IL41276A - Phenylimino dithiethane compounds - Google Patents
Phenylimino dithiethane compoundsInfo
- Publication number
- IL41276A IL41276A IL41276A IL4127673A IL41276A IL 41276 A IL41276 A IL 41276A IL 41276 A IL41276 A IL 41276A IL 4127673 A IL4127673 A IL 4127673A IL 41276 A IL41276 A IL 41276A
- Authority
- IL
- Israel
- Prior art keywords
- hydrogen
- dithietane
- compound
- halogen
- alkyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract 26
- -1 Phenylimino Chemical group 0.000 title claims abstract 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 22
- 239000001257 hydrogen Substances 0.000 claims abstract 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 14
- 229910052736 halogen Inorganic materials 0.000 claims abstract 14
- 150000002367 halogens Chemical class 0.000 claims abstract 14
- 125000000217 alkyl group Chemical group 0.000 claims abstract 8
- 150000002431 hydrogen Chemical class 0.000 claims abstract 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 5
- 125000004953 trihalomethyl group Chemical group 0.000 claims abstract 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract 4
- 125000000304 alkynyl group Chemical group 0.000 claims abstract 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract 4
- 125000005605 benzo group Chemical group 0.000 claims abstract 4
- 229910052760 oxygen Chemical group 0.000 claims abstract 4
- 239000001301 oxygen Chemical group 0.000 claims abstract 4
- 125000003342 alkenyl group Chemical group 0.000 claims abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 3
- 125000001424 substituent group Chemical group 0.000 claims abstract 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims 14
- 241001465754 Metazoa Species 0.000 claims 5
- VOWZNBNDMFLQGM-UHFFFAOYSA-N 2,5-dimethylaniline Chemical compound CC1=CC=C(C)C(N)=C1 VOWZNBNDMFLQGM-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- 239000002671 adjuvant Substances 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 239000011593 sulfur Substances 0.000 claims 3
- 239000002585 base Substances 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- BMIPMKQAAJKBKP-UHFFFAOYSA-N 2,4,5-Trimethylaniline Chemical compound CC1=CC(C)=C(N)C=C1C BMIPMKQAAJKBKP-UHFFFAOYSA-N 0.000 claims 1
- UQRLKWGPEVNVHT-UHFFFAOYSA-N 3,5-dichloroaniline Chemical compound NC1=CC(Cl)=CC(Cl)=C1 UQRLKWGPEVNVHT-UHFFFAOYSA-N 0.000 claims 1
- ZUVPLKVDZNDZCM-UHFFFAOYSA-N 3-chloro-2-methylaniline Chemical compound CC1=C(N)C=CC=C1Cl ZUVPLKVDZNDZCM-UHFFFAOYSA-N 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims 1
- 241001024304 Mino Species 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000005741 alkyl alkenyl group Chemical group 0.000 claims 1
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 230000003559 chemosterilizing effect Effects 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 239000012669 liquid formulation Substances 0.000 claims 1
- RRJRPRNKMYXEHM-UHFFFAOYSA-N n-(2,5-dimethylphenyl)-1,3-dithietan-2-imine Chemical compound CC1=CC=C(C)C(N=C2SCS2)=C1 RRJRPRNKMYXEHM-UHFFFAOYSA-N 0.000 claims 1
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- LRVFMDXQKMLGNF-UHFFFAOYSA-N dithietan-3-imine Chemical class N=C1SSC1 LRVFMDXQKMLGNF-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Abstract
1367862 Imino dithietanes AMERICAN CYANAMID CO 12 Jan 1973 [10 Feb 1972] 1838/73 Heading C2C [Also in Division A5] The invention comprises compounds of the formula where X, Y and Z are each H, halogen, hydroxy, R(M) n , phenoxy, monohalophenoxy, nitro, trihalomethyl, cyano, isothiocyano, carbo (C 1 -C 8 )- alkoxy, mono (C 1 -C 4 )-alkylamino, di (C 1 -C 4 )- alkyl amino or 1,3-dithietanylidene amino, R is C 1 -C 8 alkyl, C 5 -C 7 cycloalkyl, C 3 -C 8 alkenyl or C 3 -C 8 alkynyl, M is sulphur or oxygen, n is 0 or 1, and when two of X, Y and Z are taken together on adjacent carbon atoms they may form a benzo group, with the proviso that X, Y and Z cannot each be hydrogen, and that when one of X, Y and Z is halogen or (C 1 -C 8 )alkyl, at least one of the remaining substituents of X, Y and Z is other than hydrogen. The compounds are prepared by reacting together compounds of the formula and CH 2 Q 2 where M(+) is a cation and Q is a leaving group such as halogen.
