IL42156A - Substituted butenoic acid derivatives their manufacture and use as pesticides - Google Patents

Substituted butenoic acid derivatives their manufacture and use as pesticides

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Publication number
IL42156A
IL42156A IL42156A IL4215673A IL42156A IL 42156 A IL42156 A IL 42156A IL 42156 A IL42156 A IL 42156A IL 4215673 A IL4215673 A IL 4215673A IL 42156 A IL42156 A IL 42156A
Authority
IL
Israel
Prior art keywords
methyl
carbonyl
formula
alkyl
phenoxy
Prior art date
Application number
IL42156A
Other versions
IL42156A0 (en
Original Assignee
Ciba Geigy 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.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=27174895&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=IL42156(A) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Priority claimed from CH701172A external-priority patent/CH566709A5/en
Priority claimed from CH1425572A external-priority patent/CH578317A5/en
Priority claimed from CH456773A external-priority patent/CH578825A5/en
Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag
Publication of IL42156A0 publication Critical patent/IL42156A0/en
Publication of IL42156A publication Critical patent/IL42156A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
    • C07C45/515—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an acetalised, ketalised hemi-acetalised, or hemi-ketalised hydroxyl group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/255—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
    • C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
    • C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine Compounds (AREA)

Abstract

1422181 Aromatic derivatives of but-2- enoic acid CIBA-GEIGY AG 9 May 1973 [10 May 1972 29 Sept 1972 29 March 1973] 22213/73 Heading C2C The invention comprises a compound of Formula I wherein R 1 represents a cyclohexyl or cyclohexyloxy group or a group of Formula Ia in which n represents 0 or 1, Y represents an oxygen atom or a group of formula and R 6 represents a hydrogen or halogen atom or a C 1-5 alkyl or alkoxy group and R 7 represents a C 1-3 alkyl, formyl or acetyl group; R 2 represents a hydrogen or halogen atom, CH 3 or C 2 H 5 ; R 3 represents H, CH 3 or C 2 H 5 ; R 4 represents a hydrogen atom or a C 1-3 alkyl group; R<SP>5</SP> represents a carboxyl, (C 1-5 alkoxy)carbonyl, unsubstituted or halosubstituted (C 3-5 alkenyloxy)carbonyl, (C 3-5 alkynyloxy)carbonyl, cyclohexyloxycarbonyl, phenoxycarbonyl or cyano group or a group of Formula Ib in which R 8 represents a hydrogen atom or a C 1-5 alkyl, C 3-5 alkenyl, or C 3-5 alkynyl group and R 9 represents a C 1-5 alkyl, C 3-5 alkenyl or C 3-5 alkynyl group or R 8 and R 9 together with their attached nitrogen represent a saturated heterocyclic group having 5 or 6 ring atoms which atoms may comprise an oxygen, sulphur or further nitrogen atom; Z represents -O-, -NH-, -NR 7 - or -CH(R 10 )O- the latter being carbon linked to the phenyl nucleus and R 10 being H or C 1-3 alkyl. The compounds of Formula I may be prepared by reacting (a) a compound of Formula II in the presence of a base with a compound of Formula III (III) X-CHR 3 -CR 4 = CH-R 5 in which R 1 to R 5 and z are as defined above and x-halogen, (b) a compound of Formula V with a compound of Formula VIII R 1 to R 5 and z being as defined above, R 11 represents a C 1-5 alkyl, phenyl or p-chlorophenyl group and Me represents an alkali or alkaline earth metal of valency n, (c) a compound of Formula IX (i) in the presence of an acid catalyst with a compound of formula R 12 OH or (ii) in the presence of a base with a compound of formula R 12 X wherein R 12 represents a C 1-5 alkyl, C 3 to C 5 alkenyl, C 3 to C 5 alkynyl or cyclohexyl group and X is halogen to obtain compounds of Formula I in which R 1 to R 4 and z are as defined above and R 5 represents a (C 1-5 alkoxy)carbonyl, (C 3-5 alkenyloxy)carbonyl, (C 3-5 alkynyloxy)- carbonyl or cyclohexyloxycarbonyl groups or (d) a compound of Formula I in which Y and/or Z represents -NH- with an alkylating or acylating agent to obtain compounds of Formula I in which Y and/or Z represents -NR 7 - R 7 being as defined above other than hydrogen. 1 - [4 - Benzylphenoxy]propan - 2 - one, 1 - [4 - phenoxyphenoxy] - propan - 2 - one, 1 - [4 - benzoylphenoxy]propan - 2 - one and 2 - [4 - phenoxyphenoxy] - butan - 3 - one are prepared by hydrolysis of their dimethyl ketals. 1 - [4 - Benzylphenoxy] - propan - 2 - ondimethylketal is prepared by reacting 4- benzylpropargyloxybenzene with a mixture of HgO, CCl 3 CO 2 H, BF 3 .(C 2 H 5 ) 2 O and CH 3 OH. Pesticidal compositions comprise a compound of Formula I together with a solid extender, a solid extender and a surface active agent or a liquid diluent and a surface active agent. [GB1422181A]

