USE OF MALONIC ACID DERIVATIVE COMPOUNDS FOR RETARDING PLANT GROWTH

Abstract: Method for retarding plant growth by applying to the plant an effective amount of a malonic acid derivative compound. This invention also relates to novel malonic acid derivative compounds and processes for the preparation thereof.

Description: Use of Malonic Acid Derivative Compounds for Retarding Plant Growth Brief Summary of the Invention Technical Field This invention relates to the use of malonic acid derivative compounds for retarding plant growth. This invention further relates to novel malonic acid derivative compounds and processes for the preparation thereof. Background of the Invention Certain malonic acid derivative compounds have been known for some time in the art. See, for example, U.S. Patent 2,504,896 and U.S. Patent 3,254,108 Some malonic acid derivative compounds have been described in the art as capable of providing certain plant growth regulating responses such as prevention of fruit drop, rooting of cuttings and formation of parthenogenetic fruit. U.S. Patent 3,072,473 describes Narylmalonamic acids and their esters and salts, N, N '-diarylmalonamides, N-alkyl-N-arylmalonamic acids and their esters and salts, and N, N'-dialkyl-N, N'-diarylmalonamides which may be useful as plant growth regulants and herbicides. Japanese Patent 84 39,803 (1984) describes malonic acid anilide derivative compounds which may be useful as plant growth regulators. The plant growth regulating properties of substituted malonyl monoanilides are described by Shindo, N. and Kato, M., Meiji Daigaku Noogaku-bu Kenkyu Hokoku, Vol. 63, pp. 41-58 (1984). However, certain malonic acid derivative compounds and the use of malonic acid derivative compounds for retarding plant growth as described herein have not been disclosed in the art. Accordingly, it is an object of this invention to provide a method for the use of malonic acid derivative compounds to retard plant growth. It is another object of this invention to provide novel malonic acid derivative compounds and processes for the preparation thereof. These and other objects will readily become apparent to those skilled in the art in light of the teachings herein set forth. Disclosure of the Invention This invention relates to a method for retarding plant growth which comprises applying to the plant an effective amount, sufficient to retard plant growth, of a compound having the formula: EMI2.1 wherein R1, R2 Y1' Y2, 3 V4, 4 and V6 are as defined hereinafter. This invention also relates to novel malonic acid derivative compounds and to processes for the prepartion of said compounds. Detailed Descrintion As indicated above, this invention relates to a method of retarding plant growth by use of certain malonic acid derivative compounds. More particularly, this invention involves a method for retarding plant growth which comprises applying to the plant an effective amount, sufficient to retard plant growth, of a compound having the formula: EMI3.1 wherein: : R1 and R2 are independently a substituted or unsubstituted, carbocyclic or heterocyclic ring system selected from a monocyclic aromatic or nonaromatic ring system, a bicyclic aromatic or nonaromatic ring system, a polycyclic aromatic or nonaromatic ring system, and a bridged ring system which may be saturated or unsaturated in which the permissible substituents (Z) are the same or different and are one or more hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, formyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhal oalkenylthio, thiocyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsi lyloxy, aryldialkylsilyloxy, triarylsilyloxy, formamidino, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino, azido, azo, aminocarbonyl, alkylaminocarbonyl, hydrazino, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, nitro, cyano, hydroxycarbonyl and derivative salts, formamido, alkyl, alkoxy, polyhaloalkyl, polyhaloalkoxy, alkoxycarbonyl, substituted amino in which the permissible substituents are the same or different and are one or two propargyl, alkoxyalkyl, alkylthioalkyl, alkyl, alkenyl, haloalkenyl or polyhaloalkenyl; alkylthio, polyhaloalkylthio, alkylsulfinyl, polyhaloalkylsulfinyl, alkylsulfonyl, polyhaloalkylsulfonyl, alkylsulfonylamino, alkylcarbonylamino, polyhaloalkylsulfonylamino, polyhaloalkylcarbonylamino, trialkylsilyl, aryidialkylsilyl, triarylsilyl, sulfonic acid and derivative salts, phosphonic acid and derivative salts, alkoxycarbonylamino, alkylaminocarbonyloxy, dialkylaminocarbonyloxy, alkenyl, polyhaloalkenyl, alkenyloxy, alkynyl, alkynyloxy, polyhaloalkenyloxy, polyhaloalkynyl, polyhaloalkynyloxy, polyfluoroalkanol, cyanoalkylamino, semicarbazonomethyl, alkoxycarbonylhydrazonomethyl, alkoxyiminomethyl, unsubstituted or substituted aryloxyiminomethyl, hydrazonomethyl, unsubstituted or substituted arylhydrazonomethyl, a hydroxy group condensed with a mono-, di- or polysaccharide, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, aryloxy, aralkoxy, arylthio, aralkylthio, alkylthioalkyl, arylthioalkyl, arylsulfinyl, arylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, haloalkenyloxy, haloalkynyloxy, haloalkynylthio, haloalkenylsulfonyl, polyhaloalkenylsulfonyl, isocyano, aryloxysulfonyl, propargyloxy, aroyl, haloacyl, polyhaloacyl, aryloxycarbonyl, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, arylaminosulfonyl, carboxyalkoxy, carboxyalkylthio, alkoxycarbonylalkoxy, acyloxy, haloacyloxy, polyhaloacyloxy, aroyloxy, alkylsulfonyloxy, alkenylsulfonyloxy, arylsulfonyloxy, haloalkylsulfonyloxy, polyhaloalkylsulfonyloxy, aroylamino, haloacylamino, alkoxycarbonyloxy, arylsulfonylamino, aminocarbonyloxy, cyanato, isocyanato, isothiocyano, cycloalkylamino, trialkylammonium, arylamino, aryl(alkyl)amino, aralkylamino, alkoxyalkylphosphinyl, alkoxyalkylphosphinothioyl, alkylhydroxyphosphinyl, dialkoxyphosphino, hydroxyamino, al koxyami no, aryloxyamino, aryloxyimino, oxo, thiono, diazo, alkylidene, alkylimino, hydrazono, semicarbazono,dialkylsulfonium, dialkylsulfuranylidene, dialkyloxosulfuranylidene, -X, = x, -X = R3, = X-R3, EMI5.1 R1 and R2 are independently hydrogen or derivative salts, or a substituted heteroatom or substituted carbon atom, or a substituted or unsubstituted, branched or a straight chain containing two or more carbon atoms or heteroatoms in any combination in which the permissible substituents are Z as hereinbefore defined; V1 and V2 are independently a substituted or unsubstituted heteroatom in which the permissible substituents are Z as hereinbefore defined; ; V3 and Y4 are independently hydrogen, or a substituted or unsubstituted heteroatom or substituted carbon atom, or a substituted or unsubstituted, branched or straight chain containing two or more carbon atoms or heteroatoms in any combination, or halogen, alkylcarbonyl, formyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiocyano, propargylthio, trialkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxy, formamidino, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino, hydrazino, azo, aminocarbonyl, alkylaminocarbonyl, azido, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, nitro, cyano, hydroxycarbonyl and derivative salts, formamido, alkyl, alkoxy, polyhaloalkyl, polyhaloalkoxy, alkoxycarbonyl, substituted amino in which the permissible substituents are the same or different and are one or two propargyl, alkoxyalkyl, alkylthioalkyl, alkyl, alkenyl, haloalkenyl or polyhaloalkenyl; alkylthio, polyhaloalkylthio, alkylsulfinyl, polyhaloalkylsulfinyl, alkylsulfonyl, polyhaloalkylsulfonyl, alkylsulfonylamino, alkylcarbonylamino, polyhaloalkyl sul fonylami no, polyhaloalkylcarbonylamino, trialkylsilyl, aryldialkylsilyl, triarylsilyl, sulfonic acid and derivative salts, phosphonic acid and derivative salts, alkoxycarbonylamino, alkylaminocarbonyloxy, dialkylaminocarbonyloxy, alkenyl, polyhaloalkenyl, alkenyloxy, alkynyl, alkynyloxy, polyhaloalkenyloxy, polyhaloalkynyl, polyhaloalkynyloxy, polyfluoroalkanol, cyanoalkylamino, semicarbazonomethyl, alkoxycarbonylhydrazonomethyl, alkoxyiminomethyl, unsubstituted or substituted aryloxyiminomethyl, hydrazonomethyl, unsubstituted or substituted arylhydrazonomethyl, a hydroxy group condensed with a mono-, di- or polysaccharide, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, aryloxy, aralkoxy, arylthio, aralkylthio, alkylthioalkyl, arylthioalkyl, arylsulfinyl, arylsulfonyl, haloalkylsulfinyl, hdloalkylsulfonyl, haloalkenyloxy, haloalkynyloxy, haloalkynyl thio, haloalkenylsulfonyl, polyhaloalkenylsulfonyl, isocyano, aryloxysulfonyl, propargyloxy, aroyl, haloacyl, polyhaloacyl, aryloxycarbonyl, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, arylaminosulfonyl, carboxyalkoxy, carboxyalkylthio, alkoxycarbonylalkoxy, acyloxy, haloacyloxy, polyhaloacyloxy, aroyloxy, alkylsulfonyloxy, alkenylsulfonyloxy, arylsulfonyloxy, haloalkylsulfonyloxy, polyhaloalkyl sulfonyloxy, aroylamino, haloacylamino, alkoxycarbonyloxy, arylsulfonylÅamino, aminocarbonyloxy, cyanato, tsocyanato, isothiocyano, cycloalkylamino, trialkylammonium, arylamino, aryl (alkyl )amino, aralkylamino, alkoxyalkylphosphinyl, alkoxyalkylphosphinothioy, alkylhydroxyphosphinyl, dialkoxyphosphino, hydroxyamino, alkoxyamino, aryloxyamino, -X, -X = R3, --X - R3 EMI7.1 or EMI8.1 in which the permissible substituents are Z as hereinbefore defined; or V3 and Y4 taken together are oxo, thiono, diazo, = X or = X - R3, or substituted or unsubstituted alkylidene, alkylimino, hydrazono, dialkylsulfuranyl idene, dialkyloxosulfuranylidene semicarbazono, hydroxyimino, alkoxyimino or aryloxyimino in which the permissible substituents are Z as hereinbefore defined; Y3 and Y4 may be linked together to form a substituted or unsubstituted, carbocyclic or heterocyclic ring system selected from a monocyclic aromatic or nonaromatic ring system, a bicyclic aromatic or nonaromatic ring system, a polycyclic aromatic or nonaromatic ring system, and a bridged ring system which may be saturated or unsaturated in which the permissible substituents are Z as hereinbefore defined; and V5 and Y6 are independently oxygen or sulfur; wherein: X is a covalent single bond or-double bond, a substituted or unsubstituted heteroatom or substituted carbon atom, or a substituted or unsubstituted, branched or straight chain containing two or more carbon atoms or heteroatoms in any combination in which the permissible substituents are Z as hereinbefore defined; R3 is a substituted or unsubstituted, carbocyclic or heterocyclic- ring system selected from a monocyclic aromatic or nonaromatic ring system, a bicyclic aromatic or nonaromatic ring system, a polycyclic aromatic or nonaromatic ring system, and a bridged ring system which may be saturated or unsaturated in which the permissible substituents are Z as hereinbefore defined; or R3 is a substituted heteroatom or substituted carbon atom, or a substituted or unsubstituted, branched or straight chain containing two or more carbon atoms or heteroatoms in any combination in which the permissible substituents are Z as hereinbefore defined; EMI9.1 The alkyl-containing moieties in formula 1 may contain from about 1 to about 100 carbon atoms or greater, preferably from about 1 to about 30 carbon atoms, and more preferably from about 1 to about 20 carbon atoms. The polysaccharide moiety may contain up to about 50 carbon atoms. It is appreciated that all compounds encompassed within formula 1 are compounds having no unfilled bonding positions. In regard two the malonic acid derivative compounds used in this invention, it is preferred that R1 and R2 are independently other than hydrogen, alkyl or aryl when both Y1 and Y2 are -NH-. As used herein, hydrogen or derivative salts refer to hydrogen or any appropriate derivative salt substituents which may be substituted therefor. Illustrative derivative salt substituents include, for example, ammonium, alkylammonium, polyalkylammonium, hydroxyalkylammonium, poly(hydroxyalkyl )ammonium, alkali metals, alkaline earth metals and the like including mixtures thereof. Monocyclic ring systems encompassed by R1, R2 and R3 in formula 1 may be represented by generalized formula 2 as follows: EMI10.1 wherein B1 represents a saturated or unsaturated carbon atom and A1 represents a ring-forming chain of atoms which together with B1 forms a cyclic system containing from 0 to 3 double bonds or from 0 to 2 triple bonds. A1 may contain entirely from 2 to 12 carbon atoms, may contain a combination of from 1 to 11 carbon atoms and from 1 to 4 heteroatoms which may be selected independently from N, 0, S, P or other heteroatoms, or may contain 4 ring-forming heteroatoms alone. Monocyclic ring systems encompassed by Y3 and Y4 linked together in formula 1 may include any monocyclic ring system of R1, R2 and R3 appropriately positioned in formula 1. Ring-forming heteroatoms may in some cases bear oxygen atoms as in aromatic N-oxides and ring systems containing the sulfinyl, sulfonyl, selenoxide and phosphine oxide moieties. Selected carbon atoms contained in cycles formed by B1 and A1 containing at least 3 ring-forming atoms may bear carbonyl, thiocarbonyl, substituted or unsubstituted imino groups or substituted or unsubstituted methylidene groups. The group designated as Z represents one or more substituents selected independently from among the group of substituents defined for Z herein. Bicyclic ring systems encompassed by R1, R2 and R3 in formula 1 may be represented by generalized formulae 3 and 4 as follows: EMI11.1 wherein B2 and 83 may be independently a saturated or unsaturated carbon atom or a saturated nitrogen atom, A2 and A3 independently represent the ring-forming chains of atoms described below and Z represents one or more substituents selected independently from among the group of substituents defined for Z herein. Combinations of A2 and A3 may contain in combination with 82 or B3 from 0 to 5 double bonds. A2 and A3, independent of 82 and B3, may contain entirely from 1 to 11 carbon atoms, may contain a combination of 1 to 3 heteroatoms which may be selected independently from among N, 0, S, P or other heteroatoms together with from 1 to 10 carbon atoms or may contain from 1-3 ring-forming heteroatoms alone. Ring-forming heteroatoms may in some cases bear oxygen atoms, as in aromatic N-oxides and ring systems containing the sulfinyl, sulfdnyl, selenoxide and phosphine oxide groups. Selected carbon atoms contained in A2 and A3 may bear carbonyl, thiocarbonyl, substituted or unsubstituted imino groups or substituted or unsubstituted methylidene groups. Bicyclic ring systems encompassed by Y3 and Y4 linked together in formula 1 may include any bicyclic ring system of R1, R2 and R3 appropriately positioned in formula 1. In regard to structures encompassed within formulae 3 and 4 it is noted as follows: (a) When 82 and B3 are both nitrogen, the groups A2 and A3 should each contain no fewer than three ring atoms; (b) When B2 but not 83 is nitrogen, either of A2 or A3 should contain at least three ring atoms and the other at least two. ring atoms; (c) When either of groups A2 or A3 contains fewer than three ring atoms, the other should contain at least three ring atoms and the br;dgehead atoms should be saturated; (d) When the group A2 or A3 contains a carbon atom bearing a carbonyl, thiocarbonyl, imino or methylidene group, it should together with 82 and B3 form a cycle having at least four members; ; (e) When a annular double bond is exocyclic to either of the two rings represented in structures 3 and 4, it should be contained in a ring containing at least five members and be exocyclic to a ring containing at least five members; and (f) When a group A2 or A3 is joined to the bridgehead atoms 82 and 83 by 2 double bonds, the group A2 or A3 is understood to contain one double bond and the bridgehead atoms are considered to be unsaturated. It is recognized that bicyclic ring systems defined for R1, R2, R3 and V3 and V4 linked together may be spirocyclic ring systems and are not limited to the fused bicyclic structures of formulae 3 and 4. Spirocyclic ring systems may be saturated or unsaturated carbocyclic or heterocyclic and may be independently substituted by one or more substituents Z as defined herein. Polycyclic ring systems, i.e., greater than 2 rings, encompassed by R1, R2 and R3 in formula 1 may be represented by generalized formulae 5 6 7 and 8 as follows: EMI14.1 wherein B4, 85, B6 and B7 may be independently a saturated or unsaturated carbon atom or a saturated nitrogen atom, and A4, A5, A6 and A7 independently represent ring forming chains of atoms which may contain together with one or the other (but not both) of their two associated bridgehead atoms, from 0-2 double bonds. The groups Z represent one or more substituents selected independently from among the group of substituents defined for Z herein. The ring-forming elements of A4, A5, A6 and A7 independent of B4, B5, B6 and B7 may contain from 1-11 carbon atoms, may co-ntain a combination of from 1-10 carbon atoms and from 1-3 heteroatoms which may be selected independently from among N, 0, S, P or other heteroatoms, or may contain from 1-3 heteroatoms alone. Ring-forming heteroatoms may in some cases bear oxygen atoms as in aromatic N-oxides and ring systems containing the sulfinyl, sulfonyl, selenoxide and phosphine oxide groups. The group A6 may at times be defined as a bond. Selected carbon atoms contained in A4, A5, A6 and A7 may bear one or more carbonyl, thiocarbonyl or substituted or unsubstituted imino groups. On structure 8 the groups B8, B9 and 810 represent independently a saturated or unsaturated carbon atom or a saturated nitrogen atom. The group B11 may represent a saturated or unsaturated carbon atom or a nitrogen or phosphorous atom. The groups A8, Ag and A10 represent ring-forming chains of atoms which may contain together with 1 of the groups B8, B9, B10 and B11 from 0-2 double bonds. The ring-forming elements of groups A8, A9 and A10 independent of groups B8, Bg' 810 and B11 may contain from 2-10 carbon atoms, may contain from 1-10 carbon atoms in combination with 1-3 heteroatoms which may be selected independently from among N, O, S, P or other heteroatoms, or may contain from 2-3 heteroatoms alone. Ring-forming heteroatoms may in some cases bear oxygen atoms as in aromatic N-oxides and in ring systems containing the sulfinyl, sulfonyl, selenoxide and phosphine oxide groups. Selected carbon atoms contained in groups A8, Ag and A10 may bear one or more carbonyl, thiocarbonyl or substituted or unsubstituted imino groups. It is recognized that polycyclic ring systems defined