JPS60218386A - ニトロメチレン誘導体、その製法及び殺虫剤 - Google Patents
ニトロメチレン誘導体、その製法及び殺虫剤Info
- Publication number
- JPS60218386A JPS60218386A JP7296684A JP7296684A JPS60218386A JP S60218386 A JPS60218386 A JP S60218386A JP 7296684 A JP7296684 A JP 7296684A JP 7296684 A JP7296684 A JP 7296684A JP S60218386 A JPS60218386 A JP S60218386A
- Authority
- JP
- Japan
- Prior art keywords
- general formula
- formula
- compound
- lower alkyl
- chloro
- 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.)
- Granted
Links
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- -1 Nitromethylene Chemical class 0.000 title claims description 45
- 238000002360 preparation method Methods 0.000 title abstract description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 81
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 20
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 6
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 5
- 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
- OTPDWCMLUKMQNO-UHFFFAOYSA-N 1,2,3,4-tetrahydropyrimidine Chemical compound C1NCC=CN1 OTPDWCMLUKMQNO-UHFFFAOYSA-N 0.000 claims abstract 2
- 238000004519 manufacturing process Methods 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 9
- 239000004480 active ingredient Substances 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 3
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- 241000196324 Embryophyta Species 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
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- 241000256593 Brachycaudus schwartzi Species 0.000 description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 3
- 229940126062 Compound A Drugs 0.000 description 3
- 241000258937 Hemiptera Species 0.000 description 3
- 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 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
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- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
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- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
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- UMNKXPULIDJLSU-UHFFFAOYSA-N dichlorofluoromethane Chemical compound FC(Cl)Cl UMNKXPULIDJLSU-UHFFFAOYSA-N 0.000 description 1
- 229940099364 dichlorofluoromethane Drugs 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
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- 239000012895 dilution Substances 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
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- 125000004119 disulfanediyl group Chemical group *SS* 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
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- 230000008451 emotion Effects 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 238000003958 fumigation Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
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- 150000002334 glycols Chemical class 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 244000000013 helminth Species 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 235000012907 honey Nutrition 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- GNYKPRZVSYJFIV-UHFFFAOYSA-N imidazolidin-1-ium;chloride Chemical compound Cl.C1CNCN1 GNYKPRZVSYJFIV-UHFFFAOYSA-N 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 229910052622 kaolinite Inorganic materials 0.000 description 1
- CYPPCCJJKNISFK-UHFFFAOYSA-J kaolinite Chemical compound [OH-].[OH-].[OH-].[OH-].[Al+3].[Al+3].[O-][Si](=O)O[Si]([O-])=O CYPPCCJJKNISFK-UHFFFAOYSA-J 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
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- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
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- 238000002156 mixing Methods 0.000 description 1
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- ZRTFUNNRUQYKHQ-UHFFFAOYSA-N n'-[(6-chloropyridin-3-yl)methyl]butane-1,4-diamine Chemical compound NCCCCNCC1=CC=C(Cl)N=C1 ZRTFUNNRUQYKHQ-UHFFFAOYSA-N 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 229960003966 nicotinamide Drugs 0.000 description 1
- 235000005152 nicotinamide Nutrition 0.000 description 1
