JPH0377861A - Fluorine-containing sulfonamide derivative, insecticide and acaricide - Google Patents
Fluorine-containing sulfonamide derivative, insecticide and acaricideInfo
- Publication number
- JPH0377861A JPH0377861A JP21244089A JP21244089A JPH0377861A JP H0377861 A JPH0377861 A JP H0377861A JP 21244089 A JP21244089 A JP 21244089A JP 21244089 A JP21244089 A JP 21244089A JP H0377861 A JPH0377861 A JP H0377861A
- Authority
- JP
- Japan
- Prior art keywords
- group
- groups
- fluorine
- insecticide
- acaricide
- 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
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title claims abstract description 9
- 229910052731 fluorine Inorganic materials 0.000 title claims abstract description 9
- 239000011737 fluorine Substances 0.000 title claims abstract description 9
- 239000002917 insecticide Substances 0.000 title claims abstract description 9
- HFFXLYHRNRKAPM-UHFFFAOYSA-N 2,4,5-trichloro-n-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide Chemical compound O1C(C)=CC(NS(=O)(=O)C=2C(=CC(Cl)=C(Cl)C=2)Cl)=N1 HFFXLYHRNRKAPM-UHFFFAOYSA-N 0.000 title claims abstract description 8
- 230000000895 acaricidal effect Effects 0.000 title claims abstract description 8
- 239000000642 acaricide Substances 0.000 title claims abstract description 8
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 4
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract 5
- 239000004480 active ingredient Substances 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract description 19
- 150000001875 compounds Chemical class 0.000 abstract description 17
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract description 12
- 241000607479 Yersinia pestis Species 0.000 abstract description 8
- 241000238631 Hexapoda Species 0.000 abstract description 6
- 238000001816 cooling Methods 0.000 abstract description 4
- 230000000749 insecticidal effect Effects 0.000 abstract description 4
- 239000003125 aqueous solvent Substances 0.000 abstract description 3
- FURHRJBOFNDYTG-UHFFFAOYSA-N 2-fluoroethanamine Chemical compound NCCF FURHRJBOFNDYTG-UHFFFAOYSA-N 0.000 abstract description 2
- 241000238657 Blattella germanica Species 0.000 abstract description 2
- 241000257159 Musca domestica Species 0.000 abstract description 2
- 238000003898 horticulture Methods 0.000 abstract description 2
- 241000218475 Agrotis segetum Species 0.000 abstract 1
- 241001414720 Cicadellidae Species 0.000 abstract 1
- 241000256059 Culex pipiens Species 0.000 abstract 1
- 241000578422 Graphosoma lineatum Species 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- UBJSQINEQMPTID-UHFFFAOYSA-N n-(2-fluoroethyl)benzenesulfonamide Chemical compound FCCNS(=O)(=O)C1=CC=CC=C1 UBJSQINEQMPTID-UHFFFAOYSA-N 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 abstract 1
- 238000012360 testing method Methods 0.000 description 8
- 239000000843 powder Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- -1 glymes Chemical compound 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 4
- 239000004927 clay Substances 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241001466042 Fulgoromorpha Species 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 241001454293 Tetranychus urticae Species 0.000 description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
- QNLZIZAQLLYXTC-UHFFFAOYSA-N 1,2-dimethylnaphthalene Chemical compound C1=CC=CC2=C(C)C(C)=CC=C21 QNLZIZAQLLYXTC-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
- 241000238876 Acari Species 0.000 description 2
- 241001124076 Aphididae Species 0.000 description 2
- 241000239290 Araneae Species 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 241001454295 Tetranychidae Species 0.000 description 2
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 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 2
- 230000000694 effects Effects 0.000 description 2
- 230000000887 hydrating effect Effects 0.000 description 2
