CA1180726A - Oxime de cyclobutanone - Google Patents

Oxime de cyclobutanone

Info

Publication number: CA1180726A
Authority: CA; Canada
Prior art keywords: oxime; formula; cyclobutanone; compound; hydrogen
Prior art date: 1980-04-24
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

CA000443984A

Other languages

English (en)

Inventor

Laurenz Gsell

Jean-Claude Gehret

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.)

1980-04-24

Filing date

1983-12-21

Publication date

1985-01-08

1981-04-22 Priority claimed from CA000375961A external-priority patent/CA1175442A/fr

1983-12-21 Application filed by Ciba Geigy Investments Ltd filed Critical Ciba Geigy Investments Ltd

1983-12-21 Priority to CA000443984A priority Critical patent/CA1180726A/fr

1985-01-08 Application granted granted Critical

1985-01-08 Publication of CA1180726A publication Critical patent/CA1180726A/fr

Status Expired legal-status Critical Current

Links

YDYCXDWUKJSHMI-UHFFFAOYSA-N n-cyclobutylidenehydroxylamine Chemical compound ON=C1CCC1 YDYCXDWUKJSHMI-UHFFFAOYSA-N 0.000 title claims abstract description 5
150000001875 compounds Chemical class 0.000 claims abstract description 32
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
239000001257 hydrogen Chemical group 0.000 claims abstract description 11
229910052736 halogen Inorganic materials 0.000 claims abstract description 9
150000002367 halogens Chemical group 0.000 claims abstract description 9
238000000034 method Methods 0.000 claims abstract description 8
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 7
238000002360 preparation method Methods 0.000 claims abstract description 7
150000002431 hydrogen Chemical group 0.000 claims abstract 4
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract 3
-1 2,3,3-Trimethyl-cyclobutanone oxime Chemical compound 0.000 claims description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
150000002923 oximes Chemical class 0.000 claims description 8
239000000460 chlorine Chemical group 0.000 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 3
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 2
SHQSVMDWKBRBGB-UHFFFAOYSA-N cyclobutanone Chemical compound O=C1CCC1 SHQSVMDWKBRBGB-UHFFFAOYSA-N 0.000 claims description 2
CHCWVNBIEIVSAC-UHFFFAOYSA-N CC1(C)CC(=NO)C1Cl Chemical compound CC1(C)CC(=NO)C1Cl CHCWVNBIEIVSAC-UHFFFAOYSA-N 0.000 claims 1
IIVONNCHOQXTDM-UHFFFAOYSA-N CSC1(C)C(=NO)CC1(C)C Chemical compound CSC1(C)C(=NO)CC1(C)C IIVONNCHOQXTDM-UHFFFAOYSA-N 0.000 claims 1
HIMFDMSUMYIUFP-UHFFFAOYSA-N NC(O)=O.ON=C1CCC1 Chemical class NC(O)=O.ON=C1CCC1 HIMFDMSUMYIUFP-UHFFFAOYSA-N 0.000 abstract description 3
239000000543 intermediate Substances 0.000 abstract description 2
239000000575 pesticide Substances 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
241000196324 Embryophyta Species 0.000 description 11
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
241000238631 Hexapoda Species 0.000 description 7
239000000243 solution Substances 0.000 description 6
235000013601 eggs Nutrition 0.000 description 5
239000000203 mixture Substances 0.000 description 5
241000952611 Aphis craccivora Species 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
241000256250 Spodoptera littoralis Species 0.000 description 4
125000003545 alkoxy group Chemical group 0.000 description 4
241000254175 Anthonomus grandis Species 0.000 description 3
241001425390 Aphis fabae Species 0.000 description 3
241000721621 Myzus persicae Species 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000004657 carbamic acid derivatives Chemical class 0.000 description 3
230000000749 insecticidal effect Effects 0.000 description 3
HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 3
241000894007 species Species 0.000 description 3
238000005507 spraying Methods 0.000 description 3
230000009885 systemic effect Effects 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
241000238876 Acari Species 0.000 description 2
241001124076 Aphididae Species 0.000 description 2