- 239000011570 nicotinamide Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000002898 organic sulfur compounds Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000010451 perlite Substances 0.000 description 1
- 235000019362 perlite Nutrition 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000008054 sulfonate salts Chemical class 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Landscapes
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
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. |
| DE8585104254T DE3571131D1 (en) | 1984-04-13 | 1985-04-09 | Nitromethylene derivatives, intermediates, and process for their preparation as insecticides |
| EP85104254A EP0163855B1 (de) | 1984-04-13 | 1985-04-09 | Nitromethylen-Derivate, Zwischenprodukte für diese, Verfahren zu ihrer Herstellung sowie Insektizide |
| 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 |
| CA000478814A CA1262725A (en) | 1984-04-13 | 1985-04-11 | Nitromethylene derivatives, intermediates thereof, processes for production thereof, and insecticides |
| TR22165A TR22165A (tr) | 1984-04-13 | 1985-04-11 | Nitrometilen tuerevleri,bunlar icin ara ueruenler bunlarin ueretimi icin usueller ve ensektisidler |
| DD85275098A DD236445A5 (de) | 1984-04-13 | 1985-04-11 | Insektizide mittel |
| ES542202A ES542202A0 (es) | 1984-04-13 | 1985-04-12 | Procedimiento para la obtencion de un derivado de nitrometi-leno |
| ZA852742A ZA852742B (en) | 1984-04-13 | 1985-04-12 | Nitromethylene derivatives intermediates thereof,processes for production thereof,and insecticides |
| 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. |
| KR1019850002454A KR910004433B1 (ko) | 1984-04-13 | 1985-04-12 | 니트로메틸렌 유도체의 제조방법 |
| AU41097/85A AU571961B2 (en) | 1984-04-13 | 1985-04-12 | Pyridine derivatives |
| HU851372A HU196029B (en) | 1984-04-13 | 1985-04-12 | Insecticides comprising nitro-methylene derivatives as active ingredient and process for producing nitro-methylene derivatives |
| 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 |
| 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 |
| OA58567A OA07991A (fr) | 1984-04-13 | 1985-04-12 | Dérivés de nitrométhylène, produits intermédiaires correspondants, leur procédé de production et insecticides contenant ces dérivés. |
| 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 |
|---|---|
| JPS60218386A true JPS60218386A (ja) | 1985-11-01 |
| JPH0460114B2 JPH0460114B2 (enrdf_load_stackoverflow) | 1992-09-25 |
Family
ID=13504629
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| 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 (enrdf_load_stackoverflow) |
| DD (1) | DD236445A5 (enrdf_load_stackoverflow) |
| ZA (1) | ZA852742B (enrdf_load_stackoverflow) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993004032A1 (en) * | 1991-08-22 | 1993-03-04 | Nippon Soda Co., Ltd. | Novel amine derivative, production thereof, and insecticide |
| US5298507A (en) * | 1985-02-04 | 1994-03-29 | Nihon Bayer Agrochem K.K. | Heterocyclic compounds |
| WO1995007259A1 (fr) * | 1992-03-10 | 1995-03-16 | Nippon Soda Co., Ltd. | Derive de pyridine et son procede de fabrication |
| JPH09511978A (ja) * | 1994-04-14 | 1997-12-02 | バイエル・アクチエンゲゼルシヤフト | 殺虫性肥料混合物 |
-
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
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5298507A (en) * | 1985-02-04 | 1994-03-29 | Nihon Bayer Agrochem K.K. | Heterocyclic compounds |
| US6022967A (en) * | 1985-02-04 | 2000-02-08 | Nihon Bayer Agrochem K.K. | Heterocyclic compounds |
| US6297374B1 (en) | 1985-02-04 | 2001-10-02 | Nihon Bayer Agrochem K.K. | Nitroimino-nitromethylene—azole or-azine heterocyclic compounds, insecticidal compositions containing them, and insecticidal methods of using them |
| WO1993004032A1 (en) * | 1991-08-22 | 1993-03-04 | Nippon Soda Co., Ltd. | Novel amine derivative, production thereof, and insecticide |
| WO1995007259A1 (fr) * | 1992-03-10 | 1995-03-16 | Nippon Soda Co., Ltd. | Derive de pyridine et son procede de fabrication |
| JPH09511978A (ja) * | 1994-04-14 | 1997-12-02 | バイエル・アクチエンゲゼルシヤフト | 殺虫性肥料混合物 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0460114B2 (enrdf_load_stackoverflow) | 1992-09-25 |
| DD236445A5 (de) | 1986-06-11 |
| ZA852742B (en) | 1985-12-24 |
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