Etylene derivatives and pesticides containing said derivatives

BACKGROUND OF THE INVENTION
1. Field of the Art
The present invention relates to novel ethylene derivatives, and also to agricultural chemicals and agents for preventing the attachment of aquatic organisms containing said derivatives as an active ingredient. The agricultural chemicals as referred to herein include insecticides, acaricides, nematocides, herbicides and fungicides, etc., and are especially pesticides in the field of agriculture, horticulture, stock farming and sanitation. The agent for preventing the attachment of aquatic organisms are chemicals for preventing the attachment of harmful aquatic organisms such as shells and algae to fishing nets, the bottoms of ships, marine equipment such as buoys, marine constructions, circulating water systems in thermal and atomic power plants, inlet channels for heat exchanger cooling water in chemical industry, underwater constructions and reservoirs.
2. Description of the Related Art
For acrylonitrile derivatives, Japanese Patent Application Laid-Open No. Sho 53-92769 discloses the use of 2'-chloro-3-hydroxy-2-(4-phenyl-2-thiazolyl)-cinnamoyl nitrile as an insecticide; and International Patent Application Laid-Open No. WO-95/29591 discloses its use as an aquatic adhesion inhibitor. Japanese Patent Application Laid-open No. Sho 60-11452 discloses the use of 2-(4-chlorophenyl)-3-(3-pyridyl)-3-oxopropionitrile as a herbicide and Japanese Patent Application Laid-open No. Sho 60-11401 discloses its use as a fungicide.
With the long-term use of insecticides and fungicides, recently, some pests have become resistant to chemicals and are often difficult to exterminate with conventional insecticides and fungicides. In addition, some insecticides are highly toxic and are prone to remain long, without being decomposed, to destroy the ecosystem. Accordingly, it is always expected to develop novel, low-toxic and low-persistent insecticides and fungicides.
On the other hand, in order to prevent the adhesion and growth of marine and freshwater aquatics, it is used antifouling coatings comprising organic tin compounds such as bis(tributyltin) oxide or copper compounds such as copper sulfate and cuprous oxide. However, organic tin compounds are highly toxic, though being effective in preventing the adhesion of aquatics, and are especially prone to accumulate in the bodies of fishes and shellfishes. As so promoting the environmental pollution, the use of those compounds is now under legal controls. Copper compounds are widely used in antifouling coatings for inlet channels and for the bottoms of ships. However, like tin compounds, copper compounds contain a copper as a heavy metal. Therefore, the use of copper compounds will bring about the environmental pollution in future, and agents for preventing the attachment of aquatic organisms comprising such copper compounds are not preferred. Under the above-mentioned situation, it has been desired agents for preventing the attachment of aquatic organisms that have few influences on the ecosystem and bring about little secondary pollution.
SUMMARY OF THE INVENTION
In order to solve the above-mentioned problems, the present inventors have assiduously studied to develop agricultural chemicals and agents for preventing the attachment of aquatic organisms which can exhibit excellent pesticidal activities even when used in small amounts, and which have few negative influences on non-targeted organisms such as mammals, fishes and useful insects, and, as a result, have found that the compounds mentioned hereinunder are highly safe and have excellent pesticidal activities and activities for preventing the attachment of aquatic organisms. On the basis of these findings, the present inventors have completed the present invention.
DETAILED DESCRIPTION OF THE INVENTION
Specifically, the present invention provides the following [1] to [25]
[1] Ethylene derivatives of a formula (I):
[wherein;
Q represents a phenyl group optionally substituted by G, a naphthyl group optionally substituted by G, or a heterocyclic group optionally substituted by R (said heterocyclic group being a thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,4,5-tetrazinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl, thiazolinyl, imidazolinone, imidazolidinedione, 3(2H)-pyridazinone, benzothiazolyl, benzimidazolyl, indazolyl, benzoxazolyl, quinolyl, isoquinolyl, quinoxalinyl, phthalazinyl, cinnolinyl or quinazolinyl group);
A represents a phenyl group optionally substituted by W, a naphthyl group optionally substituted by W, or a heterocyclic group optionally substituted by Y (said heterocyclic group being a thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl, thiazolinyl, 3(2H)-pyridazinone, benzothiazolyl, benzimidazolyl, indazolyl, benzoxazolyl, quinolyl, isoquinolyl, quinoxalinyl, phthalazinyl, cinnolinyl or quinazolinyl group);
provided that, (a) when Q is a thienyl group optionally substituted by R, a furyl group optionally substituted by R, a quinolyl group optionally substituted by R, or an isoquinolyl group optionally substituted by R, then A is a phenyl group optionally substituted by W, a naphthyl group optionally substituted by W, or a heterocyclic group optionally substituted by Y (said heterocyclic group being a pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl, thiazolinyl, 3(2H)-pyridazinone, benzothiazolyl, benzimidazolyl, indazolyl, benzoxazolyl, quinoxalinyl, phthalazinyl, cinnolinyl or quinazolinyl group);
(b) when Q is a 2-thiazolyl group optionally substituted by R, then A is a naphthyl group optionally substituted by W, or a heterocyclic group optionally substituted by Y (said heterocyclic group being a thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl, thiazolinyl, 3(2H)-pyridazinone, benzothiazolyl, benzimidazolyl, indazolyl, benzoxazolyl, quinolyl, isoquinolyl, quinoxalinyl, phthalazinyl, cinnolinyl or quinazolinyl group);
(c) when Q is a pyridyl group optionally substituted by R, then A is a heterocyclic group optionally substituted by Y (said heterocyclic group being a pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyrazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl, thiazolinyl, 3(2H)-pyridazinone, benzothiazolyl, benzimidazolyl, indazolyl, benzoxazolyl, quinoxalinyl, phthalazinyl, cinnolinyl or quinazolinyl group);
(d) when Q is an isothiazolyl group optionally substituted by R, a 1,2,3-triazolyl group optionally substituted by R, or a benzoxazolyl group optionally substituted by R, then A is a naphthyl group optionally substituted by W, or a heterocyclic group optionally substituted by Y (said heterocyclic group being a thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl, thiazolinyl, 3(2H)-pyridazinone, benzothiazolyl, benzimidazolyl, indazolyl, benzoxazolyl, quinolyl, isoquinolyl, quinoxalinyl, phthalazinyl, cinnolinyl or quinazolinyl group);
(e) when Q is a 1,2,4-triazolyl group optionally substituted by R, then A is a heterocyclic group optionally substituted by Y (said heterocyclic group being a thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl, thiazolinyl, 3(2H)-pyridazinone, benzothiazolyl, benzimidazolyl, indazolyl, benzoxazolyl, quinolyl, isoquinolyl, quinoxalinyl, phthalazinyl, cinnolinyl or quinazolinyl group);
(f) when Q is a benzothiazolyl group optionally substituted by R, then A is a naphthyl group optionally substituted by W, or a heterocyclic group optionally substituted by Y (said heterocyclic group being a furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl, thiazolinyl, 3(2H)-pyridazinone, benzothiazolyl, benzimidazolyl, indazolyl, benzoxazolyl, quinolyl, isoquinolyl, quinoxalinyl, phthalazinyl, cinnolinyl or quinazolinyl group);
(g) when Q is a benzimidazolyl group optionally substituted by R, then A is a naphthyl group optionally substituted by W, or a heterocyclic group optionally substituted by Y (said heterocyclic group being a pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyrazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl, thiazolinyl, 3(2H)-pyridazinone, benzothiazolyl, benzimidazolyl, indazolyl, benzoxazolyl, quinolyl, isoquinolyl, quinoxalinyl, phthalazinyl, cinnolinyl or quinazolinyl group);
(h) when Q is a phenyl group optionally substituted by G, then A is a heterocyclic group optionally substituted by Y (said heterocyclic group being a pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl, thiazolinyl, 3(2H)-pyridazinone, benzothiazolyl, benzimidazolyl, indazolyl, benzoxazolyl, quinoxalinyl, phthalazinyl, cinnolinyl or quinazolinyl group);
(i) when Q is a naphthyl group optionally substituted by G, then A is a heterocyclic group optionally substituted by Y (said heterocyclic group being a thienyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl, thiazolinyl, 3(2H)-pyridazinone, benzothiazolyl, benzimidazolyl, indazolyl, benzoxazolyl, quinolyl, isoquinolyl, quinoxalinyl, phthalazinyl, cinnolinyl or quinazolinyl group);
B represents H, a C.sub.1 -C.sub.4 alkyl group, a C.sub.1 -C.sub.4 haloalkyl group, a C.sub.2 -C.sub.4 alkoxyalkyl group, CH.sub.3 SCH.sub.2, CH.sub.3 OC.sub.2 H.sub.4 OCH.sub.2, a C.sub.1 -C.sub.4 alkyl group substituted by a phenyl group optionally substituted by a halogen or a C.sub.1 -C.sub.4 alkyl group, a C.sub.1 -C.sub.4 alkyl group substituted by a benzoyl group optionally substituted by a halogen or a C.sub.1 -C.sub.4 alkyl group, a tetrahydropyranyl group, (CH.sub.3 ).sub.3 Si, a C.sub.1 -C.sub.4 alkylsulfonyl group, a phenylsulfonyl group optionally substituted by a halogen or a C.sub.1 -C.sub.4 alkyl group, --SO.sub.2 CF.sub.3, a C.sub.1 -C.sub.4 monoalkylaminosulfonyl group, a C.sub.2 -C.sub.8 dialkylaminosulfonyl group, a phenylaminosulfonyl group, a C.sub.2 -C.sub.5 monoalkylaminothiocarbonyl group, a C.sub.3 -C.sub.9 dialkylaminothiocarbonyl group, a C.sub.2 -C.sub.5 cyanoalkyl group, a C.sub.3 -C.sub.9 alkoxycarbonylalkyl group, --C(.dbd.O)T.sup.1, --P(.dbd.O)T.sup.2 T.sup.3, --P(.dbd.S)T.sup.2 T.sup.3, an alkali metal atom, an alkaline earth metal atom, or NHT.sup.4 T.sup.5 T.sup.6 ;
provided that, when Q is a 2-thiazolyl or 2-benzothiazolyl group, then B is a C.sub.1 -C.sub.4 alkyl group, a C.sub.1 -C.sub.4 haloalkyl group, a C.sub.2 -C.sub.4 alkoxyalkyl group, CH.sub.3 SCH.sub.2, CH.sub.3 OC.sub.2 H.sub.4 OCH.sub.2, a C.sub.1 -C.sub.4 alkyl group substituted by a phenyl group optionally substituted by a halogen or a C.sub.1 -C.sub.4 alkyl group, a C.sub.1 -C.sub.4 alkyl group substituted by a benzoyl group optionally substituted by a halogen or a C.sub.1 -C.sub.4 alkyl group, a tetrahydropyranyl group, (CH.sub.3).sub.3 Si, a C.sub.1 -C.sub.4 alkylsulfonyl group, a phenylsulfonyl group optionally substituted by a halogen or a C.sub.1 -C.sub.4 alkyl group, --SO.sub.2 CF.sub.3, a C.sub.1 -C.sub.4 monoalkylaminosulfonyl group, a C.sub.2 -C.sub.8 dialkylaminosulfonyl group, a phenylaminosulfonyl group, a C.sub.2 -C.sub.5 monoalkylaminothiocarbonyl group, a C.sub.3 -C.sub.9 dialkylaminothiocarbonyl group, a C.sub.2 -C.sub.5 cyanoalkyl group, a C.sub.3 -C.sub.9 alkoxycarbonylalkyl group, --C(.dbd.O)T.sup.1, --P(.dbd.O)T.sup.2 T.sup.3, or --P(.dbd.S)T.sup.2 T.sup.3 ;
E represents a heterocyclic group optionally substituted by a C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 haloalkyl group--(said heterocyclic group being a 2-oxazolyl, 2-thiazolyl, 2-imidazolyl, 1,2,4-triazol-3-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-thiadiazol-3-yl, 1,3,4-oxadiazol-2-yl, 5-tetrazolyl, 2-oxazolinyl or 1,2,4,5-tetrazin-3-yl group) - or represents a halogen, a C.sub.2 -C.sub.4 alkynyl group, a phenylethynyl group optionally substituted by Z, a C.sub.1 -C.sub.4 haloalkyl group, CN, an isonitrile group, NO.sub.2, N.sub.3, CHO, a C.sub.2 -C.sub.5 alkylcarbonyl group, a C.sub.2 -C.sub.5 alkoxycarbonyl group, a C.sub.3 -C.sub.5 alkenyloxycarbonyl group, a C.sub.2 -C.sub.4 alkylaminocarbonyl group, a C.sub.3 -C.sub.9 dialkylaminocarbonyl group, a benzoyl group optionally substituted by Z, an aminothiocarbonyl group, a C.sub.1 -C.sub.4 alkylsulfenyl group, a C.sub.1 -C.sub.4 alkylsulfinyl group, a C.sub.1 -C.sub.4 alkylsulfonyl group, a phenylsulfenyl group optionally substituted by Z, a phenylsulfinyl group optionally substituted by Z, a phenylsulfonyl group optionally substituted by Z, --P(.dbd.O)T.sup.2 T.sup.3, or --P(.dbd.S)T.sup.2 T.sup.3.
G is a substituent freely selected from a halogen atom, a C.sub.1 -C.sub.10 alkyl group, a C.sub.2 -C.sub.4 cyanoalkyl group, a C.sub.1 -C.sub.4 alkyl group substituted by a phenyl group optionally substituted by a halogen or a C.sub.1 -C.sub.4 alkyl group, a C.sub.2 -C.sub.4 alkenyl group, a C.sub.2 -C.sub.6 alkynyl group, a C.sub.1 -C.sub.6 haloalkyl group, a C.sub.2 -C.sub.6 haloalkenyl group, a C.sub.2 -C.sub.6 haloalkynyl group, a C.sub.3 -C.sub.6 halocycloalkyl group, a C.sub.3 -C.sub.6 cycloalkyl group optionally substituted by a C.sub.1 -C.sub.3 alkyl group, a C.sub.1 -C.sub.10 alkoxy group, a C.sub.2 -C.sub.6 alkenyloxy group, a C.sub.2 -C.sub.6 alkynyloxy group, a C.sub.1 -C.sub.4 haloalkoxy group, a C.sub.2 -C.sub.6 haloalkenyloxy group, a C.sub.2 -C.sub.6 haloalkynyloxy group, a C.sub.1 -C.sub.4 alkylsulfenyl group, a C.sub.1 -C.sub.4 alkylsulfinyl group, a C.sub.1 -C.sub.4 alkylsulfonyl group, a C.sub.2 -C.sub.6 alkenylsulfenyl group, a C.sub.2 -C.sub.6 alkenylsulfinyl group, a C.sub.2 -C.sub.6 alkenylsulfonyl group, a C.sub.2 -C.sub.6 alkynylsulfenyl group, a C.sub.2 -C.sub.6 alkynylsulfinyl group, a C.sub.2 -C.sub.6 alkynylsulfonyl group, a C.sub.1 -C.sub.4 haloalkylsulfenyl group, a C.sub.1 -C.sub.4 haloalkylsulfinyl group, a C.sub.1 -C.sub.4 haloalkylsulfonyl group, a C.sub.2 -C.sub.6 haloalkenylsulfenyl group, a C.sub.2 -C.sub.6 haloalkenylsulfinyl group, a C.sub.2 -C.sub.6 haloalkenylsulfonyl group, a C.sub.2 -C.sub.6 haloalkynylsulfenyl group, a C.sub.2 -C.sub.6 haloalkynylsulfinyl group, a C.sub.2 -C.sub.6 haloalkynylsulfonyl group, CHO, NO.sub.2, CN, --NU.sup.1 U.sup.2, OH, a naphthyl group, a methoxygroup substituted by a phenyl group optionally substituted by a halogen or a C.sub.1 -C.sub.4 alkyl group, a C.sub.2 -C.sub.7 alkoxycarbonyl group, a C.sub.2 -C.sub.4 alkoxyalkyl group, a C.sub.2 -C.sub.4 alkylcarbonyl group, a C.sub.2 -C.sub.4 haloalkylcarbonyl group, a C.sub.2 -C.sub.5 alkylcarbonyloxy group, a C.sub.2 -C.sub.5 haloalkylcarbonyloxy group, a C.sub.3 -C.sub.7 dialkylaminocarbonyloxy group, a phenyl group optionally substituted by Z, a phenoxy group optionally substituted by Z, a benzoyl group optionally substituted by Z, a pyridyl group optionally substituted by Z, a pyridyloxy group optionally substituted by Z, a thienyl group optionally substituted by Z, a methylenedioxy group as bonded at the adjacent substituting positions, a halomethylenedioxy group as bonded at the adjacent substituting positions, and --N.dbd.CT.sup.7 T.sup.8 (in which T.sup.7 and T.sup.8 each independently represent H, or a phenyl, benzyl or C.sub.1 -C.sub.6 alkyl group, or T.sup.7 and T.sup.8, together with the carbon atom to which they are bonded, form a 5-, 6-, 7- or 8-membered ring), (provided that when the the substituent is two or more, then said substituents may be the same or different), and the number of the substituent, G, is 1, 2, 3 or 4; or G is an alkylene group as bonded to the adjacent substituting positions to form a 5-, 6-, 7- or 8-membered ring;
R is a substituent freely selected from a halogen atom, a C.sub.1 -C.sub.10 alkyl group, a C.sub.1 -C.sub.4 alkyl group substituted by a phenyl group optionally substituted by a halogen or a C.sub.1 -C.sub.4 alkyl group, a C.sub.2 -C.sub.8 alkenyl group, a C.sub.2 -C.sub.6 alkynyl group, a C.sub.1 -C.sub.6 haloalkyl group, a C.sub.2 -C.sub.6 haloalkenyl group, a C.sub.2 -C.sub.6 haloalkynyl group, a C.sub.3 -C.sub.6 halocycloalkyl group, a C.sub.3 -C.sub.6 cycloalkyl group optionally substituted by a C.sub.1 -C.sub.3 alkyl group, a C.sub.1 -C.sub.6 alkoxy group, a C.sub.2 -C.sub.6 alkenyloxy group, a C.sub.2 -C.sub.6 alkynyloxy group, a C.sub.1 -C.sub.4 haloalkoxy group, a C.sub.2 -C.sub.6 haloalkenyloxy group, a C.sub.2 -C.sub.6 haloalkynyloxy group, a C.sub.1 -C.sub.4 alkylsulfenyl group, a C.sub.1 -C.sub.4 alkylsulfinyl group, a C.sub.1 -C.sub.4 alkylsulfonyl group, a C.sub.2 -C.sub.6 alkenylsulfenyl group, a C.sub.2 -C.sub.6 alkenylsulfinyl group, a C.sub.2 -C.sub.6 alkenylsulfonyl group, a C.sub.2 -C.sub.6 alkynylsulfenyl group, a C.sub.2 -C.sub.6 alkynylsulfinyl group, a C.sub.2 -C.sub.6 alkynylsulfonyl group, a C.sub.1 -C.sub.4 haloalkylsulfenyl group, a C.sub.1 -C.sub.4 haloalkylsulfinyl group, a C.sub.1 -C.sub.4 haloalkylsulfonyl group, a C.sub.2 -C.sub.6 haloalkenylsulfenyl group, a C.sub.2 -C.sub.6 haloalkenylsulfinyl group, a C.sub.2 -C.sub.6 haloalkenylsulfonyl group, a C.sub.2 -C.sub.6 haloalkynylsulfenyl group, a C.sub.2 -C.sub.6 haloalkynylsulfinyl group, a C.sub.2 -C.sub.6 haloalkynylsulfonyl group, NO.sub.2, CN, --NU.sup.1 U.sup.2, a phenoxy group, OH, a naphthyl group, a C.sub.2 -C.sub.7 alkoxycarbonyl group, a C.sub.2 -C.sub.4 alkoxyalkyl group, a C.sub.2 -C.sub.4 alkylcarbonyl group, a C.sub.2 -C.sub.5 alkylcarbonyloxy group, a C.sub.2 -C.sub.5 haloalkylcarbonyloxy group, a benzoyl group optionally substituted by X, a phenyl group optionally substituted by X, a pyridyl group optionally substituted by X, a thienyl group optionally substituted by X, and --N.dbd.CT.sup.7 T.sup.8, (provided that when the substituent is two or more, then said substituents may be the same or different), and the number of the substituents, R, is 1, 2, 3 or 4; or R is an alkylene group as bonded to the adjacent substituting positions to form a 5-, 6-, 7- or 8-membered ring;
Y is a substituent freely selected from a halogen atom, a C.sub.1 -C.sub.10 alkyl group, a C.sub.1 -C.sub.6 haloalkyl group, a C.sub.1 -C.sub.6 alkoxy group, a C.sub.2 -C.sub.6 alkenyloxy group, a C.sub.2 -C.sub.6 alkynyloxy group, a C.sub.1 -C.sub.4 haloalkoxy group, a C.sub.2 -C.sub.6 haloalkenyloxy group, a C.sub.2 -C.sub.6 haloalkynyloxy group, a C.sub.1 -C.sub.4 alkylsulfenyl group, a C.sub.1 -C.sub.4 alkylsulfinyl group, a C.sub.1 -C.sub.4 alkylsulfonyl group, a C.sub.2 -C.sub.6 alkenylsulfenyl group, a C.sub.2 -C.sub.6 alkenylsulfinyl group, a C.sub.2 -C.sub.6 alkenylsulfonyl group, a C.sub.2 -C.sub.6 alkynylsulfenyl group, a C.sub.2 -C.sub.6 alkynylsulfinyl group, a C.sub.2 -C.sub.6 alkynylsulfonyl group, a C.sub.1 -C.sub.4 haloalkylsulfenyl group, a C.sub.1 -C.sub.4 haloalkylsulfinyl group, a C.sub.1 -C.sub.4 haloalkylsulfonyl group, a C.sub.2 -C.sub.6 haloalkenylsulfenyl group, a C.sub.2 -C.sub.6 haloalkenylsulfinyl group, a C.sub.2 -C.sub.6 haloalkenylsulfonyl group, a C.sub.2 -C.sub.6 haloalkynylsulfenylgroup, a C.sub.2 -C.sub.6 haloalkynylsulfinyl group, a C.sub.2 -C.sub.6 haloalkynylsulfonyl group, NO.sub.2, CN, --NU.sup.1 U.sup.2, OH, a C.sub.2 -C.sub.7 alkoxycarbonyl group, a C.sub.2 -C.sub.4 alkoxyalkyl group , a C.sub.2 -C.sub.6 alkylcarbonyloxy group, a C.sub.2 -C.sub.5 haloalkylcarbonyloxy group, a C.sub.3 -C.sub.7 dialkylaminocarbonyloxy group, a phenyl group optionally substituted by X, and --N.dbd.CT.sup.7 T.sup.8 (in which T.sup.7 and T.sup.8 each independently represent H, or a phenyl, benzyl or C.sub.1 -C.sub.6 alkyl group, or T.sup.7 and T.sup.8 may, together with the carbon atom to which they are bonded, form a 5-, 6-, 7- or 8-membered ring), (provided that when the substituent is two or more, then said substituents may be the same or different), and the number of the substituent, Y, is 1, 2, 3 or 4; or Y is an alkylene groupas bonded to the adjacent substituting positions to form a 5-,6-, 7- or 8-membered ring;
W is a substituent freely selected from a halogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.4 haloalkyl group, a C.sub.1 -C.sub.4 alkoxy group, a C.sub.1 -C.sub.4 haloalkoxy group, a C.sub.1 -C.sub.4 alkylsulfenyl group, a C.sub.1 -C.sub.4 alkylsulfinyl group, a C.sub.1 -C.sub.4 alkylsulfonyl group, a C.sub.1 -C.sub.4 haloalkylsulfenyl group, a C.sub.1 -C.sub.4 haloalkylsulfinyl group, a C.sub.1 -C.sub.4 haloalkylsulfonyl group, a C.sub.2 -C.sub.4 alkenyl group, a C.sub.2 -C.sub.4 haloalkenyl group, a C.sub.2 -C.sub.4 alkenyloxy group, a C.sub.2 -C.sub.4 haloalkenyloxy group, a C.sub.2 -C.sub.4 alkenylsulfenyl group, a C.sub.2 -C.sub.4 alkenylsulfinyl group, a C.sub.2 -C.sub.4 alkenylsulfonyl group, a C.sub.2 -C.sub.4 haloalkenylsulfenyl group, a C.sub.2 -C.sub.4 haloalkenylsulfinyl group, a C.sub.2 -C.sub.4 haloalkenylsulfonyl group, a C.sub.2 -C.sub.4 alkynyl group, a C.sub.2 -C.sub.4 haloalkynyl group, a C.sub.2 -C.sub.4 alkynyloxy group, a C.sub.2 -C.sub.4 haloalkynyloxy group, a C.sub.2 -C.sub.4 alkynylsulfenyl group, a C.sub.2 -C.sub.4 alkynylsulfinyl group, a C.sub.1 -C.sub.4 alkynylsulfonyl group, a C.sub.2 -C.sub.4 haloalkynylsulfenyl group, a C.sub.2 -C.sub.4 haloalkynylsulfinyl group, a C.sub.2 -C.sub.4 haloalkynylsulfonyl group, NO.sub.2, CN, a formyl group, a C.sub.2 -C.sub.6 alkoxycarbonyl group, a C.sub.2 -C.sub.6 alkylcarbonyl group, a C.sub.2 -C.sub.6 haloalkylcarbonyl group, a C.sub.2 -C.sub.6 alkylcarbonyloxy group, and --NU.sup.1 U.sup.2, (provided that when the substituent is two or more, then said substituents may be the same or different), and the number of the substituent, W, is 1, 2, 3 or 4;
T.sup.1 represents a C.sub.1 -C.sub.20 alkyl group, a C.sub.2 -C.sub.6 alkenyl group, a C.sub.1 -C.sub.6 haloalkyl group, a C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C.sub.4 alkyl group, a C.sub.3 -C.sub.6 halocycloalkyl group, a C.sub.1 -C.sub.4 alkyl group substituted by a phenyl group optionally substituted by a halogen or a C.sub.1 -C.sub.4 alkyl group, a C.sub.3 -C.sub.6 cycloalkyl group optionally substituted by a C.sub.1 -C.sub.3 alkyl group, a cycloalkyl group substituted by a phenyl group optionally substituted by a halogen or a C.sub.1 -C.sub.3 alkyl group, a cyclopropyl group substituted by both a phenyl group optionally substituted by a halogen or a C.sub.1 -C.sub.4 alkyl group and a C.sub.1 -C.sub.4 alkyl group, a C.sub.3 -C.sub.4 cycloalkyl group substituted by both a phenyl group optionally substituted by a halogen or a C.sub.1 -C.sub.4 alkoxy group, and a halogen, a cyclopropyl group substituted by both a C.sub.2 -C.sub.4 alkenyl group optionally substituted by a halogen, and a C.sub.1 -C.sub.4 alkyl group, a C.sub.2 -C.sub.4 alkenyl group substituted by a phenyl group optionally substituted by a halogen or a C.sub.1 -C.sub.4 alkyl group, a C.sub.1 -C.sub.12 alkoxy group, a C.sub.1 -C.sub.4 haloalkoxy group, a C.sub.2 -C.sub.5 alkenyloxy group, a C.sub.3 -C.sub.6 cycloalkoxy group optionally substituted by a C.sub.1 -C.sub.3 alkyl group, a benzyloxy group, a C.sub.2 -C.sub.6 alkoxycarbonyl group, --NU.sup.1 U.sup.2, a phenylamino group, a phenyl group optionally substituted by Z, a phenoxy group optionally substituted by Z, a phenylthio group optionally substituted by Z, a naphthyl group optionally substituted by Z, or a 5-membered or 6-membered heterocyclic group optionally substituted by Z, (said heterocyclic group being selected from thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1.2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl, thiazolinyl and 3(2H)-pyridazinone groups);
T.sup.2 and T.sup.3 each independently represent OH, a phenyl group, a C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkoxy group, or a C.sub.1 -C.sub.4 alkylsulfenyl group;
T.sup.4, T.sup.6 and T.sup.8 each independently represent H, a C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkenyl group, a C.sub.3 -C.sub.6 cycloalkyl group optionally substituted by a C.sub.1 -C.sub.3 alkyl group, or a benzyl group; or any two of T.sup.4, T.sup.5 and T.sup.6 may, together with the nitrogen atom to which they are bonded, form a 5-, 6-, 7- or 8-membered cyclic group optionally containing oxygen, nitrogen and/or sulfur atoms;
X and Z are independently substituents as freely selected from a halogen atom, a C.sub.1 -C.sub.4 alkyl group, a C.sub.1 -C.sub.4 haloalkyl group, a C.sub.1 -C.sub.4 alkoxy group, a C.sub.1 -C.sub.4 haloalkoxy group, a C.sub.1 -C.sub.4 alkylsulfenyl group, a C.sub.1 -C.sub.4 alkylsulfinyl group, a C.sub.1 -C.sub.4 alkylsulfonyl group, a C.sub.2 -C.sub.5 alkenylsulfenyl group, a C.sub.2 -C.sub.5 alkenylsulfinyl group, a C.sub.2 -C.sub.5 alkenylsulfonyl group, a C.sub.1 -C.sub.4 haloalkylsulfenyl group, a C.sub.1 -C.sub.4 haloalkylsulfinyl group, a C.sub.1 -C.sub.4 haloalkylsulfonyl group, NO.sub.2, CN, CHO, OH, --NU.sup.1 U.sup.2, a phenyl group, a phenoxy group, and a C.sub.2 -C.sub.5 alkoxycarbonyl group, (provided that when the substituent is two or more, then said substituents may be the same or different), and the number of the substituent, X and Z, is 1, 2, 3, 4 or 5 each;
T.sup.7 and T.sup.8 each independently represent H, or a phenyl, benzyl or C.sub.1 -C.sub.6 alkyl group, or T.sup.7 and T.sup.8 may, together with the carbon atom to which they are bonded, form a 5-, 6-, 7- or 8-membered ring; and
U.sup.1 and U.sup.2 each independently represent H, a C.sub.1 -C.sub.6 alkyl, C.sub.2 -C, alkylcarbonyl, phenyl or benzyl group, or U.sup.1 and U.sup.2 may, together with the nitrogen atom to which they are bonded, form a 5-, 6-, 7- or 8-membered ring.
[2] Ethylene derivatives of the above-mentioned 1], in which;
Q is a phenyl group optionally substituted by G, a naphthyl group optionally substituted by G, or a heterocyclic group optionally substituted by R, (said heterocyclic group being a thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,4,5-tetrazinyl, pyrazolinyl, imidazolinyl, imidazolinone or imidazolidinedione group;
A is a phenyl group optionally substituted by W, a naphthyl group optionally substituted by W, or a heterocyclic group optionally substituted by Y, said heterocyclic group being a thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, pyrazolinyl or imidazolinyl group;
B is H, a C.sub.1 -C.sub.4 alkyl group, a C.sub.1 -C.sub.4 haloalkyl group, a C.sub.2 -C.sub.4 alkoxyalkyl group, CH.sub.3 OC.sub.2 H.sub.4 OCH.sub.2, a C.sub.1 -C.sub.4 alkylsulfonyl group, a phenylsulfonyl group optionally substituted by a halogen or a C.sub.1 -C.sub.4 alkyl group, --SO.sub.2 CF.sub.3, a C.sub.1 -C.sub.8 dialkylaminosulfonyl group, a C.sub.2 -C.sub.9 dialkylaminothiocarbonyl group, a C.sub.3 -C.sub.9 alkoxycarbonylalkyl group, --C(.dbd.O)T.sup.1, --P(.dbd.O)T.sup.2 T.sup.8, --P(.dbd.S)T.sup.2 T.sup.3, an alkali metal atom, an alkaline earth metal atom, or NHT.sup.4 T.sup.5 T.sup.6 ; and
T.sup.1 is a C.sub.1 -C.sub.2 O alkyl group, a C.sub.2 -C.sub.6 alkenyl group, a C.sub.1 -C.sub.4 haloalkyl group, a C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C.sub.4 alkyl group, a C.sub.1 -C.sub.4 alkyl group substituted by a phenyl group optionally substituted by a halogen or a C.sub.1 -C.sub.4 alkyl group, a C.sub.3 -C.sub.6 halocycloalkyl group, a C.sub.3 -C.sub.6 cycloalkyl group optionally substituted by a C.sub.1 -C.sub.3 alkyl group, a cycloalkyl group substituted by a phenyl group optionally substituted by a halogen or a C.sub.1 -C.sub.4 alkyl group, a cyclopropyl group substituted by both a phenyl optionally substituted by a halogen or a C.sub.1 -C.sub.4 alkyl group, and a C.sub.1 -C.sub.4 alkyl group, a C.sub.3 -C.sub.4 cycloalkyl group substituted by both a phenyl group optionally substituted by a halogen or a C.sub.1 -C.sub.4 alkoxy group and a halogen, a cyclopropyl group substituted by both a C.sub.2 -C.sub.4 alkenyl group optionally substituted by a halogen and a C.sub.1 -C.sub.4 alkyl group, a C.sub.2 -C.sub.4 alkenyl group substituted by a phenyl group optionally substituted by a halogen or a C.sub.1 -C.sub.4 alkyl group, a C.sub.1 -C.sub.12 alkoxy group, a C.sub.1 -C.sub.4 haloalkoxy group, a C.sub.2 -C.sub.5 alkenyloxy group, a C.sub.3 -C.sub.6 cycloalkoxy group optionally substituted by a C.sub.1 -C.sub.3 alkyl group, a benzyloxy group, a C.sub.2 -C.sub.6 alkoxycarbonyl group, a phenyl group optionally substituted by Z, a phenoxy group optionally substituted by Z, a phenylthio group, a naphthyl group, or a heterocyclic group optionally substituted by Z, said heterocyclic group being selected from thienyl, furyl, oxazolyl, thiazolyl, pyrazolyl and pyridinyl groups.
[3] Ethylene derivatives of the above-mentioned [2], in which;
Q is a phenyl group optionally substituted by G, a naphthyl group optionally substituted by G, or a heterocyclic group optionally substituted by R, said heterocyclic group being ##STR2##
A is a phenyl group optionally substituted by W, a naphthyl group optionally substituted by W, or a heterocyclic group optionally substituted by Y, said heterocyclic group being ##STR3## provided that, when (a) Q is any of Q-1, Q-2, Q-3 or Q-4, then A is a phenyl group optionally substituted by W, a naphthyl group optionally substituted by W, or a heterocyclic group optionally substituted by Y, (said heterocyclic group being any of A-5, A-6, A-7, A-8, A-9, A-10, A-11, A-12, A-13, A-14, A-15, A-16, A-17, A-18, A-19, A-20, A-21, A-22, A-23, A-24, A-25, A-26, A-27, A-28, A-29, A-30, A-31, A-32, A-33, A-34, A-35, A-36, A-37, A-38, A-39, A-40, A-41, A-42, A-43, A-44, A-45, A-46, A-47, A-48, A-49, A-50, A-51, A-52, A-53, A-57, A-58, A-59, A-60, A-61, A-62, A-63, A-64, A-65, A-66, A-67, A-68, A-69, A-70, A-71, A-72, A-73, A-74 or A-75),
(b) when Q is Q-12, then A is a naphthyl group optionally substituted by W, or a heterocyclic group optionally substituted by Y, (said heterocyclic group being any of A-1, A-2, A-3, A-4, A-5, A-6, A-7, A-8, A-9, A-10, A-11, A-12, A-13, A-14, A-15, A-16, A-17, A-18, A-19, A-20, A-21, A-22, A-23, A-24, A-25, A-26, A-27, A-28, A-29, A-30, A-31, A-32, A-33, A-34, A-35, A-36, A-37, A-38, A-39, A-40, A-41, A-42, A-43, A-44, A-45, A-46, A-47, A-48, A-49, A-50, A-51, A-52, A-53, A-54, A-55, A-56, A-57, A-58, A-59, A-60, A-61, A-62, A-63, A-64, A-65, A-66, A-67, A-68, A-69, A-70, A-71, A-72, A-73, A-74 or A-75),
(c) when Q is any of Q-52, Q-53 or Q-54, then A is a heterocyclic group optionally substituted by Y, (said heterocyclic group being any of A-5, A-6, A-7, A-8, A-9, A-10, A-11, A-12, A-13, A-14, A-15, A-16, A-17, A-18, A-19, A-20, A-21, A-22, A-23, A-24, A-25, A-26, A-27, A-28, A-29, A-30, A-31, A-32, A-33, A-34, A-35, A-36, A-37, A-38, A-39, A-40, A-41, A-42, A-43, A-44, A-45, A-46, A-47, A-48, A-49, A-50, A-51, A-52, A-53, A-60, A-63, A-64, A-65, A-66, A-67, A-68, A-69, A-70, A-71, A-72, A-73, A-74 or A-75),
(d) when Q is any of Q-23, Q-24, Q-43, Q-44, Q-45, Q-46 or Q-49, then A is a naphthyl group optionally substituted by W, or a heterocyclic group optionally substituted by Y, (said heterocyclic group being any of A-1, A-2, A-3, A-4, A-5, A-6, A-7, A-8, A-9, A-10, A-11, A-12, A-13, A-14, A-15, A-16, A-17, A-18, A-19, A-20, A-21, A-22, A-23, A-24, A-25, A-26, A-27, A-28, A-29, A-30, A-31, A-32, A-33, A-34, A-35, A-36, A-37, A-38, A-39, A-40, A-41, A-42, A-43, A-44, A-45, A-46, A-47, A-48, A-49, A-50, A-51, A-52, A-53, A-54, A-55, A-56, A-57, A-58, A-59, A-60, A-61, A-62, A-63, A-64, A-65, A-66, A-67, A-68, A-69, A-70, A-71, A-72, A-73, A-74 or A-75),
(e) when Q is any of Q-37, Q-38, Q-39, Q-40, Q-41 or Q-42, then A is a heterocyclic group optionally substituted by Y, (said heterocyclic group being any of A-1, A-2, A-3, A-4, A-5, A-6, A-7, A-8, A-9, A-10, A-11, A-12, A-13, A-14, A-15, A-16, A-17, A-18, A-19, A-20, A-21, A-22, A-23, A-24, A-25, A-26, A-27, A-28, A-29, A-30, A-31, A-32, A-33, A-34, A-35, A-36, A-37, A-38, A-39, A-40, A-41, A-42, A-43, A-44, A-45, A-46, A-47, A-48, A-49, A-50, A-51, A-52, A-53, A-57, A-58, A-59, A-60, A-61, A-62, A-63, A-64, A-65, A-66, A-67, A-68, A-69, A-70, A-71, A-72, A-73, A-74 or A-75),
(f) when Q is a phenyl group optionally substituted by G, then A is a heterocyclic group optionally substituted by Y, said heterocyclic group being any of A-5, A-6, A-7, A-8, A-9, A-10, A-11, A-12, A-13, A-14, A-19, A-20, A-21, A-22, A-23, A-24, A-25, A-26, A-27, A-28, A-29, A-30, A-31, A-32, A-33, A-34, A-35, A-36, A-37, A-38, A-39, A-40, A-41, A-42, A-43, A-44, A-45, A-46, A-47, A-48, A-49, A-50, A-51, A-52, A-53, A-60, A-61, A-62, A-63, A-64, A-65, A-66, A-67, A-68, A-69, A-70, A-71, A-72, A-73, A-74 or A-75,
(g) when Q is a naphthyl group optionally substituted by G, then A is a heterocyclic group optionally substituted by Y, (said heterocyclic group being any of A-1, A-2, A-5, A-6,A-7, A-8, A-9, A-10, A-11, A-12, A-13, A-14, A-15, A-16, A-17, A-18, A-19, A-20, A-21, A-22, A-23, A-24, A-25, A-26, A-27, A-28, A-29, A-30, A-31, A-32, A-33, A-34, A-35, A-36, A-37, A-38, A-39, A-40, A-41, A-42, A-43, A-44, A-45, A-46, A-47, A-48, A-49, A-50, A-51, A-52, A-53, A-54, A-55, A-56, A-57, A-58, A-59, A-60, A-61, A-62, A-63, A-64, A-65, A-66, A-67, A-68, A-69, A-70, A-71, A-72, A-73, A-74 or A-75,
R.sup.1 is selected from a halogen atom, a C.sub.1 -C.sub.10 alkyl group, a C.sub.2 -C.sub.6 alkenyl group, a C.sub.2 -C.sub.6 alkynyl group, a C.sub.1 -C.sub.6 haloalkyl group, a C.sub.1 -C.sub.6 alkoxy group, a C.sub.2 -C.sub.6 alkenyloxy group, NO.sub.2, CN, --NU.sup.1 U.sup.2, OH, a C.sub.2 -C.sub.7 alkoxycarbonyl group, a C.sub.2 -C.sub.4 alkoxyalkyl group, a C.sub.2 -C.sub.4 alkylcarbonyl group, a phenyl group optionally substituted by X, a pyridyl group optionally substituted by X, a thienyl group optionally substituted by X, and --N.dbd.CT.sup.7 T.sup.8 (in which T.sup.7 and T.sup.8 each independently represent H, a phenyl, benzyl or C,-C, alkyl group, or T.sup.7 and T.sup.8 may, together with the carbon atom to which they are bonded, form a 5-, 6-, 7- or 8-membered ring); or may, together with the adjacent R, form a 5-, 6-, 7- or 8-membered ring as an alkylene group
Y.sup.1 is selected from a halogen atom, a C.sub.1 -C.sub.10 alkyl group, a C.sub.1 -C.sub.6 haloalkyl group, a C.sub.1 -C.sub.6 alkoxy group, a C.sub.2 -C.sub.6 alkenyloxy group, NO.sub.2, CN, --NU.sup.1 U.sup.2, OH, a C.sub.2 -C.sub.7 alkoxycarbonyl group, a C.sub.2 -C.sub.4 alkoxyalkyl group, a phenyl group optionally substituted by X, and --N.dbd.CT.sup.7 T.sup.8 (in which T.sup.7 and T.sup.8 each independently represent H, or a phenyl, benzyl or C.sub.1 -C.sub.6 alkyl group, or T.sup.7 and T.sup.8 may, together with the carbon atom to which they are bonded), form a 5-, 6-, 7- or 8-membered ring); or may, togeher with the adjacent Y.sup.1, form a 5-, 6-, 7- or 8-membered ring an alkylene group;
X is a substituent of which the number is from 1 to 4 and which is freely selected from a halogen atom, a C.sub.1 -C.sub.4 alkyl group, a C.sub.1 -C.sub.4 haloalkyl group, a C.sub.1 -C.sub.4 alkoxy group, a C.sub.1 -C.sub.4 haloalkoxy group, a C.sub.1 -C.sub.4 alkylsulfenyl group, a C.sub.1 -C.sub.4 alkylsulfinyl group, a C.sub.1 -C.sub.4 alkylsulfonyl group, a C.sub.2 -C.sub.5 alkenylsulfenyl group, a C.sub.2 -C.sub.5 alkenylsulfinyl group, a C.sub.2 -C.sub.5 alkenylsulfonyl group, a C.sub.1 -C.sub.4 haloalkylsulfenyl group, a C.sub.1 -C.sub.4 haloalkylsulfinyl group, a C.sub.1 -C.sub.4 haloalkylsulfonyl group, NO.sub.2, CN, CHO, OH, --NU.sup.1 U.sup.2, a phenyl group, a phenoxy group, and a C.sub.2 -C.sub.5 alkoxycarbonyl group, (provided that when the number of the substituent, X, is two or more then said substituents may be the same or different);
Z is a substituent of which the number is from 1 to 4 and which is freely selected from a halogen atom, a C.sub.1 -C.sub.4 alkyl group, a C.sub.1 -C.sub.4 haloalkyl group, a C.sub.1 -C.sub.4 alkoxy group, a C.sub.1 -C.sub.4 haloalkoxy group, a C.sub.1 -C.sub.4 alkylsulfenyl group, a C.sub.1 -C.sub.4 alkylsulfinyl group, a C.sub.1 -C.sub.4 alkylsulfonyl group, a C.sub.1 -C.sub.4 alkenylsulfenyl group, a C.sub.1 -C.sub.4 alkenylsulfinyl group, a C.sub.1 -C.sub.4 alkenylsulfonyl group, NO.sub.2, CN, --NU.sup.1 U.sup.2, a phenyl group, a phenoxy group, and a C.sub.2 -C.sub.5 alkoxycarbonyl group, (provided when the number of the substituent, Z, is two or more, said substituents may be the same or different);
m indicates the number of the substituents, and is 0, 1, 2 or 3;
n indicates the number of the substituents, and is 0, 1, 2, 3, or 4;
p indicates the number of the substituents, and is 0, 1 or 2;
q indicates the number of the substituents, and is 0 or 1;
(provided that when m, n and p each are an integer of 2 or more, the substituents may be the same or different).
[4] Ethylene derivatives of the above-mentioned [2], in which E is CN.
[5] Ethylene derivatives of the above-mentioned [5], in which E is CN.
[6] Ethylene derivatives of the above-mentioned [2], in which E is a heterocyclic group optionally substituted by a C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 haloalkyl group--(said heterocyclic group being a 2-oxazolyl, 2-thiazolyl, 2-imidazolyl, 1,2,4-triazol-3-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-thiadiazol-3-yl or 1,3,4-oxadiazol-2-yl group)--or is a halogen atom, a C.sub.2 -C.sub.4 alkynyl group, a phenylethynyl group optionally substituted by Z, a C.sub.1 -C.sub.4 haloalkyl group, CN, NO.sub.2, N.sub.3, CHO, a C.sub.2 -C.sub.5 alkylcarbonyl group, a C.sub.2 -C.sub.5 alkoxycarbonyl group, a C.sub.2 -C.sub.4 alkylaminocarbonyl group, a C.sub.3 -C.sub.9 dialkylaminocarbonyl group, a benzoyl group optionally substituted by Z, an aminothiocarbonyl group, a C.sub.1 -C.sub.4 alkylsulfenyl group, a C.sub.1 -C.sub.4 alkylsulfinyl group, a C.sub.1 -C.sub.4 alkylsulfonyl group, a phenylsulfenyl group optionally substituted by Z a phenylsulfinyl group optionally substituted by Z, a phenylsulfonyl group optionally substituted by Z, --P(.dbd.O)T.sup.2 T.sup.3, or --P(.dbd.S)T.sup.2 T.sup.3.
[7] Ethylene derivatives of the above-mentioned [3], in which E is a heterocyclic group optionally substituted by a C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 haloalkyl group--(said heterocyclic group being a 2-oxazolyl, 2-thiazolyl, 2-imidazolyl, 1,2,4-triazol-3-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-thiadiazol-3-yl or 1,3,4-oxadiazol-2-yl group)--or is a halogen atom, a C.sub.2 -C.sub.4 alkynyl group, a phenylethynyl group optionally substituted by Z, a C.sub.1 -C.sub.4 haloalkyl group, CN, NO.sub.2, N.sub.3, CHO, a C.sub.2 -C.sub.5 alkylcarbonyl group, a C.sub.2 -C.sub.5 alkoxycarbonyl group, a C.sub.2 -C.sub.4 alkylaminocarbonyl group, a C.sub.3 -C.sub.9 dialkylaminocarbonyl group, a benzoyl group optionally substituted by Z, an aminothiocarbonyl group, a C.sub.1 -C.sub.4 alkylsulfenyl group, a C.sub.1 -C.sub.4 alkylsulfinyl group, a C.sub.1 -C.sub.4 alkylsulfonyl group, a phenylsulfenyl group optionally substituted by Z, a phenylsulfinyl group optionally substituted by Z, a phenylsulfonyl group optionally substituted by Z, --P(.dbd.O)T.sup.2 T.sup.3, or --P(=S)T.sup.2 T.sup.3.
(8] Ethylene derivatives of the above-mentioned [4], in which Q is a phenyl group optionally substituted by G, an oxazolyl group optionally substituted by R, a thiazolyl group optionally substituted by R, a pyrazolyl group optionally substituted by R, a 1,2,3-triazolyl group optionally substituted by R, a pyridinyl group optionally substituted by R, or a pyrimidinyl group optionally substituted by R.
[9] Ethylene derivatives of the above-mentioned [8], in which Q is a phenyl group optionally substituted by G.
[10] Ethylene derivatives of the above-mentioned [8], in which Q is an oxazolyl group optionally substituted by R or a 1,2,3-triazolyl group optionally substituted by R.
[11] Ethylene derivatives of the above-mentioned [8], in which Q is a thiazolyl group optionally substituted by R.
[12] Ethylene derivatives of the above-mentioned (8], in which Q is a pyrazolyl group optionally substituted by R.
[13] Ethylene derivatives of the above-mentioned 5], in which Q is a phenyl group optionally substituted by G, or is Q-9, Q-10, Q-11, Q-12, Q-13, Q-14, Q-25, Q-26, Q-27, Q-28, Q-29, Q-30, Q-44, Q-45, Q-46, Q-47, Q-52, Q-53, Q-54, Q-55, Q-56 or Q-57.
[14] Ethylene derivatives of the above-mentioned [7], in which Q is a phenyl group optionally substituted by G, or is Q-9, Q-10, Q-11, Q-12, Q-13, Q-14, Q-25, Q-26, Q-27, Q-28, Q-29, Q-30, Q-44, Q-45, Q-46, Q-47, Q-52, Q-53, Q-54, Q-55, Q-56 or Q-57.
[15] Ethylene derivatives of the above-mentioned [13) , in which Q is Q-10, Q-44, Q-45, Q-46 or Q-47.
[16] Ethylene derivatives of the above-mentioned [13], in which Q is Q-12, Q-13 or Q-14.
[17] Ethylene derivatives of the above-mentioned [13], in which 0 is Q-25, Q-26, Q-27, Q-28, Q-29 or Q-30.
[18] Ethylene derivatives of the above-mentioned [13], in which Q is a phenyl group optionally substituted by G.
[19] Ethylene derivatives of the above-mentioned 2], in which A is a phenyl group optionally substituted by W, a thiazolyl group optionally substituted by Y, a pyrazolyl group optionally substituted by Y, a pyridinyl group optionally substituted by Y, or a pyrimidinyl group optionally substituted by Y.
[20] Ethylene derivatives of the above-mentioned [3], in which;
Q is a phenyl group optionally substituted by G, a naphthyl group, Q-31, Q-32, Q-33, Q-34, Q-35, Q-36, Q-37, Q-44, Q-45, Q-46, Q-49, ##STR4##
A is ##STR5##
Y.sup.2 is a halogen atom, a C.sub.1 -C.sub.4 alkyl group, a C.sub.1 -C.sub.4 haloalkyl group, a C.sub.1 -C.sub.4 alkoxy group, NO.sub.2, CN, or a C.sub.2 -C.sub.5 alkoxycarbonyl group; and
Y.sup.3 is a halogen atom, a C.sub.1 -C.sub.4 alkyl group, a C.sub.1 -C.sub.6 haloalkyl group, a C.sub.2 -C.sub.4 alkoxyalkyl group, or a phenyl group optionally substituted by X.
[21] Ethylene derivatives of the above-mentioned [20], in which E is CN.
[22] Ethylene derivatives of the above-mentioned [20], in which E is a heterocyclic group optionally substituted by a C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 haloalkyl group--(said heterocyclic group being a 2-oxazolyl, 2-thiazolyl, 2-imidazolyl, 1,2,4-triazol-3-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-thiadiazol-3-yl or 1,3,4-oxadiazol-2-yl group)--or is a halogen atom, a C.sub.2 -C.sub.4 alkynyl group, a phenylethynyl group optionally substituted by Z, a C.sub.1 -C.sub.4 haloalkyl group, CN, NO.sub.2, N.sub.3, CHO, a C.sub.2 -C.sub.5 alkylcarbonyl group, a C.sub.2 -C.sub.5 alkoxycarbonyl group, a C.sub.2 -C.sub.4 alkylaminocarbonyl group, a C.sub.3 -C.sub.9 dialkylaminocarbonyl group, a benzoyl group optionally substituted by Z, an aminothiocarbonyl group, a C.sub.1 -C.sub.4 alkylsulfenyl group, a C.sub.1 -C.sub.4 alkylsulfinyl group, a C.sub.1 -C.sub.4 alkylsulfonyl group, a phenylsulfenyl group optionally substituted by Z, a phenylsulfinyl group optionally substituted by Z, a phenylsulfonyl group optionally substituted by Z, --P(.dbd.O)T.sup.2 T .sup.3, or --P(.dbd.S)T.sup.2 T.sup.3.
[23] Ethylene derivatives of the above-mentioned [1], which are selected from the following: ##STR6##
[24] An agricultural chemical comprising, as the active ingredient, one or more ethylene derivatives of the above-mentioned [1] to [23].
[25] An agent for preventing the attachment of aquatic organisms containing, as an active ingredient, one or more ethylene derivatives of the above-mentioned [1] to [23].
MODES OF CARRYING OUT THE INVENTION
The moiety --C(E).dbd.C(OB)-- of the compounds (I) of the present invention includes two isomers of E-form and Z-form, both of which are within the scope of the invention.
It will be understood that the compounds of formula (I) of the present invention where the substituent B is a hydrogen atom exist as tautomers to be represented by the following: ##STR7## Although the compounds (I) will exist essentially as the enol-form (1'), they could be as the tautomer form (2) under some conditions. It should be understood that the present invention includes all these three tautomers and their mixtures.
Now, preferred embodiments of Q, A, B, E, G, R, R.sup.1, Y, Y.sup.1, Y.sup.2, W, X, Z, T.sup.1, T.sup.2, T.sup.3, T.sup.4, T.sup.5, T.sup.6, T.sup.7, T.sup.8, U.sup.1, U.sup.2, m, n, p and q are referred to hereinunder.
The heterocyclic group for Q, A and B indicates the following meanings.
Specifically, thienyl is thiophen-2-yl or thiophen-3-yl; furyl is furan-2-yl or furan-3-yl; pyrrolyl is pyrrol-1-yl, pyrrol-2-yl or pyrrol-3-yl; oxazolyl is oxazol-2-yl, oxazol-3-yl, oxazol-4-yl or oxazol-5-yl; thiazolyl is thiazol-2-yl, thiazol-4-yl or thiazol-5-yl; imidazolyl is imidazol-1-yl, imidazol-2-yl or imidazol-4-yl; isoxazolyl is isoxazol-3-yl, isoxazol-4-yl or isoxazol-5-yl; isothiazolyl is isothiazol-3-yl, isothiazol-4-yl or isothiazol-5-yl; pyrazolyl is pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl or pyrazol-5-yl; 1,3,4-oxadiazolyl is 1,3,4-oxadiazol-2-yl; 1,3,4-thiadiazolyl is 1, 4-thiadiazol-2-yl; 1,2,4-oxadiazolyl is 1,2,4-oxadiazol-3-yl or 1,2,4-oxadiazol-5-yl; 1,2,4-thiadiazolyl is 1,2,4-thiadiazol-3-yl or 1,2,4-thiadiazol-5-yl; 1,2,4-triazolyl is 1,2,4-triazol-1-yl, 1,2,4-triazol-3-yl or 1,2,4-triazol-4-yl; 1,2,3-thiadiazolyl is 1,2,3-thiadiazol-4-yl or 1,2,3-thiadiazol-5-yl; 1,2,3-triazolyl is 1,2,3-triazol-1-yl, 1,2,3-triazol-2-yl or 1,2,3-triazol-4-yl; 1,2,3,4-tetrazolyl is 1,2,3,4-tetrazol-1-yl, 1,2,3,4-tetrazol-2-yl or 1,2,3,4-tetrazol-5-yl; pyridinyl is pyridin-2-yl, pyridin-3-yl or pyridin-4-yl; pyrimidinyl is pyrimidin-2-yl, pyrimidin-4-yl or pyrimidin-5-yl; pyrazinyl is pyrazin-2-yl; pyridazinyl is pyridazin-3-yl or pyridazin-4-yl; 1,3,5-triazinyl is 1,3,5-triazin-2-yl; 1,2,4-triazinyl is 1,2,4-triazin-3-yl, 1,2,4-triazin5-yl or 1,2,4-triazin-6-yl; 1,2,4,5-tetrazinyl is 1,2,4,5-tetrazin-3-yl; pyrazolinyl is 3-pyrazolin-1-yl, 3-pyrazolin-3-yl, 3-pyrazolin-4-yl or 3-pyrazolin-5-yl; imidazolinyl is 1-imidazolin-3-yl, 1-imidazolin-2yl, 1-imidazolin-4-yl or 4-imidazolin-2-yl; oxazolinyl is 2-oxazolin-2-yl, 2-oxazolin-4-yl or 2-oxazolin-5-yl; isoxazolinyl is 2-isoxazolin-3-yl, 2-isoxazolin-4-yl or 2-isoxazolin-5-yl; thiazolinyl is 2-thiazolin-2-yl, 2-thiazolin-4-yl or 3-thiazolin-2-yl; imidazolidinon-yl is imidazolidin-2-on-1-yl; imidazolinon-yl is 2-imidazolinon-1-yl; and 3(2H)-pyridazinon-yl is 3(2H)-pyridazinon-2-yl, 3(2H)-pyridazinon-4-yl, 3(2H)-pyridazinon-5-yl or 3(2H)-pyridazinon-6-yl.
Preferred scope of Q is the following groups.
QI: phenyl, thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,4,5-tetrazinyl.
QII: phenyl, thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridinyl, pyrimidinyl.
QIII: phenyl, thienyl, oxazolyl, thiazolyl, pyrazolyl, pyridinyl, pyrimidinyl, 1,2,3-triazolyl.
QIV: phenyl.
QV: oxazolyl.
QVI: thiazolyl.
QVII: pyrazolyl.
QVIII: pyrimidinyl.
QIX: 1,2,3-triazolyl.
Preferred scope of A is the following groups.
AI: phenyl, thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl.
AII: phenyl, thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,3-thiadiazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl.
AIII: phenyl, thiazolyl, pyrazolyl, pyridinyl, pyrimidinyl.
AIV: thiazolyl, pyrazolyl, pyridinyl.
AV: thiazolyl.
AVI: pyrazolyl.
AVII: pyridinyl
Preferred scope of B is the following groups.
BI: H, C.sub.2 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.4 alkoxyalkyl, CH.sub.3 OC.sub.2 H.sub.4 OCH.sub.2, C.sub.1 -C.sub.4 alkylsulfonyl, phenylsulfonyl optionally substituted by halogen or C.sub.1 -C.sub.4 alkyl, --SO.sub.2 CF.sub.3, C.sub.2 -C.sub.8 dialkylaminosulfonyl, C.sub.3 -C.sub.9 dialkylaminothiocarbonyl, C.sub.3 -C.sub.9 alkoxycarbonylalkyl, --C(.dbd.O)T.sup.1, --P(.dbd.O)T.sup.2 T.sup.3, --P(.dbd.S)T.sup.2 T.sup.3, alkali metal, alkaline earth metal or NHT.sup.4 T.sup.5 T.sup.6.
BII: H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.4 alkoxyalkyl, CH.sub.3 OC.sub.2 H.sub.4 OCH.sub.2, C.sub.1 -C.sub.4 alkylsulfonyl, --SO.sub.2 CF.sub.3, --C(.dbd.O)T.sup.1, alkali metal, alkaline earth metal or NHT.sup.4 T.sup.5 T.sup.6.
BIII: H, C.sub.2 -C.sub.4 alkoxyalkyl, C.sub.1 -C.sub.4 alkylsulfonyl, --SO.sub.2 CF.sub.3, --C(.dbd.O)T.sup.1, alkali metal, alkaline earth metal, NHT.sup.4 T.sup.5 T.sup.6.
BIV: C.sub.2 -C.sub.4 alkoxyalkyl, C.sub.1 -C.sub.4 alkylsulfonyl, --SO.sub.2 CF.sub.3, --C(.dbd.O)T.sup.1, alkali metal, alkaline earth metal or NHT.sup.4 T.sup.5 T.sup.6.
Preferred scope of E is the following grouips.
EI: halogen, C.sub.2 -C.sub.4 alkynyl, phenylethynyl optionally substituted by Z, C.sub.1 -C.sub.4 haloalkyl, CN, NO.sub.2, N.sub.3, CHO, C.sub.2 -C.sub.5 alkylcarbonyl, C.sub.2 -C.sub.5 alkoxycarbonyl, C.sub.2 -C.sub.4 alkylaminocarbonyl, C.sub.3 -C.sub.9 dialkylaminocarbonyl, benzoyl optionally substituted by Z, aminothiocarbonyl, C.sub.1 -C.sub.4 alkylsulfenyl, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 alkylsulfonyl, phenylsulfenyl optionally substituted by Z, phenylsulfinyl optionally substituted by Z, phenylsulfonyl optionally substituted by Z, --P(.dbd.O)T.sup.2 T.sup.3, --P(=S)T.sup.2 T.sup.3.
EII: halogen, C.sub.2 -C.sub.4 alkynyl, phenylethynyl optionally substituted by Z, CN, C.sub.2 -C.sub.5 alkylcarbonyl, C.sub.2 -C.sub.5 alkoxycarbonyl, C.sub.2 -C.sub.4 alkylaminocarbonyl, C.sub.3 -C.sub.9 dialkylaminocarbonyl, benzoyl optionally substituted by Z, aminothiocarbonyl, C.sub.1 -C.sub.4 alkylsulfenyl, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 alkylsulfonyl, phenylsulfenyl optionally substituted by Z, phenylsulfinyl optionally substituted by Z, phenylsulfonyl optionally substituted by Z or --P(.dbd.O)T.sup.2 T.sup.3.
EIII: CN.
Preferred scope of G is the following groups.
GI: substituents freely selected from halogen, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.4 alkenyl, C.sub.2 -C.sub.4 alkynyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.4 haloalkenyl, C.sub.2 -C.sub.4 haloalkynyl, C.sub.3 -C.sub.6 cycloalkyl optionally substituted by C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.2 -C.sub.4 alkenyloxy, C.sub.2 -C.sub.4 alkynyloxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.2 -C.sub.4 haloalkenyloxy, C.sub.3 -C.sub.4 haloalkynyloxy, C.sub.1 -C.sub.4 alkylsulfenyl, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.2 -C.sub.4 alkenylsulfenyl, C.sub.2 -C.sub.4 alkenylsulfinyl, C.sub.2 -C.sub.4 alkenylsulfonyl, C.sub.2 -C.sub.4 alkynylsulfenyl, C.sub.2 -C.sub.4 alkynylsulfinyl, C.sub.2 -C.sub.4 alkynylsulfonyl, C.sub.1 -C.sub.4 haloalkylsulfenyl, C.sub.2 -C.sub.4 haloalkylsulfinyl, C.sub.1 -C.sub.4 haloalkylsulfonyl, C.sub.2 -C.sub.4 haloalkenylsulfenyl, C.sub.2 -C.sub.4 haloalkenylsulfinyl, C.sub.2 -C.sub.4 haloalkenylsulfonyl, C.sub.2 -C.sub.4 haloalkynylsulfenyl, C.sub.2 -C.sub.4 haloalkynylsulfinyl, C.sub.2 -C.sub.4 haloalkynylsulfonyl, NO.sub.2, CN, --NU.sup.1 U.sup.2, methoxy substituted by phenyl optionally substituted by halogen or C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.6 alkoxycarbonyl, C.sub.2 -C.sub.4 alkoxyalkyl, C.sub.2 -C.sub.4 alkylcarbonyl, C.sub.2 -C.sub.4 haloalkylcarbonyl, C.sub.2 -C.sub.4 alkylcarbonyloxy, C.sub.2 -C.sub.6 haloalkylcarbonyloxy, C.sub.3 -C.sub.7 dialkylaminocarbonyloxy, phenyl optionally substituted by Z, phenoxy optionally substituted by Z, benzoyl optionally substituted by Z, pyridyl optionally substituted by Z, and pyridyloxy optionally substituted by Z (provided that when the substituent is two or more, said substituents may be the same or different) and the number of the substituent, G, is 1, 2, 3 or 4, or G is an alkylene group as bonded to the adjacent substituting positions to form a 5-, 6-, 7- or 8-membered ring
GII: substituents freely selected from halogen, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.4 alkenyl, C.sub.2 -C.sub.4 alkynyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.6 cycloalkyl optionally substituted by C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.2 -C.sub.4 alkenyloxy, C.sub.2 -C.sub.4 alkynyloxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.2 -C.sub.4 haloalkenyloxy, C.sub.1 -C.sub.4 alkylsulfenyl, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.2 -C.sub.4 alkenylsulfenyl, C.sub.2 -C.sub.4 alkenylsulfinyl, C.sub.2 -C.sub.4 alkenylsulfonyl, C.sub.2 -C.sub.4 alkynylsulfenyl, C.sub.2 -C.sub.4 alkynylsulfinyl, C.sub.2 -C.sub.4 alkynylsulfonyl, C.sub.1 -C.sub.4 haloalkylsulfenyl, C.sub.1 -C.sub.4 haloalkylsulfinyl, C.sub.1 -C.sub.4 haloalkylsulfonyl, C.sub.2 -C.sub.4 haloalkenylsulfenyl, C.sub.2 -C.sub.4 haloalkenylsulfinyl, C.sub.2 -C.sub.4 haloalkenylsulfonyl, methoxy substituted by phenyl optionally substituted by halogen or C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.6 alkoxycarbonyl, C.sub.2 -C.sub.5 alkylcarbonyloxy, C.sub.2 -C.sub.5 haloalkylcarbonyloxy, phenoxy optionally substituted by Z, and pyridyloxy optionally substituted by Z (provided that the number of the substituent is two or more, said substituebts may be the same or different), and the number of the substituent, G, is 1, 2 or 3.
