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IL42877A - Phthalimide derivatives and plant growth regulants containing them - Google Patents

Phthalimide derivatives and plant growth regulants containing them

Info

Publication number
IL42877A
IL42877A IL42877A IL4287773A IL42877A IL 42877 A IL42877 A IL 42877A IL 42877 A IL42877 A IL 42877A IL 4287773 A IL4287773 A IL 4287773A IL 42877 A IL42877 A IL 42877A
Authority
IL
Israel
Prior art keywords
alkyl
compound
hydrogen
formula
cor
Prior art date
Application number
IL42877A
Other versions
IL42877A0 (en
Original Assignee
American Cyanamid Co
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
Application filed by American Cyanamid Co filed Critical American Cyanamid Co
Publication of IL42877A0 publication Critical patent/IL42877A0/en
Publication of IL42877A publication Critical patent/IL42877A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
    • C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A01N37/32—Cyclic imides of polybasic carboxylic acids or thio analogues thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
    • C07C65/24—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups polycyclic

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Indole Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

1395104 Substituted phthalimides AMERICAN CYANAMID CO 2 Aug 1973 [21 Aug 1972 5 April 1973] 36836/73 Heading C2C The invention comprises compounds of Formulae I and II wherein W is hydrogen or C 1 to C 4 alkyl; X and X<SP>1</SP> each represents hydrogen, halogen, C 1 to C 4 alkyl, CF 3 , C 1 to C 4 alkoxy, benzyloxy, di- (C 1 to C 4 )alkylamino, C 1 to C 4 alkylthio, hydroxy, C 1 to C 4 alkylsulphonyl, C 1 to C 4 alkanoylamino or nitro, with the proviso that at least one of X and X<SP>1</SP> is a substituent other than hydrogen; Y is -COOR 3 , -CONHR 3 , -CONR 3 R 4 , -CONHN(R 5 ) 2 , -CN or -COR 7 , R 1 and R 2 each represent C 1 to C 4 alkyl or when taken together with the carbon to which they are attached form C 4 to C 11 cycloalkyl optionally substituted with methyl; R 3 and R 4 each represent hydrogen or C 1 to C 4 alkyl; R 5 and R 6 each represent C 1 or C 2 alkyl; R 7 is halogen, R 8 is -CH 3 or where Z and Z<SP>1</SP> are hydrogen, C 1 or C 2 alkyl, halogen, -CF 3 or -OCH 3 and # is a single or double bond with the proviso that there be only 0 or 1 double bond in the ring. They may be prepared by nucleophilic substitution reactions between the appropriate amino compound of formula NH 2 CR 1 R 2 Y with an o-phthalic acid derivative of the Formulae III or V where X, X<SP>1</SP>, W, R 1 , R 2 and Y are as defined above except that Y is not -COR 7 and T 1 and T 2 are the nueleophilic substituents to be displaced, e.g. Cl or C 1 to C 4 alkoxy. When Y is -COR 7 , the desired acid halide is produced through the additional step of halogenating the appropriate carboxylic acid (Y being -COOH) with a conventional halogenating agent. Alternatively, the amino compound of formula NH 2 CR 1 R 2 Y may be reacted with the appropriate phthalic anhydride of Formulae VI or VIII where X, X<SP>1</SP>, Y, W, R 1 and R 2 are as defined above except that Y is not -COR 7 , the latter compounds being formed from the carboxylic analogues as described above. The phthalic anhydride derivatives of Formulae VI and VII may be prepared by dehydration of the corresponding acid. The acid halides prepared as above may be converted to the corresponding amide by reaction with ammonia, dialkyamine or dialkyl hydrazine. Phthalimido acetamides in which R 4 is hydrogen may be prepared by reacting the appropriate phthalic, tetrahydro- or hexahydrophthalic anhydride with the appropriate α,α - disubstituted - α - amino nitrile to give the corresponding phthalamic acid, which is then cyclized to give the phthalimido, tetra- or hexahydrophalimido nitrile, followed by hydration. To form the hydrozinium halide, an amide of formulae is reacted with an alkyl halide. The tetra- and hexahydrophthalimido hydrazinium salts may also be prepared in like manner. Phthalimido esters of formulae may be prepared by reacting a C 1 -C 4 diazoalkane with the corresponding acid, i.e. where R 3 is hydrogen. Alternatively, the phthalic, tetra- or hexahydrophthalic anhydride may be reacted with the appropriate α-amino ester, or the acid halide may be reacted with a C 1 -C 4 alkanol in the presence of an acid acceptor. The phthalimido nitrile may be obtained by dehydration of the corresponding amide. The compounds of Formulµ I and II may also be prepared by reacting a compound of formula where R 1 , R 2 and Y are as above, except that Y cannot be -COR 7 or with a substituted phthaloyl chloride of formula They may also be prepared by reacting the compound where W, X and X<SP>1</SP> are as above and R 9 is C 1 -C 4 alkyl, with a compound of formula where R 1 , R 2 and Y are as above, except that Y cannot be -COR 7 or to give a product which can then be cyclized. The compounds of Formulae I and II above except those in which Y is -COR 7 together with those in which both X and X<SP>1</SP> are hydrogen may be used as plant growth regulating agents. [GB1395104A]