229920000742 Cotton Polymers 0.000 description 2
241000219146 Gossypium Species 0.000 description 2
240000002024 Gossypium herbaceum Species 0.000 description 2
235000004341 Gossypium herbaceum Nutrition 0.000 description 2
241000256244 Heliothis virescens Species 0.000 description 2
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
241000607479 Yersinia pestis Species 0.000 description 2
230000001276 controlling effect Effects 0.000 description 2
239000012043 crude product Substances 0.000 description 2
239000004495 emulsifiable concentrate Substances 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
241001427556 Anoplura Species 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
241000254173 Coleoptera Species 0.000 description 1
241000255925 Diptera Species 0.000 description 1
241000345386 Fabia Species 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
241000256257 Heliothis Species 0.000 description 1
241001466007 Heteroptera Species 0.000 description 1
241001495069 Ischnocera Species 0.000 description 1
241000256602 Isoptera Species 0.000 description 1
241000255777 Lepidoptera Species 0.000 description 1
241000258916 Leptinotarsa decemlineata Species 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
241000721623 Myzus Species 0.000 description 1
UQHBYVLFWNUFIB-UHFFFAOYSA-N N-(3,3-dimethyl-2-methylsulfanylcyclobutylidene)hydroxylamine methylcarbamic acid Chemical compound CNC(O)=O.CSC1C(=NO)CC1(C)C UQHBYVLFWNUFIB-UHFFFAOYSA-N 0.000 description 1
241000244206 Nematoda Species 0.000 description 1
241000238814 Orthoptera Species 0.000 description 1
244000046052 Phaseolus vulgaris Species 0.000 description 1
229920005372 Plexiglas® Polymers 0.000 description 1
241001415024 Psocoptera Species 0.000 description 1
241000258242 Siphonaptera Species 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
241000256248 Spodoptera Species 0.000 description 1
241001414989 Thysanoptera Species 0.000 description 1
241000219873 Vicia Species 0.000 description 1
240000006677 Vicia faba Species 0.000 description 1
235000010749 Vicia faba Nutrition 0.000 description 1
241001414985 Zygentoma Species 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
150000001448 anilines Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
230000018109 developmental process Effects 0.000 description 1
238000010410 dusting Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000005538 encapsulation Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
230000012447 hatching Effects 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
244000005700 microbiome Species 0.000 description 1
RRIIQGFIWZEMNE-UHFFFAOYSA-N n-(3,3-dimethyl-2-methylsulfanylcyclobutylidene)hydroxylamine Chemical compound CSC1C(=NO)CC1(C)C RRIIQGFIWZEMNE-UHFFFAOYSA-N 0.000 description 1
231100000194 ovacidal Toxicity 0.000 description 1
230000003151 ovacidal effect Effects 0.000 description 1
230000003032 phytopathogenic effect Effects 0.000 description 1
239000002574 poison Substances 0.000 description 1
231100000614 poison Toxicity 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
230000008092 positive effect Effects 0.000 description 1
239000001103 potassium chloride Substances 0.000 description 1
235000011164 potassium chloride Nutrition 0.000 description 1
238000000746 purification Methods 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000002689 soil Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
235000020354 squash Nutrition 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
244000045561 useful plants Species 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
239000004563 wettable powder Substances 0.000 description 1

Landscapes

Agricultural Chemicals And Associated Chemicals (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA000443984A 1980-04-24 1983-12-21 Oxime de cyclobutanone Expired CA1180726A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000443984A CA1180726A (fr)	1980-04-24	1983-12-21	Oxime de cyclobutanone

