IL39092A - Pyrazole derivatives and their use as plant growth regulants - Google Patents

Abstract

1366035 Pyrazole compounds E I DU PONT DE NEMOURS & CO 24 April 1972 [22 April 1971 29 Feb 1972] 19011/72 Heading C2C Novel compounds of formulae wherein D is one of the formulae and X<SP>1</SP> is H, F, Cl or Br; n = 1-3; Y<SP>1</SP> is H, C 1-4 alkyl, C 1-4 alkoxy or CF 3 ; R is H, C 1-4 alkyl, or a group selected from -CH 2 -, -CH 2 CH 2 -, and -CH=CH-, which joins the 4 position of the pyrazole ring with the 2-position of the R 1 substituent; R 1 is C 4-12 tert-alkyl, naphthyl optionally substituted by lower alkyl, phenanthryl, wherein X is H, halogen, C 1-4 alkyl, hydroxy, C 1-4 alkoxy, C 1-4 alkylthio, NO 2 , MeSO 2 -, CF 3 , CN, carboxy, C 1-4 carboalkoxy or lower alkyl carbonyldioxy; Y is H, halogen, C 1-4 alkoxy or C 1-4 alkyl; Z is H, halogen, C 1-4 alkoxy or C 1-4 alkyl; Q is H, C 1-4 alkyl or R 4 is C 1-4 alkyl, C 1-4 alkoxy or -NMe 2 ; B is -OM, -SM or -NR 2 R 3 ; M is H, benzyl, cycloalkyl, C 1-6 alkyl optionally substituted by OH or halogen, Na, Li, K, Ca, Mg, Ba or wherein R 2 and R 3 are each H or C 1-6 alkyl, R 5 , R 6 and R, are each independently H or C 1-4 alkyl; and R 8 is H, C 1-12 alkyl or benzyl, and when M is H, benzyl or C 1-6 alkyl, R 8 is optionally substituted by OH or halogen, and salts of these novel compounds, may be prepared either by (i) a process comprising reacting a pyrazolo[5,1-a]isoindol-8-one of formula optionally saturated in the 3, 3a or 4, 5, 6, 7- positions. with a nucleophilic compound of general formula BH (e.g. MeOH, NaOH, HI, NaHS or liquid NH 3 ) or (ii) a process comprising reacting a 2-acylacetyl-benzoic acid of general formula or a 3,4,5,6-dihydro derivative thereof with a compound NH 2 NHQ or a salt or hydrate thereof. The novel compounds exhibit plant growth regulant properties. [GB1366035A]

Claims (8)

CLAIMS: .

1. A compound of the formula X' ie hydrogen, fluorine, chlorine or bromine; or Y' is hydrogen / alkyl of 1 to carbon atoms; R is hydrogen, alkyl of 1 to 4 carbon atoms, or may be a group selected from the group consisting of -CHa-, -CHaCH2-, and -CH=CH-, which joins the ^-position of the pyrazole ring with the 2-position of the R^ substituent is tert-alkyl of through 8 carbon atoms, naphthyl, phenanthryl, X is hydrogen, halogen, alkyl of 1 to carbon atoms, hydroxy, alkoxy of 1 to carbon atoms, nitro, trifluoromethyl, carboxy, or carboalkoxy of 1 to h carbon atoms; Y is hydrogen, halogen, alkoxy of 1 to h carbon atoms, or alkyl of 1 to carbon atoms; Z is hydrogen, halogen, alkoxy of 1 to carbon atoms or alkyl of 1 to carbon atoms; Q is hydrogen, alkyl of 1 to h carbon atoms or 0 II R* is alkyl of 1 to 4 carbon atoms or t ■ · - · (CH5)2N-; B is -0M, -SM, or - \ M is hydrogen, benz l^"alkyl of 1 to 6 carbon atoms optionally substituted with_hydroxy i . j^* R and R, are each hydrogen or alkyl of 1 to 6 { carbon atoms; and is hydrogen or alkyl of 1 to 6 carbon atoms; as well as the alkali metal, alkaline earth and ammonium salts of these compounds and their addition salts with strong inorganic acids; provided that in the compounds of formula II, R is hydrogen, is phenyl or lower alkoxyphenyl and Q is hydrogen or alkyl of 1 to 6 carbon atoms 0

2. The compound of Claim 1 wherein is -methoxyphenyl, p-methylphenyl, jo-chlorophenyl or phenyl.

3. The compound of Claim 2 wherein R is hydrogen. k.

4. The compound of Claim 1 wherein R is hydrogen and B is hydroxy.

5. A plant growth regulating composition comprising an inert diluent and a plant growth regulating amount of a compound of Claim 1.

6. A plant growth regulating composition comprising an inert diluent and a plant growth regulating amount of a compound of Claim j5.

7. The method of regulating the growth of plants comprising applying to the locus of growth of a plant a growth regulating amount of a compound of Claim 1.

8. The method of regulating the growth of plants comprising Applying to the locus of growth of a plant a . growth regulating amount of a compound of Claim 3.