GIII: substituents freely selected from halogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.3 -C.sub.6 cycloalkyl optionally substituted by C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.2 -C.sub.4 alkenyloxy, C.sub.2 -C.sub.4 alkynyloxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.2 -C.sub.4 haloalkenyloxy, C.sub.1 -C.sub.4 alkylsulfenyl, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.2 -C.sub.4 alkenylsulfenyl, C.sub.2 -C.sub.4 alkenylsulfinyl, C.sub.2 -C.sub.4 alkenylsulfonyl, C.sub.2 -C.sub.4 alkynylsulfenyl, C.sub.2 -C.sub.4 alkynylsulfinyl, C.sub.2 -C.sub.4 alkynylsulfonyl, C.sub.1 -C.sub.4 haloalkylsulfenyl, C.sub.1 -C.sub.4 haloalkylsulfinyl, C.sub.1 -C.sub.4 haloalkylsulfonyl, C.sub.2 -C.sub.4 haloalkenylsulfenyl, C.sub.2 -C.sub.4 haloalkenylsulfinyl, C.sub.2 -C.sub.4 haloalkenylsulfonyl, methoxy substituted by phenyl optionally substituted by halogen or C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.6 alkoxycarbonyl, C.sub.2 -C.sub.5 alkylcarbonyloxy, phenoxy optionally substituted by Z, and pyridyloxy optionally substituted by Z (provided that when the substituent is two or more, said substituents may be the same or different), and the number of the substituent, G, is 1 or 2.
Preferred scope of R is the following group.
RI: substituents freely selected from halogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.3 alkyl substituted by phenyl optionally substituted by halogen or C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.6 cycloalkyl optionally substituted by C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.2 -C.sub.4 alkenyloxy, C.sub.2 -C.sub.4 alkynyloxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.2 -C.sub.4 haloalkenyloxy, C.sub.2 -C.sub.4 haloalkynyloxy, C.sub.1 -C.sub.4 alkylsulfenyl, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.2 -C.sub.4 alkenylsulfenyl, C.sub.2 -C.sub.4 alkenylsulfinyl, C.sub.2 -C.sub.4 alkenylsulfonyl, C.sub.2 -C.sub.4 alkynylsulfenyl, C.sub.2 -C.sub.4 alkynylsulfinyl, C.sub.2 -C.sub.4 alkynylsulfonyl, C.sub.1 -C.sub.4 haloalkylsulfenyl, C.sub.1 -C.sub.4 haloalkylsulfinyl, C.sub.1 -C.sub.4 haloalkylsulfonyl, C.sub.2 -C.sub.4 haloalkenylsulfenyl, C.sub.2 -C.sub.4 haloalkenylsulfinyl, C.sub.2 -C.sub.4 haloalkenylsulfonyl, NO.sub.2, CN, --NU.sup.1 U.sup.2, naphthyl, C.sub.2 -C.sub.4 alkoxycarbonyl, C.sub.2 -C.sub.4 alkoxyalkyl, phenyl optionally substituted by X, pyridyl optionally substituted by X, and thienyl optionally substituted by X (provided that when the substituent is two or more, said substituents may be the same or different), and the number of the substituent, R, is 1, 2 or 3, or R is an alkylene group as bonded to the adjacent substituting positions to form a 5-, 6-, 7- or 8-membered ring.
RII: substituents freely selected from halogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.3 alkyl substituted by phenyl optionally substituted by halogen or C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.3 -C.sub.6 cycloalkyl optionally substituted by C.sub.1 -C.sub.3 alkyl, NO.sub.2, CN, --NU.sup.1 U.sup.2, naphthyl, C.sub.2 -C.sub.4 alkoxycarbonyl, C.sub.1 -C.sub.4 alkoxyalkyl, phenyl optionally substituted by X, and pyridyl optionally substituted by X (provided that when the substituents is two or more, said substituents may be the same or different), and the number of the substituent, R, is 1, 2 or 3.
RIII: substituents freely selected from halogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.3 alkyl substituted by phenyl optionally substituted by halogen or C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.3 -C.sub.6 cycloalkyl optionally substituted by C.sub.1 -C.sub.3 alkyl, NO.sub.2, CN, --NU.sup.1 U.sup.2, naphthyl, C.sub.2 -C.sub.4 alkoxycarbonyl, phenyl optionally substituted by X, and pyridyl optionally substituted by X (provided that when the substituent is two or more, said substituents may be the same or different), and the number of the substituent, R, is 1 or 2.
Depending on the type of the heterocyclic group to be substituted by R, the number of R differs. For the group of 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,3-oxadiazolyl, 1,2,3-thiadiazolyl or 1,2,3,4-tetrazolyl, the number of R is 0 or 1, preferably 1. For the group of thiazolyl, oxazolyl, isoxazolyl, isothiazolyl, 1,3,4-triazolyl, 1,2,4-triazolyl, 1,2,3-triazolyl, 1,3,5-triazinyl, 1,2,4-triazinyl or 1,2,4-triazinyl, the number of R is an integer of from 0 to 2, preferably 1 or 2. For the group of thienyl, furyl, pyrazolyl, imidazolyl, pyrimidinyl, pyrazinyl or pyridazinyl, the number of R is an integer of from 0 to 3, preferably an integer of from 0 to 2, more preferably 1 or 2. For the group of pyrrolyl, pyridinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl or thiazolinyl, the number of R is an integer of from 0 to 4, preferably an integer of from 0 to 3, more preferably 1 or 2.
Preferred scope of Y is the following groups.
YI: substituents freely selected from halogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.2 -C.sub.4 alkenyloxy, C.sub.2 -C.sub.4 alkynyloxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.2 -C.sub.4 haloalkenyloxy, C.sub.2 -C.sub.4 haloalkynyloxy, C.sub.1 -C.sub.4 alkylsulfenyl, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.2 -C.sub.4 alkenylsulfenyl, C.sub.2 -C.sub.4 alkenylsulfinyl, C.sub.2 -C.sub.4 alkenylsulfonyl, C.sub.2 -C.sub.4 alkynylsulfenyl, C.sub.2 -C.sub.4 alkynylsulfinyl, C.sub.2 -C.sub.4 alkynylsulfonyl, C.sub.1 -C.sub.4 haloalkylsulfenyl, C.sub.1 -C.sub.4 haloalkylsulfinyl, C.sub.1 -C.sub.4 haloalkylsulfonyl, C.sub.2 -C.sub.4 haloalkenylsulfenyl, C.sub.2 -C.sub.4 haloalkenylsulfinyl, C.sub.2 -C.sub.4 haloalkenylsulfonyl, C.sub.2 -C.sub.4 haloalkynylsulfenyl, C.sub.2 -C.sub.4 haloalkynylsulfinyl, C.sub.2 -C.sub.4 haloalkynylsulfonyl, NO.sub.2, CN, --NU.sup.1 U.sup.2, C.sub.2 -C.sub.4 alkoxycarbonyl, C.sub.2 -C.sub.4 alkoxyalkyl, C.sub.2 -C.sub.4 alkylcarbonyloxy, C.sub.2 -C.sub.4 haloalkylcarbonyloxy, and phenyl optionally substituted by X (provided that the substituent is two or more, said substituents may be the same or different) and the number of the substituent, Y, is 1, 2 or 3.
YII: substituents freely selected from halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylsulfenyl, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.1 -C.sub.4 haloalkylsulfenyl, C.sub.1 -C.sub.4 haloalkylsulfinyl, C.sub.1 -C.sub.4 haloalkylsulfonyl, NO.sub.2,CN, C.sub.2 -C.sub.4 alkoxycarbonyl, and phenyl optionally substituted by X (provided that when the substituent is two or more, said substituents may be the same or different) and the number of the substituent, Y, is 1, 2 or 3.
Depending on the type of the heterocyclic group to be substituted by Y, the number of Y differs. For the group of 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,3-thiadiazolyl or 1,2,3,4-tetrazolyl, the number of Y is 0 or 1, preferably 1. For the group of thiazolyl, oxazolyl, isoxazolyl, isothiazolyl, 1,3,4-triazolyl, 1,2,4-triazolyl, 1,2,3-triazolyl, 1,3,5-triazinyl, 1,2,4-triazinyl or 1,2,4-triazinyl, the number of Y is an integer of from 0 to 2, preferably 1 or 2. For the group of thienyl, furyl, pyrazolyl, imidazolyl, pyrimidinyl, pyrazinyl or pyridazinyl, the number of Y is an integer of from 0 to 3, preferably an integer of from 0 to 2, more preferably 1 or 2. For the group of pyrrolyl, pyridinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl or thiazolinyl, the number of Y is an integer of from 0 to 4, preferably an integer of from 0 to 3, more preferably 1 or 2.
Preferred scope of W is the following group.
WI: substituents freely selected from halogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 alkylsulfenyl, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.1 -C.sub.4 haloalkylsulfenyl, C.sub.1 -C.sub.4 haloalkylsulfinyl, C.sub.1 -C.sub.4 haloalkylsulfonyl, C.sub.2 -C.sub.4 alkenyloxy, C.sub.2 -C.sub.4 haloalkenyloxy, C.sub.2 -C.sub.4 alkenylsulfenyl, C.sub.2 -C.sub.4 alkenylsulfinyl, C.sub.2 -C.sub.4 alkenylsulfonyl, C.sub.2 -C.sub.4 haloalkenylsulfenyl, C.sub.2 -C.sub.4 haloalkenylsulfinyl, c.sub.2 -C.sub.4 haloalkenylsulfonyl, C.sub.2 -C.sub.4 alkynyloxy, C.sub.2 -C.sub.4 alkynylsulfenyl, C.sub.2 -C.sub.4 alkynylsulfinyl, C.sub.2 -C.sub.4 alkynylsulfonyl, NO.sub.2, CN, C.sub.2 -C.sub.4 alkoxycarbonyl, C.sub.2 -C.sub.4 alkylcarbonyl, C.sub.2 -C.sub.4 haloalkylcarbonyl, C.sub.2 -C.sub.4 alkylcarbonyloxy, and --NU.sup.1 U.sup.2 (provided that when the substituent is two or more, said substituents are the same or different) and the number of the substituent, W, is 1, 2, 3 or 4.
WII: substituents freely selected from halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 alkylsulfenyl, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.1 -C.sub.4 haloalkylsulfenyl, C.sub.1 -C.sub.4 haloalkylsulfinyl, C.sub.1 -C.sub.4 haloalkylsulfonyl, C.sub.2 -C.sub.4 alkenyloxy, C.sub.2 -C.sub.4 haloalkenyloxy, C.sub.2 -C.sub.4 alkenylsulfenyl, C.sub.2 -C.sub.4 alkenylsulfinyl, C.sub.1 -C.sub.4 alkenylsulfonyl, C.sub.2 -C.sub.4 alkynyloxy, C.sub.2 -C.sub.4 alkynylsulfenyl, C.sub.2 -C.sub.4 alkynylsulfinyl, C.sub.2 -C.sub.4 alkynylsulfonyl, NO.sub.2, and CN (provided that the substituent is two or more, said substituents may be the same or different) and the number of the substituent, W, is 1, 2 or 3.
WIII: substituents freely selected from halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 alkylsulfenyl, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.1 -C.sub.4 haloalkylsulfenyl, C.sub.1 -C.sub.4 haloalkylsulfinyl, C.sub.1 -C.sub.4 haloalkylsulfonyl, NO.sub.2, and CN (provided that when the substituent is two or more, the substituents may be the same or different) and the number of the substituent, W, is 1 or 2.
Preferred scope of T.sup.1 is the following groups.
T.sup.1 I: C.sub.1 -C.sub.18 alkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkyl substituted by phenyl optionally substituted by halogen or C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.6 halocycloalkyl, C.sub.3 -C.sub.6 cycloalkyl optionally substituted by C.sub.1 -C.sub.3 alkyl, cycloalkyl substituted by phenyl optionally substituted by halogen or C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkenyl substituted by phenyl optionally substituted by halogen or C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.10 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.2 -C.sub.6 alkenyloxy, C.sub.3 -C.sub.6 cycloalkoxy optionally substituted by C.sub.1 -C.sub.4 alkyl, benzyloxy, C.sub.2 -C.sub.6 alkoxycarbonyl, --NU.sup.1 U.sup.2, phenyl optionally substituted by Z, phenoxy optionally substituted by Z, phenylthio optionally substituted by Z, naphthyl, and heterocyclic group optionally substituted by Z. (said heterocyclic group being selected from thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl and 1,2,4-triazinyl groups).
T.sup.1 II: C.sub.1 -C.sub.1 alkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.4 alkoxyalkyl, C.sub.1 -C.sub.4 alkyl substituted by phenyl optionally substituted by halogen or C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.6 cycloalkyl optionally substituted by C.sub.1 -C.sub.3 alkyl, cycloalkyl substituted by phenyl optionally substituted by halogen or C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkenyl substituted by phenyl optionally substituted by halogen or C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.10 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.2 -C.sub.5 alkenyloxy, C.sub.3 -C.sub.6 cycloalkoxy, benzyloxy, C.sub.2 -C.sub.5 alkoxycarbonyl, phenyl optionally substituted by Z, phenoxy optionally substituted by Z, phenylthio, naphthyl, and heterocyclic group optionally substituted by Z (said heterocyclic group being selected from thienyl, furyl, oxazolyl, thiazolyl, pyrazolyl and pyridinyl groups).
T.sup.1 III: C.sub.1 -C.sub.17 alkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxyalkyl, C.sub.1 -C.sub.4 alkyl substituted by phenyl, C.sub.3 -C.sub.6 cycloalkyl optionally substituted C.sub.1 -C.sub.3 alkyl, cycloalkyl substituted by phenyl, C.sub.2 -C.sub.4 alkenyl substituted by phenyl, C.sub.1 -C.sub.8 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.2 -C.sub.5 alkenyloxy, C.sub.3 -C.sub.6 cycloalkoxy, benzyloxy, C.sub.1 -C.sub.5 alkoxycarbonyl, phenyl optionally substituted by Z, phenoxy optionally substituted by Z, phenylthio, naphthyl, pyrazolyl optionally substituted by Z or pyridinyl optionally substituted by Z.
Preferred scope of T.sup.2 is the following groups.
T.sup.2 I: phenyl, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkylsulfenyl.
Preferred scope of T.sup.4 is the following groups.
T.sup.3 I: phenyl, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.6 alkoxy or C.sub.1 -C.sub.4 alkylsulfenyl.
Preferred scope of T.sup.4 is the following groups.
T.sup.4 I: H, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.6 cycloalkyl or benzyl. Also preferred is such that any two of T.sup.4, T.sup.5 and T.sup.6, together with the nitrogen atom to which they are bonded, forms a 5-, 6- or 7-membered ring optionally having oxygen, nitrogen and/or sulfur atoms.
Preferred scope of T.sup.5 is the following groups.
T.sup.5 I: H, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.6 cycloalkyl or benzyl. Also, preferred is such that any two of T.sup.4, T.sup.5 and T.sup.6, together with the nitrogen atom to which they are bonded, forms a 5-, 6- or 7-membered ring optionally having oxygen, nitrogen and/or sulfur atoms.
Preferred scope of TO is the following groups.
T.sup.6 I: H, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.6 cycloalkyl or benzyl. Also, preferred is such that any two of T.sup.4, T.sup.5 and T.sup.6, together with the nitrogen atom to which they are bonded, forms a 5-, 6- or 7-membered ring optionally having oxygen, nitrogen and/or sulfur atoms.
Preferred scope of X is the following groups.
XI: substituents freely selected from halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 alkylsulfenyl, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.2 -C.sub.5 alkenylsulfenyl, C.sub.2 -C.sub.5 alkenylsulfinyl, C.sub.2 -C.sub.5 alkenylsulfonyl, C.sub.1 -C.sub.4 haloalkylsulfenyl, C.sub.1 -C.sub.4 haloalkylsulfinyl, C.sub.1 -C.sub.4 haloalkylsulfonyl, NO.sub.2, CN, --NU.sup.1 U.sup.2 and C.sub.2 -C.sub.5 alkoxycarbonyl (provided that the substituent is two or more, said substituents may be the same or different) and the substituent, X, is 1, 2 or 3.
XII: substituents freely selected from halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 alkylsulfenyl, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.2 -C.sub.5 alkenylsulfenyl, C.sub.1 -C.sub.4 haloalkylsulfenyl, C.sub.1 -C.sub.4 haloalkylsulfinyl, C.sub.1 -C.sub.4 haloalkylsulfonyl, and NO.sub.2 (provided that when the substituent is two or more, said substituents may be the same or different) and the number of the substituent, X, is 1, 2 or 3.
XIII: substituents freely selected from halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, and C.sub.1 -C.sub.4 alkoxy (provided that when the substituent is two or more, said substituents may be the same or different) and the number of the substituent, X, is 1 or 2.
Depending on the type of the ring to be substituted by X, the number of X differs. For phenyl, the number of X is an integer of from 0 to 5, preferably an integer of from 0 to 3, more preferably an integer of from 0 to 2. For pyridyl, the number of X is an integer of from 0 to 4, preferably 0, 1 or 2, more preferably 0 or 1. For thienyl, the number of X is an integer of from 0 to 3, preferably 0 or 1.
Preferred scope of Z is the following groups.
ZI: substituents freely selected from halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 alkylsulfenyl, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.2 -C.sub.5 alkenylsulfenyl, C.sub.2 -C.sub.6 alkenylsulfinyl, C.sub.2 -C, alkenylsulfonyl, C.sub.1 -C.sub.4 haloalkylsulfenyl, C.sub.1 -C.sub.4 haloalkylsulfinyl, C.sub.1 -C.sub.4 haloalkylsulfonyl, NO.sub.2, CN, --NU.sup.1 U.sup.2 and C.sub.2 -C.sub.5 alkoxycarbonyl (provided that when the substituent is two or more, said substituents may be the same or different) and the number of the substituent, Z, is 1, 2, 3 or 4.
ZII: substituents freely selected from halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 alkylsulfenyl, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.2 -C.sub.5 alkenylsulfenyl, C.sub.2 -C.sub.5 alkenylsulfinyl, C.sub.2 -C.sub.5 alkenylsulfonyl, C.sub.1 -C.sub.4 haloalkylsulfenyl, C.sub.1 -C.sub.4 haloalkylsulfinyl and C.sub.1 -C.sub.4 haloalkylsulfonyl (provided that when the substituent is two or more, said substituents may be the same or different) and the substituent, Z, is 1, 2, 3 or 4.
Depending on the type of the ring to be substituted by Z, the number of Z differs. For phenyl, the number of Z is an integer of from 0 to 5, preferably an integer of from 0 to 4, more preferably 0, 1, 2 or 3, even more preferably 0, 1 or 2. For naphthyl, the number of Z is an integer of from 0 to 7, preferably 0. Where the ring to be substituted by Z is a heterocyclic group, the number of the substituents of Z also differs depending on the type of the heterocyclic group. For the group of 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,3-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,3,4-tetrazolyl or 1,2,3,5-tetrazolyl, the number of Z is 0 or 1. For the group of thiazolyl, oxazolyl, isoxazolyl, isothiazolyl, 1,3,4-triazolyl, 1,2,4-triazolyl, 1,2,3-triazolyl, 1,3,5-triazinyl, 1,2,4-triazinyl or 1,2,4-triazinyl, the number of Z is an integer of from 0 to 2, preferably 1 or 2. For the group of thienyl, furyl, pyrazolyl, imidazolyl, pyrimidinyl, pyrazinyl or pyridazinyl, the number of Z is an integer of from 0 to 3, preferably an integer of from 0 to 2, more preferably 1 or 2. For the group of pyrrolyl, pyridinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl or thiazolinyl, the number of Z is an integer of from 0 to 4, preferably an integer of from 0 to 2, more preferably 1 or 2.
Preferred scope of T.sup.7 is the following groups.
T.sup.7 I: H, phenyl, benzyl or C.sub.1 -C.sub.4 alkyl. Also preferred is such that T.sup.7 and T.sup.8, together with the carbon atom to which they are bonded, form a 5-membered or 6-membered ring.
Preferred scope of T.sup.8 is the following groups.
T.sup.8 I: phenyl, benzyl or C.sub.1 -C.sub.4 alkyl. Also preferred is such that T.sup.7 and T.sup.8, together with the carbon atom to which they are bonded, form a 5-membered or 6-membered ring.
Preferred scope of U.sup.1 is the following groups.
U.sup.1 I: H, C.sub.1 -C.sub.4 alkyl or C.sub.2 -C.sub.5 alkylcarbonyl. Also preferred is such that U.sup.1 and U.sup.2, together with nitrogen atom to which they are bonded, form a 5-, 6- or 7-membered ring.
Preferred scope of U.sup.2 is the following groups.
U.sup.2 I: H, C.sub.1 -C.sub.4 alkyl or C.sub.2 -C.sub.5 alkylcarbonyl. Also preferred is such that U.sup.1 and U.sup.2, together with the carbon atom to which they are bonded, form a 5-, 6- or 7-membered ring.
Preferably, m is 1, 2, or 3, more preferably 1 or 2.
Preferably n is 0, 1, 2 or 3, more preferably 1 or 2.
Preferably, p is 1 or 2.
The above-mentioned preferred groups in the scopes of the preferred substituents can be optionally combined and show the scopes of the preferred compounds of the present invention. Hereinunder mentioned are especially preferred scopes.
Compounds of the invention comprising preferred substituents of QI, AI, BI, El, GI, RI, YI, WI, T.sup.1 I, T.sup.2 I T.sup.3 I, T.sup.4 I, T.sup.5 I, T.sup.6 I, XI, ZI, T.sup.7 I, T.sup.8 I, U.sup.1 I and U.sup.2 I.
Compounds of the invention comprising preferred substituents of QI, AI, BI, EIII, GI, RI, YI, WI, T.sup.1 I, T .sup.2 I T.sup.3 I, T.sup.4 I, T.sup.5 I, T.sup.6 I, XI, ZI, T.sup.7 I, T.sup.8 I, U.sup.1 I and U.sup.2 I.
Compounds of the invention comprising preferred substituents of QII, AII, BI, EII, GI, RI, YI, WI, T.sup.1 I, T.sup.2 I, T.sup.3 I, T.sup.4 I, T.sup.5 I, T.sup.6 I, XI, ZI, T.sup.7 I, T.sup.8 I, U.sup.1 I and U.sup.2 I.
Compounds of the invention comprising preferred substituents of QII, AII, BI, EIII, GI, RI, YI, WI, T.sup.1 I, T.sup.2 I, T.sup.3 I, T.sup.4 I, T.sup.5 I, T.sup.6 I, XI, ZI, T.sup.7 I, T.sup.8 I, U.sup.1 I and U.sup.2 I.
Compounds of the invention comprising preferred substituents of QIII, AIII, BI, EIII, GI, RI, YI, WI, T.sup.1 I, T.sup.2 I, T.sup.3 I, T.sup.4 I, T.sup.5 I, T.sup.6 I, XI, ZI, T.sup.7 I, T.sup.8 I, U.sup.1 I and U.sup.2 I.
Compounds of the invention comprising preferred substituents of QIII, AIII, BII, EIII, GII, RII, YII, WII, T.sup.1 II, T.sup.2 I, T.sup.3 I, T.sup.4 I, T.sup.5 I, T.sup.6 I, XII, ZII, T.sup.7 I, T.sup.8 I, U.sup.1 I and U.sup.2 I.
Compounds of the invention comprising preferred substituents of QIII, AIII, BII, EIII, GIII, RIII, YII, WII, T.sup.1 III, T.sup.2 I, T.sup.3 I, T.sup.4 I, T.sup.5 I, T.sup.6 I, XIII, ZII, T.sup.7 I, T.sup.8 I, U.sup.1 I and U.sup.1 I.
Compounds of the invention comprising preferred substituents of QIII, AIV, BIII, EIII, GIII, RIII, YII, WII, T.sup.1 III, T.sup.2 I, T.sup.3 I, T.sup.4 I, T.sup.5 I, T.sup.6 I, XIII, ZII, T.sup.7 I, T.sup.8 I, U.sup.1 I and U.sup.2 I.
Compounds of the invention comprising preferred substituents of QIV, AIV, BIII, EIII, GIII, RIII, YII, WII, T.sup.1 III, T.sup.2 I, T.sup.3 I, T.sup.4 I, T.sup.5 I, T.sup.6 I, XIII, ZII, T.sup.7 I, T.sup.8 I, U.sup.1 I and U.sup.2 I.
Compounds of the invention comprising preferred substituents of QV, AIII, BIII, EIII, GIII, RIII, YII, WII, T.sup.1 III, T.sup.2 I, T.sup.3 I, T.sup.4 I, T.sup.5 I, T.sup.6 I, XIII, ZII, T.sup.7 I, T.sup.8 I, U.sup.1 I and U.sup.2 I .
Compounds of the invention comprising preferred substituents of QVI, AIII, BIII, EIII, GIII, RIII, YII, WII, T.sup.1 III, T.sup.2 I, T.sup.3 I, T.sup.4 I, T.sup.5 I, T.sup.6 I, XIII, ZII, T.sup.7 I, T.sup.8 I, U.sup.1 I and U.sup.2 I.
Compounds of the invention comprising preferred substituents of QVI, AIV, BIII, EIII, GIII, RIII, YII, WII, T.sup.1 III, T.sup.2 I, T.sup.3 I, T.sup.4 I, T.sup.5 I, T.sup.6 I, XIII, ZII, T.sup.7 I, T.sup.8 I, U.sup.1 I and U.sup.2 I.
Compounds of the invention comprising preferred substituents of QVII, AIII, BIII, EIII, GIII, RIII, YII, WII, T.sup.1 III, T.sup.2 I, T.sup.3 I, T.sup.4 I, T.sup.5 I, T.sup.6 I, XIII, ZII, T.sup.7 I, T.sup.8 I, U.sup.1 I and U.sup.2 I.
Compounds of the invention comprising preferred substituents of QVIII, AIII, Bill, EIII, GIII, RIII, YII, WII, T.sup.1 III, T.sup.2 I, T.sup.3 I, T.sup.4 I, T.sup.5 I , T.sup.6 I, XIII, ZII, T.sup.7 I, T.sup.8 I, U.sup.1 I U.sup.2.
Compounds of the invention comprising preferred substituents of QIX, AIII, Bill, EIII, GIII, RIII, YII, WII, T.sup.1 III, T.sup.2 I, T.sup.3 I, T.sup.4 I, T.sup.5 I, T.sup.6 I, XIII, ZII, T.sup.7 I, T.sup.8 I, U.sup.1 I and U.sup.2 I.
Compounds of the invention comprising preferred substituents of QIII, AV, BIII, EIII, GIII, RIII, YII, WII, T.sup.1 III, T.sup.2 I, T.sup.3 I, T.sup.4 I, T.sup.5 I, T.sup.6 I, XIII, ZII, T.sup.7 I, T.sup.8 I, U.sup.1 I and U.sup.2 I.
Compounds of the invention comprising preferred substituents of QIII, AVI, BIII, EIII, GIII, RIII, YII, WII, T.sup.1 III, T.sup.2 I, T.sup.3 I, T.sup.4 I, T.sup.5 I, T.sup.6 I, XIII, ZII, T.sup.7 I, T.sup.8 I, U.sup.1 I and U.sup.2 I.
Compounds of the invention comprising preferred substituents of QIII, AVII, BIII, EIII, GIII, RIII, YII, WII, T.sup.1 III, T.sup.2 I, T.sup.3 I, T.sup.4 I, T.sup.5 I, T.sup.6 I, XIII, ZII, T.sup.7 I, T.sup.8 I, U.sup.1 I and U.sup.2 I.
Now, specific examples of Q, A, B, E, G, R, R.sup.1, Y, Y.sup.1, Y.sup.2, W, X, Z, T.sup.1, T.sup.2, T.sup.3, T.sup.4, T.sup.5, T.sup.6, T.sup.7, T.sup.8, U.sup.1 and U.sup.2 are mentioned below.
The halogen atom for E, G, R, R.sup.1, W, X, Y, Y.sup.1, Y.sup.2, Y.sup.3 and Z includes a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Preferred are a fluorine atom, a chlorine atom and a bromine atom.
The alkyl group for B, G, R, R.sup.1, T.sup.1, T.sup.2, T.sup.3, T.sup.4, T.sup.5, T.sup.6, T.sup.7, T.sup.8, U.sup.1, U.sup.2, W, X, Y, Y.sup.1, Y.sup.2, Y.sup.3 and Z may be a straight chain or branched alkyl group having indicated carbon atoms, which includes, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, pentyl-1, pentyl-2, pentyl-3, 2-methylbutyl-1, 2-methylbutyl-2, 2-methylbutyl-3, 3-methylbutyl-1, 2,2-dimethylpropyl-1, hexyl-1, hexyl-2, hexyl-3, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, n-heptyl, n-octyl, n-nonyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl and n-eicosyl groups.
The alkenyl group for G, R, R.sup.1, T.sup.1, T.sup.4, T.sup.5, T.sup.6, Y.sup.1 and W may be a straight chain or branched alkenyl group having indicated carbon atoms, which includes, for example, ethenyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl and 1-ethyl-1-methyl-2-propenyl groups.
The alkynyl group for E, G, R, R.sup.1, Y.sup.1 and W may be a straight chain or branched alkynyl group having indicated carbon atoms, which includes, for example, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, hexynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-4-pentynyl, 4-methyl-2-pentynyl, 1,a-dimethyl-2-butynyl, 1 l-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 1 -ethyl-2-butynyl, 1-ethyl-3-butynyl and 2-ethyl-3-butynyl groups.
The haloalkyl group for B, E, G, R, R.sup.1, T.sup.1, W, X, Y, Y.sup.1, Y.sup.2, Y.sup.3 and Z may be a straight chain or branched haloalkyl group having indicated carbon atoms, which includes, for example, fluoromethyl, chloromethyl, bromomethyl, fluoroethyl, chloroethyl, bromoethyl, fluoro-n-propyl, chloro-n-propyl, difluoromethyl, chlorodifluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, difluoroethyl, trifluoroethyl, trichloroethyl, chlorodifluoromethyl, bromodifluoromethyl, trifluorochloroethyl, hexafluoro-n-propyl, chlorobutyl, fluorobutyl, chloro-n-pentyl, fluoro-n-pentyl, chloro-n-hexyl and fluoro-n-hexyl groups.
The C.sub.3 -C.sub.6 cycloalkyl group optionally substituted by a C.sub.1 -C.sub.3 alkyl group for G, R, T.sup.1, T.sup.4, T.sup.5 and T.sup.6 includes, for example, cyclopropyl, 1-methylcyclopropyl, 2,2,3,3-tetramethylcyclopropyl, cyclobutyl, 1-ethylcyclobutyl, 1-n-butylcyclobutyl, cyclopentyl, 1-methylcyclopentyl, cyclohexyl, 1-methylcyclohexyl and 4-methylcyclohexyl groups.
The C.sub.1 -C.sub.4 alkyl group substituted by a phenyl group optionally substituted by a halogen atom or a C.sub.1 -C.sub.4 alkyl group for B, G, R and T.sup.1 includes, for example, benzyl, 2-chlorobenzyl, 3-bromobenzyl, 4-chlorobenzyl, 4-methylbenzyl, 4-tert-butylbenzyl, 1-phenylethyl, 1-(3-chlorophenyl)ethyl, 2-phenylethyl, 1-methyl-l-phenylethyl, 1-(4-chlorophenyl)-1-methylethyl, 1-(3-chlorophenyl)-1-methylethyl, 1-phenylpropyl, 2-phenylpropyl, 3-phenylpropyl, 1-phenylpropyl, 2-phenylbutyl, 3-phenylbutyl, 4-phenylbutyl, 1-methyl-1-phenylpropyl, 1-methyl-2-phenylpropyl, 1-methyl-3-phenylpropyl, 2-methyl-2-phenylpropyl, 2-(4-chlorophenyl)-2-methyl-propyl and 2-methyl-2-(3-methylphenyl)propyl groups.
For T.sup.1, the C.sub.3 -C.sub.6 cycloalkyl group substituted by a phenyl group optionally substituted by a halogen atom or a C.sub.1 -C.sub.4 alkyl group includes, for example, 1-phenylcyclopropyl, 1-(3-chlorophenyl)cyclopropyl, 1-(4-chlorophenyl)cyclopropyl, 1-(4-bromophenyl)cyclopropyl, 1-(4-fluorophenyl)cyclopropyl, 1-(4-ethylphenyl)cyclopropyl, 1-(4-propylphenyl)cyclopropyl, 2-phenylcyclopropyl, 1-phenylcyclobutyl, 2-phenylcyclobutyl, 1-phenylcyclopentyl, 1-(4-chlorophenyl)cyclopentyl, 2-phenylcyclopentyl, 3-phenylcyclopentyl, 1-phenylcyclohexyl, 1-(3-fluorophenyl)cyclohexyl, 1-(4-chlorophenyl)cyclohexyl, 1-(4-tert-butylphenyl)cyclohexyl, 2-phenylcyclohexyl, 3-phenylcyclohexyl and 4-phenylcyclohexyl groups.
For T.sup.1, the cyclopropyl group substituted by both a phenyl group optionally substituted by a halogen atom or a C.sub.1 -C.sub.4 alkyl group and a C.sub.1 -C.sub.4 alkyl group includes, for example, 2,2-dimethyl-1-phenylcyclopropyl, 1-(4-chlorophenyl)-2,2-dimethylcyclopropyl, 2,2-dimethyl-3-phenylcyclopropyl, 3-(3-chlorophenyl)-2,2-dimethylcyclopropyl, (4-chlorophenyl)-2,2-dimethyl-3-phenylcyclopropyl, (4-bromophenyl)-2,2-dimethyl-3-phenylcyclopropyl, 2,2-dimethyl-3-(4-methylphenyl)cyclopropyl and (4-tert-butylphenyl)-2,2-dimethyl-3-phenylcyclopropyl groups.
For T.sup.1, the C.sub.3 -C.sub.4 cycloalkyl group substituted by both a phenyl group optionally substituted by a halogen atom or a C.sub.1 -C.sub.4 alkoxy group and a halogen atom includes, for example, 2,2-dichloro-1-phenylcyclopropyl, 2,2-dichloro-1-(3-chlorophenyl)cyclopropyl, 2,2-dichloro-1-(4-methoxyphenyl)cyclopropyl, 2,2-dichloro-1-(4-ethoxyphenyl)cyclopropyl, 2,2-dichloro-(4-i-propyloxyphenyl)cyclopropyl, 2,2-dichloro-1-(4-t-butylphenyl)cyclopropyl, 2,2-dichloro-1-(4-methoxyphenyl)-3-phenylcyclopropyl and 1-(4-ethoxyphenyl)-2,2,3,3-tetrafluorobutyl groups.
For T.sup.1, the cyclopropyl group substituted by both a C.sub.2 -C.sub.4 alkenyl group optionally substituted by a halogen atom, and a C.sub.1 -C.sub.4 alkyl group includes, for example, 2,2-dimethyl-3-(2,2-dimethylethenyl)cyclopropyl, 3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropyl, 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropyl and 3-(2,2-chlorotrifluoroethenyl)-2,2-dimethylcyclopropyl groups.
For T.sup.1, the C.sub.3 -C.sub.6 cycloalkoxy group optionally substituted by a C.sub.1 -C.sub.3 alkyl group includes, for example, cyclopropoxy, cyclobutoxy, cyclopentoxy, cyclohexyloxy and 1-methylcyclopropoxy groups.
For T.sup.1, the C.sub.2 -C.sub.4 alkenyl group substituted by a phenyl group optionally substituted by a halogen atom or a C.sub.1 -C.sub.4 alkyl group includes, for example, 1-phenylethenyl, 2-phenylethenyl, 2-(2-chlorophenyl)ethenyl, 2-(3-chlorophenyl)ethenyl, 2-(4-chlorophenyl)ethenyl, 2-(4-methylphenyl)ethenyl, 2-(2,6-difluorophenyl)ethenyl, 2-(2,5-dimethylphenyl)ethenyl, 1-methyl-2-phenylethenyl, 2-phenyl-1-propenyl, 2-(4-bromophenyl)-1-propenyl and 2-(2,4,6-trimethylphenyl)-1-propenyl groups.
The alkoxy group for G, R, T.sup.1, T.sup.2, T.sup.3, R.sup.1, W, X, Y, Y.sup.1, Y.sup.2 and Z may be a straight chain or branched alkoxy group having indicated carbon atoms, which includes, for example, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentyloxy, 1-methylbutyloxy, 2-methylbutyloxy, 3-methylbutyloxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropyloxy, n-hexyloxy, 1-methylpentyloxy, 2-methylpentyloxy, 3-methylpentyloxy, 4-methylpentyloxy, 1,1-dimethylbutyloxy, 1,2-dimethylbutyloxy, 1,3-dimethylbutyloxy, 2,2-dimethylbutyloxy, 2,3-dimethylbutyloxy, 3,3-dimethylbutyloxy, 1-ethylbutyloxy, 2-ethylbutyloxy, 1,1,2-trimethylpropyloxy, 1,2,2-trimethylpropyloxy, 1-ethyl-1-methylpropyloxy, 1-ethyl-2-methylpropyloxy, n-heptyloxy, n-octyloxy, n-nonyloxy and n-decyloxy groups.
The C.sub.3 -C.sub.6 halocycloalkyl group for G, R and T.sup.1 includes, for example, fluorocyclopropyl, difluorocyclopropyl, chlorocyclopropyl, dichlorocyclopropyl, 1-methyl-2,2-dichlorocyclopropyl, chlorocyclobutyl, dichlorocyclobutyl, chlorocyclopentyl, dichlorocyclopentyl, chlorocyclohexyl, dichlorocyclohexyl and tetrafluorocyclobutyl groups.
The group --NU.sup.1 U.sup.2 for G, R, R.sup.1, T.sup.1, W, X, Y, Y.sup.1 and Z includes, for example, methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, isobutylamino, sec-butylamino, tert-butylamino, n-pentylamino, 1-methylbutylamino, 2-methylbutylamino, 3-methylbutylamino, 1,1-dimethylpropylamino, 1,2-dimethylpropylamino, 2,2-dimethylpropylamino, 1-ethylpropylamino, n-hexylamino, 1-methylpentylamino, 2-methylpentylamino, 3-methylpentylamino, 4-methylpentylamino, 1,1-dimethylbutylamino, 1,2-dimethylbutylamino, -1,3-dimethylbutylamino, 2,2-dimethylbutylamino, 2,3-dimethylbutylamino, 3,3-dimethylbutylamino, 1-ethylbutylamino, 2-ethylbutylamino, 1,1,2-trimethylpropylamino, 1,2,2-trimethylpropylamino, 1-ethyl-1-methylpropylamino, 1-ethyl-2-methylpropylamino, dimethylamino, diethylamino, di-n-propylamino, diisopropylamino, di-n-butylamino, di-sec-butylamino, diisobutylamino, di-n-pentylamino, di-n-hexylamino, methylethylamino, methylpropylamino, methylisopropylamino, methylbutylamino, methyl-sec-butylamino, methyl-isobutylamino, methyl-tert-butylamino, methylpentylamino, methylhexylamino, ethylpropylamino, ethylisopropylamino, ethylbutylamino, ethyl-sec-butylamino, ethyl-isobutylamino, ethylpentylamino, ethylhexylamino, phenylamino, benzylamino, N-methylacetamido, N-ethylacetamido, N-phenylacetamido and N-acetylacetamido groups, to which is applied the indicated scope of the carbon atoms constituting it.
The C.sub.2 -C.sub.5 alkoxycarbonyl group for E, G, R, R.sup.1, T.sup.1, W, X, Y, Y.sup.1, Y.sup.2 and Z includes, for example, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, iso-propoxycarbonyl, n-butoxycarbonyl, sec-butoxycarbonyl, iso-butoxycarbonyl and tert-butoxycarbonyl groups.
The C.sub.1 -C.sub.4 haloalkoxy group for G, R, T.sup.1, W, X, Y and Z may be a straight chain or branched C.sub.1 -C.sub.4 haloalkoxy group, including, for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, dichlorofluoromethoxy, chloromethoxy, dichloromethoxy, trichloromethoxy, bromomethoxy, fluoroethoxy, chloroethoxy, bromoethoxy, difluoroethoxy, trifluoroethoxy, tetrafluoroethoxy, pentafluoroethoxy, trichloroethoxy, trifluorochloroethoxy, fluoropropoxy, chloropropoxy, bromopropoxy, fluorobutoxy, chlorobutoxy, fluoro-iso-propoxy and chloro-iso-propoxy groups.
The C.sub.1 -C.sub.4 alkylsulfenyl group for E, G, R, T.sup.2, T.sup.3, W, X, Y and Z includes, for example, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, iso-butylthio, sec-butylthio and tert-butylthio groups.
The C.sub.1 -C.sub.4 alkylsulfinyl group for E, G, R, X, W, Y and Z includes, for example, methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, iso-propylsulfinyl, n-butylsulfinyl, iso-butylsulfinyl, sec-butylsulfinyl and tert-butylsulfinyl groups.
The C.sub.1 -C.sub.4 alkylsulfonyl group for B, E, G, R, W, X, Y and Z includes, for example, methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, iso-propylsulfonyl, n-butylsulfonyl, iso-butylsulfonyl, sec-butylsulfonyl and tert-butylsulfonyl groups.
The C.sub.2 -C.sub.4 alkoxyalkyl group for B, G, R, R.sup.1, T.sup.1, Y, Y.sup.1 and Y.sup.2 includes, for example, C.sub.1 -C.sub.3 alkoxy-methyl, C.sub.1 -C.sub.2 alkoxy-ethyl, methoxyethoxymethyl and methoxypropyl groups.
The C.sub.2 -C.sub.4 alkylcarbonyl group for E, G, R, R.sup.1, U.sup.1, U.sup.2, Y.sup.1, Y.sup.2 and W includes, for example, acetyl, propionyl, butanoyl and iso-butanoyl groups.
The C.sub.2 -C.sub.6 haloalkylcarbonyl group for G and W includes, for example, chloroacetyl, trifluoroacetyl, 3,3,3-trifluoropropionyl and pentafluoropropionyl groups.
The C.sub.2 -C.sub.5 haloalkylcarbonyloxy group for G, R and Y includes, for example, chloroacetyloxy, trifluoroacetyloxy, 3,3,3-trifluoropropionyloxy and pentafluoropropionyloxy groups.
The C.sub.3 -C.sub.7 dialkylaminocarbonyloxy group for G and Y includes, for example, dimethylaminocarbonyloxy, diethylaminocarbonyloxy and di-i-propylaminocarbonyloxy groups.
The naphthyl group for R, Y, Z and T.sup.1 includes, for example, l-naphthyl and 2-naphthyl groups.
The pyridyl group optionally substituted by Z for G and T.sup.1 includes, for example, 2-pyridyl, 3-pyridyl and 4-pyridyl groups all optionally substituted by Z. Preferred are 2-pyridyl and 3-pyridyl groups both optionally substituted by Z; and more preferred is a 2-pyridyl group optionally substituted by Z.
The pyridyloxy group optionally substituted by Z for G and T.sup.1 includes, for example, 2-pyridyloxy, 3-pyridyloxy and 4-pyridyloxy groups all optionally substituted by Z.
The pyridyl group optionally substituted by X for R and R.sup.1 includes, for example, 2-pyridyl, 3-pyridyl and 4-pyridyl groups all optionally substituted by X. Preferred are 2-pyridyl and 3-pyridyl groups both optionally substituted by X; and more preferred is a 2-pyridyl group optionally substituted by X.
The pyridyloxy group optionally substituted by X for R and R.sup.1 includes, for example, 2-pyridyloxy, 3-pyridyloxy and 4-pyridyloxy groups all optionally substituted by X.
The thienyl group-optionally substituted by X for R and R.sup.1 includes, for example, 2-thienyl and 3-thienyl groups both optionally substituted by X.
The thienyl group optionally substituted by Z for G and Y.sup.1 includes, for example, 2-thienyl and 3-thienyl groups both optionally substituted by Z.
The group --N.dbd.CT.sup.7 T.sup.8 for G, R, R.sup.1, Y and Y.sup.1 indicates an alkylidenamino group, a benzylidenamino group, an arylidenamino group or a cycloalkylidenamino group, including, for example, methylidenamino, ethylidenamino, propylidenamino, isopropylidenamino, 4-methyl-2-pentylidenamino, cyclopentylidenamino and cyclohexylidenamino groups.
The C.sub.2 -C.sub.4 alkylaminocarbonyl group for E includes, for example, methylaminocarbonyl, ethylaminocarbonyl and n-propylaminocarbonyl groups.
The C.sub.3 -C.sub.9 dialkylaminocarbonyl group for E includes, for example, dimethylaminocarbonyl, diethylaminocarbonyl, di-n-propylaminocarbonyl, di-isopropylaminocarbonyl and di-n-butylaminocarbonyl groups.
The C.sub.1 -C.sub.4 alkylaminosulfonyl group for B includes, for example, methylaminosulfonyl, ethylaminosulfonyl, n-propylaminosulfonyl, isopropylaminosulfonyl and n-butylaminosulfonyl groups.
The C.sub.2 -C.sub.8 dialkylaminosulfonyl group for B includes, for example, dimethylaminosulfonyl, diethylaminosulfonyl, di-n-propylaminosulfonyl, di-isopropylaminosulfonyl and di-n-butylaminosulfonyl groups.
The C.sub.2 -C.sub.5 alkylaminothiocarbonyl group for B includes, for example, methylaminothiocarbonyl, ethylaminothiocarbonyl, n-propylaminothiocarbonyl, isopropylaminothiocarbonyl and n-butylaminothiocarbonyl groups.
The C.sub.3 -C.sub.9 dialkylaminothiocarbonyl group for B includes, for example, dimethylaminothiocarbonyl, diethylaminothiocarbonyl, di-n-propylaminothiocarbonyl, di-isopropylaminothiocarbonyl and di-n-butylaminothiocarbonyl groups.
The C.sub.1 -C.sub.4 alkyl group substituted by a benzoyl group optionally substituted by a halogen atom or a C.sub.1 -C.sub.4 alkyl group for B includes, for example, phenacyl, 2-fluorophenacyl, 3-chlorophenacyl, 4-bromophenacyl, 2-methylphenacyl, 3-ethylphenacyl, 4-i-propylphenacyl and 4-t-butylphenacyl groups.
The phenylsulfonyl group optionally substituted by a halogen atom or a C.sub.1 -C.sub.4 alkyl group for B includes, for example, 2-fluorophenylsulfonyl, 4-fluorophenylsulfonyl, 2-chlorophenylsulfonyl, 4-chlorophenylsulfonyl, 4-bromophenylsulfonyl, 2,5-dichlorophenylsulfonyl, pentafluorophenylsulfonyl, 4-methylphenylsulfonyl, 2-methylphenylsulfonyl, 4-t-butylphenylsulfonyl, 2,5-dimethylphenylsulfonyl, 2,4-dimethylphenylsulfonyl, 2,4,6-trimethylphenylsulfonyl and 2,4,6-tri-i-propylphenylsulfonyl groups.
The C.sub.2 -C.sub.5 cyanoalkyl group for G and B includes, for example, cyanomethyl, 2-cyanoethyl, 3-cyanopropyl and 1-cyano-1-methylethyl groups.
The C.sub.3 -C.sub.9 alkoxycarbonylalkyl group for B may be a straight chain or branched one, including, for example, methoxycarbonylmethyl, ethoxycarbonylmethyl, n-propoxycarbonylmethyl, i-propoxycarbonylmethyl, n-butoxycarbonylmethyl, i-butoxycarbonylmethyl, t-butoxycarbonylmethyl, n-hexyloxycarbonylmethyl, n-heptyloxycarbonylmethyl, 1-methoxycarbonylethyl, 1-ethoxycarbonylethyl, 1-n-butoxyethyl, 2-methoxycarbonylethyl, 2-ethoxycarbonylethyl, 1-methoxycarbonylpropyl, 3-ethoxycarbonyipropyl, 4-methoxycarbonylbutyl, 6-ethoxycarbonylhexyl, 1-methoxycarbonyl-1-methylethyl, 1-iso-propoxycarbonyl-1-methylethyl and 1-ethoxycarbonyl-2-methylpropyl groups.
The alkali metal for B includes, for example, lithium sodium and potassium.
The alkaline earth metal for B includes, for example, magnesium, calcium, strontium and barium. Preferred are magnesium, calcium and barium.
The ammonium group of NHT.sup.4 T.sup.5 T.sup.6 for B includes, for example, ammonium, monomethylammonium, dimethylammonium, trimethylammonium, diethylammonium, triethylammonium, di-isopropylammonium, di-isopropylethylammonium, hexylmethylammonium, cyclopropylmethylammonium, cyclohexylmethylammonium, allylmethylammonium, benzylmethylammonium and 4-methylcyclohexylethylammonium groups. Any two of T.sup.4, T.sup.5 and T.sup.6 may form, along with the nitrogen atom to which they are bonded, a heterocyclic, 5-, 6-, 7- or 8-membered ammonium group optionally having oxygen, nitrogen and/or sulfur atoms.
The methoxy group substituted by a phenyl group optionally substituted by a halogen atom or a C.sub.1 -C.sub.4 alkyl group for G includes, for example, benzyloxy, 2-chlorobenzyloxy, 3-chlorobenzyloxy, 4-chlorobenzyloxy, 3-methylbenzyloxy, 4-t-butylbenzyloxy, 2,6-difluorobenzyloxy and 2-fluoro-4-chlorobenzyloxy groups.
The heterocyclic, 5-, 6-, 7- or 8-membered ammonium group optionally having oxygen, nitrogen and/or sulfur atoms, which is formed by two of T.sup.4, T.sup.5 and T.sup.6 along with the nitrogen atom to which they are bonded, includes, for example, pyrrolidine, pyrazolidine, imidazolidine, oxazolidine, isoxazolidine, thiazolidine, piperidine, piperazine, morpholine, thiamorpholine, hexamethylenimine and heptamethylenimine groups. The haloalkylsulfenyl group for G, R, W, X, Y and Z may be a straight chain or branched C.sub.1 -C.sub.4 haloalkylthio group, including, for example, fluoromethylthio, chlorodifluoromethylthio, bromodifluoromethylthio, trifluoromethylthio, trichloromethylthio, 2,2,2-trifluoroethylthio, 1,1,2,2-tetrafluoroethylthio, fluoroethylthio, pentafluoroethylthio and fluoro-iso-propylthio groups.
The haloalkylsulfinyl group for G, R, W, X, Y and Z may be a straight chain or branched, C.sub.1 -C.sub.4 haloalkylsulfinyl group, including, for example, fluoromethylsulfinyl, chlorodifluoromethylsulfinyl, bromodifluoromethylsulfinyl, trifluoromethylsulfinyl, trichloromethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, 1,1,2,2-tetrafluoroethylsulfinyl, fluoroethylsulfinyl, pentafluoroethylsulfinyl and fluoro-iso-propylsulfinyl groups.
The haloalkylsulfonyl group for G, R, W, X, Y and Z may be a straight chain or branched, C.sub.1 -C.sub.4 haloalkylsulfonyl group, including, for example, fluoromethylsulfonyl, chlorodifluoromethylsulfonyl, bromodifluoromethylsulfonyl, trifluoromethylsulfonyl, trichloromethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, 1,1,2,2-tetrafluoroethylsulfonyl, fluoroethylsulfonyl, pentafluoroethylsulfonyl and fluoro-isopropylsulfonyl groups.
The haloalkenyl group for G, R, T.sup.1 and W may be a straight chain or branched C.sub.2 -C.sub.4 haloalkenyl group, including, for example, 2-chloroethenyl, 2-bromoethenyl- and 2,2-dichloroethenyl groups.
The alkenyloxy group for G, R, R.sup.1, T.sup.1, W, Y and Y.sup.1 may be a straight chain or branched C.sub.2 -C.sub.4 alkenyloxy group, including, for example, allyloxy, 2-propenyloxy, 2-butenyloxy and 2-methyl-2-propenyloxy groups.
The haloalkenyloxy group for G, R, W and Y may be a straight chain or branched C.sub.2 -C.sub.4 haloalkenyloxy group, including, for example, 3-chloro-2-propenyloxy, 3,3-dichloro-2-propenyloxy, 4-chloro-2-butenyloxy, 4,4-dichloro-3-butenyloxy and 4,4-difluoro-3-butenyloxy groups.
The alkenylsulfenyl group for G, R, W, X, Y and Z may be a straight chain or branched C.sub.2 -C.sub.4 alkenylsulfenyl group, including, for example, allylsulfenyl, 2-propenylsulfenyl, 2-butenylsulfenyl and 2-methyl-2-propenylsulfenyl groups.
The alkenylsulfinyl group for G, R, W, X, Y and Z may be a straight chain or branched C.sub.2 -C.sub.4 alkenylsulfinyl group, including, for example, allylsulfinyl, 2-propenylsulfinyl, 2-butenylsulfinyl and 2-methyl-2-propenylsulfinyl groups.
The alkenylsulfonyl group for G, R, W, X, Y and Z may be a straight chain or branched C.sub.2 -C.sub.4 alkenylsulfonyl group, including, for example, allylsulfonyl, 2-propenylsulfonyl, 2-butenylsulfonyl and 2-methyl-2-propenylsulfonyl groups.
The haloalkenylsulfenyl group for G, R, W and Y may be a straight chain or branched C.sub.2 -C.sub.4 haloalkenylsulfenyl group, including, for example, 3-chloro-2-propenylsulfenyl, 4-chloro-2-butenylsulfenyl, 3,3-dichloro-2-propenylsulfenyl, 4,4-dichloro-3-butenylsulfenyl and 4,4-difluoro-3-butenylsulfenyl groups.
The haloalkenylsulfinyl group for G, R, W and Y may be a straight chain or branched C.sub.2 -C.sub.4 haloalkenylsulfinyl group, including, for example, 3-chloro-2-propenylsulfinyl, 3,3-dichloro-2-propenylsulfinyl, 4-chloro-2-butenylsulfinyl, 4,4-dichloro-3-butenylsulfinyl and 4,4-difluoro-3-butenylsulfinyl groups.
The haloalkenylsulfonyl group for G, R, W and Y may be a straight chain or branched C.sub.2 -C.sub.4 haloalkenylsulfonyl group, including, for example, 3-chloro-2-propenylsulfonyl, 3,3-dichloro-2-propenylsulfonyl, 4-chloro-2-butenylsulfonyl, 4,4-dichloro-3-butenylsulfonyl and 4,4-difluoro-3-butenylsulfonyl groups.
The C.sub.2 -C.sub.4 haloalkynyl group for G, R and W includes, for example, chloroethynyl, bromoethynyl, iodoethynyl, 3-chloro-1-propynyl and 3-bromo-1-butynyl groups.
The C.sub.2 -C.sub.4 alkynyloxy group for G, R, W and Y includes, for example, 2-propynyloxy, 2-butynyloxy and 1-methyl-2-propynyloxy groups.
The C.sub.2 -C.sub.4 haloalkynyloxy group for G, R, W and Y includes, for example, 3-chloro-2-propynyloxy, 3-bromo-2-propynyloxy and 3-iodo-2-propynyloxy groups.
The C.sub.2 -C.sub.6 alkynylsulfenyl group for G, R, W and Y includes, for example, 2-propynylsulfenyl, 2-butynylsulfenyl and 1-methyl-2-propynylsulfenyl groups.
The C.sub.2 -C.sub.6 alkynylsulfinyl group for G, R, W and Y includes, for example, 2-propynylsulfinyl, 2-butynylsulfinyl and 1-methyl-2-propynylsulfinyl groups.
The C.sub.2 -C.sub.6 alkynylsulfonyl group for G, R, W and Y includes, for example, 2-propynylsulfonyl, 2-butynylsulfonyl and 1-methyl-2-propynylsulfonyl groups.
The C.sub.2 -C.sub.6 haloalkynylsulfenyl group for G, R, W and Y includes, for example, 3-chloro-2-propynylsulfenyl, 3-bromo-2-propynylsulfenyl and 3-iodo-2-propynylsulfenyl groups.
The C.sub.2 -C.sub.6 haloalkynylsulfinyl group for G, R, W and Y includes, for example, 3-chloro-2-propynylsulfinyl, 3-bromo-2-propynylsulfinyl and 3-iodo-2-propynylsulfinyl groups.
The C.sub.2 -C.sub.6 haloalkynylsulfonyl group for G, R, W and Y includes, for example, 3-chloro-2-propynylsulfonyl, 3-bromo-2-propynylsulfonyl and 3-iodo-2-propynylsulfonyl groups.
The C.sub.2 -C.sub.4 alkylcarbonyloxy group for G, R, W and Y includes, for example, acetoxy, propanoyloxy, butanoyloxy and isopropylcarbonyloxy groups.
The benzoyl group optionally substituted by X for E and G includes, for example, benzoyl, 2-chlorobenzoyl, 3-chlorobenzoyl, 4-chlorobenzoyl, 4-bromobenzoyl, 4-fluorobenzoyl, 3-methylbenzoyl, 4-methylbenzoyl, 4-tert-butylbenzoyl and 3,4-dichlorobenzoyl groups.
Even at low concentration, the compounds of the present invention effectively prevent various pests, which include, for example, so-called agricultural insect pests that injure agricultural and horticultural crops and trees, so-called livestock insect pests that live on livestock and poultry, so-called sanitary insect pests that have various negative influences on the human living environment including houses, so-called stored products insect pests that injure grains stored in storehouses, and also acarids, nematodes, molluscs and crustaceans that live in the same sites as above and injure those mentioned above.
Examples of insect pests, acarids, nematodes, molluscs and crustaceans capable of being exterminated by the compounds of the present invention are mentioned below, which, however, are not limitative.
Insect pests of Lepidoptera, such as rice stem borer (Chilo suppressalis Walker), rice leafroller (Cnaphalocrocis medinalis Guenee), green rice caterpillar (Naranga aenescens Moore), rice skipper (Parnara guttata Bremer et Gvey), diamond back moths (Plutella xylostella Linne), cabbage armyworms (Mamestra brassicae Linnee), common white (Pieris rapae crucivora Boisduval), turnip moth (Agrotis segetum Denis et Schiffermuller), common cutworm (Spodptera litura Fabricius), beet armyworm (Spodoptera exigua Hubner), smaller tea tortrix (Adoxophyes sp.), oriental tea tortrix (Homona magnanima Diakonoff), peach fruit moth (Carposina niponensis Walsingham), oriental fruit moth (Grapholita molesta Busck), summer fruit tortrix (Adoxophyes orana fasciata Walsingham), apple leafminers (Phyllonorycter ringoniella Matsumura), corn earworm (Helicoverpa zea Boddie), tobacco bad worms (Heliothis virescens Fabricius), European corn borer (Ostrinia nubilalis Hubner), fall armyworm (Spodoptera frugiperda J. E. Smith), Codling moth moth (Cydia pomonella Linnee), fall webworms (Hyphantria cunea Drury), etc.;
Insect pests of Hemiptera, such as green rice leafhopper (Nephotettix cincticeps Uhler), brown rice planthoppers (Nilaparvata lugens Stal), green peach aphid (Myzus persicae Sulzer), cotton aphid (Aphis gossypii Glover), greenhouse whitefly (Trialeurodes vaporariorum Westwood), sweetpotato white fly (Bemisia tabaci Gennadius), pear psylla (Psylla pyricola Forster), azalea lace bug (Stephanitis pyrioides Scott), arrowhead scale (Unaspis yanonensis Kuwana), comstock mealybug (Pseudococcus comstocki Kuwana), red wax scale (Ceroplastes rubens Maskell), brown-marmorated stinkbug (Halyomorpha mista Uhler), cabbage bug (Eurydema rugosam Motschulsky), bed bug (Cimex lectularius Linnee), etc.;
Insect pests of Coleoptera, such as twenty-eight-spotted ladybird (Henosepilachna vigintioctopunctata Fabricius), cupreous chafers (Anomala cuprea Hope), ricewater weevil (Lissorhoptrus oryzophilus Kuschel), sweetpotato weevil (Cylas formicarius Fabricius), cucurbit leaf beetle (Aulacophora femoralis Motschulsky), striped flea beetle (Phyllotreta striolata Fablicius), white-spotted longicorn beetle (Anoplophora malasiaca Thomson), pine sawyers (Monochamus alternatus Hope), corn rootworms (Diabrotica spp.), rice weevil (Sitophilus zeamais Motschulsky), lesser rice weevil (Sitophilus oryzae Linne), granary weevils (Sitophilus granarius Linnee), red four beetle (Tribolium castaneum Herbst), etc.;
Insect pests of Diptera, such as legume leafminer (Liriomyza trifolii Burgess), seedcorn maggot (Delia platura Meigen), Hessia fly (Mayetiola destructor Say), melon fly (Dacus (Zengodacus) cucurbitae Coquillett), Mediterranear fruit fly (Ceratitis capitata Wiedemann), house flies (Musca domestica Linne), stable fly (Stomoxys calcitrans Linne), Sheep ked (Melophagus orinus), common cattle grub (Hypoderm lineatum devillers), nothern cattle grub (Hypoderma boris Linnee), sheep botfly (Oestrus ovis Linnee), tsetse fly (Golossina palpalis Robineau-Desvoidy), common gnat (Culex pipiens pallens Coquillett), yellow-fever mosquitoes (Aedes aegypti Linne), Anopheles culicifacies), etc.
Insect pests of Hymenoptera, such as cabbage sawfly (Athalis rosae ruficornis Jakovlev), pine sawfly (Neodiprion sertifer Geoffroy), chestnut sawfly (Apethymus kuri Takeuchi), etc.;
Insect pests of Thysanoptera, such as melon thrips (Thrips palmi Karny), onion thrips (Thrips tabaci Lindeman), western flower thrips (Frankliniella occidentalis Pergande), flower thrip (Frankliniella intonsa Trybom), yellow tea thrip (Scirtothrips dorsalis Hood), etc.;
Insect pests of Dictyoptera, such as smokybrown cockroache (Periplaneta fuliginosa Serville), Japanese cockroach (Periplaneta japonica Karny), German cockroaches (Blattella germanica Linne), etc.;
Insect pests of Orthoptera, such as oriental migratory locust (Locusta migratoria Linne), rice grasshopper (Oxya yezoensis Shiraki), desert locust (Schistocerca gregaria Forskal), etc.;
Insect pests of Isoptera, such as Formosan subterranean termit (Coptotermes formosanus Shiraki), (Reticulitermes (Leucotermes) speratus Kolbe), (Odontotermes formosanus Shirakif), etc.;
Insect pests of Siphonaptera, such as cat fleas (Ctenocephalides felis Bouche), human fleas (Pulex irritans Linne), oriental rat flea (Xenopsylla cheopis Rothschild), etc.;
Insect pests of Mallophaga, such as Chicken bodylouse (Menacanthus stramineus Nitsch), cattle biting louse (Bovicola bovis Linne), etc.;
Insect pests of Anoplura, such as short-nosed cattle louse (Haematopinus eurysternus Nitzsh), hog louse (Haematopinus suis Linne), longnosed cattle louse (Linognathus vituli Linne), little cattle louse (Solenopotes capillatus Enderlein), etc.
