JPS63267754A - Benzamide derivative and soil disease-controlling agent - Google Patents
Benzamide derivative and soil disease-controlling agentInfo
- Publication number
- JPS63267754A JPS63267754A JP10204787A JP10204787A JPS63267754A JP S63267754 A JPS63267754 A JP S63267754A JP 10204787 A JP10204787 A JP 10204787A JP 10204787 A JP10204787 A JP 10204787A JP S63267754 A JPS63267754 A JP S63267754A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- present
- soil
- soil disease
- formula
- 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
- 239000002689 soil Substances 0.000 title claims abstract description 33
- 201000010099 disease Diseases 0.000 title claims abstract description 31
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims abstract description 31
- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 22
- 150000003936 benzamides Chemical class 0.000 title claims description 9
- 239000004480 active ingredient Substances 0.000 claims description 15
- 239000000126 substance Substances 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 238000006467 substitution reaction Methods 0.000 claims description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical group NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 abstract description 64
- 230000000694 effects Effects 0.000 abstract description 10
- -1 benzoic acid halide Chemical class 0.000 abstract description 8
- 239000002904 solvent Substances 0.000 abstract description 8
- 231100000674 Phytotoxicity Toxicity 0.000 abstract description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract description 6
- 125000005843 halogen group Chemical group 0.000 abstract description 5
- 238000009835 boiling Methods 0.000 abstract description 3
- 238000002360 preparation method Methods 0.000 abstract description 3
- 239000005711 Benzoic acid Substances 0.000 abstract description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract description 2
- 235000010233 benzoic acid Nutrition 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 241000219193 Brassicaceae Species 0.000 abstract 1
- 241001503464 Plasmodiophora Species 0.000 abstract 1
- 238000007033 dehydrochlorination reaction Methods 0.000 abstract 1
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 230000000052 comparative effect Effects 0.000 description 16
- 239000000843 powder Substances 0.000 description 16
- 239000000203 mixture Substances 0.000 description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000839 emulsion Substances 0.000 description 9
- 235000010149 Brassica rapa subsp chinensis Nutrition 0.000 description 8
- 235000000536 Brassica rapa subsp pekinensis Nutrition 0.000 description 8
- 241000499436 Brassica rapa subsp. pekinensis Species 0.000 description 8
- 241000196324 Embryophyta Species 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000004927 clay Substances 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- LKPLKUMXSAEKID-UHFFFAOYSA-N pentachloronitrobenzene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl LKPLKUMXSAEKID-UHFFFAOYSA-N 0.000 description 5
- 239000000454 talc Substances 0.000 description 5
- 229910052623 talc Inorganic materials 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 239000005909 Kieselgur Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 description 3
- 229910052570 clay Inorganic materials 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 230000012010 growth Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000004563 wettable powder Substances 0.000 description 3
- 229940126062 Compound A Drugs 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 206010039509 Scab Diseases 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 244000061456 Solanum tuberosum Species 0.000 description 2
- 235000002595 Solanum tuberosum Nutrition 0.000 description 2
- 239000003945 anionic surfactant Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 239000012752 auxiliary agent Substances 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 2
- 230000000887 hydrating effect Effects 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 238000011081 inoculation Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 230000002786 root growth Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 244000020190 Azalea indica Species 0.000 description 1
- 235000002498 Azalea indica Nutrition 0.000 description 1
- 241001429251 Beet necrotic yellow vein virus Species 0.000 description 1
- 235000021537 Beetroot Nutrition 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- 235000011293 Brassica napus Nutrition 0.000 description 1
- 240000007124 Brassica oleracea Species 0.000 description 1
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
- 240000008100 Brassica rapa Species 0.000 description 1
- 235000000540 Brassica rapa subsp rapa Nutrition 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 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 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 241000132152 Polymyxa Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 241000187181 Streptomyces scabiei Species 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 238000012271 agricultural production Methods 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 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 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000008297 liquid dosage form Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000009335 monocropping Methods 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 244000045561 useful plants Species 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、新規なベンズアミド誘導体もしくはそれらの
塩類ならびに該誘導体もしくはそれらの塩類を有効成分
として含有することを特徴とする土壌病害防除剤に関す
るものである。Detailed Description of the Invention [Field of Industrial Application] The present invention relates to a novel benzamide derivative or a salt thereof, and a soil disease control agent characterized by containing the derivative or a salt thereof as an active ingredient. It is.
上記の本発明化合物は、文献未記載の新規化合物であり
、土壌病害、例えば十字花科植物に発生する根こぶ病に
対して卓効を示すと共に、有用作物に対して全（薬害の
ない優れたものである。The above-mentioned compound of the present invention is a new compound that has not been described in any literature, and is highly effective against soil diseases such as clubroot disease that occurs in cruciferous plants, and is also highly effective against useful crops (without phytotoxicity). It is something that
農業生産上重要な問題の一つとして連作障害が挙げられ
るが、その原因の大部分は土壌病害に起因している。従
来土壌病害の防除はその発生生態から極めて困難であり
優れた防除薬剤の開発が望まれている０例えば重要な土
壌病害の一つである十字花科植物に発生する根こぶ病は
近年その発生が増大しハクサイ、キャベツ、カブなどの
生産に大きな被害を与えている。Continuous cropping failure is one of the important problems in agricultural production, and most of the causes are caused by soil diseases. Control of conventional soil diseases is extremely difficult due to the ecology of their occurrence, and the development of superior control agents is desired. has increased, causing great damage to the production of Chinese cabbage, cabbage, turnips, etc.
又、ビートのそう根病は、ポリミキサ・ビターエなる土
壌生息菌が、ビート・ネクロティック・イエロー・ベイ
ン・ウィルスを媒介して引き起こされるが、現在その発
生地域が拡大し、被害は大きくなっている。ジャガイモ
そうか病もジャガイモ生産に大きな被害を与えている。Furthermore, beet root disease is caused by a soil-dwelling fungus called Polymyxa bitterae, which is transmitted by the beet necrotic yellow vein virus, and the area where it occurs is currently expanding and the damage is increasing. . Potato scab also causes great damage to potato production.
