IE42138B1 - Tetrahydropyridine carboxylic acid esters and salts thereof,and their use as insecticidal and acaricidal agents - Google Patents

Tetrahydropyridine carboxylic acid esters and salts thereof,and their use as insecticidal and acaricidal agents

Info

Publication number: IE42138B1
Authority: IE; Ireland
Prior art keywords: compound; formula; reacted; diluent; compounds
Prior art date: 1974-11-14

Application number

IE2473/75A

Other languages

English (en)

Other versions

IE42138L (en

Original Assignee

Bayer Ag

Priority date (The priority date 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 date listed.)

1974-11-14

Filing date

1975-11-13

Publication date

1980-06-04

1975-11-13 Application filed by Bayer Ag filed Critical Bayer Ag

1976-05-14 Publication of IE42138L publication Critical patent/IE42138L/xx

1980-06-04 Publication of IE42138B1 publication Critical patent/IE42138B1/en

Links

230000000749 insecticidal effect Effects 0.000 title claims abstract description 16
150000003839 salts Chemical class 0.000 title claims abstract description 15
239000003795 chemical substances by application Substances 0.000 title claims abstract description 10
230000000895 acaricidal effect Effects 0.000 title claims description 10
BCVBBQMUAAFVJC-UHFFFAOYSA-N 1,2,3,4-tetrahydropyridin-1-ium-2-carboxylate Chemical class OC(=O)C1CCC=CN1 BCVBBQMUAAFVJC-UHFFFAOYSA-N 0.000 title abstract description 5
150000001875 compounds Chemical class 0.000 claims abstract description 79
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 13
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims abstract description 9
239000012279 sodium borohydride Substances 0.000 claims abstract description 5
229910000033 sodium borohydride Inorganic materials 0.000 claims abstract description 5
150000007530 organic bases Chemical class 0.000 claims abstract description 4
150000001450 anions Chemical class 0.000 claims abstract description 3
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
229910052736 halogen Inorganic materials 0.000 claims abstract description 3
150000002367 halogens Chemical class 0.000 claims abstract description 3
150000007529 inorganic bases Chemical class 0.000 claims abstract description 3
150000007522 mineralic acids Chemical class 0.000 claims abstract description 3
150000007524 organic acids Chemical class 0.000 claims abstract description 3
238000000034 method Methods 0.000 claims description 33
239000000203 mixture Substances 0.000 claims description 29
-1 pyridinium compound Chemical class 0.000 claims description 20
239000003085 diluting agent Substances 0.000 claims description 18
241000607479 Yersinia pestis Species 0.000 claims description 16
238000006243 chemical reaction Methods 0.000 claims description 15
239000004480 active ingredient Substances 0.000 claims description 11
241000238631 Hexapoda Species 0.000 claims description 10
239000002253 acid Substances 0.000 claims description 8
150000002148 esters Chemical class 0.000 claims description 7
239000007788 liquid Substances 0.000 claims description 7
239000002904 solvent Substances 0.000 claims description 6
DNJFTXKSFAMXQF-UHFFFAOYSA-N Arecaidine Chemical compound CN1CCC=C(C(O)=O)C1 DNJFTXKSFAMXQF-UHFFFAOYSA-N 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 4
239000007787 solid Substances 0.000 claims description 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
UNARQANIGOBIHM-UHFFFAOYSA-N Homoarecoline Chemical compound CCOC(=O)C1=CCCN(C)C1 UNARQANIGOBIHM-UHFFFAOYSA-N 0.000 claims description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
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125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 claims description 2
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125000000217 alkyl group Chemical group 0.000 claims description 2
125000000304 alkynyl group Chemical group 0.000 claims description 2
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
125000004494 ethyl ester group Chemical group 0.000 claims description 2
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239000004094 surface-active agent Substances 0.000 claims description 2
125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
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150000003840 hydrochlorides Chemical class 0.000 abstract description 2
125000006528 (C2-C6) alkyl group Chemical group 0.000 abstract 1
125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 1
125000003601 C2-C6 alkynyl group Chemical group 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
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VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
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HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
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239000004606 Fillers/Extenders Substances 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
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UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
GGNLTHFTYNDYNK-UHFFFAOYSA-N Phenkapton Chemical compound CCOP(=S)(OCC)SCSC1=CC(Cl)=CC=C1Cl GGNLTHFTYNDYNK-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
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PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000000642 acaricide Substances 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
125000005037 alkyl phenyl group Chemical group 0.000 description 2
235000012211 aluminium silicate Nutrition 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
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125000004744 butyloxycarbonyl group Chemical group 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
150000001733 carboxylic acid esters Chemical class 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
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238000000576 coating method Methods 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
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JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
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244000144972 livestock Species 0.000 description 2
229940043265 methyl isobutyl ketone Drugs 0.000 description 2
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230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
150000001346 alkyl aryl ethers Chemical class 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
229940072049 amyl acetate Drugs 0.000 description 1
PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
239000000921 anthelmintic agent Substances 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
230000002155 anti-virotic effect Effects 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000001491 aromatic compounds Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
229960000892 attapulgite Drugs 0.000 description 1
239000005667 attractant Substances 0.000 description 1
JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
239000002585 base Substances 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
235000010233 benzoic acid Nutrition 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000005540 biological transmission Effects 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
125000006267 biphenyl group Chemical group 0.000 description 1
235000008429 bread Nutrition 0.000 description 1
150000001649 bromium compounds Chemical class 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
150000001804 chlorine Chemical class 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
150000008422 chlorobenzenes Chemical class 0.000 description 1
230000007665 chronic toxicity Effects 0.000 description 1
231100000160 chronic toxicity Toxicity 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
229940125782 compound 2 Drugs 0.000 description 1
229940126214 compound 3 Drugs 0.000 description 1
239000012024 dehydrating agents‎ Substances 0.000 description 1
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 1
GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
229940113088 dimethylacetamide Drugs 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000009826 distribution Methods 0.000 description 1
125000004119 disulfanediyl group Chemical group *SS* 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000010410 dusting Methods 0.000 description 1
235000013399 edible fruits Nutrition 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
238000003912 environmental pollution Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000001125 extrusion Methods 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
DIRFUJHNVNOBMY-UHFFFAOYSA-N fenobucarb Chemical compound CCC(C)C1=CC=CC=C1OC(=O)NC DIRFUJHNVNOBMY-UHFFFAOYSA-N 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
238000003958 fumigation Methods 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
238000005469 granulation Methods 0.000 description 1
230000003179 granulation Effects 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
238000007654 immersion Methods 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
238000011081 inoculation Methods 0.000 description 1
150000002484 inorganic compounds Chemical class 0.000 description 1
229910010272 inorganic material Inorganic materials 0.000 description 1
150000004694 iodide salts Chemical class 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
238000003973 irrigation Methods 0.000 description 1
230000002262 irrigation Effects 0.000 description 1
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
229960004592 isopropanol Drugs 0.000 description 1
QPPQHRDVPBTVEV-UHFFFAOYSA-N isopropyl dihydrogen phosphate Chemical compound CC(C)OP(O)(O)=O QPPQHRDVPBTVEV-UHFFFAOYSA-N 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
239000003350 kerosene Substances 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
UWRBYRMOUPAKLM-UHFFFAOYSA-L lead arsenate Chemical compound [Pb+2].O[As]([O-])([O-])=O UWRBYRMOUPAKLM-UHFFFAOYSA-L 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
JZMJDSHXVKJFKW-UHFFFAOYSA-N methyl sulfate Chemical class COS(O)(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-N 0.000 description 1
JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
229910052901 montmorillonite Inorganic materials 0.000 description 1
230000001069 nematicidal effect Effects 0.000 description 1
239000005645 nematicide Substances 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
150000004045 organic chlorine compounds Chemical class 0.000 description 1
150000002903 organophosphorus compounds Chemical class 0.000 description 1
229910052625 palygorskite Inorganic materials 0.000 description 1
210000005037 parasympathetic nerve Anatomy 0.000 description 1
239000006072 paste Substances 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
150000003014 phosphoric acid esters Chemical class 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
VKCORPXOKYDINR-UHFFFAOYSA-N piperidin-4-ol;hydrochloride Chemical class [Cl-].OC1CC[NH2+]CC1 VKCORPXOKYDINR-UHFFFAOYSA-N 0.000 description 1
239000005648 plant growth regulator Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
239000003380 propellant Substances 0.000 description 1
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
239000010453 quartz Substances 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
235000015170 shellfish Nutrition 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000005507 spraying Methods 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
125000001174 sulfone group Chemical group 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
239000012085 test solution Substances 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
NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
239000002699 waste material Substances 0.000 description 1
238000009333 weeding Methods 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D211/78—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Hydrogenated Pyridines (AREA)