for R1, R2, R3 and V3 and Y4 linked together may be spirocyclic ring systems and are not limited to the f@@ed polycyclic structures of formulae 5, 6, 7 and 8. Spirocyclic ring systems may be saturated or unsaturated, carbocyclic or heterocyclic and may be independently substituted by one or more substituents Z as defined herein. Polycyclic ring systems encompassed by Y3 and Y4 linked together in formula 1 may include any polycyclic ring system of R1, R2 and R3 appropriately positioned in formula 1. Bridged bicyclic structures encompassed by R1, R2 and R3 in formula 1 may be represented by generalized formulae 9, 10, and 11 as follows: EMI17.1 wherein 812 and B13 may be independently a saturated carbon atom optionally substituted by Z or a nitrogen atom, and the groups All, A12 and A13 independently represent ring-forming chains of atoms which may contain, independently of B12 and B13, from 0-2 double bonds. The groups Z represent one or more substituents selected independently from among the groups of substituents defined for Z herein. The ring-forming elements of All, A12 and A13, independent of B12 and B13, may contain entirely from 1-11 carbon atoms, may contain a combination of from 1-10 carbon atoms and from 1-3 heteroatoms which may be selected independently from among N, O, S, P or other heteroatoms, or may contain from 1-3 heteroatoms alone with the proviso that when one of the groups All, A12 and A13 is a single heteroatom, the other two groups should contain two or more ring-forming atoms. A second proviso is that when one or both of the groups B12 and B13 is nitrogen, the groups All, A12 and A13 should contain at least two saturated ring-forming atoms. Ring-forming heteroatoms may in some cases bear oxygen atoms as in the sulfinyl, sulfonyl, selenoxide and phosphine oxide moieties. Selected carbon atoms contained in All, A12 and A13 may bear one or more carbonyl, thiocarbonyl or substituted or unsubstituted imino groups. Bridged bicyclic structures encompassed by V3 and Y4 linked together in formula 1 may include any bicyclic bridged system of R1, R2 and R3 appropriately positioned in formula 1. It is readily apparent that formula 1 encompasses a wide variety of malonic acid derivative compounds. Illustrative malonic acid derivative compounds within the scope of formula 1 which may be used for retarding plant growth are included in Tables 1 through 11 below. AbIL I Representative Malonic Acid Derlvative Compounds EMI19.1 Z'8 R'7 3-F-5-Cl OC2H5 3-F-5-Cl OCH3 3-F-5-Cl OH 3-F-5-Br OC2H5 3-F-5-Br ONa 3-CF3-5-Cl OCH3 3-CF3-5-Cl ONH4 3-CF3-5-Br OC2H5 3-CF3-5-Br NH2 3-CF3-5-Br OH 3-F-4-Cl OC2H5 3-F-4-Cl OCH3 3-F-4-Cl OK 3-F-4-Br OH 3-F-4-Br OCH3 3-F-4-Br O-n.C3H7 2-F-4,5-Cl2 OH 2-F-4,5-Cl2 OC2H5 2-F-4-Cl-5-Br OH 2-F-4-Cl-5-Br OCH3 TABLE 1 (Cont.) Representative Malonic Acid Derivative Compounds EMI20.1 Z'8 R'7 2-F-4-Br-5-Cl OH 2-F-4-Br-5-Cl OC2H5 2-F-4,5-Br2 OH 2-F-4,5-Br2 OCH3 2-F-4,5-Br2 ONH4 2,4-Cl2-5-F OH 2,4-Cl2-5-F OC2H5 2-Cl-4-Br-5-F OCH3 2-Cl-4-Br-5-F O-n-C3H7 2,4-Br2-5-F OH 2,4-Br2-5-F OCH3 2-Br-4-Cl-5-F OH 2-Br-4-Cl-5-F OC2H5 2-CH3-4-Cl-5-F OH 2-CH3-4-Cl-5-F OC2H5 2-CH3-4-Cl-5-F OH 2-CH3-4-Cl-5-F OC2H5 2-CH3-4-Cl-5-F ONa 2-CH3-4-Br-5-F OH 2-CH3-4-Br-5-F O-n-C4H9 2-CH3-4-Br-5-F OK ABTE 1 (Cont.) Representative Malonic Acid DerIvatIve Compounds EMI21.1 Z'8 R'7 2-Cl-4-CF3O OCH3 2-CF3O-4-Br OC2H5 2-CH3-4-CF3CF2O- O-n-C3H7 2-CH3-4-1 OCH3 2-F-4-1 OC2H5 2-CH3O-3,5-Br2 ONa 3-BR-4-Cl OC2H@ 2,4-Cl2 NHCH3 TABLE 2 Representative Malonic Acid Derivative Compounds EMI22.1 EMI22.2 <tb> <SEP> 6 <SEP> t <SEP> 9 <tb> OCH2CH2OH <SEP> 2-CH3-4-Sr <tb> OCH2CH20H <SEP> 2F-4-Sr <tb> OCH2CH20H <SEP> 3,4-Cl2 <tb> OCH(CH3)CO2C2H5 <SEP> 2-CH3-4-8r <tb> OCH(CH3)CO2C2H5 <SEP> 4 <SEP> Cl <tb> OCH2CH2N(CH3)2 <SEP> 2.4-Sr2 <tb> SCH3 <SEP> 2,4,5-Cl3 <tb> S-C <SEP> H <tb> S-C6H5 <SEP> 3,5-8r2 <tb> S-C3H7 <SEP> 2.4-Cl2 <tb> OCH2COzC2H5 <SEP> 3-f-5-Br <tb> SCH2CO <SEP> C <SEP> H <SEP> 2-CH3-4-Sr <tb> SCH2C02C2H5 <SEP> 2-CH3-4-8r-S-CI <tb> OCH2CH2SCH3 <SEP> 2-f-A-Sr <tb> OCH <SEP> SO <SEP> Cli <SEP> 3,5-Cl <tb> OCH2CH2SO2CH3 <SEP> 3,5-Sr2 <tb> OCH2CCH3 <SEP> 3-8r-S-Cl <tb> <SEP> o <tb> TABLE 2 (Cont.) Representative Malonic Acid Dertvative Compounds EMI23.1 EMI23.2 <tb> <SEP> 8 <SEP> 9 <tb> OCH <SEP> CCH <SEP> 2, <SEP> 4 <SEP> - <SEP> C <SEP> 12 <tb> <SEP> o <tb> OCH(CH3)CN <SEP> 2CH3-4-Sr <tb> OCH(CH3)CN <SEP> 4-Br <tb> O-N.CHCH3 <SEP> 4 <SEP> Cl <tb> O-N.C(CH3)2 <SEP> 3,1-C12 <tb> O <SEP> 11 <SEP> CH3 <SEP> 2,4-Cl2 <tb> <SEP> SCH3 <tb> <SEP> / <SEP> CH3 <SEP> 2-CH3-4Cl <tb> O-N.C <SEP> 2-CH3-4-Cl <tb> OCH2CH2wHCO2CH3 <SEP> 2-Cli <SEP> -4.Sr <tb> <SEP> 22 <SEP> 23 <SEP> 3 <tb> OCH2CH20- <SEP> C- <SEP> HHC2H5 <SEP> 4 <SEP> 4.CI <tb> <SEP> o <tb> <SEP> / <SEP> OC2H5 <SEP> 2.F-4C?3 <tb> OCH2P <SEP> 2- <SEP> F <SEP> - <SEP> 4 <SEP> CF <SEP> 3 <tb> <SEP> OCZH <tb> <SEP> OCH1 <tb> OCH2CH2P <SEP> OCH <SEP> 2,J-C12 <tb> <SEP> OtHj <tb> <SEP> / <SEP> OCH3 <tb> SUCH2: <SEP> OCH3 <SEP> 3,4 <SEP> Cl2 <tb> <SEP> '\ <SEP> 0cnj <tb> OCH2COH2 <SEP> 3,5 <SEP> (Cf3)2 <tb> TABLE 2 (Cont.) Representative Malonic Acid Derivative Compounds EMI24.1 EMI24.2 <tb> <SEP> R'g <SEP> Z'9 <tb> <SEP> OC2H5 <tb> / <SEP> 2 <SEP> OCPS <tb> SCH2CH2P <SEP> \ <SEP> 3-8r-S-CI <tb> <SEP> 0 <tb> <SEP> o <tb> <SEP> / <SEP> OC6H5 <SEP> 3- <SEP> Cl-S-Cf3 <tb> SCli2CH2P <SEP> \ <SEP> 3-Cl-S-Cf3 <tb> <SEP> OCgH5 <tb> <SEP> 0 <tb> OCH2CH2SCH2CH20H <SEP> 3-8r-S-Cf3 <tb> OCH2CH2502CH2CH20H <SEP> 3-F-4-8r <tb> <SEP> 22222 <tb> OCH2C.H <SEP> 4-1 <tb> OCH2CH2C.N <SEP> 2,4-Cl2 <tb> O.C(CH3)2CN <SEP> 4 <SEP> Cl <tb> OCH2CH2OCli3 <SEP> 3-F-S-Cl <tb> OCH2C02C2H5 <SEP> 3-f-4-Cl <tb> OCH2CH2 <SEP> 2-F-4,S.Cl2 <tb> OCH(CH3)CH2SC2H5 <SEP> 2-f-A-Cl-S-Br <tb> OCH2COCH3 <SEP> 2-F-4-Br-S-CI <tb> OCH2C.N <SEP> 2-F-4.5-8r2 <tb> O-NC(CH3)-CO <SEP> C <SEP> H <SEP> 2,4-Cl2-5-F <tb> O-tHtSOZtlHZ <SEP> 2-C1-)-8r-5-F <tb> <SEP> 222 <tb> O-CH2SO2NHCH3 <SEP> 2,4-8r2-S-F <tb> -CH25 2H(c2HS)2 <SEP> 2 <SEP> 8r-4 <SEP> Cl-S-F <tb> S-CH2CH2SCH3 <SEP> 2 <SEP> CH3 <SEP> 4-CI-5-f <tb> S-CH2C02C3H1 <SEP> 2 <SEP> CH3 <SEP> 4-Br-S-F <tb> TABLE 2 (Cont.) Representative Malonic Acid Derivative Compounds EMI25.1 R'8 Z'9 OC2CH2OC2H5 2-F-4-CF3O OCH2CH2SCH3 2-F-4-1 OCH(CH3)CO2C2H5 3-Br-4-Cl SC6H5 2-CF3O-4-F NHCH2CH2OH 2-CH3-4-Br NHCH2CH2OH 3-F-4-Cl NHCH2CN 3,5-Cl2 NHCH2CO2CO2C2H5 2-CH3-4-Br NHCH2CO2C2H5 2-F-4-Br NHCH2CN 2,4-B$2 TABLE 3 Representative Malontc Acid Derivative Compounds EMI26.1 Y'4 Y'5 Z'10 R'9 Cl Cl 2-CH3-4-Br OC2H5 Cl H 4-Cl OC2H5 Br Br 2,4-Cl2 OC2H5 Br H 3,5-Br2 OC2H5 Cl Br 3,4-Cl2 OCH3 CH3 Cl 3,5-Cl2 OH F F 2,4 Br2 OC2H5 F F 2-F-4-Br OC2H5 CH3O- H 2-F-4-Cl O.n C3H7 CH3O- CH3O- 3-Cl-5-Br OCH2CH2OCH3 F H 3,4 Br2 SCH2CO2C2H5 O2N- H 2-Cl 4 Br OCH3 O2N- H 2-Cl-4-Br OCH(CH3)C@H O2N- O2N- 2 CH3-4 Br SC7H5 O2N- CH3 2,4-Br2 ON@C(CH3)2 TABLE 3 (Cont.) Representative Malonic Acid Derivative Compounds EMI27.1 EMI27.2 Y'4 <SEP> Y'5 <SEP> Z'10 <SEP> R'9 <tb> CH2.CH- <SEP> H <SEP> 3.5-Br2 <SEP> OH <tb> N2C- <SEP> H <SEP> 2-CH3-4-Br <SEP> OC2H5 <tb> N2C- <SEP> H <SEP> 2.4-Cl2 <SEP> OCH3 <tb> N2C- <SEP> CH3 <SEP> 3-F-4-Br <SEP> OCH2CONH2 <tb> O2N- <SEP> Cl <SEP> 2,4,5-Cl3 <SEP> OCH2CH2OH <tb> N2C- <SEP> Br <SEP> 3-Br-5-F <SEP> OCH2CH2SCH3 <tb> HCONH- <SEP> H <SEP> 3.5-(CF3)2 <SEP> OC2H5 <tb> HC2C- <SEP> H <SEP> 2.5-Cl2 <SEP> SC6H5 <tb> C2H5 <SEP> F <SEP> 3-Cl-5-CF3 <SEP> OCH2COCH3 <tb> CH3O- <SEP> CH3 <SEP> 4 <SEP> Br <SEP> OCH3 <tb> # <SEP> H <SEP> 4-Cl <SEP> OC2H5 <tb> # <SEP> CH3 <SEP> 2-Cl3-4-Cl <SEP> OH <tb> HO- <SEP> HO- <SEP> 2 <SEP> CH3-4 <SEP> Br <SEP> OC2H5 <tb> TABLE 3 (Cont.) Representative Malonic Acid Derivative Compounds EMI28.1 Y'4 Y'5 Z'10 R'9 CH3 H 2-Cl-4-CF3O SC6H5 CH3 CH3 2-CF3O-4 F OCH3 CH3 Br 2-CH3-4 C@3CF2O O.n.C3H7 CH3 C2H5 2-CH3-4.1 OH C2H5 Br 3-Br-4-Cl OC2H5 CH3O CH3 2-@-4-1 ONa HOCH2 HOCH2 2,4 Cl2 OCH3 CH3CO. H 4-Br OC2H5 CH3CO. CH3 2-Cl-4-Br OCH3 -CHO Br 2 CH3-4-Cl SCH3 -CHO Cl 3,4 Br2 OC2H5 (C2H5O)2CH- Cl 4 Cl OCH3 (CH3O)2CH- Br 2 CH3@ Br O n C3H7 H2NC- CH3 2,4 Cl2 OCH3 5 TABLE 3 (Cont.) Representative Malonic Acid Derivative Compounds EMI29.1 Y'4 Y'5 Z'10 R'9 CH3CONH- H 2-CH3-4-Br SC2H5 HCONH- H 2-F-4-Br SC6H5 HCl@H2N- H 2-C2H5-4-Cl OCH3 -O-CH2-O- 2-CH3-4-Br SCH2CH2OCH3 -S-CH2CH2S- 2-CH3-4-Br OC2H5 CH3O H 3,5-Cl2 OC2H5 CH3O H 3,5-Br2 OC2H5 CH3O H 3-Br-5-Cl O-n-C3H7 CH3O H 3-Br#5-F O-@-C4H9 C2H5OCO CH3 4-Cl OCH3 CH3S CH3 3,5-Cl2 OC2H5 CH3SO CH3 2-F-4-Br O-n-C3H7 CH3SO2 H 2-CH3-4-Br OC2H5 CH3SO2 CH3 3,5-Cl2 OC2H5 C-N- H 2-CH3-4-Br OC2H5 CH3S H 2-CH3-4-Br OC2H5 TABLE 4 Representative Malonic Acid Derivative Compounds EMI30.1 Y'7 Y'8 Y'9 Y'10 Y'6 R'10 Z'11 H H H H H OH 2-C2H5-4-Cl H H H H H OCH3 2-C2H5-4.Cl H H H H H OH 2-C2H5-4 Br H H H H H OC2H5 2-C2H5-4-Br H H H H CH3 OH 4 Cl H H H H CH3 ONa 4 Br H H H H CH3 OH 3,4 Cl2. H H H H CH3 OC2H5 2 Cl-4-Br H H H H CH3 OH 2 @-4 Br H H H H H OH 3-@-4 Cl H H H H H OCH3 3 @ 4-Br H H H H H NH2 2 CH3-4-Br H H H H ONH4 2.CH3-4 Br H H CH3 H H OH 2 @ 4-Cl Cl Cl CH3 H H OK 2 CH3 4 Cl TABLE 4 (Cont.) Representative Malonic Acid Compounds EMI31.1 Y'7 Y'8 Y'9 Y'10 Y'6 R'10 Z'11 H H CH3 CH3 H OC2H5 2,4-Cl2 CH3 CH3 CH3 H ONa 2-CH3-4-Br CH3 H H H H OH 4-Cl CH3 CH3 H H H ONH4 2-C2H5-4-Cl Cl H H H OH 2-F-4-Br Cl Cl H H OCH3 2,4-Br2 Cl Cl CH3 CH3 H OH 4 Cl H H H H H OH 2-CH3O-4,5-Cl2 H H H H H OH 2-CH3O-3,5-Cl2 H H H H H ONa 2-CF3-4-Cl H H H H H OCH3 2-CF3O-4-CF3 H H H H H OK 2-F-4-1 H H H H H OH 3-Br-4-Cl C2H5 H H H H OH 2-CH3-4-Br H H CH3 CH3 H OC2H5 2.4-Cl2 CH3 CH3 CH3 CH3 H ONa 2-CH3-4-Br Cl Cl CH3 CH3 H OH 4 Cl TABLE 5 Representative Malonic Acid Derivative Compounds EMI32.1 Y'11 Y'12 Y'13 Y'14 Y'15 Y'16 R'11 Z'12 H H H H H H OC2H5 2,4 Cl2 H H H H H H OH 2,4 Cl2 H H H H H H OC2H5 3,4.Cl2 H H H H H H OH 3,4 Cl2 H H H H H H OC2H5 4 Cl H H H H H H OH 4 Cl H H H H H H OCH3 2 @ 4 Cl H H H H H H ONa 2 @ 4 Br H H H H H H ONH4 2 Cl 4.Br H H H H H H OCH3 2 Br.4 Cl H H H H H H OK 4 Br H H H H H H OH 2 CF3 4 Br CH3 CH3 H H H H OH 2 CH3 4 Br H H CH3 CH3 H H OCH3 4 Cl CH3 H CH3 H H H ONa 4 Br TABLE 5 (Cont.) Representative Malonic Acid Derivative Compounds EMI33.1 Y'11 Y'12 Y'13 Y'14 Y'15 Y'16 R'11 Z'12 CH3 CH3 CH3 H H H NH2 2,4 Br2 Cl Cl H H H H OH 3,4-Cl2 H H Cl Cl H H OCH3 2-C2H5-4-Br CH3 H H H Cl Cl ONH4 4 Cl Cl H H H Cl H OC2H5 3 F-4-Cl Cl Cl CH3 H Cl H OH 3,4 Br2 CH3 Cl H H H H OCH3 2-CH3-4-Cl CH3 CH3 CH3 Cl H H ONa 3,4 Cl2 H H H H H H OH 3.Br 4 Cl H H H H H H ONa 2-CH3O-4,5 Cl2 H H H H H H OH 2 CH3O 3.5-Cl2 H H H H H H OCH3 2 C@3 4 Br H H H H H H OK 2.C@3O 4 Cl H H H H H H OH 2 C2H5 4 1 TABLE 6 Representative Malonic Acid Berivative Compounds EMI34.1 Y'18 Y'19 Y'20 Y'21 Y'17 Z'13 R'12 H H H H H 2-CH3-4 Br OCH2CH2OCH3 H H H H H 2 CH3-4 Br OCH2CH2OH H H H H H 4 Cl OCH2CH2SO2CH3 H H H H H 2-Cl-4-Br OCH2COCH3 H H H H H 2-@-4-Br OCH(CH3)C@N H H H H H 2-CH3-4 Br OCH2CH2SO2CH2OH H H H H CH3 3,4 Br2 OCH2CH2OH CH3 CH3 CH3 H H 4 Br O N-CHCH3 Cl Cl CH3 H H 2,4 Cl2 OCH2CONH2 H H CH3 CH3 CH3 4-Cl SCH3 CH3 H CH3 CH3 H 3-F 4 Cl SCH2CO2CH3 Cl Cl CH3 CH3 H 2 C@3-4-Br OCH2CH2OH H H H H H 2,4 Br2 OCH2CH2OCH2CH2OH H H H H H 3 Br-4 Cl SC6H5 H H H H H 2 Cl3O 4 1 OCH2CH2OH H H H H H 2 Cl3 4 1 OCH2COCH3 TABLE 7 Representative Malonic Acid Derivative Compounds EMI35.1 EMI35.2 Y'21 <SEP> Y'22 <SEP> Y'23 <SEP> Y'24 <SEP> Y'25 <SEP> Y'26 <SEP> Z'14 <SEP> R'13 <tb> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> 2 <SEP> CH3 <SEP> 4 <SEP> Br <SEP> OCH2CH2OCH3 <tb> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> 2 <SEP> CH3 <SEP> 4 <SEP> Br <SEP> OCH2CH2SO2CH2CH2OH <tb> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> 2,4 <SEP> Br@ <SEP> OCH2CH2OCH2CH2OH <tb> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> 3,4 <SEP> Cl@ <SEP> SCH2CO2C2H5 <tb> CH3 <SEP> CH3 <SEP> H <SEP> H <SEP> H <SEP> H <SEP> 2 <SEP> @ <SEP> 4 <SEP> Br <SEP> O.N=CHCH3 <tb> CH3 <tb> H <SEP> H <SEP> CH3 <SEP> CH3 <SEP> H <SEP> H <SEP> 2 <SEP> CH3 <SEP> 4 <SEP> Cl <SEP> O-N@C <tb> SCH3 <tb> Cl <SEP> Cl <SEP> H <SEP> H <SEP> H <SEP> H <SEP> 2 <SEP> Cl3 <SEP> 4 <SEP> Br <SEP> OCH2CONH2 <tb> H <SEP> H <SEP> Cl <SEP> Cl <SEP> H <SEP> H <SEP> 4 <SEP> Cl <SEP> OCH2C@N <tb> H <SEP> H <SEP> H <SEP> H <SEP> Cl <SEP> Cl <SEP> 4 <SEP> Br <SEP> SCH2P(OC2H5)2 <tb> O <tb> CH3 <SEP> Cl <SEP> H <SEP> H <SEP> H <SEP> H <SEP> 3 <SEP> @ <SEP> 4 <SEP> Cl <SEP> OCH2CH2NHCO2C2H5 <tb> CH3 <SEP> H <SEP> Cl <SEP> Cl <SEP> H <SEP> H <SEP> 2.4 <SEP> Cl2 <SEP> OCH2COCH3 <tb> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> 2 <SEP> Cl3 <SEP> 4 <SEP> C@3O <SEP> OCH2CH2CONH2 <tb> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> 2 <SEP> C2H5 <SEP> 1 <SEP> @ <SEP> OCH2CH2OH <tb> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> H <SEP> 2 <SEP> Br <SEP> 4 <SEP> Cl3 <SEP> SCH2CH2OCH3 <tb> TABLE 8 Representative Malonic Acid Derivative Compounds EMI36.1 Y'28 Y'21 R'14 Z'15 -CH2CH2- S OH 2,4 Cl2 -CH2CH2- O OH 2.4 Br2 -CH2CH2- O OH 2-Br-4-C6H5O -CH2CH2- S OCH3 3,5-Cl2 -CH2CH2- S NH2 2-@-4-Cl -CH(CH3)CH2- O O Na 2.5 Cl2 -CH2CCl2- S NHCH3 2-CH3O-4,5-Cl2 -CH2C(CH3)2- O NHCH2CH2OH 4 (4 ClC6H4O) -CH2CH2CH2- S OC2H5 2,4 Cl2 -CH2CH2CH2- S OCH3 3,5-Br2 -CH2CH2CH2- O NH2 2-Cl 4 Br -CH2CH2CH2- O OCH2CH2OH 2 CH3-4,5 Br2 -CH2CH2CH2- S OCH3 2,4,5.Cl3 -CH2CH2CH2- S O n C3H@ 2-Br-5-C6H5O -CH2CH2CH2CH2- O OC2H5 3,4-Cl2 TABLE 8 (Cont.) Representative Malonic Acid Derivative Compounds (Cont.) EMI37.1 Y'28 Y'21 R'14 Z'15 -CH2CH2CH2CH2- S OC2H5 2,4-Cl2 -CH2CH2CH2CH2- O NH2 2-Br-4 CN -CH2CH2CH2CH2- O OC2H5 4 C6H5O -CH2CH2CH2CH2- S OH 3,5 Cl2 -CH2CH2CH2CH2- O NHCH2CH2OCH3 4 Cl -CH2CH2- O SC6H5 3,4 Br2 -CH2CH2CH2- O SCH2CH2OH 3-Br-5 Cl -CH2CH2CH2- O SCH3 2-Cl3-4-Br -CH2CH2- S OCH3 3,5-(C@3)2 TABLE 9 Representative Malonic Acid Derivative Compounds EMI38.1 Y'30 Y'31 Y'29 R'15 Z'16 H H O OC2H5 3,5-Cl2 H H S OC2H5 2,4 Cl2 H H S O n-C3H7 2,4 Br2 H H S OCH3 2-Cl-4 C6H5O CH3 CH3 O OH 4 C6H5O CH3 Br S OCH3 2-Cl-4-Br N=C- H O OC2H5 3,5 Br2 N=C- CH3 S OC2H5 2,4 Cl C2H5 H O NHCH3 2 @ 4 Cl CH3O- H O NH2 2,4,5 Cl3 CH3O CH3O S OC2H5 2 Cl 4 Br N=C- Br O OCH@ 2,4 Cl2 O2N CH3 S SC6H5 4 Br CH3O- CH3 O SCH2CH2OC2H5 2 Br 4 @N TABLE 10 Representative Malonic Acid Derivative Compounds EMI39.1 Y'33 Y'34 Y'32 R'16 Z'17 H H NH OC2H5 2-CH3-4 Br H H NH OC2H5 2-F-4 Br H H NH OC2H5 2-F-4-Cl H H NH OC2H5 3,5-Cl2 H H NH OH 3,4 Br2 H H NH OCH3 2,4,5-Cl3 CH3 H NH OC2H5 2-CH3-4 Br CH3 H NH OCH3 3,5 Br2 CH3 H NH SCH2CH2OCH3 4 Cl CH3 H N(CH3) OCH2CH2OH 3-F-4 Br CH3 H O NH2 3,4 Cl2 CH3 H S OCH3 2,4 Cl2 CH3 H NH OH 2 CH3 4 Br 5 Cl CH3 H NH OC2H5 2 CH3O 4,5 Cl2 CH3 CH3 NH OC2H5 4 Cl TABLE 10 (Cont.) Representative Malonic Acid Derivative Compounds EMI40.1 <RTI ID=40.2> Y'33 Y'34 Y'32 R'16 Z'17 CH3 CH3 NH OC2H5 2,4.Cl2 CH3 CH3 NH OC2H5 3,4 Br2 CH3 CH3 NH OC2H5 3-Cl-5-Br CH3 CH3 NH OH 3,5 (C@3)2 CH3 CH3 NH OH 2-C@3-4-Br CH3 CH3 NH OCH3 3-C@3-5-Cl CH3 CH3 O OC2H5 2-Cl-4-C6H5O CH3 CH3 S OCH3 2,4 Cl2 CH3 CH3 S OH 3,5 Cl2 H H O OCH2CN 3,4 Br2 H H S OCH2CH2OCH3 2-Br-4 CN C2H5 H NH OC2H5 2-CH3-4-Br C2H5 H NH OCH3 2,4 Br2 Cl Cl NH OC2H5 2 CH3-4 Br TABLE 10 (Cont.) Representative Malonic Acid Derivative Compounds EMI41.1 Y'33 Y'34 Y'32 R'16 Z'17 Br Br NH OC2H5 4-Cl CH3S- CH3S- NH OCH3 3,4-Cl2 CH3O CH3O NH OCH3 2-F-4-Cl CH3CCl2- H NH 5-n-C3H7 3,5-Br2 -S-CH2CH2-S- NH OCH3 3,5-Cl2 -S-CH2CH2-NH- NH SC6H5 2,4-Br2 C2H5 H NH OCH3 2,4-Br2 Cl Cl NH OC2H5 2-CH3-4-Br TABLE 11 Representative Malonic Acid Derivative Compounds EMI42.1 EMI42.2 Y'36 <SEP> Y'37 <SEP> Y'35 <SEP> R'18 <SEP> R'17 <tb> H <SEP> H <SEP> NH <SEP> OC2H5 <SEP> # <tb> S <SEP> Cl <tb> H <SEP> H <SEP> NH <SEP> OC2H5 <SEP> # <tb> O <tb> Cl <tb> N <tb> H <SEP> H <SEP> NH <SEP> O-n <SEP> C3H7 <SEP> # <SEP> Cl <tb> N <tb> Cl <tb> TABLE 11 (Cont.) Representative Malonic Acid Derivative Compounds EMI43.1 EMI43.2 Y'36 <SEP> Y'37 <SEP> Y'35 <SEP> R'18 <SEP> R'17 <tb> Cl <tb> C2H5 <SEP> C2H5 <SEP> O <SEP> SC6H5 <SEP> # <tb> N <tb> Cl <tb> Cl <tb> CH3 <SEP> Br <SEP> S <SEP> NHC2H5 <SEP> # <SEP> Cl <tb> N <tb> OC6H5 <tb> N@C <SEP> CH3 <SEP> S <SEP> SCH2CH2OCH3 <SEP> # <tb> N <tb> N@C <SEP> Cl <SEP> N(CH3) <SEP> OCH2CH-CH2 <SEP> # <SEP> O <SEP> # <SEP> Cl <tb> N <SEP> H <tb> TABLE 11 (Cont.) Representative Malonic Acid Derivative Compounds EMI44.1 EMI44.2 Y'36 <SEP> Y'37 <SEP> Y'35 <SEP> R'18 <SEP> R'17 <tb> H <SEP> H <SEP> NH <SEP> OCH3 <SEP> # <SEP> Cl <tb> N <SEP> N <tb> Cl <tb> N <tb> H <SEP> H <SEP> NH <SEP> OC2H5 <SEP> # <SEP> N <tb> N <tb> Cl <tb> CN <tb> CH3 <SEP> H <SEP> NH <SEP> O-n <SEP> C3H7 <SEP> # <tb> N <tb> Cl <tb> It is appreciated that the particular compounds listed in Tables 1 through 11 hereinabove are illustrative of malonic acid derivative compounds which can be used for retarding plant growth according to this invention. This invention is not to be construed as being limited only to the use of these compounds; but rather, this invention includes the use of those malonic acid derivative compounds encompassed within formula 7 hereinabove. The novel malonic acid derivative compounds of this invention can be depicted by the following formulae: EMI45.1 wherein: Z1 is independently substituted or unsubstituted halogen, haloalkyl, polyhaloalkyl, polyhaloalkoxy, alkyl, alkoxy, alkylthio, alkylsulfonyl, alkylsulfinyl, aryl, aryloxy, arylthio, arylsulfonyl, nitro, cyano, dialkoxyphosphinyl, acyl, aroyl, alkoxycarbonyl, alkoxycarbonylalkyl, acylamino, sulfonylamino, alkylsulfonylamino, acyloxy, alkenyl or -CH=CHCH=CH-; n is a value of from 0 to 5; V11 is 0, S or NR7 wherein R7 is hydrogen or alkyl; Y12 is 0, S, NH or N (alkyl); and R6 is ammonium, alkylammonium, polyalkylammonium, hydroxyalkylammonium, poly(hydroxyalkyl)ammonium, an alkali metal or alkaline earth metal or substituted or unsubstituted hydroxyalkyl, alkoxyalkyl, alkoxycarbonylalkyl, alkylaminoalkyl, dialkylaminoalkyl, aryl, mercaptoalkyl, alkylthioalkyl, arylthioalkyl, aryloxyalkyl, alkylsulfonylalkyl, alkylsulfinylalkyl, acylalkyl, aroylalkyl, dialkoxyphosphinylalkyl, diaryloxyphosphinylalkyl, hydroxyalkylthioalkyl, hydroxyalkylsulfonylalkyl, alkoxyalkylthioalkyl, alkoxyalkylsulfohylalkyl, poly(oxyalkylene)alkyl, cyanoalkyl, nitroalkyl, alkylideneamino, carbamoylalkyl, alkylcarbamoylalkyl, dialkylcarbamoylalkyl, aminoalkyl, acylaminoalkyl, acyloxyalkyl, alkoxycarbonylaminoalkyl, cyanoaminoalkyl, carbamoyloxyalkyl, alkylcarbamoyloxyalkyl, dialkylcarbamoyloxyalkyl, alkoxycarbonyloxyalkyl, alkoxycarbonylthioalkyl, aminosulfonylalkyl, alkylaminosulfonylalkyl or dialkylaminosulfonylalkyl; EMI46.1 wherein: Z2 is independently substituted or unsubstituted halogen, haloalkyl, polyhaloalkyl, polyhaloalkoxy, alkyl, alkoxy, alkylthio, alkylsulfonyl, alkylsulfinyl, aryl, aryloxy, arylthto, arylsulfonyl, nitro, cyano, dialkoxyphosphinyl, acyl, aroyl, alkoxycarbonyl, alkoxycarbonylalkyl, acylamino, sulfonylamino, alkylsulfonylamino, acyloxy, alkenyl or -CH=CHCH=CH-; n is a value of from 0 to 5; V13 is 0, S or NR9 wherein R9 is hydrogen or alkyl; Y14 is 0, S, NH or N (alkyl); ; Y15 and V16 are independently hydrogen, alkyl, halogen, alkoxy, alkylthio, alkenyl, alkynyl, hydroxy, cyano, nitro, formyl, amino, alkylcarbonyl, dialkoxyalkyl, alkylcarbonylamino, formylamino, hydroxyalkyl, haloalkyl or polyhaloalkyl provided that when Y15 is alkyl then Z2 Is not halogen or polyhaloalkyl at the para- position, and further provided that at least one of V15 and Y16 is other than hydrogen; V15 and V16 may be linked together to form a substituted or unsubstituted heterocyclic ring system selected from a monocyclic aromatic or nonaromatic ring system, a bicyclic aromatic or nonaromatic ring system, a polycyclic aromatic or nonaromatic ring system and a bridged ring system which may be saturated or unsaturated; and R8 is hydrogen or R R6;, EMI47.1 wherein: Z3 is independently substituted or unsubstituted halogen, haloalkyl, polyhaloalkyl, polyhaloalkoxy, alkyl, alkoxy, alkylthio, alkylsulfonyl, alkylsulfinyl, aryl, aryloxy, arylthio, arylsulfonyl, nitro, cyano, dialkoxyphosphinyl, acyl, aroyl, alkoxycarbonyl, alkoxycarbonylalkyl, acylamino, sulfonylamino, alkylsulfonylamino, acyloxy, alkenyl or -CH=CHCH=CH-; n is a value of from 0 to 5; V17 is 0, S or NRll wherein R11 is hydrogen or alkyl; V18 is O or S; V19 and Y20 are independently hydrogen, alkyl, alkoxy, alkylthio, halogen, haloalkyl or polyhaloalkyl; or Y19 and Y20 may be linked together to form a substituted or unsubstituted, carbocyclic or heterocyclic ring system selected from a monocyclic aromatic or nonaromatic ring system, a bicyclic aromatic or nonaromatic ring system, a polycyclic aromatic or nonaromatic ring system and a bridged ring system which may be saturated or unsaturated; and R10 is hydrogen or R6; and EMI48.1 wherein: R1 and R2 are independently a substituted or unsubstituted, carbocyclic or heterocyclic ring system selected from a monocyclic aromatic or nonaromatic ring system, a bicyclic aromatic or nonaromatic ring system, a polycyclic aromatic or nonaromatic ring system, and a bridged ring system which may be saturated or unsaturated; or R1 and R2 are independently hydrogen or derivative salts, or a substituted heteroatom or substituted carbon atom, or a substituted or unsubstituted, branched or straight chain containing two or more carbon atoms or heteroatoms in any combination; Y1 and V2 are independently a substituted or unsubstituted heteroatom; V3 and V4 are linked together to form a substituted or unsubstituted, carbocyclic or heterocyclic ring system selected from a monocyclic aromatic or nonaromatic ring system, a bicyclic aromatic or nonaromatic ring system, a polycyclic aromatic or nonaromatic ring system, and a bridged ring system which may be saturated or unsaturated; and V5 and V6 are independently oxygen or sulfur; in which the permissible substituents for formulae (i) through (iv) above are Z as hereinbefore defined. Novel malonic acid derivative compounds within the scope of formula (iv) above can be depicted by the following formulae: EMI49.1 wherein: Z4 is independently substituted or unsubstituted halogen, haloalkyl, polyhaloalkyl, polyhaloalkoxy, alkyl, alkoxy, alkylthio, alkylsulfonyl, alkylsulfinyl, aryl, aryloxy, arylthio, arylsulfonyl, nitro, cyano, dialkoxyphosphinyl, acyl, aroyl, alkoxycarbonyl, alkoxycarbonylalkyl, acylamino, sulfonylamino, alkylsulfonylamino, acyloxy, alkenyl or -CH=CHCH=CH-; n is a value of from O to 5; Y21 is 0, S or NR13 wherein R13 is hydrogen or alkyl; Y22 is 0, S, NH or N (alkyl); Y23, Y24, Y25 and Y26 are independently hydrogen, alkyl or halogen; and R12 is hydrogen or R6; or EMI50.1 wherein: Z5 is independently substituted or unsubstituted halogen, haloalkyl, polyhaloalkyl, polyhaloalkoxy, alkyl, alkoxy, alkylthio, alkylsulfonyl, alkylsulfinyl, aryl, aryloxy, arylthio, arylsulfonyl, nitro, cyano, dialkoxyphosphinyl, acyl, aroyl, alkoxycarbonyl, alkoxycarbonylalkyl, acylamino, sulfonylamino, alkylsulfonylamino, acyloxy, alkenyl or -CH=CHCH=CH-; n is a value of from 0 to 5; Y27 ts O, S or NR15 wherein R15 is hydrogen or alkyl; V28 is O S, NH or N (alkyl); Y29' V30, V31, V32, Y33 and Y34 are independently hydrogen, alkyl or halogen; and R14 is hydrogen or R6; EMI51.1 wherein: Z6 is independently substituted or unsubstituted halogen, haloalkyl, polyhaloalkyl, polyhaloalkoxy, alkyl, alkoxy, alkylthio, alkylsulfonyl, alkylsulfinyl, aryl, aryloxy, arylthio, arylsulfonyl, nitro, cyano, dialkoxyphosphinyl, acyl, aroyl, alkoxycarbonyl, alkoxycarbonylalkyl, acylamino, sulfonylamino, alkylsulfonylamino, acyloxy, alkenyl or -CH=CHCH=CH-; n is a value of from 0 to 5; Y35 is O, S or NRl7 wherein R17 is hydrogen or alkyl; V36 is O or S; and R16 is hydrogen or R6; in which the permissible substituents for formulae (v) through (vii) are as described for Z above for formulae (i) through (iv). The malonic acid derivative compounds encompassed within formula I and the intermediate compounds used in the preparation thereof can be prepared by conventional methods known in the art and many may be available from various suppliers. The novel malonic acid derivative compounds of formulae (i) through (vii) above which can be used in the method of this invention can be prepared by reacting appropriate starting ingredients in accordance with conventional procedures described in the art as illustrated below. The novel malonic acid derivative compounds of formula (i) can be prepared by the following general reaction scheme: EMI52.1 Scheme I wherein Zl, n, Yell, V12 and R6 are as defined hereinabove. Reactions of this general type for preparing malonic acid derivative compounds of formula (i) including process conditions are described for example by Richter, G.H., Textbook of Organic Chemistry, Third Edition, John Wiley and Sons, New York, p. 486. In the Schotten-Baumann procedure described therein, cold aqueous sodium hydroxide is illustrated as the acid acceptor. The novel malonic acid derivative compounds of formula (ii) can be prepared by the following general reaction scheme: EMI53.1 Scheme II wherein Z2, n, V13, V4, Y15, V16 and R8 are as defined hereinabove. Reactions of this general type for preparing malonic acid derivative compounds of formula (ii) including process conditions are described for example by Richter, G.H., supra, according to the known Schotten-Baumann procedure. The novel malonic acid derivative compounds of formula (iii) can be prepared by the following general reaction scheme: EMI54.1 Scheme III wherein Z3, n, Y17, Y18, Y19, Y20 and R10 are as defined hereinabove. Reactions of this general type for preparing malonic acid derivative compounds of formula (iii) including process conditions are described for example by Richter, G.H., supra, according to the known Schotten-Baumann procedure. The novel malonic acid derivative compounds of formula (iv) can be prepared by the following general reaction scheme: EMI55.1 Scheme IV wherein R1, R2, Y1, Y2, Y3, Y4, Y5 and V6 are as defined hereinabove. Reactions of this general type for preparing malonic acid derivative compounds of formula (iv) including process conditions are described for example by Richter, G.H., supra, according to the known Schotten-Baumann procedure. The novel malonic acid derivative compounds of formula (v) can be prepared by the following general reaction scheme:' EMI56.1 Scheme V wherein Z4, n, Y21, Y22, Y23, Y24, Y25' Y26 and Rl2 are as defined hereinabove. Reactions of this general type for preparing malonic acid derivative compounds of formula (v) including process conditions are described for example by Richter, G.H., supra, according to the known Schotten-Baumann procedure. The novel malonic acid derivative compounds of formula (vi) can be prepared by the following general reaction scheme: EMI57.1 Scheme VI wherein Z5, n, Y27, Y28, Y29, Y30, Y37' 32' Y33, Y34 and R14 are as defined hereinabove. Reactions of this general type for preparing malonic acid derivative compounds of formula (vi) including process conditions are described for example by Richter, G.H., supra, according to the known Schotten-Baumann procedure. The novel malonic acid derivative compounds of formula (vii) can be prepared by the following general reaction scheme: EMI58.1 Scheme VII wherein Z62 n, V35, Y36 and R16 are as defined hereinabove. Reactions of this general type for preparing malonic acid derivative compounds of formula (vii) including process conditions are described for example by Richter, G.H., supra, according to the known Schotten-Baumann procedure. In addition to the above, other illustrative procedures which can be employed in preparing malonic acid derivative compounds encompassed within formula 1 and intermediate compounds used in the preparation thereof are described, for example, in the following: Breslow, D.S. et al., Jour. Amer. Chem. Soc. 66, 1286-1288 (1944); Svendsen, A. and Boll, P.M., Jour. Org. Chem. 40, 1927-1932 (1975); Sen, A.K. and Sengupta, P., J. Ind. Chem. Soc. 46, (9), 857-859 (1969); Thiers, R. and Van Dormael, A., Bull. Soc. Chim. Belg. 61, 245-252 (1952); Brown, R.F.C., Austral. Jour. of Chem. 8 121-124 (1955); U.S. Patent 3,951,996; United Kingdom Patent 1,374,900; Chiriac, C.I., Revue Romaine de Chime 25, (3), 403-405 (1980); Weiner, N., Org, Syn. Coll., Vol. II, 279-282 (1950), Sixth Printing, John Wiley & Sons, New York; Block, Jr., Paul, Org, Syn, Coll. Vol. V, 381-383 (1973), John Wiley and Sons, New York; Reliquet, F. et al., Phos. and Sulfur 24 279-289 (1985); Palmer, C.S. and McWherter, P.W., Org. Syn. Coll. Vol. I, 245-246 (1951), Second Edition, John Wiley and Sons, New York; Straudinger, H. and Becker, H., 8erichte 50, 1016-1024 (1917); Purrington, S.T. and Jones, W.A., J. Org. Chem. 48, 761-762 (1983); Kitazume, T. et al., Chem. Letters (1984) 1811-1814; Wolff, I.A. et al., Synthesis (1984), 732-734; Zambito, A.J. and Howe, E.E.., Org. Syn, Coll. Vol. V, 373-375 (1973), John Wiley and Sons, New York; and Hartung, W.H. et al., Org. Syn. Coll. Vol. V, 376-378, John Wiley and Sons, New York. Still other illustrative procedures which can be employed in preparing malonic acid derivative compounds encompassed within formula 1 and intermediate compounds used in the preparation thereof are described, for example, in the following: Rathke, M.W. and Cowan, P.J., J. Org. Chem. 50, 2622-2624 (1985); Fones, W.S., Org. Syn, Coll. Vol. IV, 293 (1963), John Wiley and Sons, New York; Gompper, R. and Topfl, W., Chem. Ber. 95, 2861-2870 (1962); Gompper, R. and Kunz, R., Chem. Ber. 99, 2900-2904 (1966); Ono, N. et al., J. Org. Chem. 50, 2807-2809 (1985); U.S. Patent 4,154,952; Blankenship, C. and Paquette, L.A., Synth. Comm 14, (11), 983-987 (1984); Baldwin, J.E. et al., Tet. Lett. 26, (4), 481-484 (1985); Kawabata, N. et al., Bull. Chem. Soc. Jpn. 55, (8), 2687-2688 (1982); Bodanszky, M. and du Vignaud, V., J. Am. Chem. Soc. 81, 5688-5691 (1959); Neelakantan, S. et al., Tetrahedron 21, 3531-3536 (1965); U.S. Patent 4,020,099; Japan Patent Application 148,726 (1979); Fuson, R.C., Advanced Organic Chemistry, p. 202 (1950), John Wiley and Sons, New York; Duty, R.C., Anal. Chem. 49, (6), 743-746 (1977); Korner, G., Contradi, AHI acad. Lincei 22, T, 823-836 (C.A. 8, 73 (1914)); Schimelpfenig, C.W., J. Chem. Soc. Perk. Trans. I, 1977 (10), 1129-1131; Kim, Y.S. et al,, Taehan Hwahak Hoechi 18, (4), 278-288 (1974); German Patent 2,449,285; U.S. Patent 3,962,336; and U.S. Patent 3,992,189. Copending U.S. Patent Application Serial No. (D-15299), filed on an even date herewith, describes the use of malonic acid derivative compounds of formula 1 for increasing crop yield. Copending U.S. Patent Application Serial No. (0-15298), filed on an even date herewith, describes synergistic plant growth regulator compositions containing (i) an ethylene response or an ethylene-type response inducing agent and (ii) a malonic acid derivative compound of formula 1. Both of these applications are incorporated herein by reference. The malonic acid derivative compounds of formula 1 have been found to significantly retard plant growth in comparison with untreated plants at similar conditions. In addition, the malonic acid derivative compounds used in this invention are substantially non-phytotoxic to growing plants. As used herein, an effective amount of a malonic acid derivative compound for retarding plant growth refers to a growth retarding effective amount of the compound sufficient to retard plant growth. The effective amount of compound can vary over a wide range depending on the particular compound employed, the particular plant to be treated, environmental and climatic conditions, and the like. The amount of compound used preferably does not cause substantial phytotoxicity, e.g., foliar burn, chlorosis or necrosis, to the plant. In general, the compound can preferably be applied to plants at a concentration of from about 0.01 to 15 pounds of compound per acre as more fully described below, The malonic acid derivative compounds contemplated by formula 1 can be employed according to a variety of conventional methods known to those skilled in the art. Compositions cdntaining the compounds as the active ingredient will usually comprise a carrier and/or diluent, either liquid or solid. Suitable liquid diluents or carriers include water, petroleum distillates, or other liquid carriers with or without surface active agents. Liquid concentrates can be prepared by dissolving one of these compounds with a nonphytotoxic solvent such as acetone, xylene, nitrobenzene, cyclohexanone or dimethyl formamide and dispersing the active ingredients in water with the aid of suitable surface active emulsifying and dispersing agents. The choice of dispersing and emulsifying agents and the amount employed are dictated by the nature of the composition and the ability of the agent to facilitate the dispersion of the active ingredient. Generally, it is desirable to use as little of the agent as is possible, consistent with the desired dispersion of the active ingredient in the spray so that rain does not re-emulsify the active ingredient after it is applied to the plant and wash It off the plant, Nonionic, anionic, or cationic dispersing and emulsifying agents may be employed, for example, the condensation products of alkylene oxides with phenol and organic acids, alkyl aryl sulfonates, complex ether alcohols, quaternary ammonium compounds, and the like. In the preparation of wettable powder or dust compositions, the active ingredient is dispersed in and on an appropriately divided solid carrier such as clay, talc, bentonite, diatomaceous earth, fuller's earth, and the like. In the formulation of the wettable powders, the aforementioned dispersing agents as well as lignosulfonates can be included. The required amount of the active ingredient contemplated herein can be applied per acre treated in from 1 to 200 gallons or more of liquid carrier and/or diluent or in from about 5 to 500 pounds of inert solid carrier and/or diluent. The concentration in the liquid concentrate will usually vary from about 5 to 95 percent by weight and in the solid formulations from about 0.5 to about 90 percent by weight. Satisfactory sprays or dusts for general use contain from about 0.001 to about 100 pounds of active ingredient per acre, preferably from about 0.01 to about 15 pounds of active ingredient per acre, and more preferably from about 0.1 to about 5 pounds of active ingredient per acre. Formulations useful in the conduct of this invention can also contain other optional ingredients such as stabilizers or other biologically active compounds, insofar as they do not impair or reduce the activity of the active ingredient and do not harm the plant being treated, Other biologically active compounds include, for example, one or more insecticidal, herbicidal, fungicidal, nematicidal, miticidal, plant growth regulators or other known compounds, Such combinations can be used for the known or other purpose of each ingredient and may provide a synergistic effect, The malonic acid derivative compounds of formula 1 are preferably applied to plants under substantially average or normal growing conditions. The malonic acid derivative compounds used in this invention may be applied during the plant vegetative growth phase or the plant reproductive growth phase to obtain plant growth retardation. Such compounds are useful in agriculture, horticulture and related fields and can be applied in general to both gymnosperms and angiosperms, in particular, to vegetation such as woody plants and turfgrasses to retard plant growth, The compounds are useful, for example, in controlling the height of vegetation in right-of-way areas and for growth retardation following pruning of trees and shrubs and the like with no adverse ecological effect. As used herein, plants refer in general to any agronomic or horticultural plants, woody plants, ornamentals and turfgrasses. Illustrative of woody plants which can be treated by the malonic acid derivative compounds of formula 1 according to the method of this invention include, for example, red maple, sycamore, red oak, American elm, linden, ginkgo, oaks, ashes, maples, apple trees, Chinese elm, crabapples, Russian olive, silver maple, sugar maple, water oak, poplars, conifers and the like. Illustrative of other plants which can be treated by the compounds of formula 1 according to the method of this invention include, for example, corn, cotton, sweet potatoes, white potatoes, alfalfa, wheat, rye, rice, barley, oats, sorghum, dry beans, soybeans, sugar beets, sunflowers, tobacco, tomatoes, canola, deciduous fruit, citrus fruit, tea, coffee, olives, pineapple, cocoa, banana, sugar cane, oil palm, herbaceous bedding plants, woody shrubs, turfgrasses, ornamental plants, evergreens, trees, flowers, and the like. The malonic acid derivative compounds contemplated herein are effective In retarding plant growth. Such compounds have a high margin of safety in that when used in sufficient amount to provide a growth redardation effect, they do not burn or injure the plant, and they resist weathering which includes wash-off caused by rain, decomposition by ultraviolet light, oxidation, or hydrolysis in the presence of moisture or, at least, such decomposition, oxidation, and hydrolysis as would materially decrease the desirable plant growth retardant characteristic of the active ingredient or impart undesirable characteristics, for instance, phytotoxicity, to the active ingredients. Mixtures of the active compounds can be employed if desired as well as combinations of the active compounds with other biologically active compounds or ingredients as indicated above. This invention is illustrated by the following examples. Example I