しかるに現在、土壌病害に対して薬剤防除が種々行われ
ているが、十分な防除効果は得られていない。However, although various chemical control methods are currently being used to control soil diseases, sufficient control effects have not been obtained.
特に十字花科植物に発生する根こぶ病に対して薬剤防除
が種々行われているが現在の市販薬剤（この有効成分は
例えばペンタクロルニトロベンゼン等である。）では良
好なる結果が得られない状況にある。即ちその市販薬剤
を多量に施用しないと十分な防除効果かえられないもの
であり、一方それを多量施用すると、安全性や環境汚染
に対して問題もありうる０本発明化合物は新規化合物で
あるが、これが土壌病害、特に十字花科植物に発生する
根こぶ病に対して卓効を示すことを見出し本発明を完成
した。In particular, various chemical control methods have been used to control the clubroot disease that occurs in cruciferous plants, but current commercially available drugs (the active ingredient of which is pentachlornitrobenzene, for example) are unable to produce good results. It is in. In other words, a sufficient control effect cannot be achieved unless the commercially available drug is applied in large amounts.On the other hand, if it is applied in large amounts, there may be problems with safety and environmental pollution.Although the compound of the present invention is a new compound, We have completed the present invention by discovering that this is highly effective against soil diseases, particularly clubroot disease that occurs in cruciferous plants.
なお、公知文献として特開ｄｓｓｏ−１５２４０１号公
報および特開昭６２−１６４６５号公報が知られている
。Incidentally, as well-known documents, JP-A dsso-152401 and JP-A 62-16465 are known.
特開昭６０−１５２４０１号公報には、特定のベンズア
ミド誘導体が開示され、これらが農園芸用病害防除剤と
して有用で特にイネいもち病に卓越した防除効果を示す
ことが記載されている。しかし新規な本発明化合物は、
具体的に全（開示されておらず、また土壌病害の防除に
ついても全く開示されていない、一方、特開昭６２−１
６４６５号公報にも特定のベンズアミド誘導体が開示さ
れ、これらが土壌病害の防除について効果を有すること
が開示されている。しかし本発明化合物については、具
体的に全く開示されていない。JP-A-60-152401 discloses certain benzamide derivatives, and describes that these are useful as disease control agents for agricultural and horticultural use, and particularly exhibit outstanding control effects on rice blast. However, the novel compound of the present invention
Specifically, all (not disclosed), and control of soil diseases is not disclosed at all.
No. 6465 also discloses specific benzamide derivatives and discloses that these are effective in controlling soil diseases. However, the compound of the present invention is not specifically disclosed at all.
本発明は、一般式（Ｉ）：
（式中、Ｘはハロゲン原子を、ｎは１または２の整数を
示す。）で表されるベンズアミド誘導体もしくはそれら
の塩類ならびにこれらの少なくとも１種を有効成分とし
て含有することを特徴とする土壌病害防除剤に関するも
のである。The present invention provides benzamide derivatives represented by general formula (I): (wherein, X represents a halogen atom, and n represents an integer of 1 or 2) or salts thereof, and at least one thereof as an active ingredient This invention relates to a soil disease control agent characterized by containing:
上記一般式（１）で表される本発明化合物において、Ｘ
としては例えば塩素原子、臭素原子、ヨウ素原子、弗素
原子が挙げられるが、塩素原子が好ましい、ｎとしては
、２が好ましい、また、Ｘの置換位置としては、２位お
よび４位が望ましい。In the compound of the present invention represented by the above general formula (1),
For example, a chlorine atom, a bromine atom, an iodine atom, and a fluorine atom can be mentioned, but a chlorine atom is preferable, n is preferably 2, and the substitution positions of X are preferably the 2-position and the 4-position.
また、これらの塩類としてはナトリウム、カリウムなど
のアルカリ金属塩、カルシウム、マグネシウムなどのア
ルカリ土類金属塩、各種のアミン塩および各種の第４ア
ンモニウム塩などが挙げられる。Examples of these salts include alkali metal salts such as sodium and potassium, alkaline earth metal salts such as calcium and magnesium, various amine salts, and various quaternary ammonium salts.
本発明化合物は、公知文献には具体的に全く開示されて
いない新規化合物であり、土壌病害に対して卓越した防
除効果を有し、有用植物には全く薬害がないものであり
実用的に優れた土壌病害防除剤である。The compound of the present invention is a new compound that has not been specifically disclosed in any known literature, and has excellent control effects against soil diseases and has no phytotoxicity on useful plants, making it excellent for practical use. It is a soil disease control agent.
本発明化合物は、前記の公知文献に具体的に記載されて
いる化合物に比べて、土壌病害防除効果が約１０倍以上
優れており、例えば本発明化合物の場合は０．２Ｋｇ／
ｈａの処理量においても十分防除効果を有するものがあ
るが、公知化合物の場合には、２ Ｋｇ／ｈａの処理量
においても多少の防除効果を有するものもあるが全く効
果のないものもある。The compound of the present invention is approximately 10 times more effective in controlling soil diseases than the compounds specifically described in the above-mentioned known literature; for example, the compound of the present invention has a soil disease control effect of 0.2 kg/
Some compounds have a sufficient control effect even at a treatment amount of 2 kg/ha, but some known compounds have some control effect even at a treatment amount of 2 kg/ha, but some have no effect at all.
一方、薬害は、本発明化合物の場合は１０Ｋｇ／ｈａの
処理量においてもほとんど認められないが、公知化合物
の場合にはｌ Ｋｇ／ｈａの処理量においても薬害が認
められるものがある。On the other hand, in the case of the compounds of the present invention, almost no phytotoxicity is observed even at a treatment rate of 10 Kg/ha, but in the case of known compounds, phytotoxicity is observed even at a treatment rate of 1 Kg/ha.
すなわち、本発明化合物は、公知化合物に比べて土壌病
害防除効果の面でも、薬害の面でも極めて優れたもので
あり、このことは後記の試験例において具体的に記載し
た。That is, the compounds of the present invention are extremely superior to known compounds both in terms of soil disease control effect and in terms of phytotoxicity, and this is specifically described in the test examples below.
