CA1218372A - Derives de la n-(2-nitrophenyl)-2-aminopyrimidine - Google Patents

Derives de la n-(2-nitrophenyl)-2-aminopyrimidine

Info

Publication number: CA1218372A
Authority: CA; Canada
Prior art keywords: halogen; formula; substituted; hydrogen; compound
Prior art date: 1985-06-19
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

Application number

CA000484416A

Other languages

English (en)

Inventor

Adolf Hubele

Helmut Zondler

Peter Riebli

Wolfgang Eckhardt

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Novartis AG

Original Assignee

Ciba Geigy Investments Ltd

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.)

1985-06-19

Filing date

1985-06-19

Publication date

1987-02-24

1985-06-19 Application filed by Ciba Geigy Investments Ltd filed Critical Ciba Geigy Investments Ltd

1985-06-19 Priority to CA000484416A priority Critical patent/CA1218372A/fr

1987-02-24 Application granted granted Critical

1987-02-24 Publication of CA1218372A publication Critical patent/CA1218372A/fr

Status Expired legal-status Critical Current

Links

ATEGONGXGQUUJT-UHFFFAOYSA-N 1-(2-nitrophenyl)-2h-pyrimidin-2-amine Chemical class NC1N=CC=CN1C1=CC=CC=C1[N+]([O-])=O ATEGONGXGQUUJT-UHFFFAOYSA-N 0.000 title abstract description 3
150000001875 compounds Chemical class 0.000 claims abstract description 96
229910052736 halogen Inorganic materials 0.000 claims abstract description 38
-1 nitro, cyano, thiocyano Chemical group 0.000 claims abstract description 38
239000001257 hydrogen Substances 0.000 claims abstract description 26
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 26
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 13
125000000217 alkyl group Chemical group 0.000 claims abstract description 12
238000000034 method Methods 0.000 claims abstract description 12
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 11
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 9
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 8
239000001301 oxygen Substances 0.000 claims abstract description 8
229910052760 oxygen Inorganic materials 0.000 claims abstract description 8
229910052717 sulfur Chemical group 0.000 claims abstract description 8
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 7
125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 7
239000011593 sulfur Chemical group 0.000 claims abstract description 7
125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims abstract description 6
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 5
125000005842 heteroatom Chemical group 0.000 claims abstract description 5
229920006395 saturated elastomer Polymers 0.000 claims abstract description 5
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 3
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract description 3
150000002431 hydrogen Chemical class 0.000 claims abstract 4
125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims abstract 2
239000000460 chlorine Chemical group 0.000 claims description 183
150000002367 halogens Chemical group 0.000 claims description 34
241000233866 Fungi Species 0.000 claims description 26
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 26
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 23
238000002360 preparation method Methods 0.000 claims description 9
230000003032 phytopathogenic effect Effects 0.000 claims description 8
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 7
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
241000607479 Yersinia pestis Species 0.000 claims description 5
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 5
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 4
244000005700 microbiome Species 0.000 claims description 4
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
125000004076 pyridyl group Chemical group 0.000 claims description 4
125000001424 substituent group Chemical group 0.000 claims description 4
239000011737 fluorine Substances 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
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 claims description 3
125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 2
241000235349 Ascomycota Species 0.000 claims description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
MYZHNDSXZGVZHK-UHFFFAOYSA-N NC1N=C(Cl)C(Cl)=C(Cl)N1C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1C(F)(F)F Chemical compound NC1N=C(Cl)C(Cl)=C(Cl)N1C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1C(F)(F)F MYZHNDSXZGVZHK-UHFFFAOYSA-N 0.000 claims description 2
CKWHZNSJURMKOX-UHFFFAOYSA-N NC1N=C(Cl)C=C(Cl)N1C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1C(F)(F)F Chemical compound NC1N=C(Cl)C=C(Cl)N1C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1C(F)(F)F CKWHZNSJURMKOX-UHFFFAOYSA-N 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
150000003230 pyrimidines Chemical class 0.000 claims description 2
241000221198 Basidiomycota Species 0.000 claims 1
UYOBLLKCQUMILZ-UHFFFAOYSA-N CC(=C)OC1=C(Br)C(Cl)=NC(N)N1C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1C(F)(F)F Chemical compound CC(=C)OC1=C(Br)C(Cl)=NC(N)N1C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1C(F)(F)F UYOBLLKCQUMILZ-UHFFFAOYSA-N 0.000 claims 1
239000000203 mixture Substances 0.000 abstract description 59
239000004480 active ingredient Substances 0.000 abstract description 12
125000005843 halogen group Chemical group 0.000 abstract description 6
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230000000361 pesticidal effect Effects 0.000 abstract description 3
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RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
238000009472 formulation Methods 0.000 description 18
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
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238000012360 testing method Methods 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
239000000725 suspension Substances 0.000 description 9
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
239000007787 solid Substances 0.000 description 8
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XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
239000004563 wettable powder Substances 0.000 description 8
125000004432 carbon atom Chemical group C* 0.000 description 7
239000000969 carrier Substances 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
239000004094 surface-active agent Substances 0.000 description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
239000005995 Aluminium silicate Substances 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 6
239000002671 adjuvant Substances 0.000 description 6
235000012211 aluminium silicate Nutrition 0.000 description 6
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
235000014113 dietary fatty acids Nutrition 0.000 description 6
239000000194 fatty acid Substances 0.000 description 6
229930195729 fatty acid Natural products 0.000 description 6
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 6
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VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
239000008096 xylene Substances 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
239000002202 Polyethylene glycol Substances 0.000 description 5
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical group OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 5
150000002170 ethers Chemical class 0.000 description 5
238000011156 evaluation Methods 0.000 description 5
239000008187 granular material Substances 0.000 description 5
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150000003839 salts Chemical class 0.000 description 5
239000000243 solution Substances 0.000 description 5
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
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150000001338 aliphatic hydrocarbons Chemical class 0.000 description 4
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
230000003115 biocidal effect Effects 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
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230000003449 preventive effect Effects 0.000 description 1
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235000019355 sepiolite Nutrition 0.000 description 1
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235000019333 sodium laurylsulphate Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
PYODKQIVQIVELM-UHFFFAOYSA-M sodium;2,3-bis(2-methylpropyl)naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CC(C)C)C(CC(C)C)=CC2=C1 PYODKQIVQIVELM-UHFFFAOYSA-M 0.000 description 1
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239000007858 starting material Substances 0.000 description 1
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238000006467 substitution reaction Methods 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
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239000004546 suspension concentrate Substances 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
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235000013616 tea Nutrition 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
BGQMOFGZRJUORO-UHFFFAOYSA-M tetrapropylammonium bromide Chemical compound [Br-].CCC[N+](CCC)(CCC)CCC BGQMOFGZRJUORO-UHFFFAOYSA-M 0.000 description 1
FBEVECUEMUUFKM-UHFFFAOYSA-M tetrapropylazanium;chloride Chemical compound [Cl-].CCC[N+](CCC)(CCC)CCC FBEVECUEMUUFKM-UHFFFAOYSA-M 0.000 description 1
GKXDJYKZFZVASJ-UHFFFAOYSA-M tetrapropylazanium;iodide Chemical compound [I-].CCC[N+](CCC)(CCC)CCC GKXDJYKZFZVASJ-UHFFFAOYSA-M 0.000 description 1
AJZGFFKDLABHDD-UHFFFAOYSA-N thiazinane Chemical compound C1CCSNC1 AJZGFFKDLABHDD-UHFFFAOYSA-N 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000004670 unsaturated fatty acids Chemical class 0.000 description 1
235000021122 unsaturated fatty acids Nutrition 0.000 description 1
244000045561 useful plants Species 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

