HU193670B - Insecticides containing derivatives of 2-/nitro-methilene/-/1,3-tiasin/ and process for production those - Google Patents
Insecticides containing derivatives of 2-/nitro-methilene/-/1,3-tiasin/ and process for production those Download PDFInfo
- Publication number
- HU193670B HU193670B HU84598A HU59884A HU193670B HU 193670 B HU193670 B HU 193670B HU 84598 A HU84598 A HU 84598A HU 59884 A HU59884 A HU 59884A HU 193670 B HU193670 B HU 193670B
- Authority
- HU
- Hungary
- Prior art keywords
- alkyl
- formula
- halogen
- optionally substituted
- nitromethylene
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 239000002917 insecticide Substances 0.000 title description 4
- 238000004519 manufacturing process Methods 0.000 title description 2
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 19
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 13
- 150000002367 halogens Chemical group 0.000 claims abstract description 11
- 125000001797 benzyl group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 3
- 239000000203 mixture Substances 0.000 claims description 35
- 150000001875 compounds Chemical class 0.000 claims description 26
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- -1 C2-C10 alkyl Chemical group 0.000 claims description 18
- 125000005843 halogen group Chemical group 0.000 claims description 12
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- 239000007787 solid Substances 0.000 claims description 9
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- 230000000749 insecticidal effect Effects 0.000 claims description 7
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- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
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- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
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- 239000002736 nonionic surfactant Substances 0.000 claims 1
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- 125000005543 phthalimide group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 5
- 230000000361 pesticidal effect Effects 0.000 abstract description 4
- 125000001424 substituent group Chemical group 0.000 abstract description 3
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- 229910052760 oxygen Inorganic materials 0.000 abstract description 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000004438 haloalkoxy group Chemical group 0.000 abstract 2
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- 241000256250 Spodoptera littoralis Species 0.000 description 3
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- 235000012211 aluminium silicate Nutrition 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
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- LCCNCVORNKJIRZ-UHFFFAOYSA-N parathion Chemical compound CCOP(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 LCCNCVORNKJIRZ-UHFFFAOYSA-N 0.000 description 3
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- 239000012141 concentrate Substances 0.000 description 1
- 235000008504 concentrate Nutrition 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000003113 dilution method Methods 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 1
- LRCFXGAMWKDGLA-UHFFFAOYSA-N dioxosilane;hydrate Chemical compound O.O=[Si]=O LRCFXGAMWKDGLA-UHFFFAOYSA-N 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
- 239000006185 dispersion Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910003480 inorganic solid Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 229910052919 magnesium silicate Inorganic materials 0.000 description 1
- 235000019792 magnesium silicate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000000025 natural resin Substances 0.000 description 1
- 229920000847 nonoxynol Polymers 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 150000002897 organic nitrogen compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- NIXKBAZVOQAHGC-UHFFFAOYSA-N phenylmethanesulfonic acid Chemical compound OS(=O)(=O)CC1=CC=CC=C1 NIXKBAZVOQAHGC-UHFFFAOYSA-N 0.000 description 1
- 239000003016 pheromone Substances 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- HDMGAZBPFLDBCX-UHFFFAOYSA-M potassium;sulfooxy sulfate Chemical compound [K+].OS(=O)(=O)OOS([O-])(=O)=O HDMGAZBPFLDBCX-UHFFFAOYSA-M 0.000 description 1
- 235000014483 powder concentrate Nutrition 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 231100000916 relative toxicity Toxicity 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229960004029 silicic acid Drugs 0.000 description 1
