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GB957831A - Amino-trichloropicolinic acid compounds - Google Patents

Amino-trichloropicolinic acid compounds

Info

Publication number
GB957831A
GB957831A GB627363A GB627363A GB957831A GB 957831 A GB957831 A GB 957831A GB 627363 A GB627363 A GB 627363A GB 627363 A GB627363 A GB 627363A GB 957831 A GB957831 A GB 957831A
Authority
GB
United Kingdom
Prior art keywords
acid
group
compounds
esters
prepared
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
Application number
GB627363A
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.)
Dow Chemical Co
Original Assignee
Dow Chemical 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 Dow Chemical Co filed Critical Dow Chemical Co
Publication of GB957831A publication Critical patent/GB957831A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/84—Nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/86—Hydrazides; Thio or imino analogues thereof

Landscapes

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

Abstract

Compounds of the formula <FORM:0957831/C1/1> where Y is a carboxylic acid group or a functional derivative thereof, L is an integer, and Z is the residue of a nitrogen base (see Division C2) are plant growth regulants. They are said to speed up the germination of seeds, and to stimulate the formation of roots, buds and flowers; they may be used to produce seedless fruits without the use of pollen and to prevent or retard the formation of the abscission layer on fruit trees to prevent premature fruit drop. In other applications the compounds may be used to cause fruit drop, set flowers or defoliate plants. The compounds of the above formula may be used as compositions (see Division A5). Specification 957,277 is referred to.ALSO:The invention comprises compounds of the formula: <FORM:0957831/C2/1> where Y is a carboxylic acid group or a functional derivative thereof (e.g. a cyano, carboxylic acid salt, carboxylic acid ester, carboxylic acid hydrazide or carboxylic acid amide group), L is an integer, and Z is the residue of a nitrogen base having at least one >NH group (the other valencies being attached to C, H or N) which has a basic dissociation constant of 10-7 or greater, Z being attached to the pyridine ring by way of the nitrogen of the above group. The free valencies of the >NH group can be satisfied by hydrogen, alkyl, alkenyl, alkynyl, hydroxyalkyl, aralkyl, cycloalkyl, amino, dialkylamino, guanyl, aminoalkyl, poly(aminoalkylene)-aminoalkyl, pyridyl, pyrimidinyl or triazyl, or they may make up a ring, such as ethyleneimine, trimethyleneimine, pyrrolidine, alkylpyrrolidine, piperidine, alkylpiperidine, piperazine, alkylpiperazine or morpholine. When L is 2 Z may be -NHNH-, -(NHCmH2m)xNH-, -NHCnH2nNH-, <FORM:0957831/C2/2> and <FORM:0957831/C2/3> where m, n and x are integers. Many nitrogen bases ZHL are specified. The group Y is e.g. COOH, COOM, CN CONH2, CONHR1, CONR1R2, CONHNH2, CONHNHR3 or COOR4. M is a salt group, e.g. NH4, Na, K, Li, Mg, Ca, Cu, Fe, Zn, Co, and Ni, or a substituted or quaternary ammonium group, several of which are specified; R1 and R2 are lower aliphatic radicals (including hydroxyalkyl); R3 is aliphatic or aromatic; and R4 is the residue of a compound R4OH, many of which are specified. Compounds in which Y is COOH may be prepared by heating the corresponding compound having Y=CCl3 with aqueous acid, or by hydrolysis of a corresponding lower alkyl ester. Esters are prepared by esterifying the acid or a derivative thereof; or lower alkyl esters may be prepared by reacting the compound with Y=CCl3 with the alkanol and water in the presence of AgNO3. Some esters may be prepared by reacting a salt of the acid with a halide corresponding to the alcohol, or the acid chloride (from the acid and SOCl2) with the hydroxy compound in the presence of a tertiary amine. Salts are prepared by reacting the acid with a suitable base, or, for metals which form difficulty soluble hydroxides, by reacting an alkali metal salt of the acid with a soluble mineral acid salt of the metal. Amides and hydrazides are prepared from a suitable ester and the appropriate base. Nitriles are prepared from P2O5 and the corresponding -CONH2 compound. Many examples are given. The compounds of the invention are pesticides and plant growth regulants (see Division A5). Specification 957,277 is referred to.ALSO:Compounds of the formula <FORM:0957831/A5-A6/1> where Y is a carboxylic acid group or a functional derivative thereof, L is an integer, and Z is the residue of a nitrogen base (see Division C2) are plant-growth regulants and pesticides. The growth of plants or plant parts may be modified by applying to them a compound of the above formula or a composition containing it in admixture with a plant growth control or herbicide additive and/or an inert carrier. Specified carriers are water, organic solvents, petroleum distillates, surface-active dispersing agents, aqueous oil emulsions, chalk, talc, bentonite and other clays. The Compositions may also contain other plant growth control agents (many of which are specified), hormones, contact herbicides, pesticides and/or modifying agents. Specified additional plant growth regulants are aminotriazines; phenylureas; 3 - phenyl - 1,1 - dimethylurea trichloracetate; chlorinated phenoxy aliphatic acids and their salts and esters; carbamates; chlorinated benzoic acids and their salts and esters; chlorinated lower aliphatic acids and their salts and esters; nitrophenols; pentachlorophenol; 5-bromo - 3 - isopropyl - 6 - methyluracil; arsenic compounds; sodium chlorate; sodium borates; 3,6 - endox - o - hexahydrophthalic acid; o-(2,4 - dichlorophenyl) - o - methyl isopropyl phosphoramidothioate; 3,4 - dichloropropionahilide; 1,2 - dihydroxypyridazine - 3,6 - dione; 3 - amino - 1,2,4 - triazole; 2,3,6 - trichlorophenylacetic acid and its salts and esters; 1,11-ethylene - 2,21 - dipyridylium dibromide; 2,6 dinitro - N,N - di - n - propyl - 2,2,2 - trifluoro - p - toluidine; a - chloro - N - diallyl acetamide and herbicidal oils. Specification 957,277 is referred to.
GB627363A 1962-03-06 1963-02-15 Amino-trichloropicolinic acid compounds Expired GB957831A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US17775462A 1962-03-06 1962-03-06
US23344262A 1962-10-26 1962-10-26

