GB1587571A - 2-cyclo-propylamino-4 -formylamino-6-aminos-triazine derivatives and their use as insecticides - Google Patents
2-cyclo-propylamino-4 -formylamino-6-aminos-triazine derivatives and their use as insecticides Download PDFInfo
- Publication number
- GB1587571A GB1587571A GB34791/77A GB3479177A GB1587571A GB 1587571 A GB1587571 A GB 1587571A GB 34791/77 A GB34791/77 A GB 34791/77A GB 3479177 A GB3479177 A GB 3479177A GB 1587571 A GB1587571 A GB 1587571A
- Authority
- GB
- United Kingdom
- Prior art keywords
- represents hydrogen
- cyclopropylamino
- formylamino
- triazine
- formula
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- UJHXWQOAAZCHAU-UHFFFAOYSA-N n-[4-amino-6-(cyclopropylamino)-1,3,5-triazin-2-yl]formamide Chemical class NC1=NC(NC=O)=NC(NC2CC2)=N1 UJHXWQOAAZCHAU-UHFFFAOYSA-N 0.000 title claims description 15
- 239000002917 insecticide Substances 0.000 title description 6
- 239000001257 hydrogen Substances 0.000 claims description 46
- 229910052739 hydrogen Inorganic materials 0.000 claims description 46
- 150000001875 compounds Chemical class 0.000 claims description 45
- 239000013543 active substance Substances 0.000 claims description 37
- -1 hydroxy, methoxy Chemical group 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 22
- 150000002431 hydrogen Chemical group 0.000 claims description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
- 229910052757 nitrogen Inorganic materials 0.000 claims description 21
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 21
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 15
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 11
- 239000008187 granular material Substances 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
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- 239000002253 acid Substances 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 7
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 7
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- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 6
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 6
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 6
- 241000255925 Diptera Species 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
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- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
- NBRRMXJYDCCOBU-UHFFFAOYSA-N n-[4-(cyclopropylamino)-6-morpholin-4-yl-1,3,5-triazin-2-yl]formamide Chemical compound N=1C(N2CCOCC2)=NC(NC=O)=NC=1NC1CC1 NBRRMXJYDCCOBU-UHFFFAOYSA-N 0.000 claims description 4
- 239000007921 spray Substances 0.000 claims description 4
- 238000012360 testing method Methods 0.000 claims description 4
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 3
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- LVQDKIWDGQRHTE-UHFFFAOYSA-N cyromazine Chemical compound NC1=NC(N)=NC(NC2CC2)=N1 LVQDKIWDGQRHTE-UHFFFAOYSA-N 0.000 claims description 3
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- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- PWFRLUQROTUDTJ-UHFFFAOYSA-N n-[4-(cyclopropylamino)-6-(prop-2-ynylamino)-1,3,5-triazin-2-yl]formamide Chemical compound O=CNC1=NC(NCC#C)=NC(NC2CC2)=N1 PWFRLUQROTUDTJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
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- ZVMJRFPTQAYKHD-UHFFFAOYSA-N n-[4-(cyclopropylamino)-6-(ethylamino)-1,3,5-triazin-2-yl]formamide Chemical compound CCNC1=NC(NC=O)=NC(NC2CC2)=N1 ZVMJRFPTQAYKHD-UHFFFAOYSA-N 0.000 claims description 2
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- GOQYKNQRPGWPLP-UHFFFAOYSA-N heptadecan-1-ol Chemical class CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical class CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 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
- 239000002949 juvenile hormone Substances 0.000 description 1
- 229930014550 juvenile hormone Natural products 0.000 description 1
- 150000003633 juvenile hormone derivatives Chemical class 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 230000029052 metamorphosis Effects 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 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
- REVYMWLDXAUASZ-UHFFFAOYSA-N n-(4,6-diamino-1,3,5-triazin-2-yl)acetamide Chemical class CC(=O)NC1=NC(N)=NC(N)=N1 REVYMWLDXAUASZ-UHFFFAOYSA-N 0.000 description 1
- VEVMNNRCFMDJOA-UHFFFAOYSA-N n-[4,6-bis(cyclopropylamino)-1,3,5-triazin-2-yl]formamide Chemical compound N=1C(NC2CC2)=NC(NC=O)=NC=1NC1CC1 VEVMNNRCFMDJOA-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 150000002905 orthoesters Chemical class 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 235000012219 potassium aluminium silicate Nutrition 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 235000012217 sodium aluminium silicate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000002336 sorption--desorption measurement Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/54—Three nitrogen atoms
- C07D251/70—Other substituted melamines
-
- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
- A01N43/68—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms with two or three nitrogen atoms directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1055976A CH603049A5 (en) | 1976-08-19 | 1976-08-19 | (2)-Cyclopropyl-amino-(4)-formyl-amino-(1,3,5)-triazine cpds. |
| CH271977 | 1977-03-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1587571A true GB1587571A (en) | 1981-04-08 |
Family
ID=25691230
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB34791/77A Expired GB1587571A (en) | 1976-08-19 | 1977-08-18 | 2-cyclo-propylamino-4 -formylamino-6-aminos-triazine derivatives and their use as insecticides |
Country Status (11)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ221262A (en) * | 1986-08-06 | 1990-08-28 | Ciba Geigy Ag | Preventing the reinfestation of dogs and cats by fleas by administering to the host a flea growth inhibiting substance orally, parenterally or by implant |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL39385A (en) * | 1971-06-01 | 1974-12-31 | Ciba Geigy Ag | A method for combating insects by the use of 4-azido-2,6-diamino triazine derivatives,certain such novel derivatives and their manufacture |
-
1977
- 1977-08-16 DE DE19772736699 patent/DE2736699A1/de not_active Withdrawn
- 1977-08-17 CA CA284,902A patent/CA1084923A/en not_active Expired
- 1977-08-17 NL NL7709098A patent/NL7709098A/xx not_active Application Discontinuation
- 1977-08-17 IL IL52766A patent/IL52766A/xx unknown
- 1977-08-17 YU YU01989/77A patent/YU198977A/xx unknown
- 1977-08-18 ES ES461716A patent/ES461716A1/es not_active Expired
- 1977-08-18 NZ NZ184954A patent/NZ184954A/xx unknown
- 1977-08-18 FR FR7725248A patent/FR2362135A1/fr active Granted
- 1977-08-18 GB GB34791/77A patent/GB1587571A/en not_active Expired
- 1977-08-19 AU AU28042/77A patent/AU518857B2/en not_active Expired
- 1977-08-19 JP JP9939977A patent/JPS5325586A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| AU518857B2 (en) | 1981-10-22 |
| IL52766A (en) | 1981-02-27 |
| FR2362135A1 (fr) | 1978-03-17 |
| YU198977A (en) | 1982-08-31 |
| FR2362135B1 (enrdf_load_stackoverflow) | 1980-06-27 |
| IL52766A0 (en) | 1977-10-31 |
| JPS638105B2 (enrdf_load_stackoverflow) | 1988-02-19 |
| ES461716A1 (es) | 1978-12-16 |
| JPS5325586A (en) | 1978-03-09 |
| AU2804277A (en) | 1979-02-22 |
| NL7709098A (nl) | 1978-02-21 |
| DE2736699A1 (de) | 1978-06-22 |
| NZ184954A (en) | 1980-05-08 |
| CA1084923A (en) | 1980-09-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |