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US 4,670,041 AGranted
Oxabicycloalkane herbicides
AssigneeE. I. Du Pont de Nemours and Company
InventorsGeorge B. Payne, Samuel B. Soloway, James E. Powell, Steven A. Roman, Willy D. Kollmeyer
Life of this patent
Estimating the term…
Abstract
Compounds of the formula ##STR1## wherein X is (--CR.sub.4 R.sub.4 --).sub.m in which m is 0 or 1; Y is (--CR.sub.5 R.sub.6 --).sub.n in which n is 0, 1 or 2; Z is (--CR.sub.7 R.sub.7 --).sub.p in which p is 1, 2, or 3; the sum of m+n+p is an integer of 2 to 5, inclusive; R.sub.2 and R.sub.3 each is H or alkyl, and the like; R.sub.1 is H or alkyl; and W is an unsaturated moiety, are useful as plant growth regulators and herbicides.
Claims66
A compound of the formula ##STR83## wherein X is (--CR.sub.4 R.sub.4).sub.m in which m is 0 or 1;
- Y is (--CR.sub.5 R.sub.6).sub.n is which n is 0, 1 or 2;
- Z is (--CR.sub.7 R.sub.7).sub.p in which p is 1, 2 or 3;
- the sum of m+n+p is an integer of 2 to 5, inclusive;
- R.sub.1 is a hydrogen atom or an alkyl group containing from 1 to 4 carbon atoms;
- R.sub.2 is a hydrogen atom or a straight-chain alkyl group containing from 1 to 6 carbon atoms;
- R.sub.3 is a hydrogen atom or an alkyl group containing from 1 to 10 carbon atoms;
- a cyano group;
- an alkyl group substituted by:
- a hydroxy group, a cyano group, an alkoxy group containing from 1 to 6 carbon atoms, a C.sub.1-6 alkylsulfonyl group, a C.sub.6-10 arylsulfonyl group, a C.sub.7-11 aralkylsulfonyl group, an azido group, a C.sub.1-6 alkoxycarbonyl group, a hydroxycarbonyl group, a dialkoxyphosphonge group or an amine oxide, carbamoyl or thiocarbamoyl group, each nitrogen atom substitued by hydrogen or by 1 or 2 alkyl groups containing from 1 to 4 carbon atoms;
- or R.sub.3 is an alkenyl or alkynyl group containing 2 to 4 carbon atoms;
- an aryl or aralkyl group, each containing from 6 to 11 carbon atoms including 1 to 4 carbon atoms in the alkyl portion and optionally ring substituted by halogen or by an alkyl or alkoxy group containing from 1 to 2 carbon atoms, each optionally substituted by one or more halogen atoms, or R.sub.3 is a group --CO.sub.2 R.sub.8 ;
- --CON(R.sub.8).sub.2, or --CSNH.sub.2 in which R.sub.8 is a hydrogen atom or an alkyl group containing from 1 to 6 carbon atoms;
- or R.sub.3 is an acyl group containing 1 to 6 carbon atoms or an oxime or an acetal derivative of said acyl group;
- each R.sub.4 is independently a hydrogen atom, an alkyl group containing from 1 to 4 carbon atoms each optionally substituted by up to 3 halogen atoms, a hydroxy group or an alkoxy group containing 1 to 4 carbon atoms;
- or one of R.sub.4 and R.sub.1 when taken together form a carbon-carbon bond;
- R.sub.5 and R.sub.6 each independently is a hydrogen atom, or an alkyl group containing from 1 to 2 carbon atoms;
- or when located on a carbon atom adjacent to the ring oxygen atom then R.sub.5 and R.sub.6 together form an alkylene group containing 4 or 5 carbon atoms;
- each R.sub.7 independently is a hydrogen atom or an alkyl group containing from 1 to 4 carbon atoms optionally substituted by up to 3 halogen atoms;
- or when n is 0 then R.sub.7 is also a chlorine atom, a bromine atom, or two of R.sub.7 when located on adjacent carbon atoms together form an epoxide ring or carbon-carbon bond;
- or when n is 1 then one R.sub.7 on the carbon adjacent to the carbon bearing R.sub.2 is a hydroxy group, a C.sub.7-11 aralkoxy group or an alkoxy group containing 1 to 4 carbon atoms, and the other R.sub.7 is a hydrogen atom;
- both of Q are hydrogen atoms or are fluorine atoms;
- W is an alkenyl or alkynyl group containing up to 4 carbon atoms, or an aromatic or a heterocyclic group containing up to 14 carbon atoms, each optionally substituted by hydroxy, cyano, halogen of atomic number of from 9 to 35, inclusive, alkyl, haloalyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl alkylsulfonyl, alkenyl or alkynyl of up to 4 carbon atoms, or aminocarbonyl, carboxyl, amino or alkanoylamino, each of which hydrogen can be substituted by alkyl of 1 to 4 carbon atoms;
- a cycloalkyl group containing 3 to 10 carbon atoms optionally substituted by alkyl of 1 to 3 carbon atoms;
- a cyclohexenyl group;
- a cyano group;
- or a secondary alkyl group containing 3 to 10 carbon atoms;
- and stereoisomer forms or mixtures thereof.
