JPH0460114B2 - - Google Patents
Info
- Publication number
- JPH0460114B2 JPH0460114B2 JP7296684A JP7296684A JPH0460114B2 JP H0460114 B2 JPH0460114 B2 JP H0460114B2 JP 7296684 A JP7296684 A JP 7296684A JP 7296684 A JP7296684 A JP 7296684A JP H0460114 B2 JPH0460114 B2 JP H0460114B2
- Authority
- JP
- Japan
- Prior art keywords
- general formula
- formula
- compound
- chloro
- nitromethylene
- 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.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 claims description 71
- -1 nitromethylene Chemical class 0.000 claims description 39
- 238000004519 manufacturing process Methods 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 239000002917 insecticide Substances 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- GOBRRFQNYBGHAU-UHFFFAOYSA-N 2-(nitromethylidene)-1,3-diazinane Chemical compound [O-][N+](=O)C=C1NCCCN1 GOBRRFQNYBGHAU-UHFFFAOYSA-N 0.000 claims description 3
- OHXNZFJZRFHBLX-UHFFFAOYSA-N 2-(nitromethylidene)imidazolidine Chemical compound [O-][N+](=O)C=C1NCCN1 OHXNZFJZRFHBLX-UHFFFAOYSA-N 0.000 claims description 3
- 238000000034 method Methods 0.000 description 28
- 241000607479 Yersinia pestis Species 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 241000238631 Hexapoda Species 0.000 description 16
- 239000003795 chemical substances by application Substances 0.000 description 16
- 239000000203 mixture Substances 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 239000004480 active ingredient Substances 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
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 239000003085 diluting agent Substances 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 238000005507 spraying Methods 0.000 description 6
- 239000003381 stabilizer Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 230000000749 insecticidal effect Effects 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 241001414720 Cicadellidae Species 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
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- 241000258937 Hemiptera Species 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- 239000004372 Polyvinyl alcohol Substances 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 239000011574 phosphorus Substances 0.000 description 4
- 229920002451 polyvinyl alcohol Polymers 0.000 description 4
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 4
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 241001556089 Nilaparvata lugens Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
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- 239000003905 agrochemical Substances 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- HKSZSGAPTPXYTI-UHFFFAOYSA-N n'-[(6-chloropyridin-3-yl)methyl]ethane-1,2-diamine Chemical compound NCCNCC1=CC=C(Cl)N=C1 HKSZSGAPTPXYTI-UHFFFAOYSA-N 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- SKCNYHLTRZIINA-UHFFFAOYSA-N 2-chloro-5-(chloromethyl)pyridine Chemical compound ClCC1=CC=C(Cl)N=C1 SKCNYHLTRZIINA-UHFFFAOYSA-N 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- 241001124076 Aphididae Species 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 2
- 241001327638 Cimex lectularius Species 0.000 description 2
- 241000490513 Ctenocephalides canis Species 0.000 description 2
- 239000004606 Fillers/Extenders Substances 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 241001466042 Fulgoromorpha Species 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- 241000721703 Lymantria dispar Species 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 241000500437 Plutella xylostella Species 0.000 description 2
- 244000061458 Solanum melongena Species 0.000 description 2
- 235000002597 Solanum melongena Nutrition 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 229940072049 amyl acetate Drugs 0.000 description 2
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 2
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- 125000003118 aryl group Chemical group 0.000 description 2
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- 239000003638 chemical reducing agent Substances 0.000 description 2
- 239000002734 clay mineral Substances 0.000 description 2
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 2
- 238000010410 dusting Methods 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000003701 inert diluent Substances 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
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- HTFHALGFLUWNGS-UHFFFAOYSA-N n'-[(6-chloropyridin-3-yl)methyl]propane-1,3-diamine Chemical compound NCCCNCC1=CC=C(Cl)N=C1 HTFHALGFLUWNGS-UHFFFAOYSA-N 0.000 description 2
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- WWYNJERNGUHSAO-XUDSTZEESA-N (+)-Norgestrel Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](CC)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 WWYNJERNGUHSAO-XUDSTZEESA-N 0.000 description 1
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- AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 description 1
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- Pyridine Compounds (AREA)
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Priority Applications (26)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP7296684A JPS60218386A (ja) | 1984-04-13 | 1984-04-13 | ニトロメチレン誘導体、その製法及び殺虫剤 |
ZW50/85A ZW5085A1 (en) | 1984-04-13 | 1985-03-21 | Nitromethylene derivatives,intermediates thereof,processes for production thereof,and insecticides |