Claims (1)

1. CLAIMS 1. Compounds of the general formula he , - R 5 -C16H0-, I6 R5 the -CH- group being bonded to the phenyl nucleus, g represents hydrogen, C-^-C^-alkyl, R^ represents -C00H, ^ ( C, -C -alkoxy) carbonyl, ( C-, -C---alkenyl0xy) carbonyl, ( C^ -C^-alkinyloxy) carbonyl, cyclohexyloxycarbonyl, phenoxycarbonyl, ( C^-C^ haloalkenyloxy) carbonyl, the cyano group, a carbamoyl group which is mono- or disubstituted "-by it being possible for the substituents of the carbamoyl group together with the nitrogen atom to which they are bonded to form a saturated 5- or 6-membered heterocyclic ring which 'can contain in addition an oxygen, sulphur, or a further nitrogen atom, R^ represents hydrogen, methyl, or ethyl, R<_ represents C-j^-C-^-alkyl, formyl, or acetyl, R^ represents hydrogen or C^C-^-alkyl, .^ represents hydrogen, halogen, C^ -C^-alkoxy hydrogen,, - - bamoyl, monoisopropylcarbamoyl,- mono-sec. butylcarbamoyl, monoallylcarbamoylj diethylcarbamoyl, diallylcarbamoyl, 2-but-3-inyl carbamoyl, n-piperidinocarbonyl , n-morpholino-carbonyl, or cyano, R^ represents hydrogen or methyl, represents formyl or acetyl, Rg represents hydrogen or methyl,' R represents hydrogen, C^-C^-alkyl, chlorine, methoxy or ethoxy,- and Rg represents chlorine or methyl, 3· Compounds according to claim 2,wherein R^represents the group -C- or -CH0-, Z represents -0-,.' -CHgO-, NH-, -CH0- or -N-, R≥' represents methyl or ethyl, R^ represents methoxycarbonyl, ethoxycarbonyl, isopropoxycarbonyl, sec. butoxycarbonyl, cyclohexyloxycarbonyl, monoethylcarba'moyl, diethylcar-bamoyl, monoisopropylcarbamoyl, · monoallylcarbamoyl, N-piperidinocarbonyl or cyano, R^. represents hydrogen or methyl, and R^, represents hydrogen,, methyl, ethyl, chlorine, methoxy or ethoxy. :· ' 4. Compounds according to. claim 3* wherein R^ represents the group R^-^ * Z represents -0-, R≥ represents methyl or ethyl, ^ represents methoxycarbonyl, ethoxy carbonyl, isopropoxycarbonyl, sec. butoxycarbonyl, diethyl-carbamoyl, monoethylcarbamoyl, or cyano, R^ represents hydrogen, and B.^ represents hydrogen, chlorine or ethyl. 5. Compounds according to claim 3> wherein R^ represents unsubstituted benzyl, Z represents -0-, R^ represents methyl, R^ represents methoxycarbonyl, ethoxycarbonyl, isopropoxycarbonyl, diethylcarbamoyl, or cyano. 6. 4-[4-(phenoxy)-phenoxy]-3-methyl-2-butenoic acid 42.156-3 7„ 4-[4-(phenoxy)-phenoxy]-3-methyl-2-l3utenoic acid ethylester according to claim 4. 8. 4-|4-[4-(chloro)-phenoxy]-phenoxyj-3-raethyl-2½ butenoic acid ethyl ester according to claim 4. gf 4-[4-(phenoxy)-phenoxy]-3-methy-t-2-b tenoic acid isopropyl ester according to claim 4. ^ 10. 4- f4- [4-( chloro ) -phenoxy ] -phenoxy^-3-me hyl-2-butenoic acid isopropyl ester according to claim 4. 11. 4- [4-(benzyl) -phenoxy] -3-methyl-2-butenoic acid ,· isopropyl ester according to claim 5. ^ 12. 4-{4-[4-(ethyl)-phenoxy]]-3-methyl-2-butenoic acid . isopropyl ester according to claim 4. 13· 4-[4-(benzyl)-phenoxy]-3-methyl-2-butenoic acid ethyl ester according to claim 5. 14. 4- [4- (benzyl) -phenoxy] -3-methyl-2-butenoic acid methyl ester according to claim 5· 15. 4-[4-(benzyl)-phenoxy]-3-methyl-2-butenoic acid diethylamide according to claim 5. . '■ 16. 4-[4-(benzyl)-phenoxy ]-3-methyl-2-butenoic acid' nitrile according to oiaim 5. 