IL28545A - Fungicidal 1-acyl-benzimidazoline derivatives - Google Patents

Fungicidal 1-acyl-benzimidazoline derivatives

Info

Publication number: IL28545A
Authority: IL; Israel
Prior art keywords: active; fungi; formula; carbon; fungicidal
Prior art date: 1966-10-04

Application number

IL28545A

Other languages

English (en)

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.)

1966-10-04

Filing date

1967-08-22

Publication date

1972-05-30

1967-08-22 Application filed by Bayer Ag filed Critical Bayer Ag

1972-05-30 Publication of IL28545A publication Critical patent/IL28545A/en

Links

230000000855 fungicidal effect Effects 0.000 title claims description 8
150000001875 compounds Chemical class 0.000 claims description 27
241000233866 Fungi Species 0.000 claims description 13
239000000203 mixture Substances 0.000 claims description 13
238000000034 method Methods 0.000 claims description 10
239000003085 diluting agent Substances 0.000 claims description 8
239000007788 liquid Substances 0.000 claims description 7
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
229910052799 carbon Inorganic materials 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 6
239000007787 solid Substances 0.000 claims description 5
206010039509 Scab Diseases 0.000 claims description 4
239000004480 active ingredient Substances 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
230000003032 phytopathogenic effect Effects 0.000 claims description 3
241000221785 Erysiphales Species 0.000 claims description 2
125000003342 alkenyl group Chemical group 0.000 claims description 2
125000004414 alkyl thio group Chemical group 0.000 claims description 2
239000003795 chemical substances by application Substances 0.000 claims description 2
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
125000005017 substituted alkenyl group Chemical group 0.000 claims description 2
206010061217 Infestation Diseases 0.000 description 11
241000220225 Malus Species 0.000 description 5
-1 alkenyl radical Chemical class 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
241000196324 Embryophyta Species 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
229920000151 polyglycol Polymers 0.000 description 4
239000010695 polyglycol Substances 0.000 description 4
239000007921 spray Substances 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
125000002877 alkyl aryl group Chemical group 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
238000009472 formulation Methods 0.000 description 3
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical compound COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
230000010933 acylation Effects 0.000 description 2
238000005917 acylation reaction Methods 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
125000001033 ether group Chemical group 0.000 description 2
230000002464 fungitoxic effect Effects 0.000 description 2
239000000155 melt Substances 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
239000002904 solvent Substances 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
HCVANKFEUQUUGJ-UHFFFAOYSA-N C(=O)(Cl)Cl.[C] Chemical compound C(=O)(Cl)Cl.[C] HCVANKFEUQUUGJ-UHFFFAOYSA-N 0.000 description 1
241000022563 Rema Species 0.000 description 1
241000579741 Sphaerotheca <fungi> Species 0.000 description 1
239000005864 Sulphur Substances 0.000 description 1
241000607479 Yersinia pestis Species 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
125000005036 alkoxyphenyl group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
150000001556 benzimidazoles Chemical class 0.000 description 1
238000009835 boiling Methods 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
VWWMOACCGFHMEV-UHFFFAOYSA-N dicarbide(2-) Chemical compound [C-]#[C-] VWWMOACCGFHMEV-UHFFFAOYSA-N 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 1
238000010410 dusting Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000011081 inoculation Methods 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
238000002156 mixing Methods 0.000 description 1
150000005181 nitrobenzenes Chemical class 0.000 description 1
XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
125000002924 primary amino group Chemical class [H]N([H])* 0.000 description 1
239000000047 product Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
238000005507 spraying Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000002699 waste material Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1

Classifications

- 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
- C07D235/26—Oxygen 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

Landscapes

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

IL28545A 1966-10-04 1967-08-22 Fungicidal 1-acyl-benzimidazoline derivatives IL28545A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DEF0050354		1966-10-04

Publications (1)

Publication Number	Publication Date
IL28545A true IL28545A (en)	1972-05-30

Family

ID=7103733

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL28545A IL28545A (en)	1966-10-04	1967-08-22	Fungicidal 1-acyl-benzimidazoline derivatives

Country Status (11)

