obtained.
m、p、 98〜99℃
参考合成例2゜
N−(222−)リフルオロエチル)
2〜クロロイソニコチン酸アミド(No、 8 )の合
成:
222−iリフルオロエチルアミン1.78g(17,
97ミリモル)、トリエチルアミン1.67g(16,
5ミリモル)、酢酸エチル30iの溶液に、0゛Cに保
ちながら、2−クロロイソニコチン酸クロライド2.6
4g(15ミリモル)に滴下し、さらに室温で6時間攪
拌した。m, p, 98-99°C Reference synthesis example 2゜N-(222-)lifluoroethyl) Synthesis of 2-chloroisonicotinic acid amide (No. 8): 222-i Lifluoroethylamine 1.78 g (17,
97 mmol), triethylamine 1.67 g (16,
2.6 mmol) of 2-chloroisonicotinic acid chloride in a solution of 30 i.
4 g (15 mmol) was added dropwise, and the mixture was further stirred at room temperature for 6 hours.
反応液を水にあけ酢酸エチルで抽出し、有機層を飽和食
塩水で洗浄し硫酸ナトリウムで乾燥した。溶媒を留去し
た後、得られた残渣をノリ力ゲルクロマトグラフィーに
より精製して、N−(2,2,2−トリフルオロエチル
)−2−クロロインニコチン酸アミド3.03ε(収率
84.7%)を得た。The reaction solution was poured into water and extracted with ethyl acetate, and the organic layer was washed with saturated brine and dried over sodium sulfate. After distilling off the solvent, the resulting residue was purified by Nori gel chromatography to obtain N-(2,2,2-trifluoroethyl)-2-chloroinnicotinamide 3.03ε (yield 84 .7%).
m、p、 85.5 〜86.5 °C参考合
成例3゜
N−(2,6−ジメチルモルホリノメチル)2−クロロ
イソニコチン酸アミl’(Nct15)の合成コ
N−(ヒドロキシメチル)−2−クロロイソニコチン酸
アミド1.8g(9,65ミリモル)のクロロホルム(
30d)溶液に、室温で塩化チオニル0.9 d (1
2,5ミリモル)を滴下し、その後2.5時間加熱還流
した。冷却後、溶媒と過剰の塩化チオニルを減圧留去し
、N−(クロロメチル)−2−クロロイソニコチン酸ア
ミドを得た。m, p, 85.5 - 86.5 °C Reference synthesis example 3 ° Synthesis of N-(2,6-dimethylmorpholinomethyl)2-chloroisonicotinic acid amyl' (Nct15) N-(hydroxymethyl) -1.8 g (9.65 mmol) of 2-chloroisonicotinic acid amide in chloroform (
30d) Add 0.9 d (1
2.5 mmol) was added dropwise thereto, followed by heating under reflux for 2.5 hours. After cooling, the solvent and excess thionyl chloride were distilled off under reduced pressure to obtain N-(chloromethyl)-2-chloroisonicotinic acid amide.
続いて、2,6ジメチルモルホリン3.5g(30,4
ミリモル)のテトラヒドロフラン(60IIf)の溶液
に、i o ’c以下で、先に得たN(クロロメチル)
−2−クロロイソニコチン酸アミドを加え、さらに室温
で2時間攪拌した。Subsequently, 3.5 g of 2,6 dimethylmorpholine (30,4
Into a solution of tetrahydrofuran (60IIf) of
-2-chloroisonicotinic acid amide was added, and the mixture was further stirred at room temperature for 2 hours.
反応液を水にあけ酢酸エチルで抽出し、有機層を飽和食
塩水で洗浄し硫酸ナトリウムで乾燥した。溶媒を留去し
た後、得られた残渣をンリカゲルクロマトグラフィーに
より精製−で、N(2,ロー−ジメチルモルホリノメチ
ル)−2−クロロイソニコチン酸アミド]、9g(収率
69゜4%)を得た。The reaction solution was poured into water and extracted with ethyl acetate, and the organic layer was washed with saturated brine and dried over sodium sulfate. After distilling off the solvent, the resulting residue was purified by licage gel chromatography to obtain 9 g (yield: 69.4%) of N(2, rho-dimethylmorpholinomethyl)-2-chloroisonicotinic acid amide. I got it.
n’8 1.、5405
参考合成例4゜
N−(2,3−エポキシプロピル)−2−クロロイソニ
コチン酸アミF’(Nα16)の合成N−アリル−2−
クロロイソニコチン酸アミF2.8g(14,2ミリモ
ル)のクロロホルム(30d)溶液に、室温で80%過
安で、香酸3゜Ig(14,4ミリモル)を加え、さら
に室温で1時間、50〜60°Cで3時間撹拌した。冷
却後水にあけ酢酸エチルで抽出し、有機層を炭酸水素ナ
トリウム水溶液で洗浄し、無水g酸ナトリウムで乾燥し
た。溶媒を留去した後、得られた残渣をシリカゲルクロ
マ)・グラフィーにより精製して、N−(2,3−エポ
キシプロピル)2−クロロイソニコチン酸アミド1.O
g(収率33.0%)を得た。n'8 1. , 5405 Reference Synthesis Example 4 Synthesis of N-(2,3-epoxypropyl)-2-chloroisonicotinic acid amide F' (Nα16) N-allyl-2-
To a solution of 2.8 g (14.2 mmol) of amyl chlorisonicotinic acid F in chloroform (30d) was added 3° Ig (14.4 mmol) of folic acid at room temperature by 80%, and the mixture was further heated at room temperature for 1 hour. Stirred at 50-60°C for 3 hours. After cooling, it was poured into water and extracted with ethyl acetate, and the organic layer was washed with an aqueous sodium bicarbonate solution and dried over anhydrous sodium chloride. After evaporating the solvent, the resulting residue was purified by silica gel chromatography to obtain N-(2,3-epoxypropyl)2-chloroisonicotinic acid amide 1. O
g (yield 33.0%) was obtained.