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
CH3170/80-1		1980-04-24
CH317080		1980-04-24
CH1007/81-9		1981-02-16
CH100781		1981-02-16
CA000375961A CA1175442A (fr)	1980-04-24	1981-04-22	Oxime carbamates de cyclobutanone, preparation et utilisation comme pesticides chez les animaux et les plantes
CA000443984A CA1180726A (fr)	1980-04-24	1983-12-21	Oxime de cyclobutanone

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000375961A Division CA1175442A (fr)	1980-04-24	1981-04-22	Oxime carbamates de cyclobutanone, preparation et utilisation comme pesticides chez les animaux et les plantes

Publications (1)

Publication Number	Publication Date
CA1180726A true CA1180726A (fr)	1985-01-08

Family

ID=27426301

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000443984A Expired CA1180726A (fr)	1980-04-24	1983-12-21	Oxime de cyclobutanone

Country Status (1)

Country	Link
CA (1)	CA1180726A (fr)

1983
- 1983-12-21 CA CA000443984A patent/CA1180726A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2002-01-08	MKEX	Expiry

Publication	Publication Date	Title
CA1137496A (fr)	1982-12-14	Procede industriel d'obtention de 1,n,n- dimethylcarbamoyl-3(5)-alkyl-5(3)- alkylthioalkylthio-1,2,4-triazoles, substances contenant de ces produits et applications pesticides
CA1258076A (fr)	1989-08-01	Phenylhydrazines, leur production, et leur emploi pour la repression des insectes
CA1180726A (fr)	1985-01-08	Oxime de cyclobutanone
IL42564A (en)	1977-06-30	O-(substituted alkoxy)phenyl carbamates ther preparation and pesticidal compositions containing them
KR890000369B1 (ko)	1989-03-14	S-메틸 n-[{n-메틸-n-(n, n-이치환된 아미노설페닐)카바모일}옥시]티오아세트아미데이트 유도체의 제조방법
US4734433A (en)	1988-03-29	Isothioureas and insecticidal use thereof
JPH05112556A (ja)	1993-05-07	殺虫性ピラゾリン類
CA1170662A (fr)	1984-07-10	Derives de carbanate, leur preparation, et insecticides qui les renferment
US4323574A (en)	1982-04-06	Cis and trans isomers of α-methyl(6-phenoxy-2-pyridyl)methyl-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylates and derivatives thereof
US3962316A (en)	1976-06-08	Carbamate
US4348414A (en)	1982-09-07	Cyclobutanone oxime carbamates, and use thereof in pest control
US3476490A (en)	1969-11-04	Methods of using particular carbamic acid esters for insecticidal and acaricidal purposes
CN87104091A (zh)	1988-12-21	新的苯甲酰脲
US4160843A (en)	1979-07-10	Novel amidines
US4472429A (en)	1984-09-18	N-(3-Trimethylstannylpropyl)carbamates and use thereof in pest control
US4140784A (en)	1979-02-20	Novel thiazolidines
US4150122A (en)	1979-04-17	Substituted carbamates
CA1139771A (fr)	1983-01-18	Derives du (n-methylcarbamoyl-phenoxy)-n',n'',n''- trialkyl-uree)-n-n'-sulfure, procede de production, compose les contenant a titre d'ingredients actifs et utilisation pour larepression des insectes nuisibles
US4163791A (en)	1979-08-07	2-Phenyliminothiazoline compounds
US3455912A (en)	1969-07-15	Benzodioxan-n-methylcarbamates
CA1151190A (fr)	1983-08-02	N-(2-isobutyronitrilesulfenyl)-n-methyl-carbamates, procedes de fabrication et emploi dans des pesticides
US4971994A (en)	1990-11-20	Thioureas
US4064250A (en)	1977-12-20	Insecticidal benzodioxol-4-yl carbamates and intermediates thereof
CA1204768A (fr)	1986-05-20	N-(benzamidosulfenyl)-n-methylcarbamates; methode de preparation et utilisation comme pesticides
CA2016731A1 (fr)	1990-11-16	Derives hydrazyde