IL27824A - Substituted 2-aminobenzimidazoles - Google Patents

Substituted 2-aminobenzimidazoles

Info

Publication number: IL27824A
Authority: IL; Israel
Prior art keywords: methyl; benzimidazolecarbamate; compounds; plants; alkyl
Prior art date: 1966-05-06

Application number

IL2782467A

Other languages

English (en)

Original Assignee

Du Pont

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.)

1966-05-06

Filing date

1967-04-19

Publication date

1971-04-28

1967-04-19 Application filed by Du Pont filed Critical Du Pont

1971-04-28 Publication of IL27824A publication Critical patent/IL27824A/en

Links

JWYUFVNJZUSCSM-UHFFFAOYSA-N 2-aminobenzimidazole Chemical class C1=CC=C2NC(N)=NC2=C1 JWYUFVNJZUSCSM-UHFFFAOYSA-N 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 104
239000000203 mixture Substances 0.000 claims description 80
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 68
-1 methoxy, ethoxy Chemical group 0.000 claims description 43
239000004480 active ingredient Substances 0.000 claims description 37
125000004432 carbon atom Chemical group C* 0.000 claims description 15
125000000217 alkyl group Chemical group 0.000 claims description 14
230000000855 fungicidal effect Effects 0.000 claims description 13
238000000034 method Methods 0.000 claims description 13
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
239000000417 fungicide Substances 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
WEYSQARHSRZNTC-UHFFFAOYSA-N 1h-benzimidazol-2-ylcarbamic acid Chemical compound C1=CC=C2NC(NC(=O)O)=NC2=C1 WEYSQARHSRZNTC-UHFFFAOYSA-N 0.000 claims description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
229910052736 halogen Chemical group 0.000 claims description 6
150000002367 halogens Chemical group 0.000 claims description 6
239000012948 isocyanate Substances 0.000 claims description 6
125000000753 cycloalkyl group Chemical group 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
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125000003342 alkenyl group Chemical group 0.000 claims description 3
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
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XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
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JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
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150000002576 ketones Chemical class 0.000 description 1
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UWRBYRMOUPAKLM-UHFFFAOYSA-L lead arsenate Chemical compound [Pb+2].O[As]([O-])([O-])=O UWRBYRMOUPAKLM-UHFFFAOYSA-L 0.000 description 1
239000000787 lecithin Substances 0.000 description 1
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238000011068 loading method Methods 0.000 description 1
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
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WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
235000013372 meat Nutrition 0.000 description 1
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QRXNHSNKHRRFMK-UHFFFAOYSA-N methyl n-[1-(propylcarbamoyl)benzimidazol-2-yl]carbamate Chemical compound C1=CC=C2N(C(=O)NCCC)C(NC(=O)OC)=NC2=C1 QRXNHSNKHRRFMK-UHFFFAOYSA-N 0.000 description 1
JVJUWCMBRUMDDQ-UHFFFAOYSA-N methylmercuric dicyanamide Chemical compound C[Hg]N=C(N)NC#N JVJUWCMBRUMDDQ-UHFFFAOYSA-N 0.000 description 1
STSGKERZHAYXMQ-UHFFFAOYSA-M methylmercury(1+);acetate Chemical compound C[Hg]OC(C)=O STSGKERZHAYXMQ-UHFFFAOYSA-M 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000003595 mist Substances 0.000 description 1
239000003607 modifier Substances 0.000 description 1
125000001421 myristyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
APVPOHHVBBYQAV-UHFFFAOYSA-N n-(4-aminophenyl)sulfonyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 APVPOHHVBBYQAV-UHFFFAOYSA-N 0.000 description 1
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
OKQIEBVRUGLWOR-UHFFFAOYSA-N n-naphthalen-1-ylacetamide Chemical compound C1=CC=C2C(NC(=O)C)=CC=CC2=C1 OKQIEBVRUGLWOR-UHFFFAOYSA-N 0.000 description 1
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150000002790 naphthalenes Chemical class 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Chemical compound CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