m、p、 89〜9ドC
一般式(1)で表わされる2−クロロイソニコチン酸ア
ミド誘導体の代表例を物性値とともに第1表に示す。m, p, 89-9doC Representative examples of the 2-chloroisonicotinic acid amide derivative represented by the general formula (1) are shown in Table 1 along with their physical properties.
第1表
I
以下に製剤例を示すが、農薬補助剤の種類および混合比
率はこれらのみに限定されることなく、広い範囲で使用
可能である。なお「部」とあるのは重量部を意味する。Table 1 I Examples of formulations are shown below, but the types and mixing ratios of agricultural chemical adjuvants are not limited to these, and can be used in a wide range. Note that "parts" means parts by weight.
製剤例1. 粉 剤
化合物律8.2部およびクレー98部を混合粉砕し、粉
剤とする。Formulation example 1. Powder 8.2 parts of the compound and 98 parts of clay are mixed and ground to form a powder.
製剤例2. 水和剤
化合物量16.20部とカオリン75部と高級アルコー
ル硫酸ナトリウム3部およびリグニンスルホン酸ナトリ
ウム2部とを混合粉砕し水和剤とする。Formulation example 2. A wettable powder is prepared by mixing and pulverizing 16.20 parts of a wettable powder compound, 75 parts of kaolin, 3 parts of higher alcohol sodium sulfate, and 2 parts of sodium ligninsulfonate.
製剤例3. 粒 剤
微粉砕した化合物NQ7.8部、珪藻±36部ヘントナ
イム24部、タルク30部および崩壊剤2部を混合した
後、水18部を加え、均等に湿潤させ次に射出成形機を
通して押し出し、造粒し、製粒機で整粒した後、乾燥し
粉径0.6閣〜IIImの粒剤とする。Formulation example 3. After mixing 7.8 parts of the finely ground compound NQ, 24 parts of diatom ±36 parts of hentonaim, 30 parts of talc and 2 parts of disintegrant, 18 parts of water was added, the mixture was evenly moistened, and then extruded through an injection molding machine. After granulating and sizing using a granulator, the mixture is dried to form granules with a powder diameter of 0.6 to IIIm.
製剤例4. 微粒剤
化合物1&21.5部をメタノール5部に溶かし80〜
250メツンニの粒状クレー95部に混合滴下した後乾
燥し微粒剤とする。Formulation example 4. Dissolve 1 & 21.5 parts of the fine granule compound in 5 parts of methanol and
The mixture was mixed and dropped into 95 parts of granular clay of 250 ml and dried to form fine granules.
製剤例5. 乳 剤
化合物Na I 5.30部をキルシン52部ニ溶解し
、これにアルキルフェノールエチレンオキノド縮合物と
アルキルヘンゼンスルホン酸カルンウムの混合物(8:
2)18部を混合溶解して乳剤とする。Formulation example 5. 5.30 parts of the emulsion compound Na I was dissolved in 52 parts of Kirsin, and a mixture of an alkylphenol ethylene oxide condensate and a carunium alkylhenzenesulfonate (8:
2) Mix and dissolve 18 parts to make an emulsion.
末剤は水で薄めて、乳濁液として使用する。The powder is diluted with water and used as an emulsion.
次に本発明の効果に関する試験例を示す。Next, test examples regarding the effects of the present invention will be shown.
試験例1. ブドウベと病防除試験(予防効果)鉢植え
(径10c1m)ブドウの葉に製剤例2.5と同等に製
造した本発明の水和剤及び乳剤を所定濃度に希釈し噴霧
した。薬剤風乾後にべと病(P lasmopave
viticola)の水性胞子懸濁液を接種し20゛C
〜22″C,湿度100%の接種箱内に2日間、引き続
き温室内(20°C〜30’c )に7日間放置したの
ち発病程度を調査した。Test example 1. Grape Vine Disease Control Test (Preventive Effect) A hydrating powder and an emulsion of the present invention prepared in the same manner as in Formulation Example 2.5 were diluted to a predetermined concentration and sprayed onto the leaves of potted grapes (diameter: 10 cm). Mildew (Plasmopave) after air drying
Viticola) was inoculated with an aqueous spore suspension and incubated at 20°C.