[GB1367862A]
Claims (26)
1. A compound having the structure: wherein X, Y and Z each are hydrogen, halogen, hydroxy, R(M)n, phenoxy, monohalophenoxy , nitro, trihalomethyl , cyano, isothiocyano, carbloweralkoxy C^-Cg, dilower-alkylamino, monoloweralkylamino or 1 , 3-dithietanylidene- amino; R is alkyl C^-Cg, cycloalkyl C---Cy, alkenyl C^-Cg, or alkynyl C^-Cgj M is sulfur or oxygen; n is an integer of 0 or 1; and when two of X, Y and Z are taken together on adjacent carbons they may form a benzo group; with the proviso that X, Y and Z cannot each be hydrogen and that when one of X, Y and Z is halogen or lower alkyl, at least one of the remaining substituents of X, Y and Z is other than hydrogen.
2. A compound according to Claim 1 wherein X is hydrogen and Y represents a member selected from the group consisting of alkoxy C^-C^, hydroxy, alkyl- thio C^-C^, phenoxy, monohalophenoxy, nitro, trihalomethyl, cyano, isothiocyano, carbloweralkoxy C^-Cg, di- loweralkylamino, monoloweralkylamino and 1,3-dithiet- anylideneamino .
3. A compound according to Claim 1 where Z is hydrogen and X and Y represent members other than hydrogen .
4. A compound according to Claim 1 where X, Y and Z each represent members other than hydrogen.
5. S. A compound according to Claim 1 where Z is hydrogen and X and Y are halogen.
6. A compound according to Claim 1 where Z is hydrogen and X and Y are alkyl - C^.
7. A compound abcording to Claim 1 where Z is hydrogen, X is alkyl Cj - and Y is halogen.
8. A compound according to Claim 1 where X is phenoxy and Y and Z are hydrogen.
9. A compound according to Claim 1 where X is isothiocyano and Y and Z are hydrogen.
10. A compound according to Claim 1 where X is nitro, Y is halogen and Z is hydrogen.
11. A compound according to Claim 1 selected from the group consisting of 2-p_-chloro-o-methylpheny1itnino-1,3-dithietane, 2-p_-bromo-o-methylphenfclimino-1,3-dithietane, 2-(2,5-dimethylphenyl mino)-1,3-dithie tane, 2-(2*4,5-trimethylphenylimino)-1,3-dithietane, 2-m-chloro-^methyl-phenyimino-1,3-dithietane, 2-o,£-dimethylphenylimino-l,3-dithietane, 2-o, -did\lorophenylimino-I ,3-dithietane, 2-o,ra-dich1oropheny1imino-1,3-dithie tane,2-o-raethoxyphenylimino-1,3-dithietane.
12. A method for the control of Ixodides comprising, applying to adult female Ixodides a chemo-sterilizing amount of a compound having the structure: X wherein X, Y and Z each represent a member selected from the group consisting of hydrogen, halogen, hydroxy, R(M)n, phenoxy, monohalophenoxy , nitro, trihalomethyl , cyano, isothiocyano , carbloweralkoxy C-^-Cg, dilower-alkylamino, monoloweralkylamino, 1 , 3-dithietanylidene-amino; R Is a member selected from alkyl cyclo-alkyl C^-C^, alkenyl C3-Cg, alkynyl C^-Cg; M is sulfur or oxygen; n is an integer of 0 or 1; and when two of X, Y and Z are taken together on adjacent carbons they may form a benzo group.