Pests of TETRANYCHIDAE, such as citrus red mite (Panonychus citri McGregor), European red mite (Panonychus ulmi Kock), two-spotted spider mite (Tetranychus urticae Koch), Kanzawa spinder mite (Tetranychus kanzawai Kishida), etc.;
Pests of ERIOPHYDAE, such as pink citrus rust mite (Aculops pelekassi Keifor), pear rust mite (Epitrimerus pyri Nalepa), dry bulb mite (Aceria tulipae Keiter), pink tea mite (Acaphylla theae watt), etc.;
Pests of TARSONEMIDAE, such as broad mites (Polyphagotarsonemus latus Banks), cyclamen mite, strawberry mite (Steneotarsonemus pallidus Banks), etc.;
Pests of ACARIDAE, such as mold mite, copra mite, forage mite (Tyrophagus putrescetiae Schrank), bulb mite (Rhizoglyphus robini Claparede), etc.;
Pests of VARROIDAE, such as bee brood mite (Varroa jacobsoni Oudemans), etc.;
Pests of Ixodidae, such as bull ticks (Boophilus microplus Canestrini), (Haemaphysalis longicornis Neumann), etc.;
Pests of Sarcoptidae, such as sarcoptes mange mite (Sarcaptes scabiei Linne), etc.;
Nematodes, such as southern root-knot nematode (Meloidogyne incognita Kofoid et White), northern root-knot nematode (Meloidogyne hapla Chitwood), Cobb root-lesion nematode (Pratylenchus penetraus Cobb), walnut root-lesion nematode (Pratylenchus vulnus Allen et Jensen), potato cyst nematode (Globodera rostochiensis Wollenweber), pine wood nematode (Bursaphelenchus xylophilus Steiner et Buhrer), etc.;
Mollusca, such as apple snail (Pomacea canaliculata Lamarck), (Incilaria pilineata Benson), (Acusta despecta sieboldiana Pfeiffer), (Euhadra peliomphala Pfeiffer), pillbug (Armadillidium vulgare Latreille), etc.;
Crustaceans, such as pillbug (Armadillidium vulgare Latreille), etc.
The plant diseases to be controlled by the compounds of the present invention are as follows:
Blast (Pyricularia oryzae), Helminthosporium leaf spot (Cochliobolus miyabeanus) and Sheath blight (Rhizoctonia solani) of rice,
Powdery mildew (Erysiphe graminis f. sp. hordei, f. sp. tritici), Leaf stripe (Pyrenophora graminea), Net blotch (Pyrenophora teres), Fusarium blight (Gibberella zeae), yellow rust, black stem rust and brown rust (Puccinia striiformis, P. graminis, P. recondita and P. hordei), Snow blight and snow mold (Typhula sp., Micronectriella nivais), Loose smut (Ustilago tritici, U. nuda), Eyespot (Pseudocercorsporella herpotrichoides), Scald and leaft blotch (Rhynchosporium secalis), Speckled blotch (Septoria tritici), and Glume blotch (Leptosphaeria nodorum) of barley and wheat,
Melanose (Diaporthe citri), Scab (Elsinoe fawcetti), and Common green mold and blue mold (Penicillium digitatum, P. italicum) of citrus fruit,
Blossom blight (Sclerotinia mali), Canker (Valsa mali), Powder mildew (Podosphaera leucotricha), Alternaria leaft spot (Alternaria mali) and Scab (Venturia inaequalis) of apple,
Scab (Venturia nashicola), Black spot (Alternaria Kikuchiana) and Rust (Gymnosporangium haraeanum) of pear,
Brown rot (Sclerotinia cinerea), Scab (Cladosporium carpophilum), and Phomopsis rot (Phomopsis sp.) of peach,
Downy mildew (Plasmopara viticola), Anthracnose (Elsinoe ampelina), Ripe rot (Glomerella cingulata), Powdery mildew (Uncinula nacator) and Rust (Phakopsora ampelopsidis) of grape,
Anthracnose (Gloesporium kaki), Powdery mildew (Phyllactinia kakicola), Angular leaf spot (Cercospora kaki), and Circular leaf spot (Mycosphaerella nawae) of persimmon,
Downy mildew (Pseudoperenospora cubensis), Anthracnose (Colletotrichum lagenarium), Powdery mildew (Sphaerotheca fuliginea), and Gummy stem blight (Mycosphaerella melonis) of cucurbit,
Late blight (Phytophthora infestans), Early blight (Alternaria solani) and Leaf mold (Cladosporium fulvam) of tomato.
Brown spot (Phomopsis vexans) and Powdery mildew (Erysiphe cichoracoarum) of egg plant,
Alternaria leaft spot (Alternaria japonica) and white spot (Cerocosporella brassicae) of vegetable of the family crucifers.
Rust (Puccinia allii) of welsh onion.
Purple seed stain (Cercospora kikuchii), Sphaceloma scab (Elsinoe glycines) and Pot and stem blight (Diaporthe phaseololum) of soybean,
Anthracnose (Collectorichum lindemuthianum) of kidney bean.
Leaf spot (Mycosphaerella personatum) and Brown leaf spot (Cercospora arachidicola) of peanut,
Powdery mildew (Erysiphe pisi) of garden pea,
Early blight (Alternaria solani) of potato,
Powdery mildew (Sphaerotheca humuli) of strawberry,
Net blister blight (Exobasidium reticulatum) and White scab (Elsinoe leucospila) of tea,
Brown spot (Alternaria longipes), Powdery mildew (Erysiphe cichoracearum) and Anthracnose (Colletotrichum tabacum) of tobacco,
Cercospora leaft spot (Cercospora beticola) of sugar beat,
Black spot (Diplocarpon rosae) and Powdery mildew (Sphaerotheca pannosa) of rose,
Leaf spot (Septoria chrysanthemiindici) and Rust (Puccinia horiana) of chrysanthemum,
Gray mold (Botrytis cinerea) of various kinds of crops, and,
Sclerotinia rot (Sclerotinia sclerotiorum) of various kinds of crops.
In addition, the compounds of the present invention are effective in preventing the attachment of aquatic organisms, even at extremely low concentrations. Aquatic organisms to which the invention is directed are, for example, shellfishes and algae, such as mussel, barnacle, oyster, hydrozoan, hydra, Serpula, ascidian, seamoss, Bagula, mud pond snail, sea lettuce, green laver, Ectocarpus, etc.
Specifically, the compounds of the present invention can effectively exterminate various pests and phytopathogenic microbes of, for example, Orthoptera, Hemiptera, Lepidoptera, Coleoptera, Hymenoptera, Diptera, Temitidae, and also mites and louses, even when used at low concentrations. In addition, the compounds of the invention are effective in preventing the attachment of various aquatic organisms living in sea water and fresh water to aquatic constructions, etc. On the other hand, the compounds of the present invention contains useful compounds that have few negative influences on mammals, fishes, shellfishes and useful insects.
Of the compounds of the invention, those having CN as E can be produced according to the following methods (Scheme 1).
Scheme 1:
(Method A) ##STR8##
(Method B) ##STR9##
(Method C) ##STR10##
In (Scheme 1), Q, A and B have the same meanings as defined above; L represents a suitable leaving group, such as a chlorine atom, a bromine atom, an iodine atom, an alkoxy group having from 1 to 4 carbon atoms, a phenoxy group, an alkylsulfonyloxy group having from 1 to 4 carbon atoms, a benzenesulfonyloxy group, a toluenesulfonyloxy group, a phenoxy group, a 1-pyrazolyl group or a 1-imidazolyl group; L' represents a halogen atom; and alkyl represents an alkyl group preferably having from 1 to 4 carbon atoms.
Method A in (Scheme 1) is to react an acetonitrile derivative of formula (3) with an acid chloride, ester or amide of formula (4) or with an acid anhydride of formula (5) to give compounds (1') of the present invention. The compound (1') of the invention is optionally reacted with an alkyl halide, an alkyl sulfonate, a trimethylsilyl halide, a sulfonyl chloride, a sulfamoyl chloride, a thiocarbamoyl chloride, an acid chloride or an ester of formula (8) to be converted into compounds (1) of the invention. Depending on the type of B in the compounds (1) of the invention, the compound (1') is reacted with a dihydropyran, an isocyanate or a thioisocyanate to give the compounds (1). In Method A, if the compound of formula (4) or (5) is used in an excessive amount, the compounds (1) can be directly obtained without isolating the compounds (1').
Where Q is bonded to the acrylonitrile moiety via a nitrogen atom, compounds (1') may be produced according to Method B. Method B is to react a heterocyclic compound of formula (6) with a halogenocyanoketone derivative of formula (7) to give compounds (1') of the invention.
Where A is bonded to the acrylonitrile moiety via a nitrogen atom, compounds (1') may be produced according to Method C. Method C is to react a cyanoacetic acid derivative of formula (9) with a heterocyclic compound of formula (10) to give compounds (1') of the invention. As the case may be, the compound of formula (9) will be prepared by reacting an acetonitrile derivative of formula (3), such as that used in Method A, with a carbonic acid ester in the presence of a base.
Of the compounds of the invention, those where E is
Scheme 2:
(Method D) ##STR11##
(Method E) ##STR12##
(Method F) ##STR13##
In (Scheme 2), Q, A, E, B, L, L' and alkyl have the same meanings as above.
Method D in (Scheme 2) is to react a compound of formula (11) with an acid chloride, ester or amide of formula (4) or with an acid anhydride of formula (5) to give the compounds (1') of the present invention. The compound (1') of the invention is optionally reacted with an alkyl halide, an alkyl sulfonate, a trimethylsilyl halide, a sulfonyl chloride, a sulfamoyl chloride, a thiocarbamoyl chloride, an acid chloride or an ester of formula (8) to be converted into the compounds (1) of the invention. Depending on the type of B in the compounds (1) of the invention, the compound (1') is reacted with a dihydropyran, an isocyanate or a thioisocyanate to give the compounds (1). In Method A, if the compound of formula (4) or (5) is used in an excessive amount, the compounds (1) can be directly obtained without isolating the compounds (1').
Where Q is bonded to the ethylene moiety via a nitrogen atom, the compounds (1') may be produced according to Method E. Method E is to react a heterocyclic compound of formula (6) with a compound of formula (12) in the presence of a base to give compounds (1') of the-invention.
Where A is bonded to the ethylene moiety via a nitrogen atom, the compounds (1') may be produced according to Method F. Method F is to react a compound of formula (13) with a heterocyclic compound of formula (10) through dealcoholation to give the compounds (1') of the invention. As the case may be, the compound of formula (13) will be prepared by reacting a compound of formula (11), such as that used in Method D, with a carbonic acid ester in the presence of a base.
If desired, the compounds (1') where E is an alkoxycarbonyl group may be hydrolyzed, decarboxylated and halogenated to give the compounds of the invention where E is a halogen atom. As the case may be, the compounds of the invention where E is a halogen atom may be reacted with a nucleophilic reagent corresponding to E (e.g., triester phosphites, alkyl mercaptans, thiophenols, metal acetylides, metal cyanides, metal azides, nitrites) to give different compounds of the invention. Also as the case may be, the compounds to be obtained through decarboxylation of the compounds (1') where E is an alkoxycarbonyl group may be reacted with an electrophilic reagent under basic conditions to give the compounds of the invention.
As the case may be, the processes of (Scheme 1) and (Scheme 2) are preferably effected in the presence of a base. The base to be used includes, for example, alkali metal alkoxides such as sodium ethoxide, sodium methoxide and t-butoxy potassium; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; organic bases such as triethylamine, pyridine and DBU; organic lithium compounds such as butyl lithium; lithium amides such as lithium diisopropylamide and lithium bistrimethylsilylamide; and sodium hydride.
The reactions of (Scheme 1) and (Scheme 2) may be effected in a solvent that is inert to the reaction. The solvent includes, for example, lower alcohols such as methanol and ethanol; aromatic hydrocarbons such as benzene and toluene; etherd such as diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane and 1,2-diethoxyethane; halogenated hydrocarbons such as methylene chloride, chloroform and 1,2-dichloroethane; amides such as dimethylformamide and dimethylacetamide; acetonitrile; dimethylsulfoxide; and mixed solvents of these. As the case may be, also employable are mixed solvent comprising said solvents and water. Also as the case may be, a quaternary ammonium salt such as tetra-n-butylammonium bromide may be added to the reaction system as a catalyst to obtain good results. The reaction temperature may be freely settled within a range between -30.degree. C. and 200.degree. C. Preferably, the reaction temperature falls between 0.degree. C. and 150.degree. C., or between 0.degree. C. and the boiling point of the solvent if used. The base may be used in an amount of from 0.05 to 10 equivalents, preferably from 0.05 to 3 equivalents, of the reaction substrate.
The compounds of the present invention may be separated from reaction mixtures according to any ordinary methods. If the purification of the compounds of the invention is needed, they can be separated and purified by any ordinary methods of, for example, recrystallization or column chromatography.
Of the compounds of the invention, those having an asymmetric carbon atom include optically-active compounds of (+) form and (-) form.
Methods of producing the compounds (3) to be used in (Scheme 1) are referred to hereinunder. The compounds (3) can be produced according to the following (Scheme 3).
Scheme 3: ##STR14##
1) A benzyl halide, a benzyl alkylsulfonate, a benzyl arylsulfonate, a halomethyl-heterocyclic compound, an alkylsulfonyloxymethyl-heterocyclic compound or an arylsulfonyloxymethyl-heterocyclic compound of formula (14) is reacted with a suitable cyanating reagent to give compounds (3). Alternatively, a phenylacetic acid derivative or a heterocyclic acetic acid derivative is converted into the corresponding amide derivative, which is then dehydrated to give compounds (3).
2) A heterocyclic halide (15) is condensed with a cyanoacetate (16) in the presence of a base to give a compound (17), which is then hydrolyzed and decarboxylated to give compounds (3).
3) To obtain compounds (3) where Q is bonded to the ethylene moiety via a nitrogen atom, a heterocyclic derivative (6) where the nitrogen atom of Q is unsubstituted is reacted with a haloacetonitrile derivative in the presence of a base. Alternatively, the compound (6) is reacted with a compound (18) in the presence of a base to give a compound (17), said compound (18) being obtained through halogenation of a cyanoacetate, and thereafter the compound (17) is hydrolyzed and decarboxylated to obtain the compounds (3).
The compounds (11) to be used in (Scheme 2) can be produced in the same manner as in the production of the compounds (3) mentioned above.
The compounds (7) to be used in (Scheme 1) can be produced by condensing a benzoic acid halide or heterocyclic carboxylic acid halide with a cyanoacetate in the presence of a base followed by halogenating the resulting condensate.
The above-mentioned halomethyl-heterocyclic compounds, alkylsulfonyloxymethyl-heterocyclic compounds and arylsulfonyloxymethyl-heterocyclic compounds can be derived from heterocyclic methane derivatives or heterocyclic carboxylate derivatives that are produced according to ordinary methods (see Alan R. Katritzky, and Charles W. Rees; Comprehensive Heterocyclic Chemistry, Vol. 2, Vol. 3, Vol. 4, Vol. 5 or Vol. 6). To produce the compounds (14) where Q is an oxazol-4-yl or thiazol-4-yl group, a carboxylic acid amide or thioamide can be reacted with 1,3-dichloro-2-propanone.
Examples of the compounds of the present invention are shown in Table 1 to Table 14 below. The abbreviations in these Tables are for the meanings mentioned below:
Me: methyl group, Et: ethyl group, Pr: propyl group, Bu: butyl group, Pen: pentyl group, Hex: hexyl group, Hep: heptyl group, Oct: octyl group, Non: nonyl group, Dec: decyl group, Ph: phenyl group, n: normal, i: iso, sec: secondary, t: tertiary, c: cyclo. ##STR15##
TABLE 1______________________________________ ##STR16## ##STR17## ##STR18## ##STR19## ##STR20## ##STR21## ##STR22## ##STR23## ##STR24## ##STR25## ##STR26## ##STR27## ##STR28## ##STR29## ##STR30## ##STR31## ##STR32## ##STR33## ##STR34## ##STR35## ##STR36## ##STR37## ##STR38## ##STR39## ##STR40## ##STR41## ##STR42## ##STR43## ##STR44## ##STR45## ##STR46## ##STR47## ##STR48## ##STR49## ##STR50## ##STR51## ##STR52## ##STR53## ##STR54## ##STR55## ##STR56##R.sup.1 R.sup.2 R.sup.3 B Y.sup.1 Y.sup.2 Y.sup.3______________________________________2,6-F.sub.2 --Ph H H H H H H2,6-F.sub.2 --Ph H H H H Cl H2,6-F.sub.2 --Ph H H H H Me H2,6-F.sub.2 --Ph H H H H OMe H2,6-F.sub.2 --Ph H H H H SMe H2,6-F.sub.2 --Ph H H H H OCF.sub.3 H2,6-F.sub.2 --Ph H H H H CF.sub.3 H2,6-F.sub.2 --Ph H H H H CO.sub.2 Me H2,6-F.sub.2 --Ph H H H H H Me2,6-F.sub.2 --Ph H H H Me H Me2,6-F.sub.2 --Ph H H H Me H CF.sub.32,6-F.sub.2 --Ph H H H Me H H2,6-F.sub.2 --Ph H H H Me Me Me2,6-F.sub.2 --Ph H H H Me Me H2,6-F.sub.2 --Ph H H H Me Cl Me2,6-F.sub.2 --Ph H H H Me Cl H2,6-F.sub.2 --Ph Cl H H Me Cl Me2,6-F.sub.2 --Ph H H H Et Me Me2,6-F.sub.2 --Ph H H H Et H H2,6-F.sub.2 --Ph H H H nPr Me Me2,6-F.sub.2 --Ph H H H iPr Me Me2,6-F.sub.2 --Ph H H H iPr Cl Me2,6-F.sub.2 --Ph H H H nBu Me Me2,6-F.sub.2 --Ph H H H tBu Me Me2,6-F.sub.2 --Ph H H H Cl Me Me2,6-F.sub.2 --Ph H H H Cl Me H2,6-F.sub.2 --Ph H H H Cl H Me2,6-F.sub.2 --Ph H H H Cl H CF.sub.32,6-F.sub.2 --Ph H H H Cl H H2,6-F.sub.2 --Ph Me H H Cl H H2,6-F.sub.2 --Ph Cl H H Cl H H2,6-F.sub.2 --Ph NO.sub.2 H H Cl H H2,6-F.sub.2 --Ph CO.sub.2 Me H H Cl H H2,6-F.sub.2 --Ph CO.sub.2 Et H H Cl H H2,6-F.sub.2 --Ph H H H Cl Cl Me2,6-F.sub.2 --Ph Me H H Cl Cl Me2,6-F.sub.2 --Ph H Me H Cl Cl Me2,6-F.sub.2 --Ph H Cl H Cl Cl Me2,6-F.sub.2 --Ph Cl H H Cl Cl Me2,6-F.sub.2 --Ph Cl Cl H Cl Cl Me2,6-F.sub.2 --Ph Cl Cl B1 Cl Cl Me2,6-F.sub.2 --Ph Ph H H Cl Cl Me2,6-F.sub.2 --Ph H Ph H Cl Cl Me2,6-F.sub.2 --Ph CF.sub.3 H H Cl Cl Me2,6-F.sub.2 --Ph H CF.sub.3 H Cl Cl Me2,6-F.sub.2 --Ph cPr H H Cl Cl Me2,6-F.sub.2 --Ph H cPr H Cl Cl Me2,6-F.sub.2 --Ph OMe H H Cl Cl Me2,6-F.sub.2 --Ph H OMe H Cl Cl Me2,6-F.sub.2 --Ph NH.sub.2 H H Cl Cl Me2,6-F.sub.2 --Ph H NH.sub.2 H Cl Cl Me2,6-F.sub.2 --Ph NHMe H H Cl Cl Me2,6-F.sub.2 --Ph H NHMe H Cl Cl Me2,6-F.sub.2 --Ph NMe.sub.2 H H Cl Cl Me2,6-F.sub.2 --Ph H NMe.sub.2 H Cl Cl Me2,6-F.sub.2 --Ph NO.sub.2 H H Cl Cl Me2,6-F.sub.2 --Ph H NO.sub.2 H Cl Cl Me2,6-F.sub.2 --Ph CN H H Cl Cl Me2,6-F.sub.2 --Ph H CN H Cl Cl Me2,6-F.sub.2 --Ph OH H H Cl Cl Me2,6-F.sub.2 --Ph H OH H Cl Cl Me2,6-F.sub.2 --Ph CO.sub.2 Me H H Cl Cl Me2,6-F.sub.2 --Ph H CO.sub.2 Me H Cl Cl Me2,6-F.sub.2 --Ph CO.sub.2 Et H H Cl Cl Me2,6-F.sub.2 --Ph H H H Cl Cl H2,6-F.sub.2 --Ph H H H Cl Cl CF.sub.32,6-F.sub.2 --Ph H H H Cl Cl CF.sub.2 H2,6-F.sub.2 --Ph H H H Cl Cl CH.sub.2 OMe2,6-F.sub.2 --Ph H H H Cl Cl COMe2,6-F.sub.2 --Ph H H H Cl Cl Ph2,6-F.sub.2 --Ph H H H Cl Cl CH.sub.2 Ph2,6-F.sub.2 --Ph H H H Cl CF.sub.3 Me2,6-F.sub.2 --Ph H H H Br Me Me2,6-F.sub.2 --Ph H H H Me Br Me2,6-F.sub.2 --Ph H H H Me Br H2,6-F.sub.2 --Ph H H H Br H H2,6-F.sub.2 --Ph H H H OMe Me Me2,6-F.sub.2 --Ph H H H Me OMe Me2,6-F.sub.2 --Ph H H H OMe H H2,6-F.sub.2 --Ph H H H H OMe H2,6-F.sub.2 --Ph H H H Cl OMe Me2,6-F.sub.2 --Ph H H H OCF.sub.3 Me Me2,6-F.sub.2 --Ph H H H OCF.sub.3 Cl Me2,6-F.sub.2 --Ph H H H OCF.sub.3 H H2,6-F.sub.2 --Ph H H H Me OCF.sub.3 Me2,6-F.sub.2 --Ph H H H Cl OCF.sub.3 Me2,6-F.sub.2 --Ph H H H SMe Cl Me2,6-F.sub.2 --Ph H H H Me SMe Me2,6-F.sub.2 --Ph H H H Cl SMe Me2,6-F.sub.2 --Ph H H H SMe H H2,6-F.sub.2 --Ph H H H SOMe Cl Me2,6-F.sub.2 --Ph H H H Cl SOMe Me2,6-F.sub.2 --Ph H H H SOMe H H2,6-F.sub.2 --Ph H H H SO.sub.2 Me Cl Me2,6-F.sub.2 --Ph H H H Cl SO.sub.2 Me Me2,6-F.sub.2 --Ph H H H SO.sub.2 Me H H2,6-F.sub.2 --Ph H H H CF.sub.3 Me Me2,6-F.sub.2 --Ph H H H CF.sub.3 Cl H2,6-F.sub.2 --Ph H H H CF.sub.3 Cl Me2,6-F.sub.2 --Ph Me H H CF.sub.3 Cl Me2,6-F.sub.2 --Ph Cl H H CF.sub.3 Cl Me2,6-F.sub.2 --Ph Br H H CF.sub.3 Cl Me2,6-F.sub.2 --Ph CF.sub.3 H H CF.sub.3 Cl Me2,6-F.sub.2 --Ph NO.sub.2 H H CF.sub.3 Cl Me2,6-F.sub.2 --Ph CN H H CF.sub.3 Cl Me2,6-F.sub.2 --Ph CO.sub.2 Me H H CF.sub.3 Cl Me2,6-F.sub.2 --Ph CO.sub.2 Et H H CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H H CF.sub.3 Cl CF.sub.32,6-F.sub.2 --Ph H H H CF.sub.3 Cl CF.sub.2 H2,6-F.sub.2 --Ph H H H CF.sub.3 Cl CH.sub.2 OMe2,6-F.sub.2 --Ph H H H CF.sub.3 Cl COCH.sub.32,6-F.sub.2 --Ph H H H CF.sub.3 H Me2,6-F.sub.2 --Ph H H H CF.sub.3 H H2,6-F.sub.2 --Ph H H H CF.sub.3 Br Me2,6-F.sub.2 --Ph H H H CF.sub.3 SMe Me2,6-F.sub.2 --Ph H H H CF.sub.3 SOMe Me2,6-F.sub.2 --Ph H H H CF.sub.3 SO.sub.2 Me Me2,6-F.sub.2 --Ph H H H CF.sub.3 CF.sub.3 Me2,6-F.sub.2 --Ph H H H CF.sub.3 NO.sub.2 Me2,6-F.sub.2 --Ph H H H CF.sub.3 CN Me2,6-F.sub.2 --Ph H H H CF.sub.3 NHMe Me2,6-F.sub.2 --Ph H H H CF.sub.3 NMe.sub.2 Me2,6-F.sub.2 --Ph H H H CF.sub.3 Ph Me2,6-F.sub.2 --Ph H H H CF.sub.3 CH.sub.2 Ph Me2,6-F.sub.2 --Ph H H H CF.sub.3 OPh Me2,6-F.sub.2 --Ph H H H CF.sub.3 OH Me2,6-F.sub.2 --Ph H H H CF.sub.3 CO.sub.2 Me Me2,6-F.sub.2 --Ph H H H CF.sub.3 OMe Me2,6-F.sub.2 --Ph H H H CF.sub.3 OCF.sub.3 Me2,6-F.sub.2 --Ph H H H CF.sub.3 OCF.sub.2 H Me2,6-F.sub.2 --Ph H H H CF.sub.3 OCF.sub.2 H CF.sub.2 H2,6-F.sub.2 --Ph H H H NO.sub.2 CF.sub.3 Me2,6-F.sub.2 --Ph H H H NO.sub.2 Cl Me2,6-F.sub.2 --Ph H H H NO.sub.2 Me Me2,6-F.sub.2 --Ph H H H NO.sub.2 H H2,6-F.sub.2 --Ph H H H Cl NO.sub.2 Me2,6-F.sub.2 --Ph H H H CN CF.sub.3 Me2,6-F.sub.2 --Ph H H H CN Cl Me2,6-F.sub.2 --Ph H H H CN Me Me2,6-F.sub.2 --Ph H H H CN H H2,6-F.sub.2 --Ph H H H Cl CN Me2,6-F.sub.2 --Ph H H H Br CN Me2,6-F.sub.2 --Ph H H H NHMe Me Me2,6-F.sub.2 --Ph H H H NHMe Cl Me2,6-F.sub.2 --Ph H H H NHMe H H2,6-F.sub.2 --Ph H H H Cl NHMe Me2,6-F.sub.2 --Ph H H H NMe.sub.2 Me Me2,6-F.sub.2 --Ph H H H NMe.sub.2 Cl Me2,6-F.sub.2 --Ph H H H NMe.sub.2 H H2,6-F.sub.2 --Ph H H H Cl NMe.sub.2 Me2,6-F.sub.2 --Ph H H H Ph Cl Me2,6-F.sub.2 --Ph H H H Ph H H2,6-F.sub.2 --Ph H H H Cl Ph Me2,6-F.sub.2 --Ph H H H CH.sub.2 Ph Me Me2,6-F.sub.2 --Ph H H H CH.sub.2 Ph H H2,6-F.sub.2 --Ph H H H Cl CH.sub.2 Ph Me2,6-F.sub.2 --Ph H H H OPh Cl Me2,6-F.sub.2 --Ph H H H OPh H H2,6-F.sub.2 --Ph H H H Cl OPh Me2,6-F.sub.2 --Ph H H H OH Me Me2,6-F.sub.2 --Ph H H H OH H H2,6-F.sub.2 --Ph H H H Cl OH Me2,6-F.sub.2 --Ph H H H CO.sub.2 Me Me Me2,6-F.sub.2 --Ph H H H CO.sub.2 Me Cl Me2,6-F.sub.2 --Ph H H H CO.sub.2 Me H H2,6-F.sub.2 --Ph H H H cPr Me Me2,6-F.sub.2 --Ph H H H cPr Cl Me2,6-F.sub.2 --Ph H H B1 Cl Cl Me2,6-F.sub.2 --Ph Cl H B1 Cl Cl Me2,6-F.sub.2 --Ph H H B2 Cl Cl Me2,6-F.sub.2 --Ph H H B3 Cl Cl Me2,6-F.sub.2 --Ph H H B4 Cl Cl Me2,6-F.sub.2 --Ph Cl H B4 Cl Cl Me2,6-F.sub.2 --Ph Cl Me B4 Cl Cl Me2,6-F.sub.2 --Ph NO.sub.2 H B4 Cl Cl Me2,6-F.sub.2 --Ph CO.sub.2 Me H B4 Cl Cl Me2,6-F.sub.2 --Ph CO.sub.2 Et H B4 Cl Cl Me2,6-F.sub.2 --Ph H H B5 Cl Cl Me2,6-F.sub.2 --Ph Cl H B5 Cl Cl Me2,6-F.sub.2 --Ph H H B6 Cl Cl Me2,6-F.sub.2 --Ph Cl H B6 Cl Cl Me2,6-F.sub.2 --Ph NO.sub.2 H B6 Cl Cl Me2,6-F.sub.2 --Ph CO.sub.2 Me H B6 Cl Cl Me2,6-F.sub.2 --Ph CO.sub.2 Et H B6 Cl Cl Me2,6-F.sub.2 --Ph H H B7 Cl Cl Me2,6-F.sub.2 --Ph Cl H B7 Cl Cl Me2,6-F.sub.2 --Ph NO.sub.2 H B7 Cl Cl Me2,6-F.sub.2 --Ph CO.sub.2 Me H B7 Cl Cl Me2,6-F.sub.2 --Ph CO.sub.2 Et H B7 Cl Cl Me2,6-F.sub.2 --Ph H H B8 Cl Cl Me2,6-F.sub.2 --Ph H H B9 Cl Cl Me2,6-F.sub.2 --Ph H H B10 Cl Cl Me2,6-F.sub.2 --Ph H H B11 Cl Cl Me2,6-F.sub.2 --Ph H H B12 Cl Cl Me2,6-F.sub.2 --Ph H H B13 Cl Cl Me2,6-F.sub.2 --Ph H H B14 Cl Cl Me2,6-F.sub.2 --Ph H H B15 Cl Cl Me2,6-F.sub.2 --Ph H H B16 Cl Cl Me2,6-F.sub.2 --Ph H H B17 Cl Cl Me2,6-F.sub.2 --Ph H H B18 Cl Cl Me2,6-F.sub.2 --Ph H H B19 Cl Cl Me2,6-F.sub.2 --Ph H H B20 Cl Cl Me2,6-F.sub.2 --Ph H H B21 Cl Cl Me2,6-F.sub.2 --Ph H H B22 Cl Cl Me2,6-F.sub.2 --Ph H H B23 Cl Cl Me2,6-F.sub.2 --Ph H H B24 Cl Cl Me2,6-F.sub.2 --Ph H H B25 Cl Cl Me2,6-F.sub.2 --Ph H H B26 Cl Cl Me2,6-F.sub.2 --Ph H H B27 Cl Cl Me2,6-F.sub.2 --Ph H H B28 Cl Cl Me2,6-F.sub.2 --Ph H H B29 Cl Cl Me2,6-F.sub.2 --Ph H H B30 Cl Cl Me2,6-F.sub.2 --Ph H H B31 Cl Cl Me2,6-F.sub.2 --Ph H H B32 Cl Cl Me2,6-F.sub.2 --Ph H H B33 Cl Cl Me2,6-F.sub.2 --Ph H H B34 Cl Cl Me2,6-F.sub.2 --Ph H H Na Cl Cl Me2,6-F.sub.2 --Ph H H K Cl Cl Me2,6-F.sub.2 --Ph H H B1 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B2 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B3 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B4 CF.sub.3 Cl Me2,6-F.sub.2 --Ph Me H B4 CF.sub.3 Cl Me2,6-F.sub.2 --Ph Cl H B4 CF.sub.3 Cl Me2,6-F.sub.2 --Ph NO.sub.2 H B4 CF.sub.3 Cl Me2,6-F.sub.2 --Ph CO.sub.2 Me H B4 CF.sub.3 Cl Me2,6-F.sub.2 --Ph CO.sub.2 Et H B4 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B5 CF.sub.3 Cl Me2,6-F.sub.2 --Ph Cl H B5 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B6 CF.sub.3 Cl Me2,6-F.sub.2 --Ph Me H B6 CF.sub.3 Cl Me2,6-F.sub.2 --Ph Cl H B6 CF.sub.3 Cl Me2,6-F.sub.2 --Ph NO.sub.2 H B6 CF.sub.3 Cl Me2,6-F.sub.2 --Ph CO.sub.2 Me H B6 CF.sub.3 Cl Me2,6-F.sub.2 --Ph CO.sub.2 Et H B6 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B7 CF.sub.3 Cl Me2,6-F.sub.2 --Ph Me H B7 CF.sub.3 Cl Me2,6-F.sub.2 --Ph Cl H B7 CF.sub.3 Cl Me2,6-F.sub.2 --Ph NO.sub.2 H B7 CF.sub.3 Cl Me2,6-F.sub.2 --Ph CO.sub.2 Me H B7 CF.sub.3 Cl Me2,6-F.sub.2 --Ph CO.sub.2 Et H B7 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B8 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B9 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B10 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B11 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B12 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B13 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B14 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B15 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B16 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B17 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B18 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B19 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B20 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B21 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B22 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B23 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B24 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B25 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B26 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B27 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B28 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B29 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B30 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B31 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B32 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B33 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B34 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H Na CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H K CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B1 Cl H H2,6-F.sub.2 --Ph H H B2 Cl H H2,6-F.sub.2 --Ph H H B3 Cl H H2,6-F.sub.2 --Ph H H B4 Cl H H2,6-F.sub.2 --Ph Me H B4 Cl H H2,6-F.sub.2 --Ph Cl H B4 Cl H H2,6-F.sub.2 --Ph NO.sub.2 H B4 Cl H H2,6-F.sub.2 --Ph CO.sub.2 Me H B4 Cl H H2,6-F.sub.2 --Ph CO.sub.2 Et H B4 Cl H H2,6-F.sub.2 --Ph H H B5 Cl H H2,6-F.sub.2 --Ph H H B6 Cl H H2,6-F.sub.2 --Ph NO.sub.2 H B6 Cl H H2,6-F.sub.2 --Ph H H B7 Cl H H2,6-F.sub.2 --Ph Me H B7 Cl H H2,6-F.sub.2 --Ph Cl H B7 Cl H H2,6-F.sub.2 --Ph NO.sub.2 H B7 Cl H H2,6-F.sub.2 --Ph CO.sub.2 Me H B7 Cl H H2,6-F.sub.2 --Ph CO.sub.2 Et H B7 Cl H H2,6-F.sub.2 --Ph H H B8 Cl H H2,6-F.sub.2 --Ph H H B9 Cl H H2,6-F.sub.2 --Ph H H B10 Cl H H2,6-F.sub.2 --Ph H H B11 Cl H H2,6-F.sub.2 --Ph H H B12 Cl H H2,6-F.sub.2 --Ph H H B13 Cl H H2,6-F.sub.2 --Ph H H B14 Cl H H2,6-F.sub.2 --Ph H H B15 Cl H H2,6-F.sub.2 --Ph H H B16 Cl H H2,6-F.sub.2 --Ph H H B17 Cl H H2,6-F.sub.2 --Ph H H B18 Cl H H2,6-F.sub.2 --Ph H H B19 Cl H H2,6-F.sub.2 --Ph H H B20 Cl H H2,6-F.sub.2 --Ph H H B21 Cl H H2,6-F.sub.2 --Ph H H B22 Cl H H2,6-F.sub.2 --Ph H H B23 Cl H H2,6-F.sub.2 --Ph H H B24 Cl H H2,6-F.sub.2 --Ph H H B25 Cl H H2,6-F.sub.2 --Ph H H B26 Cl H H2,6-F.sub.2 --Ph H H B27 Cl H H2,6-F.sub.2 --Ph H H B28 Cl H H2,6-F.sub.2 --Ph H H B29 Cl H H2,6-F.sub.2 --Ph H H B30 Cl H H2,6-F.sub.2 --Ph H H B31 Cl H H2,6-F.sub.2 --Ph H H B32 Cl H H2,6-F.sub.2 --Ph H H B33 Cl H H2,6-F.sub.2 --Ph H H B34 Cl H H2,6-F.sub.2 --Ph H H Na Cl H H2,6-F.sub.2 --Ph H H K Cl H HtBu H H H H H MetBu H H H Me H MetBu H H H Me H CF.sub.3tBu H H B7 Me H HtBu H H H Me Me MetBu H H H Me Cl MetBu Cl H H Me Cl MetBu H H H Et Me MetBu H H B8 Et H HtBu H H H Cl Me MetBu H H H Cl Me HtBu H H H Cl H MetBu H H H Cl H CF.sub.3tBu H H H Cl H HtBu Me H B7 Cl H HtBu Cl H B7 Cl H HtBu NO.sub.2 H B7 Cl H HtBu CO.sub.2 Me H B7 Cl H HtBu CO.sub.2 Et H B7 Cl H HtBu H H H Cl Cl MetBu Me H H Cl Cl MetBu Cl H H Cl Cl MetBu CF.sub.3 H H Cl Cl MetBu cPr H H Cl Cl MetBu OMe H H Cl Cl MetBu NO.sub.2 H H Cl Cl MetBu CN H H Cl Cl MetBu CO.sub.2 Me H H Cl Cl MetBu CO.sub.2 Et H H Cl Cl MetBu H H H Cl Cl HtBu H H H Cl Cl CF.sub.3tBu H H H Cl Cl CF.sub.2 HtBu H H H Cl Cl CH.sub.2 OMetBu H H H Cl Cl COMetBu H H H Cl CF.sub.3 MetBu H H H Br Me MetBu H H H Me Br MetBu H H H Me Br HtBu H H B34 Br H HtBu H H H OMe Me MetBu H H H Me OMe MetBu H H H OMe H HtBu H H H Cl OMe MetBu H H H OCF.sub.3 Me MetBu H H H OCF.sub.3 Cl MetBu H H H OCF.sub.3 H HtBu H H H Me OCF.sub.3 MetBu H H H Cl OCF.sub.3 MetBu H H H SMe Cl MetBu H H H Me SMe MetBu H H H Cl SMe MetBu H H B7 SMe H HtBu H H H CF.sub.3 Me MetBu H H H CF.sub.3 Cl HtBu H H H CF.sub.3 Cl MetBu Me H H CF.sub.3 Cl MetBu Cl H H CF.sub.3 Cl MetBu Br H H CF.sub.3 Cl MetBu CF.sub.3 H H CF.sub.3 Cl MetBu NO.sub.2 H H CF.sub.3 Cl MetBu CN H H CF.sub.3 Cl MetBu CO.sub.2 Me H H CF.sub.3 Cl MetBu CO.sub.2 Et H H CF.sub.3 Cl MetBu H H H CF.sub.3 Cl CF.sub.3tBu H H H CF.sub.3 Cl CF.sub.2 HtBu H H H CF.sub.3 Cl CH.sub.2 OMetBu H H H CF.sub.3 Cl COCH.sub.3tBu H H H CF.sub.3 H MetBu H H H CF.sub.3 H MetBu H H H CF.sub.3 Br MetBu H H H CF.sub.3 SMe MetBu H H H CF.sub.3 SOMe MetBu H H H CF.sub.3 SO.sub.2 Me MetBu H H H CF.sub.3 CF.sub.3 MetBu H H H CF.sub.3 NO.sub.2 MetBu H H H CF.sub.3 CN MetBu H H H CF.sub.3 NHMe MetBu H H H CF.sub.3 NMe.sub.2 MetBu H H H CF.sub.3 OH MetBu H H H CF.sub.3 CO.sub.2 Me MetBu H H H CF.sub.3 OMe MetBu H H H CF.sub.3 OCF.sub.3 MetBu H H H CF.sub.3 OCF.sub.2 H MetBu H H H CF.sub.3 OCF.sub.2 H CF.sub.2 HtBu H H H NO.sub.2 Cl MetBu H H H NO.sub.2 Me MetBu H H H NO.sub.2 H HtBu H H H Cl NO.sub.2 MetBu H H H CN Cl MetBu H H H CN Me MetBu H H H CN H HtBu H H H Cl CN MetBu H H H NMe.sub.2 H HtBu H H H Cl NMe.sub.2 MetBu H H H OH Me MetBu H H H OH H HtBu H H H Cl OH MetBu H H H CO.sub.2 Me Me MetBu H H H CO.sub.2 Me Cl MetBu H H H CO.sub.2 Me H HtBu H H B1 Cl Cl MetBu Cl H B1 Cl Cl MetBu H H B2 Cl Cl MetBu H H B3 Cl Cl MetBu H H B4 Cl Cl MetBu Me H B4 Cl Cl MetBu Cl H B4 Cl Cl MetBu NO.sub.2 H B4 Cl Cl MetBu CO.sub.2 Me H B4 Cl Cl MetBu CO.sub.2 Et H B4 Cl Cl MetBu H H B5 Cl Cl MetBu H H B6 Cl Cl MetBu Cl H B6 Cl Cl MetBu H H B7 Cl Cl MetBu Me H B7 Cl Cl MetBu Cl H B7 Cl Cl MetBu NO.sub.2 H B7 Cl Cl MetBu CO.sub.2 Me H B7 Cl Cl MetBu CO.sub.2 Et H B7 Cl Cl MetBu H H B8 Cl Cl MetBu H H B9 Cl Cl MetBu H H B10 Cl Cl MetBu H H B11 Cl Cl MetBu H H B12 Cl Cl MetBu H H B13 Cl Cl MetBu H H B14 Cl Cl MetBu H H B15 Cl Cl MetBu H H B16 Cl Cl MetBu H H B17 Cl Cl MetBu H H B18 Cl Cl MetBu H H B19 Cl Cl MetBu H H B20 Cl Cl MetBu H H B21 Cl Cl MetBu H H B22 Cl Cl MetBu H H B23 Cl Cl MetBu H H B24 Cl Cl MetBu H H B25 Cl Cl MetBu H H B26 Cl Cl MetBu H H B27 Cl Cl MetBu H H B28 Cl Cl MetBu H H B29 Cl Cl MetBu H H B30 Cl Cl MetBu H H B31 Cl Cl MetBu H H B32 Cl Cl MetBu H H B33 Cl Cl MetBu H H B34 Cl Cl MetBu H H Na Cl Cl MetBu H H K Cl Cl MetBu H H B1 CF.sub.3 Cl MetBu H H B2 CF.sub.3 Cl MetBu H H B3 CF.sub.3 Cl MetBu H H B4 CF.sub.3 Cl MetBu Me H B4 CF.sub.3 Cl MetBu Cl H B4 CF.sub.3 Cl MetBu NO.sub.2 H B4 CF.sub.3 Cl MetBu CO.sub.2 Me H B4 CF.sub.3 Cl MetBu CO.sub.2 Et H B4 CF.sub.3 Cl MetBu H H B5 CF.sub.3 Cl MetBu H H B6 CF.sub.3 Cl MetBu Cl H B6 CF.sub.3 Cl MetBu H H B7 CF.sub.3 Cl MetBu Me H B7 CF.sub.3 Cl MetBu Cl H B7 CF.sub.3 Cl MetBu NO.sub.2 H B7 CF.sub.3 Cl MetBu CO.sub.2 Me H B7 CF.sub.3 Cl MetBu CO.sub.2 Et H B7 CF.sub.3 Cl MetBu H H B8 CF.sub.3 Cl MetBu H H B9 CF.sub.3 Cl MetBu H H B10 CF.sub.3 Cl MetBu H H B11 CF.sub.3 Cl MetBu H H B12 CF.sub.3 Cl MetBu H H B13 CF.sub.3 Cl MetBu H H B14 CF.sub.3 Cl MetBu H H B15 CF.sub.3 Cl MetBu H H B16 CF.sub.3 Cl MetBu H H B17 CF.sub.3 Cl MetBu H H B18 CF.sub.3 Cl MetBu H H B19 CF.sub.3 Cl MetBu H H B20 CF.sub.3 Cl MetBu H H B21 CF.sub.3 Cl MetBu H H B22 CF.sub.3 Cl MetBu H H B23 CF.sub.3 Cl MetBu H H B24 CF.sub.3 Cl MetBu H H B25 CF.sub.3 Cl MetBu H H B26 CF.sub.3 Cl MetBu H H B27 CF.sub.3 Cl MetBu H H B28 CF.sub.3 Cl MetBu H H B29 CF.sub.3 Cl MetBu H H B30 CF.sub.3 Cl MetBu H H B31 CF.sub.3 Cl MetBu H H B32 CF.sub.3 Cl MetBu H H B33 CF.sub.3 Cl MetBu H H B34 CF.sub.3 Cl MetBu H H Na CF.sub.3 Cl MetBu H H K CF.sub.3 Cl MetBu H H B1 Cl H HtBu H H B2 Cl H HtBu H H B3 Cl H HtBu H H B4 Cl H HtBu H H B5 Cl H HtBu H H B6 Cl H HtBu H H B7 Cl H HtBu H H B8 Cl H HtBu H H B9 Cl H HtBu H H B10 Cl H HtBu H H B11 Cl H HtBu H H B12 Cl H HtBu H H B13 Cl H HtBu H H B14 Cl H HtBu H H B15 Cl H HtBu H H B16 Cl H HtBu H H B17 Cl H HtBu H H B18 Cl H HtBu H H B19 Cl H HtBu H H B20 Cl H HtBu H H B21 Cl H HtBu H H B22 Cl H HtBu H H B23 Cl H HtBu H H B24 Cl H HtBu H H B25 Cl H HtBu H H B26 Cl H HtBu H H B27 Cl H HtBu H H B28 Cl H HtBu H H B29 Cl H HtBu H H B30 Cl H HtBu H H B31 Cl H HtBu H H B32 Cl H HtBu H H B33 Cl H HtBu H H B34 Cl H HtBu H H Na Cl H HtBu H H K Cl H H2-pyridyl H H H H H Me2-pyridyl H H H Me H Me2-pyridyl H H H Me H CF.sub.32-pyridyl H H B7 Me H H2-pyridyl H H H Me Me Me2-pyridyl H H H Me Cl Me2-pyridyl Cl H H Me Cl Me2-pyridyl H H H Et Me Me2-pyridyl H H H Et H H2-pyridyl H H H Cl Me Me2-pyridyl H H H Cl Me H2-pyridyl H H H Cl H Me2-pyridyl H H H Cl H CF.sub.32-pyridyl H H B7 Cl H H2-pyridyl Me H B7 Cl H H2-pyridyl Cl H B7 Cl H H2-pyridyl CF.sub.3 H B7 Cl H H2-pyridyl cPr H B7 Cl H H2-pyridyl OMe H B7 Cl H H2-pyridyl NO.sub.2 H B7 Cl H H2-pyridyl CN H B7 Cl H H2-pyridyl CO.sub.2 Me H B7 Cl H H2-pyridyl CO.sub.2 Et H B7 Cl H H2-pyridyl H H H Cl Cl Me2-pyridyl Me H H Cl Cl Me2-pyridyl Cl H H Cl Cl Me2-pyridyl CF.sub.3 H H Cl Cl Me2-pyridyl cPr H H Cl Cl Me2-pyridyl OMe H H Cl Cl Me2-pyridyl NO.sub.2 H H Cl Cl Me2-pyridyl CN H H Cl Cl Me2-pyridyl CO.sub.2 Me H H Cl Cl Me2-pyridyl CO.sub.2 Et H H Cl Cl Me2-pyridyl H H H Cl Cl H2-pyridyl H H H Cl Cl CF.sub.32-pyridyl H H H Cl Cl CF.sub.2 H2-pyridyl H H H Cl Cl CH.sub.2 OMe2-pyridyl H H H Cl Cl COMe2-pyridyl H H H Cl CF.sub.3 Me2-pyridyl H H H Br Me Me2-pyridyl H H H Me Br Me2-pyridyl H H H Me Br H2-pyridyl H H H Br H H2-pyridyl H H H OMe Me Me2-pyridyl H H H Me OMe Me2-pyridyl H H B7 OMe H H2-pyridyl H H H Cl OMe Me2-pyridyl H H H OCF.sub.3 Me Me2-pyridyl H H H OCF.sub.3 Cl Me2-pyridyl H H B7 OCF.sub.3 H H2-pyridyl H H H Me OCF.sub.3 Me2-pyridyl H H H Cl OCF.sub.3 Me2-pyridyl H H H SMe Cl Me2-pyridyl H H H Me SMe Me2-pyridyl H H H Cl SMe Me2-pyridyl H H B7 SMe H H2-pyridyl H H H CF.sub.3 Me Me2-pyridyl H H H CF.sub.3 Cl H2-pyridyl H H H CF.sub.3 Cl Me2-pyridyl Me H H CF.sub.3 Cl Me2-pyridyl Cl H H CF.sub.3 Cl Me2-pyridyl Br H H CF.sub.3 Cl Me2-pyridyl CF.sub.3 H H CF.sub.3 Cl Me2-pyridyl NO.sub.2 H H CF.sub.3 Cl Me2-pyridyl CN H H CF.sub.3 Cl Me2-pyridyl CO.sub.2 Me H H CF.sub.3 Cl Me2-pyridyl CO.sub.2 Et H H CF.sub.3 Cl Me2-pyridyl H H H CF.sub.3 Cl CF.sub.32-pyridyl H H H CF.sub.3 Cl CF.sub.2 H2-pyridyl H H H CF.sub.3 Cl CH.sub.2 OMe2-pyridyl H H H CF.sub.3 Cl COCH.sub.32-pyridyl H H H CF.sub.3 H Me2-pyridyl H H H CF.sub.3 H H2-pyridyl H H H CF.sub.3 Br Me2-pyridyl H H H CF.sub.3 SMe Me2-pyridyl H H H CF.sub.3 SOMe Me2-pyridyl H H H CF.sub.3 SO.sub.2 Me Me2-pyridyl H H H CF.sub.3 CF.sub.3 Me2-pyridyl H H H CF.sub.3 NO.sub.2 Me2-pyridyl H H H CF.sub.3 CN Me2-pyridyl H H H CF.sub.3 NHMe Me2-pyridyl H H H CF.sub.3 NMe.sub.2 Me2-pyridyl H H H CF.sub.3 OH Me2-pyridyl H H H CF.sub.3 CO.sub.2 Me Me2-pyridyl H H H CF.sub.3 OMe Me2-pyridyl H H H CF.sub.3 OCF.sub.3 Me2-pyridyl H H H CF.sub.3 OCF.sub.2 H Me2-pyridyl H H H CF.sub.3 OCF.sub.2 H CF.sub.2 H2-pyridyl H H H NO.sub.2 Cl Me2-pyridyl H H H NO.sub.2 Me Me2-pyridyl H H B7 NO.sub.2 H H2-pyridyl H H H Cl NO.sub.2 Me2-pyridyl H H H CN Cl Me2-pyridyl H H H CN Me Me2-pyridyl H H H CN H H2-pyridyl H H H Cl CN Me2-pyridyl H H H NMe.sub.2 H H2-pyridyl H H H Cl NMe.sub.2 Me2-pyridyl H H H OH Me Me2-pyridyl H H H OH H H2-pyridyl H H H Cl OH Me2-pyridyl H H H CO.sub.2 Me Me Me2-pyridyl H H H CO.sub.2 Me Cl Me2-pyridyl H H H CO.sub.2 Me H H2-pyridyl H H B1 Cl Cl Me2-pyridyl H H B2 Cl Cl Me2-pyridyl H H B3 Cl Cl Me2-pyridyl H H B4 Cl Cl Me2-pyridyl H H B5 Cl Cl Me2-pyridyl H H B6 Cl Cl Me2-pyridyl H H B7 Cl Cl Me2-pyridyl Cl H B7 Cl Cl Me2-pyridyl H H B8 Cl Cl Me2-pyridyl H H B9 Cl Cl Me2-pyridyl H H B10 Cl Cl Me2-pyridyl H H B11 Cl Cl Me2-pyridyl H H B12 Cl Cl Me2-pyridyl H H B13 Cl Cl Me2-pyridyl H H B14 Cl Cl Me2-pyridyl H H B15 Cl Cl Me2-pyridyl H H B16 Cl Cl Me2-pyridyl H H B17 Cl Cl Me2-pyridyl H H B18 Cl Cl Me2-pyridyl H H B19 Cl Cl Me2-pyridyl H H B20 Cl Cl Me2-pyridyl H H B21 Cl Cl Me2-pyridyl H H B22 Cl Cl Me2-pyridyl H H B23 Cl Cl Me2-pyridyl H H B24 Cl Cl Me2-pyridyl H H B25 Cl Cl Me2-pyridyl H H B26 Cl Cl Me2-pyridyl H H B27 Cl Cl Me2-pyridyl H H B28 Cl Cl Me2-pyridyl H H B29 Cl Cl Me2-pyridyl H H B30 Cl Cl Me2-pyridyl H H B31 Cl Cl Me2-pyridyl H H B32 Cl Cl Me2-pyridyl H H B33 Cl Cl Me2-pyridyl H H B34 Cl Cl Me2-pyridyl H H Na Cl Cl Me2-pyridyl H H K Cl Cl Me2-pyridyl H H B1 CF.sub.3 Cl Me2-pyridyl H H B2 CF.sub.3 Cl Me2-Pyridyl H H B3 CF.sub.3 Cl Me2-pyridyl H H B4 CF.sub.3 Cl Me2-pyridyl Cl H B4 CF.sub.3 Cl Me2-pyridyl CO.sub.2 Me H B4 CF.sub.3 Cl Me2-pyridyl H H B5 CF.sub.3 Cl Me2-pyridyl H H B6 CF.sub.3 Cl Me2-pyridyl H H B7 CF.sub.3 Cl Me2-pyridyl Cl H B7 CF.sub.3 Cl Me2-pyridyl NO.sub.2 H B7 CF.sub.3 Cl Me2-pyridyl CO.sub.2 Me H B7 CF.sub.3 Cl Me2-pyridyl H H B8 CF.sub.3 Cl Me2-pyridyl H H B9 CF.sub.3 Cl Me2-pyridyl H H B10 CF.sub.3 Cl Me2-pyridyl H H B11 CF.sub.3 Cl Me2-pyridyl H H B12 CF.sub.3 Cl Me2-pyridyl H H B13 CF.sub.3 Cl Me2-pyridyl H H B14 CF.sub.3 Cl Me2-pyridyl H H B15 CF.sub.3 Cl Me2-pyridyl H H B16 CF.sub.3 Cl Me2-pyridyl H H B17 CF.sub.3 Cl Me2-pyridyl H H B18 CF.sub.3 Cl Me2-pyridyl H H B19 CF.sub.3 Cl Me2-pyridyl H H B20 CF.sub.3 Cl Me2-pyridyl H H B21 CF.sub.3 Cl