（以下、余白）
本発明化合物は、以下に示す方法により容易に合成でき
る。(Hereinafter, blank spaces) The compound of the present invention can be easily synthesized by the method shown below.
（ＩＩ） ＣＨ（ＣＨｊ）ｚ（上
記式中、ＸおよびＹはハロゲン原子を、ｎは１または２
の整数を示す、）
すなわち、ハロゲン置換安息香酸ハロゲン化物（ｎ）と
２．４．６− ）リイソブロピルベンゼンスルホンアミ
ドを縮合させて本発明化合物（Ｉ）を得ることができる
。この反応は脱塩化水素剤の存在下で行うのが好ましく
、脱塩化水素剤としては例えば水酸化ナトリウム、水酸
化カリウムなどの水酸化物、炭酸水素ナトリウム、炭酸
ナトリウム、炭酸カリウムなどの炭酸化物、トリエチル
アミン、ピリジン等のアミン類などが挙げられる。縮合
反応は反応に不活性な溶媒中で行うのが好ましい。(II) CH(CHj)z (in the above formula, X and Y are halogen atoms, n is 1 or 2
In other words, the compound (I) of the present invention can be obtained by condensing a halogen-substituted benzoic acid halide (n) and 2.4.6-)lyisopropylbenzenesulfonamide. This reaction is preferably carried out in the presence of a dehydrochlorinating agent, such as hydroxides such as sodium hydroxide and potassium hydroxide, carbonates such as sodium bicarbonate, sodium carbonate, and potassium carbonate; Examples include amines such as triethylamine and pyridine. The condensation reaction is preferably carried out in a solvent inert to the reaction.
不透性溶媒としては、例えばベンゼン、トルエン、キシ
レンなどの芳香族炭化水素系溶媒、ジエチルエーテル、
テトラヒドロフラン、ジオキサンなどのエーテル系溶媒
、アセトン、メチルエチルケトンなどのケトン系溶媒な
どが挙げられ、これらを単一で、あるいはこれらを混合
して用いることができる。Examples of impermeable solvents include aromatic hydrocarbon solvents such as benzene, toluene, and xylene, diethyl ether,
Examples include ether solvents such as tetrahydrofuran and dioxane, ketone solvents such as acetone and methyl ethyl ketone, and these can be used alone or in combination.
反応温度は室温から用いる溶媒の沸点の間で可能である
が、溶媒の沸点に設定することが掻作上もっとも有利で
ある。通常当業者であれば、適当な反応条件を容易に設
定できる。Although the reaction temperature can be set between room temperature and the boiling point of the solvent used, it is most advantageous for scraping to be set at the boiling point of the solvent. Those skilled in the art can easily set appropriate reaction conditions.
以下に本発明化合物を得る方法を実施例によってさらに
具体的に示すが、本発明はこれらの実施例のみに限定さ
れるものではない。The method for obtaining the compound of the present invention will be shown below in more detail through Examples, but the present invention is not limited to these Examples.
（以下、余白）
スＪＬＬＬ Ｎ−（２，４，６−）リイソプロビルベ
ンゼンスルホニル）−２，６−ジクロロベンズアミドの
合成（化合物Ｎａ９ ）
２００ｍｌの４プロフラスコに、８．５０ｇ（０，０３
０モル）の２．４．６− ）リイソプロピルベンゼンス
ルホンアミド、５．４０ｇ（０，０３９モル）の炭酸カ
リウムおよび７０−１のジオキサンを入れた。この溶液
中に室温で、２゜６−ジクロロベンゾイルクロライド６
．２８ｇ（０，０３０モル）の３０−１ジオキサン溶液
を撹拌しながら滴下した０滴下終了後、反応液を加熱し
て、ジオキサン還流下で５時間加熱撹拌した。放冷後、
不溶物を濾別し、３抛ｌのジオキサンで洗浄した。濾液
と洗液を合わせ、減圧濃縮し、残渣に氷水２００ｓ＋１
を加え、塩酸で酸性とした０分離した油状物を酢酸エチ
ル２００ｍ１で抽出した後、無水硫酸マグネシウムで乾
燥し、減圧で濃縮した。得られた残渣をトルエン：エタ
ノール−１：１の混合溶媒で再結晶し濾取、乾燥して目
的とするＮ−（２，４，６−トリイソプロピルベンゼン
スルホニル）−２，６−シクロロベンズアミド１０．２
７ｇを得た。(Hereinafter, blank space) Synthesis of N-(2,4,6-)liisopropylbenzenesulfonyl)-2,6-dichlorobenzamide (compound Na9) 8.50 g (0,03
0 mol) of 2.4.6-) lyisopropylbenzenesulfonamide, 5.40 g (0.039 mol) of potassium carbonate and 70-1 of dioxane. 2゜6-dichlorobenzoyl chloride 6 was added to this solution at room temperature.
．． 28 g (0,030 mol) of a 30-1 dioxane solution was added dropwise with stirring. After the completion of the dropwise addition, the reaction solution was heated and stirred under dioxane reflux for 5 hours. After cooling,
Insoluble matter was filtered off and washed with 3 liters of dioxane. Combine the filtrate and washing liquid, concentrate under reduced pressure, and add 200 s of ice water to the residue.
was added, acidified with hydrochloric acid, and the separated oil was extracted with 200 ml of ethyl acetate, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue is recrystallized from a 1:1 mixed solvent of toluene:ethanol, collected by filtration, and dried to obtain the desired N-(2,4,6-triisopropylbenzenesulfonyl)-2,6-cyclobenzamide. 10.2
7g was obtained.
