Method of producing hybrid cereal grain seeds by application of 1-aryl-1,4-dihydro-4-oxo(thio)-pyridazines
AssigneeRohm and Haas Company
InventorTed T. Fujimoto
Life of this patent
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Abstract
Compounds of the formula ##STR1## wherein R.sup.1 is aryl or substituted aryl, R.sup.2 is alkyl, or aryl, R.sup.3 is hydrogen, alkyl, aralkyl, or halogen, or R.sup.2 and R.sup.3 taken together are --(CH.sub.2).sub.n -- where n is 3 to 8 Z is oxygen or sulfur, and Y is the group Z'R.sup.4 or NR.sup.5 R.sup.6 wherein Z' is oxygen or sulfur, R.sup.4 is hydrogen, alkoxyalkyl, alkyl, cycloalkyl, cycloalkylalkyl, haloalkyl, phenyl or benzyl or a cation R.sup.5 and R.sup.6 are independently hydrogen or alkyl or when R.sup.5 is hydrogen, R.sup.6 is hydroxy or an alkyl metal salt thereof. These compounds are active as plant growth regulators, and particularly as chemical hybridization agents.
Claims23
A method of inducing male sterility in a cereal grain or forage plant which comprises treating the plant prior to meiosis with an amount effective to produce male sterility in the plant of a compound of the formula ##STR10## wherein R.sup.1 is an unsubstituted phenyl group or a phenyl group substituted with up to three substituents selected from the group consisting of halogen atoms, (C.sub.1 -C.sub.4) alkyl, (C.sub.1 -C.sub.4) alkoxy, (C.sub.1 -C.sub.4) alkylthio, (C.sub.1 -C.sub.4) alkylsulfinyl, (C.sub.1 -C.sub.4) alkylsulfonyl or trifluoromethyl,
- R.sup.2 is a (C.sub.1 -C.sub.4) alkyl group, or phenyl,
- R.sup.3 is a hydrogen atom, a (C.sub.1 -C.sub.4) alkyl group, or a halogen atom, a benzyl group or a phenethyl group,
- Z is oxygen or sulfur, and
- Y is the group Z'R.sup.4 or NR.sup.5 R.sup.6
- wherein Z' is oxygen or sulfur,
- R.sup.4 is hydrogen, (C.sub.1 -C.sub.4) alkyl, (C.sub.1 -C.sub.4) alkoxyalkyl, cyclohexylmethyl, bromopropyl, phenyl or benzyl,
- R.sup.5 and R.sup.6 are independently selected from the group consisting of hydrogen or (C.sub.1 -C.sub.4) alkyl or (C.sub.1 -C.sub.4) alkyl substituted with carboxyl or (C.sub.1 -C.sub.4) alkoxycarbonyl, or when
- R.sup.5 is hydrogen, R.sup.6 is hydroxyl,
- or an agronomically acceptable salt, (C.sub.1 -C.sub.12) alkyl ester or mono or di(C.sub.1 -C.sub.4) alkyl amide thereof.
The method of producing hybrid cereal grain seed which comprises treating a female parent of the cereal grain prior to meiosis with a compound of the formula ##STR12## wherein R.sup.1 is an unsubstituted phenyl group or a phenyl group substituted with up to three substituents selected from the group consisting of halogen atoms, (C.sub.1 -C.sub.4) alkyl, (C.sub.1 -C.sub.4) alkoxy, (C.sub.1 -C.sub.4) alkylthio, (C.sub.1 -C.sub.4) alkylsulfinyl, (C.sub.1 -C.sub.4) alkylsulfonyl or trifluoromethyl,
- R.sup.2 is a (C.sub.1 -C.sub.4) alkyl group, or phenyl,
- R.sup.3 is a hydrogen atom, a (C.sub.1 -C.sub.4) alkyl group, or a halogen atom, a benzyl group or a phenethyl group,
- Z is oxygen or sulfur, and
- Y is the group Z'R.sup.4 or NR.sup.5 R.sup.6
- wherein
- Z' is oxygen or sulfur,
- R.sup.4 is hydrogen, (C.sub.1 -C.sub.4) alkyl, (C.sub.1 -C.sub.4) alkoxyalkyl, cyclohexyl, cyclohexylmethyl, bromopropyl, phenyl, or benzyl,
- R.sup.5 and R.sup.6 are independently selected from the group consisting of hydrogen or (C.sub.1 -C.sub.4) alkyl or (C.sub.1 -C.sub.4) alkyl substituted with carboxyl or (C.sub.1 -C.sub.4) alkoxycarbonyl, or when
- R.sup.5 is hydrogen, R.sup.6 is hydroxyl,
- or an agronomically acceptable salt, (C.sub.1 -C.sub.12) alkyl ester or mono or di(C.sub.1 -C.sub.4) alkyl amide thereof.
Dependencies are inferred from the claim text.