Me2-pyridyl H H B22 CF.sub.3 Cl Me2-pyridyl H H B23 CF.sub.3 Cl Me2-pyridyl H H B24 CF.sub.3 Cl Me2-pyridyl H H B25 CF.sub.3 Cl Me2-pyridyl H H B26 CF.sub.3 Cl Me2-pyridyl H H B27 CF.sub.3 Cl Me2-pyridyl H H B28 CF.sub.3 Cl Me2-pyridyl H H B29 CF.sub.3 Cl Me2-pyridyl H H B30 CF.sub.3 Cl Me2-pyridyl H H B31 CF.sub.3 Cl Me2-pyridyl H H B32 CF.sub.3 Cl Me2-pyridyl H H B33 CF.sub.3 Cl Me2-pyridyl H H B34 CF.sub.3 Cl Me2-pyridyl H H Na CF.sub.3 Cl Me2-pyridyl H H K CF.sub.3 Cl Me2-pyridyl H H B1 Cl H H2-pyridyl H H B2 Cl H H2-pyridyl H H B3 Cl H H2-pyridyl H H B4 Cl H H2-pyridyl Me H B4 Cl H H2-pyridyl Cl H B4 Cl H H2-pyridyl NO.sub.2 H B4 Cl H H2-pyridyl CO.sub.2 Me H B4 Cl H H2-pyridyl CO.sub.2 Et H B4 Cl H H2-pyridyl H H B5 Cl H H2-pyridyl H H B6 Cl H H2-pyridyl NO.sub.2 H B6 Cl H H2-pyridyl H H B7 Cl H H2-pyridyl Me H B7 Cl H H2-pyridyl Cl H B7 Cl H H2-pyridyl NO.sub.2 H B7 Cl H H2-pyridyl CO.sub.2 Me H B7 Cl H H2-pyridyl CO.sub.2 Et H B7 Cl H H2-pyridyl H H B8 Cl H H2-pyridyl H H B9 Cl H H2-pyridyl H H B10 Cl H H2-pyridyl H H B11 Cl H H2-pyridyl H H B12 Cl H H2-pyridyl H H B13 Cl H H2-pyridyl H H B14 Cl H H2-pyridyl H H B15 Cl H H2-pyridyl H H B16 Cl H H2-pyridyl H H B17 Cl H H2-pyridyl H H B18 Cl H H2-pyridyl H H B19 Cl H H2-pyridyl H H B20 Cl H H2-pyridyl H H B21 Cl H H2-pyridyl H H B22 Cl H H2-pyridyl H H B23 Cl H H2-pyridyl H H B24 Cl H H2-pyridyl H H B25 Cl H H2-pyridyl H H B26 Cl H H2-pyridyl H H B27 Cl H H2-pyridyl H H B28 Cl H H2-pyridyl H H B29 Cl H H2-pyridyl H H B30 Cl H H2-pyridyl H H B31 Cl H H2-pyridyl H H B32 Cl H H2-pyridyl H H B33 Cl H H2-pyridyl H H B34 Cl H H2-pyridyl H H Na Cl H H2-pyridyl H H K Cl H H3-pyridyl H H H Cl Cl Me3-pyridyl H H H CF.sub.3 Cl Me3-pyridyl H H H Cl H H3-pyridyl H H B4 Cl H H3-pyridyl H H B7 Cl H H4-pyridyl H H H Cl Cl Me4-pyridyl H H H CF.sub.3 Cl Me4-pyridyl H H H Cl H H4-pyridyl H H B4 Cl H H4-pyridyl H H B7 Cl H H3-Me-pyridin- H H H Cl Cl Me2-yl2-F--Ph H H H Me H Me2-F--Ph H H H Me Me Me2-F--Ph H H H Me Cl Me2-F--Ph H H H Cl H H2-F--Ph H H H Cl H Me2-F--Ph H H H Cl H CF.sub.32-F--Ph H H H Cl Cl Me2-F--Ph Cl H H Cl Cl Me2-F--Ph H H B7 OMe H H2-F--Ph H H B7 SMe H H2-F--Ph H H H CF.sub.3 Me Me2-F--Ph H H H CF.sub.3 Cl Me2-F--Ph Cl H H CF.sub.3 Cl Me2-F--Ph H H H CF.sub.3 H Me2-F--Ph H H B1 Cl Cl Me2-F--Ph Cl H B1 Cl Cl Me2-F--Ph H H B3 Cl Cl Me2-F--Ph Cl H B4 Cl Cl Me2-F--Ph H H B6 Cl Cl Me2-F--Ph H H B7 Cl Cl Me2-F--Ph Cl H B7 Cl Cl Me2-F--Ph H H B9 Cl Cl Me2-F--Ph H H B20 Cl Cl Me2-F--Ph H H B24 Cl Cl Me2-F--Ph H H B2 CF.sub.3 Cl Me2-F--Ph H H B3 CF.sub.3 Cl Me2-F--Ph H H B4 CF.sub.3 Cl Me2-F--Ph Cl H B4 CF.sub.3 Cl Me2-F--Ph H H B6 CF.sub.3 Cl Me2-F--Ph H H B7 CF.sub.3 Cl Me2-F--Ph Cl H B7 CF.sub.3 Cl Me2-F--Ph H H B9 CF.sub.3 Cl Me2-F--Ph H H B20 CF.sub.3 Cl Me2-F--Ph H H B24 CF.sub.3 Cl Me2-F--Ph H H B6 Cl H H2-F--Ph H H B7 Cl H H3-F--Ph H H H Cl Cl Me3-F--Ph Cl H H Cl Cl Me3-F--Ph H H H CF.sub.3 Cl Me3-F--Ph Cl H H CF.sub.3 Cl Me4-F--Ph H H H Cl Cl Me4-F--Ph Cl H H Cl Cl Me4-F--Ph H H H CF.sub.3 Cl Me4-F--Ph Cl H H CF.sub.3 Cl Me2,3-F.sub.2 --Ph H H H Cl Cl Me2,3-F.sub.2 --Ph H H H CF.sub.3 Cl Me2,4-F.sub.2 --Ph H H H Cl Cl Me2,4-F.sub.2 --Ph H H H CF.sub.3 Cl Me2,5-F.sub.2 --Ph H H H Cl Cl Me2,5-F.sub.2 --Ph H H H CF.sub.3 Cl MePh H H H Me H MePh H H H Me Me MePh H H H Me Cl MePh H H B7 Cl H HPh H H H Cl H MePh H H H Cl H CF.sub.3Ph H H H Cl Cl MePh Cl H H Cl Cl MePh H H B7 OMe H HPh H H B7 SMe H HPh H H H CF.sub.3 Me MePh H H H CF.sub.3 Cl MePh Cl H H CF.sub.3 Cl MePh H H B7 CF.sub.3 H MePh H H B1 Cl Cl MePh Cl H B1 Cl Cl MePh H H B3 Cl Cl MePh Cl H B4 Cl Cl MePh H H B6 Cl Cl MePh H H B7 Cl Cl MePh Cl H B7 Cl Cl MePh H H B9 Cl Cl MePh H H B20 Cl Cl MePh H H B24 Cl Cl MePh H H B2 CF.sub.3 Cl MePh H H B3 CF.sub.3 Cl MePh H H B4 CF.sub.3 Cl MePh Cl H B4 CF.sub.3 Cl MePh H H B6 CF.sub.3 Cl MePh H H B7 CF.sub.3 Cl MePh Cl H B7 CF.sub.3 Cl MePh H H B9 CF.sub.3 Cl MePh H H B20 CF.sub.3 Cl MePh H H B24 CF.sub.3 Cl MePh H H B6 Cl H HPh H H B7 Cl H H3,4-F.sub.2 --Ph H H H Cl Cl Me3,4-F.sub.2 --Ph H H H CF.sub.3 Cl Me3,5-F.sub.2 --Ph H H H Cl Cl Me3,5-F.sub.2 --Ph H H H CF.sub.3 Cl Me2-Cl--Ph H H H Me H Me2-Cl--Ph H H H Me Me Me2-Cl--Ph H H H Me Cl Me2-Cl--Ph H H H Cl H H2-Cl--Ph H H H Cl H Me2-Cl--Ph H H H Cl H CF.sub.32-Cl--Ph H H H Cl Cl Me2-Cl--Ph Cl H H Cl Cl Me2-Cl--Ph H H H OMe H H2-Cl--Ph H H H SMe H H2-Cl--Ph H H H CF.sub.3 Me Me2-Cl--Ph H H H CF.sub.3 Cl Me2-Cl--Ph Cl H H CF.sub.3 Cl Me2-Cl--Ph H H H CF.sub.3 H Me2-Cl--Ph H H H Cl Cl Me2-Cl--Ph Cl H B1 Cl Cl Me2-Cl--Ph H H B3 Cl Cl Me2-Cl--Ph Cl H B4 Cl Cl Me2-Cl--Ph H H B6 Cl Cl Me2-Cl--Ph H H B7 Cl Cl Me2-Cl--Ph Cl H B7 Cl Cl Me2-Cl--Ph H H B9 Cl Cl Me2-Cl--Ph H H B20 Cl Cl Me2-Cl--Ph H H B24 Cl Cl Me2-Cl--Ph H H B2 CF.sub.3 Cl Me2-Cl--Ph H H B3 CF.sub.3 Cl Me2-Cl--Ph H H B4 CF.sub.3 Cl Me2-Cl--Ph Cl H B4 CF.sub.3 Cl Me2-Cl--Ph H H B6 CF.sub.3 Cl Me2-Cl--Ph H H B7 CF.sub.3 Cl Me2-Cl--Ph Cl H B7 CF.sub.3 Cl Me2-Cl--Ph H H B9 CF.sub.3 Cl Me2-Cl--Ph H H B20 CF.sub.3 Cl Me2-Cl--Ph H H B24 CF.sub.3 Cl Me2-Cl--Ph H H B6 Cl H H2-Cl--Ph H H B7 Cl H H3-Cl--Ph H H H Cl Cl Me3-Cl--Ph Cl H H Cl Cl Me3-Cl--Ph H H H CF.sub.3 Cl Me3-Cl--Ph Cl H H CF.sub.3 Cl Me4-Cl--Ph H H H Cl Cl Me4-Cl--Ph Cl H H Cl Cl Me4-Cl--Ph H H H CF.sub.3 Cl Me4-Cl--Ph Cl H H CF.sub.3 Cl Me2,3-Cl.sub.2 --Ph H H H Cl Cl Me2,3-Cl.sub.2 --Ph H H H CF.sub.3 Cl Me2,4-Cl.sub.2 --Ph H H H Cl Cl Me2,4-Cl.sub.2 --Ph H H H CF.sub.3 Cl Me2,5-Cl.sub.2 --Ph H H H Cl Cl Me2,5-Cl.sub.2 --Ph H H H CF.sub.3 Cl Me2,6-Cl.sub.2 --Ph H H H Me H Me2,6-Cl.sub.2 --Ph H H H Me Me Me2,6-Cl.sub.2 --Ph H H H Me Cl Me2,6-Cl.sub.2 --Ph H H B7 Cl H H2,6-Cl.sub.2 --Ph H H H Cl H Me2,6-Cl.sub.2 --Ph H H H Cl H CF.sub.32,6-Cl.sub.2 --Ph H H H Cl Cl Me2,6-Cl.sub.2 --Ph Cl H H Cl Cl Me2,6-Cl.sub.2 --Ph H H B7 OMe H H2,6-Cl.sub.2 --Ph H H B7 SMe H H2,6-Cl.sub.2 --Ph H H H CF.sub.3 Me Me2,6-Cl.sub.2 --Ph H H H CF.sub.3 Cl Me2,6-Cl.sub.2 --Ph Cl H H CF.sub.3 Cl Me2,6-Cl.sub.2 --Ph H H H CF.sub.3 H Me2,6-Cl.sub.2 --Ph H H B1 Cl Cl Me2,6-Cl.sub.2 --Ph Cl H B1 Cl Cl Me2,6-Cl.sub.2 --Ph H H B3 Cl Cl Me2,6-Cl.sub.2 --Ph Cl H B4 Cl Cl Me2,6-Cl.sub.2 --Ph H H B6 Cl Cl Me2,6-Cl.sub.2 --Ph H H B7 Cl Cl Me2,6-Cl.sub.2 --Ph Cl H B7 Cl Cl Me2,6-Cl.sub.2 --Ph H H B9 Cl Cl Me2,6-Cl.sub.2 --Ph H H B20 Cl Cl Me2,6-Cl.sub.2 --Ph H H B24 Cl Cl Me2,6-Cl.sub.2 --Ph H H B2 CF.sub.3 Cl Me2,6-Cl.sub.2 --Ph H H B3 CF.sub.3 Cl Me2,6-Cl.sub.2 --Ph H H B4 CF.sub.3 Cl Me2,6-Cl.sub.2 --Ph Cl H B4 CF.sub.3 Cl Me2,6-Cl.sub.2 --Ph H H B6 CF.sub.3 Cl Me2,6-Cl.sub.2 --Ph H H B7 CF.sub.3 Cl Me2,6-Cl.sub.2 --Ph Cl H B7 CF.sub.3 Cl Me2,6-Cl.sub.2 --Ph H H B9 CF.sub.3 Cl Me2,6-Cl.sub.2 --Ph H H B20 CF.sub.3 Cl Me2,6-Cl.sub.2 --Ph H H B24 CF.sub.3 Cl Me2,6-Cl.sub.2 --Ph H H B8 Cl H H2,6-Cl.sub.2 --Ph H H B15 Cl H H3,4-Cl.sub.2 --Ph H H H Cl Cl Me3,4-Cl.sub.2 --Ph H H H CF.sub.3 Cl Me3,5-Cl.sub.2 --Ph H H H Cl Cl Me3,5-Cl.sub.2 --Ph H H H CF.sub.3 Cl Me2-Me--Ph H H H Cl Cl Me2-Me--Ph H H H CF.sub.3 Cl Me2,6-Me.sub.2 --Ph H H H Cl Cl Me2,6-Me.sub.2 --Ph H H H CF.sub.3 Cl Me2-MeO--Ph H H H Cl Cl Me2-MeO--Ph H H H CF.sub.3 Cl Me2-MeO--Ph Cl H H CF.sub.3 Cl Me2-CF.sub.3 O--Ph H H H Cl Cl Me2-CF.sub.3 O--Ph H H H CF.sub.3 Cl Me2-SMe--Ph H H H Cl Cl Me2-SMe--Ph H H H CF.sub.3 Cl Me2-SOMe--Ph H H H Cl Cl Me2-SOMe--Ph H H H CF.sub.3 Cl Me2-SO.sub.2 Me--Ph H H H Cl Cl Me2-SO.sub.2 Me--Ph H H H CF.sub.3 Cl Me2-CF.sub.3 --Ph H H H Cl Cl Me2-CF.sub.3 --Ph H H H CF.sub.3 Cl Me2-NO.sub.2 --Ph H H H Cl Cl Me2-NO.sub.2 --Ph H H H CF.sub.3 Cl Me2-CN--Ph H H H Cl Cl Me2-CN--Ph H H H CF.sub.3 Cl Me2-NHMe--Ph H H H Cl Cl Me2-NHMe--Ph H H H CF.sub.3 Cl Me2-NMe.sub.2 --Ph H H H Cl Cl Me2-NMe.sub.2 --Ph H H H CF.sub.3 Cl Me4-CH.sub.2 Ph--Ph H H H Cl Cl Me4-OPh--Ph H H H Cl Cl Me2-OH--Ph H H H Cl Cl Me2-OH--Ph H H H CF.sub.3 Cl Me2-CO.sub.2 Me--Ph H H H Cl Cl Me2-CO.sub.2 Me--Ph H H H CF.sub.3 Cl Me2-CO.sub.2 Et--Ph H H H Cl Cl Me2-CO.sub.2 Et--Ph H H H CF.sub.3 Cl MeH CO.sub.2 Et Ph H Cl Cl MeCl CO.sub.2 Et H H Cl Cl MeMe Ph H H Cl Cl MeEt Me H H Cl Cl MenPr H H H Cl Cl MeiPr H H H Cl Cl MeiPr H H H CF.sub.3 Cl MenBu H H H Cl Cl MenBu H H H CF.sub.3 Cl MeiBu H H H Cl Cl MeiBu H H H CF.sub.3 Cl MeiBu H H B7 Cl Cl MeiBu H H B7 CF.sub.3 Cl MesecBu H H H Cl Cl MesecBu H H H CF.sub.3 Cl Me2,2-Me.sub.2 -propyl H H H Cl Cl MenHex H H H Cl Cl Meethenyl H H H Cl Cl Me1-propenyl H H H Cl Cl Me1-propenyl H H H CF.sub.3 Cl Meethynyl H H H Cl Cl Me1-propynyl H H H Cl Cl Me1-propynyl H H H CF.sub.3 Cl MeCF.sub.3 H H H Cl Cl MeCF.sub.3 H H H CF.sub.3 Cl MeC.sub.2 F.sub.5 H H H Cl Cl MeC.sub.2 F.sub.5 H H H CF.sub.3 Cl Me2,2-Cl.sub.2 -cPr H H H Cl Cl Me2,2-Cl.sub.2 -cPr H H H CF.sub.3 Cl MecPr H H H Cl Cl MecPr H H H CF.sub.3 Cl Me1-Me-cPr H H H Cl Cl Me1-Me-cPr H H H CF.sub.3 Cl MecHex H H H Cl Cl MecHex H H H CF.sub.3 Cl MeOMe H H H Cl Cl MeOtBu H H H Cl Cl MeOtBu H H H CF.sub.3 Cl MeOCF.sub.3 H H H Cl Cl MeOCF.sub.3 H H H CF.sub.3 Cl MeStBu H H H Cl Cl MeStBu H H H CF.sub.3 Cl MeSOtBu H H H Cl Cl MeSOtBu H H H CF.sub.3 Cl MeSO.sub.2 tBu H H H Cl Cl MeSO.sub.2 tBu H H H CF.sub.3 Cl MeNO.sub.2 H H H Cl Cl MeNO.sub.2 H H H CF.sub.3 Cl MeCN H H H Cl Cl MeCN H H H CF.sub.3 Cl MeNH.sub.2 H H H Cl Cl MeNH.sub.2 H H H CF.sub.3 Cl MeNHMe H H H Cl Cl MeNHMe H H H CF.sub.3 Cl MeNMe.sub.2 H H H Cl Cl MeNMe.sub.2 H H H CF.sub.3 Cl MeCH.sub.2 Ph H H H Cl Cl MeCH.sub.2 Ph H H H CF.sub.3 Cl MeOPh H H H Cl Cl MeOPh H H H CF.sub.3 Cl MeOH H H H Cl Cl MeOH H H H CF.sub.3 Cl Menaphthyl-1 H H H Cl Cl Menaphthyl-1 H H H CF.sub.3 Cl Menaphthyl-2 H H H Cl Cl Menaphthyl-2 H H H CF.sub.3 Cl MeCO.sub.2 Me H H H Cl Cl MeCO.sub.2 Me H H H CF.sub.3 Cl MeCO.sub.2 Et H H H Cl Cl MeCO.sub.2 Et H H H CF.sub.3 Cl Me2-thienyl H H H Cl Cl Me2-thienyl H H H CF.sub.3 Cl MeCH.sub.2 OMe H H H Cl Cl MeCOCH.sub.3 H H H Cl Cl Me--N.dbd.CMe.sub.2 H H H Cl Cl Me--N.dbd.CMe.sub.2 H H H CF.sub.3 Cl Me--(CH.sub.2).sub.3 -- H H Cl Cl Me--(CH.sub.2).sub.3 -- H H CF.sub.3 Cl Me--(CH.sub.2).sub.4 -- H H Cl Cl Me--(CH.sub.2).sub.4 -- H H CF.sub.3 Cl Me______________________________________
TABLE 2______________________________________ ##STR57## ##STR58## ##STR59## ##STR60## ##STR61## ##STR62## ##STR63## ##STR64## ##STR65## ##STR66## ##STR67## ##STR68## ##STR69## ##STR70## ##STR71## ##STR72## ##STR73## ##STR74## ##STR75## ##STR76## ##STR77## ##STR78## ##STR79## ##STR80## ##STR81## ##STR82## ##STR83## ##STR84##R.sup.1 R.sup.2 R.sup.3 B Y.sup.1 Y.sup.2 Y.sup.3______________________________________2,6-F.sub.2 --Ph H H H Me H Me2,6-F.sub.2 --Ph H H H Me H CF.sub.32,6-F.sub.2 --Ph H H H Me H H2,6-F.sub.2 --Ph H H H Me Me Me2,6-F.sub.2 --Ph H H H Me Cl Me2,6-F.sub.2 --Ph Cl H H Me Cl Me2,6-F.sub.2 --Ph H H H Et Me Me2,6-F.sub.2 --Ph H H H Cl Me Me2,6-F.sub.2 --Ph H H H Cl H Me2,6-F.sub.2 --Ph H H H Cl H CF.sub.32,6-F.sub.2 --Ph H H H Cl H H2,6-F.sub.2 --Ph Me H H Cl H H2,6-F.sub.2 --Ph Cl H H Cl H H2,6-F.sub.2 --Ph H H H Cl Cl Me2,6-F.sub.2 --Ph Me H H Cl Cl Me2,6-F.sub.2 --Ph H Cl H Cl Cl Me2,6-F.sub.2 --Ph Cl H H Cl Cl Me2,6-F.sub.2 --Ph CF.sub.3 H H Cl Cl Me2,6-F.sub.2 --Ph OMe H H Cl Cl Me2,6-F.sub.2 --Ph NH.sub.2 H H Cl Cl Me2,6-F.sub.2 --Ph NHMe H H Cl Cl Me2,6-F.sub.2 --Ph NMe.sub.2 H H Cl Cl Me2,6-F.sub.2 --Ph NO.sub.2 H H Cl Cl Me2,6-F.sub.2 --Ph CN H H Cl Cl Me2,6-F.sub.2 --Ph OH H H Cl Cl Me2,6-F.sub.2 --Ph CO.sub.2 Me H H Cl Cl Me2,6-F.sub.2 --Ph CO.sub.2 Et H H Cl Cl Me2,6-F.sub.2 --Ph H H H Cl Cl CF.sub.32,6-F.sub.2 --Ph H H H Cl Cl CF.sub.2 H2,6-F.sub.2 --Ph H H H Cl Cl CH.sub.2 OMe2,6-F.sub.2 --Ph H H H Cl Cl COMe2,6-F.sub.2 --Ph H H H Cl CF.sub.3 Me2,6-F.sub.2 --Ph H H H Br Me Me2,6-F.sub.2 --Ph H H H Me Br Me2,6-F.sub.2 --Ph H H H Me OMe Me2,6-F.sub.2 --Ph H H H OMe H H2,6-F.sub.2 --Ph H H H OCF.sub.3 H H2,6-F.sub.2 --Ph H H H SMe H H2,6-F.sub.2 --Ph H H H CF.sub.3 Me Me2,6-F.sub.2 --Ph H H H CF.sub.3 Cl Me2,6-F.sub.2 --Ph Me H H CF.sub.3 Cl Me2,6-F.sub.2 --Ph Cl H H CF.sub.3 Cl Me2,6-F.sub.2 --Ph Br H H CF.sub.3 Cl Me2,6-F.sub.2 --Ph CF.sub.3 H H CF.sub.3 Cl Me2,6-F.sub.2 --Ph NO.sub.2 H H CF.sub.3 Cl Me2,6-F.sub.2 --Ph CN H H CF.sub.3 Cl Me2,6-F.sub.2 --Ph CO.sub.2 Me H H CF.sub.3 Cl Me2,6-F.sub.2 --Ph CO.sub.2 Et H H CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H H CF.sub.3 Cl CF.sub.32,6-F.sub.2 --Ph H H H CF.sub.3 Cl CF.sub.2 H2,6-F.sub.2 --Ph H H H CF.sub.3 Cl CH.sub.2 OMe2,6-F.sub.2 --Ph H H H CF.sub.3 Cl COCH.sub.32,6-F.sub.2 --Ph H H H CF.sub.3 H Me2,6-F.sub.2 --Ph H H H CF.sub.3 Br Me2,6-F.sub.2 --Ph H H H CF.sub.3 NO.sub.2 Me2,6-F.sub.2 --Ph H H H CF.sub.3 CN Me2,6-F.sub.2 --Ph H H H CF.sub.3 NHMe Me2,6-F.sub.2 --Ph H H H CF.sub.3 NMe.sub.2 Me2,6-F.sub.2 --Ph H H H CF.sub.3 CO.sub.2 Me Me2,6-F.sub.2 --Ph H H H CF.sub.3 OMe Me2,6-F.sub.2 --Ph H H H CF.sub.3 OCF.sub.2 H CF.sub.2 H2,6-F.sub.2 --Ph H H H Cl NO.sub.2 Me2,6-F.sub.2 --Ph H H H Cl CN Me2,6-F.sub.2 --Ph H H H CO.sub.2 Me Me Me2,6-F.sub.2 --Ph H H B1 Cl Cl Me2,6-F.sub.2 --Ph H H B2 Cl Cl Me2,6-F.sub.2 --Ph H H B3 Cl Cl Me2,6-F.sub.2 --Ph H H B4 Cl Cl Me2,6-F.sub.2 --Ph H H B5 Cl Cl Me2,6-F.sub.2 --Ph H H B6 Cl Cl Me2,6-F.sub.2 --Ph H H B7 Cl Cl Me2,6-F.sub.2 --Ph H H B8 Cl Cl Me2,6-F.sub.2 --Ph H H B9 Cl Cl Me2,6-F.sub.2 --Ph H H B10 Cl Cl Me2,6-F.sub.2 --Ph H H B11 Cl Cl Me2,6-F.sub.2 --Ph H H B12 Cl Cl Me2,6-F.sub.2 --Ph H H B13 Cl Cl Me2,6-F.sub.2 --Ph H H B14 Cl Cl Me2,6-F.sub.2 --Ph H H B15 Cl Cl Me2,6-F.sub.2 --Ph H H B16 Cl Cl Me2,6-F.sub.2 --Ph H H B17 Cl Cl Me2,6-F.sub.2 --Ph H H B18 Cl Cl Me2,6-F.sub.2 --Ph H H B19 Cl Cl Me2,6-F.sub.2 --Ph H H B20 Cl Cl Me2,6-F.sub.2 --Ph H H B21 Cl Cl Me2,6-F.sub.2 --Ph H H B22 Cl Cl Me2,6-F.sub.2 --Ph H H B23 Cl Cl Me2,6-F.sub.2 --Ph H H B24 Cl Cl Me2,6-F.sub.2 --Ph H H B25 Cl Cl Me2,6-F.sub.2 --Ph H H B26 Cl Cl Me2,6-F.sub.2 --Ph H H B27 Cl Cl Me2,6-F.sub.2 --Ph H H B28 Cl Cl Me2,6-F.sub.2 --Ph H H B29 Cl Cl Me2,6-F.sub.2 --Ph H H B30 Cl Cl Me2,6-F.sub.2 --Ph H H B31 Cl Cl Me2,6-F.sub.2 --Ph H H B32 Cl Cl Me2,6-F.sub.2 --Ph H H B33 Cl Cl Me2,6-F.sub.2 --Ph H H B34 Cl Cl Me2,6-F.sub.2 --Ph H H Na Cl Cl Me2,6-F.sub.2 --Ph H H K Cl Cl Me2,6-F.sub.2 --Ph H H B2 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B3 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B4 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B5 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B6 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B7 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B8 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B9 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B10 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B11 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B12 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B13 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B14 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B15 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B16 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B17 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B18 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B19 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B20 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B21 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B22 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B23 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B24 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B25 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B26 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B27 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B28 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B29 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B30 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B31 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B32 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B33 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B34 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H Na CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H K CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H B7 Cl H H2,6-F.sub.2 --Ph H H B9 Cl H H2,6-F.sub.2 --Ph H H B10 Cl H H2,6-F.sub.2 --PhPh H H B11 Cl H HtBu H H H Me H MetBu H H H Me H CF.sub.3tBu H H H Me H HtBu H H H Me Me MetBu H H H Me Cl MetBu Cl H H Me Cl MetBu H H H Cl Me MetBu H H H Cl H MetBu H H H Cl H CF.sub.3tBu H H H Cl H HtBu H H H Cl Cl MetBu Me H H Cl Cl MetBu Cl H H Cl Cl MetBu NO.sub.2 H H Cl Cl MetBu CO.sub.2 Me H H Cl Cl MetBu CO.sub.2 Et H H Cl Cl MetBu H H H Cl Cl CF.sub.3tBu H H H Cl Cl CF.sub.2 HtBu H H H Cl Cl CH.sub.2 OMetBu H H H Cl Cl COMetBu H H H Cl CF.sub.3 MetBu H H H Br Me MetBu H H H Me Br MetBu H H H OMe H HtBu H H H CF.sub.3 Me MetBu H H H CF.sub.3 Cl MetBu Me H H CF.sub.3 Cl MetBu Cl H H CF.sub.3 Cl MetBu NO.sub.2 H H CF.sub.3 Cl MetBu CO.sub.2 Me H H CF.sub.3 Cl MetBu CO.sub.2 Et H H CF.sub.3 Cl MetBu H H H CF.sub.3 Cl CF.sub.3tBu H H H CF.sub.3 Cl CF.sub.2 HtBu H H H CF.sub.3 Cl CH.sub.2 OMetBu H H H CF.sub.3 Cl COCH.sub.3tBu H H H CF.sub.3 H MetBu H H H CF.sub.3 NO.sub.2 MetBu H H H CF.sub.3 NHMe MetBu H H H CF.sub.3 NMe.sub.2 MetBu H H H NO.sub.2 Me MetBu H H H CN Cl MetBu H H H CN Me MetBu H H H Cl CN MetBu H H H CO.sub.2 Me Me MetBu H H H CO.sub.2 Me Cl MetBu H H B1 Cl Cl MetBu Cl H B1 Cl Cl MetBu H H B2 Cl Cl MetBu H H B3 Cl Cl MetBu H H B4 Cl Cl MetBu H H B5 Cl Cl MetBu H H B6 Cl Cl MetBu H H B7 Cl Cl MetBu H H B8 Cl Cl MetBu H H B9 Cl Cl MetBu H H B10 Cl Cl MetBu H H B11 Cl Cl MetBu H H B12 Cl Cl MetBu H H B13 Cl Cl MetBu H H B14 Cl Cl MetBu H H B15 Cl Cl MetBu H H B16 Cl Cl MetBu H H B17 Cl Cl MetBu H H B18 Cl Cl MetBu H H B19 Cl Cl MetBu H H B20 Cl Cl MetBu H H B21 Cl Cl MetBu H H B22 Cl Cl MetBu H H B23 Cl Cl MetBu H H B24 Cl Cl MetBu H H B25 Cl Cl MetBu H H B26 Cl Cl MetBu H H B27 Cl Cl MetBu H H B28 Cl Cl MetBu H H B29 Cl Cl MetBu H H B30 Cl Cl MetBu H H B31 Cl Cl MetBu H H B32 Cl Cl MetBu H H B33 Cl Cl MetBu H H B34 Cl Cl MetBu H H Na Cl Cl MetBu H H K Cl Cl MetBu H H B2 CF.sub.3 Cl MetBu H H B3 CF.sub.3 Cl MetBu H H B4 CF.sub.3 Cl MetBu H H B5 CF.sub.3 Cl MetBu H H B6 CF.sub.3 Cl MetBu H H B7 CF.sub.3 Cl MetBu H H B8 CF.sub.3 Cl MetBu H H B9 CF.sub.3 Cl MetBu H H B10 CF.sub.3 Cl MetBu H H B11 CF.sub.3 Cl MetBu H H B12 CF.sub.3 Cl MetBu H H B13 CF.sub.3 Cl MetBu H H B14 CF.sub.3 Cl MetBu H H B15 CF.sub.3 Cl MetBu H H B16 CF.sub.3 Cl MetBu H H B17 CF.sub.3 Cl MetBu H H B18 CF.sub.3 Cl MetBu H H B19 CF.sub.3 Cl MetBu H H B20 CF.sub.3 Cl MetBu H H B21 CF.sub.3 Cl MetBu H H B22 CF.sub.3 Cl MetBu H H B23 CF.sub.3 Cl MetBu H H B24 CF.sub.3 Cl MetBu H H B25 CF.sub.3 Cl MetBu H H B26 CF.sub.3 Cl MetBu H H B27 CF.sub.3 Cl MetBu H H B28 CF.sub.3 Cl MetBu H H B29 CF.sub.3 Cl MetBu H H B30 CF.sub.3 Cl MetBu H H B31 CF.sub.3 Cl MetBu H H B32 CF.sub.3 Cl MetBu H H B33 CF.sub.3 Cl MetBu H H B34 CF.sub.3 Cl MetBu H H Na CF.sub.3 Cl MetBu H H K CF.sub.3 Cl MetBu H H B7 Cl H HtBu H H B8 Cl H HtBu H H B15 Cl H HtBu H H B17 Cl H HtBu H H B18 Cl H HtBu H H B34 Cl H H2-pyridyl H H H Me H Me2-pyridyl H H H Me H CF.sub.32-pyridyl H H B7 Me H H2-pyridyl H H H Me Me Me2-pyridyl H H H Me Cl Me2-pyridyl H H H Cl Me Me2-pyridyl H H H Cl H Me2-pyridyl H H H Cl H CF.sub.32-pyridyl H H H Cl H H2-pyridyl Cl H H Cl H H2-pyridyl CO.sub.2 Me H H Cl H H2-pyridyl CO.sub.2 Et H H Cl H H2-pyridyl H H H Cl Cl Me2-pyridyl H H H Cl CF.sub.3 Me2-pyridyl H H H Br Me Me2-pyridyl H H H Me Br Me2-pyridyl H H B7 OMe H H2-pyridyl H H H CF.sub.3 Me Me2-pyridyl H H H CF.sub.3 Cl Me2-pyridyl H H H CF.sub.3 H Me2-pyridyl H H B7 CF.sub.3 H H2-pyridyl H H B1 Cl Cl Me2-pyridyl H H B3 Cl Cl Me2-pyridyl H H B7 Cl Cl Me2-pyridyl H H B3 CF.sub.3 Cl Me2-pyridyl H H B7 CF.sub.3 Cl Me2-pyridyl H H B3 Cl H H2-pyridyl H H B4 Cl H H2-pyridyl H H B5 Cl H H2-pyridyl H H B6 Cl H H2-pyridyl H H B7 Cl H H2-pyridyl H H B8 Cl H H2-pyridyl H H B9 Cl H H2-pyridyl H H B10 Cl H H2-pyridyl H H B11 Cl H H2-pyridyl H H B15 Cl H H2-pyridyl H H B16 Cl H H2-pyridyl H H B17 Cl H H2-pyridyl H H B28 Cl H H2-pyridyl H H B30 Cl H H2-pyridyl H H B31 Cl H H2-pyridyl H H B32 Cl H H2-pyridyl H H B34 Cl H H3-pyridyl H H H Cl Cl Me3-pyridyl H H H Cl H H4-pyridyl H H H Cl Cl Me4-pyridyl H H H Cl H H2-F--Ph H H H Cl H H2-F--Ph H H H Cl Cl Me2-F--Ph H H B7 OMe H H2-F--Ph H H B7 SMe H H2-F--Ph H H H CF.sub.3 Cl Me2-F--Ph H H H CF.sub.3 H Me2-F--Ph H H B1 Cl Cl Me2-F--Ph H H B3 Cl Cl Me2-F--Ph H H B6 Cl Cl Me2-F--Ph H H B7 Cl Cl Me2-F--Ph Cl H B7 Cl Cl Me2-F--Ph H H B3 CF.sub.3 Cl Me2-F--Ph H H B6 CF.sub.3 Cl Me2-F--Ph H H B7 CF.sub.3 Cl Me2-F--Ph Cl H B7 CF.sub.3 Cl Me2-F--Ph H H B7 Cl H H3-F--Ph H H H Cl Cl Me3-F--Ph H H H CF.sub.3 Cl Me4-F--Ph H H H Cl Cl Me4-F--Ph H H H CF.sub.3 Cl Me2,3-F.sub.2 --Ph H H H Cl Cl Me2,4-F.sub.2 --Ph H H H Cl Cl Me2,5-F.sub.2 --Ph H H H Cl Cl MePh H H H Cl H HPh H H H Cl Cl MePh H H H OMe H HPh H H H SMe H HPh H H H CF.sub.3 Cl MePh H H H CF.sub.3 H MePh H H B1 Cl Cl MePh H H B3 Cl Cl MePh H H B6 Cl Cl MePh H H B7 Cl Cl MePh Cl H B7 Cl Cl MePh H H B3 CF.sub.3 Cl MePh H H B6 CF.sub.3 Cl MePh H H B7 CF.sub.3 Cl MePh Cl H B7 CF.sub.3 Cl MePh H H B7 Cl H HPh H H H Cl Cl MePh H H H Cl Cl Me2-Cl--Ph H H H Cl H H2-Cl--Ph H H H Cl Cl Me2-Cl--Ph H H H OMe H H2-Cl--Ph H H H SMe H H2-Cl--Ph H H H CF.sub.3 Cl Me2-Cl--Ph H H H CF.sub.3 H Me2-Cl--Ph H H B1 Cl Cl Me2-Cl--Ph H H B3 Cl Cl Me2-Cl--Ph H H B6 Cl Cl Me2-Cl--Ph H H B7 Cl Cl Me2-Cl--Ph Cl H B7 Cl Cl Me2-Cl--Ph H H B3 CF.sub.3 Cl Me2-Cl--Ph H H B6 CF.sub.3 Cl Me2-Cl--Ph H H B7 CF.sub.3 Cl Me2-Cl--Ph Cl H B7 CF.sub.3 Cl Me2-Cl--Ph H H B7 Cl H H3-Cl--Ph H H H Cl Cl Me4-Cl--Ph H H H Cl Cl Me2,3-Cl.sub.2 --Ph H H H Cl Cl Me2,4-Cl.sub.2 --Ph H H H Cl Cl Me2,5-Cl.sub.2 --Ph H H H Cl Cl Me2,6-Cl.sub.2 --Ph H H H Cl H H2,6-Cl.sub.2 --Ph H H H Cl Cl Me2,6-Cl.sub.2 --Ph H H H OMe H H2,6-Cl.sub.2 --Ph H H H SMe H H2,6-Cl.sub.2 --Ph H H H CF.sub.3 Cl Me2,6-Cl.sub.2 --Ph H H H CF.sub.3 H Me2,6-Cl.sub.2 --Ph H H B1 Cl Cl Me2,6-Cl.sub.2 --Ph H H B3 Cl Cl Me2,6-Cl.sub.2 --Ph H H B6 Cl Cl Me2,6-Cl.sub.2 --Ph H H B7 Cl Cl Me2,6-Cl.sub.2 --Ph Cl H B7 Cl Cl Me2,6-Cl.sub.2 --Ph H H B3 CF.sub.3 Cl Me2,6-Cl.sub.2 --Ph H H B6 CF.sub.3 Cl Me2,6-Cl.sub.2 --Ph H H B7 CF.sub.3 Cl Me2,6-Cl.sub.2 --Ph Cl H B7 CF.sub.3 Cl Me2,6-Cl.sub.2 --Ph H H B7 Cl H H3,4-Cl.sub.2 --Ph H H H Cl Cl Me3,5-Cl.sub.2 --Ph H H H Cl Cl Me2-Me--Ph H H H Cl Cl Me2-Me--Ph H H H CF.sub.3 Cl Me2,6-Me.sub.2 --Ph H H H Cl Cl Me2,6-Me.sub.2 --Ph H H H CF.sub.3 Cl Me2-MeO--Ph H H H Cl Cl Me2-MeO--Ph H H H CF.sub.3 Cl Me2-CF.sub.3 O--Ph H H H Cl Cl Me2-SMe--Ph H H H Cl Cl Me2-SOMe--Ph H H H Cl Cl Me2-SO.sub.2 Me--Ph H H H Cl Cl Me2-CF.sub.3 --Ph H H H Cl Cl Me2-NO.sub.2 --Ph H H H Cl Cl Me2-CN--Ph H H H Cl Cl Me2-NHMe--Ph H H H Cl Cl Me2-NMe.sub.2 --Ph H H H Cl Cl Me4-benzyl-Ph H H H Cl Cl Me4-phenoxy-Ph H H H Cl Cl Me2-OH--Ph H H H Cl Cl Me2-CO.sub.2 Me--Ph H H H Cl Cl Me2-CO.sub.2 Et--Ph H H H Cl Cl MeH CO.sub.2 Et Ph H Cl Cl MeMe Ph H H Cl Cl MeEt Me H H Cl Cl MenPr H H H Cl Cl MeiPr H H H Cl Cl MeiPr H H H CF.sub.3 Cl MenBu H H H Cl Cl MenBu H H H CF.sub.3 Cl MeiBu H H H Cl Cl MeiBu H H H CF.sub.3 Cl MeiBu H H B7 Cl Cl MeiBu H H B7 CF.sub.3 Cl MeiBu H H H Cl H HsecBu H H H Cl Cl MesecBu H H H CF.sub.3 Cl Me2,2-Me.sub.2 -propyl H H H Cl Cl MenHex H H H Cl Cl Meethenyl H H H Cl Cl Me1-propenyl H H H Cl Cl Me1-propenyl H H H CF.sub.3 Cl Meethynyl H H H Cl Cl Me1-propynyl H H H Cl Cl MeCF.sub.3 H H H Cl Cl MeCHF.sub.2 H H H Cl Cl MeC.sub.2 F.sub.5 H H H Cl Cl Me2,2-Cl.sub.2 -cPr H H H Cl Cl Me2,2-Cl.sub.2 -cPr H H H CF.sub.3 Cl MecPr H H H Cl Cl MecPr H H H CF.sub.3 Cl Me1-Me-cPr H H H Cl Cl Me1-Me-cPr H H H CF.sub.3 Cl MecHex H H H Cl Cl MecHex H H H CF.sub.3 Cl MeCH.sub.2 Ph H H H Cl Cl Menaphthyl-1 H H H Cl Cl Menaphthyl-1 H H H CF.sub.3 Cl Menaphthyl-2 H H H Cl Cl MeCO.sub.2 Me H H H Cl Cl MeCO.sub.2 Et H H H Cl Cl Me2-thienyl H H H Cl Cl MeCH.sub.2 OMe H H H Cl Cl MeCH.sub.2 OEt H H H Cl Cl MeCOCH.sub.3 H H H Cl Cl MeCOtBu H H H Cl Cl Me______________________________________
TABLE 3______________________________________ ##STR85## ##STR86## ##STR87## ##STR88## ##STR89## ##STR90## ##STR91## ##STR92## ##STR93## ##STR94## ##STR95## ##STR96## ##STR97## ##STR98## ##STR99## ##STR100## ##STR101## ##STR102## ##STR103## ##STR104## ##STR105## ##STR106## ##STR107## ##STR108## ##STR109## ##STR110## ##STR111## ##STR112##R.sup.1 R.sup.2 R.sup.3 B Y.sup.1 Y.sup.2______________________________________2,6-F.sub.2 --Ph H H H Me Me2,6-F.sub.2 --Ph H H H Et Me2,6-F.sub.2 --Ph Me H H Et Me2,6-F.sub.2 --Ph Cl H H Et Me2,6-F.sub.2 --Ph H Cl H Et Me2,6-F.sub.2 --Ph H H H Cl Cl2,6-F.sub.2 --Ph H H H Cl Me2,6-F.sub.2 --Ph H H H Cl CF.sub.32,6-F.sub.2 --Ph H H H Me Cl2,6-F.sub.2 --Ph H H H Br Me2,6-F.sub.2 --Ph H H H Me Br2,6-F.sub.2 --Ph H H H Me CF.sub.32,6-F.sub.2 --Ph H H H OMe Me2,6-F.sub.2 --Ph H H H OCF.sub.3 Me2,6-F.sub.2 --Ph H H H SMe Me2,6-F.sub.2 --Ph H H H CO.sub.2 Me Me2,6-F.sub.2 --Ph H H H CO.sub.2 Et Me2,6-F.sub.2 --Ph H H H CF.sub.3 Me2,6-F.sub.2 --Ph H H H CF.sub.3 H2,6-F.sub.2 --Ph H H B3 CF.sub.3 Me2,6-F.sub.2 --Ph H H B6 CF.sub.3 Me2,6-F.sub.2 --Ph H H B7 CF.sub.3 Me2,6-F.sub.2 --Ph Cl H B7 CF.sub.3 MetBu H H H Me MetBu H H H Et MetBu H H H Cl CltBu H H H Cl MetBu H H H Me CltBu H H H Cl CF.sub.3tBu H H H Br MetBu H H H Me BrtBu H H H Me CF.sub.3tBu H H H OMe MetBu H H H OCF.sub.3 MetBu H H H SMe MetBu H H H CO.sub.2 Me MetBu H H H CO.sub.2 Et MetBu H H H CF.sub.3 MetBu Me H H CF.sub.3 MetBu Cl H H CF.sub.3 MetBu Br H H CF.sub.3 MetBu CF.sub.3 H H CF.sub.3 MetBu NO.sub.2 H H CF.sub.3 MetBu CN H H CF.sub.3 MetBu CO.sub.2 Me H H CF.sub.3 MetBu CO.sub.2 Et H H CF.sub.3 MetBu H H H CF.sub.3 HtBu H H H CF.sub.3 BrtBu H H H CF.sub.3 NO.sub.2tBu H H H CF.sub.3 CNtBu H H H CF.sub.3 NHMetBu H H H CF.sub.3 NMe.sub.2tBu H H H CF.sub.3 CO.sub.2 MetBu H H B2 CF.sub.3 MetBu H H B3 CF.sub.3 MetBu H H B4 CF.sub.3 MetBu H H B5 CF.sub.3 MetBu H H B6 CF.sub.3 MetBu H H B7 CF.sub.3 MetBu Cl H B7 CF.sub.3 MetBu H H B8 CF.sub.3 MetBu H H B9 CF.sub.3 MetBu H H B10 CF.sub.3 MetBu H H B11 CF.sub.3 MetBu H H B12 CF.sub.3 MetBu H H B13 CF.sub.3 MetBu H H B14 CF.sub.3 MetBu H H B15 CF.sub.3 MetBu H H B16 CF.sub.3 MetBu H H B17 CF.sub.3 MetBu H H B18 CF.sub.3 MetBu H H B19 CF.sub.3 MetBu H H B20 CF.sub.3 MetBu H H B21 CF.sub.3 MetBu H H B22 CF.sub.3 MetBu H H B23 CF.sub.3 MetBu H H B24 CF.sub.3 MetBu H H B25 CF.sub.3 MetBu H H B26 CF.sub.3 MetBu H H B27 CF.sub.3 MetBu H H B28 CF.sub.3 MetBu H H B29 CF.sub.3 MetBu H H B30 CF.sub.3 MetBu H H B31 CF.sub.3 MetBu H H B32 CF.sub.3 MetBu H H B33 CF.sub.3 MetBu H H B34 CF.sub.3 MetBu H H Na CF.sub.3 MetBu H H K CF.sub.3 Me2-pyridyl H H H Me Me2-pyridyl H H H Et Me2-pyridyl H H H Cl Cl2-pyridyl H H H Cl Me2-pyridyl H H H Cl CF.sub.32-pyridyl H H H Me Cl2-pyridyl H H H Br Me2-pyridyl H H H Me Br2-pyridyl H H H Me CF.sub.32-pyridyl H H H OMe Me2-pyridyl H H H OCF.sub.3 Me2-pyridyl H H H SMe Me2-pyridyl H H H CO.sub.2 Me Me2-pyridyl H H H CO.sub.2 Et Me2-pyridyl H H H CF.sub.3 Me2-pyridyl H H H CF.sub.3 H2-pyridyl H H B3 CF.sub.3 Me2-pyridyl H H B6 CF.sub.3 Me2-pyridyl H H B7 CF.sub.3 Me3-pyridyl H H H CF.sub.3 Me4-pyridyl H H H CF.sub.3 Me2-F--Ph H H H Me Me2-F--Ph H H H Et Me2-F--Ph H H H CF.sub.3 Me2-F--Ph H H H CF.sub.3 Cl2-F--Ph H H H CF.sub.3 H2-F--Ph H H B3 CF.sub.3 Me2-F--Ph H H B6 CF.sub.3 Me2-F--Ph H H B7 CF.sub.3 Me3-F--Ph H H H CF.sub.3 Me4-F--Ph H H H CF.sub.3 Me2,3-F.sub.2 --Ph H H H CF.sub.3 Me2,4-F.sub.2 --Ph H H H CF.sub.3 Me2,5-F.sub.2 --Ph H H H CF.sub.3 MePh H H H Me MePh H H H Et MePh H H H CF.sub.3 MePh H H H CF.sub.3 ClPh H H H CF.sub.3 HPh H H B3 CF.sub.3 MePh H H B6 CF.sub.3 MePh H H B7 CF.sub.3 Me3,4-F.sub.2 --Ph H H H CF.sub.3 Me3,5-F.sub.2 --Ph H H H CF.sub.3 Me2-Cl--Ph H H H Me Me2-Cl--Ph H H H Et Me2-Cl--Ph H H H CF.sub.3 Me2-Cl--Ph H H H CF.sub.3 Cl2-Cl--Ph H H H CF.sub.3 H2-Cl--Ph H H B3 CF.sub.3 Me2-Cl--Ph H H B6 CF.sub.3 Me2-Cl--Ph H H B7 CF.sub.3 Me3-Cl--Ph H H H CF.sub.3 Me4-Cl--Ph H H H CF.sub.3 Me2,3-Cl.sub.2 --Ph H H H CF.sub.3 Me2,4-Cl.sub.2 --Ph H H H CF.sub.3 Me2,5-Cl.sub.2 --Ph H H H CF.sub.3 Me2,6-Cl.sub.2 --Ph H H H Me Me2,6-Cl.sub.2 --Ph H H H Et Me2,6-Cl.sub.2 --Ph H H H CF.sub.3 Me2,6-Cl.sub.2 --Ph H H H CF.sub.3 Cl2,6-Cl.sub.2 --Ph H H H CF.sub.3 H2,6-Cl.sub.2 --Ph H H B3 CF.sub.3 Me2,6-Cl.sub.2 --Ph H H B6 CF.sub.3 Me2,6-Cl.sub.2 --Ph H H B7 CF.sub.3 Me3,4-Cl.sub.2 --Ph H H H CF.sub.3 Me3,5-Cl.sub.2 --Ph H H H CF.sub.3 Me2-Me--Ph H H H CF.sub.3 Me2,6-Me.sub.2 --Ph H H H CF.sub.3 Me2-MeO--Ph H H H CF.sub.3 Me2-CF.sub.3 O--Ph H H H CF.sub.3 Me2-SMe--Ph H H H CF.sub.3 Me2-SOMe--Ph H H H CF.sub.3 Me2-SO.sub.2 Me--Ph H H H CF.sub.3 Me2-CF.sub.3 --Ph H H H CF.sub.3 Me2-NO.sub.2 --Ph H H H CF.sub.3 Me2-CN--Ph H H H CF.sub.3 Me2-NHMe--Ph H H H CF.sub.3 Me2-NMe.sub.2 --Ph H H H CF.sub.3 Me4-benzyl-Ph H H H Et Me4-phenoxy-Ph H H H CF.sub.3 Me2-OH--Ph H H H CF.sub.3 Me2-CO.sub.2 Me--Ph H H H CF.sub.3 Me2-CO.sub.2 Et--Ph H H H CF.sub.3 MeH CO.sub.2 Et Ph H CF.sub.3 MeMe Ph H H CF.sub.3 MeEt Me H H CF.sub.3 MenPr H H H CF.sub.3 MeiPr H H H Et MeiPr H H H CF.sub.3 MenBu H H H Et MenBu H H H CF.sub.3 MeiBu H H H Et MeiBu H H H CF.sub.3 MeiBu H H B7 Et MeiBu H H B7 CF.sub.3 MesecBu H H H Et MesecBu H H H CF.sub.3 Me2,2-Me.sub.2 -propyl H H H CF.sub.3 MenHex H H H CF.sub.3 Meethenyl H H H CF.sub.3 Me1-propenyl H H H CF.sub.3 Meethynyl H H H CF.sub.3 Me1-propynyl H H H CF.sub.3 MeCF.sub.3 H H H CF.sub.3 MeCHF.sub.2 H H H CF.sub.3 MeC.sub.2 F.sub.5 H H H CF.sub.3 Me2,2-Cl.sub.2 -cPr H H H Et Me2,2-Cl.sub.2 -cPr H H H CF.sub.3 MecPr H H H Et MecPr H H H CF.sub.3 Me1-Me-cPr H H H Et Me1-Me-cPr H H H CF.sub.3 MecHex H H H Et MecHex H H H CF.sub.3 MeCH.sub.2 Ph H H H CF.sub.3 Menaphthyl-1 H H H Et Menaphthyl-1 H H H CF.sub.3 Menaphthyl-2 H H H CF.sub.3 MeCO.sub.2 Me H H H CF.sub.3 MeCO.sub.2 Et H H H CF.sub.3 Me2-thienyl H H H CF.sub.3 MeCH.sub.2 OMe H H H CF.sub.3 MeCH.sub.2 OEt H H H CF.sub.3 MeCOCH.sub.3 H H H CF.sub.3 MeCOtBu H H H CF.sub.3 MeCOPh H H H CF.sub.3 Me______________________________________
TABLE 4______________________________________ ##STR113## ##STR114## ##STR115## ##STR116## ##STR117## ##STR118## ##STR119## ##STR120## ##STR121## ##STR122## ##STR123## ##STR124## ##STR125## ##STR126## ##STR127## ##STR128## ##STR129## ##STR130## ##STR131## ##STR132## ##STR133## ##STR134## ##STR135## ##STR136## ##STR137## ##STR138## ##STR139## ##STR140## ##STR141## ##STR142## ##STR143## ##STR144## ##STR145## ##STR146## ##STR147## ##STR148## ##STR149## ##STR150## ##STR151## ##STR152## ##STR153## ##STR154## ##STR155## ##STR156## ##STR157## ##STR158## ##STR159## ##STR160## ##STR161## ##STR162## ##STR163## ##STR164## ##STR165## ##STR166## ##STR167## ##STR168##R.sup.1 R.sup.2 B Y.sup.1 Y.sup.2 Y.sup.3______________________________________2,6-F.sub.2 --Ph H H H CF.sub.3 Me2,6-F.sub.2 --Ph H H Me H Me2,6-F.sub.2 --Ph H H Me H CF.sub.32,6-F.sub.2 --Ph H B7 Me H H2,6-F.sub.2 --Ph H H Me Me Me2,6-F.sub.2 --Ph H H Me Cl Me2,6-F.sub.2 --Ph H H Me Br Me2,6-F.sub.2 --Ph H H Et Me Me2,6-F.sub.2 --Ph H H Cl Me Me2,6-F.sub.2 --Ph H H Cl H Me2,6-F.sub.2 --Ph H H Cl H CF.sub.32,6-F.sub.2 --Ph H H Cl H H2,6-F.sub.2 --Ph H H Cl Cl Me2,6-F.sub.2 --Ph H H Cl Cl CF.sub.32,6-F.sub.2 --Ph H H Cl Cl CF.sub.2 H2,6-F.sub.2 --Ph H H Cl Cl CH.sub.2 OMe2,6-F.sub.2 --Ph H H Cl Cl COMe2,6-F.sub.2 --Ph H H Cl CF.sub.3 Me2,6-F.sub.2 --Ph H H Br Me Me2,6-F.sub.2 --Ph H H Me OMe Me2,6-F.sub.2 --Ph H B7 OMe H H2,6-F.sub.2 --Ph H B7 OCF.sub.3 H H2,6-F.sub.2 --Ph H B7 SMe H H2,6-F.sub.2 --Ph H H CF.sub.3 Me Me2,6-F.sub.2 --Ph H H CF.sub.3 Cl Me2,6-F.sub.2 --Ph H H CF.sub.3 Cl CF.sub.32,6-F.sub.2 --Ph H H CF.sub.3 Cl CF.sub.2 H2,6-F.sub.2 --Ph H H CF.sub.3 Cl CH.sub.2 OMe2,6-F.sub.2 --Ph H H CF.sub.3 H Me2,6-F.sub.2 --Ph H H CF.sub.3 Br Me2,6-F.sub.2 --Ph H H CF.sub.3 NO.sub.2 Me2,6-F.sub.2 --Ph H H CF.sub.3 CN Me2,6-F.sub.2 --Ph H H CF.sub.3 NHMe Me2,6-F.sub.2 --Ph H H CF.sub.3 NMe.sub.2 Me2,6-F.sub.2 --Ph H H CF.sub.3 CO.sub.2 Me Me2,6-F.sub.2 --Ph H H CF.sub.3 OMe Me2,6-F.sub.2 --Ph H H CF.sub.3 OCF.sub.2 H CF.sub.2 H2,6-F.sub.2 --Ph H H Cl NO.sub.2 Me2,6-F.sub.2 --Ph H H Cl CN Me2,6-F.sub.2 --Ph H H CO.sub.2 Me Me Me2,6-F.sub.2 --Ph H B1 Cl Cl Me2,6-F.sub.2 --Ph H B3 Cl Cl Me2,6-F.sub.2 --Ph H B6 Cl Cl Me2,6-F.sub.2 --Ph H B7 Cl Cl Me2,6-F.sub.2 --Ph H B2 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B3 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B4 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B5 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B6 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B7 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B8 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B9 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B10 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B11 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B12 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B13 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B14 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B15 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B16 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B17 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B18 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B19 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B20 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B21 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B22 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B23 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B24 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B25 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B26 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B27 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B28 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B29 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B30 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B31 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B32 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B33 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B34 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H Na CF.sub.3 Cl Me2,6-F.sub.2 --Ph H K CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B7 Cl H H2,6-F.sub.2 --Ph H B9 Cl H H2,6-F.sub.2 --Ph H B10 Cl H H2,6-F.sub.2 --Ph H B11 Cl H HtBu H H H CF.sub.3 MetBu H H Me H MetBu H H Me H CF.sub.3tBu H B7 Me H HtBu H H Me Me MetBu H H Me Cl MetBu H H Me Br MetBu H H Et Me MetBu H H Cl Me MetBu H H Cl H MetBu H H Cl H CF.sub.3tBu H H Cl H HtBu Me H Cl H HtBu Cl H Cl H HtBu H H Cl Cl MetBu H H Cl Cl CF.sub.3tBu H H Cl Cl CF.sub.2 HtBu H H Cl Cl CH.sub.2 OMetBu H H Cl Cl COMetBu H H Cl CF.sub.3 MetBu H H Br Me MetBu H H Me OMe MetBu H B7 OMe H HtBu H B7 OCF.sub.3 H HtBu H B7 SMe H HtBu H H CF.sub.3 Me MetBu H H CF.sub.3 Cl MetBu Br H CF.sub.3 Cl MetBu CF.sub.3 H CF.sub.3 Cl MetBu NO.sub.2 H CF.sub.3 Cl MetBu CN H CF.sub.3 Cl MetBu CO.sub.2 Me H CF.sub.3 Cl MetBu CO.sub.2 Et H CF.sub.3 Cl MetBu H H CF.sub.3 Cl CF.sub.3tBu H H CF.sub.3 Cl CF.sub.2 HtBu H H CF.sub.3 Cl CH.sub.2 OMetBu H H CF.sub.3 H MetBu H H CF.sub.3 Br MetBu H H CF.sub.3 NO.sub.2 MetBu H H CF.sub.3 CN MetBu H H CF.sub.3 NHMe MetBu H H CF.sub.3 NMe.sub.2 MetBu H H CF.sub.3 CO.sub.2 Me MetBu H H CF.sub.3 OMe MetBu H H CF.sub.3 OCF.sub.2 H CF.sub.2 HtBu H H Cl NO.sub.2 MetBu H H Cl CN MetBu H H CO.sub.2 Me Me MetBu H B1 Cl Cl MetBu H B2 Cl Cl MetBu H B3 Cl Cl MetBu H B4 Cl Cl MetBu H B5 Cl Cl MetBu H B6 Cl Cl MetBu H B7 Cl Cl MetBu H B8 Cl Cl MetBu H B9 Cl Cl MetBu H B10 Cl Cl MetBu H B11 Cl Cl MetBu H B12 Cl Cl MetBu H B13 Cl Cl MetBu H B14 Cl Cl MetBu H B15 Cl Cl MetBu H B16 Cl Cl MetBu H B17 Cl Cl MetBu H B18 Cl Cl MetBu H B19 Cl Cl MetBu H B20 Cl Cl MetBu H B21 Cl Cl MetBu H B22 Cl Cl MetBu H B23 Cl Cl MetBu H B24 Cl Cl MetBu H B25 Cl Cl MetBu H B26 Cl Cl MetBu H B27 Cl Cl MetBu H B28 Cl Cl MetBu H B29 Cl Cl MetBu H B30 Cl Cl MetBu H B31 Cl Cl MetBu H B32 Cl Cl MetBu H B33 Cl Cl MetBu H B34 Cl Cl MetBu H Na Cl Cl MetBu H K Cl Cl MetBu H B2 CF.sub.3 Cl MetBu H B3 CF.sub.3 Cl MetBu H B4 CF.sub.3 Cl MetBu H B5 CF.sub.3 Cl MetBu H B6 CF.sub.3 Cl MetBu H B7 CF.sub.3 Cl MetBu H B8 CF.sub.3 Cl MetBu H B9 CF.sub.3 Cl MetBu H B10 CF.sub.3 Cl MetBu H B11 CF.sub.3 Cl MetBu H B12 CF.sub.3 Cl MetBu H B13 CF.sub.3 Cl MetBu H B14 CF.sub.3 Cl MetBu H B15 CF.sub.3 Cl MetBu H B16 CF.sub.3 Cl MetBu H B17 CF.sub.3 Cl MetBu H B18 CF.sub.3 Cl MetBu H B19 CF.sub.3 Cl MetBu H B20 CF.sub.3 Cl MetBu H B21 CF.sub.3 Cl MetBu H B22 CF.sub.3 Cl MetBu H B23 CF.sub.3 Cl MetBu H B24 CF.sub.3 Cl MetBu H B25 CF.sub.3 Cl MetBu H B26 CF.sub.3 Cl MetBu H B27 CF.sub.3 Cl MetBu H B28 CF.sub.3 Cl MetBu H B29 CF.sub.3 Cl MetBu H B30 CF.sub.3 Cl MetBu H B31 CF.sub.3 Cl MetBu H B32 CF.sub.3 Cl MetBu H B33 CF.sub.3 Cl MetBu H B34 CF.sub.3 Cl MetBu H Na CF.sub.3 Cl MetBu H K CF.sub.3 Cl MetBu H B7 Cl H HtBu H B8 Cl H HtBu H B15 Cl H HtBu H B34 Cl H H2-pyridyl H H H CF.sub.3 Me2-pyridyl H H Me H Me2-pyridyl H H Me H CF.sub.32-pyridyl H B7 Me H H2-pyridyl H H Me Me Me2-pyridyl H H Me Cl Me2-pyridyl H H Me Br Me2-pyridyl H H Et Me Me2-pyridyl H H Cl Me Me2-pyridyl H H Cl H Me2-pyridyl H H Cl H CF.sub.32-pyridyl H H Cl H H2-pyridyl Me H Cl H H2-pyridyl Cl H Cl H H2-pyridyl H H Cl Cl Me2-pyridyl H H Cl Cl CF.sub.32-pyridyl H H Cl Cl CF.sub.2 H2-pyridyl H H Cl Cl CH.sub.2 OMe2-pyridyl H H Cl Cl COMe2-pyridyl H H Cl CF.sub.3 Me2-pyridyl H H Br Me Me2-pyridyl H H Me OMe Me2-pyridyl H H Br H H2-pyridyl H H OMe H H2-pyridyl H B7 OCF.sub.3 H H2-pyridyl H B7 SMe H H2-pyridyl H B7 NH.sub.2 H H2-pyridyl H B7 NHMe H H2-pyridyl H B7 NMe.sub.2 H H2-pyridyl H B7 NO.sub.2 H H2-pyridyl H B7 CN H H2-pyridyl H B7 CO.sub.2 Me H H2-pyridyl H B7 CO.sub.2 Et H H2-pyridyl H H CF.sub.3 Me Me2-pyridyl H H CF.sub.3 Cl Me2-pyridyl H H CF.sub.3 H Me2-pyridyl H H CF.sub.3 Br Me2-pyridyl H H CF.sub.3 CO.sub.2 Me Me2-pyridyl H H Cl NO.sub.2 Me2-pyridyl H H Cl CN Me2-pyridyl H H CO.sub.2 Me Me Me2-pyridyl H B3 Cl Cl Me2-pyridyl H B6 Cl Cl Me2-pyridyl H B7 Cl Cl Me2-pyridyl H B3 CF.sub.3 Cl Me2-pyridyl H B6 CF.sub.3 Cl Me2-pyridyl H B7 CF.sub.3 Cl Me2-pyridyl H B2 Cl H H2-pyridyl H B3 Cl H H2-pyridyl H B4 Cl H H2-pyridyl H B5 Cl H H2-pyridyl H B6 Cl H H2-pyridyl H B7 Cl H H2-pyridyl H B8 Cl H H2-pyridyl H B9 Cl H H2-pyridyl H B10 Cl H H2-pyridyl H B11 Cl H H2-pyridyl H B12 Cl H H2-pyridyl H B13 Cl H H2-pyridyl H B14 Cl H H2-pyridyl H B15 Cl H H2-pyridyl H B16 Cl H H2-pyridyl H B17 Cl H H2-pyridyl H B18 Cl H H2-pyridyl H B19 Cl H H2-pyridyl H B20 Cl H H2-pyridyl H B21 Cl H H2-pyridyl H B22 Cl H H2-pyridyl H B23 Cl H H2-pyridyl H B24 Cl H H2-pyridyl H B25 Cl H H2-pyridyl H B26 Cl H H2-pyridyl H B27 Cl H H2-pyridyl H B28 Cl H H2-pyridyl H B29 Cl H H2-pyridyl H B30 Cl H H2-pyridyl H B31 Cl H H2-pyridyl H B32 Cl H H2-pyridyl H B33 Cl H H2-pyridyl H B34 Cl H H2-pyridyl H Na Cl H H2-pyridyl H K Cl H H3-pyridyl H H Cl Cl Me3-pyridyl H H CF.sub.3 Cl Me3-pyridyl H H Cl H H4-pyridyl H H Cl Cl Me4-pyridyl H H CF.sub.3 Cl Me4-pyridyl H H Cl H H2-F--Ph H H Me Me Me2-F--Ph H H Me Cl Me2-F--Ph H H Cl Me Me2-F--Ph H H Cl H H2-F--Ph H H Cl Cl Me2-F--Ph H B7 OMe H H2-F--Ph H B7 SMe H H2-F--Ph H B7 CF.sub.3 Cl Me2-F--Ph H B7 CF.sub.3 H Me2-F--Ph H B1 Cl Cl Me2-F--Ph H B3 Cl Cl Me2-F--Ph H B6 Cl Cl Me2-F--Ph H B7 Cl Cl Me2-F--Ph H B3 CF.sub.3 Cl Me2-F--Ph H B6 CF.sub.3 Cl Me2-F--Ph H B7 CF.sub.3 Cl Me2-F--Ph H B7 Cl H H3-F--Ph H H Cl Cl Me4-F--Ph H H Cl Cl Me2,3-F.sub.2 --Ph H H Cl Cl Me2,4-F.sub.2 --Ph H H Cl Cl Me2,5-F.sub.2 --Ph H H Cl Cl MePh H H Me Me MePh H H Me Cl MePh H H Cl Me MePh H H Cl H HPh H H Cl Cl MePh H B7 OMe H HPh H B7 SMe H HPh H H CF.sub.3 Cl MePh H H CF.sub.3 H MePh H B1 Cl Cl MePh H B3 Cl Cl MePh H B6 Cl Cl MePh H B7 Cl Cl MePh H B3 CF.sub.3 Cl MePh H B6 CF.sub.3 Cl MePh H B7 CF.sub.3 Cl MePh Me B7 CF.sub.3 Cl MePh H B7 Cl H H3,4-F.sub.2 --Ph H H Cl Cl Me3,5-F.sub.2 --Ph H H Cl Cl Me2-Cl--Ph H H Me Me Me2-Cl--Ph H H Me Cl Me2-Cl--Ph H H Cl Me Me2-Cl--Ph H H Cl H H2-Cl--Ph H H Cl Cl Me2-Cl--Ph H H OMe H H2-Cl--Ph H H SMe H H2-Cl--Ph H H CF.sub.3 Cl Me2-Cl--Ph H H CF.sub.3 H Me2-Cl--Ph H B1 Cl Cl Me2-Cl--Ph H B3 Cl Cl Me2-Cl--Ph H B6 Cl Cl Me2-Cl--Ph H B7 Cl Cl Me2-Cl--Ph H B3 CF.sub.3 Cl Me2-Cl--Ph H B6 CF.sub.3 Cl Me2-Cl--Ph H B7 CF.sub.3 Cl Me2-Cl--Ph H B7 Cl H H3-Cl--Ph H H Cl Cl Me4-Cl--Ph H H Cl Cl Me2,3-Cl.sub.2 --Ph H H Cl Cl Me2,4-Cl.sub.2 --Ph H H Cl Cl Me2,5-Cl.sub.2 --Ph H H Cl Cl Me2,6-Cl.sub.2 --Ph H H Me Me Me2,6-Cl.sub.2 --Ph H H Me Cl Me2,6-Cl.sub.2 --Ph H H Cl Me Me2,6-Cl.sub.2 --Ph H H Cl H H2,6-Cl.sub.2 --Ph H H Cl Cl Me2,6-Cl.sub.2 --Ph H B7 OMe H H2,6-Cl.sub.2 --Ph H B7 SMe H H2,6-Cl.sub.2 --Ph H H CF.sub.3 Cl Me2,6-Cl.sub.2 --Ph H H CF.sub.3 H Me2,6-Cl.sub.2 --Ph H B1 Cl Cl Me2,6-Cl.sub.2 --Ph H B3 Cl Cl Me2,6-Cl.sub.2 --Ph H B6 Cl Cl Me2,6-Cl.sub.2 --Ph H B7 Cl Cl Me2,6-Cl.sub.2 --Ph Cl B7 Cl Cl Me2,6-Cl.sub.2 --Ph H B3 CF.sub.3 Cl Me2,6-Cl.sub.2 --Ph H B6 CF.sub.3 Cl Me2,6-Cl.sub.2 --Ph H B7 CF.sub.3 Cl Me2,6-Cl.sub.2 --Ph Cl B7 CF.sub.3 Cl Me2,6-Cl.sub.2 --Ph H B7 Cl H H3,4-Cl.sub.2 --Ph H H Cl Cl Me3,5-Cl.sub.2 --Ph H H Cl Cl Me2-Me--Ph H H Cl Cl Me2-Me--Ph H H CF.sub.3 Cl Me2,6-Me.sub.2 --Ph H H Cl Cl Me2,6-Me.sub.2 --Ph H H CF.sub.3 Cl Me2-MeO--Ph H H Cl Cl Me2-MeO--Ph H H CF.sub.3 Cl Me2-CF.sub.3 O--Ph H H Cl Cl Me2-CF.sub.3 O--Ph H H CF.sub.3 Cl Me2-SMe--Ph H H Cl Cl Me2-SMe--Ph H H CF.sub.3 Cl Me2-SOMe--Ph H H Cl Cl Me2-SOMe--Ph H H CF.sub.3 Cl Me2-SO.sub.2 Me--Ph H H Cl Cl Me2-SO.sub.2 Me--Ph H H CF.sub.3 Cl Me2-CF.sub.3 --Ph H H Cl Cl Me2-CF.sub.3 --Ph H H CF.sub.3 Cl Me2-NO.sub.2 --Ph H H Cl Cl Me2-NO.sub.2 --Ph H H CF.sub.3 Cl Me2-CN--Ph H H Cl Cl Me2-CN--Ph H H CF.sub.3 Cl Me2-NHMe--Ph H H Cl Cl Me2-NMe.sub.2 --Ph H H Cl Cl Me4-benzyl-Ph H H Cl Cl Me4-phenoxy-Ph H H Cl Cl Me2-OH--Ph H H Cl Cl Me2-CO.sub.2 Me--Ph H H Cl Cl Me2-CO.sub.2 Me--Ph H H CF.sub.3 Cl Me2-CO.sub.2 Et--Ph H H Cl Cl Me2-CO.sub.2 Et--Ph H H CF.sub.3 Cl MeH H H Cl Cl MeMe H H Cl Cl MeEt H H Cl Cl MenPr H H Cl Cl MeiPr H H Cl Cl MeiPr H H CF.sub.3 Cl MenBu H H Cl Cl MenBu H H CF.sub.3 Cl MeiBu H H Cl Cl MeiBu H H CF.sub.3 Cl MeiBu H B7 Cl Cl MeiBu H B7 CF.sub.3 Cl MeiBu H H Cl H HsecBu H H Cl Cl MesecBu H H CF.sub.3 Cl Me2,2-Me.sub.2 -propyl H H Cl Cl MenHex H H Cl Cl Meethenyl H H Cl Cl Me1-propenyl H H Cl Cl Me1-propenyl H H CF.sub.3 Cl Meethynyl H H Cl Cl Me1-propynyl H H Cl Cl MeCF.sub.3 H H Cl Cl MeCF.sub.3 H H CF.sub.3 Cl MeCHF.sub.2 H H Cl Cl MeC.sub.2 F.sub.5 H H Cl Cl Me2,2-Cl.sub.2 -cPr H H Cl Cl Me2,2-Cl.sub.2 -cPr H H CF.sub.3 Cl MecPr H H Cl Cl MecPr H H CF.sub.3 Cl Me1-Me-cPr H H Cl Cl Me1-Me-cPr H H CF.sub.3 Cl MecHex H H Cl Cl MecHex H H CF.sub.3 Cl MeCH.sub.2 Ph H H Cl Cl Menaphthyl-1 H H Cl Cl Menaphthyl-1 H H CF.sub.3 Cl Menaphthyl-2 H H Cl Cl MeCO.sub.2 Me H H Cl Cl MeCO.sub.2 Et H H Cl Cl Me2-thienyl H H Cl Cl Me2-thienyl H H CF.sub.3 Cl MeCH.sub.2 OMe H H Cl Cl MeCH.sub.2 OEt H H Cl Cl MeCOCH.sub.3 H H Cl Cl MeCOtBu H H Cl Cl MeCOPh H H Cl Cl Me______________________________________
