CA1041096A - Sulfonamides de dimethyl-1 carbamyl-3 alcoyle ramifie triazol-1,2,4 yl-5 (substitues en n) - Google Patents

Sulfonamides de dimethyl-1 carbamyl-3 alcoyle ramifie triazol-1,2,4 yl-5 (substitues en n)

Info

Publication number: CA1041096A
Authority: CA; Canada
Prior art keywords: triazol; dimethylcarbamyl; plants; butyl; tert
Prior art date: 1974-10-10
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

CA236,775A

Other languages

English (en)

Other versions

CA236775S (en

Inventor

Joel L. Kirkpatrick

William C. Doyle (Jr.)

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.)

Gulf Oil Corp

Original Assignee

Gulf Oil Corp

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.)

1974-10-10

Filing date

1975-09-30

Publication date

1978-10-24

1974-10-10 Priority claimed from US05/513,605 external-priority patent/US3973028A/en

1975-09-30 Application filed by Gulf Oil Corp filed Critical Gulf Oil Corp

1978-10-24 Application granted granted Critical

1978-10-24 Publication of CA1041096A publication Critical patent/CA1041096A/fr

Status Expired legal-status Critical Current

Links

229940124530 sulfonamide Drugs 0.000 title claims description 21
150000003456 sulfonamides Chemical class 0.000 title claims description 15
239000002917 insecticide Substances 0.000 title abstract description 5
241001124076 Aphididae Species 0.000 claims abstract description 26
231100001184 nonphytotoxic Toxicity 0.000 claims abstract description 23
238000000034 method Methods 0.000 claims description 26
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
150000001875 compounds Chemical class 0.000 claims description 23
125000000217 alkyl group Chemical group 0.000 claims description 9
125000000753 cycloalkyl group Chemical group 0.000 claims description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
VFFJXUQUPPJRDM-UHFFFAOYSA-N 3-cyclopropyl-5-[ethyl(methyl)sulfamoyl]-1-methyl-3H-1,2,4-triazole-2-carboxamide Chemical compound CN1N(C(N=C1S(=O)(=O)N(CC)C)C1CC1)C(N)=O VFFJXUQUPPJRDM-UHFFFAOYSA-N 0.000 claims 2
230000000749 insecticidal effect Effects 0.000 abstract description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
239000007787 solid Substances 0.000 description 10
239000000243 solution Substances 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 6
241000238631 Hexapoda Species 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
239000007788 liquid Substances 0.000 description 5
238000003786 synthesis reaction Methods 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
239000000203 mixture Substances 0.000 description 4
239000000843 powder Substances 0.000 description 4
239000007921 spray Substances 0.000 description 4
238000005507 spraying Methods 0.000 description 4
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
241000196324 Embryophyta Species 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
230000002824 aphicidal effect Effects 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
239000006185 dispersion Substances 0.000 description 3
239000003995 emulsifying agent Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000002736 nonionic surfactant Substances 0.000 description 3
-1 pivalyl thiosemicarbazide Chemical compound 0.000 description 3
239000002002 slurry Substances 0.000 description 3
ZVZQKNVMDKSGGF-UHFFFAOYSA-N 2-ethylsulfanylethoxy-dimethoxy-sulfanylidene-$l^{5}-phosphane Chemical compound CCSCCOP(=S)(OC)OC ZVZQKNVMDKSGGF-UHFFFAOYSA-N 0.000 description 2
BLBVSJIRDJWLQH-UHFFFAOYSA-N 5-tert-butyl-n,n-dimethyl-1h-1,2,4-triazole-3-sulfonamide Chemical compound CN(C)S(=O)(=O)C1=NNC(C(C)(C)C)=N1 BLBVSJIRDJWLQH-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
LVRCEUVOXCJYSV-UHFFFAOYSA-N CN(C)S(=O)=O Chemical compound CN(C)S(=O)=O LVRCEUVOXCJYSV-UHFFFAOYSA-N 0.000 description 2
229910020364 ClSO2 Inorganic materials 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
241000208236 Tropaeolaceae Species 0.000 description 2
235000004424 Tropaeolum majus Nutrition 0.000 description 2
125000000129 anionic group Chemical group 0.000 description 2