- 239000011490 mineral wool Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000035699 permeability Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ZMESHQOXZMOOQQ-UHFFFAOYSA-N 1-(naphthalen-1-ylmethyl)naphthalene Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 ZMESHQOXZMOOQQ-UHFFFAOYSA-N 0.000 description 1
- VEZJSKSPVQQGIS-UHFFFAOYSA-N 1-chloro-2-fluoroethane Chemical compound FCCCl VEZJSKSPVQQGIS-UHFFFAOYSA-N 0.000 description 1
- LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 1
- YRRZGBOZBIVMJT-UHFFFAOYSA-N 2-fluoroethanamine;hydron;chloride Chemical compound Cl.NCCF YRRZGBOZBIVMJT-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 241001143309 Acanthoscelides obtectus Species 0.000 description 1
- 241001600408 Aphis gossypii Species 0.000 description 1
- 241000206761 Bacillariophyta Species 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
- 101150041968 CDC13 gene Proteins 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241001498622 Cixius wagneri Species 0.000 description 1
- 241000254173 Coleoptera Species 0.000 description 1
- 240000008067 Cucumis sativus Species 0.000 description 1
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 1
- 241000256054 Culex <genus> Species 0.000 description 1
- 241000255925 Diptera Species 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 241000258937 Hemiptera Species 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241000255777 Lepidoptera Species 0.000 description 1
- 241001556089 Nilaparvata lugens Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000238814 Orthoptera Species 0.000 description 1
- 241000320508 Pentatomidae Species 0.000 description 1
- 241000500437 Plutella xylostella Species 0.000 description 1
- 241000500441 Plutellidae Species 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 241000254062 Scarabaeidae Species 0.000 description 1
- 206010041235 Snoring Diseases 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 241000256248 Spodoptera Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 241000488589 Tetranychus kanzawai Species 0.000 description 1
- 241000339373 Thrips palmi Species 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- JYFJNCCRKBBRKZ-UHFFFAOYSA-N chembl194764 Chemical compound C=1C=CC=C(F)C=1CCN1C(=O)C(CC)=C(C)N=C1C1=CC=CC=C1O JYFJNCCRKBBRKZ-UHFFFAOYSA-N 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- AVXHCUKQISJQBN-UHFFFAOYSA-N chloromethanesulfonamide Chemical compound NS(=O)(=O)CCl AVXHCUKQISJQBN-UHFFFAOYSA-N 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- PHHWLDOIMGFHOZ-UHFFFAOYSA-L disodium;dinaphthalen-1-ylmethanedisulfonate Chemical compound [Na+].[Na+].C1=CC=C2C(C(C=3C4=CC=CC=C4C=CC=3)(S(=O)(=O)[O-])S([O-])(=O)=O)=CC=CC2=C1 PHHWLDOIMGFHOZ-UHFFFAOYSA-L 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- RSOJSFYJLQADDM-UHFFFAOYSA-N ethanesulfonamide Chemical compound [CH2]CS(N)(=O)=O RSOJSFYJLQADDM-UHFFFAOYSA-N 0.000 description 1
- FRYHCSODNHYDPU-UHFFFAOYSA-N ethanesulfonyl chloride Chemical compound CCS(Cl)(=O)=O FRYHCSODNHYDPU-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 230000032696 parturition Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
[産業上の利用分野1
本発明は、新規な含フツ素スルホンアミド誘導体および
それを有効成分とするこん虫頬、ダニ類等の有害生物の
防除剤に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application 1] The present invention relates to a novel fluorine-containing sulfonamide derivative and an agent for controlling pests such as worms and mites containing the same as an active ingredient.
[従来の技術]
従来から種々のスルホンアミド誘導体が有害生物防除剤
として報告されている。例えば、特公昭46−2801
4号公報にはクロルメタンスルホンアミドがハダニ類に
有用であることが開示されており、また、特開昭54−
61)47号公報、特開昭55−38354−号公報お
よび特開昭63−J52O5号公報にもダニ類に有用で
あることが開示されている。[Prior Art] Various sulfonamide derivatives have been reported as pest control agents. For example, Tokuko Sho 46-2801
Publication No. 4 discloses that chlormethanesulfonamide is useful against spider mites, and Japanese Patent Application Laid-open No. 1983-
61) No. 47, JP-A-55-38354-A, and JP-A-63-J52O5 also disclose that it is useful against mites.
