JPS60243061A

JPS60243061A - ベンズアニリド誘導体及びそれを含有する除草剤

ベンズアニリド誘導体及びそれを含有する除草剤

Info

Publication number: JPS60243061A
Authority: JP; Japan
Prior art keywords: compound; parts; solution; dissolved; chlorotrifluoromethanesulfonanilide
Prior art date: 1984-05-17
Legal status : Granted

Application number

JP9755084A

Other languages

English (en)

Japanese (ja)

Other versions

JPH0412263B2 (enrdf_load_stackoverflow

Inventor

Tetsuo Takematsu

竹松　哲夫

Takeo Mogi

茂木　武雄

Yasunari Sakuraba

桜庭　保也

Masaaki Hoya

保谷　正明

Shinichi Matsuno

真一松野

Current Assignee

Hodogaya Chemical Co Ltd

Original Assignee

Hodogaya Chemical Co Ltd

Priority date

1984-05-17

Filing date

1984-05-17

Publication date

1985-12-03

1984-05-17 Application filed by Hodogaya Chemical Co Ltd filed Critical Hodogaya Chemical Co Ltd

1984-05-17 Priority to JP9755084A priority Critical patent/JPS60243061A/ja

1985-12-03 Publication of JPS60243061A publication Critical patent/JPS60243061A/ja

1992-03-04 Publication of JPH0412263B2 publication Critical patent/JPH0412263B2/ja

Status Granted legal-status Critical Current

Links

230000002363 herbicidal effect Effects 0.000 title claims abstract description 16
239000004009 herbicide Substances 0.000 title claims abstract description 9
ZVSKZLHKADLHSD-UHFFFAOYSA-N benzanilide Chemical class C=1C=CC=CC=1C(=O)NC1=CC=CC=C1 ZVSKZLHKADLHSD-UHFFFAOYSA-N 0.000 title claims description 8
229910052801 chlorine Inorganic materials 0.000 claims abstract 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 3
125000001309 chloro group Chemical group Cl* 0.000 claims 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
150000001875 compounds Chemical class 0.000 abstract description 41
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract description 18
238000006243 chemical reaction Methods 0.000 abstract description 17
241000196324 Embryophyta Species 0.000 abstract description 10
WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 abstract description 6
-1 trifluoromethanesulfonyl halide Chemical class 0.000 abstract description 6
241000234646 Cyperaceae Species 0.000 abstract description 5
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical class ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 abstract description 4
AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 abstract description 3
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 abstract 2
239000012442 inert solvent Substances 0.000 abstract 1
239000000463 material Substances 0.000 abstract 1
229910000029 sodium carbonate Inorganic materials 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 50
239000000243 solution Substances 0.000 description 25
241000209094 Oryza Species 0.000 description 18
235000007164 Oryza sativa Nutrition 0.000 description 16
230000015572 biosynthetic process Effects 0.000 description 16
235000009566 rice Nutrition 0.000 description 16
239000000126 substance Substances 0.000 description 16
238000003786 synthesis reaction Methods 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
238000003756 stirring Methods 0.000 description 12
239000008187 granular material Substances 0.000 description 11
239000000839 emulsion Substances 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
239000003795 chemical substances by application Substances 0.000 description 8
241001076438 Oxya japonica Species 0.000 description 7
238000001704 evaporation Methods 0.000 description 7
230000008020 evaporation Effects 0.000 description 7
230000008018 melting Effects 0.000 description 7
238000002844 melting Methods 0.000 description 7
239000002904 solvent Substances 0.000 description 7
238000011282 treatment Methods 0.000 description 7
239000005995 Aluminium silicate Substances 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000004480 active ingredient Substances 0.000 description 6
235000012211 aluminium silicate Nutrition 0.000 description 6
239000004927 clay Substances 0.000 description 6
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
238000003973 irrigation Methods 0.000 description 6
230000002262 irrigation Effects 0.000 description 6
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 6
239000000203 mixture Substances 0.000 description 6
239000002689 soil Substances 0.000 description 6
241000218691 Cupressaceae Species 0.000 description 5
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
239000002270 dispersing agent Substances 0.000 description 5
239000003814 drug Substances 0.000 description 5
229940079593 drug Drugs 0.000 description 5
239000003995 emulsifying agent Substances 0.000 description 5
238000005406 washing Methods 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
239000000440 bentonite Substances 0.000 description 4
229910000278 bentonite Inorganic materials 0.000 description 4
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 4
HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
239000000454 talc Substances 0.000 description 4
229910052623 talc Inorganic materials 0.000 description 4
239000008096 xylene Substances 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
239000000843 powder Substances 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 description 2
239000004343 Calcium peroxide Substances 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
241000254158 Lampyridae Species 0.000 description 2
231100000674 Phytotoxicity Toxicity 0.000 description 2
229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
LHJQIRIGXXHNLA-UHFFFAOYSA-N calcium peroxide Chemical compound [Ca+2].[O-][O-] LHJQIRIGXXHNLA-UHFFFAOYSA-N 0.000 description 2
235000019402 calcium peroxide Nutrition 0.000 description 2
235000013339 cereals Nutrition 0.000 description 2
230000018044 dehydration Effects 0.000 description 2
238000006297 dehydration reaction Methods 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
238000011156 evaluation Methods 0.000 description 2
238000009472 formulation Methods 0.000 description 2
230000012010 growth Effects 0.000 description 2
238000010898 silica gel chromatography Methods 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
235000019832 sodium triphosphate Nutrition 0.000 description 2
238000009331 sowing Methods 0.000 description 2
239000004094 surface-active agent Substances 0.000 description 2
GAVRKMGLLRRNRS-UHFFFAOYSA-N 1-propan-2-yl-4-[(4-propan-2-ylphenyl)methyl]benzene Chemical compound C1=CC(C(C)C)=CC=C1CC1=CC=C(C(C)C)C=C1 GAVRKMGLLRRNRS-UHFFFAOYSA-N 0.000 description 1
YBONBWJSFMTXLE-UHFFFAOYSA-N 2,3-dichlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC(Cl)=C1Cl YBONBWJSFMTXLE-UHFFFAOYSA-N 0.000 description 1
RSINFFVFOTUDEC-UHFFFAOYSA-N 2,5-dichlorobenzoyl chloride Chemical compound ClC(=O)C1=CC(Cl)=CC=C1Cl RSINFFVFOTUDEC-UHFFFAOYSA-N 0.000 description 1
HTFNVAVTYILUCF-UHFFFAOYSA-N 2-[2-ethoxy-4-[4-(4-methylpiperazin-1-yl)piperidine-1-carbonyl]anilino]-5-methyl-11-methylsulfonylpyrimido[4,5-b][1,4]benzodiazepin-6-one Chemical compound CCOc1cc(ccc1Nc1ncc2N(C)C(=O)c3ccccc3N(c2n1)S(C)(=O)=O)C(=O)N1CCC(CC1)N1CCN(C)CC1 HTFNVAVTYILUCF-UHFFFAOYSA-N 0.000 description 1
NQUVCRCCRXRJCK-UHFFFAOYSA-N 4-methylbenzoyl chloride Chemical compound CC1=CC=C(C(Cl)=O)C=C1 NQUVCRCCRXRJCK-UHFFFAOYSA-N 0.000 description 1
241000254032 Acrididae Species 0.000 description 1
241000254060 Aquatica lateralis Species 0.000 description 1
244000025254 Cannabis sativa Species 0.000 description 1
241000238008 Cerithidea rhizophorarum Species 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
244000060011 Cocos nucifera Species 0.000 description 1
235000013162 Cocos nucifera Nutrition 0.000 description 1
239000004606 Fillers/Extenders Substances 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
241000759137 Schoenoplectiella juncoides Species 0.000 description 1
235000005324 Typha latifolia Nutrition 0.000 description 1
241000607479 Yersinia pestis Species 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000003905 agrochemical Substances 0.000 description 1
150000001346 alkyl aryl ethers Chemical class 0.000 description 1
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
239000012752 auxiliary agent Substances 0.000 description 1
239000000969 carrier Substances 0.000 description 1
244000118869 coast club rush Species 0.000 description 1
239000004020 conductor Substances 0.000 description 1
235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 1
YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
YHAIUSTWZPMYGG-UHFFFAOYSA-L disodium;2,2-dioctyl-3-sulfobutanedioate Chemical compound [Na+].[Na+].CCCCCCCCC(C([O-])=O)(C(C([O-])=O)S(O)(=O)=O)CCCCCCCC YHAIUSTWZPMYGG-UHFFFAOYSA-L 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
239000012456 homogeneous solution Substances 0.000 description 1
238000011221 initial treatment Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000006166 lysate Substances 0.000 description 1
239000012046 mixed solvent Substances 0.000 description 1
NZPDRHANMCHMRF-UHFFFAOYSA-N n-chloro-1,1,1-trifluoro-n-phenylmethanesulfonamide Chemical compound FC(F)(F)S(=O)(=O)N(Cl)C1=CC=CC=C1 NZPDRHANMCHMRF-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
238000010899 nucleation Methods 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
230000000885 phytotoxic effect Effects 0.000 description 1
239000005648 plant growth regulator Substances 0.000 description 1
229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
238000010298 pulverizing process Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000001568 sexual effect Effects 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
JBJWASZNUJCEKT-UHFFFAOYSA-M sodium;hydroxide;hydrate Chemical compound O.[OH-].[Na+] JBJWASZNUJCEKT-UHFFFAOYSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
239000004563 wettable powder Substances 0.000 description 1