239000002736 nonionic surfactant Substances 0.000 description 1
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125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
150000002889 oleic acids Chemical class 0.000 description 1
150000002923 oximes Chemical class 0.000 description 1
LCCNCVORNKJIRZ-UHFFFAOYSA-N parathion Chemical compound CCOP(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 LCCNCVORNKJIRZ-UHFFFAOYSA-N 0.000 description 1
RLBIQVVOMOPOHC-UHFFFAOYSA-N parathion-methyl Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C=C1 RLBIQVVOMOPOHC-UHFFFAOYSA-N 0.000 description 1
235000020232 peanut Nutrition 0.000 description 1
235000021017 pears Nutrition 0.000 description 1
230000035515 penetration Effects 0.000 description 1
LKPLKUMXSAEKID-UHFFFAOYSA-N pentachloronitrobenzene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl LKPLKUMXSAEKID-UHFFFAOYSA-N 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
XEBWQGVWTUSTLN-UHFFFAOYSA-M phenylmercury acetate Chemical compound CC(=O)O[Hg]C1=CC=CC=C1 XEBWQGVWTUSTLN-UHFFFAOYSA-M 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
239000002367 phosphate rock Substances 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
150000003014 phosphoric acid esters Chemical class 0.000 description 1
235000021018 plums Nutrition 0.000 description 1
229940068918 polyethylene glycol 400 Drugs 0.000 description 1
229920000056 polyoxyethylene ether Polymers 0.000 description 1
229920001451 polypropylene glycol Polymers 0.000 description 1
229920000036 polyvinylpyrrolidone Chemical class 0.000 description 1
239000001267 polyvinylpyrrolidone Chemical class 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
235000012015 potatoes Nutrition 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000011268 retreatment Methods 0.000 description 1
JUVIOZPCNVVQFO-HBGVWJBISA-N rotenone Chemical compound O([C@H](CC1=C2O3)C(C)=C)C1=CC=C2C(=O)[C@@H]1[C@H]3COC2=C1C=C(OC)C(OC)=C2 JUVIOZPCNVVQFO-HBGVWJBISA-N 0.000 description 1
JUVIOZPCNVVQFO-UHFFFAOYSA-N rotenone Natural products O1C2=C3CC(C(C)=C)OC3=CC=C2C(=O)C2C1COC1=C2C=C(OC)C(OC)=C1 JUVIOZPCNVVQFO-UHFFFAOYSA-N 0.000 description 1
239000004576 sand Substances 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
HIEHAIZHJZLEPQ-UHFFFAOYSA-M sodium;naphthalene-1-sulfonate Chemical class [Na+].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HIEHAIZHJZLEPQ-UHFFFAOYSA-M 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
238000003756 stirring Methods 0.000 description 1
229960005322 streptomycin Drugs 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
238000004381 surface treatment Methods 0.000 description 1
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239000000375 suspending agent Substances 0.000 description 1
230000008961 swelling Effects 0.000 description 1
229940104261 taurate Drugs 0.000 description 1
UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
KPHOBSTVDZCCAU-UHFFFAOYSA-N tetracyclo[6.4.0.02,4.05,7]dodeca-1(12),2(4),5(7),8,10-pentaene Chemical compound C1=CC=CC2=C3CC3=C(C3)C3=C21 KPHOBSTVDZCCAU-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
230000005945 translocation Effects 0.000 description 1
150000003626 triacylglycerols Chemical class 0.000 description 1
235000020234 walnut Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6503—Five-membered rings
- C07F9/6506—Five-membered rings having the nitrogen atoms in positions 1 and 3
- C07F9/65068—Five-membered rings having the nitrogen atoms in positions 1 and 3 condensed with carbocyclic rings or carbocyclic ring systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/22—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms directly attached to ring nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/28—Sulfur atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/30—Nitrogen atoms not forming part of a nitro radical
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/30—Nitrogen atoms not forming part of a nitro radical
- C07D235/32—Benzimidazole-2-carbamic acids, unsubstituted or substituted; Esters thereof; Thio-analogues thereof
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