1/ IT. 4-[4-(benzoyl) -phenoxy ]-3-methylr2-butenoic acid ' ^ methyl ester according to claim 3. 18.. 4-[4-(phenoxy)-phenoxy]-3-methyl-2-butenoic acid nitrile according to claim 4., . 19. 4- [4-(phenoxy)-^phenoxy] -3-me thyl-2-butenoic- . . . ■ · ', · . ■ 1/ acid diethylamide according to claim 4. 20. 4-[4 (cyclohexyl) -phenoxy] -3-methyl-2-butenoio acid ^ ethyl ester according to claim 2. ' 21. 4-[4-(phenoxy)-anilino]-3-methyl-2-butenoic acid methyl ester according to claim 2. sec. butyl ester according to claim 4. 23. 4-[4-(phenoxy)-phenoxy]-3-methyl-2-butenoic acid monoe h l amide according to claim 4. 24. A process for the manufacture of compounds of the general formula (C^-C^-alkinyloxy)carbonyl, cyclohexyloxycarbonyl, · phenoxycar onyl, (C^-C^ haloalkenyloxy)carbonyl, the cyano group, a carbamoyl group which is mono- or disubstituted - y C1-C^-alkyl, C^-C^-alkenyl or C^-C^-alkinyl, it being possible for the substituents of the carbamoyl group together with the nitrogen atom to which they are bonded to form a saturated 5- or 6-membered heterocyclic ring which can contain in addition an oxygen, sulphur, or a further nitrogen atom, Rj^ represents hydrogen, methyl, or ethyl, R^ represents C^-C^-alkyl, formyl, or acetyl, R^ represents hydrogen or C, -C-,-alkyl, R„ represents hydrogen, halogen, C -C,_-alkoxy wherein a compound of the formula is reacted in the presence of a base with a compound of the formula R. R |4 |2 X-CH-C=CH-R in which Z and R-j^ to Rg have the meanings given hereinbefore and X represents halogen, in particular chlorine or bromine. 25. A process for the manufacture of compounds of the general formula (C.-,-C,--alkinyloxy)carbonyl, cyclohexyloxycarbonyl, . ":"' phenoxycarbonyl, (C^-C^ haloalkenyloxy)carbonyl, the cyano group, a carbamoyl group which is mono- or disubstituted -by C.^-C-.-alkyl, C^-C^-a-lJkenyl or C^-C^-alkinyl, it being possible for the substituents of the carbamoyl group together with the nitrogen atom to which they are bonded to form a saturated 5- or 6-membered heterocyclic ring which can contain in addition an oxygen, sulphur, or a further nitrogen 'atom, ^ represents hydrogen, methyl, or ethyl, represents C^-C^-alkyl, formyl, or acetyl* g represents hydrogen or C^-C^-alkyl, R^ represents hydrogen, halogen, C -C^-alkoxy hydrogen or and' Rg represents/nalogen, . methyl, or ethyl, wherein a compound of the formula reacted with a compound of. the formula in which Z and -|^ to Rg have the meanings given hereinbefore, R^ represents C-^-C^-alkyl, phenyl or p-chlorophenyl, and Me represents alkali or alkaline erath metal. 26. A process—for the manufacture of compounds of the general formula wherein represents cyclohexyl, cyclohexyloxy or the0group .·-<¾ or t the 2 represents hydrogen, methyl or ethyl, R^ represents (C1-Cj--alkoxy)carbonyl, (C^-C^-alkenyloxy)carbonyl, (C-^-C---alkinyloxy)carbonyl, or cyclohexyloxycarbonyl, wherein the compound of the formula is reacted with a compound of the formula R100H in the presence of an acid catalyst, or with a compound of the formula R10X in the presence of a base, in which R^^ represents Cl~C "alkyli or cyclohexyl, 27· A process for the manufacture of compounds of the general formula where Z' re group is bonded to the phenyl nucleus, R≥ represents hydrogen, methyl or ethyl, represents -C00H, (C^-Cj.