TABLE 5__________________________________________________________________________ ##STR169## ##STR170## ##STR171## ##STR172## ##STR173## ##STR174## ##STR175## ##STR176## ##STR177## ##STR178## ##STR179## ##STR180## ##STR181## ##STR182## ##STR183## ##STR184## ##STR185## ##STR186## ##STR187## ##STR188## ##STR189## ##STR190## ##STR191## ##STR192## ##STR193## ##STR194## ##STR195## ##STR196## ##STR197## ##STR198## ##STR199## ##STR200## ##STR201## ##STR202## ##STR203## ##STR204## ##STR205## ##STR206## ##STR207## ##STR208## ##STR209## ##STR210##R.sup.1 R.sup.2 B Y.sup.1 Y.sup.2__________________________________________________________________________2,6-F.sub.2 --Ph H H Me H2,6-F.sub.2 --Ph H H Me Me2,6-F.sub.2 --Ph H H Et Me2,6-F.sub.2 --Ph Me H Et Me2,6-F.sub.2 --Ph H H Cl Cl2,6-F.sub.2 --Ph H H Cl Me2,6-F.sub.2 --Ph H H Cl CF.sub.32,6-F.sub.2 --Ph H H Me Cl2,6-F.sub.2 --Ph H H Br Me2,6-F.sub.2 --Ph H H Me CF.sub.32,6-F.sub.2 --Ph H H OMe Me2,6-F.sub.2 --Ph H H OCF.sub.3 Me2,6-F.sub.2 --Ph H H SMe Me2,6-F.sub.2 --Ph H H CO.sub.2 Me Me2,6-F.sub.2 --Ph H H CO.sub.2 Et Me2,6-F.sub.2 --Ph H H CF.sub.3 Me2,6-F.sub.2 --Ph H H CF.sub.3 H2,6-F.sub.2 --Ph H H CF.sub.3 Br2,6-F.sub.2 --Ph H H CF.sub.3 NO.sub.22,6-F.sub.2 --Ph H H CF.sub.3 CN2,6-F.sub.2 --Ph H H CF.sub.3 NHMe2,6-F.sub.2 --Ph H H CF.sub.3 NMe.sub.22,6-F.sub.2 --Ph H H CF.sub.3 CO.sub.2 Me2,6-F.sub.2 --Ph H B3 CF.sub.3 Me2,6-F.sub.2 --Ph H B6 CF.sub.3 Me2,6-F.sub.2 --Ph H B7 CF.sub.3 MetBu H H Me MetBu H H Et MetBu H H Cl CltBu H H Cl MetBu H H Me CltBu H H Cl CF.sub.3tBu H H Br MetBu H H Me BrtBu H H Me CF.sub.3tBu H H OMe MetBu H H OCF.sub.3 MetBu H H SMe MetBu H H CO.sub.2 Me MetBu H H CO.sub.2 Et MetBu H H CF.sub.3 MetBu H H CF.sub.3 HtBu H H CF.sub.3 BrtBu H H CF.sub.3 NO.sub.2tBu H B2 CF.sub.3 MetBu H B3 CF.sub.3 MetBu H B4 CF.sub.3 MetBu H B5 CF.sub.3 MetBu H B6 CF.sub.3 MetBu H B7 CF.sub.3 MetBu H B8 CF.sub.3 MetBu H B9 CF.sub.3 MetBu H B10 CF.sub.3 MetBu H B11 CF.sub.3 MetBu H B14 CF.sub.3 MetBu H B20 CF.sub.3 MetBu H B23 CF.sub.3 MetBu H B24 CF.sub.3 MetBu H B25 CF.sub.3 MetBu H B26 CF.sub.3 MetBu H B28 CF.sub.3 MetBu H B30 CF.sub.3 MetBu H B31 CF.sub.3 MetBu H B32 CF.sub.3 MetBu H B33 CF.sub.3 MetBu H B34 CF.sub.3 MetBu H Na CF.sub.3 MetBu H K CF.sub.3 Me2-pyridyl H H Me Me2-pyridyl H H Et Me2-pyridyl H H Cl Cl2-pyridyl H H Cl Me2-pyridyl H H Me Cl2-pyridyl H H Br Me2-pyridyl H H Me CF.sub.32-pyridyl H H CO.sub.2 Me Me2-pyridyl H H CO.sub.2 Et Me2-pyridyl H H CF.sub.3 Me2-pyridyl H H CF.sub.3 Br2-pyridyl H H CF.sub.3 NO.sub.22-pyridyl H H CF.sub.3 CN2-pyridyl H H CF.sub.3 NMe.sub.22-pyridyl H B3 CF.sub.3 Me2-pyridyl H B6 CF.sub.3 Me2-pyridyl H B7 CF.sub.3 Me3-pyridyl H H Et Me3-pyridyl H H CF.sub.3 Me4-pyridyl H H Et Me4-pyridyl H H CF.sub.3 Me2-F--Ph H H Me Me2-F--Ph H H Et Me2-F--Ph H H CF.sub.3 Me2-F--Ph H H CF.sub.3 Cl2-F--Ph H H CF.sub.3 H2-F--Ph H B3 CF.sub.3 Me2-F--Ph H B6 CF.sub.3 Me2-F--Ph H B7 CF.sub.3 Me3-F--Ph H H Et Me3-F--Ph H H CF.sub.3 Me4-F--Ph H H Et Me2,3-F.sub.2 --Ph H H Et Me2,4-F.sub.2 --Ph H H Et Me2,5-F.sub.2 --Ph H H Et MePh H H Me MePh H H Et MePh H H CF.sub.3 MePh H H CF.sub.3 ClPh H H CF.sub.3 HPh H B3 CF.sub.3 MePh H B6 CF.sub.3 MePh H B7 CF.sub.3 Me3,4-F.sub.2 --Ph H H Et Me3,5-F.sub.2 --Ph H H Et Me2-Cl--Ph H R Me Me2-Cl--Ph H H Et Me2-Cl--Ph H H CF.sub.3 Me2-Cl--Ph H H CF.sub.3 Cl2-Cl--Ph H H CF.sub.3 H2-Cl--Ph H B3 CF.sub.3 Me2-Cl--Ph H B6 CF.sub.3 Me2-Cl--Ph H B7 CF.sub.3 Me3-Cl--Ph H H CF.sub.3 Me4-Cl--Ph H H CF.sub.3 Me2,3-Cl.sub.2 --Ph H H CF.sub.3 Me2,4-Cl.sub.2 --Ph H H CF.sub.3 Me2,5-Cl.sub.2 --Ph H H CF.sub.3 Me2,6-Cl.sub.2 --Ph H H Me Me2,6-Cl.sub.2 --Ph H H Et Me2,6-Cl.sub.2 --Ph H H CF.sub.3 Me2,6-Cl.sub.2 --Ph H H CF.sub.3 Cl2,6-Cl.sub.2 --Ph H H CF.sub.3 H2,6-Cl.sub.2 --Ph H B3 CF.sub.3 Me2,6-Cl.sub.2 --Ph H B6 CF.sub.3 Me2,6-Cl.sub.2 --Ph H B7 CF.sub.3 Me3,4-Cl.sub.2 --Ph H H CF.sub.3 Me3,5-Cl.sub.2 --Ph H H CF.sub.3 Me2-Me--Ph H H Et Me2-Me--Ph H H CF.sub.3 Me2,6-Me.sub.2 --Ph H H Et Me2,6-Me.sub.2 --Ph H H CF.sub.3 Me2-MeO--Ph H H Et Me2-MeO--Ph H H CF.sub.3 Me2-CF.sub.3 O--Ph H H Et Me2-CF.sub.3 O--Ph H H CF.sub.3 Me2-SMe--Ph H H Et Me2-SMe--Ph H H CF.sub.3 Me2-SOMe--Ph H H Et Me2-SOMe--Ph H H CF.sub.3 Me2-SO.sub.2 Me--Ph H H Et Me2-SO.sub.2 Me--Ph H H CF.sub.3 Me2-CF.sub.3 --Ph H H Et Me2-CF.sub.3 --Ph H H CF.sub.3 Me2-NO.sub.2 --Ph H H Et Me2-NO.sub.2 --Ph H H CF.sub.3 Me2-CN--Ph H H Et Me2-NHMe.sub.2 --Ph H H CF.sub.3 Me2-NMe.sub.2 --Ph H H Et Me2-NMe.sub.2 --Ph H H CF.sub.3 Me4-benzyl-Ph H H CF.sub.3 Me4-phenoxy-Ph H H CF.sub.3 Me2-OH--Ph H H CF.sub.3 Me2-CO.sub.2 Me--Ph H H Et Me2-CO.sub.2 Me--Ph H H CF.sub.3 Me2-CO.sub.2 Et--Ph H H Et Me2-CO.sub.2 Et--Ph H H CF.sub.3 MeH H H CF.sub.3 MeMe H H CF.sub.3 MeEt H H CF.sub.3 MenPr H H CF.sub.3 MeiPr H H Et MeiPr H H CF.sub.3 MenBu H H Et MenBu H H CF.sub.3 MeiBu H H Et MeiBu H H CF.sub.3 MeiBu H B7 Et MeiBu H B7 CF.sub.3 MesecBu H H Et MesecBu H H CF.sub.3 Me2,2-Me.sub.2 -propyl H H CF.sub.3 MenHex H H CF.sub.3 Meethenyl H H CF.sub.3 Me1-propenyl H H Et Me1-propenyl H H CF.sub.3 Meethynyl H H CF.sub.3 Me1-propynyl H H CF.sub.3 MeCF.sub.3 H H Et MeCF.sub.3 H H CF.sub.3 MeCHF.sub.2 H H Et MeC.sub.2 F.sub.5 H H Et Me2,2-Cl.sub.2 -cPr H H Et Me2,2-Cl.sub.2 -cPr H H CF.sub.3 MecPr H H Et MecPr H H CF.sub.3 Me1-Me-cPr H H Et Me1-Me-cPr H H CF.sub.3 MecHex H H Et MecHex H H CF.sub.3 MeCH.sub.2 Ph H H CF.sub.3 Me1-naphthyl H H Et Me1-naphthyl H H CF.sub.3 Me2-naphthyl H H CF.sub.3 MeCO.sub.2 Me H H CF.sub.3 MeCO.sub.2 Et H H CF.sub.3 Me2-thienyl H H CF.sub.3 Me__________________________________________________________________________
TABLE 6______________________________________ ##STR211## ##STR212## ##STR213## ##STR214## ##STR215## ##STR216## ##STR217## ##STR218## ##STR219## ##STR220## ##STR221##R.sup.1 R.sup.2 B Y.sup.1 Y.sup.2 Y.sup.3______________________________________2,6-F.sub.2 --Ph H B7 H CF.sub.3 Me2,6-F.sub.2 --Ph H B7 Me H Me2,6-F.sub.2 --Ph H B7 Me H CF.sub.32,6-F.sub.2 --Ph H B7 Me H H2,6-F.sub.2 --Ph H B7 Me Me Me2,6-F.sub.2 --Ph H B7 Me Cl Me2,6-F.sub.2 --Ph H B7 Me Br Me2,6-F.sub.2 --Ph H B7 Et Me Me2,6-F.sub.2 --Ph H B7 Cl Me Me2,6-F.sub.2 --Ph H B7 Cl H Me2,6-F.sub.2 --Ph H B7 Cl H CF.sub.32,6-F.sub.2 --Ph H B7 Cl H H2,6-F.sub.2 --Ph H B7 Cl Cl CF.sub.32,6-F.sub.2 --Ph H B7 Cl Cl CF.sub.2 H2,6-F.sub.2 --Ph H B7 Cl Cl CH.sub.2 OMe2,6-F.sub.2 --Ph H B7 Cl Cl COMe2,6-F.sub.2 --Ph H B7 Cl CF.sub.3 Me2,6-F.sub.2 --Ph H B7 Br Me Me2,6-F.sub.2 --Ph H B7 Me OMe Me2,6-F.sub.2 --Ph H B7 OMe H H2,6-F.sub.2 --Ph H B7 OCF.sub.3 H H2,6-F.sub.2 --Ph H B7 SMe H H2,6-F.sub.2 --Ph H B7 CF.sub.3 Me Me2,6-F.sub.2 --Ph H B7 CF.sub.3 Cl CF.sub.32,6-F.sub.2 --Ph H B7 CF.sub.3 Cl CF.sub.2 H2,6-F.sub.2 --Ph H B7 CF.sub.3 Cl CH.sub.2 OMe2,6-F.sub.2 --Ph H B7 CF.sub.3 H Me2,6-F.sub.2 --Ph H B7 CF.sub.3 Br Me2,6-F.sub.2 --Ph H B7 CF.sub.3 NO.sub.2 Me2,6-F.sub.2 --Ph H B7 CF.sub.3 CN Me2,6-F.sub.2 --Ph H B7 CF.sub.3 NHMe Me2,6-F.sub.2 --Ph H B7 CF.sub.3 NMe.sub.2 Me2,6-F.sub.2 --Ph H B7 CF.sub.3 CO.sub.2 Me Me2,6-F.sub.2 --Ph H B7 CF.sub.3 OMe Me2,6-F.sub.2 --Ph H B7 CF.sub.3 OCF.sub.2 H CF.sub.2 H2,6-F.sub.2 --Ph H B7 Cl NO.sub.2 Me2,6-F.sub.2 --Ph H B7 Cl CN Me2,6-F.sub.2 --Ph H B7 CO.sub.2 Me Me Me2,6-F.sub.2 --Ph H B1 Cl Cl Me2,6-F.sub.2 --Ph Me B1 Cl Cl Me2,6-F.sub.2 --Ph H B3 Cl Cl Me2,6-F.sub.2 --Ph H B4 Cl Cl Me2,6-F.sub.2 --Ph H B5 Cl Cl Me2,6-F.sub.2 --Ph H B6 Cl Cl Me2,6-F.sub.2 --Ph H B7 Cl Cl Me2,6-F.sub.2 --Ph Me B7 Cl Cl Me2,6-F.sub.2 --Ph H B2 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B3 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B4 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B5 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B6 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B7 CF.sub.3 Cl Me2,6-F.sub.2 --Ph Me B7 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B8 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B9 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B10 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B11 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B12 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B13 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B14 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B15 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B16 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B17 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B18 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B19 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B20 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B21 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B22 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B23 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B24 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B25 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B26 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B27 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B28 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B29 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B30 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B31 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B32 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B33 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B34 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B7 Cl H H2,6-F.sub.2 --Ph H B9 Cl H H2,6-F.sub.2 --Ph H B10 Cl H H2,6-F.sub.2 --Ph H B11 Cl H H2,6-F.sub.2 --Ph H B45 CF.sub.3 Cl Me2,6-F.sub.2 --Ph H B46 CF.sub.3 Cl MetBu H B7 H CF.sub.3 MetBu H B7 Me H MetBu H B7 Me H CF.sub.3tBu H B7 Me H HtBu H B7 Me Me MetBu H B7 Me Cl MetBu H B7 Me Br MetBu H B7 Et Me MetBu H B7 Cl Me MetBu H B7 Cl H MetBu H B7 Cl H CF.sub.3tBu H B7 Cl H HtBu H B7 Cl Cl CF.sub.3tBu H B7 Cl Cl CF.sub.2 HtBu H B7 Cl Cl CH.sub.2 OMetBu H B7 Cl Cl COMetBu H B7 Cl CF.sub.3 MetBu H B7 Br Me MetBu H B7 Me OMe MetBu H B7 OMe H HtBu H B7 OCF.sub.3 H HtBu H B7 SMe H HtBu H B7 CF.sub.3 Me MetBu Br B7 CF.sub.3 Cl MetBu Me B7 CF.sub.3 Cl MetBu CF.sub.3 B7 CF.sub.3 Cl MetBu NO.sub.2 B7 CF.sub.3 Cl MetBu CN B7 CF.sub.3 Cl MetBu CO.sub.2 Me B7 CF.sub.3 Cl MetBu CO.sub.2 Et B7 CF.sub.3 Cl MetBu H B7 CF.sub.3 Cl CF.sub.3tBu H B7 CF.sub.3 Cl CF.sub.2 HtBu H B7 CF.sub.3 Cl CH.sub.2 OMetBu H B7 CF.sub.3 H MetBu H B7 CF.sub.3 Br MetBu H B7 CF.sub.3 NO.sub.2 MetBu H B7 CF.sub.3 CN MetBu H B7 CF.sub.3 NHMe MetBu H B7 CF.sub.3 NMe.sub.2 MetBu H B7 CF.sub.3 CO.sub.2 Me MetBu H B7 CF.sub.3 OMe MetBu H B7 CF.sub.3 OCF.sub.2 H CF.sub.2 HtBu H B7 Cl NO.sub.2 MetBu H B7 Cl CN MetBu H B7 CO.sub.2 Me Me MetBu H B1 Cl Cl MetBu H B2 Cl Cl MetBu H B3 Cl Cl MetBu H B4 Cl Cl MetBu H B5 Cl Cl MetBu H B6 Cl Cl MetBu H B7 Cl Cl MetBu Me B7 Cl Cl MetBu H B8 Cl Cl MetBu H B9 Cl Cl MetBu H B10 Cl Cl MetBu H B11 Cl Cl MetBu H B12 Cl Cl MetBu H B13 Cl Cl MetBu H B14 Cl Cl MetBu H B15 Cl Cl MetBu H B16 Cl Cl MetBu H B17 Cl Cl MetBu H B18 Cl Cl MetBu H B19 Cl Cl MetBu H B20 Cl Cl MetBu H B21 Cl Cl MetBu H B22 Cl Cl MetBu H B23 Cl Cl MetBu H B24 Cl Cl MetBu H B25 Cl Cl MetBu H B26 Cl Cl MetBu H B27 Cl Cl MetBu H B28 Cl Cl MetBu H B29 Cl Cl MetBu H B30 Cl Cl MetBu H B31 Cl Cl MetBu H B32 Cl Cl MetBu H B33 Cl Cl MetBu H B34 Cl Cl MetBu H B45 Cl Cl MetBu H B46 Cl Cl MetBu H B2 CF.sub.3 Cl MetBu H B3 CF.sub.3 Cl MetBu H B4 CF.sub.3 Cl MetBu H B5 CF.sub.3 Cl MetBu H B6 CF.sub.3 Cl MetBu H B7 CF.sub.3 Cl MetBu H B8 CF.sub.3 Cl MetBu H B9 CF.sub.3 Cl MetBu H B10 CF.sub.3 Cl MetBu H B11 CF.sub.3 Cl MetBu H B12 CF.sub.3 Cl MetBu H B13 CF.sub.3 Cl MetBu H B14 CF.sub.3 Cl MetBu H B15 CF.sub.3 Cl MetBu H B16 CF.sub.3 Cl MetBu H B17 CF.sub.3 Cl MetBu H B18 CF.sub.3 Cl MetBu H B19 CF.sub.3 Cl MetBu H B20 CF.sub.3 Cl MetBu H B21 CF.sub.3 Cl MetBu H B22 CF.sub.3 Cl MetBu H B23 CF.sub.3 Cl MetBu H B24 CF.sub.3 Cl MetBu H B25 CF.sub.3 Cl MetBu H B26 CF.sub.3 Cl MetBu H B27 CF.sub.3 Cl MetBu H B28 CF.sub.3 Cl MetBu H B29 CF.sub.3 Cl MetBu H B30 CF.sub.3 Cl MetBu H B31 CF.sub.3 Cl MetBu H B32 CF.sub.3 Cl MetBu H B33 CF.sub.3 Cl MetBu H B34 CF.sub.3 Cl MetBu H B35 CF.sub.3 Cl MetBu H B43 CF.sub.3 Cl MetBu H B7 Cl H HtBu H B9 Cl H HtBu H B10 Cl H HtBu H B11 Cl H H2-pyridyl H B7 H CF.sub.3 Me2-pyridyl H B7 Me H Me2-pyridyl H B7 Me H CF.sub.32-pyridyl H B7 Me H H2-pyridyl H B7 Me Me Me2-pyridyl H B7 Me Cl Me2-pyridyl H B7 Cl H Me2-pyridyl H B7 Cl H CF.sub.32-pyridyl H B7 OMe H H2-pyridyl H B7 OCF.sub.3 H H2-pyridyl H B7 SMe H H2-pyridyl H B7 NO.sub.2 H H2-pyridyl H B7 CO.sub.2 Me H H2-pyridyl H B7 CO.sub.2 Et H H2-pyridyl H B7 CF.sub.3 Me Me2-pyridyl H B7 CF.sub.3 H Me2-pyridyl H B7 CF.sub.3 Br Me2-pyridyl H B3 Cl Cl Me2-pyridyl H B7 Cl Cl Me2-pyridyl H B3 CF.sub.3 Cl Me2-pyridyl H B7 CF.sub.3 Cl Me2-pyridyl H B3 Cl H H2-pyridyl H B4 Cl H H2-pyridyl H B5 Cl H H2-pyridyl H B6 Cl H H2-pyridyl H B7 Cl H H2-pyridyl H B8 Cl H H2-pyridyl H B9 Cl H H2-pyridyl H B10 Cl H H2-pyridyl H B11 Cl H H2-pyridyl H B20 Cl H H2-pyridyl H B24 Cl H H2-pyridyl H B25 Cl H H2-pyridyl H B26 Cl H H2-pyridyl H B28 Cl H H2-pyridyl H B30 Cl H H2-pyridyl H B31 Cl H H2-pyridyl H B32 Cl H H2-pyridyl H B33 Cl H H2-pyridyl H B43 Cl H H2-pyridyl H B46 Cl H H3-pyridyl H B7 Cl Cl Me3-pyridyl H B7 Cl H H4-pyridyl H B7 Cl Cl Me4-pyridyl H B7 Cl H H2-F--Ph H B7 Me Me Me2-F--Ph H B7 Me Cl Me2-F--Ph H B7 Cl Me Me2-F--Ph H B7 Cl H H2-F--Ph H B7 OMe H H2-F--Ph H B7 SMe H H2-F--Ph H B7 CF.sub.3 H Me2-F--Ph H B1 Cl Cl Me2-F--Ph H B3 Cl Cl Me2-F--Ph H B6 Cl Cl Me2-F--Ph H B7 Cl Cl Me2-F--Ph H B3 CF.sub.3 Cl Me2-F--Ph H B6 CF.sub.3 Cl Me2-F--Ph H B7 CF.sub.3 Cl Me2-F--Ph H B7 Cl H H3-F--Ph H B7 Cl Cl Me4-F--Ph H B7 Cl Cl Me2,3-F.sub.2 --Ph H B7 CF.sub.3 Cl Me2,4-F.sub.2 --Ph H B7 Cl Cl Me2,5-F.sub.2 --Ph H B7 Cl Cl MePh H B7 Me Me MePh H B7 Me Cl MePh H B7 Cl Me MePh H B7 Cl H HPh H B7 OMe H HPh H B7 SMe H HPh H B7 CF.sub.3 H MePh H B1 Cl Cl MePh H B3 Cl Cl MePh H B6 Cl Cl MePh H B7 Cl Cl MePh H B3 CF.sub.3 Cl MePh H B6 CF.sub.3 Cl MePh H B7 CF.sub.3 Cl MePh Me B7 CF.sub.3 Cl MePh H B7 Cl H H3,4-F.sub.2 --Ph H B7 Cl Cl Me3,5-F.sub.2 --Ph H B7 Cl Cl Me2-Cl--Ph H B7 Me Me Me2-Cl--Ph H B7 Me Cl Me2-Cl--Ph H B7 Cl Me Me2-Cl--Ph H B7 Cl H H2-Cl--Ph H B7 OMe H H2-Cl--Ph H B7 SMe H H2-Cl--Ph H B7 CF.sub.3 H Me2-Cl--Ph H B6 Cl Cl Me2-Cl--Ph H B7 Cl Cl Me2-Cl--Ph H B3 CF.sub.3 Cl Me2-Cl--Ph H B6 CF.sub.3 Cl Me2-Cl--Ph H B7 CF.sub.3 Cl Me2-Cl--Ph H B7 Cl H H3-Cl--Ph H B7 Cl Cl Me4-Cl--Ph H B7 Cl Cl Me2,3-Cl.sub.2 --Ph H B7 Cl Cl Me2,4-Cl.sub.2 --Ph H B7 Cl Cl Me2,5-Cl.sub.2 --Ph H B7 Cl Cl Me2,6-Cl.sub.2 --Ph H B7 Me Me Me2,6-Cl.sub.2 --Ph H B7 Me Cl Me2,6-Cl.sub.2 --Ph H B7 Cl Me Me2,6-Cl.sub.2 --Ph H B7 Cl H H2,6-Cl.sub.2 --Ph H B7 OMe H H2,6-Cl.sub.2 --Ph H B7 SMe H H2,6-Cl.sub.2 --Ph H B7 CF.sub.3 H Me2,6-Cl.sub.2 --Ph H B1 Cl Cl Me2,6-Cl.sub.2 --Ph H B3 Cl Cl Me2,6-Cl.sub.2 --Ph H B6 Cl Cl Me2,6-Cl.sub.2 --Ph H B7 Cl Cl Me2,6-Cl.sub.2 --Ph Me B7 Cl Cl Me2,6-Cl.sub.2 --Ph H B3 CF.sub.3 Cl Me2,6-Cl.sub.2 --Ph H B6 CF.sub.3 Cl Me2,6-Cl.sub.2 --Ph H B7 CF.sub.3 Cl Me2,6-Cl.sub.2 --Ph Me B7 CF.sub.3 Cl Me3,4-Cl.sub.2 --Ph H B7 Cl Cl Me3,5-Cl.sub.2 --Ph H B7 Cl Cl Me2-Me--Ph H B7 Cl Cl Me2-Me--Ph H B7 CF.sub.3 Cl Me2,6-Me.sub.2 --Ph H B7 Cl Cl Me2,6-Me.sub.2 --Ph H B7 CF.sub.3 Cl Me2-MeO--Ph H B7 Cl Cl Me2-MeO--Ph H B7 CF.sub.3 Cl Me2-CF.sub.3 O--Ph H B7 Cl Cl Me2-CF.sub.3 O--Ph H B7 CF.sub.3 Cl Me2-SMe--Ph H B7 Cl Cl Me2-SOMe--Ph H B7 Cl Cl Me2-SO.sub.2 Me--Ph H B7 Cl Cl Me2-CF.sub.3 --Ph H B7 Cl Cl Me2-NO.sub.2 --Ph H B7 Cl Cl Me2-NO.sub.2 --Ph H B9 Cl Cl Me2-CN--Ph H B7 Cl Cl Me2-NHMe--Ph H B7 Cl Cl Me2-NMe.sub.2 --Ph H B7 Cl Cl Me4-benzyl-Ph H B7 Cl Cl Me4-phenoxy-Ph H B7 Cl Cl Me4-tBu--Ph H B1 Cl H Me2-OH--Ph H B7 Cl Cl Me2-CO.sub.2 Me--Ph H B7 Cl Cl Me2-CO.sub.2 Et--Ph H B7 Cl Cl MeH H B7 Cl Cl MeMe H B7 Cl Cl MeEt H B7 Cl Cl MenPr H B7 Cl Cl MeiPr H B7 Cl Cl MeiPr H B7 CF.sub.3 Cl MenBu H B7 Cl Cl MenBu H B7 CF.sub.3 Cl MeiBu H B7 Cl Cl MeiBu H B7 CF.sub.3 Cl MeiBu Me B7 Cl Cl MeiBu Me B7 CF.sub.3 Cl MeiBu H B7 Cl H HsecBu H B7 Cl Cl MesecBu H B7 CF.sub.3 Cl Mepentyl-2 H B1 Cl Cl Me2,2-Me.sub.2 -propyl H B7 Cl Cl MenHex H B7 Cl Cl Meethenyl H B7 Cl Cl Me1-propenyl H B7 Cl Cl Me1-propenyl H B7 CF.sub.3 Cl Meethynyl H B7 Cl Cl Me1-propynyl H B7 Cl Cl MeCF.sub.3 H B7 Cl Cl MeCHF.sub.2 H B7 Cl Cl MeC.sub.2 F.sub.5 H B7 Cl Cl Me2,2-Cl.sub.2 -cPr H B7 Cl Cl Me2,2-Cl.sub.2 -cPr H B7 CF.sub.3 Cl MecPr H B7 Cl Cl MecPr H B7 CF.sub.3 Cl Me1-Me-cPr H B7 Cl Cl Me1-Me-cPr H B7 CF.sub.3 Cl MecHex H B7 Cl Cl MecHex H B7 CF.sub.3 Cl MeCH.sub.2 Ph H B7 Cl Cl Menaphthyl-1 H B7 Cl Cl Menaphthyl-1 H B7 CF.sub.3 Cl Menaphthyl-2 H B9 Cl H Hnaphthyl-2 H B7 Cl Cl MeCO.sub.2 Me H B7 Cl Cl MeCO.sub.2 Et H B7 Cl Cl Me2-thienyl H B7 Cl Cl Me2-thienyl H B7 CF.sub.3 Cl MeCH.sub.2 OMe H B7 Cl Cl MeCH.sub.2 OEt H B7 Cl Cl MeCOCH.sub.3 H B7 Cl Cl MeCOtBu H B7 Cl Cl MeCOPh H B7 Cl Cl Me______________________________________
TABLE 7______________________________________ ##STR222## ##STR223## ##STR224## ##STR225## ##STR226## ##STR227## ##STR228## ##STR229## ##STR230## ##STR231## ##STR232## ##STR233## ##STR234##R.sup.1 R.sup.2 B Y.sup.1 Y.sup.2______________________________________Ph H B7 Me HPh H B7 Me MePh H B7 Et MePh Me B7 Et MePh H B7 Me ClPh H B7 Cl MePh H B7 Br MePh H B7 Me BrPh H B7 Me CF.sub.3Ph H B7 CF.sub.3 HPh H B7 CF.sub.3 BrPh H B7 CF.sub.3 NO.sub.2Ph H B7 CF.sub.3 CNPh H B4 CF.sub.3 MePh H B7 CF.sub.3 MePh H B9 CF.sub.3 MetBu H B7 Me MetBu H B7 Et MetBu H B7 Cl CltBu H B7 Cl MetBu H B7 Me CltBu H B7 Cl CF.sub.3tBu H B7 Br MetBu H B7 Me BrtBu H B7 Me CF.sub.3tBu H B7 CF.sub.3 MetBu H B7 CF.sub.3 HtBu H B7 CF.sub.3 BrtBu H B7 CF.sub.3 NO.sub.2tBu H B7 CF.sub.3 CNtBu H B4 CF.sub.3 MetBu H B5 CF.sub.3 MetBu H B6 CF.sub.3 MetBu H B7 CF.sub.3 MetBu H B9 CF.sub.3 MetBu H B20 CF.sub.3 MetBu H B24 CF.sub.3 MetBu H B25 CF.sub.3 MetBu H B26 CF.sub.3 Me2-pyridyl H B7 Me Me2-pyridyl H B7 Et Me2-pyridyl H B7 Cl Cl2-pyridyl H B7 Cl Me2-pyridyl H B7 Cl CF.sub.32-pyridyl H B7 Me Cl2-pyridyl H B7 Br Me2-thienyl H B7 Me CF.sub.32-pyridyl H B7 CF.sub.3 H2-pyridyl H B7 CF.sub.3 Br2-pyridyl H B7 CF.sub.3 Me3-pyridyl H B7 Et Me4-pyridyl H B7 CF.sub.3 Me2-F--Ph H B7 Me Me2-F--Ph H B7 Et Me2-F--Ph H B7 CF.sub.3 Cl2-F--Ph H B7 CF.sub.3 H2-F--Ph H B4 CF.sub.3 Me2-F--Ph H B7 CF.sub.3 Me2-F--Ph H B9 CF.sub.3 Me3-F--Ph H B7 Et Me4-F--Ph H B7 Et Me2,3-F.sub.2 --Ph H B7 Et Me2,4-F.sub.2 --Ph H B7 Et Me2,5-F.sub.2 --Ph H B7 Et Me2,6-F.sub.2 --Ph H B7 Me Me2,6-F.sub.2 --Ph H B7 Et Me2,6-F.sub.2 --Ph H B7 CF.sub.3 Cl2,6-F.sub.2 --Ph H B7 CF.sub.3 H2,6-F.sub.2 --Ph H B4 CF.sub.3 Me2,6-F.sub.2 --Ph H B7 CF.sub.3 Me2,6-F.sub.2 --Ph H B9 CF.sub.3 Me3,4-F.sub.2 --Ph H B7 Et Me3,5-F.sub.2 --Ph H B7 Et Me2-Cl--Ph H B7 Me Me2-Cl--Ph H B7 Et Me2-Cl--Ph H B7 CF.sub.3 Cl2-Cl--Ph H B7 CF.sub.3 H2-Cl--Ph H B4 CF.sub.3 Me2-Cl--Ph H B7 CF.sub.3 Me2-Cl--Ph H B9 CF.sub.3 Me3-Cl--Ph H B7 CF.sub.3 Me4-Cl--Ph H B7 CF.sub.3 Me2,3-Cl.sub.2 --Ph H B7 CF.sub.3 Me2,4-Cl.sub.2 --Ph H B7 CF.sub.3 Me2,5-Cl.sub.2 --Ph H B7 CF.sub.3 Me2,6-Cl.sub.2 --Ph H B7 Me Me2,6-Cl.sub.2 --Ph H B7 Et Me2,6-Cl.sub.2 --Ph H B7 CF.sub.3 Cl2,6-Cl.sub.2 --Ph H B7 CF.sub.3 H2,6-Cl.sub.2 --Ph H B4 CF.sub.3 Me2,6-Cl.sub.2 --Ph H B7 CF.sub.3 Me2,6-Cl.sub.2 --Ph H B9 CF.sub.3 Me3,4-Cl.sub.2 --Ph H B7 CF.sub.3 Me3,5-Cl.sub.2 --Ph H B7 CF.sub.3 Me2-Me--Ph H B7 Et Me2-Me--Ph H B7 CF.sub.3 Me2,6-Me.sub.2 --Ph H B7 Et Me2,6-Me.sub.2 --Ph H B7 CF.sub.3 Me2-MeO--Ph H B7 Et Me2-MeO--Ph H B7 CF.sub.3 Me2-CF.sub.3 O--Ph H B7 CF.sub.3 Me2-SMe--Ph H B7 CF.sub.3 Me2-SOMe--Ph H B7 CF.sub.3 Me2-SO.sub.2 Me--Ph H B7 CF.sub.3 Me2-CF.sub.3 --Ph H B7 CF.sub.3 Me2-NO.sub.2 --Ph H B7 CF.sub.3 Me2-CN--Ph H B7 CF.sub.3 Me2-NMe.sub.2 --Ph H B7 CF.sub.3 Me4-benzyl-Ph H B7 CF.sub.3 Me4-phenoxy-Ph H B7 CF.sub.3 Me2-OH--Ph H B7 CF.sub.3 Me2-CO.sub.2 Me--Ph H B7 Et Me2-CO.sub.2 Me--Ph H B7 CF.sub.3 Me2-CO.sub.2 Et--Ph H B7 Et Me2-CO.sub.2 Et--Ph H B7 CF.sub.3 MeH H B7 CF.sub.3 MeMe H B7 CF.sub.3 MeEt H B7 CF.sub.3 MenPr H B7 CF.sub.3 MeiPr H B7 Et MeiPr H B7 CF.sub.3 MenBu H B7 Et MenBu H B7 CF.sub.3 MeiBu H B7 Et MeiBu H B7 CF.sub.3 MesecBu H B7 Et MesecBu H B7 CF.sub.3 Me2,2-Me.sub.2 -propyl H B7 CF.sub.3 MenHex H B7 CF.sub.3 Meethenyl H B7 CF.sub.3 Me1-propenyl H B7 Et Me1-propenyl H B7 CF.sub.3 Meethynyl H B7 CF.sub.3 Me1-propynyl H B7 CF.sub.3 MeCF.sub.3 H B7 Et MeCHF.sub.2 H B7 CF.sub.3 MeC.sub.2 F.sub.5 H B7 CF.sub.3 Me2,2-Cl.sub.2 -cPr H B7 Et Me2,2-Cl.sub.2 -cPr H B7 CF.sub.3 MecPr H B7 Et MecPr H B7 CF.sub.3 Me1-Me-cPr H B7 Et Me1-Me-cPr H B7 CF.sub.3 MecHex H B7 Et MecHex H B7 CF.sub.3 MeCH.sub.2 Ph H B7 CF.sub.3 Menaphthyl-1 H B7 Et Menaphthyl-1 H B7 CF.sub.3 Menaphthyl-2 H B7 CF.sub.3 MeCO.sub.2 Me H B7 CF.sub.3 MeCO.sub.2 Et H B7 CF.sub.3 Me2-thienyl H B7 CF.sub.3 Me______________________________________
TABLE 8______________________________________ ##STR235## ##STR236## ##STR237## ##STR238## ##STR239## ##STR240## ##STR241## ##STR242## ##STR243## ##STR244## ##STR245## ##STR246## ##STR247## ##STR248## ##STR249## ##STR250## ##STR251## ##STR252## ##STR253## ##STR254## ##STR255## ##STR256## ##STR257## ##STR258## ##STR259## ##STR260## ##STR261## ##STR262## ##STR263##R.sup.1 R.sup.2 B W______________________________________2-F--Ph H H 2-F2,6-F.sub.2 --Ph H CO(2,4-Me.sub.2 --Ph) 2-FtBu H H 2-FtBu H B7 2-FtBuCH.sub.2 H B6 2-FEtMe.sub.2 C H B30 2-FcHex H B31 2-Cl1-Me-cHex H B32 2-BrPh H B33 2-F2-F--Ph H B34 2-F2-Cl H H 2-Me2-Cl--Ph H CO.sub.2 iPr 2-nBu2,6-F.sub.2 --Ph H CO(2-MeO--Ph) 2-OMe2,6-Cl.sub.2 --Ph H H 2-nBeO1-naphthyl Cl CO(4-MeO--Ph) 2-CF.sub.32-naphthyl Me CO(2-Me--Ph) 2-OCHF.sub.2tBu H Na 2-CF.sub.3tBu H Ca 2-OCH.sub.2 CH.sub.2 CHFCHF.sub.22-pyridyl H H 2-OCF.sub.2 CHF.sub.23-pyridyl H H 2-SMe4-pyridyl H B7 2-SOMeMe.sub.2 C.dbd.N-- H B10 2-SO.sub.2 MeiPr H B13 2-SCBrF.sub.2tBu H B19 2-SCF.sub.3tBuCH.sub.2 H B22 2-SOCBrF.sub.2EtMe.sub.2 C H B23 2-SO.sub.2 CH.sub.2 FcHex H B7 2-SCF.sub.3Ph H B25 2-SCBrF.sub.22-F--Ph H B26 2-SO.sub.2 CHF.sub.22-F--Ph H B27 2-SCBrF.sub.22-CF.sub.3 --Ph H B28 2-CH.dbd.CCl.sub.22,6-F.sub.2 --Ph H CO(2,6-Me.sub.2 --Ph) 2-OCH.sub.2 CH.dbd.CH.sub.21-naphthyl H CO(2,6-(MeO).sub.2 --Ph) 2-OCH.sub.2 CH.dbd.CCl.sub.2PhCH.sub.2 H CO(2-Me-6-NO.sub.2 --Ph) 2-OCH.sub.2 CH.dbd.CHCl2-thienyl H CO(3,4,5-(MeO).sub.3 --Ph) 2-SCH.sub.2 CH.dbd.CHMe4-Cl-2-thienyl H SO.sub.2 (4-Me--Ph) 2-SOCH.sub.2 CH.dbd.CH.sub.23-MeO-2-pyridyl H CO(2,6-Cl.sub.2 --Ph) 2-SO.sub.2 CHMeCH.dbd.CH.sub.22-Cl-3-pyridyl H CO(2,5-Me.sub.2 --Ph) 2-SCH.sub.2 CMe.dbd.CF.sub.22,6-Cl.sub.2 -4-pyridyl H CO(2,6-F.sub.2 --Ph) 2-SOCH.sub.2 CF.dbd.CF.sub.2EtMeC.dbd.N-- H B1 2-SO.sub.2 CH.sub.2 CH.dbd.CF.sub.2Et H B2 2-CCHtBu H B4 2-CCItBuCH.sub.2 H H 2-OCH.sub.2 CCHEtMe.sub.2 C H H 2-OCH.sub.2 CCClcHex H H 2-SCH.sub.2 CCMePh H H 2-SOCH.sub.2 CCH2-MeO--Ph H B5 2-SO.sub.2 CH.sub.2 CCMe2-F--Ph H B6 2-SCH.sub.2 CCBr2,6-F.sub.2 --Ph H B7 2-SOCHMeCCCl2,6-Me.sub.2 --Ph H B8 2-SO.sub.2 CH.sub.2 CCI1-naphthyl H Ba 2-NO.sub.2PhCH.sub.2 H K 2-CN2-naphthyl H H 2-CO.sub.2 Me5-Br-3-thienyl H B3 2-COMe3-MeO-2-pyridyl H B14 2-O(CO)Me2-Cl-3-pyridyl H B15 2-NHMe2,6-Cl.sub.2 -4-pyridyl H B16 2-NMe.sub.2(CH.sub.2).sub.4 C.dbd.N-- H B17 3-FtBu H H 3-CltBuCH.sub.2 H H 3-nBuEtMe.sub.2 C H H 3-OEt2-Me-cHex H H 3-CH.sub.2 CH.sub.2 CH.sub.2 CHF.sub.2Ph H B22 3-OCH.sub.2 CH.sub.2 CHFCHF.sub.2Ph H B27 3-S-nBu2-CF.sub.3 --Ph H B28 3-SOnPr2,6-F.sub.2 --Ph H B30 3-SO.sub.2 iPr2,6-Me.sub.2 --Ph H B31 3-SCF.sub.31-naphthyl H CO(3,4-(MeO).sub.2 --Ph) 3-SCH.sub.2 CH.sub.2 CHFCHF.sub.2PhCH.sub.2 H CO(2,4-Cl.sub.2 --Ph) 3-SO.sub.2 CF.sub.2 CHF.sub.22-thienyl H CO(3-CF.sub.3 --Ph) 3-SCH.sub.2 CMe.dbd.CH.sub.23-Me-2-pyridyl H CO(2-Me.sub.2 N--Ph) 3-SOCH.sub.2 CH.dbd.CH.sub.23-NO.sub.2 -2-pyridyl H COiPr 3-SO.sub.2 CHMeCH.dbd.CH.sub.23,6-Cl.sub.2 -2-pyridyl H CO.sub.2 iPr 3-SCH.sub.2 CMe.dbd.CF.sub.22-MeS-3-pyridyl H CO.sub.2 tBu 3-SOCH.sub.2 CF.dbd.CCl.sub.2(CH.sub.2).sub.5 C.dbd.N-- H CONHMe 3-SO.sub.2 CH.sub.2 CH.dbd.CH.sub.2 ClsBu H CONHEt 3-OCH.sub.2 CCHtBuCH.sub.2 H B19 3-SCH.sub.2 CCMeEtMe.sub.2 C H B18 3-SOCH.sub.2 CCH2-Me-cHex H SO.sub.2 (2-Me--Ph) 3-SO.sub.2 CH.sub.2 CCMePh H H 3-NO.sub.22-CF.sub.3 O--Ph H H 3-CN2-MeS--Ph H H 3-CO.sub.2 Et2,6-F.sub.2 --Ph H Na 3-COnPr2,6-Cl.sub.2 --Ph H K 3-O(CO)nPr1-naphthyl H Mg 3-NHBu3-F-2-pyridyl H Ca 3-NEt.sub.26-Me-2-pyridyl H Ba 4-F4-CF.sub.3 -3-pyridyl H COCEtMe.sub.2 4-Cl3-NO.sub.2 -3-pyridyl H CO(3-MeO--Ph) 4-Br2,4-Me.sub.2 -3-pyridyl H CO-2-naphtyl 4-IiBuMeC.dbd.N-- H CO(4-EtO-3-MeO--Ph) 4-MetBu H CO(3-Cl-4-MeO--Ph) 4-tButBu H CO(3-F-4-nBuO--Ph) 4-OMetBu H CH.sub.2 CO.sub.2 Me 4-CF.sub.3Ph H CH(Me)CO.sub.2 Et 4-OCHF.sub.2Ph H CMe.sub.2 CO.sub.2 nPr 4-SMe2-pyridyl H CH.sub.2 CN 4-SOMesBu H CH.sub.2 CH.sub.2 CH.sub.2 CN 4-SO.sub.2 nButBuCH.sub.2 H CH.sub.2 CO.sub.2 iPr 4-SCF.sub.3EtMe.sub.2 C H H 4-SOCBrF.sub.22-Me-cHex H H 4-SO.sub.2 CH.sub.2 FPh H H 4-OCH.sub.2 CH.dbd.CH.sub.22-CF.sub.3 --Ph H H 4-OCH.sub.2 CH.dbd.CCl.sub.22-NO.sub.2 --Ph H B3 4-OCH.sub.2 CCH2,6-F.sub.2 --Ph H B4 4-OCH.sub.2 CCCl2-Cl-6-F--Ph H B5 4-SCH.sub.2 CCMe1-naphthyl H B6 4-SO.sub.2 CH.sub.2 CCMe2-pyridyl H B7 4-NO.sub.23-pyridyl H B8 4-CNPhCH.sub.2 H B12 4-CO.sub.2 nBu2-thienyl H B21 4-COiBu3-thienyl H B28 4-O(CO)nPriBuMeC.dbd.N-- H CO(2-MeO--Ph) 4-NHnButBu H H 2,3-Cl.sub.2tBu H H 2,4-Cl.sub.2tBu H H 3,4-Cl.sub.2Ph H H 3,5-Cl.sub.2Ph H H 2,5-Cl.sub.22-pyridyl H B7 2,6-Cl.sub.2sBu H B8 2,6-Cl.sub.2tBuCH.sub.2 H B12 2,6-Cl.sub.2EtMe.sub.2 C H B23 2,3-F.sub.22-Me-cHex H B26 2,3-F.sub.2Ph H B28 2,3-F.sub.22-Me--Ph H CONHiPr 2,4-F.sub.22-MeO--Ph H Ca 2,4-F.sub.22,6-F.sub.2 --Ph H Ba 2,5-F.sub.22,6-Cl.sub.2 --Ph H H 2,6-F.sub.21-naphthyl H H 2,6-F.sub.22-pyridyl H H 2,6-F.sub.2PhCH.sub.2 H CO(2,3-Me.sub.2 --Ph) 2,6-F.sub.23-pyridyl H CO(3,4-Me.sub.2 --Ph) 2,6-F.sub.24-pyridyl H CH.sub.2 CO.sub.2 Et 2,6-F.sub.22-thienyl H CHMeCO.sub.2 Me 2,6-F.sub.2iBuMeC.dbd.N-- H CH.sub.2 CN 2,6-F.sub.2tBu H H 2,6-F.sub.2tBu H B7 2,6-F.sub.2tBu H B8 2,6-F.sub.2tBu H B28 2,6-F.sub.2tBu Me B31 2,6-F.sub.2tBu H B34 2,6-F.sub.2tBu H CO(2-MeO--Ph) 2,6-F.sub.2tBu H CO(2-Cl--Ph) 2,6-F.sub.2tBu H CO(2,6-Me.sub.2 --Ph) 2,6-F.sub.2tBuCH.sub.2 H CO(2,6-(MeO).sub.2 --Ph) 2,6-F.sub.2EtMe.sub.2 C H CO(3,4,5-(MeO).sub.3 --Ph) 2,6-F.sub.2cHex H B28 2,6-F.sub.2cHex H B30 2,6-F.sub.2cHex H B34 2,6-F.sub.21-Me-cHex H SO.sub.2 (4-Cl--Ph) 2,6-F.sub.2Ph H H 2,6-F.sub.2Ph H B5 2,6-F.sub.2Ph H B6 2,6-F.sub.22-F--Ph H B14 2,6-F.sub.23-F--Ph H B19 2,6-F.sub.24-F--Ph H B23 2,6-F.sub.22-Cl--Ph H B24 2,6-F.sub.22,6-F.sub.2 --Ph H H 2,6-F.sub.22,6-F.sub.2 --Ph H Ca 2,6-F.sub.22,6-F.sub.2 --Ph Me B7 2,6-F.sub.22,6-F.sub.2 --Ph H B9 2,6-F.sub.21-naphthyl H B10 2,6-F.sub.22-naphthyl H B16 2,6-F.sub.22-thienyl H B22 2,6-F.sub.23-thienyl H B24 2,6-F.sub.22-pyridyl Cl H 3,4-F.sub.23-pyridyl H B7 3,5-F.sub.24-pyridyl H B18 2,5-(CF.sub.3).sub.2nPr.sub.2 C.dbd.N-- H B31 2,6-(CF.sub.3).sub.2tBu Et H 3,5-(CF.sub.3).sub.2tBu Br H 5-Br-2-CltBu H SO.sub.2 (4-Me--Ph) 3-Br-4-MetBu H COnHex 2-Cl-4-FtBu H CO(2-Cl-6-F--Ph) 2-Cl-6-FtBuCH.sub.2 H CO(3,5-Cl.sub.2 -4-MeO--Ph) 2-Cl-6-FEtMe.sub.2 C H CO(3-Br-4-Me--Ph) 2-Cl-6-FcHex H H 2-Cl-6-FcHex H B6 2-Cl-6-FPh H B7 2-Cl-6-FPh H B8 2-Cl-6-F2-F--Ph H B34 2-Cl-6-F3-F--Ph H CO.sub.2 tBu 2-Cl-6-F2-Cl--Ph H CHMeCO.sub.2 Me 2-Cl-6-F2,6-F.sub.2 --Ph H B31 3-Cl-4-F2,6-F.sub.2 --Ph H K 4-Cl-3-FtBu H Ba 2-F-6-I2,6-F.sub.2 --Ph H CO(4-nBuO--Ph) 2-F-6-I2,6-F.sub.2 --Ph H CO(4-Et.sub.2 N--Ph) 2-F-6-I2,6-F.sub.2 --Ph Br CO(3-Me.sub.2 N--Ph) 2-Cl-5-SMe1-naphthyl H CO(4-Et--Ph) 2-Cl-5-SCBrF.sub.22-naphthyl H CO(3-F-4-Me--Ph) 2-Cl-5-SCF.sub.32-thienyl H CO(3-MeO-4-Me--Ph) 2-Cl-5-SOMe3-thienyl H CO(2,3,6-F.sub.3 --Ph) 2-Cl-5-SO.sub.2 Me2-pyridyl H CO(2-MeO-5-NO.sub.2 --Ph) 2-Cl-4-NO.sub.23-pyridyl H CO(3,5-Me.sub.2 --Ph) 2,4-(OMe).sub.24-pyridyl H H 2,6-(OMe).sub.2nPr.sub.2 C.dbd.N-- H H 2,6-(OMe).sub.2tBu H H 2,3-Me.sub.2tBu H B1 2,4-Me.sub.2tBu H B2 2,5-Me.sub.2tBuCH.sub.2 H B3 2,6-Me.sub.2EtMe.sub.2 C H B4 2,6-Me.sub.2cHex H B5 2,6-Me.sub.2cHex H B6 3,4-Me.sub.21-Me-cHex H B7 3,5-Me.sub.2Ph H B8 2-F-4-MePh H B9 2-F-4-MePh H B10 2-F-4-Me2-F--Ph H B11 3-F-4-Me2-F--Ph H B12 3-I-4-Me3-F--Ph H B13 2-OMe-4-SMe4-F--Ph H B14 3-OMe-4-NO.sub.22-Cl--Ph H CH.sub.2 CN 2-Me-4-NO.sub.22,6-F.sub.2 --Ph H CMe.sub.2 CO.sub.2 Et 2-Me-6-NO.sub.22,6-F.sub.2 --Ph H CONHMe 2,3,6-F.sub.3tBu H SO.sub.2 (4-Cl--Ph) 2,3,6-F.sub.3cHex H CO(2-MeO--Ph) 2,3,6-F.sub.31-naphthyl H CO(2-Me--Ph) 2,3,6-F.sub.32-F--Ph H CO(2-Cl--Ph) 2,3,6-F.sub.32-pyridyl H CO(2,6-(MeO).sub.2 --Ph) 2,4,5-F.sub.33-pyridyl H CO(3,4-Me.sub.2 --Ph) 2,4,5-F.sub.34-pyridyl H CO(3-MeO-4-EtO--Ph) 2,4,5-F.sub.3nPr.sub.2 C.dbd.N-- H B15 2,3,5-I.sub.3tBu H B16 2,3,5-I.sub.3tBu H B17 2,3,4-(OMe).sub.3tBu H B18 2,4,5-(OMe).sub.3tBu H B19 3,4,5-(OMe).sub.3tBu H B20 2,4,6-Me.sub.3tBuCH.sub.2 H B21 2,3,4,5-F.sub.4EtMe.sub.2 C H B24 2,3,4,5-F.sub.4cHex H B25 2,3,4,5-F.sub.4cHex H B27 2,3,5,6-F.sub.4cHex H B28 2,3,5,6-F.sub.41-Me-cHex H B29 2,3,5,6-F.sub.4Ph H B30 2,3,5,6-F.sub.4Ph H B31 2,3,4,5,6-F.sub.5Ph H B32 2,3,4,5,6-F.sub.52-F--Ph H B33 2,3,4,5,6-F.sub.53-F--Ph H B34 2,3,5,6-F.sub.4 -4-Me4-F--Ph H H 2,3,5,6-F.sub.4 -4-Me2-Cl--Ph H H 2,3,5,6-F.sub.4 -4-Me2,6-F.sub.2 --Ph H B27 2,3,5,6-F.sub.4 -4-Me2,6-F.sub.2 --Ph H Ca 2,3,5,6-F.sub.4 -4-Me______________________________________
TABLE 9______________________________________ ##STR264## ##STR265## ##STR266## ##STR267## ##STR268## ##STR269## ##STR270## ##STR271## ##STR272## ##STR273## ##STR274## ##STR275## ##STR276## ##STR277## ##STR278## ##STR279## ##STR280## ##STR281## ##STR282## ##STR283## ##STR284## ##STR285## ##STR286## ##STR287## ##STR288## ##STR289## ##STR290## ##STR291## ##STR292## ##STR293##R.sup.1 B Y.sup.1______________________________________Me H HEt B1 MeiPr B2 EtnBu B3 nPrsBu B4 iButBu H nHextBu B7 MetBu B8 MeOtBu B8 MeStBu B7 CF.sub.3tBu B5 CF.sub.3tBu B7 CClF.sub.2tBu B8 CF.sub.3 CF.sub.2tBu 4-Cl--PhCO.sub.2 CF.sub.3 CF.sub.2 CF.sub.2tPen B6 MeOnHex B7 EtOnHep B8 iPrOnOct B9 sBuOnNon B10 MeSnDec B11 EtSPhCH.sub.2 B12 nPrSPh(Me)CH B13 tBuSPhMe.sub.2 C B14 PhPhMe.sub.2 C B7 MePhMe.sub.2 C B8 MePhMe.sub.2 C B33 MePhMe.sub.2 C B34 MePhMe.sub.2 C B41 MePhMe.sub.2 C B7 CF.sub.3PhMe.sub.2 C B8 CF.sub.3PhMe.sub.2 C B34 CF.sub.34-Cl--PhMe.sub.2 C B15 Me.sub.2 N3-Br--PhEtMeC B16 Et.sub.2 N4-Me--Ph(CH.sub.2).sub.3 B17 HCH.sub.2 .dbd.CMe B18 MeCF.sub.3 CF.sub.2 CF.sub.2 B19 EtcPr B20 nPrcPen B21 iBucPen B22 nHexcPen B23 CF.sub.3cHex B24 CClF.sub.2cHex B7 CF.sub.3cHex B8 CF.sub.3cHex B33 CF.sub.3cHex B34 CF.sub.3cHex B7 MecHex B8 MecHex B34 Me1-Me-cHex B7 Me1-Me-cHex B8 CF.sub.31-Me-cHex B7 CF.sub.31-Me-cHex iBuOC(O) CF.sub.31-Me-cHex B28 EtO1-Me-cHex B29 iPrOEtO B30 sBuOiPrO B31 MeSCF.sub.3 O B32 EtStBuOC(O) B33 nPrSPh B34 tBuS2-F--Ph B35 Ph2-F--Ph B36 Me.sub.2 N2-Cl--Ph B37 Et.sub.2 N2-Cl--Ph B38 Cl2-Br--Ph B39 Br2-I--Ph B40 I2-CF.sub.3 --Ph B41 H2-MeO--Ph B42 CF.sub.33,4-Cl.sub.2 --Ph CClF.sub.2 C(O) MeO2,4-Me.sub.2 --Ph PhSC(O) MeS2,6-F.sub.2 --Ph B7 Me2,6-F.sub.2 --Ph B7 CF.sub.32,6-F.sub.2 --Ph B8 Me2,6-F.sub.2 --Ph B8 CF.sub.32,6-F.sub.2 --Ph EtSC(O) H2,6-F.sub.2 --Ph tBuC(S) Me2,6-F.sub.2 --Ph cPenOC(O) Et2-pyridyl cHexOC(O) nPr2-pyridyl B7 Me2-pyridyl B8 Me2-pyridyl B7 CF.sub.32-pyridyl B8 CF.sub.32-pyridyl iBuOC(O) CF.sub.32-pyridyl B33 CF.sub.32-pyridyl B34 CF.sub.32-pyridyl B34 Me2-pyridyl 2-pyridyl-C(O) CClF.sub.22-pyridyl 2-pyridyl-C(O) CF.sub.3 CF.sub.22-thienyl 3-pyridyl-C(O) CF.sub.3 CF.sub.2 CF.sub.21-naphthyl 4-pyridyl-C(O) MeO2-naphthyl H EtOtBu CClF.sub.2 C(O) HtBu PhSC(O) MetBu EtSC(O) EttBu tBuC(S) nPrcPr cPenOC(O) iBucPen cHexOC(O) nHexcHex B7 CF.sub.31-Et-cPr B8 CClF.sub.21-Me-cPen iBuOC(O) CF.sub.3 CF.sub.21-Me-cPen 2-pyridyl-C(O) CF.sub.3 CF.sub.2 CF.sub.22,6-F.sub.2 --Ph 2-pyridyl-C(O) MeO2,6-F.sub.2 --Ph 2-pyridyl-C(O) MeO2,6-F.sub.2 --Ph 4-pyridyl-C(O) Me2,6-F.sub.2 --Ph 2-pyridyl-C(O) CF.sub.3______________________________________