- 229960001866 silicon dioxide Drugs 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical class OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000002426 superphosphate Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 238000001665 trituration Methods 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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/86—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/04—1,3-Thiazines; Hydrogenated 1,3-thiazines
- C07D279/06—1,3-Thiazines; Hydrogenated 1,3-thiazines not condensed with other rings
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Environmental Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Health & Medical Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB838304385A GB8304385D0 (en) | 1983-02-17 | 1983-02-17 | Pesticidal nitromethylene derivatives |
| GB838325538A GB8325538D0 (en) | 1983-09-23 | 1983-09-23 | Pesticidal nitromethylene derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU193670B true HU193670B (en) | 1987-11-30 |
Family
ID=26285259
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU84598A HU193670B (en) | 1983-02-17 | 1984-02-15 | Insecticides containing derivatives of 2-/nitro-methilene/-/1,3-tiasin/ and process for production those |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US4529726A (en, 2012) |
| EP (1) | EP0116998B1 (en, 2012) |
| JP (1) | JPH0688988B2 (en, 2012) |
| KR (1) | KR910005707B1 (en, 2012) |
| AR (1) | AR240320A1 (en, 2012) |
| AU (1) | AU563809B2 (en, 2012) |
| BR (1) | BR8400651A (en, 2012) |
| CA (1) | CA1218362A (en, 2012) |
| CS (1) | CS272204B2 (en, 2012) |
| DD (1) | DD215001A5 (en, 2012) |
| DE (1) | DE3467167D1 (en, 2012) |
| DK (1) | DK164502C (en, 2012) |
| ES (1) | ES8507525A1 (en, 2012) |
| FI (1) | FI80684C (en, 2012) |
| GR (1) | GR79544B (en, 2012) |
| HU (1) | HU193670B (en, 2012) |
| IE (1) | IE56817B1 (en, 2012) |
| IL (1) | IL70758A (en, 2012) |
| MX (1) | MX159538A (en, 2012) |
| NO (1) | NO158873C (en, 2012) |
| NZ (1) | NZ207162A (en, 2012) |
| OA (1) | OA07658A (en, 2012) |
| PH (1) | PH20408A (en, 2012) |
| PL (1) | PL146583B1 (en, 2012) |
| PT (1) | PT78103B (en, 2012) |
| ZW (1) | ZW2284A1 (en, 2012) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8323060D0 (en) * | 1983-08-26 | 1983-09-28 | Shell Int Research | Preparing heterocyclic compounds |
| GB8323061D0 (en) * | 1983-08-26 | 1983-09-28 | Shell Int Research | Pesticidal heterocyclic compounds |
| US5972934A (en) * | 1996-07-29 | 1999-10-26 | Novartis Ag | Stabilized nithiazine compositions |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1527643A (en) * | 1975-04-02 | 1978-10-04 | Shell Int Research | Nitromethylene derivatives of tetrahydro-2h-1,3-thiazine |
| US4052388A (en) * | 1976-10-12 | 1977-10-04 | Shell Oil Company | 3-acetyltetrahydro-2-(nitromethylene)-2h-1,3-thiazine |
-
1984
- 1984-01-18 CA CA000445528A patent/CA1218362A/en not_active Expired
- 1984-01-23 IL IL70758A patent/IL70758A/xx not_active IP Right Cessation
- 1984-02-08 DE DE8484200178T patent/DE3467167D1/de not_active Expired
- 1984-02-08 US US06/578,142 patent/US4529726A/en not_active Expired - Fee Related
- 1984-02-08 EP EP84200178A patent/EP0116998B1/en not_active Expired
- 1984-02-15 ES ES529734A patent/ES8507525A1/es not_active Expired
- 1984-02-15 HU HU84598A patent/HU193670B/hu not_active IP Right Cessation
- 1984-02-15 PL PL1984246227A patent/PL146583B1/pl unknown
- 1984-02-15 BR BR8400651A patent/BR8400651A/pt not_active IP Right Cessation
- 1984-02-15 NO NO840559A patent/NO158873C/no unknown
- 1984-02-15 JP JP59025319A patent/JPH0688988B2/ja not_active Expired - Lifetime
- 1984-02-15 MX MX8238A patent/MX159538A/es unknown
- 1984-02-15 FI FI840607A patent/FI80684C/fi not_active IP Right Cessation
- 1984-02-15 DD DD84260095A patent/DD215001A5/de not_active IP Right Cessation
- 1984-02-15 NZ NZ207162A patent/NZ207162A/en unknown
- 1984-02-15 DK DK070984A patent/DK164502C/da not_active IP Right Cessation
- 1984-02-15 KR KR1019840000704A patent/KR910005707B1/ko not_active Expired
- 1984-02-15 CS CS841070A patent/CS272204B2/cs unknown
- 1984-02-15 OA OA58231A patent/OA07658A/xx unknown
- 1984-02-15 AU AU24610/84A patent/AU563809B2/en not_active Ceased
- 1984-02-15 GR GR73807A patent/GR79544B/el unknown
- 1984-02-15 ZW ZW22/84A patent/ZW2284A1/xx unknown
- 1984-02-15 AR AR295722A patent/AR240320A1/es active
- 1984-02-15 IE IE343/84A patent/IE56817B1/en not_active IP Right Cessation
- 1984-02-15 PT PT78103A patent/PT78103B/pt not_active IP Right Cessation
- 1984-02-15 PH PH30247A patent/PH20408A/en unknown
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |