CS197232B2 - Insecticide means notably against the plant louses and method of making the active substance - Google Patents
Insecticide means notably against the plant louses and method of making the active substance Download PDFInfo
- Publication number
- CS197232B2 CS197232B2 CS744058A CS405874A CS197232B2 CS 197232 B2 CS197232 B2 CS 197232B2 CS 744058 A CS744058 A CS 744058A CS 405874 A CS405874 A CS 405874A CS 197232 B2 CS197232 B2 CS 197232B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- formula
- methyl
- hydrogen
- compound
- ethyl
- Prior art date
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- 239000013543 active substance Substances 0.000 title description 5
- 239000002917 insecticide Substances 0.000 title description 4
- 238000004519 manufacturing process Methods 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 abstract description 82
- -1 4 - methylpiperazinyl Chemical group 0.000 abstract description 39
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 30
- 239000001257 hydrogen Substances 0.000 abstract description 19
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 19
- 150000001412 amines Chemical class 0.000 abstract description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract description 15
- 239000012948 isocyanate Substances 0.000 abstract description 14
- 150000002513 isocyanates Chemical class 0.000 abstract description 14
- 150000002431 hydrogen Chemical class 0.000 abstract description 11
- 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 description 11
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract description 9
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- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 5
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 abstract description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract description 3
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- 125000003342 alkenyl group Chemical group 0.000 abstract description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract description 2
- 125000003545 alkoxy group Chemical group 0.000 abstract description 2
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- 229910052731 fluorine Inorganic materials 0.000 abstract description 2
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- 241000228452 Venturia inaequalis Species 0.000 description 1
- NOABJNYOHPTKLL-UHFFFAOYSA-N [[1-(dimethylamino)-3-methoxyimino-1-oxobutan-2-ylidene]amino] N,N-dimethylcarbamate Chemical compound CON=C(C)C(C(=O)N(C)C)=NOC(=O)N(C)C NOABJNYOHPTKLL-UHFFFAOYSA-N 0.000 description 1
- WKZLYEJGOQQZGO-UHFFFAOYSA-N [[1-(dimethylamino)-3-methoxyimino-1-oxobutan-2-ylidene]amino] n,n-diethylcarbamate Chemical compound CCN(CC)C(=O)ON=C(C(=O)N(C)C)C(C)=NOC WKZLYEJGOQQZGO-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 150000004729 acetoacetic acid derivatives Chemical class 0.000 description 1
- KLUDQUOLAFVLOL-UHFFFAOYSA-N acetyl propanoate Chemical class CCC(=O)OC(C)=O KLUDQUOLAFVLOL-UHFFFAOYSA-N 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical class 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- RIOXQFHNBCKOKP-UHFFFAOYSA-N benomyl Chemical compound C1=CC=C2N(C(=O)NCCCC)C(NC(=O)OC)=NC2=C1 RIOXQFHNBCKOKP-UHFFFAOYSA-N 0.000 description 1
- MITFXPHMIHQXPI-UHFFFAOYSA-N benzoxaprofen Natural products N=1C2=CC(C(C(O)=O)C)=CC=C2OC=1C1=CC=C(Cl)C=C1 MITFXPHMIHQXPI-UHFFFAOYSA-N 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000013043 chemical agent Substances 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 229940127573 compound 38 Drugs 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 230000008029 eradication Effects 0.000 description 1
- IACSYDRIOYGJNH-UHFFFAOYSA-N ethyl 2-hydroxyimino-3-oxobutanoate Chemical compound CCOC(=O)C(=NO)C(C)=O IACSYDRIOYGJNH-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000021384 green leafy vegetables Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 238000011221 initial treatment Methods 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 235000014666 liquid concentrate Nutrition 0.000 description 1
- 230000001926 lymphatic effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- MKQLBNJQQZRQJU-UHFFFAOYSA-N morpholin-4-amine Chemical compound NN1CCOCC1 MKQLBNJQQZRQJU-UHFFFAOYSA-N 0.000 description 1
- OFCCYDUUBNUJIB-UHFFFAOYSA-N n,n-diethylcarbamoyl chloride Chemical compound CCN(CC)C(Cl)=O OFCCYDUUBNUJIB-UHFFFAOYSA-N 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- NUXCOKIYARRTDC-UHFFFAOYSA-N o-ethylhydroxylamine;hydron;chloride Chemical compound Cl.CCON NUXCOKIYARRTDC-UHFFFAOYSA-N 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 239000012053 oil suspension Substances 0.000 description 1
- PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000011265 semifinished product Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000004546 suspension concentrate Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 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
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
-