-alkoxyjcarbonyl, (C^-C^-alkenyloxy)carbonyl, (C^-C^-alkinyloxy) carbonyl, cyclohexyloxycarbonyl, phenoxycarbonyl, (C^-C^ haloalkenyloxy)carbonyl, the cyano group, a carbamoyl group which is mono- or disubstituted -¾y C-L-C^-alkyl, C^-C^-alkenyl or C^-C^-alkinyl, it being possible for the substituents of the carbamoyl group together with the nitrogen atom to which they are bonded to form a saturated 5- or 6-membered heterocyclic ring which can wherein a compound of the formula in which R'-^ R2 ¾ anc ^a e thenBanings given hereinbefore, is reacted with an acylating reagent or with an alkylating agent. 28. A process for the manufacture of compounds of the general formula R wherein Υ' repr -0CH2~ or the direct bond, R≥ represents hydrogen, methyl, or ethyl, R^ represents -C00H, (C1-Cj--alkoxy)carbonyl, (C^-C^-alkenyloxy)carbonyl, ' . (C^-C^-alkinyloxy)carbonyl, cyclohexyloxycarbonyl, " ■""·" phenoxycar onyl, (C-^-C^ haloalkenyloxy)carbonyl, the cyano group, a carbamoyl group which is mono- or disubstituted -by C^-C^-alkyl, C^-C^-alkenyl or C^-C^-alkrnyl, it being possible for the substituents of the carbamoyl group together with the nitrogen atom to which they are bonded to form a saturated 5- or 6-membere'd heterocyclic ring which can contain in addition an oxygen, sulphur, or' a further nitrogen atom, ^ represents hydrogen, methyl, or ethyl, represents wherein a compound of. the formula in which R≥ to Rg, Y* and R^ have the meanings given hereinbefore, is reacted with an acylating agent or with an alkylating agent. · 29. Pesticidal agents which contain as active substance at least one compound of the general formula represents hydrogen, C-^-C^-alkyl, R^ represents -C00H, (C1-C^-alkoxy)carbonyl, (C^-C^-alkenyloxy)carbonyl, (C^-C^-alkinyloxy)carbonyl, cyclohexyloxycarbonyl, phenoxycar onyl, (C^-C^ haloalkenyloxy)carbonyl, the cyano group, a carbamoyl group which is mono- or disubstituted •by C1-C^-allyl, C-^-C^-alkenyl or C^-C^-alldnyl, it being possible for the substituents of the carbamoyl group together a saturated 5~ or. β-membered heterocyclic ring which can contain in addition an oxygen, sulphur, or a further nitrogen atom, R). represents hydrogen, methyl, or ethyl,- Rc represents '+ ... · · . ■ · . C-^-C^-alkyl, formyl, or acetyl, Rg represents hydrogen or C-^-C^-alkyl, ^. represents hydrogen, halogen, C -C^-alkoxy or ' C-^-C^-alkyl , and Rg represents hydrogen, halogen, methyl or ethyl, together with suitable carriers and/or other additives. 30. Agents according to- claim 29, which contain as active substance at least one compound according to any one of claims 2 to 23. 31. A method of , combating pests at a locus, which method comprises applying to the. locus a compound as claimed in any one of claims 1 to 23. 32. A method according to Claim 31, wherein insects are combated.
IL42156A 1972-05-10 1973-05-01 Substituted butenoic acid derivatives their manufacture and use as pesticides IL42156A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CH701172A CH566709A5 (en) 1972-05-10 1972-05-10 Phenyl-substd butenoic acid derivs - with insectidal activity
CH1425572A CH578317A5 (en) 1972-09-29 1972-09-29 Phenyl-substd butenoic acid derivs - with insectidal activity
CH456773A CH578825A5 (en) 1973-03-29 1973-03-29 Phenyl-substd butenoic acid derivs - with insectidal activity