24 more elements
A compound of the formula I ##STR84## wherein R is a hydrogen atom;
- or a straight-chain alkyl group containing from 1 to 6 carbon atoms;
- R.sub.1 is a hydrogen atom;
- a cyano group;
- or is an alkyl group containing from 1 to 10 carbon atoms optionally substituted by up to 3 halogen atoms, each having an atomic number of from 9 to 35, inclusive, or by a hydroxy group, a cyano group, an alkoxy group containing from 1 to 6 carbon atoms, a C.sub.1-6 alkylsulfonyl group, a C.sub.6-10 arylsulfonyl group, a C.sub.7-11 aralkylsulfonyl group, an azido group, a C.sub.1-6 alkoxycarbonyl group, a hydroxycarbonyl group, a dialkoxyphosphonyl group an amine oxide group, a carbamoyl group, a thiocarbamoyl group substituted by hydrogen or by 1 or 2 alkyl groups containing from 1 to 6 carbon atoms;
- or
- R.sub.1 is an alkenyl or alkynyl group containing from 2 to 4 carbon atoms;
- or is an aryl or aralkyl group, each containing from 6 to 11 carbon atoms, and 1 to 4 carbons in the alkyl portion, each optionally ring-substituted by one or more substituents independently selected from a halogen atom, each having an atomic number of from 9 to 35, inclusive, or by an alkyl or alkoxy group containing from 1 to 2 carbon atoms, each optionally substituted by one or more halogen atoms, each having an atomic number of 9 or 17, or R.sub.1 is a group --CO.sub.2 R.sub.6, --CON(R.sup.6).sub.2, or --CSNH.sub.2 in which R.sub.6 is a hydrogen atom, or an alkyl group containing from 1 to 6 carbon atoms;
- R.sub.2 is an alkenyl or alkynyl group containing from 2 to 4 carbon atoms;
- a 4-pyrimidinyl group;
- a 2-pyrazinyl group;
- a 3-pyridazinyl group;
- a 2-pyridinyl group;
- a 2-furanyl group;
- a naphthyl group or a phenyl group optionally substituted by one or more substituents independently selected from a halogen atom, each having an atomic number of from 9 to 35, inclusive, or an alkoxy, alkylthio or alkylsulfinyl group containing from 1 to 3 carbon atoms, each optionally substituted by one or more halogen atoms, each having an atomic number of 9 or 17, or naphthyl or phenyl substituted by an alkyl group containing 1 or 2 carbon atoms optionally substitued by one or more halogen atoms having an atomic number of 9 or 17, hydroxy, monoor dialkylamino- or alkanoylamino containing 1 or 2 carbon atoms in each alkyl group, alkoxy of 1 or 2 carbon atoms or alkylthio of 1 or 2 carbon atoms, or is a phenyl group substitued by mono- or dialkylamino- or alkanoylamino containing 1 or 2 carbon atoms in each alkyl group or by carboxyl;
- each R.sub.3 is independently selected from a hydrogen atom;
- a chlorine atom;
- a bromine atom;
- or an alkyl group containing from 1 to 4 carbon atoms optionally substituted by up to 3 halogen atoms, each having an atomic number of from 9 to 35, inclusive;
- or two of R.sup.3 when located on adjacent carbon atoms together form an epoxide ring or carbon-carbon bond;
- R.sub.4 is a hydrogen atom;
- or an alkyl group containing from 1 to 4 carbon atoms optionally substituted by up to 3 halogen atoms having an atomic number of from 9 to 35, inclusive;
- each R.sup.5 is independently selected from a hydrogen atom;
- or an alkyl group containing from 1 to 4 carbon atoms, each optionally substituted by up to 3 halogen atoms having an atomic number of from 9 to 35, inclusive, a hydroxy group, or an alkoxy group containing 1 to 4 carbon atoms;
- or
- R.sup.4 and R.sup.5 when taken together form a carbon-carbon bond;
- both of Q are hydrogen atoms or fluorine atoms;
- and stereoisomeric forms or mixtures thereof.