Publications (1)

Publication Number Publication Date
GB957831A true GB957831A (en) 1964-05-13

Family

ID=26873613

Family Applications (1)

Application Number Title Priority Date Filing Date
GB627363A Expired GB957831A (en) 1962-03-06 1963-02-15 Amino-trichloropicolinic acid compounds

Country Status (11)

Country Link
BE (1) BE628487A (en)
BR (1) BR6347073D0 (en)
CH (1) CH449323A (en)
DE (1) DE1445657A1 (en)
DK (1) DK106651C (en)
ES (3) ES285179A1 (en)
FI (1) FI40339B (en)
GB (1) GB957831A (en)
MY (1) MY6500036A (en)
NL (2) NL123448C (en)
SE (1) SE313458B (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BR6575384D0 (en) * 1965-03-22 1973-09-20 Amchem Prod PERFECTED HERBICIDIC COMPOSITES AND PROCESS TO PREPARE USIBLE AMINE SALT COMPOUNDS AS AN ACTIVE COMPONENT IN THAT COMPOSITION

Also Published As

Publication number Publication date
ES285179A1 (en) 1963-10-16
CH449323A (en) 1967-12-31
SE313458B (en) 1969-08-11
BE628487A (en)
BR6347073D0 (en) 1973-05-24
DK106651C (en) 1967-02-27
MY6500036A (en) 1965-12-31
NL288968A (en)
ES290054A1 (en) 1963-12-01
DE1445657A1 (en) 1969-03-27
NL123448C (en)
ES290053A1 (en) 1963-12-01
FI40339B (en) 1968-09-02

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