TABLE 10__________________________________________________________________________ ##STR294## ##STR295## ##STR296## ##STR297## ##STR298## ##STR299## ##STR300## ##STR301## ##STR302## ##STR303## ##STR304## ##STR305## ##STR306## ##STR307## ##STR308## ##STR309## ##STR310## ##STR311##R.sup.1 B A R.sup.1 B A__________________________________________________________________________Et H A1 tBu B15 A8iPr B7 A2 tBu B34 A8iBu B7 A1 tBu H A9sBu B7 A2 tBu B7 A9tBu B7 A1 tBu B8 A9tBu B8 A1 tBu B15 A9tBu B15 A1 tBu B34 A9tBu B34 A1 tBu CO.sub.2 -iBu A9tBu B7 A2 tBu H A10tBu B8 A2 tBu B7 A10tBu B15 A2 tBu B8 A10tBu B34 A2 tBu B15 A10tBu CO.sub.2 -iBu A2 tBu B34 A10tBu B7 A3 tBu CO.sub.2 -iBu A10tBu B7 A4 tBu R A11tBu B7 A5 tBu B7 A11tBu B7 A6 tBu B8 A11tBu H A7 tBu B15 A11tBu B7 A7 tBu H A12tBu B8 A7 tBu B7 A12tBu B15 A7 tBu B8 A12tBu B34 A7 tBu B15 A12tBu H A8 tBu B34 A12tBu B7 A8 tBu CO.sub.2 -iBu A12tBu B8 A8 tBu H A13tBu B7 A13 tBu B17 A27tBu B8 A13 tBu B18 A28tBu B15 A13 tBu B19 A29tBu B34 A13 tBu B7 A30tBu CO.sub.2 -iBu A13 tBu B8 A30tBu H A14 tBu B15 A30tBu B7 A14 tBu B20 A31tBu B16 A14 tBu H A32tBu B17 A14 tBu B7 A32tBu B7 A15 tBu B8 A32tBu B8 A16 tBu B15 A32tBu B9 A17 tBu B34 A32tBu B10 A18 tBu CO.sub.2 -iBu A32tBu B11 A19 tBu B21 A33tBu B12 A20 tBu B22 A34tBu B13 A21 tBu B23 A35tBu B7 A22 tBu B24 A36tBu B8 A22 tBuCH.sub.2 B3 A1tBu B7 A23 tBuCH.sub.2 B7 A2tBu B8 A23 tBuCH.sub.2 B8 A2tBu B15 A23 Et(Me).sub.2 C B15 A2tBu B34 A23 Et(Me).sub.2 C B16 A2tBu B14 A24 Et(Me).sub.2 C B34 A2tBu B15 A25 Et(Me).sub.2 C H A2tBu B16 A26 Et(Me).sub.2 C B7 A2nHex B7 A1 Ph B7 A10nHep B7 A2 Ph B7 A13nOct B7 A1 Ph B7 A32nNon B7 A2 2-F--Ph B7 A1nDec B7 A7 2-F--Ph B7 A2cPr B7 A8 2-F--Ph B7 A71-Me-cPr B7 A1 2-F--Ph B7 A81-Me-cPr B7 A2 2-F--Ph B7 A91-Me-cPr B8 A2 2-F--Ph B7 A101-Me-cPr B34 A2 2-F--Ph B7 A131-Me-cPr H A2 2-F--Ph B8 A32cPen B7 A2 2-Cl--Ph B7 A1cHex B7 A1 2-Cl--Ph B7 A2cHex B7 A2 2-Cl--Ph B7 A7cHex B8 A2 2-Cl--Ph B7 A8cHex B15 A2 2-Cl--Ph B7 A9cHex B34 A2 2-Cl--Ph B7 A10cHex B35 A2 2-Cl--Ph B7 A13cHex B36 A1 2-Cl--Ph B8 A30cHex B37 A2 2-Cl--Ph B34 A32Ph H A2 2-Br--Ph B7 A1Ph B7 A2 2-I--Ph B7 A2Ph B7 A7 2-Me--Ph B7 A7Ph B7 A8 2-Me--Ph B7 A8Ph B7 A9 2-Me--Ph B7 A92-Me--Ph B7 A1 2,6-Cl.sub.2 --Ph B7 A12-Me--Ph B7 A2 2,6-Cl.sub.2 --Ph B7 A22-MeO--Ph B2 A7 2,6-Cl.sub.2 --Ph B7 A72-CF.sub.3 --Ph B3 A8 2,6-F.sub.2 --Ph B7 A12-NO.sub.2 --Ph B4 A9 2,6-F.sub.2 --Ph B7 A22-CN--Ph B5 A10 2,6-F.sub.2 --Ph B7 A72-CBrF.sub.2 O--Ph B6 A11 2,6-F.sub.2 --Ph B7 A82-CF.sub.3 O--Ph B7 A12 2,6-F.sub.2 --Ph B7 A92-MeS--Ph B8 A13 2,6-F.sub.2 --Ph B7 A102-nBuS--Ph B9 A14 2,6-F.sub.2 --Ph B7 A132-MeSO--Ph B10 A15 2,6-F.sub.2 --Ph B7 A212-MeSO.sub.2 --Ph B11 A16 2,6-F.sub.2 --Ph B7 A322-CH.sub.2 .dbd.CHCH.sub.2 S--Ph B12 A17 2,6-F.sub.2 --Ph B3 A22-CH.sub.2 .dbd.CHCH.sub.2 SO--Ph B13 A18 2,6-F.sub.2 --Ph B4 A22-CH.sub.2 .dbd.CHCH.sub.2 SO.sub.2 --Ph B14 A19 2,6-F.sub.2 --Ph B5 A22-CF.sub.3 S--Ph B15 A20 2,6-F.sub.2 --Ph B8 A22-CHF.sub.2 S--Ph B16 A21 2,6-F.sub.2 --Ph B15 A22-CBrF.sub.2 SO--Ph B17 A22 2,6-F.sub.2 --Ph B19 A22-CF.sub.3 SO.sub.2 --Ph B18 A23 2,6-F.sub.2 --Ph B32 A22-CHO--Ph B19 A24 2,6-F.sub.2 --Ph B33 A22-OH--Ph B20 A25 2,6-F.sub.2 --Ph B34 A22-Me.sub.2 N--Ph B21 A26 2,6-F.sub.2 --Ph B35 A23-Ph--Ph B22 A27 2,6-F.sub.2 --Ph B37 A24-PhO--Ph B23 A28 2,6-F.sub.2 --Ph B40 A22-MeOC(O)--Ph B24 A29 2,6-F.sub.2 --Ph B43 A2Cl B7 A1 ClCC B3 A23PhCH.sub.2 B7 A1 2,2-Cl.sub.2 -cPr B4 A23PhCH.sub.2 B7 A2 2,2-F.sub.2 -cBu B5 A23PhCH.sub.2 B8 A2 MeO B6 A24PhCH.sub.2 B34 A2 nHexO B7 A25(4-Cl--Ph)CH.sub.2 B7 A30 CH.sub.2 .dbd.CHCH.sub.2 O B8 A26(4-Me--Ph)CH.sub.2 B7 A31 CHCCH.sub.2 O B9 A27(3,4-Cl.sub.2 --Ph)CH.sub.2 B7 A32 CF.sub.3 O B10 A28(2,4-Me.sub.2 --Ph)CH.sub.2 B7 A33 ClCH.dbd.CHCH.sub.2 O B11 A29PhMeCH B7 A34 MeS B12 A30Ph(Me).sub.2 C B3 A1 MeSO B13 A30Ph(Me).sub.2 C B7 A1 MeSO.sub.2 B14 A30Ph(Me).sub.2 C B3 A2 Me.sub.2 C.dbd.CHCH.sub.2 S B15 A31Ph(Me).sub.2 C B7 A2 Me.sub.2 C.dbd.CHCH.sub.2 SO B16 A32Ph(Me).sub.2 C B8 A2 Me.sub.2 C.dbd.CHCH.sub.2 SO.sub.2 B17 A32Ph(Me).sub.2 C B33 A2 CHCCH.sub.2 S B18 A32Ph(Me).sub.2 C B34 A2 CHCCH.sub.2 SO B19 A1Ph(Me).sub.2 C B35 A2 CHCCH.sub.2 SO.sub.2 B20 A2Ph(Me).sub.2 C B7 A13 CF.sub.3 S B21 A2Ph(Me).sub.2 C B8 A13 CF.sub.3 SO B22 A13Ph(Me).sub.2 C B34 A13 CF.sub.3 SO.sub.2 B23 A13CF.sub.3 B15 A35 ClCH.dbd.CHCH.sub.2 S B24 A1CF.sub.3 CH.sub.2 B6 A36 ClCH.dbd.CHCH.sub.2 SO B25 A1CH.sub.2 .dbd.CMe B6 A1 ClCH.dbd.CHCH.sub.2 SO.sub.2 B26 A2Cl.sub.2 C.dbd.CH B29 A2 ClCCCH.sub.2 S B27 A2BrCCCH.sub.2 SO B28 A1 2-pyridyl H A7ClCCH.sub.2 SO.sub.2 B29 A2 2-pyridyl B7 A71-naphthyl B30 A2 2-pyridyl B8 A72-naphthyl B31 A13 2-pyridyl B15 A7MeC(O) B32 A13 2-pyridyl B34 A7MeC(O)O B33 A1 2-pyridyl H A8CF.sub.3 C(O)O B34 A1 2-pyridyl B7 A82-thienyl B35 A2 2-pyridyl B8 A83-thienyl B36 A2 2-pyridyl B15 A8Me.sub.2 C.dbd.N B37 A1 2-pyridyl B34 A8EtMeC.dbd.N B38 A1 2-pyridyl H A9PhCH.dbd.N B39 A2 2-pyridyl B7 A9PhMeC.dbd.N B40 A2 2-pyridyl B8 A92-pyridyl B7 A1 2-pyridyl B15 A92-pyridyl B8 A1 2-pyridyl B34 A92-pyridyl B15 A1 2-pyridyl CO.sub.2 -iBu A92-pyridyl B34 A1 2-pyridyl H A102-pyridyl B7 A2 2-pyridyl B7 A102-pyridyl B8 A2 2-pyridyl B8 A102-pyridyl B15 A2 2-pyridyl B15 A102-pyridyl B34 A2 2-pyridyl B34 A102-pyridyl CO.sub.2 -iBu A2 2-pyridyl CO.sub.2 -iBu A102-pyridyl B7 A3 2-pyridyl H A112-pyridyl B7 A4 2-pyridyl B7 A112-pyridyl B7 A5 2-pyridyl B8 A112-pyridyl B7 A6 2-pyridyl B15 A112-pyridyl H A12 2-pyridyl B8 A232-pyridyl B7 A12 2-pyridyl B15 A232-pyridyl B8 A12 2-pyridyl B34 A232-pyridyl B15 A12 2-pyridyl B14 A242-pyridyl B34 A12 2-pyridyl B15 A252-pyridyl CO.sub.2 -iBu A12 2-pyridyl B16 A262-pyridyl H A13 2-pyridyl B17 A272-pyridyl B7 A13 2-pyridyl B18 A282-pyridyl B8 A13 2-pyridyl B19 A292-pyridyl B15 A13 2-pyridyl B7 A302-pyridyl B34 A13 2-pyridyl B8 A302-pyridyl CO.sub.2 -iBu A13 2-pyridyl B15 A302-pyridyl H A14 2-pyridyl B20 A312-pyridyl B7 A14 2-pyridyl H A322-pyridyl B16 A14 2-pyridyl B7 A322-pyridyl B17 A14 2-pyridyl B8 A322-pyridyl B7 A15 3-pyridyl B7 A12-pyridyl B8 A16 3-pyridyl B34 A22-pyridyl B9 A17 3-pyridyl CO.sub.2 -iBu A22-pyridyl B10 A18 3-pyridyl B7 A132-pyridyl B11 A19 3-pyridyl B8 A132-pyridyl B12 A20 4-pyridyl B7 A12-pyridyl B13 A21 4-pyridyl B8 A12-pyridyl B7 A22 4-pyridyl B15 A22-pyridyl B8 A22 4-pyridyl B34 A2__________________________________________________________________________
TABLE 11______________________________________ ##STR312## ##STR313## ##STR314## ##STR315## ##STR316##G B Y.sup.1 Y.sup.2 Y.sup.3______________________________________2-Cl H Me Me Me3-Cl B1 Me Cl Me4-Cl B2 Cl Me Me4-Br B3 Cl Cl Me4-I B4 CF.sub.3 Cl Me4-F B5 CF.sub.3 H Me4-Me B6 H CF.sub.3 Me4-Et B7 H Cl Me4-iPr B8 Cl H Me4-nBu B9 H H Me4-iBu B10 OMe Cl Me4-sBu B11 SMe Cl Me4-sBu H Me Me Me4-sBu B16 Me Me Me4-sBu B17 Me Me Me4-sBu B7 Me Cl Me4-sBu B8 Me Cl Me4-sBu B16 Me Cl Me4-sBu B17 Me Cl Me4-sBu B34 Me Cl Me4-sBu B3 CF.sub.3 Cl Me4-sBu B7 CF.sub.3 Cl Me4-sBu B8 CF.sub.3 Cl Me4-sBu B34 CF.sub.3 Cl Me4-sBu B7 Cl Cl Me4-sBu B17 Cl Cl Me4-tBu B12 SCF.sub.3 Cl Me4-tBu H Me Me Me4-tBu B3 Me Cl Me4-tBu B7 Cl Me Me4-tBu B8 Cl Cl Me4-tBu B15 Cl Cl Me4-tBu B16 Cl Cl Me4-tBu B28 Cl Cl Me4-tBu B30 Cl Cl Me4-tBu B34 Cl Cl Me4-tBu CO-nC.sub.8 H.sub.17 Cl Cl Me4-tBu CO-nC.sub.15 H.sub.31 Cl Cl Me4-tBu CO.sub.2 -nHex Cl Cl Me4-tBu CO.sub.2 -nC.sub.10 H.sub.21 Cl Cl Me4-tBu H CN Cl Me4-tBu H CF.sub.3 Cl Me4-tBu B3 CF.sub.3 Cl Me4-tBu B7 CF.sub.3 Cl Me4-tBu B8 CF.sub.3 Cl Me4-tBu B15 CF.sub.3 Cl Me4-tBu B16 CF.sub.3 Cl Me4-tBu B28 CF.sub.3 Cl Me4-tBu B30 CF.sub.3 Cl Me4-tBu B16 Cl Cl Me4-tBu B16 CF.sub.3 Cl Me4-tBu B17 CF.sub.3 Cl Me4-tBu B17 Cl Cl Me4-tBu CO.sub.2 -nC.sub.10 H.sub.21 CF.sub.3 Cl Me4-tBu CH.sub.2 OEt CF.sub.3 Cl Me4-tBu B7 Me Cl Me4-tBu B7 Me Me Me4-tBu B7 CN Cl Me4-tBu B16 CN Cl Me4-tBu B3 CN Cl Me4-tBu 2-(4-tBu--Ph)- CF.sub.3 Cl Me 3,3-Me.sub.2 -cPrC(O)4-tBu B45 CF.sub.3 Cl Me4-tBuCH.sub.2 B3 CF.sub.3 Cl Me4-tBuCH.sub.2 B7 Me Me Me4-tBuCH.sub.2 B16 Me Cl Me4-tBuCH.sub.2 B7 CF.sub.3 Cl Me4-tBuCH.sub.2 B8 CF.sub.3 Cl Me4-tBuCH.sub.2 B7 Cl Cl Me4-Et(Me).sub.2 C H CF.sub.3 Cl Me4-Et(Me).sub.2 C B3 CF.sub.3 Cl Me4-Et(Me).sub.2 C B7 CF.sub.3 Cl Me4-Et(Me).sub.2 C B8 CF.sub.3 Cl Me4-Et(Me).sub.2 C B34 CF.sub.3 Cl Me4-Et(Me).sub.2 C B42 CF.sub.3 Cl Me4-Et(Me).sub.2 C B16 Me Me Me4-Et(Me).sub.2 C B17 Me Me Me4-Et(Me).sub.2 C H Cl Me Me4-Et(Me).sub.2 C B7 Cl Cl Me4-Et(Me).sub.2 C B8 Cl Cl Me4-Et(Me).sub.2 C B7 CF.sub.3 Me Me4-Et(Me).sub.2 C B7 CN Cl Me4-Et(Me).sub.2 C B4 H Cl Me4-Et(Me).sub.2 C B5 Cl H Me4-Et(Me).sub.2 C B6 H H Me4-Et(Me).sub.2 C B3 Cl Cl Me4-Et(Me).sub.2 C B16 Cl Cl Me4-Et(Me).sub.2 C B17 Cl Cl Me4-Et(Me).sub.2 C B24 Cl Cl Me4-nHex B34 CF.sub.3 Cl Me4-nHep B42 CF.sub.3 Cl Me4-nOct B43 Me Me Me4-nNon B43 Me Cl Me4-nDec H Cl Me Me4-(Me).sub.2 (CN)C B7 Cl Cl Me4-PhCH.sub.2 B7 CF.sub.3 Cl Me4-Ph(Me).sub.2 C B7 CF.sub.3 Me Me4-(4-F--Ph)(Me).sub.2 C B7 CN Cl Me4-MeCH.dbd.CH B4 H Cl Me4-MeCC B5 Cl H Me3-CF.sub.3 B6 H H Me4-CF.sub.3 B7 OMe Cl Me4-CF.sub.3 B8 SMe Cl Me4-CF.sub.3 B9 SCF.sub.3 Cl Me4-CF.sub.3 B16 Me Me Me4-CF.sub.3 B17 Me Me Me4-CF.sub.3 B16 Me Cl Me4-CF.sub.3 B17 Cl Me Me4-CF.sub.3 B7 Cl Cl Me4-CF.sub.3 B7 CF.sub.3 Cl Me4-CF.sub.3 B7 CN Cl Me4-CF.sub.3 B3 Cl Cl Me4-CF.sub.3 CH.sub.2 B7 Me Cl Me4-Cl.sub.2 C.dbd.CHCH.sub.2 B8 Cl Me Me4-BrCC B7 Cl Cl Me4-(2,2-F.sub.2)cBuCH.sub.2 B7 CF.sub.3 Cl Me4-(1-Me)cPr B16 CN Cl Me4-cHex B7 Cl Cl Me4-(1-Me)cHex B8 CF.sub.3 Cl Me4-MeO B7 Cl H Me4-iPrO B7 Cl Cl Me4-iPrO B7 CF.sub.3 Cl Me4-iPrO B15 CF.sub.3 Cl Me4-iPrO B7 Me Me Me4-iPrO B16 Me Me Me4-iPrO B17 Me Me Me4-iPrO B23 SCF.sub.3 Cl Me4-tBuO B7 Cl Cl Me4-tBuO B8 Cl Cl Me4-tBuO B7 CF.sub.3 Cl Me4-nHexO B8 CF.sub.3 Cl Me4-nOctO B34 CF.sub.3 Cl Me4-nDecO H CF.sub.3 Cl Me4-CH.sub.2 .dbd.CHCH.sub.2 O B7 CF.sub.3 Cl Me4-CHCCH.sub.2 O B8 CF.sub.3 Cl.sub.3 Me4-CHF.sub.2 O B34 CF.sub.3 Cl Me4-CHF.sub.2 O B7 Me Me Me4-CHF.sub.2 O B35 Me Cl Me4-CHF.sub.2 O B36 Cl Cl Me4-CHF.sub.2 O B7 Cl Cl Me4-CBrF.sub.2 O B8 Cl Cl Me4-CBrF.sub.2 O B34 Cl Cl Me4-CBrF.sub.2 O B40 Me Me Me4-CBrF.sub.2 O B41 Me Cl Me4-CBrF.sub.2 O B42 Cl Me Me4-CBrF.sub.2 O B43 Cl Cl Me4-CBrF.sub.2 O B44 CF.sub.3 Cl Me4-CBrF.sub.2 O COCO.sub.2 Me CF.sub.3 H Me4-CBrF.sub.2 O H H CF.sub.3 Me4-CBrF.sub.2 O B1 H Cl Me4-CF.sub.3 O B2 Cl H Me4-CF.sub.3 O B3 H H Me4-CF.sub.3 O B4 OMe Cl Me4-CF.sub.3 O B5 SMe Cl Me4-CF.sub.3 O B6 SCF.sub.3 Cl Me4-CF.sub.3 O B7 Me Me Me4-CF.sub.3 CH.sub.2 O B8 Me Me Me4-CF.sub.2 .dbd.CHCH.sub.2 CH.sub.2 O B9 Me Cl Me4-CCl.sub.2 .dbd.CHCH.sub.2 O B10 Cl Me Me4-ClCCCH.sub.2 O B11 Cl Cl Me4-MeS B12 CF.sub.3 Cl Me4-sBuS H CF.sub.3 H Me4-EtSO B3 H CF.sub.3 Me4-MeSO.sub.2 H CF.sub.3 Cl Me4-MeSO.sub.2 B3 CF.sub.3 Cl Me4-MeSO.sub.2 B32 CF.sub.3 Cl Me4-MeSO.sub.2 B33 CF.sub.3 Cl Me4-EtSO.sub.2 H CF.sub.3 Cl Me4-EtSO.sub.2 B3 Cl Cl Me4-iPrSO.sub.2 B32 Cl Cl Me4-iPrSO.sub.2 B33 Cl Cl Me4-tBuSO.sub.2 B7 Cl Cl Me4-tBuSO.sub.2 B33 CF.sub.3 Cl Me4-MeCH.dbd.CHCH.sub.2 S B15 H H Me4-CH.sub.2 .dbd.CHCH.sub.2 SO B16 OMe Cl Me4-CH.sub.2 .dbd.CHCH.sub.2 SO.sub.2 B28 SMe Cl Me4-CHCCH.sub.2 S B30 SCF.sub.3 Cl Me4-CHCCH.sub.2 SO B34 Me Me Me4-CHCCH.sub.2 SO.sub.2 CO-nC.sub.8 H.sub.17 Me Me Me4-CHF.sub.2 S H CF.sub.3 Cl Me4-CHF.sub.2 S B7 CF.sub.3 Cl Me4-CHF.sub.2 S B8 CF.sub.3 Cl Me4-CHF.sub.2 S B15 CF.sub.3 Cl Me4-CHF.sub.2 S B29 CF.sub.3 Cl Me4-CHF.sub.2 S H Cl Cl Me4-CHF.sub.2 S B7 Cl Cl Me4-CHF.sub.2 S B15 Cl Cl Me4-CBrF.sub.2 S B7 Cl Cl Me4-CBrF.sub.2 S B15 Cl Cl Me4-CBrF.sub.2 S B30 Cl Cl Me4-CBrF.sub.2 S B43 Cl Cl Me4-CBrF.sub.2 S CO-nC.sub.15 H.sub.31 Me Cl Me4-CBrF.sub.2 S CO.sub.2 -nHex CF.sub.3 Cl Me4-CBrF.sub.2 S H CF.sub.3 Cl Me4-CBrF.sub.2 S B7 CF.sub.3 Cl Me4-CBrF.sub.2 S B8 CF.sub.3 Cl Me4-CBrF.sub.2 S B15 CF.sub.3 Cl Me4-CBrF.sub.2 S B28 CF.sub.3 Cl Me4-CBrF.sub.2 S B34 CF.sub.3 Cl Me4-CBrF.sub.2 S B7 Me Cl Me4-CF.sub.3 S CO.sub.2 -nC.sub.10 H.sub.21 Cl Cl Me4-CF.sub.3 S H Cl Cl Me4-CF.sub.3 S B3 Cl Cl Me4-CF.sub.3 S B7 Cl Cl Me4-CF.sub.3 S B8 Cl Cl Me4-CF.sub.3 S B15 Cl Cl Me4-CF.sub.3 S H CF.sub.3 Cl Me4-CF.sub.3 S B7 CF.sub.3 Cl Me4-CF.sub.3 S B8 CF.sub.3 Cl Me4-CF.sub.3 S B15 CF.sub.3 Cl Me4-CF.sub.3 S B34 CF.sub.3 Cl Me4-CF.sub.3 S CO.sub.2 -nC.sub.12 H.sub.25 CF.sub.3 Cl Me4-CF.sub.3 S CO-nC.sub.15 H.sub.31 CF.sub.3 Cl Me4-CF.sub.3 S CO-nC.sub.16 H.sub.33 Me Me Me4-CF.sub.3 S CO-nC.sub.17 H.sub.35 Me Cl Me4-CF.sub.3 CH.sub.2 S CO-nC.sub.18 H.sub.37 CF.sub.3 Cl Me4-CHF.sub.2 CF.sub.2 S CO-nC.sub.19 H.sub.39 CF.sub.3 H Me4-CHF.sub.2 SO CO-nC.sub.20 H.sub.41 H CF.sub.3 Me4-CBrF.sub.2 SO H H Cl Me4-CBrF.sub.2 SO B3 CF.sub.3 Cl Me4-CBrF.sub.2 SO B7 CF.sub.3 Cl Me4-CBrF.sub.2 SO B24 CF.sub.3 Cl Me4-CBrF.sub.2 SO B32 CF.sub.3 Cl Me4-CBrF.sub.2 SO B33 CF.sub.3 Cl Me4-CF.sub.3 SO H Cl Cl Me4-CF.sub.3 SO B3 Cl Cl Me4-CF.sub.3 SO B7 Cl Cl Me4-CF.sub.3 SO B33 Cl H Me4-CF.sub.3 CH.sub.2 SO.sub.2 B15 H H Me4-CHF.sub.2 CF.sub.2 SO.sub.2 B16 OMe Cl Me4-CHF.sub.2 SO.sub.2 B28 SMe Cl Me4-CHF.sub.2 SO.sub.2 B7 CF.sub.3 Cl Me4-CHF.sub.2 SO.sub.2 B24 CF.sub.3 Cl Me4-CHF.sub.2 SO.sub.2 B32 CF.sub.3 Cl Me4-CHF.sub.2 SO.sub.2 B33 CF.sub.3 Cl Me4-CHF.sub.2 SO.sub.2 H Cl Cl Me4-CHF.sub.2 SO.sub.2 B3 Cl Cl Me4-CHF.sub.2 SO.sub.2 B7 Cl Cl Me4-CHF.sub.2 SO.sub.2 B33 Cl H Me4-CBrF.sub.2 SO.sub.2 H SCF.sub.3 Cl Me4-CBrF.sub.2 SO.sub.2 B2 Cl Cl Me4-CBrF.sub.2 SO.sub.2 B3 Cl Cl Me4-CBrF.sub.2 SO.sub.2 B18 Cl Cl Me4-CBrF.sub.2 SO.sub.2 B19 Cl Cl Me4-CBrF.sub.2 SO.sub.2 B33 Cl Cl Me4-CBrF.sub.2 SO.sub.2 H CF.sub.3 Cl Me4-CBrF.sub.2 SO.sub.2 B3 CF.sub.3 Cl Me4-CBrF.sub.2 SO.sub.2 B7 CF.sub.3 Cl Me4-CBrF.sub.2 SO.sub.2 B20 CF.sub.3 Cl Me4-CBrF.sub.2 SO.sub.2 B32 CF.sub.3 Cl Me4-CBrF.sub.2 SO.sub.2 B33 CF.sub.3 Cl Me4-CBrF.sub.2 SO.sub.2 B37 CF.sub.3 Cl Me4-CBrF.sub.2 SO.sub.2 B7 Me Me Me4-CBrF.sub.2 SO.sub.2 B15 Me Me Me4-CBrF.sub.2 SO.sub.2 B17 Me Me Me4-CBrF.sub.2 SO.sub.2 B7 Me Cl Me4-CBrF.sub.2 SO.sub.2 B16 Me Cl Me4-CF.sub.3 SO.sub.2 B16 Me Me Me4-CF.sub.3 SO.sub.2 B7 Cl Cl Me4-CF.sub.3 SO.sub.2 B15 Cl Cl Me4-CF.sub.3 SO.sub.2 B3 CF.sub.3 Cl Me4-CF.sub.3 SO.sub.2 B7 CF.sub.3 Cl Me4-CF.sub.3 SO.sub.2 B15 Me Me Me4-CF.sub.3 SO.sub.2 B7 Me Cl Me4-CF.sub.3 SO.sub.2 B8 Me Cl Me4-Cl.sub.2 C.dbd.CHCH.sub.2 S B16 Me Me Me4-Cl.sub.2 C.dbd.CHCH.sub.2 SO B17 Me Cl Me4-Cl.sub.2 C.dbd.CHCH.sub.2 SO.sub.2 B17 Cl Me Me4-CBrCCH.sub.2 S CO.sub.2 -nC.sub.10 H.sub.21 Cl Cl Me4-CBrCCH.sub.2 SO B33 CF.sub.3 Cl Me4-CBrCCH.sub.2 SO.sub.2 B7 CF.sub.3 H Me4-CHO B7 H CF.sub.3 Me4-NO.sub.2 B8 H Cl Me4-CN B16 Cl H Me4-(Me).sub.2 N B3 H H Me4-Me(MeCO)N B7 OMe Cl Me4-PhMeN B8 SMe Cl Me4-PhCH.sub.2 (MeCO)N B15 SCF.sub.3 Cl Me4-(1-naphthyl) B16 Me Me Me4-(2-naphthyl) B28 Me Me Me4-(2-Cl--Ph)CH.sub.2 O B30 Me Cl Me4-(3-Cl--Ph)CH.sub.2 O B34 Cl Me Me4-(4-Cl--Ph)CH.sub.2 O B7 CF.sub.3 Cl Me4-(4-Cl--Ph)CH.sub.2 O B7 Cl Cl Me4-(4-Cl--Ph)CH.sub.2 O B37 Cl Cl Me4-(4-F--Ph)CH.sub.2 O B42 CF.sub.3 Cl Me4-(2-Me--Ph)CH.sub.2 O B43 CF.sub.3 H Me4-(4-Me--Ph)CH.sub.2 O B43 H CF.sub.3 Me4-(4-Et--Ph)CH.sub.2 O H H Cl Me3-(2,4-Cl.sub.2 --Ph)CH.sub.2 O B7 Cl H Me4-(3,4-Cl.sub.2 --Ph)CH.sub.2 O B7 H H Me4-(2,5-Me.sub.2 --Ph)CH.sub.2 O B7 OMe Cl Me4-(2,3,4,5,6-F.sub.5 --Ph)CH.sub.2 O B7 SMe Cl Me4-MeOC(O) B4 SCF.sub.3 Cl Me4-EtOC(O) B5 Me Me Me4-nPrOC(O) B6 Me Me Me4-iPrOC(O) B7 Me Cl Me4-iBuOC(O) B8 Cl Me Me4-tBuOC(O) B9 Cl Cl Me4-tBuCH.sub.2 OC(O) B7 Cl Cl Me4-tBuCH.sub.2 OC(O) B15 Cl Cl Me4-tBuCH.sub.2 OC(O) B34 Cl Cl Me4-tBuCH.sub.2 OC(O) B7 CF.sub.3 Cl Me4-tBuCH.sub.2 OC(O) B15 CF.sub.3 Cl Me4-tBuCH.sub.2 OC(O) B34 CF.sub.3 Cl Me4-tBuCH.sub.2 OC(O) B10 CF.sub.3 Cl Me4-Et(Me).sub.2 COC(O) B11 CF.sub.3 H Me4-nHexOC(O) B7 H CF.sub.3 Me4-MeOCH.sub.2 B8 H Cl Me4-EtOCH.sub.2 B7 Cl H Me4-iPrOCH.sub.2 B7 H H Me4-MeC(O) B16 OMe Cl Me4-EtC(O) B7 SMe Cl Me4-iPrC(O) B8 SCF.sub.3 Cl Me4-tBuC(O) H Cl Cl Me4-tBuC(O) B3 Cl Cl Me4-tBuC(O) B7 Cl Cl Me4-tBuC(O) B3 CF.sub.3 Cl Me4-tBuC(O) B7 CF.sub.3 Cl Me4-tBuC(O) B15 CF.sub.3 Cl Me4-tBuC(O) B7 Me Me Me4-tBuC(O) B17 Me Me Me4-tBuC(O) B16 Me Cl Me4-CF.sub.3 C(O) B7 Me Me Me4-CF.sub.3 CF.sub.2 C(O) B8 Me Cl Me4-CF.sub.2 CF.sub.2 CF.sub.2 C(O) B22 Cl Me Me4-MeC(O)O B23 Cl Cl Me4-iPrC(O)O B7 CF.sub.3 Cl Me4-tBuC(O)O B8 CF.sub.3 H Me4-CF.sub.3 C(O)O B7 H CF.sub.3 Me4-CF.sub.2 CF.sub.2 CF.sub.2 C(O)O B8 H Cl Me4-Me.sub.2 NC(O)O B34 Cl H Me4-Et.sub.2 NC(O)O H H H Me4-(nPr).sub.2 NC(O)O B7 OMe Cl Me3-Ph B8 SMe Cl Me4-Ph B34 SCF.sub.3 Cl Me4-(4-F--Ph) B7 Cl Cl Me4-(4-F--Ph) B7 CF.sub.3 Cl Me3-PhO B7 Cl Cl Me3-PhO B15 CF.sub.3 Cl Me4-PhO B7 Me Me Me4-(4-F--Ph)O B35 Me Cl Me4-(4-Cl--Ph)O B36 Cl Me Me4-(4-Br--Ph)O B7 Cl Cl Me4-(4-Me--Ph) B8 CF.sub.3 Cl Me4-(2-Cl--Ph)O B34 CF.sub.3 H Me4-(2-F--Ph)O B40 H CF.sub.3 Me4-(3-Cl--Ph)O B41 H Cl Me4-(4-Cl--Ph)O B42 Cl H Me4-(2,4-Cl.sub.2 --Ph)O B43 H H Me4-(3,4-Cl.sub.2 --Ph)O B44 OMe Cl Me4-(3,4,5-Cl.sub.3 --Ph)O COCO.sub.2 Me SMe Cl Me4-(2-Me--Ph)O H SCF.sub.3 Cl Me4-(4-Me--Ph)O B1 Me Me Me4-(3-Cl-4-Me--Ph)O B2 H CF.sub.3 Me4-(2-pyridyl) B3 H Cl Me4-(5-CF.sub.3 -pyridin-2-yl) B4 Cl H Me4-(2-pyridyl)O B7 Cl Cl Me4-(2-pyridyl)O B15 Cl Cl Me4-(2-pyridyl)O B7 CF.sub.3 Cl Me4-(2-pyridyl)O B8 CF.sub.3 Cl Me4-(2-pyridyl)O B34 CF.sub.3 Cl Me4-(2-pyridyl)O B5 Cl Cl Me4-(5-CF.sub.3 -pyridin-2-yl)O B7 Cl Cl Me4-(5-CF.sub.3 -pyridin-2-yl)O B8 Cl Cl Me4-(5-CF.sub.3 -pyridin-2-yl)O B15 CF.sub.3 Cl Me4-(5-CF.sub.3 -pyridin-2-yl)O B7 CF.sub.3 Cl Me4-(5-CF.sub.3 -pyridin-2-yl)O B15 CF.sub.3 Cl Me4-(5-CF.sub.3 -pyridin-2-yl)O B34 Me Cl Me4-(3-Cl-5-CF.sub.3 -pyridin-2-yl) B7 Cl Cl Me4-(3-Cl-5-CF.sub.3 -pyridin-2-yl) B15 Cl Cl Me4-(3-Cl-5-CF.sub.3 -pyridin-2-yl) B34 Cl Cl Me4-(3-Cl-5-CF.sub.3 -pyridin-2-yl) B7 CF.sub.3 Cl Me4-(3-Cl-5-CF.sub.3 -pyridin-2-yl) B15 CF.sub.3 Cl Me4-(3-Cl-5-CF.sub.3 -pyridin-2-yl) B17 CF.sub.3 Cl Me4-(3-Cl-5-CF.sub.3 -pyridin-2-yl) H Cl Cl Me4-(5-Cl-thiophen-2-yl) B8 Cl Cl Me3-OCH.sub.2 O-4 B9 Cl Cl Me4-OCF.sub.2 O-4 B10 CF.sub.3 Cl Me4-MeCH.dbd.N B11 CF.sub.3 Cl Me4-Me.sub.2 C.dbd.N B12 CF.sub.3 Cl Me4-MeEtC.dbd.N H Cl Cl Me4-PhCH.dbd.N B3 Cl Cl Me4-PhMeC.dbd.N B7 Cl Cl Me4-PhCH.sub.2 CH.dbd.N B8 CF.sub.3 Cl Me4-cC.sub.6 H.sub.10 .dbd.N B15 CF.sub.3 Cl Me3-CH.sub.2 CH.sub.2 CH.sub.2 -4 B16 CF.sub.3 Cl Me3-CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 -4 B28 Cl Cl Me4-PhC(O) H Cl Cl Me4-PhC(O) B7 Cl Cl Me4-PhC(O) B7 Cl Cl Me4-PhC(O) B33 CF.sub.3 Cl Me4-(2-Cl--Ph)C(O) B7 CF.sub.3 Cl Me4-(4-F--Ph)C(O) H CF.sub.3 Cl Me4-(4-Cl--Ph)C(O) B7 Cl Cl Me4-(4-Cl--Ph)C(O) B15 Cl Cl Me4-(4-Cl--Ph)C(O) B34 Cl Cl Me4-(4-Me--Ph)C(O) B3 CF.sub.3 Cl Me4-(4-Me--Ph)C(O) B16 CF.sub.3 Cl Me4-(3,4-Cl.sub.2 --Ph)C(O) B45 CF.sub.3 Cl Me3,4-Cl.sub.2 B15 Cl Cl Me3-Cl-4-F B7 Cl Cl Me2,6-F.sub.2 B15 CF.sub.3 Cl Me3-Cl-4-CF.sub.3 B7 CF.sub.3 Cl Me4-tBu-3-Cl B7 Cl Cl Me4-tBu-3-Cl B15 CF.sub.3 Cl Me4-tBuCH.sub.2 -3-Cl B7 Cl Cl Me4-nHep-3-Cl B15 CF.sub.3 Cl Me3-Cl-4-iPrO B7 Cl Cl Me3-Cl-4-iPrO B7 CF.sub.3 Cl Me3-Cl-4-nHepO B15 CF.sub.3 Cl Me3-Cl-4-(3,4-Cl.sub.2 --PhCH.sub.2)O H CF.sub.3 Cl Me3-Cl-4-PhCH.sub.2 O B7 CF.sub.3 Cl Me3,4-(MeO).sub.2 B16 CF.sub.3 Cl Me4-MeO-3-Me B17 CF.sub.3 Cl Me4-OH-3,5-(tBu).sub.2 B3 CF.sub.3 Cl Me3,4,5-Cl.sub.3 B15 CF.sub.3 Cl Me2,6-Cl.sub.2 -4-CF.sub.3 B7 CF.sub.3 Cl Me2,6-F.sub.2 -4-CF.sub.3 B15 Cl Cl Me2,6-F.sub.2 -4-CF.sub.3 O B7 CF.sub.3 Cl Me3,5-Cl.sub.2 -4-tBu B7 Cl Cl Me3,5-Cl.sub.2 -4-tBuCH.sub.2 B15 CF.sub.3 Cl Me3,5-Cl.sub.2 -4-nDec B7 Cl Cl Me3,5-Cl.sub.2 -4-PhCH.sub.2 O B15 CF.sub.3 Cl Me2,3,5,6-F.sub.4 -4-Me B3 CF.sub.3 Cl Me2,3,4,5,6-F.sub.5 B33 CF.sub.3 Cl Me______________________________________
TABLE 12______________________________________ ##STR317## ##STR318## ##STR319## ##STR320## ##STR321## ##STR322## ##STR323## ##STR324## ##STR325## ##STR326## ##STR327##G B Y.sup.1 Y.sup.2______________________________________2-Cl H Me Me3-Cl B1 H H4-Cl B2 Me H4-Br B3 H Me4-I B4 Me Me4-F B5 CF.sub.3 Me4-Me B6 Cl Me4-Et B7 H Me4-iPr B8 Cl Me4-nBu B9 H Me4-iBu B10 OMe Me4-sBu B11 SMe Me4-sBu H Me Me4-sBu B16 Et Me4-sBu B17 Cl Me4-sBu B7 Cl Cl4-sBu B8 CF.sub.3 Me4-sBu B16 Me CF.sub.34-sBu B17 Me Me4-sBu B34 CF.sub.3 Me4-sBu B3 CF.sub.3 Me4-sBu B7 CF.sub.3 Me4-sBu B8 Cl Me4-sBu B34 Me Cl4-sBu B7 H H4-sBu B17 CF.sub.3 Me4-tBu B12 SCF.sub.3 Me4-tBu H Me Me4-tBu B3 Me Me4-tBu B7 Me Me4-tBu B8 Et Me4-tBu B15 Me nPr4-tBu B16 OMe OMe4-tBu B28 Cl Cl4-tBu B30 OCHF.sub.2 Me4-tBu B34 CF.sub.3 CF.sub.34-tBu CO-nC.sub.8 H.sub.17 H H4-tBu CO-nC.sub.15 H.sub.31 Cl Cl4-tBu CO.sub.2 -nHex Me Me4-tBu CO.sub.2 -nC.sub.10 H.sub.21 Me Me4-tBu H CN Me4-tBu H CF.sub.3 Me4-tBu B3 CF.sub.3 Me4-tBu B7 CF.sub.3 Me4-tBu B8 CF.sub.3 Me4-tBu B15 CF.sub.3 Me4-tBu B16 CF.sub.3 Me4-tBu B28 CF.sub.3 Me4-tBu B30 CF.sub.3 Me4-tBu B16 Cl Cl4-tBu B16 CF.sub.3 Me4-tBu B17 CF.sub.3 Me4-tBu B17 Me Me4-tBu CO.sub.2 -nC.sub.10 H.sub.21 CF.sub.3 Me4-tBu CH.sub.2 OEt CF.sub.3 Me4-tBu B7 Me CF.sub.34-tBu B7 Cl Cl4-tBu B7 CN Me4-tBu B16 CN Me4-tBu B3 CN Me4-tBu 2-(4-tBu--Ph)- CF.sub.3 Me 3,3-Me.sub.2 -cPrC(O)4-tBu B45 CF.sub.3 Me4-tBuCH.sub.2 B3 CF.sub.3 Me4-tBuCH.sub.2 B7 Me Me4-tBuCH.sub.2 B16 Me Me4-tBuCH.sub.2 B7 CF.sub.3 Me4-tBuCH.sub.2 B8 CF.sub.3 Me4-tBuCH.sub.2 B7 Cl Me4-Et(Me).sub.2 C H CF.sub.3 Me4-Et(Me).sub.2 C B3 CF.sub.3 Me4-Et(Me).sub.2 C B7 CF.sub.3 Me4-Et(Me).sub.2 C B8 CF.sub.3 Me4-Et(Me).sub.2 C B34 CF.sub.3 Me4-Et(Me).sub.2 C B42 CF.sub.3 Me4-Et(Me).sub.2 C B16 CF.sub.3 Me4-Et(Me).sub.2 C B17 CF.sub.3 Me4-Et(Me).sub.2 C H Cl Me4-Et(Me).sub.2 C B7 Cl Me4-Et(Me).sub.2 C B8 Cl Me4-Et(Me).sub.2 C B7 Me CF.sub.34-Et(Me).sub.2 C B7 CN Me4-Et(Me).sub.2 C B4 H Me4-Et(Me).sub.2 C B5 Me Me4-Et(Me).sub.2 C B6 Me Me4-Et(Me).sub.2 C B3 Me Cl4-Et(Me).sub.2 C B16 Me Cl4-Et(Me).sub.2 C B17 Me Cl4-Et(Me).sub.2 C B24 Me Cl4-nHex B34 CF.sub.3 Me4-nHep B42 CF.sub.3 Me4-nOct B43 Me Me4-nNon B43 Me Me4-nDec H Cl Me4-(Me).sub.2 (CN)C B7 Cl Me4-PhCH.sub.2 B7 CF.sub.3 Me4-Ph(Me).sub.2 C B7 CF.sub.3 Me4-(4-F--Ph)(Me).sub.2 C B7 CN Me4-MeCH.dbd.CH B4 H Me4-MeCC B5 Cl Me3-CF.sub.3 B6 H Me4-CF.sub.3 B7 OMe Me4-CF.sub.3 B8 SMe Me4-CF.sub.3 B9 SCF.sub.3 Me4-CF.sub.3 B16 Me Me4-CF.sub.3 B17 Me Me4-CF.sub.3 B16 Me Me4-CF.sub.3 B17 Cl Me4-CF.sub.3 B7 Cl Me4-CF.sub.3 B7 CF.sub.3 Me4-CF.sub.3 B7 Me Me4-CF.sub.3 B3 Cl Me4-CF.sub.3 CH.sub.2 B7 Me Me4-Cl.sub.2 C.dbd.CHCH.sub.2 B8 Cl Me4-BrCC B7 Cl Me4-(2,2-F.sub.2)cBuCH.sub.2 B7 CF.sub.3 Me4-(1-Me)cPr B16 CN Me4-cHex B7 CF.sub.3 Me4-(1-Me)cHex B8 CF.sub.3 Me4-MeO B7 CF.sub.3 Me4-iPrO B7 Cl Me4-iPrO B7 CF.sub.3 Me4-iPrO B15 CF.sub.3 Me4-iPrO B7 Me Me4-iPrO B16 Me Me4-iPrO B17 Me Me4-iPrO B23 SCF.sub.3 Me4-tBuO B7 Me Me4-tBuO B8 CF.sub.3 Me4-tBuO B7 CF.sub.3 Me4-nHexO B8 CF.sub.3 Me4-nOctO B34 CF.sub.3 Me4-nDecO H CF.sub.3 Me4-CH.sub.2 .dbd.CHCH.sub.2 O B7 CF.sub.3 Me4-CHCCH.sub.2 O B8 CF.sub.3 Me4-CHF.sub.2 O B34 CF.sub.3 Me4-CHF.sub.2 O B7 Et Me4-CHF.sub.2 O B35 Me Me4-CHF.sub.2 O B36 Cl Me4-CHF.sub.2 O B7 CF.sub.3 Me4-CBrF.sub.2 O B8 Cl Me4-CBrF.sub.2 O B34 Cl Me4-CBrF.sub.2 O B40 Me Me4-CBrF.sub.2 O B41 Me Me4-CBrF.sub.2 O B42 Cl Me4-CBrF.sub.2 O B7 CF.sub.3 Me4-CBrF.sub.2 O B8 CF.sub.3 Me4-CBrF.sub.2 O COCO.sub.2 Me CF.sub.3 Me4-CBrF.sub.2 O H H Me4-CBrF.sub.2 O B1 CF.sub.3 Me4-CF.sub.3 O B2 Cl Me4-CF.sub.3 O B3 H Me4-CF.sub.3 O B4 OMe Me4-CF.sub.3 O B5 SMe Me4-CF.sub.3 O B6 SCF.sub.3 Me4-CF.sub.3 O B7 CF.sub.3 Me4-CF.sub.3 CH.sub.2 O B8 Me Me4-CF.sub.2 .dbd.CHCH.sub.2 CH.sub.2 O B9 Me Me4-CCl.sub.2 .dbd.CHCH.sub.2 O B10 Cl Me4-ClCCCH.sub.2 O B11 Cl Me4-MeS B12 CF.sub.3 Me4-sBuS H CF.sub.3 Me4-EtSO B3 H Me4-MeSO.sub.2 H CF.sub.3 Me4-MeSO.sub.2 B3 CF.sub.3 Me4-MeSO.sub.2 B32 CF.sub.3 Me4-MeSO.sub.2 B33 CF.sub.3 Me4-EtSO.sub.2 H CF.sub.3 Me4-EtSO.sub.2 B3 Et Me4-iPrSO.sub.2 B32 CF.sub.3 Me4-iPrSO.sub.2 B33 CF.sub.3 Me4-tBuSO.sub.2 B7 CF.sub.3 Me4-tBuSO.sub.2 B33 CF.sub.3 Me4-MeCH.dbd.CHCH.sub.2 S B15 H Me4-CH.sub.2 .dbd.CHCH.sub.2 SO B16 OMe Me4-CH.sub.2 .dbd.CHCH.sub.2 SO.sub.2 B28 SMe Me4-CHCCH.sub.2 S B30 SCF.sub.3 Me4-CHCCH.sub.2 SO B34 Me Me4-CHCCH.sub.2 SO.sub.2 CO-nC.sub.8 H.sub.17 Me Me4-CHF.sub.2 S H CF.sub.3 Me4-CHF.sub.2 S B7 CF.sub.3 Me4-CHF.sub.2 S B8 CF.sub.3 Me4-CHF.sub.2 S B15 CF.sub.3 Me4-CHF.sub.2 S B29 CF.sub.3 Me4-CHF.sub.2 S H Me Me4-CHF.sub.2 S B7 Me Me4-CHF.sub.2 S B15 Me Me4-CBrF.sub.2 S B7 Me CF.sub.34-CBrF.sub.2 S B15 Me CF.sub.34-CBrF.sub.2 S B30 Me CF.sub.34-CBrF.sub.2 S B43 Me CF.sub.34-CBrF.sub.2 S CO-nC.sub.15 H.sub.31 nPr Me4-CBrF.sub.2 S CO.sub.2 -nHex CF.sub.3 Me4-CBrF.sub.2 S H CF.sub.3 Me4-CBrF.sub.2 S B7 CF.sub.3 Me4-CBrF.sub.2 S B8 CF.sub.3 Me4-CBrF.sub.2 S B15 CF.sub.3 Me4-CBrF.sub.2 S B28 CF.sub.3 Me4-CBrF.sub.2 S B34 CF.sub.3 Me4-CBrF.sub.2 S B7 Me Me4-CF.sub.3 S CO.sub.2 -nC.sub.10 H.sub.21 Cl Me4-CF.sub.3 S H Me Me4-CF.sub.3 S B3 Me Me4-CF.sub.3 S B7 Me Me4-CF.sub.3 S B8 Me Me4-CF.sub.3 S B15 Me Me4-CF.sub.3 S H CF.sub.3 Me4-CF.sub.3 S B7 CF.sub.3 Me4-CF.sub.3 S B8 CF.sub.3 Me4-CF.sub.3 S B15 CF.sub.3 Me4-CF.sub.3 S B34 CF.sub.3 Me4-CF.sub.3 S CO.sub.2 -nC.sub.12 H.sub.25 CF.sub.3 Me4-CF.sub.3 S CO-nC.sub.15 H.sub.31 CF.sub.3 Me4-CF.sub.3 S CO-nC.sub.16 H.sub.33 Me Me4-CF.sub.3 S CO-nC.sub.17 H.sub.35 Me Me4-CF.sub.3 CH.sub.2 S CO-nC.sub.18 H.sub.37 CF.sub.3 Me4-CHF.sub.2 CF.sub.2 S CO-nC.sub.19 H.sub.39 CF.sub.3 Me4-CHF.sub.2 SO CO-nC.sub.20 H.sub.41 Cl Cl4-CBrF.sub.2 SO H H Me4-CBrF.sub.2 SO B3 CF.sub.3 Me4-CBrF.sub.2 SO B7 CF.sub.3 Me4-CBrF.sub.2 SO B24 CF.sub.3 Me4-CBrF.sub.2 SO B32 CF.sub.3 Me4-CBrF.sub.2 SO B33 CF.sub.3 Me4-CF.sub.3 SO H Me Me4-CF.sub.3 SO B3 Me Me4-CF.sub.3 SO B7 Me Me4-CF.sub.3 SO B33 Me Me4-CF.sub.3 CH.sub.2 SO.sub.2 B15 H Me4-CHF.sub.2 CF.sub.2 SO.sub.2 B16 OMe Me4-CHF.sub.2 SO.sub.2 B28 SMe Me4-CHF.sub.2 SO.sub.2 B7 CF.sub.3 Me4-CHF.sub.2 SO.sub.2 B24 CF.sub.3 Me4-CHF.sub.2 SO.sub.2 B32 CF.sub.3 Me4-CHF.sub.2 SO.sub.2 B33 CF.sub.3 Me4-CHF.sub.2 SO.sub.2 H Me Me4-CHF.sub.2 SO.sub.2 B3 Me Me4-CHF.sub.2 SO.sub.2 B7 Me Me4-CHF.sub.2 SO.sub.2 B33 Me Me4-CBrF.sub.2 SO.sub.2 H SCF.sub.3 Me4-CBrF.sub.2 SO.sub.2 B2 Me Me4-CBrF.sub.2 SO.sub.2 B3 Me Me4-CBrF.sub.2 SO.sub.2 B18 Me Me4-CBrF.sub.2 SO.sub.2 B19 Me Me4-CBrF.sub.2 SO.sub.2 B33 Me Me4-CBrF.sub.2 SO.sub.2 H CF.sub.3 Me4-CBrF.sub.2 SO.sub.2 B3 CF.sub.3 Me4-CBrF.sub.2 SO.sub.2 B7 CF.sub.3 Me4-CBrF.sub.2 SO.sub.2 B20 CF.sub.3 Me4-CBrF.sub.2 SO.sub.2 B32 CF.sub.3 Me4-CBrF.sub.2 SO.sub.2 B33 CF.sub.3 Me4-CBrF.sub.2 SO.sub.2 B37 CF.sub.3 Me4-CBrF.sub.2 SO.sub.2 B7 Me CF.sub.34-CBrF.sub.2 SO.sub.2 B15 Me CF.sub.34-CBrF.sub.2 SO.sub.2 B17 Me CF.sub.34-CBrF.sub.2 SO.sub.2 B7 Me CF.sub.34-CBrF.sub.2 SO.sub.2 B16 Me CF.sub.34-CF.sub.3 SO.sub.2 B16 Me Me4-CF.sub.3 SO.sub.2 B7 Cl Me4-CF.sub.3 SO.sub.2 B15 Cl Cl4-CF.sub.3 SO.sub.2 B3 CF.sub.3 Me4-CF.sub.3 SO.sub.2 B7 CF.sub.3 Me4-CF.sub.3 SO.sub.2 B15 Me Me4-CF.sub.3 SO.sub.2 B7 Me Me4-CF.sub.3 SO.sub.2 B8 Me Me4-Cl.sub.2 C.dbd.CHCH.sub.2 S B16 Me Me4-Cl.sub.2 C.dbd.CHCH.sub.2 SO B17 Me Me4-Cl.sub.2 C.dbd.CHCH.sub.2 SO.sub.2 B17 Cl Me4-CBrCCH.sub.2 S CO.sub.2 -nC.sub.10 H.sub.21 Cl Me4-CBrCCH.sub.2 SO B33 CF.sub.3 Me4-CBrCCH.sub.2 SO.sub.2 B7 CF.sub.3 Me4-CHO B7 H Me4-NO.sub.2 B8 H Me4-CN B16 Cl Me4-(Me).sub.2 N B3 H Me4-Me(MeCO)N B7 OMe Me4-PhMeN B8 SMe Me4-PhCH.sub.2 (MeCO)N B15 SCF.sub.3 Me4-(1-naphthyl) B16 Me Me4-(2-naphthyl) B28 Me Me4-(2-Cl--Ph)CH.sub.2 O B30 Me Me4-(3-Cl--Ph)CH.sub.2 O B34 Cl Me4-(4-Cl--Ph)CH.sub.2 O B7 CF.sub.3 Me4-(4-Cl--Ph)CH.sub.2 O B7 Cl Me4-(4-Cl--Ph)CH.sub.2 O B37 Cl Me4-(4-F--Ph)CH.sub.2 O B42 CF.sub.3 Me4-(2-Me--Ph)CH.sub.2 O B43 CF.sub.3 Me4-(4-Me--Ph)CH.sub.2 O B43 CF.sub.3 Me4-(4-Et--Ph)CH.sub.2 O H CF.sub.3 Me3-(2,4-Cl.sub.2 --Ph)CH.sub.2 O B7 CF.sub.3 Me4-(3,4-Cl.sub.2 --Ph)CH.sub.2 O B7 H Me4-(2,5-Me.sub.2 --Ph)CH.sub.2 O B7 OMe Me4-(2,3,4,5,6-F.sub.5 --Ph)CH.sub.2 O B7 SMe Me4-MeOC(O) B4 SCF.sub.3 Me4-EtOC(O) B5 Me Me4-nPrOC(O) B6 Me Me4-iPrOC(O) B7 Me Me4-tBuOC(O) B7 Me Me4-tBuOC(O) B3 CF.sub.3 Me4-tBuOC(O) B5 CF.sub.3 Me4-tBuOC(O) B33 CF.sub.3 Me4-tBuOC(O) H CF.sub.3 Me4-tBuOC(O) B7 CF.sub.3 Me4-tBuOC(O) B8 CF.sub.3 Me4-tBuOC(O) B34 CF.sub.3 Me4-tBuCH.sub.2 OC(O) B10 CF.sub.3 Me4-Et(Me).sub.2 COC(O) B11 CF.sub.3 Me4-nHexOC(O) B7 H Me4-MeOCH.sub.2 B8 H Me4-EtOCH.sub.2 B7 Cl Me4-iPrOCH.sub.2 B7 H Me4-MeC(O) B16 OMe Me4-EtC(O) B7 SMe Me4-iPrC(O) B8 SCF.sub.3 Me4-tBuC(O) H Cl Cl4-tBuC(O) B3 Cl Cl4-tBuC(O) B7 Cl Cl4-tBuC(O) B3 CF.sub.3 Me4-tBuC(O) B7 CF.sub.3 Me4-tBuC(O) B15 CF.sub.3 Me4-tBuC(O) B7 Me Me4-tBuC(O) B17 Me Me4-tBuC(O) B16 Me Me4-CF.sub.3 C(O) B33 Me Me4-CF.sub.3 CF.sub.2 C(O) B8 Me Me4-CF.sub.2 CF.sub.2 CF.sub.2 C(O) B22 Cl Me4-MeC(O)O B23 Cl Me4-iPrC(O)O B7 CF.sub.3 Me4-tBuC(O)O B8 CF.sub.3 Me4-CF.sub.3 C(O)O B7 H Me4-CF.sub.2 CF.sub.2 CF.sub.2 C(O)O B8 H Me4-Me.sub.2 NC(O)O B34 Cl Me4-Et.sub.2 NC(O)O H H Me4-(nPr).sub.2 NC(O)O B7 OMe Me3-Ph B8 SMe Me4-Ph B34 SCF.sub.3 Me4-(4-F--Ph) B7 Et Me4-(4-F--Ph) B7 CF.sub.3 Me3-PhO B7 Me Me3-PhO B15 CF.sub.3 Me4-PhO B7 Me Me4-(4-F--Ph)O B35 Me Me4-(4-Cl--Ph)O B36 Et Me4-(4-Br--Ph)O B7 CF.sub.3 Me4-(4-Me--Ph) B8 CF.sub.3 Me4-(2-Cl--Ph)O B34 CF.sub.3 Me4-(2-F--Ph)O B40 H Me4-(3-Cl--Ph)O B41 H Me4-(4-Cl--Ph)O B42 Cl Me4-(2,4-Cl.sub.2 --Ph)O B43 H Me4-(3,4-Cl.sub.2 --Ph)O B44 OMe Me4-(3,4,5-Cl.sub.3 --Ph)O COCO.sub.2 Me SMe Me4-(2-Me--Ph)O H SCF.sub.3 Me4-(4-Me--Ph)O B1 Me Me4-(3-Cl-4-Me--Ph)O B2 H Me4-(2-pyridyl) B3 H Me4-(5-CF.sub.3 -pyridin-2-yl) B4 Cl Me4-(2-pyridyl)O B7 Me Me4-(2-pyridyl)O B15 Me Me4-(2-pyridyl)O B7 CF.sub.3 Me4-(2-pyridyl)O B8 CF.sub.3 Me4-(2-pyridyl)O B34 CF.sub.3 Me4-(2-pyridyl)O B5 CF.sub.3 Me4-(5-CF.sub.3 -pyridin-2-yl)O B7 Me Me4-(5-CF.sub.3 -pyridin-2-yl)O B8 Me Me4-(5-CF.sub.3 -pyridin-2-yl)O B15 CF.sub.3 Me4-(5-CF.sub.3 -pyridin-2-yl)O B7 CF.sub.3 Me4-(5-CF.sub.3 -pyridin-2-yl)O B15 CF.sub.3 Me4-(5-CF.sub.3 -pyridin-2-yl)O B34 CF.sub.3 Me4-(3-Cl-5-CF.sub.3 -pyridin-2-yl) B7 Me Me4-(3-Cl-5-CF.sub.3 -pyridin-2-yl) B15 Me Me4-(3-Cl-5-CF.sub.3 -pyridin-2-yl) B34 Me Me4-(3-Cl-5-CF.sub.3 -pyridin-2-yl) B7 CF.sub.3 Me4-(3-Cl-5-CF.sub.3 -pyridin-2-yl) B15 CF.sub.3 Me4-(3-Cl-5-CF.sub.3 -pyridin-2-yl) B17 CF.sub.3 Me4-(3-Cl-5-CF.sub.3 -pyridin-2-yl) H CF.sub.3 Me4-(5-Cl-thiophen-2-yl) B8 Cl Me3-OCH.sub.2 O-4 B9 Cl Me4-OCF.sub.2 O-4 B10 CF.sub.3 Me4-MeCH.dbd.N B11 CF.sub.3 Me4-Me.sub.2 C.dbd.N B12 CF.sub.3 Me4-MeEtC.dbd.N H Cl Me4-PhCH.dbd.N B3 Cl Me4-PhMeC.dbd.N B7 Cl Me4-PhCH.sub.2 CH.dbd.N B8 CF.sub.3 Me4-cC.sub.6 H.sub.10 .dbd.N B15 CF.sub.3 Me3-CH.sub.2 CH.sub.2 CH.sub.2 -4 B16 CF.sub.3 Me3-CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 -4 B28 Cl Me4-PhC(O) H CF.sub.3 Me4-PhC(O) B7 Et Me4-PhC(O) B7 CF.sub.3 Me4-PhC(O) B33 CF.sub.3 Me4-(2-Cl--Ph)C(O) B7 CF.sub.3 Me4-(4-F--Ph)C(O) H CF.sub.3 Me4-(4-Cl--Ph)C(O) B7 CF.sub.3 Me4-(4-Cl--Ph)C(O) B15 CF.sub.3 Me4-(4-Cl-Ph)C(O) B34 CF.sub.3 Me4-(4-Me--Ph)C(O) B3 CF.sub.3 Me4-(4-Me--Ph)C(O) B16 CF.sub.3 Me4-(3,4-Cl.sub.2 --Ph)C(O) B45 CF.sub.3 Me2,4-Cl.sub.2 B7 CF.sub.3 Me3,4-Cl.sub.2 B7 CF.sub.3 Me4-Cl-2-F B7 CF.sub.3 Me3-Cl-4-nHex B7 CF.sub.3 Me4-tBu-3-Cl B7 CF.sub.3 Me4-tBu-3-Cl B15 CF.sub.3 Me3-Cl-4-iPrO B7 Me Me3-Cl-4-iPrO B7 CF.sub.3 Me3-Cl-4-nHepO B15 CF.sub.3 Me3-Cl-4-(3,4-Cl.sub.2 --PhCH.sub.2)O H CF.sub.3 Me3-Cl-4-PhCH.sub.2 O B7 CF.sub.3 Me3-Cl-4-Me.sub.3 CCH.sub.2 B7 CF.sub.3 Me3,4-(MeO).sub.2 B7 CF.sub.3 Me4-MeO-3-Me B17 CF.sub.3 Me4-OH-3,5-(tBu).sub.2 B3 CF.sub.3 Me3,4,5-Cl.sub.3 B15 CF.sub.3 Me3,5-Cl.sub.2 -4-F B7 CF.sub.3 Me4-Cl-2,6-F.sub.2 B7 CF.sub.3 Me2,6-F.sub.2 -4-CF.sub.3 B7 CF.sub.3 Me2,6-F.sub.2 -4-CF.sub.3 O B7 CF.sub.3 Me3,5-Cl.sub.2 -4-nOct B7 CF.sub.3 Me3,5-Cl.sub.2 -4-PhCH.sub.2 O B15 CF.sub.3 Me2,3,5,6-F.sub.4 -4-Me B3 CF.sub.3 Me2,3,4,5,6-F.sub.5 B33 CF.sub.3 Me______________________________________
TABLE 13______________________________________ ##STR328## ##STR329## ##STR330## ##STR331## ##STR332## ##STR333## ##STR334## ##STR335## ##STR336## ##STR337## ##STR338## ##STR339## ##STR340## ##STR341## ##STR342## ##STR343## ##STR344## ##STR345## ##STR346## ##STR347## ##STR348## ##STR349##R.sup.1 B A______________________________________iPr H 2,5-Me.sub.2 -1-pyrrolyliPr B3 1-Me-2-pyrrolyltBu B5 3,5-Me.sub.2 -2-pyrrolyltBu B6 3,4-Me.sub.2 -2-pyrrolyltBu B7 3,4,5-Me.sub.3 -2-pyrrolyl1-Me-cPr B8 3,5-Me.sub.2 -4-MeO-2-pyrrolyl1-Me-cPr B15 4-MeC(O)-3,5-Me.sub.2 -2-pyrrolyl1-Me-cPr B16 4-NO.sub.2 -2-pyrrolyl1-Me-cPr B17 2-Me-3-pyrrolyl1-Me-cHex B22 4-Me-3-pyrrolyl1-Me-cHex B31 2,4,5-Me.sub.3 3-pyrrolyl1-Me-cHex B32 2,4-Me.sub.2 -5-EtO.sub.2 C-3-pyrrolyl1-Me-cHex B33 1,2,3-triazol-4-ylPhCH.sub.2 B34 1-Me-1,2,3-triazol-4-ylPhCH.sub.2 B35 2-Me-1,2,3-triazol-4-ylPhCH.sub.2 B36 3-Me-1,2,3-triazol-4-ylPhMe.sub.2 C B40 2-EtO.sub.2 C-1,2,3-triazol-4-ylPhMe.sub.2 C B41 5-Me-2-Ph-1,2,3-triazol-4-ylPhMe.sub.2 C pyridin-2-yl-C(O) 5-CF.sub.3 -2-Me-1,2,3-triazol-4-ylPhMe.sub.2 C pyridin-2-yl-C(O) 2,5-Me.sub.2 -1,2,3-triazol-4-ylPh pyridin-2-yl-C(O) 1-PhCH.sub.2 -5-Me-1,2,3-trizol-4-yl2-F--Ph H 1-PhCH.sub.2 -5-CF.sub.3 -1,2,3-trizol-4-yl2-F--Ph B3 1-PhCH.sub.2 -5-Cl-1,2,3-trizol-4-yl2-F--Ph B5 4-Me-1,2,3-triazol-1-yl2-F--Ph B6 5-Me-1,2,3-triazol-2-yl2-Cl--Ph B7 4-MeO.sub.2 C-1,2,3-triazol-1-yl2-Cl--Ph B8 4,5-EtO.sub.2 C-1,2,3-triazol-2-yl2-Cl--Ph B15 4,5-Me.sub.2 -1,2,3-triazol-1-yl2-Me--Ph B16 4,5-(MeO.sub.2 C).sub.2 -1,2,3-triazol-2-yl2-Me--Ph B17 4,5-Me.sub.2 -1,2,4-triazol-3-yl2-Me--Ph B22 2,4-Me.sub.2 -1,2,4-triazol-3-yl4-NO.sub.2 --Ph B31 1,5-Me.sub.2 -1,2,4-trizol-3-yl2,6-F.sub.2 --Ph B32 5-Me-3-CF.sub.3 -1,2,4-triazol-2-yl2,6-F.sub.2 --Ph B33 3-Cl-5-CF.sub.3 -1,2,4-triazol-2-yl2,6-F.sub.2 --Ph B34 5-Cl-3-CF.sub.3 -1,2-4-triazol-2-yl2,6-F.sub.2 --Ph B35 3,5-Me.sub.3 1,2-4-triazol-4-yl2,6-F.sub.2 --Ph B36 3,5-Cl.sub.2 -1,2-4-triazol-4-yl2,6-Cl.sub.2 --Ph B40 3,5-(CF.sub.3).sub.2 -1,2-4-triazol-4-yl2,6-Cl.sub.2 --Ph B41 5-tetrazolyl2,6-Cl.sub.2 --Ph pyridin-2-yl-C(O) 5-Ph-1-tetrazolyl2,6-Cl.sub.2 --Ph pyridin-2-yl-C(O) 5-Ph-2-tetrazolyl2-pyridyl pyridin-2-yl-C(O) 3,4,4,5-Me.sub.4 -2-pyrazolin-1-yl2-pyridyl B8 3-Me-5-CF.sub.3 -2-pyrazolin-1-yl2-pyridyl B15 1,5-Me.sub.2 -3-CF.sub.3 -2-pyrazolin-4-yl2-pyridyl B16 1,4-Me.sub.2 -3-Ph-2-pyrazolin-4-yl2-pyridyl B17 1,4-Me.sub.2 -5-Ph-2-pyrazolin-4-yl2-pyridyl B22 1,3-Me.sub.2 -2-pyrazolin-5-yl1-naphthyl B31 1,5-Me.sub.2 -2-pyrazolin-3-yl1-naphthyl B32 2-Me-2-imizolin-1-yl1-naphthyl B33 2-CF.sub.3 -2-imizolin-1-yliPr B34 2-MeS-2-imizolin-1-yliPr B35 2-MeO-2-imizolin-1-yltBu B36 5-Me-2-Ph-2-oxazolin-4-yl1-Me-cPr B40 2,5-Me.sub.2 -2-oxazolin-4-ylcHex B41 5-Me-2-CF.sub.3 -2-oxazolin-4-yl1-Me-cHex pyridin-2-yl-C(O) 2-thiazolin-2-ylPhCH.sub.2 pyridin-2-yl-C(O) 2-Me.sub.2 N-2-thiazolin-4-ylPhMe.sub.2 C pyridin-2-yl-C(O) 2,4-Me.sub.2 -2-thiazolin-5-ylPh B8 2-Me-4-CF.sub.3 -2-thiazolin-5-yl2-F--Ph B15 5-Me-2-isoxazolin-3-yl2-Cl--Ph B16 3-Cl-5-Me-2-isoxazolin-4-yl2-Me--Ph B17 3,5-(MeS).sub.2 -2-isothiazolin-4-yl4-NO.sub.2 --Ph B22 5-Cl-2-Me-3(2H)-pyridazinon-4-yl2,6-F.sub.2 --Ph B31 5,6-Cl.sub.2 -2-Me-pyridazinon-4-yl2,6-Cl.sub.2 --Ph B32 4-Cl-2-Me-pyridazinon-4-yl2-pyridyl B33 4,6-Cl.sub.2 -2-Me-pyridazinon-4-yl1-naphthyl B34 4,5-Cl.sub.2 -2-Me-pyridazinon-4-yl______________________________________
TABLE 14______________________________________ ##STR350## ##STR351## ##STR352## ##STR353## ##STR354## ##STR355## ##STR356## ##STR357## ##STR358## ##STR359## ##STR360## ##STR361##R.sup.1 E B A______________________________________tBu oxazol-2-yl H A1tBu thiazol-2-yl B3 A2tBu imidazol-2-yl B7 A3tBu 1,5-Me.sub.2 -1,2,4-triazol-3-yl B8 A4tBu 5-Me-1,2,4-oxadiazol-3-yl B15 A5tBu 5-CF.sub.3 -1,2,4-thiadiazol-3-yl B16 A6tBu 5-Me-1,3,4-oxadiazol-2-yl B17 A7tBu tetrazol-5-yl B18 A8tBu 2-oxazolin-2-yl B32 A9tBu 1,2,4,5-tetrazin-3-yl B33 A10tBu F B34 A11tBu Cl H A12tBu Br B7 A13tBu I B8 A14tBu CHC H A15tBu CHC B7 A22,6-F.sub.2 --Ph CHC B7 A2tBu MeCC B7 A16tBu EtCC B7 A17tBu PhCC B7 A2tBu PhCC B8 A132,6-F.sub.2 --Ph PhCC H A22,6-F.sub.2 --Ph PhCC B7 A2pyridin-2-yl PhCC B7 A2tBu (2-Cl--Ph)CC B15 A19tBu (3-Cl--Ph)CC B15 A202,6-F.sub.2 --Ph (4-Cl--Ph)CC B16 A212,6-F.sub.2 --Ph (4-F--Ph)CC B17 A222,6-F.sub.2 --Ph (4-Me--Ph)CC B18 A232,6-F.sub.2 --Ph (4-nHex-Ph)CC B34 A242,6-F.sub.2 --Ph (2,6-Cl.sub.2 --Ph)CC H A252,6-F.sub.2 --Ph (2,4-Cl.sub.2 --Ph)CC (EtO).sub.2 P(S) A262,6-F.sub.2 --Ph (3,4-Cl.sub.2 --Ph)CC B3 A272,6-F.sub.2 --Ph (2,4,6-Me.sub.3 --Ph)CC B7 A282,6-F.sub.2 --Ph (4-CF.sub.3 --Ph)CC B15 A292,6-F.sub.2 --Ph CF.sub.3 B7 A22,6-F.sub.2 --Ph CF.sub.3 CF.sub.2 H A312,6-F.sub.2 --Ph NO.sub.2 B3 A322,6-F.sub.2 --Ph N.sub.3 B7 A332,6-F.sub.2 --Ph N.sub.3 H A22,6-F.sub.2 --Ph N.sub.3 B7 A1tBu N.sub.3 B7 A2tBu N.sub.3 H A2pyridin-2-yl N.sub.3 B7 A22,6-F.sub.2 --Ph CHO B8 A342,6-F.sub.2 --Ph C(O)Me B15 A352,6-F.sub.2 --Ph C(O)Et B16 A362,6-F.sub.2 --Ph C(O)iPr B17 A12,6-F.sub.2 --Ph C(O)nBu B18 A22,6-F.sub.2 --Ph C(O)sBu B32 A32,6-F.sub.2 --Ph C(O)tBu H A22,6-F.sub.2 --Ph C(O)tBu H A12,6-F.sub.2 --Ph C(O)tBu B7 A1tBu C(O)tBu H A2tBu C(O)tBu B7 A2tBu CO.sub.2 Me H A2tBu CO.sub.2 Me B7 A2tBu CO.sub.2 Me B8 A22,6-F.sub.2 --Ph CO.sub.2 Me H A22,6-F.sub.2 --Ph CO.sub.2 Me B7 A22,6-F.sub.2 --Ph CO.sub.2 Me B8 A2pyridin-2-yl CO.sub.2 Me H A2pyridin-2-yl CO.sub.2 Me B7 A2pyridin-2-yl CO.sub.2 Me B8 A2tBu CO.sub.2 Me B34 A5tBu CO.sub.2 Et H A2tBu CO.sub.2 Et B7 A2tBu CO.sub.2 Et B8 A22,6-F.sub.2 --Ph CO.sub.2 Et H A22,6-F.sub.2 --Ph CO.sub.2 Et B7 A22,6-F.sub.2 --Ph CO.sub.2 Et B8 A2pyridin-2-yl CO.sub.2 Et H A2pyridin-2-yl CO.sub.2 Et B7 A2pyridin-2-yl CO.sub.2 Et B8 A2pyridin-2-yl CO.sub.2 Et H A6pyridin-2-yl CO.sub.2 nPr B7 A7pyridin-2-yl CO.sub.2 iPr B8 A8pyridin-2-yl CO.sub.2 nBu H A9pyridin-2-yl CO.sub.2 iBu B7 A10pyridin-2-yl CO.sub.2 sBu B7 A11pyridin-2-yl CO.sub.2 tBu B8 A12pyridin-2-yl CO.sub.2 CH.sub.2 CH.dbd.CH.sub.2 B15 A13pyridin-2-yl CO.sub.2 CH.sub.2 CH.dbd.CH.sub.2 B7 A2tBu CO.sub.2 CH.sub.2 CH.dbd.CH.sub.2 B8 A2tBu CO.sub.2 CH.sub.2 CH.dbd.CH.sub.2 H A2tBu CO.sub.2 CH.sub.2 CH.dbd.CH.sub.2 B7 A22,6-F.sub.2 --Ph CO.sub.2 CH.sub.2 CH.dbd.CH.sub.2 B8 A22,6-F.sub.2 --Ph CO.sub.2 CH.sub.2 CH.dbd.CH.sub.2 H A22,6-F.sub.2 --Ph CO.sub.2 CH.sub.2 CH.dbd.CH.sub.2 B7 A2pyridin-2-yl C(O)NHMe B8 A22,6-F.sub.2 --Ph C(O)NHMe H A2tBu C(O)NHMe H A2pyridin-2-yl C(O)NHEt B16 A15pyridin-2-yl C(O)NHnPr B17 A16tBu C(O)NHiPr B18 A17tBu C(O)NHiBu B34 A18tBu C(O)NHtBu H A19tBu C(O)NMe.sub.2 (EtO).sub.2 P(S) A20tBu C(O)NMe.sub.2 H A2tBu C(O)NMe.sub.2 B7 A22,6-F.sub.2 --Ph C(O)NMe.sub.2 B7 A2pyridin-4-yl C(O)NMeEt B3 A212,6-F.sub.2 --Ph C(O)NEt.sub.2 B7 A22tBu C(O)N(nPr).sub.2 B15 A23tBu PhC(O) H A24tBu PhC(O) H A2tBu PhC(O) B7 A2tBu PhC(O) B8 A22,6-F.sub.2 --Ph PhC(O) H A22,6-F.sub.2 --Ph PhC(O) B7 A22,6-F.sub.2 --Ph PhC(O) B8 A2pyridin-2-yl PhC(O) H A2pyridin-2-yl PhC(O) B7 A22,6-F.sub.2 --Ph (4-F--Ph)C(O) B8 A22,6-F.sub.2 --Ph (3,4-Cl.sub.2 --Ph)C(O) H A6pyridin-3-yl (3-Cl-4-F--Ph)C(O) B8 A27pyridin-3-yl (4-Me--Ph)C(O) B15 A28tBu C(S)NH.sub.2 B16 A29tBu C(S)NH.sub.2 H A2tBu C(S)NH.sub.2 B7 A22,6-F.sub.2 --Ph C(S)NH.sub.2 B8 A22,6-F.sub.2 --Ph C(S)NH.sub.2 H A22,6-F.sub.2 --Ph C(S)NH.sub.2 B7 A2pyridin-2-yl C(S)NH.sub.2 B8 A2pyridin-2-yl C(S)NH.sub.2 H A22,6-F.sub.2 --Ph MeS B7 A22,6-F.sub.2 --Ph EtS B18 A31pyridin-2-yl nPrS B32 A32pyridin-2-yl tBuS B33 A33tBu MeSO B34 A34tBu EtSO H A35tBu nPrSO B7 A362,6-F.sub.2 --Ph tBuSO B8 A12,6-F.sub.2 --Ph MeSO.sub.2 H A22,6-F.sub.2 --Ph EtSO.sub.2 B7 A3pyridin-2-yl iPrSO.sub.2 B7 A4pyridin-2-yl nBuSO.sub.2 B8 A5tBu PhS B15 A6tBu PhS H A2tBu PhS B7 A22,6-F.sub.2 --Ph PhS B8 A22,6-F.sub.2 --Ph PhS H A22,6-F.sub.2 --Ph PhS B7 A2pyridin-2-yl PhS B8 A2pyridin-2-yl PhS H A2pyridin-2-yl PhS B7 A2tBu (4-Me--Ph)S B8 A2tBu (4-Cl--Ph)SO H A6tBu (2-F--Ph)SO.sub.2 B17 A92,6-F.sub.2 --Ph (MeO).sub.2 P(O) B18 A102,6-F.sub.2 --Ph (EtO).sub.2 P(O) B34 A112,6-F.sub.2 --Ph (nPrO).sub.2 P(O) H A12pyridin-2-yl (PhO)(MeO)P(O) (EtO).sub.2 P(S) A13pyridin-2-yl (MeO).sub.2 P(S) B3 A14tBu (EtO).sub.2 P(S) B7 A15tBu (nPrO).sub.2 P(S) B15 A16tBu (PhO)(MeO)P(S) B7 A17______________________________________
Where the compounds of the present invention are used as pesticides, in general, they can be mixed with a suitable carrier, for example a solid carrier, such as clay, talc, bentonite, diatomaceous earth or white carbon, or a liquid carrier such as water, alcohols (e.g., isopropanol, butanol, benzyl alcohol, furfuryl alcohol), aromatic hydrocarbons (e.g., toluene, xylene), ethers (e.g., anisole), ketones (e.g., cyclohexanone, isophorone), esters (e.g., butyl acetate), acid amides (e.g., N-methylpyrrolidone) or halogenated hydrocarbons (e.g., chlorobenzene), optionally along with other additives such as surfactant, emulsifier, dispersing agent, penetrating agent, spreading agent, thickener, anti-freezing agent, anti-caking agent and stabilizer, and can be formulated into any desired forms for practical use, such as liquid preparations, emulsions, wettable powders, dry flowables, flowables, dusts and granules.