24 more elements
A compound of the formula Ia ##STR85## wherein R is a straight-chain alkyl group containing from 1 to 6 carbon atoms;
- R.sup.1 is an alkyl group containing from 1 to 6 carbon atoms optionally substituted by up to 3 halogen atoms selected independently from fluorine, chlorine and bromine atoms or by OH, CN, an alkoxy group containing from 1 to 6 carbon atoms, a C.sub.1-6 alkylsulfonyl group, a phenylsulfonyl group, a benzylsulfonyl group, or is an aryl or aralkyl group each containing from 6 to 11 carbon atoms, and 1 or 2 carbon atoms in any alkyl portion, optionally substituted by one or more substituents independently selected from halogen atoms having an atomic number of from 9 to 35, inclusive, or by an alkyl or alkoxy group containing from 1 to 2 carbon atoms each optionally substituted by one or more halogen atoms having an atomic number of from 9 to 17;
- and R.sup.2 is an ethynyl group, a 2-pyridinyl group, a 2-furanyl group or a phenyl group optionally substituents by one or more substituents independently selected from a halogen atom having an atomic number of from 9 to 35, inclusive, or by an alkoxy or alkylthio group containing from 1 to 2 carbon atoms each optionally substituted by one or more halogen atoms having an atomic number of 9 or 17, or phenyl substituted by an alkyl group containing 1 or 2 carbon atoms optionally substituted by one or more halogen atoms having an atomic number of 9 or 17, hydroxy, alkoxy of 1 or 2 carbon atoms or alkylthio of 1 or 2 carbon atoms;
- and stereoisomeric forms or mixtures thereof.
A compound of the formula II ##STR86## wherein both of Q are hydrogen atoms or fluorine atoms;
- R is a hydrogen atom;
- or a straight-chain alkyl group containing from 1 to 6 carbon atoms;
- R.sup.1 and R.sup.2 each independently is a hydrogen atom;
- or an alkyl group containing 1 or 2 carbon atoms;
- or R.sup.1 and R.sup.2 taken together form an alkylene group containing 4 or 5 carbon atoms;
- R.sup.3 is a hydrogen atom;
- a hydroxy group;
- a benzyloxy group;
- or an alkoxy group containing 1 or 2 carbon atoms;
- R.sup.4 is an alkenyl or alkynyl group containing from 2 to 4 carbon atoms;
- a 2-pyridinyl group;
- a 2-furanyl group;
- or a phenyl group optionally substituted by one or more substituents independently selected from a cyano group, a halogen atom, each having an atomic number of from 9 to 35, inclusive;
- or an alkoxy or alkylthio group containing from 1 to 3 carbon atoms, each optionally substituted by one or more halogen atoms, each having an atomic number of 9 or 17, or by an alkyl group containing 1 or 2 carbon atoms optionally substituted by one or more halogen atoms having an atomic number of 9 or 17, hydroxy, alkoxy of 1 or 2 carbon atoms or alkylthio of 1 or 2 carbon atoms;
- R.sup.5, R.sup.6, R.sup.7 and each R.sup.8 is each independently is a hydrogen atom;
- or an alkyl group containing from 1 to 4 carbon atoms.
13 more elements
A compound of the formula IIc ##STR87## wherein R is a straight-chain alkyl group containing from 1 to 6 carbon atoms;
- R.sup.1 and R.sup.2 each independently is an alkyl group containing from 1 to 2 carbon atoms or R.sup.1 and R.sup.2 when taken together form a alkylene group containing 4 or 5 carbon atoms;
- R.sup.3 is a hydrogen atom, a hydroxy group, a benzyloxy or an alkoxy group containing 1 or 2 carbon atoms;
- and R.sup.4 is an ethynyl group, a 2-pyridinyl group, a 2-furanyl group or a phenyl group optionally substituted by one or more substituents independently selected from a halogen atom having an atomic number of from 9 to 35, inclusive, or an alkoxy or alkylthio group containing from 1 to 2 carbon atoms each optionally substituted by one or more halogen atoms having an atomic number of 9 or 17, or by an alkyl group containing 1 or 2 carbon atoms optionally substituted by one or more halogen atoms having an atomic number of 9 or 17, hydroxy, alkoxy of 1 or 2 carbon atoms or alkylthio of 1 or 2 carbon atoms.
Dependencies are inferred from the claim text.