Claims (9)

1. compound characterized as having the formula: wherein W is hydrogen or alkyl C^-C^; X and X' each represents hydrogen, halogen, alkyl C-^-C^, CF^, alkoxy C^-C^, benzyloxy, di (C^-C^alkylamino, C-^-C^ alkylthio, hydroxy, C^-C^ alkylsulfonyl , alkanoylamino C-^-C^ or nitro; Y is -C OOR 3 , -CONHR Q , -CONR ^ , -CONHN C R ^ , - CONHN®(R6 ) ^ "hal-ide®, -CN or - COR ., with the proviso that at least one of X and X· is a substituent other than hydrogen; R^ and R2 each represent alkyl C^-C^ or when taken together with the carbon to which they are attached form cyclo-alkyl C^-C^^ optionally substituted with methyl; R^ and R^ each represent hydrogen or alkyl C-^-C^; R^ and Rg each represent alkyl cy^2' R7 s al°gE N J Rg s -CH^ or where Z and Z' are hydrogen, alkyl C1-C2' halogen, -CP^ or -OCH^ and - : is a single or double bond with the proviso that there be only 0 or 1 double bond in the ring.
2. A compound according to Claim 1 wherein Y is -CONR^.
3. A compound according to Claim 1 wherein Y is -COOR compound according to Claim 1 wherein Y is -CONHN(R5)2. 5. A compound according to Claim 1 wherein Y -CONH^(R6 ) -halide®. 6. A compound according to Claim 1 wherein Y A compound according to Claim 1 wherein Y is -COR compound according to Claim 1 wherein Y is -CONHRg . 9. A compound according to Claim 2, l-(3--chlorophthalimido)cyclohexanecarboxamlde . 10. A compound according to Claim 2, l-(3--chlorophthallmido )cyclopentanecarboxamide . 11. A compound according to Claim 2, l-(4--chlorophthalimido)cyclohexanecarboxamide . 12. A compound according to Claim 2, 1-(M--methylphthalimido )-l-cyclohexanecarboxamide . 13. A compound according to Claim 2, l-(3,- , 5 , 6-tetrahydrophthalimido )-1-cyclohexanecarboxamlde . 1
4. A compound according to Claim 2, a-iso-butyl-a-methyl-a- ( 3-chlorophthalamido )acetamide . 1
5. A compound according to Claim 2, l-(3--trifluoromethylphthalimido)cyclohexanecarboxamide . 1
6. A compound according to Claim 2, l-(3,5--dichlorophthalamido)-l-cyclohexanecarboxamide . 17· A method for regulating the growth of plants characterized by applying to the foliage, roots, stems, seeds, seed pieces or to soil in which the plants are grown, an effective plant growth regulating amount of a compound having the formula: wherein W is hydrogen or lower alkyl C^-C^; X and X' each represent hydrogen, alkyl C^-C^, -CF^, alkoxy C^-C^, benzyloxy, di(C1-Cli)alkylamino, C^-C^ alkylthio, hydroxy, C-j^-C^ alkylsulfonyl, halogen, alkanoylamino C^-C^ or nitro; Y is -CONHRg, -COOR^ -CO R^, -CONHN(R5)2, -CONHN®(R6)3'halide®, or -CN; Rx and R2 each represent alkyl C^-C^ or when taken together with the carbon to which they are attached form cycloalkyl cij-cn optionally substituted with methyl; R^ and R^ each represent hydrogen or alkyl C-^-C^ R,- and Rg each represent alkyl C^- alkyl C1~C2, halogen, -CF^ °r -OCH^ and —-— is a single or double bond with the proviso that there be only 0 or 1 double bond in the ring; or mixtures thereof. 18. A method according to Claim 17, wherein the active compound is applied to the seeds, seed pieces or soil containing seeds or seed pieces of the plants for which plant growth regulation is desired. 19. A method according to Claim 17, wherein the compound is applied to the foliage and stems of the plants for which plant growth regulation is desired. 20. A method according to Claim 17, wherein the compound is applied to the roots of the plants for which plant growth regulation is desired. 21. A method according to Claim 19, wherein the active compound is applied at the rate of from 0.06 pound to 32 pounds per acre. 22. A method according to Claim 18, wherein the active compound is applied at the rate of from 0.06 pound to 32 pounds per acre in the area of application. 23. A method according to Claim 17, wherein Y of the formula is -CONR^R^. 24. A method according to Claim 17, wherein Y of the formula is -C0NHN(Rc) .. 25· A method according to Claim 17, wherein Y of the formula is -COOR^. 26. A method according to Claim 17, wherein the compound applied is 1- ( 3-chlorophthalimido )cyclohex-anecarboxamide ; 1-phthalimidocyclohexanecarboxamide ; 1- ( 3-chlorophthalimido )cyclopentanecarboxamide; 1-phthalimidocyclopentanecarboxamide ; l-(4-chlorophthalimido)--c clohexanecarboxamide ; 1- ( -methylphthalimido )-l-cyclohexanecarboxamide ; 1- ( 3 , 4 , 5 , 6-tetrahydrophthaalimido )-1--cyclohexanecarboxamide ; a-isobutyl-a-methyl-a- ( 3--chlorophthalimido)-acetamide or 1- ( 3-trifluoromethylphthalimido )cyclohexanecarboxamide . 2