また、含フツ素化合物では特開昭63−227552号
公報に、一般式;
で表わされる2−フルオロエチル銹滑1体が有害生物防
除剤として有用であるとして開示されているが、2−フ
ルオロエチル誘導体の浸透移行性については何らの示唆
もされていない。Regarding fluorine-containing compounds, JP-A No. 63-227552 discloses that 2-fluoroethyl chloride represented by the general formula; is useful as a pest control agent; There is no suggestion whatsoever regarding the permeability of ethyl derivatives.
[発明が解決しようとする問題点]
本発明者らは、この浸透移行性を活用した土壌処理にお
いて有効に有害生物を防除できる薬Mを開発すべく鋭意
研究を重ねた結果、以下の一般式CI)に示される化合
物に高い浸透移行性を有することを見いだし、本発明を
完成するに到った。[Problems to be Solved by the Invention] The present inventors have conducted extensive research to develop a drug M that can effectively control pests in soil treatment that utilizes this osmotic transfer property, and as a result, the following general formula has been developed. It was discovered that the compound shown in CI) has high permeability, and the present invention was completed.
[問題点を解決するための手段]
本発明は、一般式(夏)
R−3o、−NHCH,CH,F (I)[式中、
RはC1〜C4のアルキル基、ハロアルキル基、シクロ
アルキル基、ナフチル基、ベンジ(ここでXは水素、C
1〜C4のアルキル基、ハロアルキル基、ベンジル基、
ニトロ基、チエニル基およびシアノ基を示し、mは1〜
2を示す。)を示す、]にて示される新規な含フツ素ス
ルホンアミド誘導体およびこの化合物を有効成分とする
有害生物防除剤を提供するものである。[Means for Solving the Problems] The present invention provides a general formula (summer) R-3o, -NHCH,CH,F (I) [in the formula,
R is a C1-C4 alkyl group, haloalkyl group, cycloalkyl group, naphthyl group, benzene (where X is hydrogen, C
1-C4 alkyl group, haloalkyl group, benzyl group,
It represents a nitro group, a thienyl group, and a cyano group, and m is 1 to
2 is shown. The present invention provides a novel fluorine-containing sulfonamide derivative represented by ) and a pest control agent containing this compound as an active ingredient.
本発明の弐H)の化合物は以下の方法により製造できる
。Compound 2H) of the present invention can be produced by the following method.
[方法1]
一般式
%式%()
(式中、Rは前記と同1)1)である。)で示されるス
ルホニルクロリド誘導体とモノフルオロエチルアミンを
水系溶媒または非水系溶媒中で塩基の存在下、氷冷〜5
0℃の間の反応温度で反応させる。[Method 1] General formula % formula % () (wherein R is the same as above 1) 1). ) and monofluoroethylamine in an aqueous or non-aqueous solvent in the presence of a base, ice-cooled to
The reaction is carried out at a reaction temperature between 0°C.
溶媒としては、水、塩化メチレン、クロロホルム、四塩
化炭素等のハロゲン化炭化水素類、ベンゼン、トルエン
、キシレン等の芳香族炭化水素類、ジエチルエーテル、
THF、ジオキサン、グライム類等のエーテル類、DM
F%DMSO等が塔げられる。塩基としては、炭酸ナト
リウム、炭酸カリウム、水酸化ナトリウム、水酸化カリ
ウム、水素化ナトリウム等の無機塩基またはトリエチル
アミン、ピリジン、ジメチルアミノピリジン、DBU、
、DBN等の有機塩基が挙げられる。Examples of solvents include water, halogenated hydrocarbons such as methylene chloride, chloroform, and carbon tetrachloride, aromatic hydrocarbons such as benzene, toluene, and xylene, diethyl ether,
THF, dioxane, ethers such as glymes, DM
F%DMSO etc. are removed. Examples of the base include inorganic bases such as sodium carbonate, potassium carbonate, sodium hydroxide, potassium hydroxide, and sodium hydride, or triethylamine, pyridine, dimethylaminopyridine, DBU,
, DBN, and other organic bases.