239000003945 anionic surfactant Substances 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
230000009885 systemic effect Effects 0.000 description 2
OZXIZRZFGJZWBF-UHFFFAOYSA-N 1,3,5-trimethyl-2-(2,4,6-trimethylphenoxy)benzene Chemical compound CC1=CC(C)=CC(C)=C1OC1=C(C)C=C(C)C=C1C OZXIZRZFGJZWBF-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
DRTQHJPVMGBUCF-UCVXFZOQSA-N 1-[(2s,3s,4s,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione Chemical compound O[C@H]1[C@H](O)[C@H](CO)O[C@@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UCVXFZOQSA-N 0.000 description 1
JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 1
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
241001425390 Aphis fabae Species 0.000 description 1
JNSAWGNVZMPYJI-UHFFFAOYSA-N CCNS(=O)=O Chemical compound CCNS(=O)=O JNSAWGNVZMPYJI-UHFFFAOYSA-N 0.000 description 1
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 1
244000045232 Canavalia ensiformis Species 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 1
YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
229910003844 NSO2 Inorganic materials 0.000 description 1
231100000674 Phytotoxicity Toxicity 0.000 description 1
241001061127 Thione Species 0.000 description 1
239000013504 Triton X-100 Substances 0.000 description 1
229920004890 Triton X-100 Polymers 0.000 description 1
240000001260 Tropaeolum majus Species 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
230000001055 chewing effect Effects 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
239000004927 clay Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000007865 diluting Methods 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
239000004491 dispersible concentrate Substances 0.000 description 1
239000004495 emulsifiable concentrate Substances 0.000 description 1
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 description 1
150000002431 hydrogen Chemical group 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
238000011005 laboratory method Methods 0.000 description 1
229920005610 lignin Polymers 0.000 description 1
239000000155 melt Substances 0.000 description 1
SHOJXDKTYKFBRD-UHFFFAOYSA-N mesityl oxide Natural products CC(C)=CC(C)=O SHOJXDKTYKFBRD-UHFFFAOYSA-N 0.000 description 1
HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
AHRZUJZFMANQHU-UHFFFAOYSA-N n,n-dimethyl-1h-1,2,4-triazole-5-sulfonamide Chemical compound CN(C)S(=O)(=O)C=1N=CNN=1 AHRZUJZFMANQHU-UHFFFAOYSA-N 0.000 description 1
UYDLBVPAAFVANX-UHFFFAOYSA-N octylphenoxy polyethoxyethanol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(OCCOCCOCCOCCO)C=C1 UYDLBVPAAFVANX-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000002689 soil Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
241000894007 species Species 0.000 description 1
238000003756 stirring Methods 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
239000010455 vermiculite Substances 0.000 description 1
229910052902 vermiculite Inorganic materials 0.000 description 1
235000019354 vermiculite Nutrition 0.000 description 1
239000004563 wettable powder Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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 to ring carbon atoms
- C07D249/12—Oxygen or sulfur atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Enzymes And Modification Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Lubricants (AREA)

CA236,775A 1974-10-10 1975-09-30 Sulfonamides de dimethyl-1 carbamyl-3 alcoyle ramifie triazol-1,2,4 yl-5 (substitues en n) Expired CA1041096A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US05/513,605 US3973028A (en)	1973-10-18	1974-10-10	1-Dimethylcarbamyl-3-branched alkyl-1,2,4-triazol-5-yl-(N-substituted) sulfonamides and use as insecticides

Publications (1)

Publication Number	Publication Date
CA1041096A true CA1041096A (fr)	1978-10-24

Family

ID=24043947

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA236,775A Expired CA1041096A (fr)	1974-10-10	1975-09-30	Sulfonamides de dimethyl-1 carbamyl-3 alcoyle ramifie triazol-1,2,4 yl-5 (substitues en n)

Country Status (8)