7. A process for the preparation of the compounds of formulas I and II characterized by the reaction of an amino compound of the formula NI^CR-jF^Y with an o-phthalic acid derivative of the formula: wherein X, X', , R≥ and Y are as defined in Claim 1, with the proviso that Y is not -COR,-,; and T2 are the nucleophllic substltuents to be displaced which may * be taken together to form a ring as in the case of an acid anhydride. 2
8. A process according to Claim 27 wherein T1 and 2 are selected from the group of -CI, -OR (C^-C^) 2
9. A process according to Claim 27, wherein Y is -COOH further characterized by the additional step of a halogenation to form the corresponding compound wherein Y is -COR^. 30. A process according to Claim 27 characterized by the reaction of a phthalic anhydride of the formula : wherein X, X' and W are as defined for the compounds of formulas I and II; with an a-amino compound of the formula: NHgCRjRgY wherein R^, R2 and Y are as defined for the compounds of formula I and II provided that Y is not -COR.-,. 31. A process according to Claim 30 further characterized by the fact that Y is -COOH in the a-amino compound and by the additional step of halogenatlng the phthalimide derivative produced to form the corresponding compound wherein Y is -COR,-,. 32. A process according to Claim 30, further characterized in that Y is -CN and the reaction is conducted in the presence of an inert solvent at a temperature between 20°C. and 60°C; treating the thus-formed reaction mixture with a dehydrating agent at a temperature of from 0°C. to 100°C. and then treating the resulting reaction mixture with a strong acid at a temperature between about -10°C. and 30°C. 33· A compound according to Claim 1, characterized as having the formula: wherein X is halogen, alkyl C-^-C^ or nitro; Y is -COOR^, -CON(R4)2, -CONHN(R5)2, -CONHN+ (Rg ) 3 · halide", -CN or -COR^; R1 and R2 each represent alkyl C^-C^ or when taken together with the carbon to which they are attached form cycloalkyl Cjj-C^ ^3 and Rn each represent hydrogen or alkyl C^-C^; R^ and Rg each represent alkyl C1-C2 and R^ is halogen. 34. A compound according to Claim 1 characterized as having the formula: wherein W is hydrogen or alkyl C^-C^ X is halogen, alkyl C1-C14, alkanoylamino C^-C^ or nitro; Y is -COOR^, -CONHRg-, -CON(R1+)2, -CONHN(R5)2, -CONHN+(R6)3 -halide", -CN or -COR.-,; 1 and R2 each represent alkyl C^-C^ or When taken together with the carbon to which they are attached form cycloalkyl C^-C^ R^ and R^ each represent hydrogen or alkyl C^-C^; R^ and Rg each represent alkyl C1-c2' R7 is nal°Sen» R8 is -CH3 or where Z and Z* are hydrogen, alkyl C^-Cg* halogen, -CP^ or -OCH^ and — - is a single or double bond with the proviso that there be only 0 or 1 double bond in the ring. 35. A method according to Claim 17 further characterized in that the compound applied is that of Claim 33. 36. A method according to Claim 17 further characterized in that the compound applied is that of Claim 31». 37. An industrial method for the manufacture of a plant growth regulating composition characterized by the admixing of an effective amount of a compound of Claim 17 with a solid or liquid diluent. S. HOROWITZ & CO. AGENTS FOR APPLICANTS
IL42877A 1972-08-21 1973-08-01 Phthalimide derivatives and plant growth regulants containing them IL42877A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US28253772A 1972-08-21 1972-08-21
US34835573A 1973-04-05 1973-04-05