[方法2]
一般式
%式%()
(式中、Rは前記と同意義である。)で示される化合物
と一般式
%式%()
(式中、XはCI、BrまたはIを意味するや)で示さ
れる化合物を溶媒中塩基存在下で氷冷〜連流の間の反応
温度で反応させる。溶媒および塩基としては方法1と同
じものが挙げられる。[Method 2] A compound represented by the general formula % formula % () (wherein R has the same meaning as above) and a compound represented by the general formula % formula % () (wherein, X means CI, Br or I A compound represented by Suruya) is reacted in a solvent in the presence of a base at a reaction temperature between ice cooling and continuous flow. The same solvent and base as in Method 1 can be used.
次に実施例を挙げ本発明をさらに詳細に説明する。Next, the present invention will be explained in more detail with reference to Examples.
実施例1(化合物1)
N−2−フルオロエチル 〜0ンセ9ンスルネンアミド
のムク−フルオロエチルアミン塩酸塩9.95g (
0,1モル)を塩化メチレン80dに懸濁し、トリエチ
ルアミン30.4m (0,22モル)を添加した。水
冷下、塩化ベンゼンスルホニル17゜66 g (0,
1モル)を塩化メチレン30mに溶解し、滴下した。滴
下後、室温まで昇温し、8時間攪拌した。反応後、塩化
エチルで希釈し、水洗し、無水硫酸マグネシウムで乾燥
した。溶媒を留去し、n〜ヘキザンを加え結晶化させた
後、結晶を0知し、乾燥した。酢酸エチル/ローヘキサ
ンより再結晶をおこない、ト(2−フルオロエチル)ベ
ンゼンスルホンア逼ド(19,25g、 収194.7
%)の無色結晶を得た。Example 1 (Compound 1) 9.95 g of N-2-fluoroethyl to 9-fluoroethylamine hydrochloride (
0.1 mol) was suspended in 80 d of methylene chloride, and 30.4 m (0.22 mol) of triethylamine was added. Under water cooling, benzenesulfonyl chloride 17°66 g (0,
1 mol) was dissolved in 30 m of methylene chloride and added dropwise. After the dropwise addition, the temperature was raised to room temperature and stirred for 8 hours. After the reaction, it was diluted with ethyl chloride, washed with water, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and hexane was added to cause crystallization, and then the crystals were evaporated and dried. Recrystallization from ethyl acetate/low hexane yielded tho(2-fluoroethyl)benzenesulfonate (19.25 g, yield: 194.7
%) of colorless crystals were obtained.
融点:97〜98℃
’H−NMR(CDCl5 ) :
63.32(d−d−t、J=6Hz、J”5Hz、2
H) 、4.45(d−t、J=48Hz、J−5Hz
、2H)、5.17(broad t、J=6Hz、I
H)、7.4−8.05(鳳51 )
実施例2(化合物2)
N−2−フルすlffX4ル エタンスに本ンアミビの
2−フルオロエチルアミン塩酸塩1.50g (15ミ
リモル)を塩化メチレン30s&に懸濁し、トリエチル
アミン4.5 m (33ミリモル)を添加した。水冷
下、塩化エタンスルホニル1.93g (15ミリモル
)を塩化メチレン20−に溶解し、滴下した。Ws上下
後室温まで昇温し、−晩撹拌した。反応後、水洗し、無
水硫酸マグネシウムで乾燥した。溶媒を菅去し、残渣を
シリカゲルクロマトグラフィー(塩化メチレン)で精製
し、ト(2−フルオロエチル)エタンスルホンアミド(
1,48g、収率80.0%)を淡黄色粘稠体として得
た。Melting point: 97-98°C 'H-NMR (CDCl5): 63.32 (d-d-t, J=6Hz, J''5Hz, 2
H), 4.45 (d-t, J=48Hz, J-5Hz
, 2H), 5.17 (broad t, J=6Hz, I
H), 7.4-8.05 (Otori 51) Example 2 (Compound 2) 1.50 g (15 mmol) of 2-fluoroethylamine hydrochloride of this amino acid was added to N-2-fluorethyl ethane in methylene chloride. 30 s & 4.5 m (33 mmol) of triethylamine was added. Under water cooling, 1.93 g (15 mmol) of ethanesulfonyl chloride was dissolved in 20-methylene chloride and added dropwise. After raising and lowering Ws, the temperature was raised to room temperature and stirred overnight. After the reaction, it was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed, and the residue was purified by silica gel chromatography (methylene chloride) to give tho(2-fluoroethyl)ethanesulfonamide (
1.48 g (yield: 80.0%) was obtained as a pale yellow viscous body.