Country	Link
JP (1)	JPS5163941A (fr)
BR (1)	BR7506580A (fr)
CA (1)	CA1041096A (fr)
DE (1)	DE2545245A1 (fr)
ES (1)	ES441620A1 (fr)
FR (1)	FR2287172A1 (fr)
GB (1)	GB1463440A (fr)
IT (1)	IT1047749B (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0769009A1 (fr) *	1994-07-07	1997-04-23	Merrell Pharmaceuticals Inc.	Procede de preparation de 5-aryle-2,4-dialkyle-3h-1,2,4-triazole-3-thiones

1975
- 1975-09-30 CA CA236,775A patent/CA1041096A/fr not_active Expired
- 1975-10-02 GB GB4023775A patent/GB1463440A/en not_active Expired
- 1975-10-09 BR BR7506580A patent/BR7506580A/pt unknown
- 1975-10-09 ES ES441620A patent/ES441620A1/es not_active Expired
- 1975-10-09 IT IT5171775A patent/IT1047749B/it active
- 1975-10-09 FR FR7530901A patent/FR2287172A1/fr not_active Withdrawn
- 1975-10-09 JP JP12145275A patent/JPS5163941A/ja active Pending
- 1975-10-09 DE DE19752545245 patent/DE2545245A1/de active Pending

Also Published As

Publication number	Publication date
IT1047749B (it)	1980-10-20
GB1463440A (fr)	1977-02-02
FR2287172A1 (fr)	1976-05-07
BR7506580A (pt)	1976-08-17
ES441620A1 (es)	1977-04-01
DE2545245A1 (de)	1976-04-22
JPS5163941A (ja)	1976-06-02

Publication	Publication Date	Title
US5486610A (en)	1996-01-23	Pyrimidylbensulfonyl chloride compounds
US5206372A (en)	1993-04-27	Preparation of 2-chloropyridine derivatives
EP0173657A2 (fr)	1986-03-05	Compositions contenant des composés hétérocycliques et leur utilisation comme herbicides
US4038387A (en)	1977-07-26	1-dimethylcarbamyl-3-branched alkyl-1,2,4-triazol-5-yl-(n-substituted) sulfonamides and their use as insecticides
US3259623A (en)	1966-07-05	Process for preparing 2-(secondary amino)-halogenopyrimidines
US3973028A (en)	1976-08-03	1-Dimethylcarbamyl-3-branched alkyl-1,2,4-triazol-5-yl-(N-substituted) sulfonamides and use as insecticides
US3362960A (en)	1968-01-09	O-quinolyl-(8)-n-methyl carbamic acid esters
IL35271A (en)	1974-11-29	History of 1, 1, 1 - Trichloroethane, their preparation and use as pesticides
GB947485A (en)	1964-01-22	Improvements in or relating to heterocyclic amidophosphate compounds and combating noxious organisms thereby
EP0097013A2 (fr)	1983-12-28	Amines hétérocycliques fongicides
JPH07165737A (ja)	1995-06-27	除草性化合物
US3443926A (en)	1969-05-13	Herbicidal composition and method employing 3-benzyl hydantoins
US3560517A (en)	1971-02-02	Isoxazolidine carboxanilides
US4066765A (en)	1978-01-03	Arthropodicidal formamidines
US3937715A (en)	1976-02-10	Certain difluorodichloroethyldiazole compounds
US4728355A (en)	1988-03-01	Pyridazinylurea plant regulators
US3637729A (en)	1972-01-25	Perfluoroalkanesulfonamides n-substituted by heterocyclic groups
US3796708A (en)	1974-03-12	Substituted 1-phenyl-4-n-acetoacetata-mino-5-halopyridazone-(6)compounds
US3639663A (en)	1972-02-01	Thioalkylthiobenzothiazoles
US3953447A (en)	1976-04-27	Esterified 2-amino pyrimidine derivatives
US4578107A (en)	1986-03-25	Herbicidal imidazolidine-2-one derivatives
US4735650A (en)	1988-04-05	Pyridazinylurea N-oxide plant regulators
US3983172A (en)	1976-09-28	Bis-halogen carbonyl anilines and process for the production
CS262676B2 (en)	1989-03-14	Fungicide
IE43116B1 (en)	1980-12-17	Derivatives of 1,2,4-oxadiazolidine-3-one and pesticidal compositions containing them