13. A method according to Claim 1 where Z is hydrogen, X is halogen and Y is alkyl of one to four carbon atoms.
14. A method according to Claim 12 where Z is hydrogen and X and Y are halogen.
15. A method according to Claim 12 where Z is hydrogen and X and Y are alkyl of one to four carbon atoms .
16. A method according to Claim 12 wherein said compound is applied at a concentration between about 250 ppm. and 2500 ppm.
17. · A method for protecting warm-blooded animals against attack by Ixodides comprising, topically treating said warm-blooded animals with an effective amount of a compound according to Claim 12.
18. A method according to Claim 17 wherein said compound is topically applied to said animal as a liquid formulation containing from between about 250 ppm of said compound in an inert agricultural adjuvant. 1.9.
19. A method according to Claim 18 wherein said compound is selected from the group consisting of: 2-p_-chloro-o-methylphenylimino-l , 3-dithietane , 2-p_--bromo-o-methylphenylimino-1 , 3-dithietane , 2-o-methy1- phenylimino-1, 3-dithietane , 2-(2 ,5-dimethylphenylimino )--1 , 3-dIthietane , 2- ( 2 , 4 , 5-trimeth lphenylimino )-l , 3--dlthietane , 2-rn-chloro-o-methylphenylimino-l ,3-dithi-etane, 2-o,p_-dimethylphenylimino-l, 3-dithietane, 2-o,p_--dichlorophenylimino-1 , 3-dithietane , 2-o ,m-dichloro-phenylimino-1 , 3-dithietane , 2-o-methoxyphenylimlno-l , 3--dithietane .
20. A composition useful in protecting warm--blooded animals against attack by Ixodides comprising an effective amount of a compound of Claim 12 as an active ingredient therein, in admixture with an inert agricultural adjuvant.
21. A method for the preparation of a composition useful in the protection of warm-blooded animals against attack by Ixodides comprising admixing an effective amount of a compound of Claim 12 with an inert agricultural adjuvant.
22. A process for the preparation of compounds of the following formula : wherein X, Y and Z each are hydrogen, halogen, hydroxy, R(M)n, phenoxy, monohalophenoxy , nitro, trihalomethyl , cyano, isothiocyano, carbloweralkoxy C^-Cg, dilower-alkylamino, monoloweralkylamino, or 1,3-dithietanyl-ideneamino; R is alkyl alkenyl C3-Cg, or alkynyl is sulfur or oxygen; n is an integer of 0 or 1; and when two of X, Y and Z are taken 41276/2 together on adjacent carbons they may form a benzo group; with the proviso that X, Y, and Z cannot each be hydrogen and than when one of X, Y and Z is halogen or lower alkyl, at least one of the remaining substituents of X, Y and Z is other than hydrogen, characterized by reacting a compound of the following formula: X wherein X, Y and Z are as defined above, with a compound of formula QLJQJ, wherein Q is halogen, in th"* presence of a base.
23. A process according to Claim 22 wherein the base is an alkali metal hydroxide, a carbonate, a bicarbonate, or a tertiary amine.