（枚重７５．０％、 融点２１７〜２２０℃）元素分析
値 ０％ ８％ Ｎ％計算値 ５７，８９
５，９６ ３．０７実測値 ５７，７０ ６，
００ ３．１１ｍ Ｎ−（２，４，６−トリイソプ
ロピルベンゼンスルホニル）−２，４−ジクロロベンズ
アミドの合成（化合物ＮｃＬ８ ’）
２００ｍｌの４プロフラスコを使用し、実施例１と同様
の仕込みモル比で、溶媒をアセトンに変更し、アセトン
還流下で８時間加熱撹拌した。放冷後、実施例１と同様
に処理を行って、目的とするＮ−（２，４，６−トリイ
ソプロピルベンゼンスルホニル）−２，４−ジクロロベ
ンズアミド９．５１ｇを得た。(Sheet weight 75.0%, melting point 217-220℃) Elemental analysis value 0% 8% N% calculated value 57,89
5,96 3.07 Actual value 57,70 6,
00 3.11m Synthesis of N-(2,4,6-triisopropylbenzenesulfonyl)-2,4-dichlorobenzamide (compound NcL8') Using a 200 ml 4-pro flask, the charging molar ratio was the same as in Example 1. Then, the solvent was changed to acetone, and the mixture was heated and stirred for 8 hours under reflux of acetone. After cooling, the same treatment as in Example 1 was performed to obtain 9.51 g of target N-(2,4,6-triisopropylbenzenesulfonyl)-2,4-dichlorobenzamide.
（枚重６９．５％、 融点１８８〜１９１℃）元素分析
値 ０％ ８％ Ｎ％計算値 ５７，８９
５，９６ ３．０７実測値 ５７．７４ ６．
０２ ３．０４Ｍ Ｎ−（２，４，６−）リイソブ
ロビルベンゼンスルホニル）−４−クロロベンズアミド
の合成（化合物阻３）
１００ｍｌの４プロフラスコに、２．８３ｇ（０，０１
０モル）の２．４．６− ）リイソブロピルベンゼンス
ルホンアミド、０．９５ｇ（０，０１２モル）のピリジ
ンおよび３０ａ＋１のテトラヒドロフランを入れた。こ
の溶液中に室温で、４−クロロベンゾイルクロライド１
．７５ｇ（０，０１０モル）のｌＯ■ｌテトラヒドロフ
ラン溶液を撹拌しながら滴下した０滴下終了後、反応液
を加熱して、テトラヒドロフラン還流下で４時間加熱撹
拌した。(Sheet weight 69.5%, melting point 188-191℃) Elemental analysis value 0% 8% N% calculated value 57,89
5,96 3.07 Actual value 57.74 6.
02 3.04M Synthesis of N-(2,4,6-)lyisobrobylbenzenesulfonyl)-4-chlorobenzamide (compound inhibition 3) 2.83 g (0,01
0 mol) of 2.4.6-) lyisopropylbenzenesulfonamide, 0.95 g (0.012 mol) of pyridine and 30a+1 of tetrahydrofuran. In this solution at room temperature, 4-chlorobenzoyl chloride 1
．． 75 g (0,010 mol) of a 1O2 tetrahydrofuran solution was added dropwise with stirring. After the completion of the dropwise addition, the reaction solution was heated and stirred for 4 hours under refluxing tetrahydrofuran.
放冷後、希塩酸水２００＠ｌに注ぎ、分離した油状物を
酢酸エチル２００ｍ１で抽出した後、実施例１と同様に
処理を行って、目的とするＮ−（２，４，６−トリイソ
プロピルベンゼンスルホニル）−４−クロロベンズアミ
ド２．０５ｇを得た。After cooling, it was poured into 200 ml of diluted hydrochloric acid, and the separated oil was extracted with 200 ml of ethyl acetate. 2.05 g of benzenesulfonyl)-4-chlorobenzamide was obtained.
（枚重４８．５％、 融点２１８〜２２１”Ｃ）元素分
析値 ０％ ８％ Ｎ％計算値 ６２．６２
６，６９ ３．３２実測値 ６２，４８ ６
，７５ ３．４０次に本発明に含まれる化合物の例を
、前記実施例で合成した化合物と共に以下の第１表に示
す。(Sheet weight 48.5%, melting point 218-221"C) Elemental analysis value 0% 8% N% calculated value 62.62
6,69 3.32 Actual value 62,48 6
, 75 3.40 Next, examples of compounds included in the present invention are shown in Table 1 below along with the compounds synthesized in the above examples.
しかし本発明化合物は、これらのみに限定されるもので
はない。However, the compounds of the present invention are not limited to these.
第１表
Ｃ０（ＣＨｓ）ｚ
で表される化合物
化合物Ｎｏ、 Ｘｎ 融点（’Ｃ）１
２−Ｃ１１９４〜１９７２ ３
−ＣＩ １８５〜１８７３ ４−Ｃ
Ｉ ２１８〜２２１４ ３、４−Ｃ
１ｇ ２０２〜２０４５ ３．５−Ｃ
１２１７５〜１９０６ ２．５−ｔ、ｔｚ
１Ｂ３〜１８９第３〜（続き）
化合物Ｎｏ、 ｌ、 融点（”Ｃ）７
２．３−Ｃ１２１５９〜１７１８
２＋４−ｃｔｚ １８８〜１９１９
２、６−Ｃ１２２１７〜２２０１０ ２
．６−Ｐ！ １９０〜１９３１１ ２
−Ｂｒ １４１〜１４３１２ ３−
Ｂｒ １８８〜１９０１３ ４−Ｂ
ｒ ２０９〜２１１１４ ３−Ｉ
１９５〜１９８１５ ４−１
２１０〜２１２１６ ２．５−Ｂｒ。Table 1 Compounds represented by C0(CHs)z Compound No. Xn Melting point ('C)1
2-C1194~1972 3
-CI 185-1873 4-C
I 218-2214 3, 4-C
1g 202-2045 3.5-C
12175-1906 2.5-t, tz
1B3-189 No. 3-(Continued) Compound No. 1, Melting point ("C) 7
2.3-C12159-1718
2+4-ctz 188-1919
2,6-C12217-22010 2
．． 6-P! 190-19311 2
-Br 141-14312 3-
Br 188-19013 4-B
r 209-21114 3-I
195-19815 4-1
210-21216 2.5-Br.