Preparation of ethyl 3-r(4-fluorophenyl)aminol- 3-oxopropanoate Into a nitrogen-purged, air-stirred reaction flask was charged 4.44 grams (0.04 mole) of 4-fluoroaniline, 4.05 grams (0.04 mole) of triethylamine and 200 milliliters of tetrahydrofuran solvent. A 6.02 gram (0.04 mole) portion of ethyl malonyl chloride was then added rapidly by a dropping funnel to the mixture with good stirring at room temperature followed by a few milliliters of tetrahydrofuran as a rinse. The temperature of the stirred mixture rose to 42"C and a white precipitate of triethylamine hydrochloride separated therefrom. The mixture was then stirred at ambient temperature for about 2 hours and the triethylamine hydrochloride filtered off, washed with solvent and dried to give 5.2 grams (0.04 mole). The filtrate was freed of solvent on a rotary evaporator and the resulting purple solid dissolved in methylene chloride, which solution was washed in succession with 2N HC1 (3 x 75 milliliters), and water (2 x 75 milliliters), and then dried over magnesium sulfate and solvent vacuum stripped to give a crude solid product. Recrystallization from ethyl acetatecyclohexane followed by flash column chromatography gave 3.47 grams (0.015 mole) of ethyl 3-((4-fluoro- phenyl)aminol-3-oxopropanoate having a melting point of 68"C-71"C. Elemental analysis of the product indicated the following: Analysis : C11H12FNO3 Calculated: C, 58.66; H, 5.37; N, 6.22 Found: C, 58.61; H, 5.35; N, 6.36 This compound is referred to hereinafter as Compound - 1. Example II In a manner similar to that employed in Example I, other compounds were prepared. The structures and analytical data for Compounds 2 through 76 are set forth in Table A below. TABLE A Representative Malonic Acid Derivative Compounds EMI68.1 Substituents Elemental Analysis Melting Compound R'1 Z'1 Y'1 Calculated Found Point No. C H N C H N C 2 C2H5 4-Cl N(CH3) 56.36 5.52 5.48 56.25 5.53 5.21 49-52 3 C2H5 4-CN NH 62.06 5.21 12.07 61.68 5.09 11.99 101-103 4 C2H5 4-C2H5 NH 63.86 6.51 5.32 63.79 6.57 5.34 67-70 5 C2H5 3,5-Cl2 NH 47.85 4.02 5.07 47.86 4.14 5.08 67-69 6 C2H5 3-CF3-4-Br NH 40.70 3.13 3.96 40.69 3.24 3.97 69-72 7 C2H5 2-F-4-Cl-5-P(-O)(OCH2CH3)2 NH 45.52 5.09 3.54 45.41 5.26 3.56 97-98 8 C2H5 2,6-(CH3)2-4-Br NH 49.69 5.13 4.46 49.63 5.67 4.96 143-145 9 C2H5 3-CH3-4-Br NH 48.01 4.70 4.67 49.25 5.24 4.65 62-65 10 C2H5 3-CF3 NH 52.36 4.36 5.09 51.98 4.53 5.22 71-72.5 11 C2H5 3-Cl NH 54.67 5.01 5.80 53.96 5.33 5.86 011 12 C2H5 3,4-Cl2 O 47.68 3.64 - 46.63 3.86 - 011 13 C2H5 2,4-(CH3)2 NH 66.36 7.28 5.95 66.52 7.00 5.76 98-99 14 C2H5 3,4-(CH3)2 NH 66.36 7.28 5.95 66.29 7.26 5.90 68-70 15 C2H5 2-Cl-4-F NH 50.88 4.27 5.39 50.52 4.18 5.19 68-71 16 C2H5 2-Cl NH 54.67 5.01 5.80 54.58 5.11 5.72 54-57 TABLE A (Cont.) Representative Malonic Acid Derivative Compounds EMI69.1 Substituents Elemental Analysis Melting Compound R'1 Z'1 Y'1 Calculated Found Point No. C H N C H N C 17 C2H5 4-CH3 NH NMR (CDCl3): # 1.17-1.39 (t, 3H), 2.33 (s, 3H), 80-83 3.45 (s,2H), 4.07-4.42 (9,2H), 6.99-7.57 (m, 4H). 8.9-9.3 (br s, H) ppm. 18 C2H5 2,6-(CH3)2 NH NMR (CDCl3): # 1.15-1.46 (t,3H), 2.23 (s,6H), 97-100 2.50 (s,2H), 4.07-4.50 (q, 2H). 7.10 (s, 3H). 8.37-8.78 (br s,H) ppm. 19 C2H5 2-CF3-4-Cl NH 46.54 3.58 4.52 46.68 3.71 4.47 58.5-61 20 C2H5 2,3-Cl2 NH 47.85 4.02 5.07 47.84 4.05 5.07 72-75 21 C2H5 2,5-Cl2 NH 47.85 4.02 5.07 47.98 3.99 4.93 66-68 22 C2H5 3,5-Br2 NH 36.19 3.04 3.84 36.59 3.17 3.71 95-97 23 C2H5 2-CH3-5-Cl NH 56.37 5.52 5.48 56.76 5.72 5.26 96-98 24 C2H5 3,4,5-Cl3 NH 42.54 3.25 4.51 42.95 3.16 4.28 111-113 25 C2H5 2-CH3-4-Cl NH 56.37 5.52 5.48 56.00 5.67 5.21 103-104 26 C2H5 2,4-Cl2 NH 47.85 4.02 5.07 47.91 4.05 4.79 78-79 27 C2H5 4-CH3S- NH 56.89 5.97 5.53 56.75 5.90 5.48 73-75 TABLE A (Con Representative Malonic Acid Derivative Compounds EMI70.1 Substituents Elemental Analysis Melting Compound R'1 Z'1 Y'1 Calculated Found Point No. C H N C H N C 28 C2H5 3,5-(CF3)2 NH 45.49 3.23 4.08 45.96 3.23 4.02 72-75 29 C2H5 2-CH3O-5-Cl NH 53.04 5.19 5.16 53.65 5.31 5.14 86-87 30 C2H5 4-1 NH 39.66 3.63 4.20 39.30 3.68 4.08 108-110 31 C2H5 4-C2H5O- NH 62.13 6.82 5.57 62.45 7.03 5.77 100-101 32 C2H5 4-n-C4H9- NH 68.41 8.04 5.32 68.91 8.29 5.86 011 33 C2H5 4-n-C6H13O- NH 66.42 8.20 4.56 67.18 8.35 4.58 66-68 34 C2H5 4-n-C4H9O- NH 64.49 7.58 5.01 65.09 7.75 4.77 82-83 35 C2H5 2,4,5-Cl3 NH 42.54 3.25 4.51 42.40 3.09 4.39 104-105 36 C2H5 2,4-Br2 NH 36.19 3.04 3.84 36.29 2.93 3.77 83-85 37 C2H5 2-Cl-4-Br NH 41.21 3.46 4.37 41.29 3.42 4.35 78-80 38 C2H5 2-Br-4-Cl NH 41.21 3.46 4.37 41.59 3.61 4.55 81-83 39 C2H5 4-C6H5CO- NH 69.44 5.51 4.50 69.75 5.51 4.48 87-88.5 40 C2H5 3,4-Br2 NH 36.19 3.04 3.84 36.27 3.33 3.68 64-67 41 C2H5 2-F-4-Br NH 43.44 3.65 4.61 43.49 3.88 3.95 78.5-80 42 C2H5 2-CH3O-4-Cl NH 53.04 5.19 5.16 53.38 5.23 5.10 71-73 TABLE A (Cont.) Representative Malonic Acid Derivative Compounds EMI71.1 Substituents Elemental Analysis Melting Compound R'1 Z'1 Y'1 Calculated Found Point No. C H N C H N C 43 C2H5 2-CH3O-4,5-Cl2 NH 47.08 4.28 4.58 47.31 4.64 4.59 95-98 44 C2H5 2-CH3-3,4-Cl2 NH 49.67 4.52 4.83 49.86 4.62 4.69 90-93 45 C2H5 2-@-4-Cl NH 50.88 4.27 5.39 50.90 4.56 5.21 66-69 46 C2H5 3-Br-5-Cl NH 41.21 3.46 4.37 41.26 3.67 4.14 78-80 47 n-C4H9 2-CH3-4-Br NH 51.23 5.53 4.27 51.59 5.41 4.17 91-93 48 C2H5 2-CO2H-4-Br NH NMR (DMSO d6) : # 1.16-1.43 (t, 3H), 3.48 151-154 (s, 2H), 4.06-4.7 (m, 4H), 7.5-8.7 (m, 3H) ppm. 49 C2H5 2-CH3-3,5-Cl2 NH 49.67 4.52 - 49.22 4.43 - 116-120 50 C2H5 2-CH3-4,5-Cl2 NH 49.67 4.52 4.83 49.68 4.40 4.45 134-135.5 51 C2H5 2-C2H5-4-Cl NH 57.89 5.98 5.19 58.26 6.06 5.24 98-99 52 C2H5 2-CH3-3-Cl NH 56.37 5.52 5.48 56.49 5.49 5.47 103-105 53 C2H5 3-NO2-4-Cl NH 46.08 3.87 9.77 46.52 4.00 9.43 81-83 54 C2H5 2-CH3 NH 65.14 6.83 6.33 63.60 6.51 6.12 68-71 55 C2H5 2-CH3O NH 60.75 6.37 5.90 60 82 6.28 5.84 62-64 56 C2H5 2,5-(CH3)2-3,4-Cl2 NH 51.33 4.97 4.61 51.65 4.92 4.33 119-120 TABLE A (Cont Representative Malonic Acid Derivative Compounds EMI72.1 EMI72.2 Substituents <SEP> Elemental <SEP> Analysis <SEP> Melting <tb> Compound <SEP> R'1 <SEP> Z'1 <SEP> Y'1 <SEP> Calculated <SEP> Found <SEP> Point <tb> No. <SEP> C <SEP> H <SEP> N <SEP> C <SEP> H <SEP> N <SEP> C <tb> 57 <SEP> C2H5 <SEP> 2-CH3O-3,5-Cl2 <SEP> NH <SEP> 47.08 <SEP> 4.28 <SEP> 4.58 <SEP> 47.10 <SEP> 4.22 <SEP> 4.61 <SEP> 90-92 <tb> 58 <SEP> C2H5 <SEP> 2-CH3-4-Br-5-Cl <SEP> NH <SEP> 43.07 <SEP> 3.92 <SEP> 4.19 <SEP> 41.85 <SEP> 4.31 <SEP> 3.72 <SEP> 132-135 <tb> 59 <SEP> C2H5 <SEP> 4-(4-ClC6H4O) <SEP> NH <SEP> 61.18 <SEP> 4.83 <SEP> 4.20 <SEP> 61.27 <SEP> 4.94 <SEP> 4.14 <SEP> 86-87 <tb> Cl <tb> 60 <SEP> C2H5 <SEP> 3-[Cl-#-CH-O-CH2-] <SEP> NH <SEP> 58.55 <SEP> 5.16 <SEP> 3.41 <SEP> 58.91 <SEP> 5.23 <SEP> 3.29 <SEP> 011 <tb> CH3 <tb> O61 <SEP> C2H5 <SEP> 4-[#] <SEP> NH <SEP> 71.37 <SEP> 6.56 <SEP> 3.96 <SEP> 70.97 <SEP> 6.66 <SEP> 3.72 <SEP> 98-100 <tb> TABLE A (Cont Representative Malonic Acid Derivative Compounds EMI73.1 Substituents Elemental Analysis Melting Compound R'1 Z'1 Y'1 Calculated Found Point No. C H N C H N C 62 C2H5 3-C6H5O- NH 68.22 5.73 4.68 68.15 5.84 4.69 011 63 C2H5 2,5-Cl2-3-CO2CH3 NH 46.73 3.92 4.19 46.85 3.91 4.12 011 64 C2H5 2,3-(CH-CHCH-CH) NH 70.02 5.88 5.44 70.30 6.00 5.51 78-80 65 C2H5 H NH 63.76 6.32 6.76 63.44 6.54 7.03 011 66 C2H5 3,4-Cl2 NH 47.85 4.02 5.07 47.76 4.09 5.36 80-83 67 C2H5 4-CF3 NH 52.37 4.39 5.09 52.17 4.56 5.17 78-79.5 68 C2H5 4-NO2 NH 52.38 4.80 11.11 52.20 4.27 11.14 98-101 69 C2H5 4-Br NH 46.17 4.23 4.90 46.33 4.16 4.91 96-98 70 CH2CH2OCH3 2-CH3-4-Br NH 47.29 4.88 - 47.56 5.02 - 93-95 71 C2H5 2-CO2CH3-4-Br NH 45.37 4.10 4.07 45.61 4.07 4.29 99-100 72 C2H5 2-Br-4-CH3 NH 48.02 4.70 4.67 48.35 4.88 4.56 91-94 73 n-C4H9 4-C@N NH 64.60 6.20 10.76 64.13 6.29 10.94 50-53 74 C2H5 3,5-Cl2 S 45.06 3.44 - 44.81 3.68 - 011 75 C2H5 2-CH3-4-Br NH 48.02 4.70 4.67 48.10 4.85 4.71 114-116 76 C2H5 2-CH3-4-CH3O NH 62.14 6.83 5.57 61.47 6.78 5.30 109-110 Example III Preparation of ethyl l-(2-methyl-4,5-dichloro phenylaminocarbonyl)cyclopropanecarboxylate Into a nitrogen-purged round bottom flask was charged 5.53 grams (0.03 mole) of 2-methyl4,5-dichloroanlline, 3.18 grams (0.03 mole) of triethylamine and 190 milliliters of tetrahydrofuran solvent. With vigorous stirring, a 5.55 gram (0.03 mole) portion of ethyl l-chlorocarbonylcyclopropanecarboxylate prepared in Example XVIII was added in one portion, after which the mixture was stirred at ambient temperature for a six-hour period. A precipitate of triethylamine hydrochloride was then filtered off and the filtrate vacuum stripped to give a light yellow solid. The solid was taken up In ether and the solution water-washed, dried over magnesium sulfate, and solvent evaporated to give a yellow powder. Recrystallization from ethyl acetate-hexane gave 4.51 grams (0.01 mole) of ethyl l-(2-methyl-4,5-dlchlorophenylaminocarbonyl )cyclo- propanecarboxylate having a melting point of 105"C-107"C. Elemental analysis of the product Indicated the following: Analysis: C14H15Cl2NO3 Calculated: C, 53.18; H, 4.78; N, 4.43 Found: C, 53.41; H, 4.76; N, 4.44 This compound is referred to hereinafter as Compound 77. Example IV In a manner similar to that employed in Example III, other compounds were prepared. The structures and analytical data for Compounds 78 through 96 are set forth in Table B below. TABLE B Representative Malonic Acid Derivative Compounds EMI75.1 Substituents Elemental Analysis Melting Compound R'2 Z'2 Calculated Found Point No. C H N C H N C 78 C2H5 2,4,5-Cl3 46.38 3.59 4.16 46.69 3.99 4.10 130-132.5 79 C2H5 3,4-Cl2 51.67 4.34 4.64 51.95 4.34 4.72 107-110 80 C2H5 2,4-Cl2 51.67 4.34 4.64 51.27 4.53 4.46 95-98 81 C2H5 2,5-Cl2 51.67 4.34 4.64 51.36 4.48 4.49 105-108 82 C2H5 2-F-4-Cl 54.65 4.59 4.90 54.92 4.71 4.85 94.5-96 83 C2H5 4-Cl 58.32 5.27 5.23 58.15 5.29 5.16 91-93 84 C2H5 4-Br 50.02 4.52 4.49 50.18 4.69 4.52 92.5-95 85 C2H5 3,4-Br2 39.92 3.35 3.58 40.18 3.47 3.60 128-130 86 C2H5 3,5-Br2 39.92 3.35 3.58 39.82 3.32 3.46 91-92.5 87 C2H5 2,4-Br2 39.92 3.35 3.58 40.02 3.61 3.77 102-103.5 88 C2H5 2-Cl-4-Br 45.04 3.78 4.04 45.28 3.98 3.90 109-110.5 89 C2H5 2-Br-4-Cl 45.04 3.78 4.04 44.89 4.29 3.80 95-96 90 C2H5 3-Cl-4-Br 45.04 3.78 4.04 45.16 4.20 3.79 113-116 91 C2H5 2-CH3-4-Br-5-Cl 46.62 4.19 3.88 48.14 4.74 3.86 119-121 TABLE B (Cont.) Representative Malonic Acid Derivative Compounds EMI76.1 Substituents Elemental Analysts Melting Compound R'2 Z'2 Calculated Found Point No. C H H C H N C 92 C2H5 2-F-4-Br 47.29 3.97 4.24 46.87 4.07 4.02 102-103 93 C2H5 H 66.83 6.47 6.00 66.54 6.48 5.80 85-89 94 C2H5 3,5-Cl2 51.67 4.34 4.64 51.52 4.52 4.36 64-67 95 C2H5 4-C-N 65.10 5.46 10.85 65.02 5.51 10.67 129-132 96 C2H5 2-CH3-4-Br 51.55 4.94 4.29 51.72 4.74 4.31 89-91 Example V Preparation of 3-C(4-bromo-2-methylphenyl)- aminol-3-oxopropanoic acid A 6.0 gram (0.02 mole) portion of ethyl 3-[(4-bromo-2-methylphenyl)amino]-3-oxopropanoate prepared in Example I (Compound No. 75) was dissolved in approximately 80 milliliters of ethanol and 1.2 grams (0.03 mole) of sodium hydroxide pellets were added to the resulting mixture. The mixture was stirred for four hours and then allowed to stand overnight. The mixture was then evaporated to dryness and water added to give a yellow cloudy solution. This solution was extracted with methylene chloride and then acidified with 10% hydrochloric acid causing a white precipitate to form. The white precipitate was worked up to give 1.8 grams (0.01 mole) of 3-[(4-bromo-2-methylphenyl)amino]-3-oxopropanoic acid as a white solid having a melting point of 163"C-165"C. Elemental analysis of the product indicated the following: Analysis: C10H10BrN03 Calculated: C, 44.14; H, 3.70; N, 5.15 Found: C, 43.90; H, 3.68; N, 5.11 This compound is referred to hereinafter as Compound 97. Example VI In a manner similar to that employed in Example V, other compounds were prepared. Compound 108 was obtained from Research Services, P.O. Box 11212, Santa Ana, California 92711. Compound 109 was obtained from Dr. A.K. Mittal, 32/17 E. Patel Nagar, New Delhi 110 008, India. The structures and analytical data for Compounds 98 through 109 are set forth in Table C below. TABLE C Representative Malonic Acid Derivative Compounds EMI79.1 Substituents Elemental Analysis Melting Compound R'3 Z'3 Calculated Found Point No. C H N C H N C 98 H 4-Cl 50.60 3.77 6.56 50.67 3.80 6.37 140-141 99 H 2-CH3-4-Br-5-Cl 39.18 2.96 4.57 39.36 3.14 4.44 181-182 100 H 3,5-Br2 32.08 2.09 4.16 32.34 2.33 4.04 164-165.5 101 H 2-F-4-Br 39.15 2.56 5.07 39.24 2.42 4.94 161-162 102 H 2,4,5-Cl3 38.26 2.14 4.96 38.51 2.12 4.84 174-174.5 103 H 2-Br-4-CH3 NMR(COCl3/DMSO-d6): # 2.27(s, 3H), 3.4(s, 2H), 154-157 6.95-8.01 (m, 4H), 9.5-9.7 (br s, H)ppm. 104 H 2-Br-4-Cl 36.95 2.41 4.79 37.18 2.77 4.71 159-161 105 H 2-Cl-4-Br 36.95 2.41 4.79 37.10 2.60 4.76 165.5-167 106 H 2,4-Br2 32.08 2.09 4.16 32.27 2.23 4.13 157-159 107 H 3,4-Br2 32.08 2.09 4.16 31.96 2.22 4.08 14. 4 108 H 2,4-Cl2 NMR(CDCl3/DMSO-d6): # 2.49-2.64 (brs.H), 3.52 (s,2H), --7.17-8.24 (m, 3H), 9.86-10.05 (br s,H)ppm. 109 H 3-Cl-4-CH3 NMR(CDCl3/DMSO-d6): # 2.30 (s.3H). 2.45-2.63 (br s. H), 3.34 (s,2H), ---' 7.05-7.86 (m, 3H). 10.04-10.23 (br s.H)ppm. Example VII Preparation of l-(2-methyl-4,5-dichloro- phenelaminocarbonvl)ceclopropanecarboxylic acid A solution containing 0.34 gram (0.006 mole) of potassium hydroxide and 0.109 gram (0.006 mole) of water in 80 milliliters of ethanol was prepared in a 250 milliliter round bottom flask. With cooling to a temperature of 0 C in an ice/NaC1 bath and stirring, a solution of ethyl 1-(2-methyl-4,5-dichlorophenylaminocarbonyl)cyclopropanecarboxylate prepared in Example III in a small volume of ethanol was added and the mixture allowed to stir with warming to room temperature over a 72 hour period. The mixture was vacuum evaporated to give a white solid residue which was dissolved in water and extracted twice with ether. The ether extracts were discarded. The water solution was acidified to a pH of 2 with 25% HC1 solution causing separation of a solid which was taken up into ether, and the acidified aqueous phase was extracted four times. The combined ether extracts were dried over magnesium sulfate and vacuum evaporated to give a white solid. This white solid was water-washed and dried in a vacuum oven to give 1.85 grams (0.006 mole) of 1-(2-methyl-4,5dichlorophenylaminocarbonyl)cyclopropanecarboxylic acid having a melting point of 248"C-251"C. Elemental analysis of the product indicated the following: Analysis: 12 11 2 3 Calculated: C, 50.02; H, 3.85; N, 4.86 Found: C, 50.51; H, 4.31; N, 4.83 This compound is referred to hereinafter as Compound 110. Example VIII @ @ manner similar to that employed in Example @@@, other compounds were prepared. The structures and analytical data for Compounds 111 through 128 are set forth in Table D below. TABLE D Representative Malonic Acid Derivative Compounds EMI82.1 Substituent Elemental Analysis Melting Compd. Z'4 Calculated Found Point No. C H N C H N C 111 2-CH3-4-Br 48.34 4.06 4.70 48.20 4.06 4.66 204.5-206 112 2,4,5-Cl3 42.82 2.61 4.54 43.11 3.14 4.42 250 113 2,5-Cl2 48.20 3.31 -5.11 48.33 3.26 4.96 223.5-226 114 2,4-Cl2 48.20 3.31 5.11 45.26 3.40 5.03 189-190 115 2-F-4-Cl 51.27 3.52 5.44 51.18 3.70 5.22 202-204 116 4-Cl 55.12 4.27 5.84 54.69 4.35 5.59 217-219 117 4-Br 46.50 3.55 4.93 46.36 3.45 4.86 220-222 118 3,4-Br2 36.39 2.50 3.86 37.13 2.70 3.83 224-226.5 119 3,5-Br2 36.39 2.50 3.86 36.99 2.60 3.82 211-212 120 2.4-Br2 36.39 2.50 3.86 36.61 2.95 4.04 222-225 121 2-Cl-4-Br 41.47 2.85 4.40 39.74 3.90 3.95 166-168(dec.) 122 2-Br-4-Cl 41.47 2.85 4.40 41.67 3.28 3.91 210-211 123 3-Cl-4-Br 41.47 2.85 4.40 41.70 3.23 4.11 211-214 124 2-CH3-4-Br-5-Cl 43.33 3.33 4.21 45.47 4.08 3.91 231-234 125 2-F-4-Br 43.73 3.00 4.64 43.97 3.05 4.30 203.5-207 126 4-CF3 52.75 3.69 5.13 52.73 3.90 5.04 195-196.5 127 3,5-Cl2 NMR (CDCl3): 1.52 (s,4H), 7.02-7.74 (m,4H), 70.08 198-202 (s. H) ppm. 128 3,4-Cl2 48.20 3.31 5.11 48.79 3.80 5.26 220-222.5 Example IX PreparatNon of ethvl l-(4-bromo-2-methvlDhenyl- aminocarbonyl)cyclobutanecarboxylate Into a nitrogen-purged reaction flask was charged 2.74 grams (0.01 mole) of 4-bromo-2-methyl aniline and 1.49 grams (0.01 mole) of triethylamine dissolved in 200 milliliters of tetrahydrofuran. With vigorous stirring, 2.80 grams (0.01 mole) of ethyl 1 -chlorocarbonylcyclobutanecarboxylathe prepared in Example XIX were added and the resulting mixture stirred at ambient temperature for 6 hours, A precipitate of triethylamine hydrochloride was removed by filtration. The filtrate was vacuum stripped and the residue taken up in methylene chloride. This solution was washed successively with 2N HC7 (2 x 75 milliliters) and water, and then dried over magnesium sulfate. Rotary evaporation gave a crude product which was flash chromatographed on silica musing 7:3 hexane-ethyl acetate to give 3.68 grams (0.01 mole) of ethyl 1-(4-bromo-2-methyl- phenylaminocarbonyl)cyclobutanecarboxylate as a white solid. A small sample which was recrystallized from hexane had a melting point of 61 C-64 C. Elemental analysis of the product indicated the following: Analysis: C1 5Hl 8BrN03 Calculated: C, 52.92; H, 5.33; N, 4.12 Found: C, 52.99; H, 5.44; N, 4.05 This compound is referred to hereinafter as Compound 129. Example X In a manner similar to that employed in Example IX, other compounds were prepared. The structures and analytical data for Compounds 130 through 134 are set forth in Table E below. TABLE E Representative Malonic Acid Derivative Compounds EMI85.1 Substituents Elemental Analysis Melting Compd. R'4 Z'5 Calculated Found Point No. C H N C H N C 130 C2H5 3,5-Cl2 53.18 4.78 4.43 52.84 4.87 4.23 76.5-80 131 C2H5 2,4,5-Cl3 47.95 4.02 4.00 47.25 3.70 3.94 47-49 132 C2H5 2,4-Cl2 53.18 4.78 4.43 52.84 4.67 5.11 011 133 C2H5 3,4-Cl2 53.18 4.78 4.43 53.14 4.71 5.92 011 134(a) C2H5 4-Cl 59.68 5.73 -- 59.89 5.70 -- 85.5-87 (a) Prepared by the mixed anhydride procedure of Example XXXIII. Example XI Preparatfon of 1-(3,5-dichlorohenvl- aminocarbonyl)cyclobutanecarboxylic acid A 2.0 gram (0.006 mole) portion of ethyl1-(3,5-dichlorophenylaminocarbonyl)cyclobutanecarboxylate prepared in Example X (Compound 130) was hydrolyzed in the presence of water (0.114 gram, 0.006 mole) and ethanol potassium hydroxide (0.355 gram, 0.006 mole). The potassium salt of the acid was then acidified with 25% HCl solution and worked up in a manner similar to that described in Example VII to give 0.92 gram (0.003 mole) of l-(3,5-di- chlorophenylaminocarbonyl)cyclobutanecarboxylic acid as a beige-colored solid having a melting point of 159 C-160 C. Elemental analysis of the product indicated the following: Analysis : C12H11Cl2NO3 Calculated:- C, 50.02; H, 3.85; N, 4,86 Found: C, 