IL2782467A 1966-05-06 1967-04-19 Substituted 2-aminobenzimidazoles IL27824A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US54803466A	1966-05-06	1966-05-06

Publications (1)

Publication Number	Publication Date
IL27824A true IL27824A (en)	1971-04-28

Family

ID=24187140

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL2782467A IL27824A (en)	1966-05-06	1967-04-19	Substituted 2-aminobenzimidazoles

Country Status (8)

Country	Link
CY (2)	CY631A (fi)
DO (1)	DOP1967001364A (fi)
ES (1)	ES339900A1 (fi)
FI (1)	FI46581C (fi)
GB (2)	GB1193461A (fi)
GR (1)	GR34500B (fi)
IL (1)	IL27824A (fi)
NL (1)	NL136613C (fi)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4078070A (en) *	1973-01-16	1978-03-07	Hoechst Aktiengesellschaft	Fungicidal dispersions
OA05041A (fr)	1974-07-15	1980-12-31	Rhone Poulenc Ind	Nouvelles compositions fongicides.
US4857541A (en) *	1986-08-07	1989-08-15	Canadian Patents And Development Limited/Societe Canadienne Des Brevets Et D'exploitation Limitee	Substituted benzimidazole fungicide

1967
- 1967-04-19 IL IL2782467A patent/IL27824A/en unknown
- 1967-04-27 GR GR670134500A patent/GR34500B/el unknown
- 1967-04-27 ES ES339900A patent/ES339900A1/es not_active Expired
- 1967-05-02 DO DO1967001364A patent/DOP1967001364A/es unknown
- 1967-05-05 FI FI130067A patent/FI46581C/fi active
- 1967-05-05 GB GB2105667A patent/GB1193461A/en not_active Expired
- 1967-05-05 NL NL6706331A patent/NL136613C/xx active
- 1967-05-05 GB GB88770A patent/GB1193462A/en not_active Expired
1972
- 1972-02-14 CY CY63172A patent/CY631A/xx unknown
- 1972-02-14 CY CY63072A patent/CY630A/xx unknown

Also Published As

Publication number	Publication date
NL136613C (fi)	1973-01-16
DOP1967001364A (es)	1972-03-29
CY630A (en)	1972-02-14
GB1193462A (en)	1970-06-03
GB1193461A (en)	1970-06-03
FI46581B (fi)	1973-01-31
NL6706331A (fi)	1967-11-07
FI46581C (fi)	1973-05-08
CY631A (en)	1972-02-14
ES339900A1 (es)	1968-09-16
GR34500B (el)	1968-05-16

Publication	Publication Date	Title
US3631176A (en)	1971-12-28	Carbamoyl substituted 2-aminobenzimidazoles
NO168008B (no)	1991-09-23	En likestroemselektromagnet, spesielt for en elektrisk bryteranordning.
DE1620175A1 (de)	1970-05-21	Fungicides Mittel
US3639633A (en)	1972-02-01	Substituted o-carbamylhydroxamate pesticides
US3882247A (en)	1975-05-06	Fungicidal nitro organic sulfur compounds
US3427388A (en)	1969-02-11	Esters of benzimidazolecarbamic acid as mite ovicides
US3662069A (en)	1972-05-09	Alkyl 1-(n-substituted thiocarbamoyl)-2-benzimidazolecarbamates as fungicides and mite ovicides
US3636005A (en)	1972-01-18	Acyl substituted 2-benzimidazolecarbamates
US3836569A (en)	1974-09-17	Alkyl 4-(o-(substituted methyleneamino)phenyl)-3-thioallophanates
US3958007A (en)	1976-05-18	Pesticidal alkyl 4-(0-(substituted methyleneamine)-phenyl)-3-thioallophanates
IL27824A (en)	1971-04-28	Substituted 2-aminobenzimidazoles
US3641048A (en)	1972-02-08	Alkyl 1 - (substituted alkylideneaminooxycarbonyl) - 2 -benzimidazolecarbamates
US4018926A (en)	1977-04-19	Alkyl 4-[o-(substituted methyleneamino)-phenyl]-3-thioallophanate miticides and fungicides
US3726908A (en)	1973-04-10	Substituted o-carbamylhydroxamates
US3655657A (en)	1972-04-11	2 1 4-benzothiadiazine-3-carbamic acid esters
US3950391A (en)	1976-04-13	Alkyl 4-(o-aminophenyl)-3-thioallophanates
US3562282A (en)	1971-02-09	Transition metal complexes of substituted 2 -benzimidazolecarbamic acid,alkyl esters and their preparation
US3927069A (en)	1975-12-16	Alkyl 4-{8 o-(substituted amino)phenyl{9 -3-thioallophanates
US3789122A (en)	1974-01-29	Fungicidal compositions of transition metal complexes of substituted 2-benzimidazolecarbamic acid, alkyl esters
US3970668A (en)	1976-07-20	Dialkyl 1,1'-(optionally substituted hydrocarbylenebiscarbamoyl)bis(2-benzimidazolecarbamates)
DE1745784C3 (de)	1974-09-05	Fungicide und/oder Milbenovicide
US3595870A (en)	1971-07-27	Metal complexes of 2-benzimidazolecarbamic acid esters
US4010278A (en)	1977-03-01	Compositions of alkyl 4-[o-(substituted amino)phenyl]-3-thioallophanates and methods of use
US4011213A (en)	1977-03-08	Alkyl 4-[o-(substituted methyleneamino)phenyl]-3-thioallophanates
US3705939A (en)	1972-12-12	Fungicidal compositions and methods utilizing metal complexes