１７ ２．４−Ｂｒｘ
（以下、余白）
本発明化合物を土壌病害防除剤として施用するにあたっ
ては一般には適当な担体、例えばクレー、タルク、ベン
トナイト、珪藻土、炭酸カルシウム等の固体担体あるい
は水、アルコール（メタノール、エタノール等）、芳香
族炭化水素類（ベンゼン、トルエン、キシレン等）、塩
素化炭化水素類、エーテル類、ケトン類、エステル類（
酢酸エチル等）、酸アミド類 （ジメチルホルムアミド
等）などの液体担体と混用して適用することができ、所
望により乳化剤、分散剤、懸濁剤、浸透剤、展着剤、安
定剤、補助剤などを添加し、液剤、乳剤、水和剤、粉剤
、粒剤等任意の剤型にて実用に供することができる。17 2.4-Brx (Hereinafter, blank) When applying the compound of the present invention as a soil disease control agent, generally a suitable carrier such as a solid carrier such as clay, talc, bentonite, diatomaceous earth, calcium carbonate, or water, alcohol ( methanol, ethanol, etc.), aromatic hydrocarbons (benzene, toluene, xylene, etc.), chlorinated hydrocarbons, ethers, ketones, esters (
(ethyl acetate, etc.), acid amides (dimethylformamide, etc.), and can be used in combination with liquid carriers such as emulsifiers, dispersants, suspending agents, penetrating agents, spreading agents, stabilizers, and adjuvants, if desired. It can be put to practical use in any desired dosage form, such as a liquid, emulsion, wettable powder, powder, or granule.
固体形態の剤型（粉剤、粒剤、水和剤等）の場合は本発
明化合物の含有割合としては、特に限定されるものでは
ないが、０．１〜６０重量％ぐらいが望ましく、更に、
０．５〜３０重量％ぐらいが好ましい。In the case of solid dosage forms (powders, granules, wettable powders, etc.), the content of the compound of the present invention is not particularly limited, but is preferably about 0.1 to 60% by weight, and further,
It is preferably about 0.5 to 30% by weight.
一方、液体形態の剤型（乳剤、液剤）の場合は本発明化
合物の含有割合としては、特に限定されるものではない
が、０．５〜９０重量％ぐらいが望ましく、更に、２〜
８０！量％ぐらいが好ましい、本発明の製剤を土壌へ処
理する方法として、一つは、粉剤、粒剤の場合は、直接
土壌に処理し、土壌と混合するのが好ましい０本発明化
合物の処理量としては特に限定されるものではないが、
１ヘクタール当たり０．０１〜２００ｋｇぐらいが望ま
しく、更に０．１〜１００ｋｇぐらいが好ましい。On the other hand, in the case of liquid dosage forms (emulsions, solutions), the content of the compound of the present invention is not particularly limited, but is preferably about 0.5 to 90% by weight, and more preferably 2 to 90% by weight.
80! One of the methods for treating the soil with the preparation of the present invention, which is preferably about %, is to directly treat the soil and mix with the soil in the case of powders and granules. Although not particularly limited,
The amount per hectare is preferably about 0.01 to 200 kg, more preferably about 0.1 to 100 kg.
他の方法は、乳剤、液剤、水和剤の場合で、これらの剤
を水で希釈して、本発明化合物の所定濃度に調整した後
に、土壌中へ潅注処理する方法である。この場合、本発
明化合物の濃度としては、特に限定されるものではない
が、１〜２０００ｐｐｍ＋が望ましく、更に、５０〜１
１０００ｐｐ ぐらいが好ましい、また本発明化合物
の処理量としては特に限定されるものではないが、１ヘ
クタール当たり０．０１〜２００ｋｇぐらいが望ましく
、更に０．１−１００ｋｇぐらいが好ましい。Another method is to dilute emulsions, solutions, and wettable powders with water to adjust the concentration of the compound of the present invention to a predetermined concentration, and then irrigate them into the soil. In this case, the concentration of the compound of the present invention is not particularly limited, but is preferably 1 to 2000 ppm+, more preferably 50 to 1 ppm+.
The amount of the compound of the present invention to be treated is preferably about 1000 pp, and is not particularly limited, but is preferably about 0.01 to 200 kg per hectare, more preferably about 0.1 to 100 kg.
本発明の製剤の中で、特に粉剤が好ましく、二の粉剤の
固体担体としては、特に限定されるものではないが、ク
レー、タルク、炭酸カルシウム、珪藻土が好ましく、こ
れらの１種または２種以上を使用できる。また、補助剤
としてホワイトカーボンを必要に応じて添加してもよい
、好ましい配合割合としては、本発明化合物を１〜２０
重量部、クレー、タルク、炭酸カルシウムもしくは珪藻
土を６０〜９９重量部、ホワイトカーボン（補助剤）を
０〜２０重量部の範囲で任意に配合しうる。Among the preparations of the present invention, powders are particularly preferred, and solid carriers for the second powder are not particularly limited, but clay, talc, calcium carbonate, and diatomaceous earth are preferred, and one or more of these are preferred. can be used. In addition, white carbon may be added as an auxiliary agent if necessary.The preferred blending ratio is 1 to 20% of the compound of the present invention.
60 to 99 parts by weight of clay, talc, calcium carbonate or diatomaceous earth, and 0 to 20 parts by weight of white carbon (auxiliary agent) may be optionally blended.
本発明に於いて防除できる土壌病害は、特に限定される
ものではないが、例えば十字花科植物根こぶ病、ビート
のそう根病、ジャガイモそうか病等が挙げられる。The soil diseases that can be controlled in the present invention are not particularly limited, and include, for example, clubroot of cruciferous plants, scab of beets, scab of potatoes, and the like.
次に本発明化合物を有効成分とする土壌病害防除剤の製
剤例を示すが、本発明の土壌病害防除剤はこれらのみに
限定されるものではない、なお、以下の製剤例において
「部」は重量部を意味する。Next, examples of formulations of soil disease control agents containing the compounds of the present invention as active ingredients are shown, but the soil disease control agents of the present invention are not limited to these. In the following formulation examples, "part" is Means parts by weight.