24. A process according to Claims 22 and 23 wherein the reaction is carried out in an inert organic solvent.
25. A process according to Claim 24 wherein the organic solvent is dimethylformamide, methanol or 1,2-di-methoxyethane.
26. A process according to Claim 22 wherein the starting material is derived from: £-ch1oro-o-meth 1aniline, £=bromo-o-methylaniline, 2,5-dimethylaniline, 2,4,5-trimethyl-aniline, m-chloro-o-methylaniline, o,p_-dimethylaniline, , jf-dichloroaniline, o,m-dichloroaniline and o-methoxyaniline. S. HOROWITZ § CO. AGENTS FOR APPLICANTS
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US22527872A | 1972-02-10 | 1972-02-10 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL41276A0 IL41276A0 (en) | 1973-03-30 |
| IL41276A true IL41276A (en) | 1976-07-30 |
Family
ID=22844272
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL41276A IL41276A (en) | 1972-02-10 | 1973-01-11 | Phenylimino dithiethane compounds |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS5312975B2 (en) |
| AR (1) | AR195698A1 (en) |
| AU (1) | AU474093B2 (en) |
| BE (1) | BE795204A (en) |
| BR (1) | BR7300942D0 (en) |
| CH (1) | CH582691A5 (en) |
| CS (1) | CS178420B2 (en) |
| DE (1) | DE2305517C3 (en) |
| FR (1) | FR2171314B1 (en) |
| GB (1) | GB1367862A (en) |
| IL (1) | IL41276A (en) |
| IT (1) | IT977028B (en) |
| KE (1) | KE2606A (en) |
| MY (1) | MY7600138A (en) |
| NL (1) | NL7300766A (en) |
| ZA (1) | ZA73129B (en) |
| ZM (1) | ZM673A1 (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3933851A (en) * | 1974-02-06 | 1976-01-20 | American Cyanamid Company | Preparation of aromatic 2-imino-1,3-dithietanes |
| US4471571A (en) * | 1978-11-15 | 1984-09-18 | Monsanto Company | Substituted 2-imino-1,3-dithio and 1,3-oxathio heterocyclic compounds as herbicidal antidotes |
| US4542609A (en) * | 1978-11-15 | 1985-09-24 | Monsanto Co. | Substituted 2-imino-1,3-dithio and 1,3-oxathio heterocyclic compounds as herbicidal antidotes |
| JPH0314355U (en) * | 1989-06-27 | 1991-02-13 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3484455A (en) * | 1967-04-21 | 1969-12-16 | American Cyanamid Co | 2-imino-1,3-dithietanes and processes for their preparation |
-
0
- BE BE795204D patent/BE795204A/en unknown
-
1973
- 1973-01-08 ZA ZA730129A patent/ZA73129B/en unknown
- 1973-01-09 AU AU50907/73A patent/AU474093B2/en not_active Expired
- 1973-01-11 IL IL41276A patent/IL41276A/en unknown
- 1973-01-12 GB GB183873A patent/GB1367862A/en not_active Expired
- 1973-01-18 NL NL7300766A patent/NL7300766A/xx not_active Application Discontinuation
- 1973-01-19 ZM ZM6/73*UA patent/ZM673A1/en unknown
- 1973-01-24 IT IT47870/73A patent/IT977028B/en active
- 1973-01-24 AR AR246270A patent/AR195698A1/en active
- 1973-02-05 DE DE2305517A patent/DE2305517C3/en not_active Expired
- 1973-02-06 CS CS869A patent/CS178420B2/cs unknown
- 1973-02-07 BR BR73942A patent/BR7300942D0/en unknown
- 1973-02-08 FR FR7304512A patent/FR2171314B1/fr not_active Expired
- 1973-02-08 CH CH181373A patent/CH582691A5/xx not_active IP Right Cessation
- 1973-02-10 JP JP1699673A patent/JPS5312975B2/ja not_active Expired
-
1976
- 1976-03-08 KE KE2606*UA patent/KE2606A/en unknown
- 1976-12-30 MY MY138/76A patent/MY7600138A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ZM673A1 (en) | 1973-09-21 |
| KE2606A (en) | 1976-04-02 |
| GB1367862A (en) | 1974-09-25 |
| FR2171314A1 (en) | 1973-09-21 |
| DE2305517A1 (en) | 1973-08-16 |
| BR7300942D0 (en) | 1973-09-13 |
| FR2171314B1 (en) | 1978-08-04 |
| NL7300766A (en) | 1973-08-14 |
| MY7600138A (en) | 1976-12-31 |
| AR195698A1 (en) | 1973-10-31 |
| AU5090773A (en) | 1974-07-11 |
| CH582691A5 (en) | 1976-12-15 |
| DE2305517B2 (en) | 1977-11-24 |
| CS178420B2 (en) | 1977-09-15 |
| IL41276A0 (en) | 1973-03-30 |
| ZA73129B (en) | 1973-09-26 |
| IT977028B (en) | 1974-09-10 |
| DE2305517C3 (en) | 1978-08-17 |
| JPS5312975B2 (en) | 1978-05-06 |
| BE795204A (en) | 1973-08-09 |
| JPS4887024A (en) | 1973-11-16 |
| AU474093B2 (en) | 1976-07-15 |
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