Publications (2)

Publication Number Publication Date
IL42877A0 IL42877A0 (en) 1973-11-28
IL42877A true IL42877A (en) 1976-04-30

Family

ID=26961500

Family Applications (1)

Application Number Title Priority Date Filing Date
IL42877A IL42877A (en) 1972-08-21 1973-08-01 Phthalimide derivatives and plant growth regulants containing them

Country Status (21)

Country Link
JP (1) JPS5924962B2 (en)
AR (2) AR198862A1 (en)
CA (1) CA1011746A (en)
CH (1) CH595345A5 (en)
CS (1) CS187383B2 (en)
DD (1) DD109313A5 (en)
DE (1) DE2342229A1 (en)
DK (1) DK139028B (en)
EG (1) EG11017A (en)
ES (2) ES418051A1 (en)
FR (1) FR2197000B1 (en)
GB (1) GB1395104A (en)
HU (1) HU170761B (en)
IE (1) IE38049B1 (en)
IL (1) IL42877A (en)
IT (1) IT990371B (en)
NL (1) NL180103C (en)
OA (1) OA04463A (en)
PH (1) PH10480A (en)
RO (3) RO69382A (en)
SE (1) SE402457B (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ZA743426B (en) * 1973-06-25 1976-01-28 American Cyanamid Co Plant growth regulants
US5019154A (en) * 1989-12-11 1991-05-28 American Cyanamid Company Substituted phthalimido cyclohexanecarboxamides and the use thereof for enhancing growth of hybrid tea rose plants
CN113461674B (en) * 2021-08-09 2022-05-13 山东农业大学 Amide compound for promoting plant root growth and preparation method and application thereof

Also Published As

Publication number Publication date
DK139028C (en) 1979-05-14
JPS49132236A (en) 1974-12-18
IE38049B1 (en) 1977-12-07
CS187383B2 (en) 1979-01-31
OA04463A (en) 1980-03-15
PH10480A (en) 1977-05-11
DD109313A5 (en) 1974-11-05
IT990371B (en) 1975-06-20
RO69383A (en) 1981-01-30
AU5892873A (en) 1975-02-06
JPS5924962B2 (en) 1984-06-13
AR198862A1 (en) 1974-07-24
HU170761B (en) 1977-09-28
CH595345A5 (en) 1978-02-15
GB1395104A (en) 1975-05-21
NL7311503A (en) 1974-02-25
IE38049L (en) 1974-02-21
AR199834A1 (en) 1974-09-30
RO69382A (en) 1980-07-15
IL42877A0 (en) 1973-11-28
CA1011746A (en) 1977-06-07
DE2342229C2 (en) 1988-03-10
RO69337A (en) 1980-08-15
EG11017A (en) 1976-10-31
ES442695A1 (en) 1977-04-16
DE2342229A1 (en) 1974-03-07
SE402457B (en) 1978-07-03
ES418051A1 (en) 1976-05-01
NL180103C (en) 1987-01-02
NL180103B (en) 1986-08-01
DK139028B (en) 1978-12-04
FR2197000A1 (en) 1974-03-22
FR2197000B1 (en) 1978-04-21

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