事Ｕ汁例」２ 水和剤
本発明化合物 −・−・−・・−−−−−−２５
部ジークライトＡ −−−−−−−−−−−−−−−
−−−−−−−−−６９部（カオリン系クレー：ジーク
ライト工業■商品名）ツルポール５０３９ ・−・−−
−−−一−〜・−・ ３部（非イオン性界面活性剤とア
ニオン性界面活性剤との混合物：東邦化学■商品名）
カープレックス（固結防止剤）・−−−−−３部（ホワ
イトカーボン：塩野義製薬■商品名）以上を均一に混合
粉砕して水和剤とする。使用に際しては上記水和剤を２
５０〜２５．０００倍に希釈して使用する。Example of Juice” 2 Wettable powder Compound of the present invention −・−・−・・−−−−−25
Part Sieglite A ----------------
−−−−−−−−−69 parts (Kaolin clay: Sieglite Kogyo ■Product name) Tsurupol 5039 ・−・−−
---1---3 parts (Mixture of nonionic surfactant and anionic surfactant: Toho Chemical ■Product name) Carplex (anti-caking agent) ---3 parts (White Carbon: Shionogi & Co., Ltd. trade name) The above is mixed and pulverized uniformly to make a wettable powder. When using, add 2 of the above hydrating agents.
Use after diluting 50 to 25,000 times.
ＩＩシ匹ｌ−乳剤
本発明化合物 −一一−−−−−−−−−−−・
−・ ５０部キ シ し ン −−−−
・−−−−−−−−−−−−２５部ジメチルホルムアミ
ド ・−−−−−−−−−−＝ ２０部ツルポール２
６８０ −・−ｍ−−−−・・−・ ５部（非イオン
性界面活性剤とアニオン性界面活性剤との混合物：東邦
化学■商品名）
以上を均一に混合して乳剤とする。使用に際しては上記
乳剤を５００〜５０．０００倍に希釈して使用する。II emulsion Compound of the present invention -11--------
---50 copies ---
・−−−−−−−−−−−−25 parts dimethylformamide ・−−−−−−−−−−= 20 parts Tsurpol 2
680 -·-m---·································· 5 parts (Mixture of nonionic surfactant and anionic surfactant: Toho Chemical ■ trade name) The above is mixed uniformly to form an emulsion. When used, the above emulsion is diluted 500 to 50,000 times.
事」１例」−粉剤
本発明化合物 −−−ｍ−・−・−・−・−５部
クレー ・−・−−一−−−−−−−−−
・９５部以上を均一に混和し、有効成分５％の粉剤を得
る。Example 1 - Powder Compound of the present invention ---m-・------5 parts Clay ・----1------
・Mix 95 parts or more evenly to obtain a powder containing 5% of the active ingredient.
ｌ五鍔土 粉剤
本発明化合物 ・−−−一−・−・−・・−・
１部タルク、 ・−−−−−−−−−−−−
−−＝ ９９部以上を均一に混和し、有効成分１％の
粉剤を得る。1 Gotsudo Powder Compound of the present invention ・----1-・-・-・・-・
1 part talc, ・−−−−−−−−−−−−
--= 99 parts or more are mixed uniformly to obtain a powder containing 1% of the active ingredient.
里月■工 粉剤
本発明化合物 ・−−−−−−−−−−−−−−
−２０部クレー ・−・−−−−−−・・
−・７０部ホワイトカーボン ・−−−−一−−・・
−・・・ １０部以上を均一に混和し、有効成分２０％
の粉剤を得る。Satsuki ■ Powder Compound of the present invention ・−−−−−−−−−−−−−−
-20 parts clay ・−・−−−−−・・
-・70 parts white carbon・----1---・・
-... 10 parts or more are mixed uniformly, and the active ingredient is 20%.
Obtain a powder.
１剋■工 粒剤
本発明化合物 −・−・−一一−−−−−−−−
・ ５部ベントナイト −・−・−一−−−・・
−・ ２５部タルク −・−・−一−−−
・−−−一−−・ ７０部以上を均一に混合粉砕して後
、少量の水を加えて撹拌混合捏和し、押出式造粒機で造
粒し、乾燥して粒剤にする。1剋■工 Granules Compound of the present invention -・-・-11----------------------
・ 5 parts bentonite −・−・−1−−−・・
−・25 parts talc −・−・−1−−−
----1---- After uniformly mixing and pulverizing 70 parts or more, a small amount of water is added, stirring and kneading is carried out, granulation is performed using an extrusion type granulator, and the mixture is dried to form granules.
次に、本発明化合物の土壌病害防除剤剤としての有用性
を以下の試験例において具体的に説明する。Next, the usefulness of the compound of the present invention as a soil disease control agent will be specifically explained in the following test examples.
跋ＭＪＩ上 十字花科植物根こぶ病防除試験（乳剤処理
）
直径８ｏのプラスチック製ポットに滅菌土壌を詰め、ハ
クサイ（品種二金将２号）をポット当たり３粗描種した
。このポット表面に製剤例に示した乳剤を所定濃度に希
釈し、ポット当たり１０ｍ１を潅注処理した。処理翌日
、十字花科植物根こぶ病１１（ＰＩ鉦肚虹並蝕組ｂｒａ
ｓｓｉｃａｅ）の感染によって形成されたハクサイの根
こぶをポット当たり１ｇホモジネートして得た十字花科
植物根こぶ病菌休眠胞子浮遊液をポット表面に潅注する
ことにより接種した。これをガラス温室内に置き、ハク
サイを生育させ、接種５週目に根部の発育状態を調査し
下記の計算式により防除価を算出した。跋MJI Upper Cruciformaceae plant clubroot control test (emulsion treatment) Plastic pots with a diameter of 8o were filled with sterilized soil, and three rough seeds of Chinese cabbage (variety Nikin-sho No. 2) were seeded per pot. The emulsion shown in the formulation example was diluted to a predetermined concentration and 10 ml per pot was irrigated onto the surface of this pot. The day after treatment, the clubroot disease 11 of cruciferous plants (PI
The pot surface was inoculated with a suspension of dormant spores of the crucianaceae root gall fungus, which was obtained by homogenizing 1 g of Chinese cabbage root gall per pot, which was formed by infection with C. ssicae. This was placed in a glass greenhouse, Chinese cabbage was allowed to grow, and the state of root growth was investigated 5 weeks after inoculation, and the control value was calculated using the following formula.