The seeds were left in an inoculation box at ~22'C and 100% humidity for 2 days, and then placed in a greenhouse (20~30'C) for 7 days, and then the degree of disease onset was investigated.
結果は第2表に示した。The results are shown in Table 2.
第2表
注)*発病程度
0 : 病斑なし
1 : 病斑面積 5%以下
2 : 5〜20%
3: 〃 20〜50%
4 : 50%以上
**: 対照薬剤
TPN75%永和剤(テトラクロ
ルイソフタロニトリル)
商品NO:ダコニール永和剤
試験例2 ブドウベと病防除試験(治療効果)鉢植え(
径10cm)のブドウの葉にべと病(P lasmop
are viLicola)の水性胞7′懸命濁液を接
種し20°C〜22°C,湿度100%の接種箱内に2
日間放置後、製剤例2.5と同等に製造した本発明の水
和剤及び乳剤を所定濃度に希釈し噴霧した。さらに温室
内(20’C〜30 ’C)に7日間放置したのら発病
程度を調査した。Table 2 Note) *Incidence level 0: No lesions 1: Lesion area 5% or less 2: 5-20% 3: 20-50% 4: 50% or more **: Control drug TPN 75% permanent agent (Tetra Chlorisophthalonitrile) Product No.: Daconyl Permanent Agent Test Example 2 Grapevine disease control test (therapeutic effect) Potted plants (
Downy mildew (P lasmop) on grape leaves with a diameter of 10 cm
are inoculated with a 7' suspension of aqueous spores of A. viLicola) and placed in an inoculation box at 20°C to 22°C and 100% humidity.
After standing for a day, the wettable powder and emulsion of the present invention prepared in the same manner as Formulation Example 2.5 were diluted to a predetermined concentration and sprayed. Furthermore, after being left in a greenhouse (20'C to 30'C) for 7 days, the degree of disease onset was investigated.
結果は第3表に示した。The results are shown in Table 3.
第3表 注) 発病程度 発病なし 病斑面積 5%以下 病斑面積 5〜20% 20〜50 % 50%以上 対照薬剤 メタラキシル十マンセ゛ブ混合則 (商品名 リドミルMZ永和剤) (10%+55%)Table 3 note) Degree of onset No disease onset Lesion area 5% or less Lesion area: 5-20% 20-50% 50% or more control drug Metalaxyl 10-man section mixing rule (Product name Ridomil MZ permanent agent) (10%+55%)
Claims (1)
アルキル基、ハロゲン原子で置換されていてもよいアリ
ル基、C_3〜C_5アルキニル基、基−CH_2S(
O)_nR’、チオシアナトメチル基、アゾリルメチル
基、トリアゾリルメチル基、モリホリノメチル基、2,
6−ジメチルモルホリノメチル基、2,3−エポキシプ
ロピル基、ピリジルメチル基、2−クロロイソニコチニ
ルアミノメチル基または、ハロゲン原子で置換されてい
てもよいベンジル基を示し、ここでR’は低級アルキル
基を示し、nは0または1〜2の整数を示す。〕で表わ
される2−クロロイソニコチン酸アミド誘導体を有効成
分として含有することを特徴とする藻菌類による植物病
害防除剤。(1) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ [I] [In the formula, R is a lower alkyl group that may be substituted with a halogen atom, an allyl group that may be substituted with a halogen atom, C_3 ~C_5 alkynyl group, group -CH_2S(
O)_nR', thiocyanatomethyl group, azolylmethyl group, triazolylmethyl group, morpholinomethyl group, 2,
6-dimethylmorpholinomethyl group, 2,3-epoxypropyl group, pyridylmethyl group, 2-chloroisonicotinylaminomethyl group, or a benzyl group optionally substituted with a halogen atom, where R' is a lower It represents an alkyl group, and n represents 0 or an integer of 1-2. An agent for controlling plant diseases caused by algae and fungi, characterized by containing a 2-chloroisonicotinic acid amide derivative represented by the following as an active ingredient.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP24265490A JPH04124107A (en) | 1990-09-14 | 1990-09-14 | Control agent of phycomycete plant disease, containing 2-chloronicotinic acid amide derivative as active ingredient |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP24265490A JPH04124107A (en) | 1990-09-14 | 1990-09-14 | Control agent of phycomycete plant disease, containing 2-chloronicotinic acid amide derivative as active ingredient |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH04124107A true JPH04124107A (en) | 1992-04-24 |
Family
ID=17092263
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP24265490A Pending JPH04124107A (en) | 1990-09-14 | 1990-09-14 | Control agent of phycomycete plant disease, containing 2-chloronicotinic acid amide derivative as active ingredient |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH04124107A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2002022583A3 (en) * | 2000-09-18 | 2002-07-18 | Du Pont | Pyridinyl amides and imides for use as fungicides |
-
1990
- 1990-09-14 JP JP24265490A patent/JPH04124107A/en active Pending
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2002022583A3 (en) * | 2000-09-18 | 2002-07-18 | Du Pont | Pyridinyl amides and imides for use as fungicides |
US7074742B2 (en) | 2000-09-18 | 2006-07-11 | E. I. Du Pont De Nemours And Company | Pyridinyl amides and imides for use as fungicides |
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