HU180657B - Process for producing 1,3-disubstituted triasine-2,4-diones,and insecticide compositions containing them as active agents - Google Patents

Process for producing 1,3-disubstituted triasine-2,4-diones,and insecticide compositions containing them as active agents Download PDF

Info

Publication number: HU180657B
Authority: HU; Hungary
Prior art keywords: dimethyl; formula; methyl; triazine; diethyl
Prior art date: 1975-09-30

Application number

HU76BA3455A

Other languages

English (en)

Hungarian (hu)

Inventor

Helmut Bredereck

Willi Kantlehner

Wolfgang Kugel

Edgar Moehring

Peter Roessier

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.)

1975-09-30

Filing date

1976-09-29

Publication date

1983-04-29

1976-09-29 Application filed by Bayer Ag filed Critical Bayer Ag

1983-04-29 Publication of HU180657B publication Critical patent/HU180657B/hu

Links

239000000203 mixture Substances 0.000 title claims description 22
238000000034 method Methods 0.000 title claims description 16
230000008569 process Effects 0.000 title claims description 14
239000002917 insecticide Substances 0.000 title description 3
239000013543 active substance Substances 0.000 title description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 7
125000000217 alkyl group Chemical group 0.000 claims abstract description 6
125000001624 naphthyl group Chemical group 0.000 claims abstract description 6
239000012948 isocyanate Substances 0.000 claims abstract description 5
150000002513 isocyanates Chemical class 0.000 claims abstract description 5
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
229910052736 halogen Inorganic materials 0.000 claims abstract description 4
230000000749 insecticidal effect Effects 0.000 claims abstract 2
238000006243 chemical reaction Methods 0.000 claims description 9
238000002360 preparation method Methods 0.000 claims description 8
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 4
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 3
239000000546 pharmaceutical excipient Substances 0.000 claims description 3
229920000151 polyglycol Polymers 0.000 claims description 3
239000010695 polyglycol Substances 0.000 claims description 3
239000004576 sand Substances 0.000 claims description 3
125000002877 alkyl aryl group Chemical group 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
239000003960 organic solvent Substances 0.000 claims description 2
239000004094 surface-active agent Substances 0.000 claims description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
150000003871 sulfonates Chemical class 0.000 claims 1
FRCLVJBDJNNNGI-UHFFFAOYSA-N n,n-bis(trimethylsilyl)formamide Chemical compound C[Si](C)(C)N(C=O)[Si](C)(C)C FRCLVJBDJNNNGI-UHFFFAOYSA-N 0.000 abstract description 7
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 abstract description 3
230000000895 acaricidal effect Effects 0.000 abstract 1
150000001408 amides Chemical class 0.000 abstract 1
150000002367 halogens Chemical class 0.000 abstract 1
-1 chloro, methyl Chemical group 0.000 description 36
229910052760 oxygen Inorganic materials 0.000 description 33
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230000002401 inhibitory effect Effects 0.000 description 5
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FBQQHUGEACOBDN-UHFFFAOYSA-N quinomethionate Chemical compound N1=C2SC(=O)SC2=NC2=CC(C)=CC=C21 FBQQHUGEACOBDN-UHFFFAOYSA-N 0.000 description 5
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HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 3
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125000000068 chlorophenyl group Chemical group 0.000 description 3
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238000010790 dilution Methods 0.000 description 3
239000012895 dilution Substances 0.000 description 3
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 3
230000000694 effects Effects 0.000 description 3
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HDWLUGYOLUHEMN-UHFFFAOYSA-N Dinobuton Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1OC(=O)OC(C)C HDWLUGYOLUHEMN-UHFFFAOYSA-N 0.000 description 2
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150000001491 aromatic compounds Chemical class 0.000 description 2
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ROVGZAWFACYCSP-VUMXUWRFSA-N pyrethrin I Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 ROVGZAWFACYCSP-VUMXUWRFSA-N 0.000 description 1
VJFUPGQZSXIULQ-XIGJTORUSA-N pyrethrin II Chemical compound CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 VJFUPGQZSXIULQ-XIGJTORUSA-N 0.000 description 1
JYQUHIFYBATCCY-UHFFFAOYSA-N quinalphos Chemical compound C1=CC=CC2=NC(OP(=S)(OCC)OCC)=CN=C21 JYQUHIFYBATCCY-UHFFFAOYSA-N 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
239000007921 spray Substances 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
XIUROWKZWPIAIB-UHFFFAOYSA-N sulfotep Chemical compound CCOP(=S)(OCC)OP(=S)(OCC)OCC XIUROWKZWPIAIB-UHFFFAOYSA-N 0.000 description 1
239000013589 supplement Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
229920001059 synthetic polymer Polymers 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
150000003505 terpenes Chemical class 0.000 description 1
235000007586 terpenes Nutrition 0.000 description 1
UBCKGWBNUIFUST-YHYXMXQVSA-N tetrachlorvinphos Chemical compound COP(=O)(OC)O\C(=C/Cl)C1=CC(Cl)=C(Cl)C=C1Cl UBCKGWBNUIFUST-YHYXMXQVSA-N 0.000 description 1
MLGCXEBRWGEOQX-UHFFFAOYSA-N tetradifon Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl MLGCXEBRWGEOQX-UHFFFAOYSA-N 0.000 description 1
239000010409 thin film Substances 0.000 description 1
OPASCBHCTNRLRM-UHFFFAOYSA-N thiometon Chemical compound CCSCCSP(=S)(OC)OC OPASCBHCTNRLRM-UHFFFAOYSA-N 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
HYVWIQDYBVKITD-UHFFFAOYSA-N tolylfluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=C(C)C=C1 HYVWIQDYBVKITD-UHFFFAOYSA-N 0.000 description 1
OEJNXTAZZBRGDN-UHFFFAOYSA-N toxaphene Chemical compound ClC1C(Cl)C2(Cl)C(CCl)(CCl)C(=C)C1(Cl)C2(Cl)Cl OEJNXTAZZBRGDN-UHFFFAOYSA-N 0.000 description 1
239000011573 trace mineral Substances 0.000 description 1
235000013619 trace mineral Nutrition 0.000 description 1
DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
WHNYVDJJCTVMGO-UHFFFAOYSA-N tricyclo[5.2.1.02,6]dec-8-ene Chemical compound C1=CC2CC1C1C2CCC1 WHNYVDJJCTVMGO-UHFFFAOYSA-N 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
LESVOLZBIFDZGS-UHFFFAOYSA-N vamidothion Chemical compound CNC(=O)C(C)SCCSP(=O)(OC)OC LESVOLZBIFDZGS-UHFFFAOYSA-N 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
150000003722 vitamin derivatives Chemical class 0.000 description 1
239000002023 wood Substances 0.000 description 1
150000003751 zinc Chemical class 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
- C07D251/14—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 hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/16—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 hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
- C07D251/20—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 hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom with no nitrogen atoms directly attached to a ring carbon atom