ｎｅｔ根こぶの着生が認められない固体数。Number of individuals in which root galls are not observed.
ｎｌ：根こぶが支根のみに着生している固体数。nl: Number of individuals with root galls growing only on supporting roots.
ｎ８：根こぶが支根、主根の両方に着生しているがあま
り肥大していない固体数。n8: Number of individuals in which root galls are attached to both the branch root and the main root, but are not very enlarged.
ｎ、：根こぶが支根、主根の両方に着生しており肥大が
著しい固体数。n,: Number of individuals with root galls growing on both the branch roots and the main root, which are significantly enlarged.
Ｎ；全調査固体数。N: Total number of surveyed individuals.
対照薬剤にはＰＣＮＢ水和剤（有効成分７５％）を使用
した。PCNB hydrating agent (75% active ingredient) was used as a control drug.
結果を第２表に示す。The results are shown in Table 2.
第２表
化合物 を効成分処理量（Ｋｇ／ｈａ）２
１ ０．５ ０．２
Ｎｏ、４ １００ １００ ８０ ５Ｏ
Ｎｏ、５ １００ １００ ９１ ５５
Ｎｏ、６ １００ １００ １００ ９
３Ｎｏ、７ １００ １００ １００
８５Ｎｏ、８ １００ １００ １００
１００Ｎｏ、９ １００ １００ １０
０ ９３比較化合物Ａ ００００
比較化合物Ｂ ３０ ０ ０ ０比
較化合物Ｃ８０６０００
比較化合物Ｄ ００００
比較化合物Ｅ ００００
比較化合物Ｆ ８１ ８０ ４２ ０比
較化合物Ｇ ７７ ４０ ０ ０ＰＣ
ＮＢ ０ ０ ０ Ｑ第２
表中の比較化合物Ａ〜Ｅは特開昭６０−１５２４０１号
公報に具体的に記載されている化合物で、比較化合物Ｆ
およびＧは特開昭６２−１６４６５号公報に具体的に記
載されている化合物であり、下記の構造式％式％）
ＰＣＮＢはペンタクロルニトロベンゼンで下記の造を有
する市販の土壌病害防除剤である。Compounds in Table 2 are treated as active ingredients (Kg/ha)2
1 0.5 0.2 No, 4 100 100 80 5O
No, 5 100 100 91 55
No, 6 100 100 100 9
3No, 7 100 100 100
85No, 8 100 100 100
100No, 9 100 100 10
0 93 Comparative compound A 0000 Comparative compound B 30 0 0 0 Comparative compound C 806000 Comparative compound D 0000 Comparative compound E 0000 Comparative compound F 81 80 42 0 Comparative compound G 77 40 0 0 PC
NB 0 0 0 Q 2nd
Comparative compounds A to E in the table are compounds specifically described in JP-A-60-152401, and comparative compound F
and G are the compounds specifically described in JP-A No. 62-16465, and have the following structural formula (% formula %) PCNB is pentachlornitrobenzene and is a commercially available soil disease control agent having the following structure. .
Ｗ 十字花科植物根こぶ病防除試験（粉剤処理）
滅菌土壌１８０ｇと本発明化合物を５％、２％、１％、
０．５％および０．２％含有するそれぞれの粉剤５０ｍ
ｇとをよく混和し、ａ ／ ２００００ボツトに詰め、
ハクサイ（品種：金将２号）をポット当たり３粒播種し
た。処理翌日、十字花科植物根こぶ病菌（Ｐｌａｓ肌虹
並肢■ｂｒａｓｓ １ｃａｅ）の感染によって形成され
たハクサイの根こぶをポット当たり１ｇホモジネートし
て得た十字花科植物根こぶ病菌休眠胞子浮遊液をポット
表面に潅注することにより接種した。これをガラス温室
内に置き、ハクサイを生育させ、接種５週目に根部の発
育状態を調査し試験例１と同様の方法によって防除価を
算出した。但し、対照薬剤にはＰＣＮＢ粉剤（有効成分
５％）５０ｍｇを使用した。W Cruciform plant clubroot control test (powder treatment) 180 g of sterilized soil and the compound of the present invention at 5%, 2%, 1%,
50m of each powder containing 0.5% and 0.2%
Mix well with g and pack into a/20000 bottles,
Three seeds of Chinese cabbage (variety: Kinsho No. 2) were sown per pot. On the day after treatment, 1 g of Chinese cabbage root galls formed by infection with Plass brassicae were homogenized per pot on the next day. was inoculated by irrigating the surface of the pot. This was placed in a glass greenhouse, Chinese cabbage was grown, and the state of root growth was investigated 5 weeks after inoculation, and the control value was calculated using the same method as in Test Example 1. However, 50 mg of PCNB powder (5% active ingredient) was used as a control drug.
結果を第３表に示す。The results are shown in Table 3.
第３表
化合物 有効成分処理量（Ｋｇ／ｈａ）５ ２
１ ０．５ ０．２Ｎｏ、６ １０
０ １００ １００ １００ ８９Ｎｏ、８
１００ １００ １００ １００ １
００Ｎｏ、９ １００ １００ １００
１００ ９６比較化合物Ｃ９０７５５０００
比較化合物Ｆ １００ ９０ ８０ ３０
０ＰＣＮＢ ０ ０ ０
０ ０（以下、余白）
跋肢糎主 薬害試験
直径８ｃｍのプラスチック製ポットに滅菌土壌を詰め、
ハクサイの種（品種：余得２号）をポット当たり３粒播
種した。Table 3 Compound Active ingredient processing amount (Kg/ha) 5 2
1 0.5 0.2No, 6 10
0 100 100 100 89No, 8
100 100 100 100 1
00No, 9 100 100 100
100 96 Comparative Compound C90755000 Comparative Compound F 100 90 80 30
0PCNB 0 0 0
0 0 (hereinafter referred to as blank space) Lame limbs Phytotoxicity test A plastic pot with a diameter of 8 cm was filled with sterilized soil.