50.20; H, 3.83; N, 4.84 This compound is referred to hereinafter as Compound 135. Example XII In a manner similar to that employed in Example XI, other compounds were prepared. The structures and analytical data for Compounds 136 through 139 are set forth in Table F below. TABLE F Representative Malonic Acid Derivative Compounds EMI87.1 Substituent Elemental Analysis Melting Compd. Z'6 Calculated Found Point No. C H N C H N C 136 2.4.5-Cl3 44.68 3.12 4.34 44.88 3.14 4.23 146-147 137 2,4-Cl2 50.02 3.85 -- 50.22 4.30 -- 129-132 138 3.4-Cl2 50.02 3.85 -- 50.22 4.70 -- 151-153 139 4-Cl 56.81 4.77 -- 56.99 4.94 -- 159-161 Example XIII Prenaration of ethyl 1-(4-bromo-2-methelPhenvl- aminocarbonyl)cyclopentanecarboxylate Ethyl l-chlorocarbonylcyclopentane- carboxylate (3.10 grams, O.Q2 mole) prepared in Example XX, 4-bromo-2-methylaniline (2.82 grams, 0.02 mole) and triethylamine (1.53 grams, 0.02 mole) were reacted in tetrahydrofuran (200 milliliters) under conditions similar to those described in Example I to give 2.40 grams (0.007 mole) of ethyl l-(4-bromo-2-methylphenylaminocarbonyl)cyclopentanecarboxylate which, after recrystallization from hexane, had a melting point of 64 C-67 C. Elemental analysis of the product indicated the following: Analysis: C16H20BrN03 Calculated: C, 54.25; H, 5.69; N, 3.95 Found: C, 54.05; H, 5.55; N, 3.81 This compound is referred to hereinafter as Compound 140. Example XIV Preparation of ethyl 2-(4-bromo-2 methylphenylaminocarbonyl)butanoate Ethyl 2-(chlorocarbonyl)butanoate (5.8 grams, 0.03 mole), 4-bromo-2-methylanillne (5.0 grams, 0,03 mole) and triethylamine (3.27 grams, 0.03 mole) were reacted under conditions similar to that described for Example I to give 7.4 grams (0.02 mole) of ethyl 2-(4-bromu-2-methylphenylamino- carbonyl)butanoate as a white solid having a melting point of 98 C-100 C. Elemental analysis of the product indicated the following: Analysis: C14H18BrNO3 Calculated: C, 51.23; H, 5.53; N, 4.27 Found: C, 51.40; H, 5.63; N, 4.25 This compound is referred to hereinafter as Compound 141. Example XV In a manner similar to that employed in Example XIV, other compounds were prepared. The structures and analytical data for Compounds 142 through 152 are set forth in Table G below. Table G Representative Malonic Acid Derivative Compounds EMI90.1 Substituents Elemental Analysis Melting Compound Y'2 Y'3 R'5 Z'7 Calculated Found Point No. C H N C H N C 142 C6H5 H C2H5 2-CH3-4-Br 57.46 4.82 3.72 57.39 4.78 3.95 115-117 143 C6H5 H C2H5 2,3-(CH-CHCH-CH)- 75.66 5.74 4.20 75.60 6.02 4.11 115-117 144 Br CH3 C2H5 2-CH3-4-Br 39.72 3.85 3.56 40.13 3.68 3.62 011 145 Br CH3 C2H5 4-Cl 43.07 3.92 4.19 43.24 4.29 3.99 011 146 Br CH3 C2H5 3,4-Cl2 39.05 3.28 - 39.58 3.74 - 011 147 Br CH3 C2H5 2,4-Cl2 39.05 3.28 3.80 39.56 3.54 3.88 011 148 Br CH3 C2H5 3,5-Cl2 39.05 3.28 3.80 39.80 3.53 3.86 011 149 CH3 CH3 C2H5 2-CH3-4-Br 51.23 5.53 4.27 51.49 5.55 4.17 011 150 C2H5 C2H5 C2H5 2-CH3-4-Br 53.94 6.23 3.93 53.89 6.36 3.52 011 151 CH3 H C2H5 2-CH3-4-Br 49.70 5.13 4.46 49.59 5.18 4.41 117-118 152 Br CH3 C2H5 4-C@N 48.02 4.03 8.62 48.17 4.53 8.74 011 Example XVI PreparatGon of 3-r(4-bromo-2-methvlPhenyl )- aminol-2-bromo-2-methyl-3-oxopropanoic acid A 1.25 gram (0.003 mole) portion of ethyl 3-t(4-bromo-2-methylphenyl)amino]-2-bromo-2-methyl-3- oxopropanoate prepared in Example XV (Compound 144) was hydrolyzed with water (0.06 gram, 0.003 mole) and ethanol potassium hydroxide (0.21 gram, 0.003 mole). The potassium salt of the acid was then acidified with concentrated HC1 and worked up in a manner similar to that described in Example VII to give 1.04 grams (0.003 mole) of 3-((4-bromo- 2-methylphenyl)amino]-2-bromo-2-methyl-3-oxopropanoic acid as a white solid having a melting point of 133 C-136 C. NMR analysis of the product indicated the following: NMR (CDC13-DMSO d6): # 2.05 (s, 3H), 2.20 (s, 3H), 2.4-2.6 (br s, H), 7.2-7.53 (m, 3H), 9.6-9.8 (br s, H) ppm. This compound is referred to hereinafter as Compound 153. Example XVII PreDaratNon of N-butvl 3-F(4-bromo-2- methylphenyl)amino]-3-oxopropanamide A mixture of 4.90 grams (0O2 mole) of ethyl 3-[(4-bromo-2-methylphenyl)amino]-3oxopropanoate prepared in Example I (Compound No. 75), 358 grams (4.9 moles) of n-butylamine , 150 milliliters of ethanol and 5 drops of water wa's stirred at room temperature for about 16 hours. After this period, rotary evaporatlon gave a crude product as a white solid. The white solid was recrystallized from ethyl acetate-hexane to g; 3.08 grams (0.009 mole) of N-butyl 3-[(4-bromo-2-methylphenyl)amino]-3- oxopropanamide having a melting point of 123 C-125 C. Elemental analysis of the product indicated the following: Analysis: C14H19BrN2O2 Calculated: C, 51.38; H, 5.85; N, 8.56 Found: C, 51.42; H, 5.91; N, 8.69 This compound is referred to hereinafter as Compound 154. Example XVIII Preparation of ethvl l-chlorocarbonvl- cYcloDroPanecarboxYlate Into a stirred solution containing 15.1 grams (0.27 mole) of potassium hydroxide in 240 milliliters of ethanol and 4.83 grams (0.27 mole) of water was added dropwise, with cooling at a temperature of 0 C, 50.0 grams (0.27 mole) of diethyl l,1-cyclopropanedicarboxylate The mixture was stirred for about 16 hours at room temperature. Solvent was removed under reduced pressure to give a white residue which was dissolved in water and extracted with ether. The water solution was acidified to a pH of 2 with 25% aqueous hydrochloric acid and the organic acid was extracted from the aqueous suspension with ethyl ether (4 x 400 milliliters). The ether extract was dried over magnesium sulfate and vacuum stripped to give the monocarboxylic acid as a clear liquid. The clear liquid was dissolved in 300 milliliters of methylene chloride after which 74 grams (0.62 mole) of thionyl chloride were added, and the resulting mixture was then heated under reflux for approximately 16 hours. Volatiles were removed, under reduced pressure to give 45.7 grams (0.25 mole) of ethyl l-chlorocarbonylcyclopropanecarboxylate. NMR analysis of the product indicated the following: NMR (CDCl3): $ 1.22-1.50 (t, 3H), 1.75 (s, 4H), 4.1-4.52 (q, 2H) ppm. This compound is referred to hereinafter as Compound 155. Example XIX Preparation of ethvl l-chlorocarbonvlcvclo- butanecarboxylate Diethyl 1,1-cyclobutanedicarboxylate (20.0 grams, 0.10 mole) was saponified with 6.59 grams (0.10 mole) of potassium hydroxide in a mixture of 200 milliliters of ethanol and 1.80 grams (0.10 mole) of water and worked up to give the monocarboxylic acid which was reacted with thionyl chloride (8.86 grams, 0.07 mole) in methylene chloride solution as'described in Example XVIII. Removal of the solvent gave 7.48 grams (0.04 mole) of ethyl l-chlorocarbonylcyclobutanecarboxylathe. NMR analysis of the product indicated the following: NMR (CDCl ) # 1.10-1.44 (t, 3H), 1.7-2.85 (m, 6H), 4.05-4.5 (q, 2H) ppm. This compound is referred to hereinafter as Compound 156. Example XX Prenaration of ethyl l-chlorocarbonvl cyclopentanecarboxylate In a manner similar to the procedure described in Example XVIII, with the exception that reflexing with thionyl chloride in methylene chloride was conducted for only a 2 hour period, a 10 gram (0.05 mole) portion of diethyl 1,1-cyclo- pentanedicarboxylate was converted into 5.67 grams (0.03 mole) of ethyl l-chlorocarbonylcyclopentanecarboxylate. NMR analysis of the product indicated the following: NMR (CDCl3):# 1.10-1.49 (t, 3H), 1.56-2.48 (m, 8H), 4.0-4.5 (q, 2H) ppm. This compound is referred to hereinafter as Compound 157. Example XXI Preparation of ethvl 2-bromo-2-chloro carbonylpropanoate In a manner similar to the procedure described in Example XVIII, except that refluxing with thionyl chloride in methylene chloride solution was conducted only for a 6 hour period followed by standing at room temperature for about 16 hours, a 25.0 gram (0.10 mole) portion of diethyl 2-bromo-2-methylmalonate was converted into 12.94 grams (0.05 mole) of ethyl 2-bromo-2-chlorocarbonylpropanoate. This compound was employed in the Preparation of Compound Nos 144-148 and 152 in Example XV. NMR analysis of the product indicated the following: NMR (CDC13): # 1.10-1.47 (t, 3H), 2.05-2.17 (s pair, 3H), 4.05-4.55 (q pair, 2H) ppm. This compound is referred to hereinafter as Compound 158. Example XXII Preparation of ethvl 3-F(4-chloroDhenvlBaminol-3- oxopropanoate 4-Chloroaniline (25.4 grams, 0.20 mole) and diethyl malonate (48 grams; 0.30 mol-e) were reacted in a manner similar to the procedure described by A.K. Sen and P. Sengupta, Jour, Indian Chem. Soc. 46 (9), 857-859 (1969). The reaction afforded a greenish colored solid which was recrystallized from toluene-hexane (1:1) and then from isopropyl ether to give 9.0 grams (0.04 mole) of ethyl 3-[(4-chloro phenyl)amlno]-3-oxopropanoate as white crystals having a melting point of 82 C-83 C. Elemental analysis of the product indicated the following: Analysis: C11H12ClNO3 Calculated: C, 54.67; H, 5.01; N, 5.80 Found: C, 54.90; H, 4.94; N, 6.07 This compound is referred to hereinafter as Compound 159. Example XXIII Preparation of ethvl 3-F(4-methvithiazol-2-vl) aminol-3-oxopropanoate In a manner similar to the procedure described in Example I, 2-amino-4-methylthiazole was reacted with ethyl malonyl chloride employing triethylamine as the acid acceptor in etrahydrofuran solution. The ethyl -[(4-methylthiazo]-2-yl)amino]-3-oxopropanoate product (7.5 grams, 0.03 mole) was obtained as an off-white solid having a melting point of 138 C-141 C. Elemental analysis of the product indicated the following: C9H12N2O3S Calculated: C, 47.36; H, 5.30; N, 12.27 Found: C, 47.50; H, 4.62; N, 11.77 This compound is referred to hereinafter as Compound 160. Example XXIV In a manner similar to that employed in xample XXIII, other compounds were prepared. nd 173 was obtained from Clarkson College of Technology, Potsdam, New York. The structures and analytical data for compounds 161 through 173 are set forth in Table H below. TABLE H Representative Malonic Acid Derivative Compounds EMI97.1 EMI97.2 Elemental <SEP> Analysis <SEP> Melting <tb> Compound <SEP> R'4 <SEP> Calculated <SEP> Found <SEP> Point <tb> No. <SEP> C <SEP> H <SEP> N <SEP> C <SEP> H <SEP> N <SEP> C <tb> 161 <SEP> # <SEP> 48.25 <SEP> 3.71 <SEP> 9.38 <SEP> 48.48 <SEP> 3.29 <SEP> 9.24 <SEP> 155-157 <tb> 162 <SEP> # <SEP> 57.92 <SEP> 4.86 <SEP> 9.65 <SEP> 58.08 <SEP> 4.63 <SEP> 9.62 <SEP> 164-168 <tb> 163 <SEP> # <SEP> 42.00 <SEP> 3.23 <SEP> 8.16 <SEP> 41.75 <SEP> 2.20 <SEP> 7.92 <SEP> 210 <SEP> (dec.) <tb> 164 <SEP> # <SEP> 50.94 <SEP> 5.70 <SEP> 13.20 <SEP> 51.13 <SEP> 5.69 <SEP> 13.17 <SEP> 63-65 <tb> TABLE H (Cont.) Representative Malonic Acid Derivative Compounds EMI98.1 EMI98.2 Elemental <SEP> Analysis <SEP> Melting <tb> Compound <SEP> R'6 <SEP> Calculated <SEP> Found <SEP> Point <tb> No. <SEP> C <SEP> H <SEP> N <SEP> C <SEP> H <SEP> N <SEP> C <tb> 165 <SEP> # <SEP> 50.94 <SEP> 5.70 <SEP> 13.20 <SEP> 50.63 <SEP> 5.15 <SEP> 13.32 <SEP> 127-129 <tb> 166 <SEP> # <SEP> 47.36 <SEP> 5.30 <SEP> 12.27 <SEP> 47.41 <SEP> 5.46 <SEP> 11.76 <SEP> 90-92 <tb> 167 <SEP> # <SEP> 32.78 <SEP> 3.09 <SEP> 9.56 <SEP> 32.76 <SEP> 2.34 <SEP> 9.62 <SEP> 163-165 <tb> 168 <SEP> # <SEP> 44.43 <SEP> 5.38 <SEP> 17.27 <SEP> 44.13 <SEP> 5.41 <SEP> 17.41 <SEP> 148-150 <tb> 169 <SEP> # <SEP> 49.50 <SEP> 4.57 <SEP> 11.54 <SEP> 49.30 <SEP> 4.@@ <SEP> 11.@4 <SEP> 65-68 <tb> TABLE H (Cont.) Representative Malonic Derivative Compounds EMI99.1 EMI99.2 Elemental <SEP> Analysis <SEP> Melting <tb> Compound <SEP> R'6 <SEP> Calculated <SEP> Found <SEP> Point <tb> No. <SEP> C <SEP> H <SEP> N <SEP> C <SEP> H <SEP> N <SEP> C <tb> 170 <SEP> # <SEP> 49.50 <SEP> 4.57 <SEP> 11.54 <SEP> 49.34 <SEP> 4.64 <SEP> 11.69 <SEP> 99-100 <tb> 171 <SEP> # <SEP> 46.61 <SEP> 4.10 <SEP> 16.31 <SEP> 49.88 <SEP> 4.83 <SEP> 16.24 <SEP> 132-136 <tb> 172 <SEP> # <SEP> 52.85 <SEP> 5.76 <SEP> 6.16 <SEP> 53.01 <SEP> 5.81 <SEP> 6.11 <SEP> 011 <tb> 173 <SEP> # <SEP> NMR(CDCl3): <SEP> # <SEP> 1.11-1.45 <SEP> (t, <SEP> 3H), <SEP> 2.20 <SEP> (s, <SEP> 3H), <SEP> 2.36 <SEP> (s,3H). <SEP> 109-129 <tb> 3.46 <SEP> (s,2H), <SEP> 4.03-4.48 <SEP> (q,2H), <SEP> 6.76 <SEP> (s,H), <SEP> 7.83 <SEP> (s,H), <tb> 9.06-9.51 <SEP> (br <SEP> s.H)ppm. <tb> Example XXV Preparation of ethvl 2-chlorocarbonvl-3 methvl-2-butenoate Methyl isopropylidenemalonate (30 grams, 0.15 mole) was saponified with 10.0 grams (O.1S mole) of potassium hydroxide in 200 milliliters of ethanol solution and worked up to give the monocarboxylic acid which was then reacted with thionyl chloride (10 milliliters, 0.1 mole) Rn methylene chloride solution in a manner similar to the procedure described in Example XVIII. Removal of solvent gave 9.6 grams (0.05 mole) of ethyl 2-chlorocarbonyl-3- methyl-2-butenoate. NMR analysis of the residue product in COCl3 solution indicated complete conversion of the carboxylic acid to the acid chloride as evidenced by absence of a downfield carboxylic acid proton. This compound is referred to hereinafter-as Compound 174. Example XXVI Preparation of ethvl 2-F(4-bromo-2-methvlphenvl)- aminocarbonyll-3-methyl-2-butenoate In a manner similar to the procedure described in Example I, ethyl 2-chlorocarbonyl 3-methyl-2-butenoate (9.6 grams, 0.05 mole) prepared in Example XXV, 4-bromo-2-methylaniline (5.3 grams, 0.03 mole) and triethylamine (4.0 milliliters, 0.03 mole) were reacted to give 2.9 grams (0.009 mole) of ethyl 2-((4-bromo- 2-methylphenyl)-aminocarbonyl]-3- methyl-2-butenoate as a white solid having a melting point of 116 C-119 C. NMR analysis of the product indicated the following: NMR(CDC13): # 1.17-1.43 (t,3H), 2.10-2.19 (d,6H), 2.28 (s,3H), 4.08-4.50 (q,2H), 7.21-8.20 (m,4H) ppm. This compound is referred to hereinafter as Compound 175. Example XXVI I Preparation of 3,4-dichlorp-2,5-dimethylaniline A solution of 5.0 grams (0.03 mole) of 3,4-dichloro-2,5-dimethyl-1-nitrobenzene in 70 pilliliters of ethanol was hydrogenated at room temperature at 50 psi in the presence of 0.25 gram of 10% palladium on activated carbon as a catalyst. Working up the reaction mixture gave 1.21 grams (0.006 mole) of 3,4-dichloro-2,5-dimethylaniline as yellow solid having a melting point of 72 C-76 C. WR analysis of the product indicated the following: NMR(CDC13): 6 2.24 (s,3H), 2.32 (s,3H), 3.60 (br s,2H), 6.50 (s,H) ppm. This compound is referred to hereinafter as Compound 176. Example XXVIII Preparation of 4,5-dichloro-2-methoxyaniline Part A: Preparation of 2.2-dimethvl-N-(4-chloro- 2-methoxyphenyl)propanamide Into.a stirred solution containing 10.0 grams (0.06 mole) of 4-chloro-2-methoxyaniline and 6.42 grams (0.06 mole) of triethylamine in 200 milliliters of tetrahydrofuran was added 7.65 grams (0.06 mole) of trimethylacetyl chloride in a small amount of tetrahydrofuran solvent. The resulting mixture was stirred for two hours at room temperature. Triethylamine hydrochloride precipitated and was filtered off and the filtrate vacuum stripped to give a dark liquid which was taken up in methylene chloride. This solution was washed with 2N HC1 (2 x 100 milliliters), then with water (1 x 100 milliliters), dried over magnesium sulfate and solvent evaporated to give a crude product which was crystallized from hexane to give 6.82 grams (0.03 mole) of 2,2-dimethyl-N-(4-chloro 2-methoxyphenyl)propanamlde as a first and second crop. NMR analysis of the product indicated the following: NMR (CDCl3):# 1.32 (s, 9H) 3.91 (s, 3H), 6.83-7.08 (m, 2H), 8.28-8.52 (d, 2H) ppm. Part B: PreDaration of 2,2-dimethvl-N- (4,5-dichloro-2-methaxyghenyl)oropanamld Into a stirred solution containing 6.82 grams (0.03 mole) of 2,2-dimethyl-N-(4-chloro-2methoxyphenyl)propanamide prepared in Part A in 150 milliliters of chloroform was added 3.81 grams (0.03 mole) of sulfuryl chloride over a 40 minute period. The resulting reaction mixture was heated under reflux for a 3 day period, each day cooling the mixture and adding an additional 3.81 grams (0.03 mole) of sulfuryl chloride before continuing the reflux. At the end of 3 days, thin layer chromatographic analysis of the mixture indicated the reaction to be complete. Volatiles were removed from the reaction mixture and 3.70 grams (0.01 mole) of 2,2-dimethyl-N-(4,5-dichloro-2-methoxyphenyl)- propanamlde recovered as a light yellow-orange solid by flash column chromatography eluting with dichloromethane. NMR analysis of this product indicate the following: NMR (CDC13): # 1.34 (s, 9H), 3.92 (s, 3H), 6.94 (s, H), 8.08 (br s H), 8.67 (s, H) ppm. Part C: Preparation of 4.5-dichloro-2 methoxyaniline The 2,2-dimethyl-N-(4,5-dichloro-2-methoxy phenyl)propanamide (3.70 grams, 0.01 mole) prepared in Part B was dissolved in ethanol: 12N HC1 (1:1), the mixture heated under reflux overnight and then freed of volatiles under rotary evaporatlon. Partition between 2N HC1 and dichloromethane gave an acid-soluble fraction which.was worked up to give 1.1 grams (0.01 mole) of pure 4,5-dichloro-2methoxyaniline as determined by thin layer chromatographic analysis. The dichloromethane fraction from above was freed of solvent giving starting material which was agaln refluxed overnight with ethanol: 12N HC1 and worked up to give an additional 1.2 grams (0.01 mole) of pure 4,5-dichloro-2-methoxyaniline as determined by thin layer chromatographic analysis. NMR analysis of the product indicated the following: NMR (CDCl3):# 3.88 (s, 5H), 6.73-6.90 (d, 2H) ppm. This compound is referred to hereinafter as Compound 177. Example XXIX Preparation of t-(4-bromo-2-methvlphenvlamino- carbonvl)cvclobutanecarboxvlic acid A 3.0 gram (0.009 mole) portion of ethyl 1-(4-bromo-2-methylphenylaminocarbonyl)cyclobutanecarboxylate prepared in Example IX (Compound 129) was hydrolyzed in a manner similar to that described in Example XI to give 2.19 grams (0.007 mole) of 1-(4-bromo-2-methylphenylaminocarbonyl)cyclobutanecarboxylic acid, Compound 181, having a melting point of 154 C-155 C. Example XXX Preparation of ethvl (chlorocarbonvl)methoxvacetate Part A. Preparation of diethvl methoxymalonate A mixture of 50.4 grams (0.3 mole) of dimethyl methoxymalonate, para-toluenesulfonic acid (2.76 grams) and 300 milliliters of ethanol was heated under reflux for a period of about 24 hours. Volatile materlals were then removed under reduced pressure, employing a water bath at about 25 C. A second 300 milliliter-portion of ethanol was added and the mixture then refluxed for about 5 hours after which it was stirred at room temperature for an approximate 64-hour period. Removal of ethanol from the mixture under reduced pressure gave 61.0 grams (0.3 mole) of dlethyl methoxymalonate, employed in the subsequent steps without purification. Part B. Preparation of mono-ethvl methoxvmalonate