Landscapes

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

HU76BA3455A 1975-09-30 1976-09-29 Process for producing 1,3-disubstituted triasine-2,4-diones,and insecticide compositions containing them as active agents HU180657B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19752543497 DE2543497A1 (de)	1975-09-30	1975-09-30	Verfahren zur herstellung neuer triazin-2,4-dione sowie ihre verwendung als insektizide

Publications (1)

Publication Number	Publication Date
HU180657B true HU180657B (en)	1983-04-29

Family

ID=5957791

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HU76BA3455A HU180657B (en)	1975-09-30	1976-09-29	Process for producing 1,3-disubstituted triasine-2,4-diones,and insecticide compositions containing them as active agents

Country Status (6)

Country	Link
BE (1)	BE846665A (de)
DE (1)	DE2543497A1 (de)
HU (1)	HU180657B (de)
PL (1)	PL102249B1 (de)
SU (1)	SU615836A3 (de)
ZA (1)	ZA765836B (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2723248A1 (de) *	1977-05-24	1978-11-30	Bayer Ag	Insektizide mittel
EP3019481B1 (de) *	2013-07-08	2019-03-06	Bayer CropScience Aktiengesellschaft	Sechsgliedrige c-n-verknüpfte arylsulfid- und arylsulfoxid- derivate als schädlingsbekämpfungsmittel

1975
- 1975-09-30 DE DE19752543497 patent/DE2543497A1/de not_active Withdrawn
1976
- 1976-09-27 SU SU762404600A patent/SU615836A3/ru active
- 1976-09-28 BE BE171007A patent/BE846665A/xx not_active IP Right Cessation
- 1976-09-29 ZA ZA765836A patent/ZA765836B/xx unknown
- 1976-09-29 HU HU76BA3455A patent/HU180657B/hu unknown
- 1976-09-29 PL PL1976192716A patent/PL102249B1/pl unknown

Also Published As

Publication number	Publication date
ZA765836B (en)	1977-09-28
BE846665A (fr)	1977-03-28
DE2543497A1 (de)	1977-04-07
SU615836A3 (ru)	1978-07-15
PL102249B1 (pl)	1979-03-31

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US4174445A (en)	1979-11-13	Preparation of arthropodicidally active substituted triazine-2,4-diones
US4048315A (en)	1977-09-13	Preparation of new 1,3-identically substituted-triazine-2,4-diones
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US4215132A (en)	1980-07-29	Combating arthropods with N,N-dimethyl-O-(3-substituted-pyrazol-5-yl)-carbamic acid esters
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US4093718A (en)	1978-06-06	O,O-dialkyl-5-halo-pyrimidin(2) yl-thionophosphoric acid esters
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