’H−NMR(CDC13) :
6 1.44(t、J=8Hz、3H)、3.18(q
、J=8)1z、2H)、3.54(d−d−t、J=
27Hz、J=6Hz、J=5Hz、2N> 、4.6
2(d−t、J=49HzJ=5Hz、2H)、5.2
6(broad t、J=6Hz。IH)実施例3〜4
4(化合物3〜44)
同様にして式(1)の化合物を合成した。'H-NMR (CDC13): 6 1.44 (t, J=8Hz, 3H), 3.18 (q
, J=8) 1z, 2H), 3.54(d-d-t, J=
27Hz, J=6Hz, J=5Hz, 2N>, 4.6
2 (d-t, J=49HzJ=5Hz, 2H), 5.2
6 (broad t, J=6Hz.IH) Examples 3-4
4 (Compounds 3 to 44) Compounds of formula (1) were synthesized in the same manner.
この結果を第1〜2表に示した。The results are shown in Tables 1 and 2.
本発明の殺虫、殺ダニ剤は、前記含フツ素スルホンアミ
ド誘導体を有効成分として含有し、本誘導体のみまたは
これに各1)補助荊、例えば希釈剤、溶剤、界面活性剤
等を配合して、乳剤、水和剤、粉剤、微粒側または粒剤
等に製剤化してなる。希釈剤の例としては、クレー、タ
ルク、ベントナイト、珪藻土、ホワイトカーボン等が挙
げられる。The insecticide and acaricide of the present invention contains the above-mentioned fluorine-containing sulfonamide derivative as an active ingredient, and the present derivative alone or in combination with each of 1) auxiliary substances such as a diluent, a solvent, a surfactant, etc. It is formulated into emulsions, wettable powders, powders, fine grains, granules, etc. Examples of diluents include clay, talc, bentonite, diatomaceous earth, white carbon, and the like.
溶剤の例としては、シクロヘキサノン、キシ1/ン、ト
ルエン、メチルエチルケトン、2−プロパツール、メチ
ルナフタレン、ジメチルナフタレン等が挙げられる。界
面活性剤の例としては、アルキルベンゼンスルホン酸金
属塩、ポリオキシエチレンアルキルアリールエーテル、
アルキル硫酸ナトリウム、ジナフチルメタンジスルホン
酸金属塩、アルキルナフタレンスルホン酸金属塩、リグ
ニンスルホン酸金属塩等が挙げられる。その他の補助剤
としては、カルボキシメチルセルロース、ポリエチレン
グリコール、アラビアゴム等が挙げられる。Examples of the solvent include cyclohexanone, xy1/one, toluene, methyl ethyl ketone, 2-propanol, methylnaphthalene, dimethylnaphthalene, and the like. Examples of surfactants include alkylbenzene sulfonic acid metal salts, polyoxyethylene alkylaryl ethers,
Examples include sodium alkyl sulfate, dinaphthylmethane disulfonic acid metal salt, alkylnaphthalene sulfonic acid metal salt, and lignin sulfonic acid metal salt. Other adjuvants include carboxymethyl cellulose, polyethylene glycol, gum arabic, and the like.