A mixture of 30.0 grams (0.2 mole) of diethyl methoxymalonate (Part A, above), 8.85 grams (0.2 mole) of potassium hydroxide, 2.84 grams (0.2 mole) of water and 300 milliliters of ethanol was stirred at room temperature for about 72 hours and volatiles then removed under reduced pressure. The residue was dissolved in water and the pH of the solution adjusted to 10 by addition of potassium hydroxide. The solution was saturated with potassium chloride and extracted with methylene chloride (3xi00 milliliters) to remove unsaponified blester. Acidification to pH=1 and continuous extraction with methylene chloride afforded 9.45 grams (0.06 mole) of mono-ethyl methoxymalonate as a liquid. Part C. Preparation of ethvl (chlorocarbonvl) methoxvacetate A mixture of 5.88 grams (0.04 mole) of mono-ethyl methoxymalonate from Part B, above, 8.63 grams (0.07 mole) of thionyl chloride and 150 milliliters of methylene chloride was stirred for about 17 hours and then evaporated free of volatile materials. As NMR examination indicated the reaction to be incomplete, the above thionyl chloride treatment in methylene chloride was repeated for a period of about 65 hours. A third treatment with 8.63 grams of thionyl chloride in 150 milliliters of methylene chloride was finally given, refluxing for a period of approximately 7 hours. Removal of volatiles under reduced pressure gave 6.0 grams (0.03 mole) of ethyl (chlorocarbonyl) methoxyacetate, Compound 211. NMR analysis of the product indicated the following: 'H NMR (CDCl3) # 1.16-1.53(t, 3H, CH3), 3.58(s, 3H, CH30), 4.13-4.56 (q, 2H, CH2) 4.62 (s, H, CH) ppm. Example XXXI Preparatlon of ethvl 3-[3.5-dichlorophenyl)aminol- -2-methoxv-3-oxoproDanoate 3,5-Dichloroaniline (2.69 grams, 0.02 mole) and ethyl (chlorocarbonyl)methoxyacetate (3.0 grams, 0.02 mole), prepared in Example LIII (Compound 211), were reacted in the presence of triethylamine (1.68 grams, 0.02 mole) in 200 milliliters of methylene chloride in a manner similar to that described in Example I to give 1.34 grams (0.004 mole) of ethyl 3[(3,5-dichlorophenyl)amino]-2-methoxy-3-oxopropanoate, Compound 213, having a melting point of 89.5 C-92.5 C. Example XXXII Prenaratlon of mono-methyl methoxvmalonate Dimethyl methoxymalonate (50.0 grams, 0.3 mole) was saponified with potassium hydroxide (17.3 grams, 0.3 mole) in a mixture of 500 milliliters of methanol and 5.55 grams (0.3 mole) of water according to the general procedure of Example VII but employing a reaction period of approximately 16 hours. The reaction mixture was evaporated free of solvents and the residue dissolved in water and extracted twice with ether to remove any unreacted blester. The aqueous layer was then saturated with potassium chloride, acidified with 2H HC1 and extracted twice with ethyl ether. As this procedure enabled recovery of only a minor amount of product the aqueous phase was then subjected to three 16-hour periods of continuous liquid-liquid extractlon with methylene chloride, adjusting the pH from 4 to 1 at the beginning of the second extraction period. Workup of the combined extracts gave 29.24 grams (0.2 mole) of mono-methyl methoxymalonate, Compound 214. NMR analysis of the product indicated the following: H NMR (COC13) J 3.54(s, 3H, alpha CH30), 3.86(s, 3H, ester CH30), 4.51 (s, H, CH), 9.36(s, H, C02H) ppm. Example XXXIII Prenaration of methvl 3-r(4-bromo-2-fluoro phenyl)aminol-2-methyoxy-3-oxopropanoate To a stirred mixture of 2.78 grams (0.02 mole) of mono-methyl methoxymalonate prepared in Example LVI (Compound 214) and 3.56 grams (0.02 mole) of 4-bromo-2-fluoroaniline in approximately 100 milliliters of dry tetrahydrofuran was fed dropwise a solution of 3.87 grams (0.02 mole) of 1,3-dicyclohexylcarbodiimide in about 30 milliliters of dry tetrahydrofuran, while cooling the reaction mixture in an Nce-water bath. The reaction mixture was allowed to warm slowly to room temperature and stirring continued for an approximate 65-hour period. The precipitated 1,3-dicyclohexylurea by-product (3.15 grams) was removed by filtration and the filtrate vacuum evaporated and the residue dissolved in methylene chloride. The latter solution was extracted with dilute HC1 and then water, then dried (MgSO4) and solvent vacuum evaporated to give a colorless liquid. Flash column chromatography of the latter on silica, eluding with hexane-ethyl acetate (7:3) gave, after workup, a liquid which crystallized on standing. Recrystallization from hexane containing a small amount of ethyl acetate gave 2.3 grams (0.01 mole) of methyl 3-[(4-bromo-2-fluorophenyl)amlno}- -2-methoxy-3-oxopropanaote, Compound 215, having a melting point of 51 C-53 C. Example XXXIV In a manner similar to that employed in Example XXXIII, other compounds were prepared. The structures and analytical data for Compounds 216 through 219 are set forth in Table I below. Insert Table I TABLE I Representative Malonic Acid Derivative Compounds EMI109.1 Elemental Analysis Melting Compound Substituent Calculated Found Point No. Z'10 C H N C H N C 216 3.4-Cl2 45.23 3.45 4.80 45.21 3.91 4.20 78-81 217 4-CF3 49.49 4.15 4.81 49.88 4.29 4.91 101-103 218 4-Br 43.73 4.00 -- 43.73 4.04 -- 55-59 219 3,4,5-Cl3 40.46 3.09 -- 40.44 3.22 -- 117-121 Example XXXV Preparation of t-butvl 3-[(3,5-dichlorophenyl)aminol -2-methoxv-3-oxopropanoate Part A Preiiaration of t-butvl methyl methoxymalonate To a stirred solution of 9.26 grams (0.06 mole) of methyl (chlorocarbonyl)methoxyacetate in 25 milliliters of carbon tetrachloride was added a mixture of 4.94 grams (0.07 mole) of anhydrous t-butyl alcohol, 4.50 milliliters (0.06 mole) of pyridine and 25 milliliters of carbon tetrachloride over an approximate 20-minute period, with cooling to 0 C-5 C by an ice bath. On completing the addition, the cooling bath was removed and the mixture allowed to stlr for a 4-hour period at ambient temperature after which pyridine hydrochloride was removed from the mixture by filtration. The filtrate was diluted with 100 milliliters of methylene chloride and partitioned with 100 milliliters of saturated aqueous sodium blcarbonate following which the organic phase was extracted with cold 10% hydrochloric acid (3 x 100 milliliters), then with cold water (3 x 100 milliliters) after which it was dried (MgSO4) and solvents then flash evaporated. The residue was vacuum distilled to give 7.57 grams (0.04 mole) of t-butyl methyl methoxymalonate having a boiling point of 93.5 C-95 C at 4.0 mm Hg. Part B Prenaration of mono-t-butvl methoxymalonate t-Butyl methyl methoxymalonate (7.57 grams, 0.04 mole), prepared in Part A, was saponified with potassium hydroxide (2.45 g, 0.04 mole) in a mixture of 25 milliliters of methanol and 668 microliters (0.04 mole) of water according to the general procedure of Example VII but employing a reaction period of 20 hours. Workup according to the general method of Example VII gave 5.42 grams (0.03 mole) of mono-t-butyl methoxymalonate. NMR analysis of the product indicated the following: H NMR (COCl3) # 1.45(s.9H, t-butyl), 3.58(s, 3H, CH30), 4.45(s, H, CH), 10.51(s, H, C02H) ppm. Part C Peparation of t-butvl 3-F(3,5-dichloro- phenyl)aminol-2-methoxy-3-oxopropanoate Mono-t-butyl methoxymalonate (5.42 grams, 0.03 mole), prepared in Part B, 3,5-dichloroaniline (4.62 grams, 0.03 mole) and 1,3-dicyclohexylcarbodiimide (5.88 grams, 0.03 mole) were reacted in a manner similar to that described in Example LVII to give 2.92 grams (0.009 mole) of t-butyl 3-[(3,5-dichlorophenyl)amino]-2-methoxy-3-oxopropanoate having a melting point of 129.5 C-131.5 C. Example XXXVI Preparation of methyl 3-[(3,5-dichlorophenyl)aminol- -2-methoxY-3-thioxopropanoate A mixture of 3.50 grams (0.01 mole) of methyl 3-[3,5-dichlorophenyl)amino]-2-methoxy3-oxopropanoate (Compound 233, Example LXX), 2.42 grams (0.006 mole) of 2,4-bis(4-methoxyphenyl)-1,3- dithia-2,4-diphosphetane-2,4-disulfide and 35 milliliters of anhydrous l,l-dimethoxyethane was stirred at room temperature for a period of about 20 hours after which stirring was continued with testlng at 55 C for a 168-hour interval. Solvent was removed from the reaction mixture under reduced pressure and the residue worked up by flash column chromatography to give 2.31 grams (0.007 mole) of methyl 3-[(3,5-dichloro-phenyl)aminol]-2-methoxy 3-thioxopropanoate, Compound 238, having a melting point of 144 C-147 C. Example XXXVII Preparation of 2-cyclopropenyl-1-carboethoxy-1-[N (2-methyl-4-bromophenyl)]carboxamide Part A. Preparation of diethyl bis(2,3-trimethyl silyl)cyclopropene-1,1-dicarboxylate A 50 milliliter round-bottom flask was equipped with a magnetic stirring bar and a reflux condenser with N2 inlet. The flask was charged with 183.0 grams (1.07 mole) of bis(trimethylsilyl) acetylene and 0.40 gram (0.0015 mole) of cupric acetylacetonate. Using an oil bath the temperature of the stirred mixture was raised to 145 C. Using a syringe pump 39.3 grams (0.21 mole) of diethyl diazomalonate were added over 36 hours, Heating at 1450C was continued for an additional 12 hours after all of the diazomalonate had been added. The excess bis(trimethylsilyl)acetylene was removed by vacuum distillation. The residue product was purified by flash chromatography eluding with 80:20 hexane-ethyl acetate to give 17.0 grams (0.05 mole) of diethyl bis(2,3-trimethylsilyl)cyclopropene 1,1-dicarboxylate as a yellow liquid. NMR analysis of the product indicated the following 'H NMR (CDC13): ct 0.23(s,18H), 1.20 (t, 6H),4.17(q, 4H) ppm. Part B. PreDaration of diethvl cvclonropene-l.l- dicarboxylate A 500 milliliter round-bottom flask was equipped with a magnetic stirrer and N2 inlet. The flask was charged with 21.0 grams (0.07 mole) of diethyl bis (2,3-trimethylsilyl)cyclopropene-1,1dicarboxylate. 125 milliters of acetonitrile, 12.2 grams (0.21 mole) of anhydrous KF, and 6.50 grams (0.02 mole) of dicyclohexano-lB-crown-6 ether. The mixture was stirred 6 hours at room temperature. The mixture was filtered and the filtrate concentrated under reduced pressure to a deep red oil. This oil was taken up in 100 milliliters of methanol and stirred 24 hours at room temperature. The methanol was removed under vacuum and the residue purified by flash column chromatography to give 6.25 grams (0.02 mole) of diethyl cyclo propene-l,l-dicarboxylate as a yellow oil. NMR analysis of the product indicated the following: 'H NMR (CDC13): 1.25 (t, 6H), 4.23 (q, 4H); 7.08 (s, 2H). Part C. Preparation of mono-ethyl cyclopropene-1,1 dicarboxvlate A 250 milliliter round-bottom flask was equipped with a magnetic stirring bar and an addition funnel with N2 inlet. The flask was charged with 6.15 grams (0.03 mole) of diethyl cyclopropene-l,l-dicarboxylate and 50 milliliters of ethanol. The stirred mixture was cooled in an ice bath and a solution of 1.33 grams (0.03 mole) of NaOH in 5.0 milliliters of water was added dropwise. The mixture was allowed to come to room temperature and stirred for 3 days. The reaction mixture was concentrated to 1/4 of the original volume under reduced pressure, diluted with ice water, and extracted twice with ether. The basic aqueous phase was acidified with ice cold 10% HC1, and extracted-three times with ethyl acetate. The ethyl acetate was dried (MgS04) and the solvent removed under reduced pressure to leave an orange colored solid. This was recrystallized from hexaneethyl acetate to give 3.65 grams (0.02 mole) of monoethyl cyclopropene-1,1-dicarboxylat as a light yellow solid having a melting point of 76.00C-77.50C. NMR analysis of the product indicated the following: 'H NMR (CDC13): J 1.20 (t, 3H), 4.25 (q, 2H), 6.80 (s, 2H), 11.5 (br s, lH) ppm. Part D. Preparation of l-carboethoxy-l-ethoxy carbonyloxycarbonyl-2-cyclopropene A 250 milliliter round-bottom flask was equipped with a magnetic stirred and an addition funnel with N2 inlet. The flask was charged with 1.30 grams (0.008 mole) of mono-ethyl cyclopropene1,1-dicarboxyiate. 50 milliliters of dry THF, 2.3 grams (0.02 mole) of potassium carbonate (anhydrous), and 450 milligrams of dicyclohexano-18crown-6 ether. The stirred reaction mixture was cooled to OOC, and 0.90 gram (0.008 mole) of ethyl chloroformate in 10 milliliters of THF was added dropwise. The mixture was stirred for 2 1/2 hours at OOC. At this time an aliquot from the reaction mixture showed a very strong anhydride carbonyl stretch at 1820 cm 1 in the infrared indicating the formation of the mixed anhydride l-carboethoxy-1-ethoxycarbonyloxycarbonyl-2-cyclopropene. The balance of the reaction mixture containing the mixed anhydride was carried on to Part E. Part E. PreDaration of 2-cYcloProDenvl-l-carbo- ethoxy-1-[N-(2-ethyl-4-bromqphenyl)] carboxamtde A solution of 1.40 grams (0.0075 mole) of 2-methyl-4-bromoaniline in 10 milliliters of tetrahydrofuran was added dropwise to the reaction mixture from part D at OOC. The mixture was allowed to come to room temperature and stirred for 2 hours. The reaction mixture was filtered and the filtrate concentrated under reduced pressure to give an orange colored solid. This solid was washed with ether and recrystallized from hexane-ethyl acetate to give 1.5 grams (0.004 mole) of 2-cyclopropenyl-l- carboethOxy-l-[N-(2-methyl-4-bromophenyl)]carboxamide, Compound ?56, as a white crystalline solid having a melting point of 1510C-153OC. Example XXXVIII Effect of Representati ve Malonic Acid Derivative Compounds on Plant Growth Retardation-Snaobeans and Wheat Solutlons of the test compounds identified in Table I below were prepared by dissolving 68.8 milligrams of the particular compound in 5.5 milliliters of acetone and then adding water to a final volume of 11.0 milliliters. If clouding of the solution occurred as the water was added, the use of water was discontinued and acetone was added to a final volume of 1.0 milliliters. The resulting stock solutions contained 6255 parts per million by weight of the particular compound. The test concentration in parts of the test compound per million parts by weight of final solution employed in the growth retardation tests in Table J were obtained by appropriate dilutions of the stock suspension with acetone and water (50/50 volume/volume). Seeds of snapbeans, wheat, velvetleaf, cucumber, sunflower, flax, buckwheat, tomato, perennial rye, marigold, soybean, barnyard grass, wild oats and pea were planted in a sandy loam soil in a flat having the following dimensions: 3,5 inches in width x 7.9 inches in length x 1.0 inches in height. Twelve to fourteen days after planting at the time the first trifoliolate leaf of snapbean is at least 3.0 centimeters long, each concentration of the test compounds identified in Table J was applied to one flat as a dollar spray by use of an aspirated spray apparatus set at 10 pslg air pressure (all flats sprayed at a rate of 4 pounds per acre). As a control, a water-acetone solution containing no test compound was also sprayed on a flat. When dry, all of the flats of plants were placed in a greenhouse at a temperature of 80 F + 5 F and humidity of 50 percent + 5 percent. Visual indications of growth retardation activity were observed and recorded 10 to 14 days after treatment. Visual observations of growth retardation were recorded employing a system of numerical ratings. Numerical ratings from "O" to 111011 were used to designate the degree of growth retardation activity observed in comparison with the untreated control. A 11011 rating indicates no visible response, a "5" rating indicates 50 percent more growth retardation in comparison with the control, and a "10" rating indicates 100 percent more growth retardation in comparison with the control. Stated in a similar way, a "5" rating indicates that the increment in plant growth is only half that of the control or that the plant has increased in growth at half the rate of the control. This rating system indicates any retardation of plant height as compared to the untreated control. The results are reported in Table J. TABLE J Effect of Representative Malonic Acid Derivative Compounds on Plant Growth Retardation - Snapbeans Compound Growth Retardation No. Rating Control O 1 2 2 4 5 7 10 2 11 7 13 2 14 2 15 4 18 1 20 2 21 6 22 9 25 6 26 4 28 6 29 2 30 2 33 2 34 6 35 8 36 2 37 5 38 5 40 3 43 2 TABLE J (Cont.) Effect of Representative Malonic Acid Derivative Compounds on Plant Growth Retardation - Snapbeans Compound Growth Retardation No. Rating 44 2 45 2 46 9 47 2 49 3 50 3 51 3 57 6 58 4 63 2 66 5 67 2 69 2 70 5 71 2 74 2 75 6 78 2 79 5 80 2 81 2 82 3 83 2 84 4 85 2 86 2 TABLE J (Cont.) Effect of Representative Malonic Acid Derivative Compounds on Plant Growth Retardation - Snanbeans Compound Growth Retardation No. Rating 87 2 88 3 90 2 92 4 94 2 95 3 98 3 99 4 100 3 101 2 102 7 104 2 105 3 107 3 108 2 110 4 111 9 112 3 114 4 115 3 116 7 117 2 118 2 120 2 121 4 122 4 TABLE J (Cont.) Effect of Renresentative Malonic Acid Derivative Compounds on Plant Growth Retardation - Snapbeans Compound Growth Retardation No. Rating 123 3 125 5 126 4 128 2 129 5 135 3 140 3 141 1 144 6 145 4 146 3 147 4 148 5 149 3 150 1 151 3 153 3 154 2 159 4 168 1 173 2 175 4 TABLE J (Cont.) Effect of Representative Malonic Acid Derivative Compounds on Plant Growth Retardation - Snaobeans Compound Growth Retardation No. Rating 212 2 213 8 216 3 218 3 219 2 222 2 223 2 224 4 226 2 228 2 232 2 233 6 234 10 235 8 236 8 237 2 TABLE J Effect of Renresentative Malonic Acid Derivative Compounds on Plant Growth Retardation - Wheat Compound Growth Retardation No. Rating Control O 22 1 46 2 69 3 82 2 84 2 88 2 92 3 107 2 110 2 111 3 114 4 115 5 116 2 117 2 121 2 122 2 123 2 125 2 126 2 129 2 144 3 145 3 146 2 TABLE J (Cont.) Effect of- Representative Malonic Acid Derivative Compounds on Plant Growth Retardation - Wheat Compound Growth Retardation No. Rating 212 1 213 7, 216 3 218 2 219 5 224 2 233 5 234 5 235 5 236 5 237 4 The results in Table J demonstrate that treatment of plants with certain malonic acid derivative compounds provides significant growth retardatlon in comparison with untreated control plants. ExamPle XXXIX Effect of Representative Malonic Acid Derivative Compounds on Plant Growth Retardation-Wheat Solutlons of the test compounds identified in Table J below were prepared by dissolving the compounds in acetone/water (50:50 volume/volume) containing 0.05 percent volume/volume of Triton X-100 surfactant commercially available from Rhom and Haas Company, Philadelphia, Pennsylvania. As detailed below, these solutions of test compounds were applied to wheat at a concentration of 0.5 pounds of active ingredient per acre or 1.0 pounds of active ingredient per acre. Wheat seeds were planted in a sandy loam soil in a flat having the following dimensions: 