- 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
- C07D295/22—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 with hetero atoms directly attached to ring nitrogen atoms
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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US36960673A | 1973-06-13 | 1973-06-13 | |
| US05/463,987 US4059623A (en) | 1973-06-13 | 1974-04-25 | Butyramides and butyrates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS197232B2 true CS197232B2 (en) | 1980-04-30 |
Family
ID=27004643
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS744058A CS197232B2 (en) | 1973-06-13 | 1974-06-07 | Insecticide means notably against the plant louses and method of making the active substance |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US4059623A (en, 2012) |
| JP (1) | JPS5757445B2 (en, 2012) |
| AR (1) | AR216040A1 (en, 2012) |
| BR (1) | BR7404848D0 (en, 2012) |
| CA (1) | CA1031341A (en, 2012) |
| CH (1) | CH600763A5 (en, 2012) |
| CS (1) | CS197232B2 (en, 2012) |
| DD (1) | DD118511A5 (en, 2012) |
| DE (1) | DE2428070C2 (en, 2012) |
| DK (1) | DK314374A (en, 2012) |
| ES (1) | ES427185A1 (en, 2012) |
| FR (1) | FR2233317B1 (en, 2012) |
| GB (1) | GB1438426A (en, 2012) |
| IE (1) | IE39284B1 (en, 2012) |
| IL (1) | IL45017A (en, 2012) |
| IT (1) | IT1049223B (en, 2012) |
| NL (1) | NL7407926A (en, 2012) |
| NO (1) | NO139220C (en, 2012) |
| PH (1) | PH11491A (en, 2012) |
| PL (1) | PL94958B1 (en, 2012) |
| SE (1) | SE7406469L (en, 2012) |
| YU (2) | YU166674A (en, 2012) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4435421A (en) | 1978-11-03 | 1984-03-06 | Union Carbide Corporation | Biocidal sulfur-containing bis-imino carbamate compounds |
| US4725682A (en) * | 1978-11-03 | 1988-02-16 | Rhone-Poulenc Nederland, B.V. | Biocidal sulfur-containing bis-imino carbamate compounds |
| US4657904A (en) * | 1978-11-03 | 1987-04-14 | Union Carbide Corporation | Sulfur-containing bis-imino carbamate compounds, pesticidal composition and use |
| EP0387499B1 (de) * | 1989-02-16 | 1993-12-22 | Bayer Ag | Substituierte Oximether sowie deren Verwendung als Schädlingsbekämpfungsmittel |
| US6096741A (en) | 1996-10-15 | 2000-08-01 | Shionogi & Co., Ltd. | Oxime derivatives, hydrazone derivatives and use thereof |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2542812A (en) * | 1946-04-03 | 1951-02-20 | Walter H Hartung | Preparation of aminoacidamides |
| US3849481A (en) * | 1970-12-11 | 1974-11-19 | Allied Chem | Hydrogenation of lysine precursors |
-
1974
- 1974-04-25 US US05/463,987 patent/US4059623A/en not_active Expired - Lifetime
- 1974-05-15 SE SE7406469A patent/SE7406469L/xx unknown
- 1974-05-22 IE IE1098/74A patent/IE39284B1/xx unknown
- 1974-06-07 CS CS744058A patent/CS197232B2/cs unknown
- 1974-06-11 JP JP49065669A patent/JPS5757445B2/ja not_active Expired
- 1974-06-11 ES ES427185A patent/ES427185A1/es not_active Expired
- 1974-06-11 IT IT23856/74A patent/IT1049223B/it active
- 1974-06-11 DE DE2428070A patent/DE2428070C2/de not_active Expired
- 1974-06-11 CA CA202,336A patent/CA1031341A/en not_active Expired
- 1974-06-12 GB GB2608774A patent/GB1438426A/en not_active Expired
- 1974-06-12 BR BR4848/74A patent/BR7404848D0/pt unknown
- 1974-06-12 PL PL1974171858A patent/PL94958B1/pl unknown
- 1974-06-12 AR AR254171A patent/AR216040A1/es active
- 1974-06-12 DK DK314374A patent/DK314374A/da unknown
- 1974-06-12 CH CH805974A patent/CH600763A5/xx not_active IP Right Cessation
- 1974-06-12 NO NO742129A patent/NO139220C/no unknown
- 1974-06-12 DD DD179108A patent/DD118511A5/xx unknown
- 1974-06-12 FR FR7420317A patent/FR2233317B1/fr not_active Expired
- 1974-06-12 IL IL45017A patent/IL45017A/xx unknown
- 1974-06-13 NL NL7407926A patent/NL7407926A/xx not_active Application Discontinuation
- 1974-06-13 YU YU01666/74A patent/YU166674A/xx unknown
- 1974-06-13 PH PH15934A patent/PH11491A/en unknown
-
1981
- 1981-09-09 YU YU02156/81A patent/YU215681A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO139220B (no) | 1978-10-16 |
| YU215681A (en) | 1982-08-31 |
| FR2233317A1 (en, 2012) | 1975-01-10 |
| JPS5757445B2 (en, 2012) | 1982-12-04 |
| IE39284B1 (en) | 1978-09-13 |
| IE39284L (en) | 1974-12-13 |
| NL7407926A (en, 2012) | 1974-12-17 |
| BR7404848D0 (pt) | 1975-09-23 |
| DE2428070C2 (de) | 1985-10-10 |
| PH11491A (en) | 1978-02-01 |
| AR216040A1 (es) | 1979-11-30 |
| FR2233317B1 (en, 2012) | 1978-01-13 |
| ES427185A1 (es) | 1976-09-16 |
| YU166674A (en) | 1982-02-28 |
| JPS5035336A (en, 2012) | 1975-04-04 |
| IT1049223B (it) | 1981-01-20 |
| US4059623A (en) | 1977-11-22 |
| AU6999674A (en) | 1975-12-11 |
| SE7406469L (en, 2012) | 1974-12-16 |
| GB1438426A (en) | 1976-06-09 |
| NO742129L (en, 2012) | 1975-01-06 |
| CH600763A5 (en, 2012) | 1978-06-30 |
| DE2428070A1 (de) | 1975-01-09 |
| DD118511A5 (en, 2012) | 1976-03-12 |
| DK314374A (en, 2012) | 1975-02-03 |
| IL45017A (en) | 1978-01-31 |
| CA1031341A (en) | 1978-05-16 |
| IL45017A0 (en) | 1974-09-10 |
| NO139220C (no) | 1979-01-24 |
| PL94958B1 (en, 2012) | 1977-09-30 |
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