IL42156A - Substituted butenoic acid derivatives their manufacture and use as pesticides - Google Patents
Substituted butenoic acid derivatives their manufacture and use as pesticidesInfo
- Publication number
- IL42156A IL42156A IL42156A IL4215673A IL42156A IL 42156 A IL42156 A IL 42156A IL 42156 A IL42156 A IL 42156A IL 4215673 A IL4215673 A IL 4215673A IL 42156 A IL42156 A IL 42156A
- Authority
- IL
- Israel
- Prior art keywords
- methyl
- carbonyl
- formula
- alkyl
- phenoxy
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims 6
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical class C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 title 1
- 239000000575 pesticide Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 33
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 32
- 239000001257 hydrogen Substances 0.000 claims abstract 31
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract 27
- -1 cyclohexyloxycarbonyl Chemical group 0.000 claims abstract 22
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 10
- 229910052736 halogen Inorganic materials 0.000 claims abstract 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract 6
- 239000005864 Sulphur Substances 0.000 claims abstract 6
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims abstract 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract 6
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract 6
- 239000001301 oxygen Substances 0.000 claims abstract 6
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 6
- 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 abstract 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract 4
- 239000002253 acid Substances 0.000 claims abstract 4
- 239000002585 base Substances 0.000 claims abstract 4
- 239000003795 chemical substances by application Substances 0.000 claims abstract 4
- 125000006678 phenoxycarbonyl group Chemical group 0.000 claims abstract 4
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 3
- 239000003377 acid catalyst Substances 0.000 claims abstract 2
- 239000003513 alkali Substances 0.000 claims abstract 2
- 125000004429 atom Chemical group 0.000 claims abstract 2
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 claims abstract 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims abstract 2
- 230000000361 pesticidal effect Effects 0.000 claims abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 18
- 150000002431 hydrogen Chemical class 0.000 claims 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 14
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 13
- 238000000034 method Methods 0.000 claims 7
- 239000000460 chlorine Substances 0.000 claims 6
- 125000005291 haloalkenyloxy group Chemical group 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- 125000001424 substituent group Chemical group 0.000 claims 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 5
- 229910052801 chlorine Inorganic materials 0.000 claims 5
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 4
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 4
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 3
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 claims 3
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 3
- QOXDLLMBWRPFRL-UHFFFAOYSA-N 3-methyl-4-(4-phenoxyphenoxy)but-2-enoic acid Chemical compound C1=CC(OCC(C)=CC(O)=O)=CC=C1OC1=CC=CC=C1 QOXDLLMBWRPFRL-UHFFFAOYSA-N 0.000 claims 2
- FMSQUVJPGIFFTD-UHFFFAOYSA-N 4-(4-benzylphenoxy)-3-methylbut-2-enoic acid Chemical compound C1=CC(OCC(C)=CC(O)=O)=CC=C1CC1=CC=CC=C1 FMSQUVJPGIFFTD-UHFFFAOYSA-N 0.000 claims 2
- 239000013543 active substance Substances 0.000 claims 2
- 239000002168 alkylating agent Substances 0.000 claims 2
- 229940100198 alkylating agent Drugs 0.000 claims 2
