CS272204B2 - Insecticide and method of its active substance production - Google Patents
Insecticide and method of its active substance production Download PDFInfo
- Publication number
- CS272204B2 CS272204B2 CS841070A CS107084A CS272204B2 CS 272204 B2 CS272204 B2 CS 272204B2 CS 841070 A CS841070 A CS 841070A CS 107084 A CS107084 A CS 107084A CS 272204 B2 CS272204 B2 CS 272204B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- optionally substituted
- formula
- compound
- alkyl
- halogen
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 13
- 239000002917 insecticide Substances 0.000 title description 8
- 238000004519 manufacturing process Methods 0.000 title description 6
- 239000013543 active substance Substances 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 21
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 12
- 125000001797 benzyl group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 9
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 7
- 125000005544 phthalimido group Chemical group 0.000 claims abstract description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 45
- 239000000203 mixture Substances 0.000 claims description 37
- 239000004480 active ingredient Substances 0.000 claims description 17
- 230000000749 insecticidal effect Effects 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
- 125000006277 halobenzyl group Chemical group 0.000 claims description 4
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 150000002367 halogens Chemical group 0.000 abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 10
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- 125000003545 alkoxy group Chemical group 0.000 abstract description 4
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- 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
- 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
- 239000004615 ingredient Substances 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
- 150000002576 ketones Chemical class 0.000 description 1
- 230000001418 larval effect Effects 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 235000012243 magnesium silicates Nutrition 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 239000000025 natural resin Substances 0.000 description 1
- 235000016709 nutrition Nutrition 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
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 238000004525 petroleum distillation Methods 0.000 description 1
- 239000003016 pheromone Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 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
- 238000004062 sedimentation Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 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
- 235000020354 squash Nutrition 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 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
- 239000000725 suspension Substances 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
- 239000013008 thixotropic agent Substances 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 238000001665 trituration Methods 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
- 239000000080 wetting agent 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 (2)
| Publication Number | Publication Date |
|---|---|
| CS107084A2 CS107084A2 (en) | 1990-03-14 |
| CS272204B2 true CS272204B2 (en) | 1991-01-15 |
Family
ID=26285259
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS841070A CS272204B2 (en) | 1983-02-17 | 1984-02-15 | Insecticide and method of its active substance production |
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
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