Publications (2)

Publication Number Publication Date
IL42156A0 IL42156A0 (en) 1973-07-30
IL42156A true IL42156A (en) 1976-11-30

Family

ID=27174895

Family Applications (1)

Application Number Title Priority Date Filing Date
IL42156A IL42156A (en) 1972-05-10 1973-05-01 Substituted butenoic acid derivatives their manufacture and use as pesticides

Country Status (18)

Country Link
JP (1) JPS6011005B2 (en)
AT (1) AT328223B (en)
CA (1) CA1055511A (en)
DD (1) DD109315A5 (en)
DE (1) DE2322853C3 (en)
DK (1) DK134463B (en)
EG (1) EG11425A (en)
ES (1) ES414565A1 (en)
FI (1) FI55986C (en)
FR (1) FR2189368B1 (en)
GB (1) GB1422181A (en)
HU (1) HU168015B (en)
IL (1) IL42156A (en)
IT (1) IT994860B (en)
NL (1) NL175813C (en)
OA (1) OA04387A (en)
PH (1) PH10001A (en)
SE (1) SE402584B (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1479297A (en) * 1974-07-04 1977-07-13 Beecham Group Ltd 4-substituted butan-2-ones but-3-en-2-ones butan-2-ols and but-3-en-2-ols and pharmaceutical compositions containing them
CH609024A5 (en) * 1974-09-30 1979-02-15 Lafon Labor Process for the preparation of new sulphur-containing diaryl and oxygen-containing diaryl compounds
DE3269621D1 (en) * 1981-08-07 1986-04-10 Ciba Geigy Ag Phenoxyphenyl-aminocarboxylic-acid derivatives, their preparation, compositions containing them and their use

Also Published As

Publication number Publication date
DK134463B (en) 1976-11-15
PH10001A (en) 1976-07-13
EG11425A (en) 1977-08-15
NL175813B (en) 1984-08-01
NL7306547A (en) 1973-11-13
FI55986C (en) 1979-11-12
DK134463C (en) 1977-05-16
IT994860B (en) 1975-10-20
DE2322853B2 (en) 1980-05-08
FR2189368B1 (en) 1978-01-06
JPS4954526A (en) 1974-05-27
HU168015B (en) 1976-02-28
SE402584B (en) 1978-07-10
CA1055511A (en) 1979-05-29
AT328223B (en) 1976-03-10
AU5527273A (en) 1974-11-07
DE2322853A1 (en) 1973-11-29
GB1422181A (en) 1976-01-21
OA04387A (en) 1980-02-15
IL42156A0 (en) 1973-07-30
ATA407773A (en) 1975-05-15
FI55986B (en) 1979-07-31
DD109315A5 (en) 1974-11-05
JPS6011005B2 (en) 1985-03-22
NL175813C (en) 1985-01-02
ES414565A1 (en) 1976-05-16
FR2189368A1 (en) 1974-01-25
DE2322853C3 (en) 1981-01-15

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