PH32074A PH22486A (en) | 1984-04-13 | 1985-03-29 | Nitromethylene derivatives, intermediante thereof, process for production thereof |
PT80231A PT80231B (pt) | 1984-04-13 | 1985-04-03 | Processo para a preparacao de derivados de nitrometileno com efeito insecticida |
US06/720,838 US4678795A (en) | 1984-04-13 | 1985-04-08 | 1-pyridylmethyl-2-nitromethylene-1,3-diazacycloalkane insecticides |
AT85104254T ATE44145T1 (de) | 1984-04-13 | 1985-04-09 | Nitromethylen-derivate, zwischenprodukte fuer diese, verfahren zu ihrer herstellung sowie insektizide. |
EP85104254A EP0163855B1 (de) | 1984-04-13 | 1985-04-09 | Nitromethylen-Derivate, Zwischenprodukte für diese, Verfahren zu ihrer Herstellung sowie Insektizide |
DE8585104254T DE3571131D1 (en) | 1984-04-13 | 1985-04-09 | Nitromethylene derivatives, intermediates, and process for their preparation as insecticides |
NZ211738A NZ211738A (en) | 1984-04-13 | 1985-04-10 | Heterocyclic nitromethylene derivatives and insecticidal compositions |
IL74864A IL74864A (en) | 1984-04-13 | 1985-04-10 | 1-pyridylalkyl-2-nitromethylene-1,3,-diaza cycloalkanes,their production and insecticidal compositions containing them |
DD85275098A DD236445A5 (de) | 1984-04-13 | 1985-04-11 | Insektizide mittel |
TR22165A TR22165A (tr) | 1984-04-13 | 1985-04-11 | Nitrometilen tuerevleri,bunlar icin ara ueruenler bunlarin ueretimi icin usueller ve ensektisidler |
CA000478814A CA1262725A (en) | 1984-04-13 | 1985-04-11 | Nitromethylene derivatives, intermediates thereof, processes for production thereof, and insecticides |
DK167885A DK169072B1 (da) | 1984-04-13 | 1985-04-12 | 1-Pyridylalkylsubstitueret imidazolidinyl-2- eller hexahydropyrimidinyl-2-nitromethylenderivat og salte deraf, fremgangsmåde til dets fremstilling, insekticider indeholdende det samt dets anvendelse til insektbekæmpelse, og fremgangsmåde til fremstilling af insekticider indeholdende det |
HU851372A HU196029B (en) | 1984-04-13 | 1985-04-12 | Insecticides comprising nitro-methylene derivatives as active ingredient and process for producing nitro-methylene derivatives |
AR85300060A AR241909A1 (es) | 1984-04-13 | 1985-04-12 | 1-n-piridilalquil-2-(nitrometilen)-imidazolidinas y tetrahidropirimidinas substituidas, procedimiento para su preparacion, intermediarios, composiciones insecticidas que los contienen. |
ES542202A ES8603242A1 (es) | 1984-04-13 | 1985-04-12 | Procedimiento para la obtencion de un derivado de nitrometi-leno |
BR8501739A BR8501739A (pt) | 1984-04-13 | 1985-04-12 | Processo para a preparacao de um derivado de nitrometileno,composicao inseticida,processo para a preparacao de um composto,processos para o combate de insetos e para a preparacao de composicoes |
KR1019850002454A KR910004433B1 (ko) | 1984-04-13 | 1985-04-12 | 니트로메틸렌 유도체의 제조방법 |
ZA852742A ZA852742B (en) | 1984-04-13 | 1985-04-12 | Nitromethylene derivatives intermediates thereof,processes for production thereof,and insecticides |
OA58567A OA07991A (fr) | 1984-04-13 | 1985-04-12 | Dérivés de nitrométhylène, produits intermédiaires correspondants, leur procédé de production et insecticides contenant ces dérivés. |
AU41097/85A AU571961B2 (en) | 1984-04-13 | 1985-04-12 | Pyridine derivatives |
US07/029,303 US4774247A (en) | 1984-04-13 | 1987-03-23 | Nitromethylene derivative insecticides |
US07/130,697 US4812571A (en) | 1984-04-13 | 1987-12-09 | N-(substituted pyridyl-alkyl) alkylenediamine intermediates for insecticides |
AU10183/88A AU597772B2 (en) | 1984-04-13 | 1988-01-11 | Novel pyridine derivatives and processes for their production |
DK198891A DK171643B1 (da) | 1984-04-13 | 1991-12-10 | Pyridylalkylsubstituerede ethylen- og propylendiaminer og fremgangsmåde til deres fremstilling |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP7296684A JPS60218386A (ja) | 1984-04-13 | 1984-04-13 | ニトロメチレン誘導体、その製法及び殺虫剤 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP8741991A Division JPH04217957A (ja) | 1991-03-28 | 1991-03-28 | 新規ジアミン類及びその製法 |
Publications (2)
Publication Number | Publication Date |
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JPS60218386A JPS60218386A (ja) | 1985-11-01 |
JPH0460114B2 true JPH0460114B2 (zh) | 1992-09-25 |
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ID=13504629
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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JP7296684A Granted JPS60218386A (ja) | 1984-04-13 | 1984-04-13 | ニトロメチレン誘導体、その製法及び殺虫剤 |
Country Status (3)
Country | Link |
---|---|
JP (1) | JPS60218386A (zh) |
DD (1) | DD236445A5 (zh) |
ZA (1) | ZA852742B (zh) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ATE67493T1 (de) * | 1985-02-04 | 1991-10-15 | Bayer Agrochem Kk | Heterocyclische verbindungen. |
JPH05310650A (ja) * | 1991-08-22 | 1993-11-22 | Nippon Soda Co Ltd | 新規なアミン誘導体、その製造方法及び殺虫剤 |
JPH05255252A (ja) * | 1992-03-10 | 1993-10-05 | Nippon Soda Co Ltd | ピリジン誘導体およびその製造法 |
DE4412833A1 (de) * | 1994-04-14 | 1995-10-19 | Bayer Ag | Insektizide Düngemischungen |
-
1984
- 1984-04-13 JP JP7296684A patent/JPS60218386A/ja active Granted
-
1985
- 1985-04-11 DD DD85275098A patent/DD236445A5/de unknown
- 1985-04-12 ZA ZA852742A patent/ZA852742B/xx unknown
Also Published As
Publication number | Publication date |
---|---|
DD236445A5 (de) | 1986-06-11 |
ZA852742B (en) | 1985-12-24 |
JPS60218386A (ja) | 1985-11-01 |
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