Plant protecting and regulating compositions – Seed coated with agricultural chemicals other than fertilizers
Patent
1992-06-25
1994-05-24
Lee, Mary C.
Plant protecting and regulating compositions
Seed coated with agricultural chemicals other than fertilizers
504191, 504193, 504225, 504252, 504271, 544137, 546283, 548110, 548237, 548240, A01N 4340, A01N 4380, C07D41306, C07D26308
Patent
active
053148630
DESCRIPTION:
BRIEF SUMMARY
The invention relates to safeners or antidotes which, in combination with herbicides, can reduce the phytotoxicity of the herbicides in crop plants.
The invention relates to plant-protecting isoxazolines of the formula (I) or salts thereof ##STR2## where the Z radicals independently of one another are halogen, nitro, cyano, or alkyl, alkoxy, alkylthio or cycloalkyl, the four last-mentioned radicals being unsubstituted or monosubstituted or polysubstituted by alkoxy, hydroxyl or halogen, or furthermore are amino, mono- or dialkylamino, phenyl or phenoxy, phenyl and phenoxy independently of one another being unsubstituted or monosubstituted or polysubstituted by halogen or halogenoalkyl, or two adjacent substituents Z together are a divalent group of the formula --OCH.sub.2 O--, --S--CH.sub.2 --O-- or --S--CH.sub.2 --S--, which group is unsubstituted or substituted by alkyl, the five last-mentioned radicals being unsubstituted or monosubstituted or polysubstituted by radicals from the group comprising alkoxy, alkylthio, mono- and dialkylamino, phenyl, substituted phenyl, cyano and halogen, or is furthermore phenoxy or substituted phenoxy, or is furthermore trialkylsilylmethoxy, a radical of the formula ##STR3##
where R in each case is hydrogen or alkyl, Z.sup.1 independently of Z has the meanings mentioned above in the case of Z, and n.sup.1 is an integer from 0 to 5, or is furthermore amino, mono- or dialkylamino, cycloalkylamino, hydrazino, alkyl- or dialkylhydrazino, pyridino, morpholino, dimethylmorpholino, a radical of the formula ##STR4##
where R.sup.1 and R.sup.2 independently of one another are alkyl radicals or R.sup.1 and R.sup.2 together with the carbon atom linking them form a cycloalkyl radical, or is furthermore a radical of the formula ##STR5## where R.sup.3 and R.sup.4 independently of one another are hydrogen or alkyl.
In formula (I), alkyl, alkoxy, haloalkyl, alkylamino and alkylthio radicals and the corresponding unsaturated and/or substituted radicals can be straight-chain or branched in each case. Alkyl radicals, also in the composed meanings such as alkoxy, haloalkyl etc., are methyl, ethyl, n- and i-propyl, n-, i-, t- and 2-butyl, the isomeric pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl and dodecyl radicals, and the longer-chain fatty alkyl radicals which have up to 24 carbon atoms; C.sub.1 -C.sub.12 -alkyl radicals are preferred. Alkenyl and alkynyl radicals have the meanings of the unsaturated radicals which are possible and which correspond to the alkyl radicals, preferably (C.sub.2 -C.sub.12)alkenyl and -alkynyl radicals. Halogen is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.
In the event that X=OH, the compounds of the formula (I) can form salts. The salts which can be employed according to the invention are those which can be used in agriculture. Suitable examples are metal salts such as alkali metal salts or alkaline earth metal salts, in particular sodium or potassium salts, ammonium salts or substituted ammonium salts which are monosubstituted to tetrasubstituted by alkyl and/or alkanol radicals having preferably up to 4 carbon atoms.
Formula (I) furthermore also embraces all stereoisomers and their mixtures, in particular also pure enantiomers and their mixtures (for example racemates). Stereoisomers can occur mainly when asymmetric carbon atoms or suitably substituted double bonds are present in the formula (I). An asymmetric carbon atom is the carbon atom bonded to the oxygen atom in the isoxazoline ring.
The plant-protecting compounds of the formula (I) according to the invention which are of particular interest are those in which -C.sub.4)alkyl, (C.sub.1 -C.sub.4)alkoxy, (C.sub.1 -C.sub.4)-alkylthio, the alkyl, alkoxy and alkylthio groups being unsubstituted or monosubstituted or polysubstituted by halogen atoms, in particular fluorine or chlorine, or are (C.sub.3 -C.sub.6)cycloalkyl which is unsubstituted or substituted by (C.sub.1 -C.sub.4)alkyl, or are amino, (C.sub.1 -C.sub.4)alkylamino,
REFERENCES:
Synthesis 1986, 488-490, Shimizu et al., Synthesis of . . . Dipolarophiles.
Vaughan et al., "5-Phenyl-2-isoxazoline-3-carboxylic Acid", J. Org. Chem. 25:1160-1164 (1960).
Matier et al., "Synthesis and Biological Properties of 5-Aryl-4H-1,2,4-thiadiazine 1,1-Dioxides", Journal of Medicinal Chemistry 17:549-552 (1974).
Kurosawa et al., "Acceleration of the Reductive Elimination Step in Pd-Catalysed Allylic Alkylation by Allylic Substrates", i J. Chem. Soc., Chem. Commun.:968-969 (1984).
CA 102:24531z The Reaction . . . p-toluenesulfonic Acid. Shimizu et al., p. 686, 1985.
CA 106:138304r Synthesis of . . . Dipolarophiles. Shimizu et al., p. 679, 1987.
CA 115:92254e Preparation of . . . Safeners. Loeher et al., p. 765, 1991.
Bauer Klaus
Bieringer Hermann
Loher Heinz J.
Schwab Wilfried
Hoechst Aktiengesellschaft
Lee Mary C.
McKane Joseph K.
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