有効成分の配合割合については、必要に応じ適宜選ばれ
るが、粉剤または粒剤とする場合は、0゜1−・−20
%(ill)、乳剤または永和薊とする場合は、5−8
0%(重量)が適当である。The blending ratio of the active ingredients is selected as necessary, but when making powders or granules, it is 0°1-・-20.
% (ill), 5-8 when using emulsion or Eiwaji
0% (by weight) is appropriate.
使用に際しては、過当な濃度に希釈して散布するかまた
は直接施用する。When using it, either spray it diluted to an appropriate concentration or apply it directly.
本発明の殺虫、殺ダニ剤は、茎葉散布、土壌施用、育苗
箱施用または水面施用等により使用することができる。The insecticide and acaricide of the present invention can be used by spraying on foliage, soil, seedling box, water surface, etc.
その施用量は、使用される化合物の種類、対象害虫、発
生傾向、被害の程度、環境条件、使用する剤型等によっ
てかわるが、粉剤および粒剤のようにそのまま使用する
場合は、有効成分として10アール当り0.1g〜IK
g、好ましくは1g〜300 gの範囲から適宜に選ぶ
のがよい。The amount of application varies depending on the type of compound used, the target pest, the tendency of occurrence, the degree of damage, environmental conditions, the dosage form used, etc. 0.1g~IK per 10 ares
g, preferably selected from the range of 1 g to 300 g.
また乳剤および水和剤とする場合のように液状で使用す
る場合は、0.1〜1.000 p p m、好ましく
は10〜500 p p mの範囲から適宜に選ぶのが
よい。When used in liquid form, such as in the case of emulsions and wettable powders, the content should be appropriately selected from the range of 0.1 to 1.000 ppm, preferably 10 to 500 ppm.
本発明の殺虫、殺ダニ剤は、他の殺虫剤、殺菌剤を混合
して使用することもできる。The insecticide and acaricide of the present invention can also be used in combination with other insecticides and fungicides.
次に本発明の殺虫、殺ダニ剤の実施例を挙げて、具体的
に説明する。以下実施例中の%は、重量百分率を示す。Next, examples of the insecticide and acaricide of the present invention will be specifically explained. % in the following examples indicates weight percentage.
実施例45(乳剤)
化合物(1) 30%、シクロへキザノン20%、ポリ
オキシエチレンアルキルアリールエーテル1)%、アル
キルベンゼンスルホン酸カルシウム4%およびメチルナ
フタリン35%を均一に溶解して乳剤とした。Example 45 (Emulsion) 30% of Compound (1), 20% of cyclohexanone, 1% of polyoxyethylene alkylaryl ether, 4% of calcium alkylbenzenesulfonate and 35% of methylnaphthalene were uniformly dissolved to prepare an emulsion.
実施N46(水和剤)
化合物(14) 40%、珪藻±15%、クレー15%
、ホワイトカーボン25%、ジナフチルメタンジスルホ
ン酸ナトリウム2%およびリグニンスルホン酸ナトリウ
ム3%を均一に混合粉砕して水和剤とした。Implementation N46 (hydrating powder) Compound (14) 40%, diatom ±15%, clay 15%
, 25% of white carbon, 2% of sodium dinaphthylmethane disulfonate, and 3% of sodium ligninsulfonate were uniformly mixed and pulverized to prepare a wettable powder.
実施例47(粉剤)
化合物(28)2%、珪藻±5%およびクレー93%を
均一に混合粉砕して粉剤とした。Example 47 (Powder) 2% of compound (28), ±5% of diatoms, and 93% of clay were uniformly mixed and ground to obtain a powder.