Where the compounds of the present invention are used as agricultural chemicals, they can be combined with any other herbicides, various insecticides, acaricides, nematecides, fungicides, plant growth regulators, synergists, fertilizer and soil improvers, when they are formulated into preparations for practical use or while they are actually used through spraying or the like.
In particular, the combination of the compounds of the invention and other agricultural chemicals or plant hormones will be advantageous in that the amount of the chemicals to be used can be reduced thereby resulting in the reduction of the costs for the treatment, and that the mixed chemicals exhibit synergistic effects to broaden the insecticidal spectrum while displaying higher pesticidal activities. If desired, the compounds of the invention can be combined with a plurality of known agricultural chemicals. For the agricultural chemicals capable of being combined with the compounds of the invention, for example, the compounds described in Farm Chemicals Handbook, 1994 are referred.
Their concrete general names are raised below. However, the present invention is not necessarily limited by them.
Fungicide: acibenzolar, ampropyfos, anilazine, azaconazole, azoxystrobin, benalaxyl, benodanil, benomyl, benzamacril, binapacryl, biphenyl, bitertanol, bethoxazine, bordeaux mixture, blasticidin-S, bromoconazole, bupirimate, buthiobate, calcium polysulfide, captafol, captan, copper oxychloride, carpropamid, carbendazim, carboxin, chinomethionat, chlobenthiazone, chlorfenazol, chloroneb, chlorothalonil, chlozolinate, cufraneb, cymoxanil, cyproconazol, cyprodinil, cyprofuram, debacarb, dichlorophen, diclobutrazol, dichlofluanid, diclomezine, dicloran, diethofencarb, diclocymet, difenoconazole, diflumetorim, dimethirimol, dimethomorph, diniconazole, diniconazole-M, dinocap, diphenylamine, dipyrithione, ditalimfos, dithianon, dodemorph, dodine, drazoxolon, edifenphos, epoxiconazole, etaconazole, ethirimol, etridiazole, famoxadone, fenarimol, febuconazole, fenfuram, fenpiclonil, fenpropidin, fenpropimorph, fentin, ferbam, ferimzone, fluazinam, fludioxonil, fluoroimide, fluquinconazole, flusilazole, flusulfamide, flutolanil, flutriafol, folpet, fosetyl-aluminium, fuberidazole, furalaxyl, fenamidone, fenhexamid, guazatine, hexachlorobenzene, hexaconazole, hymexazol, imazalil, imibenconazole, iminoctadine, ipconazole, iprobenfos, iprodione, isoprothiolane, iprovalicarb, kasugamycin, kresoxim-methyl, mancopper, mancozeb, maneb, mepanipyrim, mepronil, metalaxyl, metconazole, metiram, metominostrobin, myclobutanil, nabam, nickel bis(dimethyldithiocarbamate), nitrothal-isopropyl, nuarimol, octhilinone, ofurace, oxadixyl, oxycarboxin, oxpoconazole fumarate, pefurzoate, penconazole, pencycuron, phthalide, piperalin, polyoxins, probenazole, prochloraz, procymidone, propamocarb hydrochloride, propiconazole, propineb, pyrazophos, pyrifenox, pyrimethanil, pyroquilon, quinoxyfen, quintozene, sulfur, spiroxamine, tebuconazole, tecnazene, tetraconazole, thiabendazole, thifluzamide, thiophanate-methyl, thiram, tolclofos-methyl, tolylfluanid, triadimefon, toriadimenol, triazoxide, tricyclazole, tridemorph, triflumizole, triforine, triticonazole, validamycin, vinclozolin, zineb, ziram.
Bacteriazide: streptomycin, oxyterracycline, oxolinic acid.
Nematicide: aldoxycarb, cadusafos, fosthiazate, fosthietan, oxamyl, fenamiphos.
Acaricide: acequinocyl, acrinathrin, amitraz, bifenazate, bromopropylate, chinomethionat, chlorobezilate, clofentezine, cyhexatine, dicofol, dienochlor, etoxazole, fenazaquin, fenbutatin oxide, fenpropathrin, fenproximate, halfenprox, hexythiazox, milbemectin, phenisobromolate, polynactins, propargite, pyridaben, pyrimidifen, tebufenpyrad, tetradifon.
Insecticide: abamectin, acephate, acetamipirid, alanycarb, azinphos-methyl, bendiocarb, benfuracarb, bensultap, bifenthrin, Batillus thuringiensis, buprofezin, butocarboxim, carbaryl, carbofuran, carbosulfan, cartap, chlorfenapyr, chlorpyrifos, chlorfenvinphos, chlorfluazuron, clothianidin, chromafenozide, chlorpyrifos-methyl, cyanox, cycloprothrin, cyfluthrin, beta-cyfluthrin, cypermethrin, cyromazine, cyhalothrin, lambda-cyhalothrin, deltamethrin, diafenthiuron, diazinon, diacloden, dichlorvos, diflubenzuron, dimethylvinphos, diofenolan, disulfoton, dimethoate, emamectin-benzoate, EPN, esfenvalerate, ethiofencarb, endosulfan, ethiprole, ethylthiometone, etofenprox, etrimfos, fenitrothion, fenobucarb, fenothiocarb, fenthion, fenoxycarb, fenpropathrin, fenvalerate, fipronil, flucythrinate, flufenoxuron, flufenprox, tau-fluvalinate, fonophos, formetanate, formothion, furathiocarb, halofenozide, hexaflumuron, hydramethylnon, imidacloprid, isofenphos, indoxacarb, isoprocarb, isoxathion, lufenuron, malathion, metaldehyde, methamidophos, methidathion, methacrifos, metalcarb, methomyl, methoprene, methoxychlor, methoxyfenozide, monocrotophos, muscalure, nicotin-sulfate, nitenpyram, omethoate, oxydemeton-methyl, oxamyl, parathion, parathion-methyl, permethrin, phenthoate, phoxim, phorate, phosalone, phosmet, phosphamidon, pirimicarb, pirimiphos-methyl, profenofos, propafos, prothiofos, pymetrozine, pyraclofos, pyridafenthion, pyriproxyfen, rotenone, sulprofos, silafluofen, spinosad, sulfotep, tebfenozide, teflubenzuron, tefluthorin, terbufos, tetrachlorvinphos, thiodicarb, thiamethoxam, thiocyclam, thiofanox, thiometon, tolfenpyrad, tralomethrin, trichlorfon, triazuron, triflumuron, vamidothion.
The dose of the compounds of the present invention varies depending on an application place, an application time, an application method, cultivation crops, etc. In general, it may be between approximately 0.005 kg and 50 kg per hectare (ha) in terms of the amount of the active ingredient.
Now, formulation examples comprising the compounds of the invention are mentioned below, which, however, are not intended to restrict the scope of the invention. In the following formulation examples, "part" or "parts" are by weight.
______________________________________[Wettable Powders]______________________________________Compound of the invention 5 to 80 partsSolid carrier 10 to 85 partsSurfactant 1 to 10 partsOthers 1 to 5 parts______________________________________
The others include, for example, anti-caking agent, etc.
______________________________________[Emulsions]Compound of the invention 1 to 30 partsLiquid carrier 30 to 95 partsSurfactant 5 to 15 parts[Flowables]Compound of the invention 5 to 70 partsLiquid carrier 15 to 65 partsSurfactant 5 to 12 partsOthers 5 to 30 parts______________________________________
The others include, for example, anti-freezing agent, thickener, etc.
______________________________________[Dry Flowables (wettable granules)]Compound of the invention 20 to 90 partsSolid carrier 10 to 60 partsSurfactant 1 to 20 parts[Granules]Compound of the invention 0.1 to 10 partsSolid carrier 90 to 99.99 partsOthers 1 to 5 parts[Dusts]Compound of the invention 0.01 to 30 partsSolid carrier 67 to 99.5 partsOthers 0 to 3 parts______________________________________
Where the compounds of the present invention are used as an agent for preventing the attachment of aquatic organisms, they may be formulated into various preparations of, for example, coating paints, solutions, emulsions, pellets or flakes to be applicable to various objects. Depending on the application place, the object and the form, the preparations can be used in any ordinary manners of, for example, coating, spraying, dipping, adding to water or installing in water. To prepare such coating paints, solutions, emulsions and others, employable are any ordinary methods. Apart from the above-mentioned preparations and modes of using the compounds of the present invention, the compounds may also be used, for example, by incorporating them into ropes or fiber materials for fishing nets in the stage of preparing the ropes or fiber materials to thereby making them have the ability to prevent the attachment of aquatic organisms thereto. The agents for preventing the attachment of aquatic organisms according to the present invention can be used either singly or as combined with any other agents for preventing the attachment of aquatic organisms.
Where the aquatic adhesion inhibitors of the invention are used in the form of antifouling coatings, for example, the compounds of the invention may be mixed with film-forming agents to prepare coatings. The film-forming agents include oil varnishes, synthetic resins, artificial rubbers, etc. If desired, solvents, pigments and others can be added to the coatings. To prepare the paints, the uppermost limit of the concentration of the compounds of the invention to be therein is not specifically limited, provided that the resulting coatings can form film, but may be from 1 to 50% by weight, preferably from 5 to 20% by weight, relative to the weight of the antifouling coatings.
Where the agents for preventing the attachment of aquatic organisms of the present invention are used in the form of solutions, for example, the compounds of the invention may be dissolved in solvents along with film-forming agents to prepare solutions. The film-forming agents include synthetic resins, artificial rubbers, natural resins, etc. The solvents include xylene, toluene, cumene, methyl ethyl ketone, methyl isobutyl ketone, acetone, etc. If desired, additives such as plasticizer may be added to the solutions. To prepare the solutions, the uppermost limit of the concentration of the compounds of the invention to be therein is not specifically limited, provided that the compounds are dissolved to give solutions, but may be from 1 to 50% by weight, preferably from 5 to 30% by weight, relative to the weight of the solutions.
Where the agents for preventing the attachment of aquatic organisms of the present invention are used in the form of emulsions, surfactants are added to the compounds of the invention to prepare the intended emulsions according to ordinary methods of preparing general emulsions. In this, the type of the surfactants to be used is not specifically limited. To prepare the emulsions, the uppermost limit of the concentration of the compounds of the invention to be therein is not specifically limited, provided that the compounds are emulsified to give emulsions, but may be from 1 to 50% by weight, preferably from 5 to 30% by weight, relative to the weight of the emulsions.
Where the agents for preventing the attachment of aquatic organisms of the present invention are used in the form of pellets or flakes, for example, the constitutive components of the compounds of the invention and optionally plasticizers, surfactants and others are added to the base of hydrophilic resins which are solid at room temperature, such as polyethylene glycol in a solid form, and the resulting mixtures are shaped into pellets or flakes through melting molding, compression molding or the like. To prepare the pellets or flakes, the uppermost limit of the concentration of the compounds to be therein is not specifically limited, provided that the compounds can be shaped into pellets or flakes, but may be from 20 to 95% by weight, preferably from 30 to 90% by weight, relative to the weight of the pellets or flakes.

EXAMPLES
The present invention is illustrated specifically by referring to the following Synthesis Examples, Formulation Examples and Test Examples, which, however, are not intended to restrict the scope of the invention.
Synthesis Example 1
Synthesis of 2-{3-(2,6-difluorophenyl)pyrazol-1-yl}-3-(1-methyl-3, 5-dichloropyrazol-4-yl)-3-hydroxyacrylonitrile
(Compound No. I-40)
1) 3.0 g of 3-(2,6-difluorophenyl)pyrazole was dissolved in 20 ml of acetonitrile, and 2.52 g of chloroacetonitrile and 4.61 g of potassium carbonate were added thereto at room temperature, and heated under reflux for 5 hours. After acetonitrile was distilled off under reduced pressure, ethyl acetate was added to the residue, which was then washed with a small amount of water. The organic layer was dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The residual product was recrystallized from a mixed solvent of isopropylether and diethyl ether to obtain 1.74 g of 1-cyanomethyl-3-(2,6-difluorophenyl)pyrazole.
2) A solution of 0.5 g of 1-cyanomethyl-3-(2,6-difluorophenyl)pyrazole dissolved in 10 ml of THF was dropwise added to a suspension of 0.15 g of 55% sodium hydride in 10 ml of THF, at 50.degree. C. After the resulting product was stirred for 30 minutes, a solution of 0.67 g of 1-(1-methyl-3, 5-dichloropyrazole-4-carbonyl)pyrazole dissolved in 10 ml of THF was dropwise added thereto at 50.degree. C. and then stirred overnight at room temperature. The reaction mixture was poured into water, then extracted with ethyl acetate and washed with a small amount of water. The resulting product was dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The residual product was recrystallized from a mixed solvent of isopropyl ether/ethyl acetate=3/1 to obtain 0.52 g of 2-{3-(2,6-difluorophenyl)pyrazol-1-yl}-3-(l-methyl-3,5-dichloropyrazol-4-yl)-3-hydroxyacrylonitrile.
Synthesis Example 2
Synthesis of 3-(1-methyl-3,5-dichloropyrazol-4-yl)-2-(2-phenylthiazol-4-yl)-3-hydroxyacrylonitrile
(Compound No. II-1)
1) 2.33 g of thiobenzamide was dissolved in 20 ml of dry methanol, and 2.16 g of 1,3-dichloroacetone was added thereto at room temperature and then heated under reflux for 1 hour. The solvent was distilled off under reduced pressure, and ice water was added to the remaining product, which was then neutralized with an aqueous solution of sodium hydrogen carbonate. The resulting product was extracted with ethyl acetate, washed with saturated saline, and dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The residual product was purified through silica gel column chromatography to obtain 2.03 g of 4-chloromethyl-2-phenylthiazole was obtained from the fraction eluted with chloroform/n-hexane=1/2.
2) 1.39 g of 4-chloromethyl-2-phenylthiazole was dissolved in 10 ml of acetonitrile, and 0.65 g of potassium cyanide and 0.05 g of dibenzo-18-crown-6-ether were added thereto at room temperature, and then heated under reflux for 10 hours. After the temperature was returned to room temperature, ethyl acetate was added the resulting mixture, and the insoluble solid was removed through filtration. The resulting ethyl acetate solution was washed with saturated saline and water, and dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The residual product was purified through silica gel column chromatography to obtain 0.98 g of 4-cyanomethyl-2-phenylthiazole from the fraction eluted with chloroform.
3) 0.72 g of 4-cyanomethyl-2-phenylthiazole was dissolved in 10 ml of dry THF, and 4.6 ml of n-butyl lithium (1.56 M hexane solution) was dropwise added thereto at -60.degree. C. or lower in an argon atmosphere. After the resulting product was stirred at -60.degree. C. or lower for 20 minutes, 0.84 g of 1-methyl-3,5-dichloropyrazole-4-carbonyl chloride as dissolved in 3 ml of dry THF was dropwise added thereto at -60.degree. C. or lower. Then, the resulting product was gradually heated, and stirred for 4 hours at room temperature. The reaction mixture was poured into ice water, acidified with diluted hydrochloric acid, extracted with ethyl acetate, and washed with saturated saline. The resulting product was dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The residual product was purified through silica gel column chromatography to obtain the intended product from the fraction eluted with chloroform. The resulting product was crystallized and washed with diethyl ether to obtain 0.86 g of 3-(1-methyl-3,5-dichloropyrazol-4-yl)-2-(2-phenylthiazol-4-yl)-3-hydroxyacrylonitrile.
Synthesis Example 3
Synthesis of 3-(1-methyl-3-trifluoromethyl-5-chloropyrazol-4-yl)-2-(4-tert-butylthiazol-2-yl)-3-pivaloyloxyacrylonitrile
(Compound No. III-6, III-15)
0.5 g of 3-(1-methyl-3-trifluoromethyl-5-chloropyrazol-4-yl)-2-(4-tert-butylthiazol-2-yl)-3-hydroxyacrylonitrile and 0.14 g of triethylamine were added to 15 ml of THF at room temperature and stirred to give a uniform solution. 0.16 g of pivaloyl chloride was dropwise added to the solution with cooling with ice, then gradually heated, and stirred at room temperature for 8 hours. The reaction mixture was poured into ice water, extracted with ethyl acetate, and washed thrice with saturated saline. After having been dried over sodium sulfate, the resulting product was passed through a short column filled with silica gel. The solvent was distilled off under reduced pressure, and the residual product was applied to silica gel thin-layer chromatography (developer solvent: chloroform) to obtain 0.16 g of 3-(1-methyl-3-trifluoromethyl-5-chloropyrazol-4-yl)-2-(4-tert-butylthiazol-2-yl)-3-pivaloyloxyacrylonitrile (III-6) and 0.35 g of its geometric isomer (III-15).
Compound No. III-6
.sup.1 H-NMR (CDCl.sub.3, .delta. ppm); 1.18 (9H, s), 1.32 (9H, s), 3.85 (3H, s), 6.88 (1H, s)
Compound No. III-15
.sup.1 H-NMR (CDCl.sub.3, .delta. ppm); 1.33 (9H, s), 1.39 (9H, s), 3.94 (3H, s), 7.03 (1H, s)
Reference Example
Synthesis of 1-methyl-3-trifluoromethyl-5-chloropyrazole-4-carboxylic acid
1) 21.35 g of phosphorus oxychloride was dropwise added to 4.72 g of DMF at 10.degree. C. or lower. After the temperature of the reaction solution was returned to room temperature, the reaction mixture was stirred for 1 hour, and 10.71 g of 1-methyl-3-trifluoromethyl-5-pyrazolone was added thereto. The resulting mixture was heated up to 110.degree. C., and stirred for 7 hours. After having been left to be at 70.degree. C. the reaction mixture was poured into ice water. After pH of the mixture was made to be about 4 with an aqueous solution of sodium hydroxide added thereto, and precipitated crystals were taken out through filtration and dried to obtain 10.55 g of 1-methyl-3-trifluoromethyl-5-chloropyrazole-4-carbaldehyde.
2) 8.88 g of 1-methyl-3-2-(tert-trifluoromethyl-5-chloropyrazole-4-carbaldehyde and 7.24 g of potassium permanganate were added to an aqueous solution of 0.23 g of potassium hydroxide in 85 ml of water, at room temperature. After having been heated up to 60.degree. C., the resulting mixture was stirred for 2 hours. Next, the temperature of the mixture was return to room temperature, and the solid was removed through filtration. The resulting filtrate was acidified with an aqueous solution of hydrochloric acid, and precipitated crystals were taken out through filtration, washed with water, and dried. The thus-obtained crystals were added to 150 ml of chloroform, and heated under reflux, and the insoluble solid was removed through filtration at a heating time. Chloroform was distilled off under reduced pressure, and 6.24 g of 1-methyl-3-trifluoromethyl-5-chloropyrazole-4-carboxylic acid was obtained.
Synthesis Example 4
Synthesis of 2-(2-tert-butylthiazol-4-yl)-3-(2-methyl-4-trifluoromethylthiazol-5-yl)-3-benzoyloxyacrylonitrile
(Compound No. II-75)
In the same manner as above, the above-mentioned compound was synthesized (viscous liquid, E-Z mixture).
.sup.1 H-NMR (CDCl.sub.3, .delta. ppm); 1.09 (9H, s), 2.75 (3H, s), 7.3-7.6 (4H, m), 8.05-8.25 (2H, m): major 1.19 (9H, s), 2.70 (3H, s), 7.3-7.6 (4H, m), 8.05-8.25 (2H, m): minor
Synthesis Example 5
Synthesis of 2-(4-trifluoromethylphenyl)-3-(1-methyl-3,5-dichloropyrazol-4-yl)-3-(1-methyl-3,5-dichloropyrazole-4-carbonyloxy)acrylonitrile
(Compound No. IV-5)
1.0 g of 4-(trifluoromethyl)phenylacetonitrile and 2.31 g of 1-methyl-3,5-dichloropyrazole-4-carbonyl chloride were dissolved in 30 ml of dry THF, and 0.61 g of potassium t-butoxide was added thereto at room temperature. After having been heated, the resulting product was kept heated under reflux for 3 hours. 0.61 g of potassium t-butoxide was again added thereto and further heated under reflux for 2 hours. THF was distilled off under reduced pressure, and water was added to the residual product, which was then extracted with ethyl acetate. The resulting organic layer was washed with a dilute aqueous solution of sodium hydroxide and then with water. This was dried with sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified through silica gel column chromatography to obtain 1.92 g of 3-(1-methyl-3,5-dichloropyrazol-4-yl)-2-(4-trifluoromethylphenyl)-3-(1-methyl-3,5-dichloropyrazole-4-carbonyloxy)acrylonitrile from the fraction eluted with n-hexane:ethyl acetate=2:1.
Synthesis Example 6
Synthesis of 2-(4-tert-butylphenyl)-3-(1-methyl-3,5-dichloropyrazol-4-yl)-3-hydroxyacrylonitrile
(Compound No. IV-18)
0.22 g of dibenzo-18-crown-6-ether and 1.57 g of sodium cyanide were suspended in 20 ml of DMSO, and 5.00 g of 4-tert-butylbenzyl bromide was dropwise added thereto with cooling with water. After having been stirred overnight at room temperature, the resulting mixture was further stirred at 50.degree. C. for 5 hours. After this was left to be at room temperature, water was added thereto and extracted with ether. The organic layer was washed with water, and dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The residual product was purified through silica gel column chromatography to obtain 1.19 g of 4-tert-butylphenylacetonitrile was obtained from the fraction eluted with n-hexane:ethyl acetate 5:1.
1.00 g of 4-tert-butylphenylacetonitrile and 1.23 g of 1-methyl-3,5-dichloropyrazole-4-carbonyl chloride were dissolved in 20 ml of THF, and 1.01 g of potassium t-butoxide was added thereto with cooling with ice. After the resulting mixture was stirred overnight at room temperature, water was added thereto, acidified with diluted hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with water, and dried with sodium sulfate, and the solvent was distilled off under reduced pressure. The residual product was dissolved in a mixed solvent of 10 ml of water and 10 ml of dioxane, and 0.38 g of potassium hydroxide was added thereto and heated under reflux for 4 hours. After having been left to be at room temperature, this was acidified with diluted hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with water, and dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The residual product was purified through silica gel column chromatography to obtain 0.64 g of 2-(4-tert-butylphenyl)-3-(l-methyl-3,5-dichloropyrazol-4-yl)-3-hydroxyacrylonitrile from the fraction eluted with n-hexane:ethyl acetate=2:1.
Synthesis Example 7
Synthesis of 2-(4-tert-butylphenyl)-3-(1-methyl-3-trifluoromethyl-5-chloropyrazol-4-yl)-3-pivaloyloxyacrylonitrile
(Compound No. IV-24)
In the same manner as above, the above-mentioned compound was synthesized (viscous liquid).
.sup.1 H-NMR (CDCl.sub.3, .delta. ppm); 1.13 (9H, s), 1.33 (9H, s), 3.98 (3H, s), 7.48 (4H, brs)
Synthesis Example 8
Synthesis of 2-(4-tert-butylphenyl)-3-(3,5-dichloro-1-methylpyrazol-4-yl)-3-methoxycarbonyloxyacrylonitrile
(Compound No. IV-36)
In the same manner as above, the above-mentioned compound was synthesized (vitreous, E-Z mixture).
.sup.1 H-NMR (CDCl.sub.3, .delta. ppm); 1.32 (9H, s), 3.75 (3H, s), 3.87 (3H, s), 7.49 (2H, d, J=8 Hz), 7.58 (2H, d, J=8 Hz): 75% 1.27 (9H, s), 3.88 (3H, s), 3.96 (3H, s), 7.49 (2H, d, J=8 Hz), 7.58(2H, d, J=8 Hz): 25%
Synthesis Example 9
Synthesis of 2-{2-tert-butyloxazol-4-yl}-3-(3,5-dichloro-1-methyl-pyrazol-4-yl)-3-hydroxyacrylonitrile
(Compound No. V-40)
1) 25 g of pivalic acid amide and 25 g of 1,3-dichloro-2-propanone were mixed and heated on an oil bath at 135.degree. C. for 2.5 hours. After having been cooled with ice, the mixture was made alkaline with an aqueous solution of sodium hydroxide added thereto. Then, the resulting product was extracted with ethyl acetate, washed with water, and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residual product was purified through column chromatography (silica gel; ethyl acetate n-hexane=1:8) to obtain 17.5 g of 2-tert-butyl-4-chloromethyloxazole.
2) 6.2 g of sodium cyanide was weighed, 50 ml of dimethylsulfoxide was added thereto, and a dimethylsulfoxide solution of 16.9 g of 2-tert-butyl-4-chloromethyloxazole was dropwise added thereto, and heated on an oil bath at 65.degree. C. for 1 hour with stirring. After the resulting product was cooled to room temperature, 150 ml of a dilute aqueous solution of sodium hydroxide was added thereto, and extracted with toluene. The organic layer was fully washed with water, and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 14.8 g of 2-tert-butyl-4-cyanomethyloxazole.
3) 2.87 g of potassium tert-butoxide was suspended in 20 ml of THF, and a solution of 2.00 g of 2-tert-butyl-4-cyanomethyloxazole and 2.37 g of 3,5-dichloro-1-methylpyrazole-4-carbonyl chloride as dissolved in 10 ml of THF was dropwise added thereto with cooling with ice, and then stirred overnight at room temperature. The reaction mixture was poured into ice water, extracted with ethyl acetate, and washed with a small amount of water. After the resulting product was dried with anhydrous sodium sulfate, the solvent was evaporated out under reduced pressure. The residual product was purified through column chromatography (silica gel; n-hexane:ethyl acetate=4:1) to obtain 3.26 g of the intended compound.
Synthesis Example 10
Synthesis of 2-(2-tert-butyloxazol-4-yl)-3-(5-chloro-1-methyl-3-trifluoromethylpyrazol-4-yl)-3-ethoxymethoxyacrylonitrile
(Compound No. V-44)
0.6 g of 2-{2-tert-butyloxazol-4-yl}-3-(5-chloro-3-trifluoromethyl-l-methyl-pyrazol-4-yl)-3-hydroxyacrylonitrile was dissolved in 5 ml of THF, and 0.07 g of 60% sodium hydride was added thereto with cooling with ice, and then stirred for 15 minutes at room temperature. 0.17 g of ethoxymethyl chloride was added thereto and stirred for 6 days at room temperature. The reaction mixture was poured into ice water, extracted with ethyl acetate, and washed with saturated saline. The resulting product was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residual product was purified through silica gel thin-layer chromatography (ethyl acetate:n-hexane=1:4) to obtain 0.1 g of the intended compound in vitreous state.
.sup.1 H-NMR (CDCl.sub.3, .delta. ppm); 1.17 (3H, t), 1.41 (9H, s), 3.98 (3H, s), 5.03 (2H, s), 8.00 (1H, s)
Synthesis Example 11
Synthesis of ethyl 2-phenyl-3-(3,5-dichloro-1-methylpyrazol-4-yl)-3-hydroxyacrylate
(Compound No. IV-91)
8.2 g (50 mmols) of ethyl phenylacetate and 10.7 g (50 mmols) of 3,5-dichloro-1-methylpyrazole-4-carboxylic acid chloride were dissolved in 100 ml of dry tetrahydrofuran, and 14 g (125 mmols) of potassium tert-butoxide at room temperature. The reaction mixture was stirred at room temperature for 1 hour, and 300 ml of water was added thereto, and extracted with ethyl acetate. The organic layer was washed with water and saturated saline, and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 17 g of the intended ethyl 2-phenyl-3-(3,5-dichloro-1-methylpyrazol-4-yl)-3-hydroxyacrylate.
.sup.1 H-NMR (CDCl.sub.3, .delta. ppm); 1.1-1.5 (3H, m), 3.59 (1.5H, s), 3.73 (1.5H, s), 3.95-4.45 (2H, m), 5.58 (0.5H, s), 7.0-7.35 (5H, m), 13.21 (0.5H, s)
Synthesis Example 12
Synthesis of 1-(3,5-dichloro-1-methylpyrazol-4-yl)-2-phenyl-2-bromoethanone
(Compound No. IV-90)
1) 17 g (50 mmols) of ethyl 2-phenyl-3-(3,5-dichloro-1-methylpyrazol-4-yl)-3-hydroxyacrylate was dissolved in 50 ml of 6 N HCl and 250 ml of 1,4-dioxane, and heated under reflux for 15 hours. The reaction mixture was poured into 500 ml of ice water, and precipitated crystals were taken out through filtration to obtain 8 g of the intended 1-(3,5-dichloro-1-methylpyrazol-4-yl)-2-phenylethanone as white crystals. m.p.: 94-96.degree. C.
2) 5.38 g (20 mmols) of 1-(3,5-dichloro-1-methylpyrazol-4-yl)-2-phenylethane was dissolved in 50 ml of chloroform, and stirred at room temperature for 1 hour, and the solvent was distilled off under reduced pressure to obtain the intended 1-(3,5-dichloro-1-methylpyrazol-4-yl)-2-phenyl-2-bromoethanone as white crystals. m.p.: 74.5-75.5.degree. C.
Synthesis Example 13
Synthesis of 1-(3,5-dichloro-1-methylpyrazol-4-yl)-1-pivaloyloxy-2-phenyl-2-bromoethylene
(Compound No. IV-92)
0.55 g (1.58 mmols) of 1-(3,5-dichloro-1-methylpyrazol-4-yl)-2-phenyl-bromoethane and 0.18 g (1.74 mmols) of triethylamine were dissolved in 4 ml of dry tetrahydrofuran, and 0.19 g (1.58 mmols) of pivalic acid chloride was added thereto at room temperature. After the reaction mixture was stirred for 16 hours at room temperature, 10 ml of water was added thereto, and extracted with ethyl acetate. The organic layer was washed with water and saturated saline, and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified through silica gel column chromatography to obtain 0.23 g of the intended 1-(3,5-dichloro-l-methylpyrazol-4-yl)-1-pivaloyloxy-2-phenyl-2-bromoethylene as a colorless liquid (E-Z mixture).
.sup.1 H-NMR (CDCl.sub.3, .delta. ppm); 1.05 (9H, s), 3.81 (3H, s), 7.37 (5H, m): major 1.32 (9H, s), 3.62 (3H, s), 7.24 (5H, m): minor
Synthesis Example 14
Synthesis of 1-(3,5-dichloro-1-methylpyrazol-4-yl)-2-{2-(1-methylcyclohexan-1-yl}-thiazol-4-yl-2-diethylphosphonoethanone
(Compound No. II-156)
1) 4.15 g (18.1 mmols) of 2-(1-methyl-cyclohexan-1-yl)-4-chloromethylthiazole and 3.32 g (20 mmols) of trimethyl phosphate were mixed and heated under reflux for 16 hours. The reaction mixture was cooled to room temperature, and purified through silica gel column chromatography to obtain 4.63 g of the intended diethyl {2-(1-methylcyclohexan-1-yl-thiazol-4-yl}methylphosphonate as a colorless liquid.
.sup.1 H-NMR (CDCl.sub.3, .delta. ppm); 1.25 (3H, t, J=7.2 Hz), 1.31 (3H, s), 1.1-2.3 (1OH, m), 3.33 (2H, d, J=20.4 Hz), 4.04 (4H, dd, J=7.2, 7.2 Hz), 7.01 (1H, m)
2) 0.85 g (4 mmols) of 3,5-dichloro-1-methylpyrazole-4-carboxylic acid chloride and 1.32 g (4 mmols) of diethyl {2-(1-methylcyclohexan-1-yl-thiazol-4-yl}methylphosphonate were dissolved in 15 ml of dry tetrahydrofuran, and 1.12 g (10 mmols) of potassium t-butoxide was added thereto at room temperature. The reaction mixture was stirred for 1 hour at room temperature, and 20 ml of water was added thereto, and extracted with ethyl acetate. The organic layer was washed with water and saturated saline, and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified through silica gel column chromatography to obtain 0.4 g of the intended 1-(3,5-dichloro-1-methylpyrazol-4-yl)-2-{2-(1-methylcyclohexan-1-yl)-thiazol-4-yl}-2-diethylphosphonoethanone.
.sup.1 H-NMR (CDCl.sub.3, .delta. ppm); 1.23 (3H, t, J=7.2 Hz), 1.23 (3H, s), 1.1-2.3 (1OH, m), 3.79 (3H, s), 4.09 (2H, dd, J=7.2, 7.2 Hz), 5.90 (1H, d, J=22.8 Hz), 7.43 (1H, m)
Synthesis Example 15
Synthesis of allyl 2-{3-(2,6-difluorophenyl)pyrazol-1-yl}-3-(5-chloro-1-methyl-3-trifluoromethylpyrazol-4-yl)-3-hydroxyacrylate
(Compound No. I-133)
1) Potassium carbonate (1.53 g) was added to an acetonitrile (10 mL) solution of 3-(2,6-difluorophenyl)-pyrazole (1 g) and allyl 2-bromoacetate (1.49 g), and refluxed for 3 hours. The resulting product was extracted with acetate and diluted hydrochloric acid added thereto at room temperature. The organic layer was dried over anhydrous magnesium sulfate and concentrated, and the resulting concentrate was purified through silica gel column chromatography (chloroform) to obtain allyl 2-{3-(2,6-difluorophenyl)pyrazol-1-yl}acetate (1.5 g).
.sup.1 H-NMR (CDCl.sub.3, .delta. ppm); 4.70 (2H, d, J=6.0 Hz), 5.10 (2H, s), 5.30-5.60 (2H, m), 5.70-6.40 (1H, m), 6.50-7.80 (5H, m)
2) Potassium butoxide (0.5 g) was added to a THF (10 mL) solution of allyl 2-{3-(2,6-difluorophenyl)pyrazol-1-yl}acetate (0.5 g) and 5-chloro-1-methyl-3-trifluoromethylpyrazole-4-carbonyl chloride (0.44 g) at 0.degree. C. and stirred for 5 minutes. Water (5 ml) was added thereto, and then extracted with diluted hydrochloric acid and ethyl acetate. After the organic layer was dried over anhydrous magnesium sulfate, and then concentrated, and the resulting concentrate was purified through silica gel column chromatography (chloroform) to obtain the intended product, Compound No. I-133 (0.89 g).
.sup.1 H-NMR (CDCl.sub.3, .delta. ppm): 3.95 (3H, s), 4.80 (2H, d, J=6.0 Hz), 5.20-5.60 (2H, m), 5.60-6.40 (1H, m), 6.45-7.90 (6H, m)
Synthesis Example 16
Synthesis of 2-bromo-2-{3-(2,6-difluorophenyl)pyrazol-1-yl}-1-(5-chloro-1-methyl-3-trifluoromethylpyrazol-4-yl)-1-hydroxyethylene
(Compound No. I-134)
1) Formic acid (60 mg) was added to a THF (1 mL) solution of palladium acetate (7 mg) and triphenylphosphine (17 mg) and stirred for 5 minutes at room temperature in a nitrogen atmosphere. A THF (5 mL) solution of Compound I-133 (0.32 g) was added thereto and refluxed for 1 hour. The reaction mixture was left to be at room temperature, and concentrated, and the resulting concentrate was purified through silica gel column chromatography (chloroform) and recrystallization (chloroform-diisopropyl ether) to obtain 2-{3-(2,6-difluorophenyl)pyrazol-1-yl}-3-(5-chloro-1-methyl-3-trifluoromethylpyrazol-4-yl)ethan-1-one (0.1 g). m.p.: 152-154.degree. C.
2) A THF solution (0.27 mL) of 1M lithium hexamethyldisilazide was added to a THF solution of 2-{3-(2,6-difluorophenyl)pyrazol-1-yl}-3-(5-chloro-1-methyl-3-trifluoromethylpyrazol-4-yl)ethan-1-one (0.1 g) at -78.degree. C. and stirred at the same temperature in a nitrogen atmosphere. To the resulting solution was added a THF (2 mL) solution of carbon tetrabromide (0.098 g), and then gradually heated up to room temperature. Water (1 mL) was added thereto, and then extracted with diluted hydrochloric acid and ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and recrystallized from chloroform-diethyl ether) to obtain the intended product, Compound No. I-134 (0.062 g). m.p.: 123-125.degree. C.
Synthesis Example 17
Synthesis of 2-bromo-2-{3-(2,6-difluorophenyl)pyrazol-1-yl}-1-(5-chloro-1-methyl-3-trifluoromethylpyrazol-4-yl)-1-pivaloyloxyethylene
(Compound No. I-135)
Triethylamine (0.3 g) and pivalic acid chloride (0.23 g) were added in that order to a chloroform (25 mL) solution of Compound No. I-134 (0.47 g) at 0.degree. C., and stirred at room temperature for 1 hour. The resulting product was extracted with water and chloroform. The organic layer was dried with anhydrous magnesium sulfate, concentrated, and purified through silica gel column chromatography (chloroform) to obtain the intended product, Compound No. I-135 (0.4 g).
.sup.1 H-NMR (CDCl.sub.3, .delta. ppm); 1.25 (9H, s), 3.90 (3H, s), 6.55-7.80 (5H, m)
In accordance with the above-mentioned reaction schemes or Examples, various compounds of the present invention were produced, of which the structure and the melting point are shown in Table 15 to Table 19 below. Unless otherwise specifically indicated, the compounds shown in these are in the form of a mixture of E-form and Z-form. The abbreviations in these have the same meanings as those mentioned above.