Three Chinese cabbage seeds (variety: Yotoku No. 2) were sown per pot.
このポット土壌表面に製剤例に示した乳剤を所定濃度に
希釈して、ポット当たり１０−１を潅注処理した。この
ポットをガラス温室内に置き、播種３週間後に薬害の存
無を肉眼観察した。The emulsion shown in the formulation example was diluted to a predetermined concentration and 10-1 per pot was irrigated onto the soil surface of this pot. This pot was placed in a glass greenhouse, and 3 weeks after sowing, the presence or absence of chemical damage was visually observed.
結果を第４表にしめす。The results are shown in Table 4.
（以下、余白）
第４表
化合物 有効成分処理量（Ｋｇ／ｈａ）Ｎｏ、
４ ０ ０ ＯＮｏ、５
０ ０ ＯＮｏ、６ ０ ０
ＯＮｏ、７ ０ ０ ＯＮｏ、８
０ ０ ＯＮｏ、９ ０
０ ０
比較化合物Ａ ２００
比較化合物Ｂ ５ ２ １
比較化合物Ｃ５２１
比較化合物Ｄ ３ ０ ０
比較化合物Ｅ ４ ０ ０
第４表中のＯ〜５のデータの定義は以下のとおり０・−
・−一一一一・地上部生育が無処理区と略同じ（薬害が
ほとんど認められない）
１−−−−−−−−一地上部生育が無処理区の８１〜９
５χ程度（薬害が若干認められる）
２・・−・・−地上部生育が無処理区の７１〜８０χ程
度（薬害が少し認められる）
３−−−−−−−−−・地上部生育が無処理区の６１〜
７０χ程度（薬害がかなり認められる）
４−−−−−−一・−地上部生育が無処理区 ５０〜６
０％以下（薬害が相当認められる）
５−−−−−−−−一・はぼ完全枯死
（薬害が甚大である。）
特許出願人 日産化学工業株式会社
保土谷化学工業株式会社(Hereinafter, blank space) Table 4 Compound Active ingredient processing amount (Kg/ha) No.
4 0 0 ONo, 5
0 0 ONo, 6 0 0
ONo, 7 0 0 ONo, 8
0 0 ONo, 9 0
0 0 Comparative Compound A 200 Comparative Compound B 5 2 1 Comparative Compound C521 Comparative Compound D 3 0 0 Comparative Compound E 4 0 0 The definitions of the data for O to 5 in Table 4 are as follows: 0.-
・-1111・Growth of the aboveground part is almost the same as that of the untreated area (almost no chemical damage is observed)
Approximately 5χ (some drug damage is observed) 2.---- Aboveground growth is approximately 71 to 80χ of the untreated area (some drug damage is observed) 3. 61~ in untreated area
Approximately 70χ (considerable chemical damage is observed) 4--------1.- Aboveground growth is untreated 50-6
0% or less (Significant chemical damage is observed) 5. Complete withering of plants (Significant chemical damage is observed.) Patent applicant: Nissan Chemical Industries, Ltd. Hodogaya Chemical Industry Co., Ltd.
Claims (6)
示す。）で表されるベンズアミド誘導体もしくはそれら
の塩類。(1) General formula (I): ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) A benzamide derivative or those salts.
範囲第１項記載のベンズアミド誘導体もしくはそれらの
塩類。(2) Benzamide derivatives or salts thereof according to claim 1, wherein X is a chlorine atom and n is an integer of 2.
が、２位と４位である特許請求の範囲第１項記載のベン
ズアミド誘導体もしくはそれらの塩類。(3) The benzamide derivative or salt thereof according to claim 1, wherein X is a chlorine atom, n is an integer of 2, and the substitution positions of X are the 2nd and 4th positions.
示す。）で表されるベンズアミド誘導体もしくはそれら
の塩類の少なくとも１種を有効成分として含有すること
を特徴とする土壌病害防除剤。(4) General formula (I): ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (I) A benzamide derivative or A soil disease control agent characterized by containing at least one of these salts as an active ingredient.
ド誘導体を有効成分とする特許請求の範囲第４項記載の
土壌病害防除剤。(5) The soil disease control agent according to claim 4, wherein the active ingredient is a benzamide derivative in which X is a chlorine atom and n is an integer of 2.
が、２位と４位であるベンズアミド誘導体を有効成分と
する特許請求の範囲第４項記載の土壌病害防除剤。(6) The soil disease control agent according to claim 4, wherein the active ingredient is a benzamide derivative in which X is a chlorine atom, n is an integer of 2, and X is substituted at the 2nd and 4th positions.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10204787A JPS63267754A (en) | 1987-04-27 | 1987-04-27 | Benzamide derivative and soil disease-controlling agent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10204787A JPS63267754A (en) | 1987-04-27 | 1987-04-27 | Benzamide derivative and soil disease-controlling agent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS63267754A true JPS63267754A (en) | 1988-11-04 |
Family
ID=14316855
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10204787A Pending JPS63267754A (en) | 1987-04-27 | 1987-04-27 | Benzamide derivative and soil disease-controlling agent |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63267754A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0659738A1 (en) * | 1993-12-22 | 1995-06-28 | Eastman Kodak Company | N-(Carbonyl, carbonimidoyl, carbonothioyl) sulfonamide charge control agents and toners and developers |
-
1987
- 1987-04-27 JP JP10204787A patent/JPS63267754A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0659738A1 (en) * | 1993-12-22 | 1995-06-28 | Eastman Kodak Company | N-(Carbonyl, carbonimidoyl, carbonothioyl) sulfonamide charge control agents and toners and developers |
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