実施例48(粒剤)
化合物(33) 5%、ラウリルアルコール硫酸エステ
ルのナトリウム塩2%、リグニンスルホン酸ナトリウム
5%、カルボキシメチルセルロース2%およびクレー8
6%を均一に混合粉砕する。この混合物100重量部に
水20重量部を加えて練合し、押出式造粒機を用いて1
4〜32メツシエの粒状に加工したのち、乾燥して粒剤
とした。Example 48 (granules) Compound (33) 5%, sodium salt of lauryl alcohol sulfate 2%, sodium lignin sulfonate 5%, carboxymethyl cellulose 2% and clay 8
Mix and grind 6% uniformly. Add 20 parts by weight of water to 100 parts by weight of this mixture, knead it, and use an extrusion type granulator to
After processing into granules of 4 to 32 mesh sizes, they were dried to form granules.
次に本発明の殺虫、殺ダニ剤の奏する効果を試験例をも
って説明する。Next, the effects of the insecticide and acaricide of the present invention will be explained using test examples.
試験例1
ミハ ニに る
10dのポットに植えた大豆の1葉期にナミハダニを接
種し、2日後に供試化合物のlO%水和躬の10100
pp液を20献ボットに潅注し、処理3,14日後のナ
ミハダニを数え防除効率を求めたいこの結果を第3表に
示した。Test Example 1 Soybeans planted in 10 d pots were inoculated with two-spotted spider mites at the first-leaf stage, and two days later, 10,100 % of the test compound was inoculated with 10% hydration of the test compound.
The pp solution was irrigated into 20 pots, and the number of two-spotted spider mites was counted 3 and 14 days after treatment to determine the control efficiency.The results are shown in Table 3.
第3麦
試験例2
1 アブ−ムシにまl慕l
角形ロックウールに植えられたキュウリ苗にワタアブラ
ムシ雌成虫を接種し、20〜301)J[産任させた後
、成虫を取り除いた。供試化合物10%水和剤の4pp
m溶液5−をロックウールに潅注し、3日後の死虫率を
求めた。この結果を第4表に示した。Third wheat test example 2 1 Infestation with aphids Cucumber seedlings planted in square rock wool were inoculated with female cotton aphids, and after giving birth, the adults were removed. 4pp of test compound 10% hydrating agent
M solution 5- was sprinkled on rock wool, and the mortality rate of insects after 3 days was determined. The results are shown in Table 4.
−一−−−−,j
第4表
第5表
試験例3
二ljロζ対ti、鼾逮」1)
供試化合物に10%永和剤の500 p p m溶液に
キャベツ葉を浸漬し、風乾後に60ccの塩化ビニール
製カップに入れ、そこにコナガ3令幼虫を10頭放ぢ3
日後に死虫率を求めた。この結果を第5表に示した。-1----,j Table 4 Table 5 Test Example 3 2 lj ro ζ vs ti, snoring'' 1) Cabbage leaves were immersed in a 500 ppm solution of a 10% permanent agent in the test compound, After air drying, place in a 60cc vinyl chloride cup and release 10 3rd instar diamondback moth larvae into it.
Mortality rate was determined after 1 day. The results are shown in Table 5.
[発明の効果]
本発明の含フツ素スルホンアミド誘導体は、農園芸上有
害なこん虫類、例えば、アブラムシ、コナガ、ニカメイ
チユウ、ミナミキイロアザミウマ、トビイロウンカ、セ
ジ日ウンカおよびツマグロココバイ等のウンカ、3コバ
イ類等、またハダニ類、例えば、ミカンハダニ、ナミハ
ダニ、リンゴハダニ、カンザワハダニ等に対して極めて
優れた殺虫活性を有するとともに、極めて優れた浸透性
殺虫活性を有する。さらにカメムシ類等の半翅目、ハス
モンヨトウ等の鱗翅目、イエバエ、アカイエカ等の双翅
目、アズキゾウムシ、コガネムシ類等の鞘翅目、チャバ
ネゴキブリ等の直翅目害虫の防除にも有効である。[Effects of the Invention] The fluorine-containing sulfonamide derivative of the present invention is effective against insects that are harmful to agriculture and horticulture, such as aphids, diamondback moths, Japanese planthoppers, southern yellow thrips, brown planthoppers, Japanese planthoppers, and planthoppers such as the black-bottomed planthopper, It has extremely excellent insecticidal activity against 3 types of insects, spider mites, such as orange spider mite, two-spotted spider mite, apple spider mite, and Kanzawa spider mite, as well as extremely excellent systemic insecticidal activity. Furthermore, it is also effective in controlling Hemiptera such as stink bugs, Lepidoptera such as Spodoptera, Diptera such as the house fly and Culex mosquito, Coleoptera such as the bean weevil and scarab beetles, and Orthoptera such as the German cockroach.