TABLE 15__________________________________________________________________________ ##STR362## m.p.No. R.sup.1 R.sup.2 R.sup.3 E B A (.degree. C.)__________________________________________________________________________I-1 Ph H H CN H A1 144-145I-2 Ph Cl H CN H A1 300<I-3 Ph H Me CN H A1 300<I-4 Ph Me H CN H A1 141-143I-5 Ph H H CN B1 A1 75-77*I-6 Ph H H CN B2 A1 viscous oilI-7 Ph CO.sub.2 Et H CN H A1 202-203I-8 Ph H H CN H A2 300<I-9 Ph H H CN H A7 124-125I-10 Ph H H CN H A8 265-267I-11 2-pyridyl H H CN H A1 290<I-12 2-pyridyl H H CN H A2 300<I-13 2-pyridyl H H CN H A3 260-267I-14 2-pyridyl H H CN H A4 300<I-15 2-pyridyl H H CN H A6 297-298I-16 2-pyridyl H H CN H A7 163-165I-17 2-pyridyl H H CN H A8 300<I-18 2-pyridyl H H CN H A9 240-245I-19 2-pyridyl H H CN H A10 261-266I-20 2-pyridyl H H CN H A11 232-234I-21 2-pyridyl H H CN H A12 284-287I-22 2-pyridyl H H CN H A13 300<I-23 2-pyridyl H H CN B7 A7 103-110*I-24 2-pyridyl H H CN B8 A1 viscous oilI-25 3-pyridyl H H CN H A1 298-300I-26 3-pyridyl H H CN H A2 158-160I-27 3-pyridyl H H CN H A7 168-169I-28 4-pyridyl H H CN H A1 251-253I-29 2-F--Ph H H CN H A1 125-126I-30 2-F--Ph H H CN H A2 281-282I-31 2-F--Ph Cl H CN H A1 281-287I-32 3-F--Ph H H CN H A2 300<I-33 4-F--Ph H H CN H A2 169-173I-34 2-Cl--Ph H H CN H A1 viscous oilI-35 2-Cl--Ph H H CN H A2 viscous oilI-36 3-Cl--Ph H H CN H A1 141-149I-37 3-Cl--Ph H H CN H A7 291-293I-38 4-Cl--Ph H H CN H A1 186-188I-39 4-Cl--Ph H H CN H A7 300<I-40 2,6-F.sub.2 --Ph H H CN H A1 267-269I-41 2,6-F.sub.2 --Ph H H CN H A2 300<I-42 2,6-F.sub.2 --Ph H H CN H A7 242-243I-43 2,6-Cl.sub.2 --Ph H H CN H A1 147-148I-44 2,6-Cl.sub.2 --Ph H H CN H A2 100-102I-45 tBu H H CN H A1 viscous oilI-46 tBu H H CN H A2 65-67I-47 2-MeO--Ph H H CN H A1 300<I-48 2-MeO--Ph H H CN H A2 300<I-49 H CO.sub.2 Et Ph CN H A1 236-237I-50 Me Ph H CN H A1 viscous oilI-51 cHex H H CN H A1 204-205I-52 1-naphthyl H H CN H A1 225-227I-53 2-thienyl H H CN H A1 146-147I-54 2-thienyl H H CN H A7 271-273I-55 Ph H H CN H A34 173.3-174.1I-56 Ph H H CN B1 A34 viscous oil*I-57 Ph H H CN B7 A1 140-141*I-58 Ph H H CN B8 A1 50-51*I-59 Ph H H CN CO.sub.2.sup.t Bu A1 viscous oilI-60 tBu CO.sub.2 Me H CN H A1 105-106I-61 tBu CO.sub.2 Me H CN B7 A1 125-126I-62 Ph H H CN B7 A2 viscous oilI-63 2,6-F.sub.2 --Ph H H CN B8 A2 200-201I-64 Ph H H CN B6 A2 viscous oilI-65 2,6-F.sub.2 --Ph H H CN Na 2,6-(MeO).sub.2 --Ph 300<I-66 2,6-F.sub.2 --Ph H H CN Na 2-CF.sub.3 O--Ph 282.8-287.2I-67 2,6-F.sub.2 --Ph H H CN Na 2-MeO--Ph 300<I-68 2,6-F.sub.2 --Ph H H CN H 2-CF.sub.3 O--Ph 157.9-160.1I-69 2-pyridyl H H CN B8 A7 118-119*I-70 2,6-F.sub.2 --Ph H H CN B7 A2 viscous oilI-71 Ph H H CN H 2-Cl--Ph 108-109I-72 Ph H H CN H 2,6-F.sub.2 --Ph 167-168I-73 Ph H H CN H 2,6-Cl.sub.2 --Ph 170-171I-74 Ph H H CN H 2-CF.sub.3 --Ph viscous oilI-75 Ph H H CN H 1-naphthyl 137-138I-76 Ph Ph H CN H A2 145-147I-77 Ph H H CN H 2-Cl-4-F--Ph 94-95I-78 Ph H H CN B35 A2 164-165I-79 2,6-F.sub.2 --Ph H H CN H 2-Me--Ph 113.1-119.8I-80 2,6-F.sub.2 --Ph H H CN H 2-Cl-6-F--Ph 144-146I-81 2,6-F.sub.2 --Ph H H CN H 2-NO.sub.2 --Ph 176-179I-82 2,6-F.sub.2 --Ph H H CN H 2-AcO--Ph vitreous stateI-83 2,6-F.sub.2 --Ph H H CN H 2,6-Me--Ph vitreous stateI-84 2-pyridyl H H CN H 2,6-F.sub.2 --Ph 188-189I-85 2-pyridyl H H CN H 2,6-Cl.sub.2 --Ph 278-280I-86 2-pyridyl H H CN H 2-NO.sub.2 --Ph 285-287I-87 2-pyridyl H H CN H 2-MeO--Ph 275-276I-88 2-pyridyl H H CN H 2-CO.sub.2 Me--Ph 248-249I-89 2-pyridyl H H CN B7 2-Cl--Ph 124-125I-90 2-pyridyl H H CN Na 2-Cl--Ph 278-280I-91 2-pyridyl H H CN H pyridin-2-yl 216-217I-92 2-pyridyl H H CN CO.sup.n C.sub.17 H.sub.35 A7 58-59I-93 t-Bu CO.sub.2 Me H CN H 2-Cl-4-F--Ph 114-115I-94 t-Bu CO.sub.2 Me H CN B7 A2 105-106I-95 t-Bu CO.sub.2 Me H CN H A2 102-103I-96 t-Bu H H CN B7 A2 viscous oilI-97 t-Bu H H CN B7 A2 viscous oil.sup.#1I-98 t-Bu NO.sub.2 H CN B7 A2 viscous oilI-99 t-Bu Br H CN B7 A2 viscous oilI-100 t-Bu CN H CN H A2 178-180I-101 t-Bu CN H CN CO.sub.2.sup.t Bu A2 vitreous stateI-102 t-Bu CN H CN CO.sub.2.sup.t Bu A2 201-202.5.sup.#2I-103 t-Bu CN H CN CO.sub.2 Ph A2 vitreous stateI-104 t-Bu Cl H CN B7 A2 viscous oilI-105 t-Bu CO.sub.2 Me H CN CO.sub.2.sup.i Bu A2 155.8-156.9I-106 t-Bu Cl H CN H A2 viscous oilI-107 t-Bu NO.sub.2 H CN H A2 87-88I-108 t-Bu CO.sub.2.sup.n Hex H CN H A2 vitreous stateI-109 t-Bu CO.sub.2 Me H CN B8 A2 152.1-153.5I-110 t-Bu Me H CN H A2 vitreous stateI-111 t-Bu CO.sub.2 Me H CN CO.sup.n C.sub.17 H.sub.35 A14 viscous oilI-112 t-Bu CO.sub.2 Me H CN B7 A14 viscous oilI-113 t-Bu CO.sub.2 Me H CN H A14 101-102I-114 t-Bu Me H CN B7 A2 vitreous stateI-115 t-Bu CO.sub.2 Me H CN B7 A3 131-132I-116 t-Bu CO.sub.2 Me H CN Me A2 166-167*I-117 t-Bu CO.sub.2 Me H CN B3 A14 viscous oilI-118 t-Bu CO.sub.2 Me H CN H A21 152.6-154I-119 t-Bu CO.sub.2 Me H CN CO.sup.n C.sub.9 H.sub.19 A3 viscous oilI-120 t-Bu CO.sub.2 Me H CN B7 A15 125-127*I-121 t-Bu CO.sub.2 Me H CN H A15 138-139I-122 t-Bu CO.sub.2 Me H CN B7 A21 viscous oilI-123 t-Bu CO.sub.2 Me H CN CO.sup.n C.sub.5 H.sub.11 A21 viscous oilI-124 t-Bu CO.sub.2 Me H CN CO.sup.n C.sub.5 H.sub.11 A21 viscous oil.sup.#3I-125 H H 2,6-F.sub.2 --Ph CN H A2 157.4-162.4I-126 H Ph H CN H A1 vitreous stateI-127 H t-Bu H CN B7 A2 vitreous stateI-128 H t-Bu H CN H A2 vitreous stateI-129 Ph H H CO.sub.2 Me H A1 158-160I-130 Ph H H CO.sub.2 Me B7 A2 viscous oilI-131 2,6-F.sub.2 --Ph H H CO.sub.2 Me H A2 248-250I-132 2,6-F.sub.2 --Ph H H COMe H A2 vitreous stateI-133 2,6-F.sub.2 --Ph H H CO.sub.2 CH.sub.2 CH.dbd.CH.sub.2 H A2 vitreous stateI-134 2,6-F.sub.2 --Ph H H Br H A2 123-125I-135 2,6-F.sub.2 --Ph H H Br B7 A2 vitreous stateI-136 2-pyridyl H H CN B7 A37 86-94.sup.#4I-137 2-pyridyl H H CN B7 A10 92-93I-138 2-pyridyl Cl H CN B7 A7 viscous oil*__________________________________________________________________________ *: Eform or Zform .sup.#1 : geometric isomer of I96 .sup.#2 : geometric isomer of I101 .sup.#3 : geometric isomer of I123 .sup.#4 : mixture of E/Z = 2/1
TABLE 16__________________________________________________________________________ ##STR363## m.p.No. R E B A (.degree. C.)__________________________________________________________________________II-1 Ph CN H A1 200-205II-2 2-Cl--Ph CN H A2 137-138II-3 t-Bu CN H A2 151-153II-4 t-Bu CN B3 A2 147-150*II-5 t-Bu CN B7 A2 89.5-92*II-6 t-Bu CN H A1 viscous oil*II-7 t-Bu CN B7 A1 viscous oil*II-8 t-Bu CN H 2,6-F.sub.2 --Ph 90-92.5II-9 t-Bu CN H 2-Cl--Ph 96.2-98.6II-10 t-Bu CN B6 A2 vitreous state*II-11 t-Bu CN B5 A2 viscous oilII-12 t-Bu CN B8 A2 viscous oilII-13 t-Bu CN SO.sub.2 (4-Cl--Ph) A2 vitreous state*II-14 t-Bu CN H 2,6-Cl.sub.2 --Ph 150.3-151.7II-15 t-Bu CN H 2-CF.sub.3 --Ph 71.9-79.6II-16 t-Bu CN H A3 viscous oilII-17 t-Bu CN B7 A3 viscous oil*II-18 t-Bu CN CO.sub.2 Et A2 viscous oilII-19 t-Bu CN CO.sub.2 CH.sub.2 Ph A2 viscous oilII-20 t-Bu CN CONMe.sub.2 A2 136.7-138.2II-21 t-Bu CN CH.sub.2 CO.sub.2 Me A2 viscous oilII-22 t-Bu CN PO(OEt).sub.2 A2 viscous oilII-23 2-pyridyl CN H A2 184.5-188.5II-24 2-pyridyl CN H A7 210.3-218.8II-25 2-pyridyl CN B7 A7 162.7-167*II-26 2-pyridyl CN B7 A2 vitreous state*II-27 2-pyridyl CN H A3 148-151II-28 2-pyridyl CN B7 A3 vitreous state*II-29 2-pyridyl CN H A35 188-193II-30 2-pyridyl CN B7 A35 200.5-202.5*II-31 2-pyridyl CN H A36 viscous oilII-32 2-pyridyl CN B7 A36 viscous oilII-33 c-Hex CN H A2 126.5-128.1II-34 c-Hex CN H 2,6-F.sub.2 --Ph 110.9-112.7II-35 c-Hex CN B7 2,6-F.sub.2 --Ph 111.2-117.4*II-36 c-Hex CN B7 A2 viscous oil*II-37 2,6-F.sub.2 --Ph CN H A2 176.8-178.2II-38 2,6-F.sub.2 --Ph CN B7 A2 95.9-98.0*II-39 2-Cl--Ph CN H A2 172.9-175.2II-40 t-Bu CN B35 A2 vitreous stateII-41 t-Bu CN B35 A2 vitreous state.sup.#4II-42 t-Bu CN B36 A2 vitreous stateII-43 t-Bu CN H A13 168-173II-44 t-Bu CN B28 A2 vitreous stateII-45 t-Bu CN B30 A2 vitreous stateII-46 t-Bu CN B30 A2 vitreous state.sup.#5II-47 t-Bu CN CO(2-Me--Ph) A2 vitreous stateII-48 t-Bu CN B38 A2 vitreous stateII-49 t-Bu CN B37 A2 vitreous stateII-50 t-Bu CN nicotinoyl A2 vitreous stateII-51 t-Bu CN B40 A2 vitreous stateII-52 t-Bu CN CO.sub.2.sup.i Bu A2 viscous oilII-53 t-Bu CN CO.sub.2 Ph A2 viscous oilII-54 t-Bu CN B41 A2 viscous oilII-55 t-Bu CN CO.sub.2.sup.n Hex A2 viscous oilII-56 t-Bu CN H 3-Cl--Ph 89.7-91.1II-57 t-Bu CN H 3-F--Ph 63.7-64.4II-58 t-Bu CN H 2-Br--Ph 86-87II-59 t-Bu CN H 2-I--Ph vitreous stateII-60 t-Bu CN H 2-Cl-6-F--Ph 109.6-110.6II-61 t-Bu CN CO(2-MeS--Ph) A2 vitreous stateII-62 t-Bu CN H 2-MeS--Ph 120.6-122.1II-63 t-Bu CN H A22 113-118II-64 t-Bu CN B7 A22 98-99.5*II-65 t-Bu CN B15 A22 viscous oilII-66 t-Bu CN B38 A13 viscous oilII-67 t-Bu CN B39 A2 vitreous stateII-68 t-Bu CN CO(4-Cl--Ph) A2 vitreous stateII-69 t-Bu CN CO(3-Cl--Ph) A2 vitreous stateII-70 t-Bu CN B7 2,6-F.sub.2 --Ph viscous oilII-71 t-Bu CN B8 2,6-F.sub.2 --Ph viscous oilII-72 t-Bu CN B6 2,6-F.sub.2 --Ph 150.2-151.3II-73 t-Bu CN CO.sub.2.sup.n Pr A2 viscous oilII-74 t-Bu CN CO.sub.2.sup.n Bu A2 viscous oilII-75 t-Bu CN B6 A13 viscous oilII-76 t-Bu CN CO.sub.2 CH.sub.2 CCl.sub.3 A2 viscous oilII-77 t-Bu CN CO(2-Cl--Ph) A2 vitreous stateII-78 t-Bu CN CO(3-CF.sub.3 --Ph) A2 vitreous stateII-79 t-Bu CN CO(4-CF.sub.3 --Ph) A2 vitreous stateII-80 t-Bu CN CO(3-NO.sub.2 --Ph) A2 vitreous stateII-81 t-Bu CN CO(2-Cl-6-F--Ph) A2 vitreous stateII-82 t-Bu CN CO.sub.2.sup.c Pen 2,6-F.sub.2 --Ph vitreous stateII-83 t-Bu CN 3-Cl-pivaloyl A2 viscous oil*II-84 t-Bu CN CO.sub.2.sup.i Pr A2 viscous oilII-85 t-Bu CN CO.sub.2 CH.sub.2 CH.sub.2 Cl A2 viscous oilII-86 t-Bu CN CO.sub.2 CHClCH.sub.3 A2 viscous oilII-87 t-Bu CN CO.sup.i Pr A2 viscous oilII-88 t-Bu CN isonicotinoyl A2 viscous oilII-89 t-Bu CN picolinoyl A2 viscous oilII-90 t-Bu CN CO(4-Me--Ph) A2 viscous oilII-91 t-Bu CN CO(4-NO.sub.2 --Ph) A2 viscous oilII-92 t-Bu CN methacryloyl A2 viscous oilII-93 t-Bu CN B15 A2 vitreous stateII-94 t-Bu CN PhCH.sub.2 A2 viscous oilII-95 t-Bu CN Me A2 136.5-138II-96 t-Bu CN CBrF.sub.2 A2 84-86.5II-97 t-Bu CN CO.sup.n Pr A2 viscous oilII-98 t-Bu CN CO.sup.i Bu A2 viscous oilII-99 t-Bu CN B43 A2 vitreous stateII-100 t-Bu CN PhCOCH.sub.2 A2 148-152*II-101 t-Bu CN B42 A2 128-129.5*II-102 t-Bu CN H A14 98-99II-103 t-Bu CN H A16 viscous oilII-104 t-Bu CN B7 A16 viscous oil*II-105 t-Bu CN cinnamoyl A2 vitreous stateII-106 t-Bu CN H A23 109-112II-107 t-Bu CN B7 A23 120-122.5II-108 t-Bu CN B7 A14 viscous oilII-109 t-Bu CN B7 A14 viscous oil.sup.#6II-110 t-Bu CN CO.sup.n C.sub.17 H.sub.35 A14 viscous oilII-111 t-Bu CN PhCH.sub.2 CO A2 viscous oilII-112 t-Bu CN B7 A17 viscous oilII-113 t-Bu CN H A17 140-143II-114 t-Bu CN H A24 115-117II-115 t-Bu CN CO.sub.2.sup.i Bu A24 vitreous stateII-116 t-Bu CN B7 A2 69.5-73.5.sup.#7II-117 t-Bu CN H A25 107-109II-118 t-Bu CN B7 A25 viscous oilII-119 t-Bu CN H A31 116-117II-120 t-Bu CN CO.sub.2 (4-Me--Ph) A31 92-93II-121 t-Bu CN H A26 133.2-135.4II-122 t-Bu CN B7 A26 133.9-145II-123 t-Bu CN H A27 46-47II-124 t-Bu CN H A28 168-169II-125 t-Bu CN H A29 94.7-95.4II-126 t-Bu CN B8 A29 viscous oilII-127 t-Bu CN B8 A29 viscous oil.sup.#8II-128 t-Bu CN H A32 133.9-134.4II-129 t-Bu CN H A33 220-230II-130 2,6-F.sub.2 --Ph CN H 2-6-F.sub.2 --Ph 138-143II-131 2-pyridyl CN B7 A18 115-145II-132 2-pyridyl CN H A18 176-178II-133 2-pyridyl CN H A9 191.5-195II-134 2-pyridyl CN B7 A9 101-103II-135 2-pyridyl CN H A8 211-216II-136 2-pyridyl CN H A10 189-193II-137 2-pyridyl CN CO.sub.2 (4-F--Ph) A10 137-142II-138 2-pyridyl CN H A24 188-191.5II-139 2-pyridyl CN B7 A24 160-163.5II-140 2-pyridyl CN B7 A30 123-125II-141 2-pyridyl CN H A30 165-166II-142 2-pyridyl CN H A13 149.5-151II-143 NMePh CN H A7 161.5-164II-144 NMePh CN B7 A7 120-123II-145 NMePh CN H A2 vitreous stateII-146 NMePh CN B7 A2 vitreous stateII-147 1-piperidyl CN B3 A2 165.5-169II-148 1-piperidyl CN H A2 151-153II-149 1-piperidyl CN H A7 187-190II-150 1-piperidyl CN B8 A7 viscous oilII-151 1-piperidyl CN B8 A2 120-121.5II-152 1-piperidyl CN B6 A2 viscous oilII-153 1-naphthyl CN H A2 161-163II-154 1-naphthyl CN B7 A2 vitreous stateII-155 t-Bu CO.sub.2 Me H A2 viscous oilII-156 1-Me-1-.sup.c Hex PO(OEt).sub.2 H A1 vitreous stateII-157 t-Bu CO.sub.2 Et H A1 viscous oilII-158 t-Bu CO.sub.2 Et B7 A1 viscous oilII-159 1-Me-1-.sup.c Hex CN H A2 vitreous stateII-160 n-Pen CN H A2 73-75II-161 t-Bu CN B8 A32 108-112II-162 t-Bu CN H A1 viscous oilII-163 t-Bu CO.sub.2 Me H A1 89-92II-164 t-Bu SO.sub.2 Ph H A1 145-148II-165 t-Bu SO.sub.2 Ph B7 A1 122-123II-166 t-Bu SO.sub.2 Ph B7 A1 .sup. 152-153.sup.#14II-167 t-Bu CO.sub.2 Me B7 A1 viscous oilII-168 t-Bu CO.sub.2 Me B7 A2 76-78II-169 t-Bu CO.sub.2 CH.sub.2 CH.dbd.CH.sub.2 H A2 viscous oilII-170 t-Bu CO.sub.2 CH.sub.2 CH.dbd.CH.sub.2 B7 A2 viscous oilII-171 1-Me-1-.sup.c Hex CN B7 A2 vitreous stateII-172 n-Pen CN B7 A2 vitreous stateII-173 1-Me-1-.sup.c Hex CN CH.sub.2 O(CH.sub.2).sub.2 OCH.sub.3 A2 97-98*II-174 t-Bu 5-Me-1,3,4- H A1 vitreous state oxadiazol-2-ylII-175 t-Bu 5-Me-1,3,4- H A1 vitreous state oxadiazol-2-ylII-176 t-Bu Bu H A2 viscous oilII-177 t-Bu CN B6 A13 104-107*II-178 t-Bu 5-Me-1,3,4- B7 A1 134-137 oxadiazol-2-ylII-179 t-Bu 5-Me-1,3,4- B7 A1 .sup. 114-116.sup.#15 oxadiazol-2-ylII-180 t-Bu 5-Me-1,3,4- B7 A1 86-90* thiadiazol-2-yl__________________________________________________________________________ *: Eform or Zform .sup.#4 : geometric isomer of II40 .sup.#5 : geometric isomer of II45 .sup.#6 : geometric isomer of II108 .sup.#7 : geometric isomer of II5 .sup.#8 : geometric isomer of II126 .sup.#14 : geometric isomer of II165 .sup.#15 : geometric isomer of II178
TABLE 17______________________________________ ##STR364## m.p.No. R E B A (.degree. C.)______________________________________III-1 Ph CN B4 A1 viscous oil*III-2 Ph CN B5 A1 40-41*III-3 t-Bu CN B1 A1 151-152*III-4 t-Bu CN B4 A1 77-79*III-5 t-Bu CN B6 A2 55-61*III-6 t-Bu CN B7 A2 viscous oil*III-7 2-pentyl CN B1 A1 viscous oilIII-8 4-.sup.t Bu--Ph CN B1 A5 viscous oilIII-9 t-Bu CN Na A2 165-174III-10 t-Bu CN B9 A2 viscous oilIII-11 t-Bu CN B10 A2 185-186*III-12 t-Bu CN B11 A2 viscous oilIII-13 2-NO.sub.2 --Ph CN B9 A1 168-171*III-14 1-naphthyl CN B9 A7 136-138*III-15 t-Bu CN B7 A2 viscous oil.sup.#9III-16 Ph CN B4 A1 .sup. solid.sup.#10III-17 t-Bu CN B4 A1 .sup. viscous oil.sup.#11III-18 2-Cl-6-F--Ph CN B7 A2 152-153III-19 2,6-F.sub.2 --Ph CN B7 A2 vitreous state*III-20 Ph CN B5 A1 .sup. 105-107.sup.#12III-21 Ph CN B7 A2 viscous oil______________________________________ *: Eform or Zform, .sup.#9 : geometric isomer of III6, .sup.#10 : geometric isomer of III1, .sup.#11 : geometric isomer of III4, .sup.#12 : geometric isomer of III2
TABLE 18__________________________________________________________________________ ##STR365##No. G E B A m.p. (.degree. C.)__________________________________________________________________________IV-1 2-CF.sub.3 CN H A1 viscous oilIV-2 3-CF.sub.3 CN H A1 159-163IV-3 3-CF.sub.3 CN B1 A1 174-175IV-4 4-CF.sub.3 CN H A1 176-179IV-5 4-CF.sub.3 CN B1 A1 viscous oilIV-6 2-CF.sub.3 CN CSNMe.sub.2 A1 viscous oilIV-7 3(1-CN-1-Me)-Et CN H A1 viscous oilIV-8 3(1-CN-1-Me)-Et CN B1 A1 148-155IV-9 3-OPh CN H A1 103-110IV-10 3-OPh CN B7 A1 viscous oilIV-11 4-OPh CN H A1 148-150IV-12 4-OPh CN B7 A1 viscous oilIV-13 4-Et CN H A1 148-149IV-14 4-Et CN B7 A1 81-82IV-15 4-Et CN B5 A1 viscous oilIV-16 4-i-Pr CN H A1 126-127IV-17 4-i-Pr CN B7 A1 105-l06IV-l8 4-t-Bu CN H A1 117-118IV-19 4-t-Bu CN B1 A1 viscous oilIV-20 4-OCF.sub.3 CN H A1 128-129IV-21 4-OCF.sub.3 CN B7 A1 96-99IV-22 3,4-methylene- CN H A1 129-131 dioxyIV-23 3,4-methylene- CN B7 A1 viscous oil dioxyIV-24 4-t-Bu CN B7 A2 viscous oilIV-25 4-t-Bu CN B15 A2 viscous oilIV-26 4-t-Bu CN H A2 139-140IV-27 4-t-Bu CN B7 A13 87-88IV-28 4-t-Bu CN H A13 141-142IV-29 4-t-Bu CN B8 A2 vitreous stateIV-30 4-t-Bu CN H A19 169.5-173IV-31 4-t-Bu CN H A20 vitreous stateIV-32 4-t-Bu CN B7 A20 146-148IV-33 4-t-Bu CN B15 A14 viscous oilIV-34 4-t-Bu CN B7 A19 vitreous stateIV-35 4-t-Bu CN B7 A1 viscous oil*IV-36 4-t-Bu CN B8 A1 viscous oilIV-37 4-t-Bu CN H A24 vitreous stateIV-38 4-t-Bu CN B8 A24 vitreous stateIV-39 4-t-Bu CN CO.sub.2 Et A1 viscous oilIV-40 4-t-Bu CN CO.sub.2.sup.i Bu A1 viscous oilIV-41 4-t-Bu CN COCO.sub.2 CH.sub.3 A1 viscous oilIV-42 4-s-Bu CN H A2 107-108IV-43 4-s-Bu CN B15 A2 77-85IV-44 4-i-Pr CN B15 A1 100-101IV-45 4-i-Pr CN B15 A2 viscous oilIV-46 4-i-Pr CN H A2 98-99IV-47 4-i-Pr CN B8 A2 viscous oilIV-48 4-i-Pr CN CO(4-NO.sub.2 --Ph) A2 vitreous stateIV-49 4-Et CN B15 A1 viscous oilIV-50 4-Ph CN H A1 vitreous stateIV-51 4-Ph CN H A2 vitreous stateIV-52 4-Ph CN H A12 vitreous stateIV-53 4-Ph CN H A13 167-169IV-54 3,4-Cl.sub.2 CN H A1 vitreous stateIV-55 4-Cl CN H A1 vitreous stateIV-56 2-F-4-CF.sub.3 CN H A2 vitreous stateIV-57 2-F-4-CF.sub.3 CN B7 A2 vitreous stateIV-58 2-F-4-CF.sub.3 CN B15 A2 vitreous stateIV-59 4-NO.sub.2 CN H A1 186-188IV-60 4-MeO CN H A1 108-110IV-61 4-MeO CN B15 A1 viscous oil*IV-62 4-i-PrO CN H A1 127-131IV-63 4-i-PrO CN H A2 141.4-148.3IV-64 4-i-PrO CN B15 A1 viscous oilIV-65 4-i-PrO CN B15 A2 viscous oilIV-66 4-i-PrO CN B6 A2 viscous oilIV-67 4-n-BuO CN H A1 101-104IV-68 4-n-BuO CN B15 A1 75-70IV-69 4-n-BuO CN H A2 104.6-105.4IV-70 4-n-BuO CN B8 A1 77.1-80.7IV-71 4-n-BuO CN B15 A2 viscous oilIV-72 4-t-amyl CN B15 A2 viscous oilIV-73 4-allyloxy CN H A1 vitreous stateIV-74 4-allyloxy CN B15 A1 vitreous stateIV-75 4-(Cl.sub.2 C.dbd.CHCH.sub.2 O) CN H A1 vitreous stateIV-76 4-(Cl.sub.2 C.dbd.CHCH.sub.2 O) CN B15 A1 vitreous stateIV-77 4-(ClCCCH.sub.2 O) CN H A1 vitreous stateIV-78 4-PhCH.sub.2 O CN H A1 152.9-154.7IV-79 4-PhCH.sub.2 O CN H A2 189-190.5IV-80 4-PhCH.sub.2 O CN B15 A2 123-129IV-81 4-MeOCH.sub.2 O CN H A1 130.4-131.7IV-82 4-CF.sub.3 CH.sub.2 O CN H A1 100-103IV-83 4-pivaloyl CN B15 A2 vitreous stateIV-84 4-pivaloyl CN H A2 vitreous stateIV-85 4-Me.sub.2 NCO.sub.2 CN H A2 vitreous stateIV-86 4-Me.sub.2 NCO.sub.2 CN B15 A2 vitreous stateIV-87 4-Me.sub.2 NCO.sub.2 CN B7 A2 vitreous stateIV-88 4-t-Bu PO(OEt).sub.2 H A1 87-88IV-89 4-t-Bu PO(OEt).sub.2 B1 A1 121-124IV-90 H Br H A1 74.5-75.5IV-91 H CO.sub.2 Et H A1 viscous oilIV-92 H Br B7 A1 viscous oilIV-93 4-t-Bu PO(OEt).sub.2 H A2 viscous oilIV-94 4-t-Bu CN COCO.sub.2 Et A1 viscous oilIV-95 4-t-Bu CN CO.sub.2.sup.i Bu A2 viscous oilIV-96 4-t-Bu CN CO.sub.2.sup.i Bu A13 104-105IV-97 4-t-Bu SO.sub.2 Ph H A1 143-145IV-98 H CO.sub.2 Et B7 A1 viscous oilIV-99 4-t-Bu CN B3 A1 viscous oilIV-100 4-t-Bu CN B19 A1 vitreous stateIV-101 4-t-Bu CN CO(4-CO.sub.2 Me--Ph) A2 vitreous stateIV-102 4-t-Bu CN CO(4-CO.sub.2 Me--Ph) A13 vitreous stateIV-103 4-t-Bu CO.sub.2 Me H A2 88-89IV-104 4-t-Bu CO.sub.2 Me H A1 123-124IV-105 4-t-Bu CO.sub.2 Me B7 A1 77-78IV-106 4-t-Bu CO.sub.2 Me B7 A2 viscous oilIV-107 4-t-Bu SO.sub.2 Ph B7 A1 98-99IV-108 4-t-Bu SO.sub.2 Ph B7 A1 130-131.sup.#13IV-109 4-t-Bu CN B3 A2 71-72*IV-110 4-CHF.sub.2 O CN H A2 vitreous stateIV-l11 4-CHF.sub.2 O CN B15 A2 vitreous stateIV-112 4-CHF.sub.2 O CN B7 A2 vitreous stateIV-113 4-CH.sub.3 CONH CN H A2 247.9-251.9IV-114 4-CH.sub.3 CONH CN B7 A2 82.1-84.3IV-115 4-CO.sub.2 Me CN H A2 151-152IV-116 4-CO.sub.2 Me CN B7 A2 viscous oil*IV-117 4-vinyl CN H A2 vitreous stateIV-118 4-t-Bu CN B15 A1 78-82IV-119 4-t-Bu CN methacryloyl A1 viscous oil*IV-120 4-t-Bu CN COCH.dbd.(CH.sub.3).sub.2 A1 viscous oilIV-121 4-t-Bu CN B33 A1 viscous oilIV-122 4-t-Bu CN CH.sub.2 OCH.sub.2 Ph A1 viscous oilIV-123 4-t-Bu CN B24 A1 viscous oilIV-124 H Cl H A1 48-49IV-125 4-t-Bu 5-Me-1,3,4- H A1 149-151 oxadiazol- 2-ylIV-126 4-SMe CN H A2 154-156IV-127 4-SMe CN B7 A2 viscous oil*IV-128 4-SOMe CN H A2 vitreous stateIV-129 4-t-Bu CN B33 A2 viscous oilIV-130 4-t-Bu CN B3 A13 111-112*IV-131 4-t-Bu CN B7 A3 viscous oilIV-132 4-t-Bu CN B3 A3 viscous oilIV-133 4-t-Bu CN COCH.sub.2 (4-OMe--Ph) A1 117-121IV-134 4-SO.sub.2 Me CN B7 A2 vitreous state*IV-135 4-SOMe CN B7 A2 vitreous state*IV-136 4-OCH.sub.2 Ph-3-Cl CN H A2 vitreous stateIV-137 4-OPr.sup.i -3-Cl CN H A2 vitreous stateIV-138 4-OBu.sup.i -3-Cl CN H A2 vitreous stateIV-139 4-t-Bu CN B8 A3 viscous oilIV-140 4-t-Bu CN B7 2-Cl-4-CF.sub.3 - 90-91 thiazol-5-yl__________________________________________________________________________ *E-form or Zform .sup.#13 geometric isomer of IV107
TABLE 19__________________________________________________________________________ ##STR366##No. Q R E B A m.p. (.degree. C.)__________________________________________________________________________V-1 Q9 1-Ph CN H A1 148.7-151.3V-2 Q9 1-Ph CN H A2 156-157V 3 Q9 5-Me-1-.sup.i Pr CN H A2 78-80V 4 Q9 5-Me-1-.sup.i Bu CN B7 A2 84-89*V 5 Q9 5-Me-1-.sup.s Bu CN B7 A2 99-105V-6 Q9 5-Me-1-.sup.i Bu CN H A2 113-114V-7 Q9 5-Me-1-.sup.s Bu CN H A2 75-80V-8 Q9 1-t-Bu CN B7 A2 vitreous state*V-9 Q9 1-t-Bu CN H 2,6-F.sub.2 --Ph 111-113V-10 Q9 1-t-Bu CN H A2 127-129V-11 Q9 1-pyridin- CN H A2 156.4-158.1 2-ylV-12 Q9 1-pyridin CN B15 A2 vitreous state* 2-ylV-13 Q9 1-pyridin- CN B7 A2 vitreous state* 2-ylV-14 Q10 1-Ph CN B7 A2 130-131V-15 Q10 1-Ph CN H A2 207-208V-16 Q10 1-t-Bu CN B7 A2 viscous oilV-17 Q10 1-t-Bu CN H A2 viscous oilV-18 Q11 1-Me-3-.sup.t Bu CN H A2 vitreous stateV-19 Q11 1-Me-3-.sup.t Bu CN B7 A2 119-124V-20 Q12 Ph CN H A2 247-253V-21 Q12 Ph CN B7 A2 147.5-148.5*V-22 Q12 Ph CN SO.sub.2 (4-.sup.t Bu--Ph) A2 174-176.5V-23 2-naphthyl -- CN B1 A1 viscous oilV-24 2-naphthyl -- CN H A1 140.1-141.1V-25 2-naphthyl -- CN B7 A1 viscous oilV-26 Q13 -- CN H A2 121-122V-27 Q1 5-Cl CN H A2 160 (decompo- sition)V-28 Q1 5-Cl CN B7 A2 79.5-81V-29 Q2 4-Ph CN H A1 231-232V-30 Q2 4-t-Bu CN H A1 218-219V-31 Q3 3-Ph CN H A1 243-245V-32 Q4 Ph CN H A1 255.8-256.8V-33 Q4 Ph CN B1 A1 187-190V-34 Q5 t-Bu CN H A2 158-160V-35 Q6 t-Bu CN H A2 215-216V-36 Q7 5-CF.sub.3 CN H A1 184-185V-37 Q7 5-CF.sub.3 CN H A2 211-212V-38 Q7 5-PhCH.sub.2 O CN H A1 220-221V-39 Q8 4,6-(MeO).sub.2 CN H A1 149-155V-40 Q14 t-Bu CN H A1 137.9-143.7V-41 Q14 t-Bu CN B7 A1 vitreous stateV-42 Q14 t-Bu CN H A2 127.5-128.9V-43 Q14 t-Bu CN B7 A2 vitreous stateV-44 Q14 t-Bu CN B33 A2 vitreous stateV-45 Q14 t-Bu CN H 2,6-F.sub.2 --Ph 105.6-108.1V-46 Q14 t-Bu CN B7 2,6-F.sub.2 --Ph viscous oilV-47 Q14 Ph CN H A2 113.0-114.9V-48 Q14 Ph CN B7 A2 vitreous stateV-49 Q14 Ph CN B15 A2 vitreous stateV-50 Q14 2-Cl--Ph CN H A1 125.5-127.5V-51 Q14 2-Cl--Ph CN B7 A1 104.0-107.5V-52 Q14 2-Cl--Ph CN H A2 142.4-143.6V-53 Q14 2-Cl--Ph CN B15 A2 vitreous stateV-54 Q14 2-Cl--Ph CN B7 A2 vitreous stateV-55 Q14 2,6-F.sub.2 --Ph CN H A2 136.3-164.7V-56 Q14 2,6-F.sub.2 --Ph CN B15 A2 vitreous stateV-57 Q14 2,6-F.sub.2 --Ph CN B7 A2 vitreous stateV-58 Q14 PhCH.sub.2 CN H A2 113.2-114.3V-59 Q14 PhCH.sub.2 CN B15 A2 vitreous stateV-60 Q14 PhCH.sub.2 CN B7 A2 vitreous stateV-61 Q14 2-Cl--Ph CN H 2-MeO--Ph 131.4-132.8V-62 Q14 2-Cl--Ph CN CO.sub.2 -2-Oct 2-MeO--Ph viscous oilV-63 Q14 2-Cl--Ph CN B44 2-MeO--Ph vitreous stateV-64 Q14 2-Cl--Ph CN H 2,6-F.sub.2 --Ph 155.1-157.9V-65 Q14 2-Cl--Ph CN B45 2,6-F.sub.2 --Ph 159.3-160.3V-66 Q14 2-Cl--Ph CN H A7 150-152V-67 Q14 2-Cl--Ph CN SO.sub.2 (3-Cl--Ph) A7 132-133V-68 Q14 PhMe.sub.2 C CN H A2 vitreous stateV-69 Q14 PhMe.sub.2 C CN B7 A2 vitreous stateV-70 Q14 PhMe.sub.2 C CN COCH.sub.2 OMe A2 vitreous stateV-71 Q15 Ph CN H A1 151-153V-72 Q16 3-CN--Ph CN H A1 174-175V-73 Q17 5-CO.sub.2 Et CN B7 A2 viscous oilV-74 Q18 3-pyridin- CN H A2 219 (decompo- 2-yl sition)V-75 Q19 5-Me-2-Ph CN H A2 181-182V-76 Q19 5-Me-2-Ph CN B7 A2 viscous oilV-77 Q18 3-pyridin- CN B7 A2 vitreous state 2-ylV-78 Q18 3-pyridin- CN B46 A2 vitreous state 2-ylV-79 Q18 t-Bu CN H A2 110.4-110.8V-80 Q20 6-I CN H A2 205-208V-81 Q20 6-I CN B7 A2 137-142V-82 4-Ph- -- CN H A2 165.9-166.7 oxazol-2-ylV-83 4-Ph- -- CN B15 A2 vitreous state oxazol-2-ylV-84 4-Ph- -- CN B7 A2 vitreous state oxazol-2-ylV-85 Q19 5-Me-2-Ph CN H A7 117-118V-86 3-(2-Cl--Ph) -- CN H A2 155-156 imidazolin- 2-on-1-yl__________________________________________________________________________ *E-form or Zform
TABLE 20______________________________________ ##STR367##No. G B Y.sup.1 Y.sup.2 melting point (.degree.______________________________________ C.)VI-4 tBu B33 H Me 93.7-96.6VI-5 tBu Et Me H resinousVI-6 tBu B33 Me H resinousVI-7 tBu Me Me Me resinousVI-8 tBu Et Me Me resinousVI-9 tBu B3 Me Me resinousVI-10 tBu B3 Me Me resinous (isomer of VI-9)VI-11 tBu CH.sub.2 OCH.sub.2 Ph Me Me resinousVI-12 tBu CH.sub.2 OCH.sub.2 Ph Me Me resinous (isomer of VI-11)VI-13 tBu B24 Me Me resinousVI-14 tBu B32 Me Me resinousVI-15 tBu B32 Me Me resinous (isomer of VI-14)VI-16 tBu B33 Cl Me 66.5-67.45VI-17 tBu B33 Me Br 94.0-95.0VI-18 tBu Et H Me 133.0-135.5VI-19 tBu B33 Me Me resinous (Z-form)VI-20 tBu B33 Me Me resinousVI-21 tBu H Me H resinousVI-22 tBu H H Me resinousVI-23 tBu H Me Me resinousVI-24 tBu H Cl Me 68.0-69.0VI-25 tBu H Me Br resinousVI-26 sBu H Me Me resinousVI-27 EtMe.sub.2 C H Me Me resinousVI-28 EtMe.sub.2 C H Cl Me resinousVI-29 tBu B7 Me Me 102.2-103.8VI-30 tBu B6 Me Me resinousVI-31 tBu CO(2-MeO--Ph) Me Me resinousVI-32 tBu B26 Me Me resinousVI-33 tBu B7 C1 Me resinousVI-34 tBu COOiBu Me Me resinousVI-35 EtMe.sub.2 C B7 Me Me resinousVI-36 sBu B7 Me Me resinousVI-37 tBu CO(2-MeO--Ph) Cl Me 181.5-182.5VI-38 tBu B7 --(CH.sub.2).sub.3 -- 105.3-106.8VI-39 tBu B7 MeO Me 68.1-70.6VI-40 tBu B7 Me H resinousVI-41 tBu CO(2-Me--Ph) Cl Me 128.0-130.0VI-42 tBu CO(3-pyridyl) Me Me resinousVI-43 tBu CO(2-Cl--Ph) Me Me 133.0-134.0VI-44 tBu CO(2-Cl--Ph) Me Me 150.0-151.0 (Isomer of I-43)VI-45 tBu B7 Me Br 118.0-119.0VI-46 tBu CO(3-Cl--Ph) Me Me 143.0-145.0VI-47 tBu CO(4-Cl--Ph) Me Me 169.0-170.0VI-48 tBu B5 Me Me resinousVI-49 tBu B2 Me Me 110.6-111.8VI-50 tBu CO(2-Me--Ph) Me Me 127.0-128.0VI-51 tBu CO(3-Me--Ph) Me Me 111.0-112.0VI-52 tBu CO(4-Me--Ph) Me Me 134.5-136.0______________________________________
TABLE 21______________________________________ ##STR368## melting point .degree. C.No. B Y.sup.1 Y.sup.2 (ratio of isomer)______________________________________VII-1 H H H pale brown solidVII-2 H H Me >200 (hydrochloride)VII-3 H Me H 86.2-88.1VII-4 H Cl Me resinousVII-5 H H Cl resinousVII-6 H Cl Et resinousVII-7 H Me Me 207-210VII-8 H --(CH.sub.2).sub.3 -- resinousVII-9 Me Me Me resinousVII-10 CH.sub.2 Ph Me Me resinousVII-11 B7 Me Me 133.7-134.5 (Z-form)VII-12 B7 Me Me resinous (E-form)VII-13 B7 H Me resinous (3/2)VII-14 B7 H Cl resinous (20/1)VII-15 B7 Me H resinousVII-16 B7 Cl Me resinous (20/1)VII-17 B7 Cl Et resinous (10/1)VII-18 B6 Cl Me resinous (=3/1)VII-19 B36 Cl Me resinous (5/1)VII-20 B7 --(CH.sub.2).sub.3 -- resinous (5/1)VII-21 B15 Me Me resinous (10/1)VII-22 CO-cPen Me Me resinous (10/1)VII-23 B8 Me Me resinous (10/1)VII-24 B6 Me Me resinous (10/1)VII-25 CO(4-Me--Ph) Me Me resinous (10/1)VII-26 B40 Me Me resinous (10/1)VII-27 CO(2-MeO--Ph) Me Me resinous (10/1)VII-29 B38 Me Me resinous (10/1)VII-30 B36 Me Me resinous (10/1)VII-31 B35 Me Me resinous (10/1)VII-32 B37 Me Me resinous (10/1)VII-33 B5 Me Me resinous (10/1)VII-34 SO.sub.2 Ph Me Me resinous (10/1)VII-35 SO.sub.2 (4-Me--Ph) Me Me resinous (10/1)VII-36 SO.sub.2 (4-CF.sub.3 --Ph) Me Me resinous (10/1)VII-37 SO.sub.2 (2,4,6-Me.sub.3 --Ph) Me Me resinous (10/1)VII-38 B23 Me Me resinous (10/1)VII-39 Et Me Me resinous (7/1)VII-40 B7 H CF.sub.3 resinousVII-41 B7 H H resinous (2/1)VII-42 H Cl MeO 149.6-151.2VII-43 B7 Cl MeO resinousVII-44 H MeO Me resinousVII-45 H MeO Me resinous______________________________________
TABLE 22__________________________________________________________________________ ##STR369## meltingNo. Q R B A point .degree. C.__________________________________________________________________________VIII-1 Q21 Ph H A2 165.9-166.7VIII-2 Q21 Ph B15 A2 resinousVIII-3 4-tBu--Ph -- CH.sub.2 O(4-Cl--Ph) A1 resinousVIII-4 Q19 5-Me-2-Ph H A7 117.0-118.0VIII-5 Q7 5-CF.sub.3 H A38 74.0-77.0VIII-6 4-tBu--Ph -- B7 A48 145.0-146.0VIII-7 Q19 5-Me-2-Ph B3 A7 117.0-122.0VIII-8 Q23 cHex H A13 resinousVIII-9 Q23 tBu SO.sub.2 (3-Cl--Ph) A13 resinousVIII-10 Q23 1-naphtyl H A13 145.0-146.0VIII-11 Q8 4-Cl--Ph H A2 212.0-214.0VIII-12 Q24 2-pyridyl B7 A2 182.0-183.0VIII-13 3-Cl-4-CHF.sub.2 O--Ph -- B7 A2 resinousVIII-14 Q22 tBu CONMe.sub.2 A13 98.0-100.0VIII-15 Q24 tBu B7 A2 80.0-92.0VIII-16 Q22 2-pyridyl B7 A2 133.0-134.0VIII-17 Q19 5-Me-2-Ph B7 A7 85.0-102.0VIII-18 Q10 5-Me-1-(2-pyridyl) H A2 139.0-142.0VIII-19 Q22 1-Me-cHex H A13 98.0-99.0VIII-20 Q14 PhMe.sub.2 C B6 A13 resinousVIII-21 Q22 tBu B2 A13 resinousVIII-22 Q22 nPen H A13 resinousVIII-23 Q25 4-I H A13 177.5-178.2VIII-24 Q25 4-I B7 A2 resinousVIII-25 Q22 tBu B7 A39 resinousVIII-26 Q22 nNon H A13 resinousVIII-27 Q22 C.sub.17 H.sub.35 H A13 resinousVIII-28 Q22 cPr H A13 88.8-89.7VIII-29 Q22 cPen B6 A13 resinousVIII-30 Q22 PhMeCH H A13 resinousVIII-31 Q22 nPrMe.sub.2 C H A13 resinousVIII-32 Q25 2-pyridyl H A41 261.0-262.0VIII-33 Q25 4-COOMe B7 A2 97.0-98.0VIII-34 Q22 CH.sub.2 .dbd.CHCH.sub.2 CHMe H A13 resinousVIII-35 Q22 3-Me-cHex H A13 resinousVIII-36 Q22 4-Me-CHex H A13 resinousVIII-37 Q22 2-Me-cPr H A13 resinousVIII-38 Q22 sBu H A13 resinousVIII-39 Q26 tBu H A13 134.3-135.7VIII-40 Q22 Et.sub.2 CH H A13 74.0-75.0VIII-41 Q22 nPr.sub.2 CH H A13 resinousVIII-42 Q22 2-Me-cHex B6 A13 resinousVIII-43 Q22 cHep H A13 resinousVIII-44 Q25 2-pyridyl H A42 270.0-272.0VIII-45 Q22 2,3-(MeO).sub.2 --Ph B7 A13 resinousVIII-46 Q22 2-EtO--Ph B7 A13 131.3-132.6VIII-47 Q25 3-(2-pyridyl) H A21 resinousVIII-48 Q25 3-(2-pyridyl) B7 A14 84.0-85.0VIII-49 Q25 3-(2-pyridyl) H A43 186.9-188.3VIII-50 Q25 3-COOEt B7 A2 resinousVIII-51 Q22 2,4-Cl.sub.2 --Ph H A13 137.5-138.5VIII-52 Q22 2-Ph--Ph H A13 112.0-113.0VIII-53 Q19 2-Ph H A10 232.5-235.6VIII-54 Q19 2-Ph B7 A10 resinousVIII-55 Q25 5-(2-pyridyl) B7 A10 resinousVIII-56 Q25 3-COOiPr H A2 130.0-131.0VIII-57 Q25 3-(2-pyridyl) H 4-NH.sub.2 - 114.3-117.5 2-F--Ph HClVIII-58 Q25 3-(2-pyridyl) B7 A22 resinousVIII-59 Q25 3-(2-pyridyl) B7 A44 resinousVIII-60 Q25 3-(2-pyridyl) H A18 resinousVIII-61 Q25 3-(2-pyridyl) B7 A7 resinousVIII-62 Q25 3-CN B7 A45 resinousVIII-63 Q25 3-(2-pyridyl) B7 A49 resinousVIII-64 Q25 3-(2-pyridyl) H A50 143.2-147.6VIII-65 Q25 3-(2-pyridyl) B7 A30 116.0-117.0VIII-66 Q25 3-COOiPr B7 A45 resinousVIII-67 Q25 3-(4-pyridyl) H A45 resinousVIII-68 Q25 3-(2-pyridyl) B7 A46 140.7-144.5VIII-69 4-tBu--Ph -- B7 A42 resinousVIII-70 Q25 3-(2-thienyl) H A47 resinousVIII-71 Q22 cHep H A47 resinousVIII-72 Q22 cHep B7 A47 resinousVIII-73 4-tBu--Ph -- B6 A42 resinousVIII-74 4-tBu--Ph -- B33 A42 62.0-63.0VIII-75 Q22 tBu B33 A47 resinousVIII-76 Q27 2-pyridyl B7 A45 144.0-145.0VIII-77 Q27 2-pyridyl H A45 170.0-171.0VIII-78 Q27 2-pyridyl B7 A42 180.0-181.0VIII-79 Q28 2-pyridyl H A45 resinousVIII-80 Q28 2-pyridyl B7 A45 resinousVIII-81 Q19 5-Me-2-Ph H A47 resinousVIII-82 Q19 5-Me-2-Ph B7 A47 139.2-141.6VIII-83 Q25 3-tBu-4-COOMe B7 A47 115.0-116.0VIII-84 Q22 EtMe.sub.2 C B7 A47 resinousVIII-85 Q27 2-pyridyl H A3 139.0-140.0VIII-86 4-tBu--Ph -- B7 A49 93.6-95.2VIII-87 Q9 1-(2-pyridyl) H A47 resinousVIII-88 Q9 5-MeO-1-(2-pyridyl) H A47 resinousVIII-89 4-tBu--Ph -- H A21 123.0-124.0VIII-90 Q29 tBu B7 A47 resinousVIII-91 Q22 iBu B7 A2 73.0-74.0VIII-92 Q22 iBu H A2 62.0-63.0VIII-93 4-tBu--Ph -- B7 A14 98.0-99.0VIII-94 Q22 tBu B33 A52 92.0-93.0__________________________________________________________________________
Formulation Examples
Now, Formulation Examples of pesticides comprising the compounds of the present invention as the active ingredient are shown below, which, however, are not intended to restrict the scope of the invention. In the following Formulation Examples, "part" or "parts" are by weight.
______________________________________[Formulation Example 1] Wettable Powder:______________________________________Compound No. I-1 of the invention 50 partsZeeklite PFP (trade name, kaolin-type clay 43 partsmanufactured by Zeeklite Mining Industries,Co., Ltd.)Solpol 5050 (trade name, anionic surfactant 2 partsmanufactured by Toho Chemical Co., Ltd.)Runox 1000C (trade name, anionic surfactant 3 partsmanufactured by Toho Chemical Co., Ltd.)Carplex #80 (anti-caking agent, trade name, 2 partswhite carbon manufactured by ShionogiPharmaceutical Co., Ltd.)______________________________________
The above-mentioned components were homogeneously mixed and ground to form a wettable powder.
______________________________________[Formulation Example 2] Emulsion:______________________________________Compound No. I-1 of the invention 3 partsMethylnaphthalene 76 partsIsophorone 15 partsSolpol 3005X (trade name, mixture of 6 partsnonionic surfactant and anionic surfactantmanufactured by Toho Chemical Co., Ltd.)______________________________________
The above-mentioned components were homogeneously mixed to form an emulsion.
______________________________________[Formulation Example 3] Flowable:______________________________________Compound No. I-1 of the invention 35 partsAgrisol S-711 (trade name, nonionic surfactant 8 partsmanufactured by Kao Corp.)Runox 1000C (trade name, anionic surfactant 0.5 part.sup.manufactured by Toho Chemical Co., Ltd.)Aqueous solution of 1% Rhodopol (trade name, 20 partsthickener manufactured by Rhone-Poulenc)Ethylene glycol (freezing inhibitor) 8 partsWater 28.5 parts______________________________________
The above-mentioned components were homogeneously mixed to prepare a flowable.
______________________________________[Formulation Example 4] Granular wettable powder(Dry flowable):______________________________________Compound No. I-1 of the invention 75 partsIsoban No. 1 (trade name, anionic surfactant 10 partsmanufactured by Kuraray Isoprene ChemicalCo., Ltd.)Vanilex N (trade name, anionic surfactant 5 partsmanufactured by Sanyo Kokusaku PulpCo., Ltd.)Carplex #80 (trade name, white carbon 10 partsmanufactured by Shionogi PharmaceuticalCo., Ltd.)______________________________________
The above-mentioned components were homogeneously mixed and finely ground to form a dry flowable.
______________________________________[Formulation Example 5] Granules:______________________________________Compound No. I-1 of the invention 0.1 partBentonite 55.0 partsTalc 44.9 parts______________________________________
The above-mentioned components were homogeneously mixed and ground, to which was added a small amount of water, stirred, mixed and kneaded. The resulting mixture was granulated and dried into granules, using an extrusion granulator.
______________________________________[Formulation Example 6] Dust:______________________________________Compound No. I-1 of the invention 3.0 partsCarplex #80 (trade name, white carbon 0.5 partmanufactured by Shionogi PharmaceuticalCo., Ltd.)Clay 95 partsDiisopropyl phosphate 1.5 parts______________________________________
The above-mentioned components were homogeneously mixed and ground to form a dust.
Upon use, the wettable powder, emulsion, flowable and dry flowable are diluted from 50 to 20000 times with water, and applied in an amount of from 0.005 to 50 kg/ha in terms of the active ingredient.
Now, Formulation Examples of agents for preventing the attachment of aquatic organisms of the present invention are shown below, which, however, are not intended to restrict the scope of the invention.
______________________________________[Formulation Example 7]______________________________________Compound No. II-2 of the invention 8 partsVYHH (vinyl-type synthetic resin 7 partsmanufactured by UCC Co., Ltd.)Rosin 7 partsTricresyl phosphate 3 partsTalc 20 partsBarium sulfate 15 partsRed iron oxide 10 partsXylene 20 partsMethyl isobutyl ketone 10 parts______________________________________
The above-mentioned components were homogeneously mixed to form an agent for preventing the attachment of aquatic organisms of the invention. This agent can be used as a coating paint.
______________________________________[Formulation Example 8]______________________________________Compound No. II-2 of the invention 5 partsCR-10 (chlorine rubber resin manufactured 13 partsby Asahi Denka KK)Zinc flower 20 partsTalc 20 partsPlasticizer 2 partsRed iron oxide 10 partsXylene 30 parts______________________________________
The above-mentioned components were homogeneously mixed to form an agent for preventing the attachment of aquatic organisms of the invention. This agent can be used as a coating paint.
______________________________________[Formulation Example 9]______________________________________Compound No. II-2 of the invention 8 partsVYHH (vinyl-type synthetic resin manufactured 7 partsby UCC Co., Ltd.)Rosin 7 partsTricresyl phosphate 3 partsTalc 20 partsBarium sulfate 15 partsRed iron oxide 10 partsXylene 20 partsMethyl isobutyl ketone 10 parts______________________________________
The above-mentioned components were homogeneously mixed to form an agent for preventing the attachment of aquatic organisms the invention. This agent can be used as a coating paint.
______________________________________[Formulation Example 10]______________________________________Compound No. II-2 of the invention 5 partsCR-10 (chlorine rubber resin manufactured 13 partsby Asahi Denka KK)Zinc flower 20 partsTalc 20 partsPlasticizer 2 partsRed iron oxide 10 partsXylene 30 parts______________________________________
The above-mentioned components were homogeneously mixed to form an agent for preventing the attachment of aquatic organisms of the invention. This agent can be used as a coating paint.
TEST EXAMPLES
Now, the following Test Examples are to demonstrate the usefulness of the compounds of the present invention as pesticides.
Test Example 1
Insecticidal Test for Brown Rice Planthopper (Nilaparvata lugens Stal)
A 5% emulsion (or 25% wettable powder) of a compound of the present invention was diluted with water containing a spreading agent to give a 500 ppm solution of the compound.
The stems and leaves of rice-plants in 1/20,000 are pot were sufficiently applied with the resulting solution. After the thus-applied chemical solution was dried in air, each pot was covered with a cylindrical cover. Ten (10) second instar nymphae of brown rice planthoppers (Nilaparvata lugens) were released in each pot. After having been thus covered, the pots were stored in a thermostatic chamber. After 6 days passed, the insects in each pot were observed, and the mortality thereof was determined according to the following equation. Each compound was tested in that manner for two groups of pots.
Mortality (%)=[number of insect killed/(number of insect killed+number of living insect)].times.100
In this test, the following compounds exhibited mortality of 80% or more.
Compounds of the invention: Nos. I-2, I-18, I-19, I-23, I-30, I-31, I-32, I-35, I-39, I-42, I-44, I-58, I-59, I-62, I-63, I-70, I-72, I-80, I-106, I-114, I-123, I-137, II-1, II-2, II-3, II-5, II-6, II-12, II-15, II-23, II-25, II-26, II-28, II-33, II-34, II-36, II-37, II-38, II-39, II-43, II-44, II-46, II-53, II-54, II-55, II-61, II-66, II-73, II-74, II-75, II-76, II-80, II-83, II-84, II-85, II-86, II-87, II-88, II-89, II-91, II-92, II-93, II-97, II-98, II-111, II-114, II-116, II-134, II-136, II-137, II-154, II-155, II-159, III-1, III-2, III-4, III-6, III-15, III-16, III-17, III-18, III-19, III-21, IV-48, IV-58, V-2, V-12, V-13, V-28, V-48, V-49, V-51, V-53, V-54, V-55, V-56, V-57, V-59, V-60.
Test Example 2
Insecticidal Test for Green Rice Leafhoppers (Nephotettix cincticeps Uhler)
The stems and leaves of plants was dipped in a 500 ppm emulsion of a compound of the invention for about 10 seconds. The thus-treated stems and leaves were put into glass cylinders, into which were released adults of green rice leafhoppers (Nephotettix cincticeps) that were resistant to organic phosphorous insecticides. Each glass cylinder was covered with a perforated cover, and stored in a thermostatic chamber at 25.degree. C. After 6 days passed, the insects in each cylinder were observed, and the mortality of the insects was determined according to the same equation as in Test Example 1. Each compound was tested in that manner for two groups of cylinders. In this test, the following compounds exhibited morality of 80% or more.
Compounds of the invention: Nos. I-1, I-2, I-4, I-5, I-8, I-9, I-10, I-19, I-24, I-29, I-30, I-31, I-32, I-33, I-34, I-35, I-36, I-39, I-40, I-41, I-42, I-43, I-44, I-47, I-53, I-54, I-55, I-56, I-57, I-58, I-59, I-62, I-63, I-69, I-70, I-71, I-72, I-74, I-79, I-80, I-81, I-115, I-121, I-125, I-127, I-137, II-1, II-2, II-3, II-5, II-6, II-7, II-9, II-10, II-11, II-12, II-13, II-15, II-23, II-26, II-28, II-33, II-34, II-36, II-38, II-37, II-43, II-46, II-49, II-52, II-54, II-55, II-63, II-64, II-65, II-66, II-67, II-68, II-69, II-73, II-74, II-75, II-76, II-77, II-78, II-79, II-80, II-81, II-83, II-84, II-85, II-86, II-87, II-88, II-89, II-91, II-92, II-93, II-97, II-98, II-99, II-107, II-111, II-116, II-117, II-130, II-131, II-132, II-134, II-136, II-137, II-142, II-145, II-153, II-154, III-1, III-2, III-3, III-4, III-5, III-6, III-13, III-15, III-16, III-17, III-18, III-19, III-20, III-21, IV-32, IV-58, V-2, V-12, V-13, V-14, V-38, V-41, V-43, V-48, V-49, V-51, V-53, V-54, V-55, V-56, V-57, V-59, V-60, V-75.
Test Example 3
Insecticidal Test for Green Peach Aphids (Myzus persicae Sulzer)
Moistured filter paper was placed in each laboratory glass dish having an inner diameter of 3 cm, and a leaf cabbage having the same diameter as that of the dish was put on the filter paper. Four female, apterous adults of green peach aphids (Myzus persicae) were put on the cabbage leaf. Following day, a chemical sample (2.5 mg/cm.sup.2) was sprayed over the dishes, using a rotary sprinkler. The chemical solution herein was prepared by diluting a 5% emulsion (or 25% wetttable powder) of a compound of the invention to 500 ppm with water containing a spreading agent. After 6 days passed, the insects in each cylinder were observed, and mortality of the insects (larvae and adults) was determined according to the following equation. Each compound was tested in that manner for two groups of dishes.
Mortality (%)=[number of insect killed/(number of insect killed+number of living insect)].times.100
In this test, the following compounds exhibited mortality of 80% or more.
Compounds of the invention: Nos. I-1, I-2, I-3, I-4, I-5, I-7, I-8, I-9, I-10, I-11, I-12, I-13, I-14, I-16, I-17, I-18, I-19, I-21, I-22, I-23, I-24, I-25, I-26, I-27, I-28, I-29, I-30, I-31 I-32, I-33, I-34, I-35, I-36, I-37, I-38, I-40, I-41, I-42, I-43, I-44, I-45, I-46, I-47, I-48, I-51, I-52, I-53, I-54, I-55, I-56, I-57, I-58, I-59, I-62, I-63, I-69, I-70, I-71, I-72, I-73, I-74, I-76, I-77, I-78, I-79, I-80, I-81, I-84, I-85, I-86, I-89, I-90, I-92, I-96, I-97, I-104, I-108, I-125, I-136, I-137, I-138, II-2, II-3, II-5, II-6, II-7, II-8, II-9, II-10, II-11, II-12, II-15, II-16, II-17, II-23, II-24, II-25, II-26, II-27, II-28, II-33, II-34, II-35, II-36, II-37, II-38, II-39, II-43, II-44, II-50, II-52, II-53, II-54, II-55, II-58, II-60, II-63, II-64, II-65, II-66, II-68, II-69, II-70, II-71, II-73, II-74, II-75, II-76, II-78, II-79, II-83, II-84, II-85, II-86, II-87, II-88, II-89, II-90, II-91, II-92, II-93, II-97, II-98, II-99, II-101, II-102, II-105, II-107, II-111, II-116, II-117, II-118, II-121, II-130, II-131, II-132, II-133, II-134, II-136, II-137, II-138, II-140, II-141, II-142, II-151, II-153, II-154, II-159, II-160, III-1, III-2, III-3, III-4, III-5, III-6, III-15, III-16, III-17, III-18, III-19, III-20, III-21, IV-10, IV-11, IV-21, IV-23, IV-45, V-1, V-2, V-10, V-11, V-12, V-13, V-14, V-28, V-31, V-32, V-41, V-45, V-48, V-49, V-50, V-51, V-52, V-53, V-54, V-55, V-56, V-57, V-59, V-60, V-73, V-75, VII-1, VII-2, VII-3, VII-4, VII-5, VII-6, VII-7, VII-8, VII-9, VII-10, VII-11, VII-12, VII-13, VII-14, VII-15, VII-16, VII-17, VII-18, VII-19, VII-20, VII-21, VII-22, VII-23, VII-24, VII-25, VII-26, VII-27, VII-28, VII-29, VII-30, VII-31, VII-32, VII-33, VII-34, VII-35, VII-36, VII-37, VII-38, VII-39, VII-40, VII-41, VII-42, VII-43, VII-44, VII-45, VIII-12, VIII-32, VIII-42, VIII-47, VIII-49, VIII-55, VIII-57, VIII-58, VIII-61, VIII-64, VIII-65, VIII-67, VIII-85.
Test Example 4
Insecticidal Test for Diamond Back Moth (Plutella xylostella Linne)
The leaves of cabbage were dipped in a 500 ppm aqueous emulsion of a compound of the invention for about 10 seconds. After having been dried in air, the thus-treated leaves were put into laboratory dishes. Ten (10) second larvae of diamond back moth (Plutella xylostella) were released in each dish. Each dish was covered with a perforated cover, and stored in a thermostatic chamber at 25.degree. C. After 6 days passed, the insects in each dish were observed, and mortality of the insects was obtained according to the same equation as in Test Example 1. Each compound was tested in that manner for two groups of dishes. In this test, the following compounds exhibited mortality of 80% or more.
Compounds of the invention: Nos. I-1, I-2, I-4 I-5, I-6, I-8, I-9, I-10, I-13, I-18, I-19, I-29, I-30, I-31, I-33, I-34, I-35, I-36, I-38, I-39, I-40, I-41, I-43, I-44, I-45, I-46, I-47, I-51, I-52, I-53, I-56, I-57, I-58, I-59, I-62, I-63, I-70, I-71, I-72, I-73, I-74, I-76, I-77, I-78, I-79, I-80, I-81, I-84, I-86, I-89, I-96, I-97, I-99, I-104, I-106, I-114, I-125, I-137, II-1, II-2, II-5, II-6, II-7, II-8, II-9, II-10, II-11, II-12, II-13, II-15, II-17, II-23, II-24, II-25, II-26, II-27, II-28, II-33, II-34, II-35, II-36, II-37, II-38, II-39, II-40, II-41, II-42, II-43, II-54, II-55, II-58, II-60, II-61, II-62, II-63, II-64, II-65, II-66, II-67, II-68, II-69, II-70, II-71, II-72, II-73, II-74, II-75, II-76, II-77, II-78, II-79, II-80, II-81, II-83, II-84, II-85, II-86, II-87, II-88, II-89, II-90, II-91, II-92, II-93, II-94, II-97, II-98, II-99, II-100, II-101, II-105, II-106, II-107, II-108, II-109, II-110, II-111, II-116, II-117, II-118, II-121, II-122, II-155, II-159, II-161, III-1, III-2, III-3, III-4, III-5, III-6, III-7, III-9, III-10, III-11, III-13, III-14, III-15, III-16, III-17, III-18, III-19, III-20, III-21, IV-7, IV-8, IV-29, IV-47, IV-53, IV-58, V-1, V-2, V-11, V-12, V-13, V-29, V-37, V-41, V-43, V-46, V-48, V-50, V-51, V-52, V-53, V-54, V-55, V-56, V-57, V-58, V-59, V-60, V-64, V-75.
Test Example 5
Insecticidal Test for Cucurbit Leaf Beetles (Aulacophora femoralis Motschulsky)
A 5% emulsion (or 25% wettable powder) of a compound of the present invention was diluted with water containing a spreading agent to give a 500 ppm solution of the compound. The leaves of cucumbers were dipped in this chemical solution for about 10 seconds, dried in air, and put into a laboratory dish. Ten (10) second instar nymphae of cucurbit leaf beetles (Aulacophora femoralis) were released in each dish. Each dish was covered with a cover, and stored in a thermostatic chamber at 25.degree. C. After 6 days passed, the insects in each dish were observed, and mortality of the insects was determined according to the same equation as in Test Example 1. Each compound was tested in that manner for two groups of dishes.
In this test, the following compounds exhibited mortality of 100%.
Compounds of the invention: Nos. I-1, I-2, I-4, I-6, I-8, I-9, I-10, I-11, I-12, I-13, I-29, I-30, I-31, I-32, I-33, I-34, I-35, I-39, I-40, I-41, I-43, I-44, I-46, I-53, I-54, I-55, I-56, I-57, I-58, I-59, I-61, I-62, I-63, I-69, I-70, I-71, I-72, I-74, I-76, I-77, I-78, I-79, I-80, I-81, I-82, I-83, I-92, I-101, I-103, I-104, I-108, I-109, I-124, I-127, I-128, II-1, II-6, II-7, II-8, II-9, II-10, II-11, II-12, II-13, II-14, II-15, II-16, II-17, II-23, II-24, II-25, II-26, II-27, II-28, II-33, II-34, II-35, II-36, II-37, II-38, II-39, II-41, II-42, II-43, II-47, II-50, II-53, II-54, II-55, II-57, II-58, II-61, II-62, II-63, II-65, II-66, II-99, II-101, II-102, II-104, II-105, II-106, II-107, II-108, II-109, II-110, II-114, II-122, II-124, II-125, II-131, II-132, II-133, II-134, II-136, II-137, II-139, II-140, II-141, II-142, II-153, II-154, III-1, III-2, III-3, III-4, III-5, III-6, III-9, III-10, III-11, III-12, III-14, III-15, III-16, III-17, III-20, IV-6, IV-13, IV-33, IV-39, IV-56, IV-60, IV-61, IV-72, IV-82, V-1, V-2, V-11, V-12, V-13, V-17, V-22, V-26, V-27, V-29, V-37, V-40, V-42, V-48, V-49, V-50, V-51, V-52, V-54, V-55, V-57, V-59, V-60, V-61, V-64, V-75.
Test Example 6
Acaricidal Test for Two-spotted Spider Mites (Tetranychus urticae Koch)
The leaves of kidney bean plants were punched into 3 cm-diameter discs, using a leaf punch, and put onto moistured filter paper in a 7 cm-diameter styrol cup. Ten (10) larvae of two-spotted spider mites (Tetranychus urticae) were put to each leaf. A 5% emulsion (or 25% wettable powder) of a compound of the invention was diluted with water containing a spreading agent to give a 500 ppm solution of the compound. The solution was sprayed over each cup in an amount of 2 ml/cup, using a rotary sprinkler, and the cups were stored in a thermostatic chamber at 25 .degree. C. After 96 hours passed, the mites in each cup were observed, and mortality of the mites was determined according to the same equation as in Test Example 1. Each compound was tested in that manner for two groups of cups.
In this test, the following compounds exhibited the mites at a percentage of 80% or more.
Compounds of the invention: Nos. I-1, I-2, I-3, I-4, I-5, I-7, I-8, I-9, I-10, I-12, I-13, I-19, I-24, I-25, I-26, I-27, I-28, I-29, I-30, I-31, I-32, I-33, I-34, I-35, I-36, I-38, I-40, I-41, I-42, I-43, I-44, I-45, I-46, I-47, I-48, I-50, I-51, I-52, I-55, I-56, I-57, I-58, I-59, I-60, I-61, I-62, I-63, I-70, I-71, I-72, I-74, I-76, I-80, I-94, I-95, I-96, I-97, I-99, I-101, I-102, I-103, I-104, I-105, I-106, I-108, I-109, I-110, I-111, I-112, I-113, I-114, I-115, I-117, I-118, I-119, I-122, I-123, I-124, I-125, I-126, I-127, I-128, I-137, II-2, II-3, II-5, II-6, II-7, II-8, II-9, II-10, II-11, II-12, II-13, II-15, II-16, II-17, II-23, II-25, II-26, II-27, II-28, II-33, II-34, II-35, II-36, II-37, II-38, II-39, II-40, II-41, II-42, II-43, II-45, II-46, II-47, II-48, II-50, II-52, II-53, II-54, II-55, II-58, II-59, II-60, II-61, II-63, II-64, II-65, II-66, II-67, II-68, II-69, II-70, II-71, II-72, II-73, II-74, II-75, II-76, II-77, II-78, II-79, II-80, II-81, II-83, II-84, II-85, II-86, II-87, II-88, II-89, II-90, II-91, II-92, II-93, II-95, II-97, II-98, II-99, II-101, II-102, II-103, II-105, II-106, II-107, II-108, II-109, II-110, II-111, II-116, II-117, II-118, II-133, II-134, II-136, II-137, II-151, II-153, II-154, II-155, II-159, II-160, II-161, II-173, III-3, III-4, III-5, III-6, III-7, III-9, III-10, III-11, III-12, III-15, III-17, III-18, III-19, III-21, IV-1, IV-2, IV-3, IV-4, IV-5, IV-7, IV-10, IV-11, IV-12, IV-13, IV-14, IV-16, IV-17, IV-18, IV-19, IV-20, IV-21, IV-22, IV-24, IV-25, IV-26, IV-28, IV-29, IV-33, IV-35, IV-36, IV-39, IV-40, IV-41, IV-42, IV-43, IV-44, IV-45, IV-46, IV-47, IV-48, IV-49, IV-50, IV-51, IV-54, IV-55, IV-56, IV-58, IV-59, IV-60, IV-61, IV-62, IV-63, IV-64, IV-65, IV-66, IV-67, IV-68, IV-69, IV-70, IV-71, IV-72, IV-74, IV-75, IV-76, IV-79, IV-80, IV-82, IV-94, IV-95, IV-96, IV-99, IV-100, IV-101, IV-102, IV-109, IV-110, IV-111, IV-112, V-1, V-2, V-3, V-4, V-5, V-6, V-7, V-8, V-10, V-11, V-12, V-13, V-14, V-15, V-16, V-17, V-19, V-23, V-24, V-25, V-26, V-28, V-31, V-36, V-37, V-38, V-40, V-41, V-42, V-43, V-44, V-46, V-47, V-48, V-49, V-50, V-51, V-52, V-53, V-54, V-55, V-56, V-57, V-58, V-59, V-60, V-73, V-75, VI-1, VI-2, VI-3, VI-4, VI-5, VI-6, VI-7, VI-8, VI-9, VI-10, VI-11, VI-12, VI-13, VI-14, VI-15, VI-16, VI-17, VI-18, VI-19, VI-20, VI-21, VI-22, VI-23, VI-24, VI-25, VI-29, VI-30, VI-31, VI-32, VI-33, VI-34, VI-35, VI-36, VI-37, VI-38, VI-39, VI-40, VI-41, VI-42, VI-43, VI-44, VI-45, VI-46, VI-47, VI-48, VI-49, VI-50, VI-51, VI-52, VIII-1, VIII-2, VIII-4, VIII-6, VIII-7, VIII-8, VIII-9, VIII-10, VIII-13, VIII-14, VIII-15, VIII-16, VIII-17, VIII-18, VIII-19, VIII-20, VIII-21, VIII-22, VIII-23, VIII-24, VIII-26, VIII-27, VIII-28, VIII-29, VIII-30, VIII-31, VIII-33, VIII-34, VIII-35, VIII-36, VIII-37, VIII-38, VIII-39, VIII-40, VIII-41, VIII-43, VIII-44, VIII-45, VIII-46, VIII-48, VIII-50, VIII-51, VIII-52, VIII-53, VIII-54, VIII-56, VIII-59, VIII-60, VIII-63, VIII-66, VIII-69, VIII-70, VIII-71, VIII-72, VIII-73, VIII-74, VIII-75, VIII-76, VIII-77, VIII-78, VIII-81, VIII-82, VIII-83, VIII-84, VIII-86, VIII-87, VIII-89, VIII-90, VIII-91, VIII-92, VIII-93.
Test Example 7
Test for Preventing Leaf Rust, Brown Rust (Puccinia recondita ex Desmaziere)
A chemical solution obtained by diluting an emulsion of a compound of the invention to 500 ppm with water was sprayed on wheat plants (Norin No. 61) grown to 1.5- to 2.0-leaf in a pot having a diameter of 5.5 cm-diameter at a dose of 20 ml/pot using a spraygun.
The following day, a spore suspension (2.times.10.sup.5 spore/ml) of leaf rust (brown rust) (Puccinia recondite) was sprayed over the plant-pots were placed overnight in an inoculation box having a temperature of 25.degree. C. and a humidity of 95% or more. Then, the pots were put in a green house. After 7 days of the inoculation, a ratio of an infected and spored area formed to the leaf inoculated was measured, and a preventive value was calculated according to the following equation.
Preventive value=[1-(infected and spotted area ratio in treated region/infected and spotted area ratio in untreated region)].times.100
In this test, the following compounds had an protective value of from 70 to 100.
Compounds of the invention: Nos. I-9, I-108, I-127, I-128, II-14, II-15, IV-2, IV-7, V-15, V-10.
With the long-term use of insecticides and microbicides, recently, some pests have become resistant to chemicals and are often difficult to exterminate with conventional insecticides and microbicides. In addition, some insecticides are highly toxic and are prone to remain long, without being decomposed, to destroy the ecosystem. Accordingly, the present invention provides novel, non-toxic and non-persistent insecticides and fungicides, and provides agents for preventing the attachment of aquatic organisms having few influences on the ecosystem and causing little secondary pollution.

Number	Date	Country
8-104878	Apr 1996	JPX
8-145802	Jun 1996	JPX
8-159346	Jun 1996	JPX
9-28916	Feb 1997	JPX

Number	Name	Date
3337565	Bencze et al.	Aug 1967
3337566	Walker et al.	Aug 1967
4600712	Haken et al.	Jul 1986

Number	Date	Country
0 706 758	Apr 1996	EPX
52-105167	Sep 1977	JPX
53-92769	Aug 1978	JPX
A-57-502215	Dec 1982	JPX
A-59-219228	Dec 1984	JPX
A-60-11452	Jan 1985	JPX
A-60-11401	Jan 1985	JPX
A-60-209571	Oct 1985	JPX
WO 9529591	Nov 1995	WOX
WO 9842683	Oct 1998	WOX

Etylene derivatives and pesticides containing said derivatives

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Entry
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