- 125000004744 butyloxycarbonyl group Chemical group 0.000 claims 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 2
- 125000004494 ethyl ester group Chemical group 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- BDLSTAXMFZZVBH-UHFFFAOYSA-N 4-(4-benzylphenoxy)-n,n-diethyl-3-methylbut-2-enamide Chemical compound C1=CC(OCC(C)=CC(=O)N(CC)CC)=CC=C1CC1=CC=CC=C1 BDLSTAXMFZZVBH-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 241000238631 Hexapoda Species 0.000 claims 1
- 241000607479 Yersinia pestis Species 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- UZBQIPPOMKBLAS-UHFFFAOYSA-N diethylazanide Chemical compound CC[N-]CC UZBQIPPOMKBLAS-UHFFFAOYSA-N 0.000 claims 1
- KAYFNEZQOYQZSG-UHFFFAOYSA-N ethyl 4-(4-benzylphenoxy)-3-methylbut-2-enoate Chemical compound C1=CC(OCC(C)=CC(=O)OCC)=CC=C1CC1=CC=CC=C1 KAYFNEZQOYQZSG-UHFFFAOYSA-N 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- RZDCEQZHXLBBPE-UHFFFAOYSA-N methyl 3-methyl-4-(4-phenoxyanilino)but-2-enoate Chemical compound C1=CC(NCC(C)=CC(=O)OC)=CC=C1OC1=CC=CC=C1 RZDCEQZHXLBBPE-UHFFFAOYSA-N 0.000 claims 1
- YCJONXMWOXLIQF-UHFFFAOYSA-N methyl 4-(4-benzylphenoxy)-3-methylbut-2-enoate Chemical compound C1=CC(OCC(C)=CC(=O)OC)=CC=C1CC1=CC=CC=C1 YCJONXMWOXLIQF-UHFFFAOYSA-N 0.000 claims 1
- 150000004702 methyl esters Chemical class 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 claims 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract 6
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- 125000005843 halogen group Chemical group 0.000 abstract 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 2
- 239000004606 Fillers/Extenders Substances 0.000 abstract 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000003302 alkenyloxy group Chemical group 0.000 abstract 2
- 125000000304 alkynyl group Chemical group 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 239000007787 solid Substances 0.000 abstract 2
- 239000004094 surface-active agent Substances 0.000 abstract 2
- PECAJBKESXSWGZ-UHFFFAOYSA-N 1-(4-benzoylphenoxy)propan-2-one Chemical compound C1=CC(OCC(=O)C)=CC=C1C(=O)C1=CC=CC=C1 PECAJBKESXSWGZ-UHFFFAOYSA-N 0.000 abstract 1
- UHIDXDTXRPEJKK-UHFFFAOYSA-N 1-(4-benzylphenoxy)propan-2-one Chemical compound C1=CC(OCC(=O)C)=CC=C1CC1=CC=CC=C1 UHIDXDTXRPEJKK-UHFFFAOYSA-N 0.000 abstract 1
- LTHRKIOMIFATNQ-UHFFFAOYSA-N 1-(4-phenoxyphenoxy)propan-2-one Chemical compound C1=CC(OCC(=O)C)=CC=C1OC1=CC=CC=C1 LTHRKIOMIFATNQ-UHFFFAOYSA-N 0.000 abstract 1
- XYRDOYWGRWXCKC-UHFFFAOYSA-N 1-benzyl-4-prop-2-ynoxybenzene Chemical compound C1=CC(OCC#C)=CC=C1CC1=CC=CC=C1 XYRDOYWGRWXCKC-UHFFFAOYSA-N 0.000 abstract 1
- FHHHSQLDERWINF-UHFFFAOYSA-N 1-benzyl-4-propoxybenzene Chemical compound C1=CC(OCCC)=CC=C1CC1=CC=CC=C1 FHHHSQLDERWINF-UHFFFAOYSA-N 0.000 abstract 1
- JBLNLPKHCICEDE-UHFFFAOYSA-N 3-(4-phenoxyphenoxy)butan-2-one Chemical compound C1=CC(OC(C)C(C)=O)=CC=C1OC1=CC=CC=C1 JBLNLPKHCICEDE-UHFFFAOYSA-N 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 1
- 230000002152 alkylating effect Effects 0.000 abstract 1
- 125000005133 alkynyloxy group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 125000006413 ring segment Chemical group 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/515—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an acetalised, ketalised hemi-acetalised, or hemi-ketalised hydroxyl group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/255—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
- C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH701172A CH566709A5 (en) | 1972-05-10 | 1972-05-10 | Phenyl-substd butenoic acid derivs - with insectidal activity |
| CH1425572A CH578317A5 (en) | 1972-09-29 | 1972-09-29 | Phenyl-substd butenoic acid derivs - with insectidal activity |