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Plural Heterocyclic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

CA000484416A 1985-06-19 1985-06-19 Derives de la n-(2-nitrophenyl)-2-aminopyrimidine Expired CA1218372A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000484416A CA1218372A (fr)	1985-06-19	1985-06-19	Derives de la n-(2-nitrophenyl)-2-aminopyrimidine

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000484416A CA1218372A (fr)	1985-06-19	1985-06-19	Derives de la n-(2-nitrophenyl)-2-aminopyrimidine

Publications (1)

Publication Number	Publication Date
CA1218372A true CA1218372A (fr)	1987-02-24

Family

ID=4130752

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000484416A Expired CA1218372A (fr)	1985-06-19	1985-06-19	Derives de la n-(2-nitrophenyl)-2-aminopyrimidine

Country Status (1)

Country	Link
CA (1)	CA1218372A (fr)

1985
- 1985-06-19 CA CA000484416A patent/CA1218372A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2005-06-19	MKEX	Expiry

Publication	Publication Date	Title
US4694009A (en)	1987-09-15	Pesticidal compositions
US4659363A (en)	1987-04-21	N-(2-nitrophenyl)-2-aminopyrimidine derivatives, the preparation and use thereof
CA1254560A (fr)	1989-05-23	Derives de n-(2-nitrophenyl)-4-aminopyridine; preparation et utilisation
CA1218369A (fr)	1987-02-24	Derives de la n-(2-nitrophenyl)-4-aminopyrimidine
AU592802B2 (en)	1990-01-25	Substituted 3-phenyl-cyanopyrrole derivatives
AU622640B2 (en)	1992-04-16	Heterocyclic substituted dihaloisonicotinicacidamides for protecting plants against microorganisms
US6262058B1 (en)	2001-07-17	Pyrimidin-4-one derivatives as pesticide
CA1305483C (fr)	1992-07-21	Microbicides
US5468751A (en)	1995-11-21	Aminopyrimidine derivatives as microbicides, insecticides and acaricides
US4840662A (en)	1989-06-20	N-(2-nitrophenyl)-5-aminopyrimidine derivatives and useful for controlling harmful micro-organisms
AU616176B2 (en)	1991-10-24	Substituted isonicotinoylpyridinylhydrazine derivatives, the preparation thereof, compositions containing them and their use in the protection of plants against attack by harmful microorganisms
CA1218372A (fr)	1987-02-24	Derives de la n-(2-nitrophenyl)-2-aminopyrimidine
US4402731A (en)	1983-09-06	Herbicidally active novel substituted tetrahydropyrimidinones
US5163996A (en)	1992-11-17	Sulfonylureas
US5374639A (en)	1994-12-20	Benzotriazolesulfonic acid derivatives as microbicides
US5322853A (en)	1994-06-21	Microbicidal benzotriazole compounds
US5120741A (en)	1992-06-09	Microbicides
CA2085311A1 (fr)	1993-06-17	Microbicides
CA1213894A (fr)	1986-11-12	Composes d'organotin
IE912134A1 (en)	1992-01-01	Microbicides
IL91556A (en)	1994-01-25	Substituted 2-aminopyrimidine derivatives, their preparation and their use as pesticides
GB2127820A (en)	1984-04-18	Microbicidal imidazolidine-2,4- dione derivatives
WO1995001975A1 (fr)	1995-01-19	Derives de pyrimidin-4-ylaminomethylquinoleine utilises comme pesticides
IE910652A1 (en)	1991-08-28	Microbicides
WO1994018173A1 (fr)	1994-08-18	Derives de l'acide sulfonique de benzimidazole en tant que microbicides