Claims (2)
、RはC_1〜C_4のアルキル基、ハロアルキル基、
シクロアルキル基、ナフチル基、ベンジル基、ピリジル
基、チエニル基および式▲数式、化学式、表等がありま
す▼(ここでXは水素、C_1〜C_4のアルキル基、
ハロアルキル基、アルコキシ基、ニトロ基、置換アミノ
基およびシアノ基を示し、mは1〜2を示す。)を示す
。]にて示される含フッ素スルホンアミド誘導体。(1) General formula R-SO_2-NHCH_2CH_2F (I) [wherein R is an alkyl group of C_1 to C_4, a haloalkyl group,
Cycloalkyl groups, naphthyl groups, benzyl groups, pyridyl groups, thienyl groups and formulas ▲ Numerical formulas, chemical formulas, tables, etc. ▼ (where X is hydrogen, C_1 to C_4 alkyl groups,
It represents a haloalkyl group, an alkoxy group, a nitro group, a substituted amino group and a cyano group, and m represents 1-2. ) is shown. ] A fluorine-containing sulfonamide derivative represented by.
、RはC_1〜C_4のアルキル基、ハロアルキル基、
シクロアルキル基、ナフチル基、ベンジル基、ピリジル
基、チエニル基および式▲数式、化学式、表等がありま
す▼(ここでXは水素、C_1〜C_4のアルキル基、
ハロアルキル基、アルコキシ基、ニトロ基、置換アミノ
基およびシアノ基を示し、mは1〜2を示す。)を示す
。]にて示される含フッ素スルホン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殺虫、殺ダニ剤。(2) General formula R-SO_2-NHCH_2CH_2F (I) [wherein R is a C_1 to C_4 alkyl group, a haloalkyl group,
Cycloalkyl groups, naphthyl groups, benzyl groups, pyridyl groups, thienyl groups and formulas ▲ Numerical formulas, chemical formulas, tables, etc. ▼ (where X is hydrogen, C_1 to C_4 alkyl groups,
It represents a haloalkyl group, an alkoxy group, a nitro group, a substituted amino group and a cyano group, and m represents 1-2. ) is shown. ] An insecticide and acaricide characterized by containing a fluorine-containing sulfonamide derivative shown in the following as an active ingredient.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP21244089A JPH0377861A (en) | 1989-08-18 | 1989-08-18 | Fluorine-containing sulfonamide derivative, insecticide and acaricide |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP21244089A JPH0377861A (en) | 1989-08-18 | 1989-08-18 | Fluorine-containing sulfonamide derivative, insecticide and acaricide |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH0377861A true JPH0377861A (en) | 1991-04-03 |
Family
ID=16622645
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP21244089A Pending JPH0377861A (en) | 1989-08-18 | 1989-08-18 | Fluorine-containing sulfonamide derivative, insecticide and acaricide |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH0377861A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006100271A1 (en) * | 2005-03-24 | 2006-09-28 | Basf Aktiengesellschaft | Sulphonyl compounds for seed treatment |
US8029714B2 (en) | 2005-09-12 | 2011-10-04 | Federal-Mogul World Wide, Inc. | Radial seal and method of making |
-
1989
- 1989-08-18 JP JP21244089A patent/JPH0377861A/en active Pending
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006100271A1 (en) * | 2005-03-24 | 2006-09-28 | Basf Aktiengesellschaft | Sulphonyl compounds for seed treatment |
US8029714B2 (en) | 2005-09-12 | 2011-10-04 | Federal-Mogul World Wide, Inc. | Radial seal and method of making |
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