Country	Link
US (1)	US3499085A (de)
AT (1)	AT275967B (de)
BE (1)	BE704581A (de)
CH (1)	CH492396A (de)
DE (1)	DE1542886A1 (de)
DK (1)	DK120267B (de)
ES (1)	ES345664A1 (de)
FR (1)	FR1555642A (de)
GB (1)	GB1152531A (de)
IL (1)	IL28545A (de)
NL (1)	NL6713436A (de)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4205077A (en) *	1977-04-12	1980-05-27	Ciba-Geigy Corporation	Benzimidazole sulphides as anthelmintic agents
CH640548A5 (de) *	1979-08-28	1984-01-13	Ciba Geigy Ag	Flammwidrige kunststofformmasse.
GB8313321D0 (en) *	1983-05-14	1983-06-22	Ciba Geigy Ag	Preparation of mercaptan substituted carboxylic acids
US4728741A (en) *	1985-01-08	1988-03-01	Smithkline Beckman Corporation	1-substituted-2-mercapto benzimidazole compounds and intermediates
US5457180A (en) *	1989-08-04	1995-10-10	Biochem Pharma Inc.	Methods for producing linear thiopeptides using an amino acid ortho amino thioanilide compound
US5138061A (en) *	1989-08-04	1992-08-11	Biochem Pharma Inc.	Thioacylating reagents
US5371102A (en) *	1992-03-11	1994-12-06	University Of Hawaii	Compositions and methods of inhibiting thyroid activity
KR100281826B1 (ko) *	1998-04-21	2001-02-15	박호군	N,n-디아실이미다졸론 유도체를 이용한 아민의 아실화 방법
CN102816121B (zh) *	2011-06-12	2016-03-23	西北农林科技大学农药研究所	1-酰基-3-异丙烯基苯并咪唑酮衍生物作为抗细菌药物的用途
CN102503896A (zh) *	2011-10-25	2012-06-20	西北农林科技大学	甲基丙烯酰基苯并咪唑（硫）酮衍生物及其作为抗菌药物的用途
WO2013059984A1 (zh) *	2011-10-25	2013-05-02	西北农林科技大学	甲基丙烯酰基苯并咪唑（硫）酮衍生物及其作为抗菌药物的用途
CN103664791A (zh) *	2012-09-12	2014-03-26	西北农林科技大学农药研究所	1-酰基苯并咪唑酮衍生物及其作为农用杀菌剂的用途
CN104922116B (zh) *	2014-03-23	2020-08-11	上海诗丹德生物技术有限公司	甲基丙烯酰基苯并咪唑酮衍生物的用途
CN112047889A (zh) *	2018-11-30	2020-12-08	华南农业大学	一种n-二氟甲基杂芳烃并咪唑硫脲衍生物的制备方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH448109A (de) *	1964-01-25	1967-12-15	Bayer Ag	Verfahren zur Herstellung von Thiocarbamidsäure-S-ester
DE1215162B (de) *	1964-12-16	1966-04-28	Bayer Ag	Verfahren zur Herstellung von N, N'-disubstituierten Imidazolonen

1966
- 1966-10-04 DE DE19661542886 patent/DE1542886A1/de active Pending
1967
- 1967-08-22 IL IL28545A patent/IL28545A/en unknown
- 1967-08-22 CH CH1175667A patent/CH492396A/de not_active IP Right Cessation
- 1967-08-30 GB GB39712/67A patent/GB1152531A/en not_active Expired
- 1967-09-27 US US671112A patent/US3499085A/en not_active Expired - Lifetime
- 1967-10-02 BE BE704581D patent/BE704581A/xx unknown
- 1967-10-02 ES ES345664A patent/ES345664A1/es not_active Expired
- 1967-10-03 DK DK491367AA patent/DK120267B/da unknown
- 1967-10-03 NL NL6713436A patent/NL6713436A/xx unknown
- 1967-10-04 FR FR1555642D patent/FR1555642A/fr not_active Expired
- 1967-10-04 AT AT899067A patent/AT275967B/de active

Also Published As

Publication number	Publication date
AT275967B (de)	1969-11-10
CH492396A (de)	1970-06-30
FR1555642A (de)	1969-01-31
US3499085A (en)	1970-03-03
DK120267B (da)	1971-05-03
NL6713436A (de)	1968-04-05
GB1152531A (en)	1969-05-21
BE704581A (de)	1968-04-02
DE1542886A1 (de)	1970-05-14
ES345664A1 (es)	1968-11-16

Publication	Publication Date	Title
IL28545A (en)	1972-05-30	Fungicidal 1-acyl-benzimidazoline derivatives
IL31302A (en)	1972-08-30	N-tritylimidazoles,their preparation and use for combatting fungi
US3501578A (en)	1970-03-17	Fungicidal composition containing phenyl - mercaptomethane-sulfonamide and method of using the same
US3624091A (en)	1971-11-30	Oxime-o-carbonic acid esters
US3395225A (en)	1968-07-30	Quinolyl carbamic acid ester fungicides for combatting phytopathogenic fungi
US3780089A (en)	1973-12-18	Substituted ureidophenyl thioureas
US3843715A (en)	1974-10-22	Amidophenylisothioureas
IL33362A (en)	1972-07-26	Omega-cyanoalkylcarbamylbenzimidazoles,their production and pesticidal and antibacterial compositions containing them
US2971884A (en)	1961-02-14	Method for the control of fungal organisms
US2875126A (en)	1959-02-24	New esters of 5-acyl-8-hydroxyquinolines and their use for the control of fungi
US3562292A (en)	1971-02-09	N-substituted phthalimides
US3766243A (en)	1973-10-16	Ureidophenylisothioureas
US3597480A (en)	1971-08-03	(n-trihalomethylthio-n-trifluoromethyl-amino)-benzamides
US2839446A (en)	1958-06-17	New pyrimidine derivatives
US3770769A (en)	1973-11-06	2-imino-5-alkylamino-1,3-dithianes
PL69661B1 (de)	1973-08-31
US3711503A (en)	1973-01-16	Substituted carbonyl-carbamidyl-benzimidazole-2-yl-carbamic acid esters
FI73422B (fi)	1987-06-30	1-(trihalogenmetylsulfenyl)-4-aryl-1, 2,4-triazolidin-5-oner och dessa innehaollande fungicider och foerfarande foer bekaempning av svampar med dem.
US4339461A (en)	1982-07-13	N-Substituted 3-nitro-benzylamines
PL110797B1 (en)	1980-07-31	Fungicide
US4560694A (en)	1985-12-24	Fungicidal alkylene(cycloalkylene)-bis-heterocyclyl-biguanides
US4551458A (en)	1985-11-05	Quinazolines and fungicidal compositions thereof
US3816532A (en)	1974-06-11	Ketoxime carbamate pesticides
US3458639A (en)	1969-07-29	Nitrophenyl carbamic acid esters as molluscicides
US4049820A (en)	1977-09-20	Substituted urazole and thiourazole compounds as agricultural fungicidal agents