GB1263138A - Episulphides of unsaturated acids and alcohols, derivatives thereof and the use thereof as pesticides - Google Patents
Episulphides of unsaturated acids and alcohols, derivatives thereof and the use thereof as pesticidesInfo
- Publication number
- GB1263138A GB1263138A GB47141/69A GB4714169A GB1263138A GB 1263138 A GB1263138 A GB 1263138A GB 47141/69 A GB47141/69 A GB 47141/69A GB 4714169 A GB4714169 A GB 4714169A GB 1263138 A GB1263138 A GB 1263138A
- Authority
- GB
- United Kingdom
- Prior art keywords
- cis
- alkyl
- trans
- hydrogen
- epoxy
- Prior art date
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/32—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by aldehydo- or ketonic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/38—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D303/40—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals by ester radicals
- C07D303/42—Acyclic compounds having a chain of seven or more carbon atoms, e.g. epoxidised fats
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/38—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D303/46—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals by amide or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D331/00—Heterocyclic compounds containing rings of less than five members, having one sulfur atom as the only ring hetero atom
- C07D331/02—Three-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
1,263,138. Episulphides of unsaturated acids and alcohols; derivatives thereof. F. HOFFMANN-LA ROCHE & CO. A.G. 25 Sept., 1969 [27 Sept., 1968], No. 47141/69. Heading C2C. Novel episulphides of the formula in which A and B are hydrogen or together represent a double bond or a sulphur bridge, R is hydrogen or C 1-6 alkyl, R<SP>5</SP> is hydrogen or methyl, Y is cyano, carboxyl, C 1-6 alkoxycarbonyl, phenyloxycarbonyl or benzyloxycarbonyl (in which either phenyl moiety may be substituted by hydroxy, C 1-6 alkyl, C 1-6 alkoxy or halogen), a group -CONR<SP>2</SP>R<SP>3</SP> (in which R<SP>2</SP> and R<SP>3</SP> are each hydrogen, C 1-6 alkyl or together complete a 5- or 6-membered heterocycle which may contain O, S or N as an additional hetero atom), a group -CH 2 OR<SP>4</SP>, in which R<SP>4</SP> is hydrogen, C 1-6 alkyl, C 1-6 alkanoyl, C 6-10 aroyl, benzoyl substituted by C 1-6 alkyl, amino-C 1-6 alkyl, or a phenyl or benzyl group (which phenyl or benzyl group may be substituted by C 1-6 alkyl, C 1-6 alkoxy, methylenedioxy, C 1-6 alkoxycarbonyl, C 1-6 -alkanoyl, C 6-10 aroyl, C 1-6 alkylbenzoyl, phenyl-C 1-6 -alkyl or halogen), and n is 0 or 1, are prepared (a) by reacting a ketone of the formula with a phosphonate of the formula in the presence of a base and an organic solvent, where R<SP>6</SP> is cyano, -COOR<SP>1</SP> or -CONR<SP>1</SP>R<SP>3</SP>, in which COOR<SP>1</SP> is an esterified carboxyl value of Y above, and R<SP>7</SP> and R<SP>8</SP> are C 1-6 alkoxy or phenoxy optionally substituted by C 1-6 alkoxy, nitro or halogen, or (b) episulphidizing a compound of the formula in which A<SP>1</SP> is hydrogen or hydroxy, B<SP>1</SP> is hydrogen or halogen or A<SP>1</SP> and B<SP>1</SP> together represent a double bond or a sulphur bridge, D is hydroxy and E is halogen or D and E together represent an oxygen bridge, and in either case, if desired, hydrolysing any ester formed. Episulphidizing agents for use in (b) include thiourea, thiocyanates, thiobarbituric acid, thioamides and thiosulphates. If Compound IV is a halohydrin and thiourea is used, an isothiouronium salt is obtained which yields the epithio compound on treatment with a base. The final products can be converted to other values of Y by conventional methods, e.g. the free acid, via the acid halide, yields the amides or esters, the alcohol via the metal salts to the ethers or acylated alcohols. Examples describe the preparation of epithio derivatives of 3,7,11-alkyl 2,6,10-dodecatrienyl and tridecatrienyl compounds. 10,11-Epoxy-3,7,11-trimethyl-1-[(p-benzylphenyl)oxy]2-cis/trans,6-cis-dodecadiene is obtained by reacting 2-cis/trans-6-cis-farnesyl bromide with p-benzylphenol to form p-benzylphenyl 3,7,11-trimethyl-2-cis/trans,6-cis,10-dodecatrienyl ether which is halogenated with N-bromosuccinimide to obtain 3-bromo-2,6,10-trimethyl-12- [(p-benzylphenyl)oxy]-6-cis,10-cis/trans-dodecadien-2-ol which yields the required dodecadiene on treatment with NaOMe. 10,11-Epoxy-3,7,10,11- tetramethyl-dodeca-2,6-dienoic acid ethyl ester is obtained by epoxidizing 6,9,10-trimethylundeca- 5,9-dien-2-one to 9,10-epoxy-6,9,10-trimethylundeca-5-en-2-one which is condensed with diethyl phosphoniacetic acid ethyl ester. 9,10- Epithio-6,10-dimethyl-undec-5-trans-en-2-one is obtained by treating the corresponding 9,10 epoxy ketone with thiourea and Na 2 CO 3 . 9,10- Epithio - 6,9,10 - trimethylundec - 5 - cis/transen-2-one is obtained similarly. 10,11-Epoxy- 3,7,11 - trimethyldodeca - 2 - cis/trans, 6 - transdienenitrile is obtained by condensing 9,10- epoxy - 6,10 - dimethylundec - 5 - trans - en - 2- one with diethyl phosphonoacetonitrile. The novel episulphides upset the hormone balance of pests such as insects and are used in conventional forms to protect foodstuffs, textiles and plants from such pests.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH1452268A CH543229A (en) | 1968-09-27 | 1968-09-27 | Pesticides |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1263138A true GB1263138A (en) | 1972-02-09 |
Family
ID=4401536
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB47141/69A Expired GB1263138A (en) | 1968-09-27 | 1969-09-25 | Episulphides of unsaturated acids and alcohols, derivatives thereof and the use thereof as pesticides |
Country Status (15)
Country | Link |
---|---|
AT (1) | AT299611B (en) |
BE (1) | BE739353A (en) |
BR (1) | BR6912700D0 (en) |
CA (1) | CA938298A (en) |
CH (1) | CH543229A (en) |
DE (1) | DE1948164A1 (en) |
DK (1) | DK130346B (en) |
ES (1) | ES371941A1 (en) |
FR (1) | FR2030045A1 (en) |
GB (1) | GB1263138A (en) |
IE (1) | IE33819B1 (en) |
IL (1) | IL33010A (en) |
NL (1) | NL6914481A (en) |
SE (1) | SE367827B (en) |
TR (1) | TR17216A (en) |
-
1968
- 1968-09-27 CH CH1452268A patent/CH543229A/en not_active IP Right Cessation
-
1969
- 1969-09-17 IL IL33010A patent/IL33010A/en unknown
- 1969-09-18 CA CA062350A patent/CA938298A/en not_active Expired
- 1969-09-23 DE DE19691948164 patent/DE1948164A1/en active Pending
- 1969-09-24 NL NL6914481A patent/NL6914481A/xx unknown
- 1969-09-24 DK DK506669AA patent/DK130346B/en unknown
- 1969-09-25 BE BE739353D patent/BE739353A/xx unknown
- 1969-09-25 BR BR212700/69A patent/BR6912700D0/en unknown
- 1969-09-25 GB GB47141/69A patent/GB1263138A/en not_active Expired
- 1969-09-26 ES ES371941A patent/ES371941A1/en not_active Expired
- 1969-09-26 SE SE13309/69A patent/SE367827B/xx unknown
- 1969-09-26 FR FR6932890A patent/FR2030045A1/fr not_active Withdrawn
- 1969-09-26 TR TR17216A patent/TR17216A/en unknown
- 1969-09-26 AT AT913069A patent/AT299611B/en not_active IP Right Cessation
- 1969-09-26 IE IE1340/69A patent/IE33819B1/en unknown
Also Published As
Publication number | Publication date |
---|---|
BR6912700D0 (en) | 1973-01-04 |
NL6914481A (en) | 1970-04-01 |
DE1948164A1 (en) | 1970-04-02 |
FR2030045A1 (en) | 1970-10-30 |
TR17216A (en) | 1976-05-02 |
CA938298A (en) | 1973-12-11 |
CH543229A (en) | 1973-10-31 |
ES371941A1 (en) | 1971-11-16 |
DK130346B (en) | 1975-02-10 |
DK130346C (en) | 1975-07-14 |
SE367827B (en) | 1974-06-10 |
AT299611B (en) | 1972-06-26 |
IE33819B1 (en) | 1974-11-13 |
IL33010A (en) | 1974-10-22 |
IL33010A0 (en) | 1969-11-30 |
BE739353A (en) | 1970-03-25 |
IE33819L (en) | 1970-03-27 |
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