IE2473/75A 1974-11-14 1975-11-13 Tetrahydropyridine carboxylic acid esters and salts thereof,and their use as insecticidal and acaricidal agents IE42138B1 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP49130513A JPS5157824A (en)	1974-11-14	1974-11-14	Satsuchu satsudanizai

Publications (2)

Publication Number	Publication Date
IE42138L IE42138L (en)	1976-05-14
IE42138B1 true IE42138B1 (en)	1980-06-04

Family

ID=15036077

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IE2473/75A IE42138B1 (en)	1974-11-14	1975-11-13	Tetrahydropyridine carboxylic acid esters and salts thereof,and their use as insecticidal and acaricidal agents

Country Status (12)

Country	Link
JP (1)	JPS5157824A (da)
BE (1)	BE835531A (da)
BR (1)	BR7507530A (da)
DE (1)	DE2550957A1 (da)
DK (1)	DK511775A (da)
FR (1)	FR2291193A1 (da)
GB (1)	GB1468644A (da)
IE (1)	IE42138B1 (da)
IL (1)	IL48457A (da)
IT (1)	IT1049069B (da)
LU (1)	LU73788A1 (da)
NL (1)	NL7513358A (da)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4374991A (en)	1976-12-17	1983-02-22	Rohm And Haas Company	2,6-Dimethylpiperidinyl-N-carbobutoxymethyl urea
US4400512A (en) *	1976-12-17	1983-08-23	Rohm And Haas Company	Azaspiro compounds
US4405630A (en) *	1980-12-29	1983-09-20	Rohm And Haas Company	Arthropod repellent compositions and methods
CN118955359A (zh) *	2024-07-31	2024-11-15	海南大学	一种槟榔碱酯类衍生物及其制备方法和应用

