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US 5,998,673 AGranted
1, 4-diaryl-2-fluoro-2-butene insecticidal and acaricidal agents
AssigneeAmerican Cyanamid Company
InventorsKeith D. Barnes, Yulin Hu
Life of this patent
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Abstract
Pesticidal 1,4-diaryl-2-fluoro-2-butene compounds having the structural formula I ##STR1## and compositions and methods comprising those compounds for the control of insect and acarid pests.
Claims11
A compound having the structural formula ##STR53## wherein Ar is phenyl optionally substituted with any combination of from one to three halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 haloalkoxy groups, or
- 1- or 2-naphthyl optionally substituted with any combination of from one to three halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 haloalkoxy groups;
- R and R.sub.1 are each independently hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.3 -C.sub.6 cycloalkyl or C.sub.3 -C.sub.6 halocycloalkyl, or R and R.sub.1 taken together with the carbon atom to which they are attached form a C.sub.3 -C.sub.6 cycloalkyl ring optionally substituted with any combination of from one to three halogen or C.sub.1 -C.sub.4 alkyl groups;
- R.sub.2 is hydrogen, Cl, Br, cyano or OR.sub.3 ;
- R.sub.3 is hydrogen or C.sub.1 -C.sub.4 alkyl;
- and
- Ar.sub.1 is phenoxyphenyl optionally substituted with any combination of from, one to six halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 haloalkoxy groups,
- phenyl optionally substituted with any combination of from one to five halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 haloalkoxy groups,
- biphenyl optionally substituted with any combination of from one to five halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 haloalkoxy groups,
- benzylphenyl optionally substituted with any combination of from one to five halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 haloalkoxy groups,
- benzoylphenyl optionally substituted with any combination of from one to five halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 haloalkoxy groups, or
- 1- or 2-naphthyl optionally substituted with any combination of from one to three halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 haloalkoxy groups, or
- the optical isomers thereof, and
- the cis and trans isomers thereof.
10 more elements
A process for the preparation of a compound having the structural formula ##STR55## wherein Ar is phenyl optionally substituted with any combination of from one to three halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 haloalkoxy groups, or
- 1- or 2-naphthyl optionally substituted with any combination of from one to three halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 haloalkoxy groups,
- R and R.sub.1 are each independently C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.3 -C.sub.6 cycloalkyl or C.sub.3 -C.sub.6 halocycloalkyl, or R and R.sub.1 taken together with the carbon atom to which they are attached form a C.sub.3 -C.sub.6 cycloalkyl ring optionally substituted with any combination of from one to three halogen or C.sub.1 -C.sub.4 alkyl groups;
- and
- Ar.sub.1 is phenoxyphenyl optionally substituted with any combination of from, one to six halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 haloalkoxy groups,
- phenyl optionally substituted with any combination of from one to five halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 haloalkoxy groups,
- biphenyl optionally substituted with any combination of from one to five halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 haloalkoxy groups,
- benzylphenyl optionally substituted with any combination of from one to five halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 haloalkoxy groups,
- benzoylphenyl optionally substituted with any combination of from one to five halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 haloalkoxy groups, or
- 1- or 2-naphthyl optionally substituted with any combination of from one to three halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 haloalkoxy groups,
- and the optical isomers thereof, and
- the cis and trans isomers thereof,
- which process comprises reacting a 4-aryl-3-fluoro-2-buten-1-ol having the structural formula ##STR56## wherein Ar, R and R.sub.1 are as described above with a brominating agent to form a 4-aryl-1-bromo-3-fluoro-2-butene having the structural formula ##STR57## wherein Ar, R and R.sub.1 are as described above, and reacting the 4-aryl-1-bromo-3-fluoro-2-butene with about 0.0025 to 0.1 molar equivalent of a palladium catalyst, at least about 2 molar equivalents of a base and a boronic acid having the structural formula
- (HO).sub.2 BAr.sub.1
- wherein Ar.sub.1 is as described above.
11 more elements
A process for the preparation of a compound having the structural formula ##STR58## wherein Ar is phenyl optionally substituted with any combination of from one to three halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 haloalkoxy groups, or
- 1- or 2-naphthyl optionally substituted with any combination of from one to three halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 haloalkoxy groups, or
- R is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.3 -C6cycloalkyl or C.sub.3 -C6halocycloalkyl;
- and
- Ar.sub.1 is phenoxyphenyl optionally substituted with any combination of from, one to six halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 haloalkoxy groups,
- phenyl optionally substituted with any combination of from one to five halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C4haloalkoxy groups,
- biphenyl optionally substituted with any combination of from one to five halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 haloalkoxy groups,
- benzylphenyl optionally substituted with any combination of from one to five halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 haloalkoxy groups,
- benzoylphenyl optionally substituted with any combination of from one to five halogens C.sub.1 -C.sub.4 alkyl C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 haloalkoxy groups, or
- 1- or 2-naphthyl optionally substituted with any combination of from one to three halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C1-C.sub.4 alkoxy or C.sub.1 -C.sub.4 haloalkoxy groups, or
- the optical isomers thereof, and
- the cis and trans isomers thereof,
- which process comprises reacting a 3-aryl-2-fluoro-2-propenal having the structural formula ##STR59## wherein Ar and P are as described above with an ylide having the structural formula ##STR60## wherein Ar.sub.1 is as described above in the presence of a base to form a diene having the structural formula ##STR61## wherein Ar, R and Ar.sub.1 are as described above, and reacting the diene with magnesium in the presence of a protic solvent.
9 more elements
Dependencies are inferred from the claim text.