| CH456773A CH578825A5 (en) | 1973-03-29 | 1973-03-29 | Phenyl-substd butenoic acid derivs - with insectidal activity |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL42156A0 IL42156A0 (en) | 1973-07-30 |
| IL42156A true IL42156A (en) | 1976-11-30 |
Family
ID=27174895
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL42156A IL42156A (en) | 1972-05-10 | 1973-05-01 | Substituted butenoic acid derivatives their manufacture and use as pesticides |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS6011005B2 (en(2012)) |
| AT (1) | AT328223B (en(2012)) |
| CA (1) | CA1055511A (en(2012)) |
| DD (1) | DD109315A5 (en(2012)) |
| DE (1) | DE2322853C3 (en(2012)) |
| DK (1) | DK134463B (en(2012)) |
| EG (1) | EG11425A (en(2012)) |
| ES (1) | ES414565A1 (en(2012)) |
| FI (1) | FI55986C (en(2012)) |
| FR (1) | FR2189368B1 (en(2012)) |
| GB (1) | GB1422181A (en(2012)) |
| HU (1) | HU168015B (en(2012)) |
| IL (1) | IL42156A (en(2012)) |
| IT (1) | IT994860B (en(2012)) |
| NL (1) | NL175813C (en(2012)) |
| OA (1) | OA04387A (en(2012)) |
| PH (1) | PH10001A (en(2012)) |
| SE (1) | SE402584B (en(2012)) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1479297A (en) * | 1974-07-04 | 1977-07-13 | Beecham Group Ltd | 4-substituted butan-2-ones but-3-en-2-ones butan-2-ols and but-3-en-2-ols and pharmaceutical compositions containing them |
| CH609024A5 (en) * | 1974-09-30 | 1979-02-15 | Lafon Labor | Process for the preparation of new sulphur-containing diaryl and oxygen-containing diaryl compounds |
| MA19610A1 (fr) * | 1981-08-07 | 1983-04-01 | Ciba Geigy Ag | Nouveaux derives de phenoxyphenyl-aminoacide, leurs preparations, produits les contenant et leur utilisation |
-
1973
- 1973-04-16 FI FI1200/73A patent/FI55986C/fi active
- 1973-04-24 SE SE7305715A patent/SE402584B/xx unknown
- 1973-05-01 IL IL42156A patent/IL42156A/en unknown
- 1973-05-03 PH PH14599A patent/PH10001A/en unknown
- 1973-05-07 DE DE2322853A patent/DE2322853C3/de not_active Expired
- 1973-05-09 EG EG170/73A patent/EG11425A/xx active
- 1973-05-09 IT IT23886/73A patent/IT994860B/it active
- 1973-05-09 DD DD170727A patent/DD109315A5/xx unknown
- 1973-05-09 GB GB2221373A patent/GB1422181A/en not_active Expired
- 1973-05-09 ES ES414565A patent/ES414565A1/es not_active Expired
- 1973-05-09 AT AT407773A patent/AT328223B/de not_active IP Right Cessation
- 1973-05-09 DK DK256273AA patent/DK134463B/da unknown
- 1973-05-09 FR FR7316675A patent/FR2189368B1/fr not_active Expired
- 1973-05-09 CA CA170,842A patent/CA1055511A/en not_active Expired
- 1973-05-10 OA OA54907A patent/OA04387A/xx unknown
- 1973-05-10 NL NLAANVRAGE7306547,A patent/NL175813C/xx not_active IP Right Cessation
- 1973-05-10 JP JP48052078A patent/JPS6011005B2/ja not_active Expired
-
1974
- 1974-05-09 HU HUCI1371A patent/HU168015B/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE2322853C3 (de) | 1981-01-15 |
| DK134463C (en(2012)) | 1977-05-16 |
| EG11425A (en) | 1977-08-15 |
| FR2189368A1 (en(2012)) | 1974-01-25 |
| AT328223B (de) | 1976-03-10 |
| ES414565A1 (es) | 1976-05-16 |
| IL42156A0 (en) | 1973-07-30 |
| JPS6011005B2 (ja) | 1985-03-22 |
| GB1422181A (en) | 1976-01-21 |
| SE402584B (sv) | 1978-07-10 |
| AU5527273A (en) | 1974-11-07 |
| FR2189368B1 (en(2012)) | 1978-01-06 |
| IT994860B (it) | 1975-10-20 |
| HU168015B (en(2012)) | 1976-02-28 |
| DE2322853A1 (de) | 1973-11-29 |
| FI55986C (fi) | 1979-11-12 |
| NL175813B (nl) | 1984-08-01 |
| PH10001A (en) | 1976-07-13 |
| NL7306547A (en(2012)) | 1973-11-13 |
| DE2322853B2 (de) | 1980-05-08 |
| NL175813C (nl) | 1985-01-02 |
| CA1055511A (en) | 1979-05-29 |
| DD109315A5 (en(2012)) | 1974-11-05 |
| JPS4954526A (en(2012)) | 1974-05-27 |
| ATA407773A (de) | 1975-05-15 |
| OA04387A (fr) | 1980-02-15 |
| DK134463B (da) | 1976-11-15 |
| FI55986B (fi) | 1979-07-31 |
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