1974
- 1974-11-14 JP JP49130513A patent/JPS5157824A/ja active Pending
1975
- 1975-10-23 GB GB4359375A patent/GB1468644A/en not_active Expired
- 1975-11-11 IL IL48457A patent/IL48457A/xx unknown
- 1975-11-12 LU LU73788A patent/LU73788A1/xx unknown
- 1975-11-12 IT IT29210/75A patent/IT1049069B/it active
- 1975-11-13 DE DE19752550957 patent/DE2550957A1/de active Pending
- 1975-11-13 BE BE161832A patent/BE835531A/xx unknown
- 1975-11-13 DK DK511775A patent/DK511775A/da unknown
- 1975-11-13 IE IE2473/75A patent/IE42138B1/en unknown
- 1975-11-13 BR BR7507530*A patent/BR7507530A/pt unknown
- 1975-11-14 FR FR7534831A patent/FR2291193A1/fr not_active Withdrawn
- 1975-11-14 NL NL7513358A patent/NL7513358A/xx not_active Application Discontinuation

Also Published As

Publication number	Publication date
BE835531A (fr)	1976-05-13
GB1468644A (en)	1977-03-30
NL7513358A (nl)	1976-05-18
FR2291193A1 (fr)	1976-06-11
LU73788A1 (da)	1976-09-06
IL48457A0 (en)	1976-01-30
DE2550957A1 (de)	1976-05-20
IE42138L (en)	1976-05-14
JPS5157824A (en)	1976-05-20
IT1049069B (it)	1981-01-20
IL48457A (en)	1978-12-17
BR7507530A (pt)	1976-08-03
DK511775A (da)	1976-05-15

Publication	Publication Date	Title
US2910402A (en)	1959-10-27	Compositions and methods for destroying insects
US2799685A (en)	1957-07-16	Unsaturated polycyclic sulfites and a process for their manufacture
US3501578A (en)	1970-03-17	Fungicidal composition containing phenyl - mercaptomethane-sulfonamide and method of using the same
US2994638A (en)	1961-08-01	Agent for combating rodents
US3003916A (en)	1961-10-10	Vinyl phosphate insecticides
EP0228222B1 (en)	1990-05-23	Pesticidal dihalovinylalkenylamides
DE2525855C3 (de)	1978-06-22	Substituierte Benzoesäureanilide sowie ein diese Verbindungen enthaltendes Mittel
US4096268A (en)	1978-06-20	1-Methyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid esters and a method of use for combating insects or acarids
IE42138B1 (en)	1980-06-04	Tetrahydropyridine carboxylic acid esters and salts thereof,and their use as insecticidal and acaricidal agents
US4024277A (en)	1977-05-17	Phosphoro-aminosulfenyl derivatives of benzofuran carbamates
EP0007020B1 (de)	1981-10-14	Organische Phosphorsäureester, Verfahren zu ihrer Herstellung, ihre Verwendung, Schädlingsbekämpfungsmittel und ihre Herstellung
US3689604A (en)	1972-09-05	Amido-thiolphosphoric acid -o,s-dimethyl ester
US3384538A (en)	1968-05-21	Combatting insects with omicron-[-2-lower alkyl-quinolyl-(8)]n-methyl carbamates
US3590074A (en)	1971-06-29	Chlor-methyl-isopropyl-phenyl-n-methyl carbamate
CA1077958A (en)	1980-05-20	Pesticidal phenoxyphenoxyalkyl cyclopropane carboxylates
US3470229A (en)	1969-09-30	O,o-dialkyl-o-(dithiocarbonato) ethyl-phosphoric acid esters
EP0019581A1 (de)	1980-11-26	1-Imidazolo-N-(phenyl)-azomethin-Derivate, Verfahren zu ihrer Herstellung, diese Verbindungen enthaltende Mittel und ihre Verwendung zur Bekämpfung von Schädlingen
US2844454A (en)	1958-07-22	Biological toxicant
IL25184A (en)	1970-01-29	Phosphoric acid esters,process for the manufacture thereof,and their use as pesticides
US3637800A (en)	1972-01-25	Polychloro- or bromomucononitrile
US3433826A (en)	1969-03-18	Alkoxyphenyl-n-methyl carbamic acid ester
US4201789A (en)	1980-05-06	Cyclopropanecarboxylic acid naphthylmethyl ester
US3763288A (en)	1973-10-02	O lower alkyl o substituted phenyl s alkoxyethylphosphorothiolates
US3816622A (en)	1974-06-11	3-phosphorylthio acrylamide biocidal compositions
IL37390A (en)	1974-07-31	Imidazolyl-alkyl-thiophosphates and thiophosphonates,their manufacture and their use as pesticides