3.5 inches in width x 7.9 inches in length x 1.0 inches in height. Eight days after emergence at the 2-3 leaf growth stage of wheat, each concentration of the test compounds identified in Table J was applied to one flat as a foliar spray by use of an aspirated spray apparatus set at 10 psig air pressure (all flats sprayed at a volume of 120 gallons per acre). As a control, a water-acetone solution containing no test compound was also sprayed on a flat. When dry, all of the flats of wheat were placed in a greenhouse at a temperature of 80 F + 5"F and humidity of 50 percent + 5 percent. Visual indications of growth retardation activity were observed and recorded 14 days after treatment. Visual observations of growth retardation were recorded employing a system of percentage ratings. These percentage ratings from 0 to 100 were used to designate the degree of growth retardation activity observed in comparison with the untreated control. A 0 percent rating indicates no visible response, a 50 percent rating indicates that the increment in wheat growth is only half that of the control or that wheat has increased in growth at half the rate of the control and a 100 percent rating indicates a maximum response. This rating system indicates any retardation of wheat height as compared to the untreated control. The results are reported in Table K. TABLE K Effect of RePresentative Malonic Acid Derivative Compounds on Plant Growth Retardation - Wheat Compound Rate Percent Growth No. (Pounds/Acre) Retardation Control -- 0 Compound 96 0.5 30 1.0 40 Compound 111 0.5 60 1.0 70 Compound 114 0.5 20 1.0 30 Compound 82 0.5 10 1.0 10 Compound 115 0.5 30 1.0 40 Compound 116 0.5 40 1.0 70 Compound 117 0.5 50 1.0 60 The results in Table K demonstrate that treatment of wheat with certain malonic acid derivative compounds provides significant growth retardation in comparison with untreated control wheat. Example XL Effect of Representative Malonic Acid Derivative ComPounds on Plant Growth Retardation-Red Mapl e and SYcamore Solutlons of the test compounds identified in Table K below were prepared by dissolving the compounds in acetone/water (50:50 volume/volume) containing 0.1 percent volume/volume of Triton X-100 surfactant commercially available from Rhom and Haas Company, Philadelphla, Pennsylvania. As detailed below, these solutions of test compounds were applied to red maple and sycamore at a concentration of 1.0, 2.0 or 4.0 pounds of active ingredient per acre. Bare-root seedlings of red maple (Acer rubrum) and sycamore (Platanus occidentalis) were obtained commercially and grown in one gallon plastic containers containing a sandy loam soil.. The seedlings were maintained in a greenhouse at a temperature of 80 F + 5 F and humidity of 50 + 5 percent. After a period of one month, the developing trees were disbudded to one main dominant shoot 4-6 inches in length. At this time, each concentration of the test compounds identified in Table K was applied to separate trees as a dollar spray by use of an aspirated spray apparatus set at 10 psig air pressure (all trees sprayed at a volume of 120 gallons per acre). As a control, a water-acetone solution containing no test compound was also sprayed on certain trees. When dry, all of the trees were returned to the greenhouse for a period of one month. Measured indications of growth retardation activity were observed and recorded at this time (one month after treatment). The percent retardation of shoot elongation in Table L was determined by actual measurement of the shoot of each tree which was compared to the untreated control. The average shoot length of the untreated control trees was 48 centimeters for red maple and 53 centimeters for sycamore. The results in Table L represent the average of 3 repetitions. TABLE L Effect of Representative Malonic Acid Derivative Compounds on Plant Growth Retardation - Red Maple and Sycamore Percent Retardation of Shoot Elongation Compound Rate Red No. (Pounds per Acre) Maple Svcamore Control -- 0 0 Compound 96 1.0 34 15 2.0 40 16 4.0 43 20 Compound 111 1.0 76 77 2.0 97 84 4.0 97 88 The results in Table L demonstrate that treatment of red maple and sycamore with certain malonic acid derivative compounds provides significant growth retardation in comparison with untreated control red maple and sycamore. Example XLI Effect of Representative Malonic Acid Derivative Comnounds on Plant Growth Retardation-Red Maple and SYcamore Solutions of the test compounds identified in Table M below were prepared by dissolving the compounds in acetone/water (50:50 volume/volume) containing 0.1 percent volume/volume of Triton X-100 surfactant commercially available from Rhom and Haas Company, Philadelphia, Pennsylvania. As detailed below, these solutions of test compounds were applied to red maple and sycamore at a concentration of 1.0 or 2.0 pounds of active ingredient per acre. Bare-root seedlings of red maple (Acer rubrum) and sycamore (Platanus occidentalis) were obtained commercially and grown in one gallon plastic containers containing a sandy loam soil. The seedlings were maintained in a greenhouse at a temperature of 80"F + 5"F and humidity of 50 + 5 percent. After a period of 3 months, the developing trees were pruned to a 50 percent reduction in height. At 24 days after pruning, each concentration of the test compounds identified in Table M was applied to separate trees as a foliar spray by use of an aspirated spray apparatus set at 10 psig air pressure (all trees sprayed at a volume of 120 gallons per acre). As a control, a water-acetone solution containing no test compound was also sprayed on certain trees. When dry, all of the trees were returned to the greenhouse for a period of 45 days. Visual indications of growth retardation activity were observed and recorded at this tlme (45 days after treatment). The percent retardation of regrowth in Table M was determined by visual observation of the regrowth of each tree in comparison with the untreated control. A 0 percent rating indicates no visible response, a 50 percent rating indicates that the increment in tree growth is only half that of the control or that the tree has increased in growth at half the rate of the control, and a 100 percent rating indicates a maximum response. This rating system indicates any retardation of regrowth as compared with the untreated control. The results in Table M represent the average of 3 repetitions. TABLE M Effect of Representative Malonic Acid Derivative Compounds on Plant Growth Retardation - Red Maple and Sycamore Percent Retardation of Growth Compound Rate Red No. (Pounds per Acre) Maple Sycamore Control -- 0 0 Compound 96 1.0 47 8 2.0 42 9 Compound 111 1.0 85 43 2.0 91 46 The results in Table M demonstrate that treatment of red maple and sycamore with certain malonic acid-derivative compounds provides significant retardation of regrowth in comparison with untreated control red maple and sycamore.

Claims: Claims 1. A method of re@@@@ing plant growth which comprises applying cote plant an effective amount, sufficient to @@@@@ plant growth, of a compound having the form@la: EMI138.1 wherein: R1 and R2 are independently a substituted or unsubstituted, carbocyclic or heterocyclic ring system selected from a monocyclic aromatic or nonaromatic ring s'; elm, a bicyclic aromatic or nonaromatic ring ,;; -;, a polycyclic aromatic or nonaromatic ring system, and a bridged ring system which may be saturated or unsaturated in which the permissible substituents (Z) are the same or different and are one or more hydrogen halogen, alkylcarbonyl, alkylcarbonylalkyl, formyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiocyano, prqpargylthio, hydroxyimino, alkoxyimino. trialkylsilyoxy, aryldialkylsilyloxy,. triarylsilyloxy, formamidino, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino, azido, azo, aminocarbonyl, alkylaminocarbonyl, hydrazono, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, nitro, cyano, hydroxycarbonyl and derivative salts, formamido, alkyl, alkoxy, polyhaloalkyl, polyhaloalkoxy, alkoxycarbonyl, substituted amino in which the permissible substituents are the same or different and are one or two propargyl, alkoxyalkyl, alkylthioalkyl, alkyl, alkenyl, haloalkenyl or polyhaloalkenyl; alkylthio, polyhaloalkylthGo, alkylsulfinyl, polyhaloalkylsulfinyl, alkylsulfonyl, polyhaloalkylsulfonyl, alkylsulfonylamino, alkylcarbonylamino, polyhaloalkylsulfonylamino, polyhaloalkylcarbonylamino, trialkylsilyl, aryldialkylsilyl, triarylsilyl, sulfonic acid and derivative salts, phosphonic acid and derivative salts. alkoxycarbonylamino, alkylaminocarbonyloxy, dialkylaminocarbonyloxy, alkenyl, polyhaloalkenyl, alkenyloxy, alkynyl, alkynyloxy, polyhaloalkenyloxy, polyhaloalkynyl, polyhaloalkynyloxy, polyfluoroa)kanol, cyanoalkylamino, semicarbazonomethyl, alkoxycarbonylhydrazonomethyl, alkoxyiminomethyl, unsubstituted or substituted aryloxyNmlnomethyl, hydrazonomethyl, unsubstituted or substituted arylhydrazonomethyl, a hydroxy group condensed with a mono-, di- or polysaccharide, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, aryloxy, aralkoxy, arylthio, aralkylthio, alkylthioalkyl, arylthioalkyl, aryl,sulflnyl, arylsulfonyl, haloalkylsulf1.nyl, haloalkylsulfonyl, haloalkenyloxy, haloalkynyloxy, haloalkynylthio, haloalkenylsulfonyl, polyhaloalkenylsulfonyl, isocyano, aryloxysulfonyl, propargyloxy, aroyl, haloacyl, polyhaloacyl, aryloxycarbonyl, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, arylaminosulfonyl, carboxyalkoxy, carboxyalkylthio, alkoxycarbonylalkoxy, acyloxy, haloacyloxy, polyhaloacyloxy, aroyloxy, alkylsulfonyloxy, alkenylsulfonyloxy, arylsulfonyloxy, haloalkylsulfonyloxy, polyhalodlkylsul fonyl.oxy, aroylamtno, haloacylamino, alkoxycarbonyloxy, arylsulfonylamlno, aminocarbonyloxy, cyanato, isocyanato, isothiocyano, cycloalkylamino, trialkylammonium, arylamino, aryl(alkyl)amino, aralkylamino, alkoxyalkylphosphinyl, alkoxyalkylphosphinothioyl, alkylhydroxyphosphinyl, dialkoxyphosphino, hydroxyamino, alkoxyamino, aryloxyamino, aryloxyimino, oxo, thiono, diazo, alkyildene, alkylimino, hydrazono, semlcarbazono, dialkylsulfonium, dialkylsulfuranylidene, dialkyoxosulfuranylidene, -X, = X, -X = R3. = X-R3, EMI140.1 R1 and R2 are independently hydrogen or derivative salts, or a substituted heteroatom or substituted carbon atom, or a substituted or unsubstituted, branched or straight chain containing two or more carbon atoms or heteroatoms in any combination in which the permissible substituents dre Z; Y1 and Y2 are independently a substituted or unsubstituted heteroatom in which the permissible. substituents are Z; ; Y3 and Y4 are independently hydrogen, or a substituted or unsubstituted heteroatom or substituted carbon atom, or a substituted or unsubstituted, branched or straight chain containing two or more carbon atoms or heteroatoms in any combination, or halogen, alkylcarbonyl, formyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylhio, thiocyano, propargylthio, trialkylsilyloxy, aryldialkylsilyioxy, triarylsiyloxy, formamidino, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino hydrazono, azo, aminocarbonyl, alkylaminocarbonyl, azido, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, nitro; cyano, hydroxycarbonyl and derivative salts, formamido, alkyl, alkoxy, polyhaloalkyl, polyhaloalkoxy, alkoxycarbonyl, substituted amino in which the permissible substituents are the same or different and are one or two propargyl, alkoxyalkyl, alkylthioalkyl, alkyl, alkenyl, haloalkenyl or polyhaloalkenyl; alkylthio, polyhaloalkylthio, alkylsulfinyl, polyhaloalkylsulfinyl, alkylsulfonyl, polyhaloalkylsulfonyl, alkylsulfonylamino, alkylcarbonylamino, polyhaloalkylsulfonylamino, polyhaloalkylcarbonylamino, trialkylsilyl, aryldialkylsilyl, triarylsilyl, sulfonic acid and derivative salts, phosphonic acid and derivative salts, alkoxycarbonylamino, alkylaminocarbonyloxy, dialkylaminocarbonyloxy, alkenyl, polyhaloalkenyl, alkenyloxy, alkynyl, alkynyloxy, polyhaloalkenyloxy, polyhaloalkynyl, polyhaloalkynyloxy, polyfluoroalkanol, cyanoalkylamino, semicarbazonomethyl, alkoxycarbonylhydrazonomethyl, alkoxyiminomethyl, unsubstituted or substituted aryloxyiminomethyl, hydrazonomethyl, unsubstituted or substituted arylhydrazonomethyl, a hydroxy group condensed with a mono-, di- or polysaccharide, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, aryoxy, aralkoxy, arylthio, aralkylthio, alkylthioalkyl, arylthioalkyl, arylsulfinyl, arylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, haloalkenyloxy, haloalkynyloxy, haloalkynylthio, haloalkenylsulfonyl, polyhaloalkenylsuifonyl, tsocyano, aryloxysulfonyl, propargyloxy, aroyl, haloacyl, polyhaloacyl, aryloxycarbonyl, aminosulfonyl, alkylamlnosulfonyl, dlalkylaminosulfonyl, arylaminosulfonyl, carboxyalkoxy, carboxyalkylthio, alkoxycarbonylalkoxy, acyloxy, haloacyloxy, polyhaloacyloxy, aroyloxy, arlkylsufonyloxy, alkenylsulfonyloxy, arylsulfonyloxy, paloalkylsulfonyloxy, polyhaloalkylsulfonyloxy, aroylamino, haloacylamtno, alkoxycarbonyloxy, arylsulfonylamino, aminocarbonyloxy, cyanato, tsocyanato, isothiocyano, cycloalkylamino, trialkylammonium, arylamino, aryl (alkyl )amno, aralkylamino, alkoxyalkylphosphinyl, alkoxyalkylphosphinothioyl, alkylhydroxyphosphinyl, dialkoxyphoxphino, hydroxyamino, alkoxyamino, aryloxyamino, -X, -X = R3, EMI143.1 in which the permissible substituents are Z; Y3 and Y4 taken together are oxo, thiono, diazo, = X or = X - R3, or substituted or unsubstituted alkyliden, alkylimino, hydrazono, dialkylsulfuranylidene, dialkyloxosulfuranylidene. semtcarbazono, hydroxyimino, alkoxyimino or aryloxyimino in which the permissible substituents are Z; Y3 and Y4 may be linked together to form a substituted or unsubstituted, carbocyclic or heterocyclic ring system selected from a monocyclic aromatic or nonaromatic ring system, a bicyclic aromatic or nonaromatic ring system, a polycyclic aromatic or nonaromatic ring system, and a bridged ring system which may be saturated or unsaturated in which the permissible substituents are Z; and Y5 and Y6 are independently oxygen or sulfur; wherein: X is a covalent single bond or double bond, a substituted or unsubstituted heteroatom or substituted carbon atom, or a substituted or unsubstituted, branched or straight chain containing two or more carbon atoms or hetçroatoms in any combination in which the permissible substituents are Z; R3 is a substituted or unsubstituted, carbocyclic or heterocyclic ring system selected from a monocyclic aromatic or nonaromatic ring system, a bicyclic aromatic or nonaromatic ring system, a polycyclic aromatic or nonaromatic ring system, and a bridged ring system which may be saturated or unsaturated in which the permissible substltuents are Z; or R3 is a substituted heteroatom or substituted carbon atom, or a substituted or unsubstituted, branched or straight chain containing two or more carbon atoms or heteroatoms in any combination in which the permissible substituents are Z; Y7 and Y10 are independently oxygen or sulfur; Y8 and Yg are independently oxygen, sulfur, amino or a covalent single bond; and R4 and R5 are independently hydrogen or substituted or unsubstituted alkyl, alkenyl, alkynyl, polyhaloalkyl, phenyl or benzyi in which the permiss4ble substituents are Z. 2. The method of claim .i in which the compound has the formula: EMI145.1 wherein: R1 and R2 are independently a substituted or unsubstituted, carbocyclic or heterocyclic ring system selected from a monocyclic aromatic or nonaromatic ring system, a bicyclic aromatic or nonaromatic ring system, a polycyclic aromatic or nonaromatic ring system, and a bridged ring system which may be saturated or unsaturated in which the permissible substituents are Z as defined in Claim 1; or EMI145.2 ; or R1 and R2 are independently hydrogen or derivative salts, or a substituted heteroatom or substituted carbon atom, or a substituted or unsubstituted, branched or straight chain containing two or more carbon atoms or heteroatoms in any combination in which the permissible substituents are Z; Y1 and Y2 are independently a substituted or unsubstituted heteroatom in which the permissible. substituents are Z; ; Y3 and Y4 are independently hydrogen, or a substituted or unsubstituted heteroatom or substituted carbon atom, or a substituted or unsubstituted, branched or straight chain containing two or more, carbon atoms or heteroatoms in any combination, or halogen, alkylcarbonyl, formyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiocyano, proparylthio, trialkylsilyloxy, aryldialkylsilyloxy. triarylsilyloxy, formamidino, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino, hydrazino, azo, aminocarbonyl, alkylaminocarbonyl, azido, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, nitro; ; cyano, hydroxycarbonyl and derivative salts, formamido, alkyl, alkoxy, polyhaloalkyl, polyhaloalkoxy, alkoxycarbonyl, substituted amino in which the permissible substituents are the same or different and are one or two propargyl, alkoxyalkyl, alkylthioalkyl. alkyl, alkenyl, haloalkenyl or polyhaloalkenyl; alkylthio, polyhaloalkylhio. alkylsulfinyl. polyhaloalkylsulfinyl. alkylsulfonyl. polyhaloalkylsulfonyl, alkylsulfonylamino, alkylcarbonylamlno, polyhaloalkylsulfonylamino, polyhaloalkylcarbonylamlno, trialkylsilyl, aryldialkylsilyl. triarylsilyl, sulfonic atid and derivative salts, phosphonic acid and derivative salts, alkoxycarbonylamino, alkylaminocarbonyloxy. dialkylaminocarbonyloxy, alkenyl, polyhaloalkenyl, alkenyloxy, alkynyl, alkynyloxy, polyhaloalkenyloxy, polyhaloalkynyl, polyhaloalkynyloxy, polyfluoroalkanol, cyanoalkylamino, semlcarbazonomethy', alkoxycarbonylhydrazonomethyl, alkoxyiminomehyl, unsubstituted or substituted aryloxyiminomethyl, hydrazonomethyl, unsubstitutd or substituted arylhydrazonomethyl, a hydroxy group condensed with a mono-, di- or polysaccharide, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalk'yl, aryloxy, aralkoxy, arylthlo, aralkylthto, alkylthioalkyl, arylthioalkyl, arylsulfinyl, arylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, haloalkenyloxy, haloalkynyloxy, haloalkynylthio, haloalkenylsulfonyl, polyhaloalkenylsulfonyl, isocyano, aryloxysulfonyl, propargyloxy, aroyl, haloacyl, polyhaloacyl, aryloxycarbonyl, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, arylaminosulfonyl. carboxyalkoxy, carboxyalkylthio, alkoxycarbonylalkoxy, acyloxy, haloacyloxy, polyhaloacyloxy, aroyloxy, alkylsulfonyloxy, alkenylsulfonyloxy, arylsulfonyloxy, haloalkylsulfonyloxy, polyhaloalkylsulfonyloxy, aroylamino, haloacylamino. alkoxycarbonyloxy. arylsulfonylamino, aminocarbonyloxy, cranato. isocyanato, isothiocyano, cycloalkylamino, trialkylammonium, arylamino, aryl(alkyl)amino, aralkylamino, alkoxyalkylphosphinyl, alkoxyalkylphosphinothioyl, alkylhydroxyphosphinyl, dialkoxyphosphino, hydroxyamino, alkoxyamino, aryloxyamino, -X, -X = R3, EMI148.1 in which the permissible substituents are z; or Y3 and Y4 taken together are oxo, thiono, diazo, = X or = X - R3, or substituted or unsubstituted alkylidene, alkylimino, hydrazono, dialkylsulfuranylidene, dialkyloxosulfuranylidene, semicarbazono, hydroxyimino, alkoxyimino or aryloxyimino In which the permissible substituents are Z; ; Y5 and Y6 are independently oxygen or sulfur'; wherein: X is a covalent single bond or double bond, a substituted or unsubstituted heteroatom or substituted carbon atom, or a substituted or unsubstituted, branched or straight chain containing two or more. carbon atoms or heteroatoms in any combination in which the permissible substituents are Z; ; R3 is a substituted or unsubstltuted, carbocyclic or heterocyclic rlng system selected from a monocyclic aromatic or nonaromatic ring system, a bicyclic aromatic or nonaromatic ring system, a polycyclic aromatic or nonaromatic ring system, and a bridged ring system which may be saturated or unsaturated in which the permissible substituents are Z; R3 tis a substituted heteroatom or substituted carbon atom, or a substituted or unsubstituted, branched or straight chain containing two or more carbon atoms or heteroatoms in any combination in which the permissible substituents are Z; Y7 and Y10 are independently oxygen or sulfur; ; Y8 and Yg are independently oxygen, sulfur, amino or a covalent single bond; and R4 and R5 are independently hydrogen or substituted or unsubstituted alkyl, alkenyl, alkynyl, polyhaloalkyl, phenyl or benzyl in which the permissible substituents are Z. 3. The method of claim 1 in which the compound has the formula: EMI150.1 wherein: R1, R2, Y1, Y2, Y5, Y6 and Z are as defined in Claim 1 and Y3 and Y4 are linked together to form a substituted or unsubstituted, carbocyclic or heterocyclic rlng system selected from a monocyclic aromatic or nonaromatic ring system, a bicyclic aromatic or nonaromatic ring system, a polycyclic aromatic or nonaromatic ring system, and a bridged ring system which may be saturated or unsaturated in which the permissible substituents are Z. 4. The method of claim 1 in which the compound has the formula: EMI150.2 wherein: Z'8 is the same or different and is one or more hydrogen, or substituted or unsubstituted halogen, haloalkyl, polyhaloalkyl, polyhaloalkoxy, alkyl, alkoxy, alkylthio, alkylsulfonyl, alkylsulfinyl, aryl, aryloxy, arylthio, arylsulfonyl, nitro, cyano, dialkoxyphosphinyl, acyl, aroyl, alkoxycarbonyl, alkoxycarbonylalkyl, acylamino, sulfonylamino, alkylsulfonylamtno, acyloxy, alkenyl or -CH=CHCH=CH-; 38 is 0, S, NH or N (alkyl); and 7 is hydrogen, ammonium, alkylammonium, polyalkylammonium, hydroxyalkylammonium. poly(hydroxyalkyl)ammonium, an alkali metal or alkallne earth metal or substituted or unsubstituted alkyl, hydroxyalkyl, alkoxyalkyl, alkoxycarbonylalkyl, alkylaminoalkyl, dialkylaminoalkyl, aryl, mercaptoalkyl, alkylthioalkyl, arylthioalkyl, aryloxyalkyl, alkylsulfonylalkyl, alkylsulfinylalkyl, acylalkyl, aroylalkyl, dialkoxyphosphinylalkyl, diaryloxyphoxphinylalkyl, hydroxyalkylthioalkyl, hydroxyalkylsulfonylalkyl, alkoxyalkylthioalkyl, alkoxyalkylsulfonylalkyl, poly(oxyalkylene)alkyl, cyanoalkyl, nitroalkyl, alkylideneamino, carbamoylalkyl, alkylcarbamoylalkyl, dialkylcarbamoylalkyl, amtnoalkyl, acylaminoalkyl, acyloxyalkyl, alkoxycarbonylaminoalkyl, cyanoaminoalkyl, carbamoyloxyalkyl, alkylcarbamoyloxyalkyl, dialkylcarbamoyloxyalkyl, alkoxycarbonyloxyalkyl, alkoxycarbonylthioalkyl, aminosulfonylalkyl, alkylaminosulfonylalkyl or dialkylaminosulfonylalkyl: in which the permissible substituents are Z as defined in Claim 1. 5. The method of claim 1 in which the compound has the formula: EMI152.1 Z'g is the same or different and is one or more hydrogen, or substituted of unsubstttuted halogen, haloalkyl, polyhaloalkyl, polyhaloalkoxy, alkyl, alkoxy, alkylthio, alkylsulfonyl, alkylsulfinyl, aryl, aryloxy, arylthio, arylsulfonyl, nitro, cyano, dialkoyphosphinyl, acyl, aroyl, alkoxycarbonyl, alkoxycarbonylalkyl, acylamino, sulfonylamino, alkylsulfonylamino, acyloxy, alkenyl or -CH=CHCH=CH-; Y'39 is 0, S, NH or N (alkyl); and R'8 is a or derivative salts or Z as defined in Claim 1. 6. The method of claim 1 in which the compound has the formula: EMI153.1 wherein: 10 is the same or different and is one or more hydrogen, or substituted or unsubstituted halogen, haloalkyl, polyhaloalkyl,. polyhaloalkoxy, alkyl, alkoxy, alkylthio, alkylsulfonyl, alkylsulfinyl, aryl, aryloxy, arylthio, arylsulfonyl, nitro, cyano, dialkoxyphosphinyl, acyl, aroyl, alkoxycarbonyl, alkoxycarbonylalkyl, acylamino, sulfonylamino. alkylsulfonylamino, acyloxy, alkenyl or -CH=CHCH=CH-; T'40 is 0, S, NH or N (alkyl); ; 4 and Y' are independently hydrogen 5 or substituted or unsubstituted halogen, alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, alkylthio, cyano, nitro, tsocyano, formyl, amino, hydroxy, alkylcarbonyl, alkylsulfonyl, alkylsulfinyl, dialkoxyalkyl, alkylcarbonylamino, formylamino. alkylamino, dialkylamino, alkoxycarbonyl, hydroxyalkyl, polyhaloalkyl or haloalkyl; or Y'4 and Y'5 may be linked together to form a substituted or unsubstituted, carbocyclic or heterocyclic ring system selected from a monocyclic aromatic or nonaromatic ring system, a bicyclic aromatic or nonaromatic ring system, a polycyclic aromatic or nonaromatic rlng system and a bridged ring system which may be saturated or unsaturated, and R'g is hydrogen, ammonium, alkylammonium, polyalkylammonium, hydroxyalkylammontum, poly(hydroxyalkyl)ammonium, an alkali metal or alkaline earth metal or substituted or unsubstituted alkyl, hydroxyalkyl, alkoxyalkyl, alkoxycarbonylalkyl. alkylaminoalkyl. dialkylaminoalkyl, aryl. mercaptoalkyl, alkylthioalkyl, arylthioalkyl, aryloxyalkyl, alkylsulfonylalkyl, alkylsulfinylalkyl, acylalkyl, aroylalkyl, dialkoxyphosphinjylalkyl, diaryloxyphosphinylalkyl, hydroxyalkylthioalkyl, hydroxyalkylsulfonylalkyl, alkoxyalkylthioalkyl, alkoxyalkylsulfonylalkyl, poly(oxyalkylene)alkyl, cyanoalkyl, nitroalkyl, alkylideneamino, carbamoylalkyl, alkylcarbamoylalkyl, dialkylcarbamoylalkyl, aminoalkyl, acylaminoalkyl, acyloxyalkyl, alkoxycarbonyla,minoalkyl, cyanoaminoalkyl, carbamoyloxyalkyl, alkylcarbamoyloxyalkyl, dialkylcarbamoyloxyalkyl, alkoxycarbonyloxyalkyl, alkoxycarbonylthioalikyl, aminosulfonylalkyl, alkylaminosulfonylalkyl or dialkylaminosulfonylalkyl in which the permissible substituents are Z as defined in Claim 1. 7. The method of claim 1 in which the compound has the formula: EMI155.1 wherein: 11 is the same or different and is one or more hydrogen, or substituted or unsubstituted halogen, haloalkyl, polyhaloalkyl, polyhaloalkoxy, alkyl., alkoxy, alkylthio, alkylsulfonyl, alkylsulfinyl, aryl, aryloxy, arylthio, arylsulfonyl, nitro, cyano, dialkoxyphosphinyl, acyl, aroyl, alkoxycarbonyl, alkoxycarbonylalkyl, acylaminho, sulfonylamino, alkylsulfonylamino, acyloxy, alkenyl or -CH=CHCH=CH-; Y'6 is hydrogen or alkyl; Y'7. Y'8, Y'9 and Y'10 are independently hydrogen, halogen or alkyl; Y'41 is 0, S, NH or N (alkyl); and R'10 is hydrogen, ammonium, alkylammonium, polyalkylammonium, hydroxyalkylammonium, poly(hydroxyalkyl)ammonium,an alkali metal or alkaline earth metal or substituted or unsubstituted alkyl, hydroxyalkyl, alkoxyalkyl, alkocycarbonylalkyl, alkylaminoalkyl, dialkylaminoalkyl, aryl, mercaptoalkyl, alkylthioalkyl, arylthioalkyl, aryloxyalkyl, alkylsulfonylalkyl, alkylsulfinylalkyl, acylalkyl, aroylalkyl, dialkoxyphosphinylalkyl, diaryloxyphosphinylalkyl, hydroxyalkylthioalkyl, hydroxyalkylsulfonylalkyl, alkoxyalkylthioalkyl, alkoxyalkylsulfonylalkyl, poly(oxyalkylene)alkyl, cyanoalkyl, nitroalkyl, alkylideneamino, carbamoylalkyl, alkylcarbamoylalkyl, dialkylcarbamoylalkyl, aminoalkyl, acylaminhoalkyl, acyloxyalkyl, alkoxycarbonylaminoalkyl, cyanoaminoalkyl, carbamoyloxyalkyl, alkylcarbamoyloxyalkyl, dialkylcarbamoyloxyalkyl, alkoxycarbonyloxyalkyl, alkoxycarbonylthioalkyl, aminosulfonylalkyl, alkylaminosulfonylalkyl or dialkylaminosulfonylalkyl;in which the permissible subsitutents are Z as defined ill Claim 1. 8. The method of claim 1 in which the compound has the formul EMI156.1 wherein: 12 is the same or different and is one or more hydrogen, or substituted or unsubstituted halogen, haloalkyl, polyhaloalkyl, polyhaloalkoxy, alkyl, alkoxy, alkylthio, alkylsulfonyl, alkylsulfinyl, aryl, aryloxy, arylthio, arylsulfonyl, nitro, cyano, dialkoxyphosphinyl, acyl, aroyl, alkoxycarbonyl, alkoxycarbonylalkyl, acylamino, sulfonylamino, alkylsulfonylamino, acyloxy, alkenyl or -CH-=CHCH=CH-: Y'11, Y'12, Y'13, Y'14, Y'15, and Y'16 are independently hydrogen,halogen or alkyl; Y'42 is 0, S, NH or N (alkyl); and 11 is hydrogen, ammonium, alkylammonium, polyalkylammonium, hydroxyalkylammonium, poly(hydroxyalkyl)ammonium, an alkali metal or alkaline earth metal or substituted or unsubstituted alkyl, hydroxyalkyl, alkoxyalkyl, alkoxycarbonylalkyl, alkylaminoalkyl, dialkylaminoalkyl, aryl, mercaptoalkyl, alkylthioalkyl, arylthioalkyl, aryloxyalkyl, alkylsulfonylalkyl, alkylsulftnyla.lkyl, acylalkyl, aroylalkyl, dlalkoxyphosphlnylal,kyl, diaryloxyphosphinylalkyl, hydroxyalkylthioalkyl, hydroxyalkylsulfonylalkyl, alkoxyalkylthioalkyl, alkoxyalkylsulfonylalkyl, poly(oxyalkylene)alkyl, cyanoalkyl, nitroalkyl, alkylideneamino, carbamoylalkyl, alkylcarbamoylalkyl, dialkylcarbamoylalkyl, aminoalkyl, acylaminoalkyl, acyloxyalkyl, alkoxycarbonylaminoalkyl, cyanoaminoalkyl, carbamoyloxyalkyl, alkylcarbamoyloxyalkyl, dialkylcarbamoyloxyalkyl, alkoxycarbonyloxyalkyl, alkoxycarbonylthioalkyl, aminosulfonylalkyl, alkylaminosulfonylalkyl or dialkylaminosulfonylalkyl; in which the permissible substituents are Z as defined in Claim 1. 9. The method of claim 1 in which the compound has the formula: EMI157.1 wherein: 13 is the same or different and is one or more hydrogen, or substituted or unsubstituted halogen, haloalkyl, polyhaloalkyl, polyhaloalkoxy, alkyl, alkoxy, alkylthio, alkylsulfonyl, alkylsulf1nyl, aryl, aryloxy, arylthio, arylsulfonyl, nitro, cyano, dGalkoxyphosphtnyl, acyl, aroyl, alkoxycarbonyl, alkoxycarbonylalkyl, acylamino, sulfonylamino, alkylsulfonylamino, acyloxy, alkenyl or -CH=CHCH=CH-; 17 is hydrogen or alkyl; Y'18, Y'19, Y'20 and Y'21, are independently hydrogen, halogen or alkyl; Y143 is 0, S, NH or N (alkyl); and 12 is a derivative salt or Z as defined in Claim 1. 10. The method of claim 1 in which the compound has the formula: EMI158.1 wherein: Z'14 is the same or different and is one or more hydrogen, or substituted or unsubstituted halogen, haloalkyl, polyhaloalkyl, polyhaloalkoxy, alkyl, alkoxy, alkylthio, alkylsulfonyl, alkylsulfinyl, aryl, aryloxy, arylthio, arylsulfonyl, nitro, cyano, dialkoxyphosphinyl, acyl, aroyl, alkoxycarbonyl, alkoxycarbonylalkyl, acylarnino, sulfonylamino, alkylsulfonylamino, acyloxy, alkenyl or -CH=CHCH=CH-; 21' Y'22, Y'23, Y'24, Y'25, and 26 are independently hydrogen, halogen or alkyl; 44 is 0, S, NH or N (alkyl); and 13 is a derivative salt or Z'as defined in Claim 1. 11. The method of claim 1 in which the compound has the formula: EMI159.1 wherein: 15 is the same or different and is one or more hydrogen, or substituted or unsubstituted halogen, haloalkyl, polyhaloalkyl, polyhaloalkoxy, alkyl, alkoxy, alkylthio, alkylsulfonyl, alkylsulfinyl, aryl, aryloxy, arylthio, arylsulfonyl, nitro, cyano, dialkoxyphosphinyl, acyl, aroyl, alkoxycarbonyl, alkoxycarbonylalkyl, acylamino, sulfonylamino, alkylsulfonylamino, acyloxy, alkenyl or -CH=CHCH=CH-; 27 is 0, S, NH or N (alkyl); ; Y'28 completes a substituted or unsubstituted, carbocylic or heterocyclic ring system selected from a monocyclic aromatic or nonaromatic ring system, a bicyclic aromatic or nonaromatic ring system, a polycyclic aromatic or nonaromatic ring system and a bridged ring system which may be saturated or unsaturated; y'45, is 0, 5, NH or N (alkyl); and R'14 is a derivative salt or Z as defined In Claim 1. 12. The method of claim 1 in which the compound has the formula: EMI160.1 wherein: 16 is the same or different and is one or more hydrogen, or subst1tuted or unsubstituted halogen, haloalkyl, polyhaioalkyl, polyhaloalkoxy, alkyl,' alkoxy, alkylthio, alkylsulfonyl, alkylsulfinyl, aryl, aryloxy, arylthio, arylsulfonyl, nitro, cyano, dialkoxyphosphinyl, acyl, aroyl, alkoxycarbonyl, alkoxycarbonylalkyl, acylamino, sulfonylamino, alkylsulfonylamino, acyloxy, alkenyl or -CH=CHCH=CH-; yi29 is 0, S, NH or N (alkyl); ; Y'30 and Y'31 are Independently hydrogen, or substituted or unsubstituted halogen, cycloalkyl, isocyano, alkylsulfonyl, alkylsulfinyl, alkylamino, dlalkylamWno, alkoxycarbonyl, alkenyl, alkynyl, alkyl, alkoxy, alkylthio-, cyano, notio, formyl, amino, hydroxy, alkylcarbonyl, dialkoxyalkyl, alkylcarbonylamino. formylamino, hydroxyalkyl, polyhaloalkyl or haloalkyl; or 30 and Y131 may be linked together to form a substituted or unsubstituted, carbocyclic or heterocyclic ring system selected from a monocyclic aromatic or nonaromatic ring system, a bicyclic aromatic or nonaromatic ring system, a polycyclic aromatic or nonaromatic ring system and a bridged ring system which may be saturated or unsaturated; Y'46 is 0, S, NH or N (alkyl); and R'15 Is a derivative salt or Z as defined In Claim 1. 13. The method of claim 1 in which the compound has the formula: EMI161.1 whereon: 17 is the same or different and Is one or more hydrogen, or substituted or unsubstituted halogen, haloalkyl, polyhaloalkyl, polyhaloalkoxy, alkyl, alkoxy, alkylthio, alkylsulfonyl, alkylsulflnyl, aryl, aryloxy, arylthio, arylsulfonyl, nitro, cyano, dialkoxyphosphinyl, acyl, aroyl, alkoxycarbonyl, alkoxycarbonylalkyl, acylamino, sulfonylamino, alkylsulfonylamino, acyloxy, alkenyl or -CH=CHCH=CH-; Y'32 jis 0, S, N or N (alkyl); Y'33 and Y'34 ar independently hydrogen, or substituted or unsubstituted halogen, alkyl, alkoxy, alkylthio, polyhaloalkyl or haloalkyl; or Y'33 and Y # 34 may be linked together to form a substituted or unsubstituted, carboxyclic or heterocyclic ring system selected from a monocyclic aromatic or nonaromatic ring system, a bicyclic aromatic or nonaromatic ring system, a polycyclic aromatic or nonaromatic ring system and a bridged ring system which may be saturated or unsaturated; Y'47 1s 0, S, NH or N (alkyl), and 16 is a derivative salt or Z as defined in Claim 1. 14. The method of,claim 1 in which the compound has the formula: EMI162.1 wherein: 17 is a substituted or unsubstituted heterocyclic ring system selected from a monocyclic aromatic or nonaromatic ring system, a bicyclic aromatic or nonaromatic ring system, or polycyclic aromatic or nonaromatic ring system, and a bridged ring system which may be saturated or unsaturated; Y'35 is 0, S, N or N (alkyl); ; Y'36 and Y'37 are independently hydrogen, or substituted or unsubstituted halogen, cycloalkyl, isocyano, alkylsulfonyl, alkylsulfinyl, alkylamino, dialkylamino, alkoxycarbonyl, alkenyl, alkynyl, alkyl, alkoxy, alkylthio, cyano, nitro, formyl, amino, hydroxy, alkylcarbonyl, dialkoxyalkyl, alkylcarbonylamlno, formylamtno, hydroxyalkyl, polyhaloalkyl or haloalkyl; or and and Y' may be linked together to 37 form a substituted or unsubstituted, carbocyclic or heterocyclic ring system selected from a monocyclic aromatic or nonaromatic ring system, a bicyclic aromatic or nonaromatic ring system, a polycyclic aromatic or nonaromatic ring system and a bridged ring system, which may be saturated or unsaturated; 48 is 0, S, N or N (alkyl); and 18 is a derivative salt qr Z as defined in Claim 1. 15. The method of claim l in which the compound has the formula: EMI163.1 16. The method of claim l in which the compound has the formula: EMI163.2 17. The method of claim 1 in which the compound has the formula: EMI164.1 18. The method of claim l in which the compound has the formula: EMI164.2 19. The method of claim 1 in which the compound has the formula: EMI164.3 20. The method of claim 1 in which the compound has the formula: EMI165.1 21. The method of claim 1 in which the compound has the formula: EMI165.2 22. The method of claim 1 in which the compound has the formula: EMI165.3 23. The method of claim l in which the compound has the formula: EMI166.1 24. The method of claim 1 in which the compound has the formula: EMI166.2 25. The method of claim 1 in which the compound has the formula: EMI166.3 26. The method of claim 1 in which the compound has the formula: EMI167.1 27. The method of claim 1 in which the compound has the formula: EMI167.2 2a. The method of claim 1 in which the compound has the formula: EMI167.3 29. A method of retarding plant growth which' comprises applying to the plant an effective amount, sufficient to retard plant growths of a compound of claim. 6. 30. The method of claim 1 wherein the compound is applied to the plant in an amount sufficient to retard plant growth without causing substantiai phytotoxicity. 31. The method of claim 1 wherein the compound is applied to the plant at a period prior to the plant reproductive growth phase. 32. The method of claim 1 wherein the compound is applied to the plant at a period during the plant reproductive growth phase. 33. The method of claim # wherein the compound is applied to the plant at a concentration of from about 0.001 to about 100 pounds of compound per acre. 34. The method of claim 1 wherein the compound is applied to the plant at a concentration of from about 0.01 to about 15 pounds of compound per acre. 35. The method of claim 1 wherein the plant is any agronomic or horticultural plant, woody plants, ornamental or, turfgrass. 36. The method of claim 1 wherein the plant is a woody plant selected from red maple, sycamore, red oak, American elm, linden, ginkgo, oaks, ashes, maples, apple trees, Chinese elm, crabapples, Russlan olive, silver maple, sugar maple, water oak, poplars and conifers. 37. The method of claim 1 wherein the plant is selected from corn, cotton, sweet potatoes, white potatoes, alfalfa, wheat, rye, rice, barley, oats, sorghum, dry beans, soybeans, sugar beets, sunflowers, tobacco, tomatoes, canola, deciduous fruit, citrus frut, tea, coffee, olives, pineapple, banana, sugar cane, cocoa, oil palm, herbaceous bedding plants, woody shrubs, turfgrasses, ornamental plants, evergreens, trees and flowers. 38. A compound having the formula: EMI169.1 wherein: R1 and R2 are independently a substituted or unsubstituted, carbocyclic or heterocyclic ring system selected from a monocyclic aromatic or nonaromatic ring system, a bicyclic aromatic or nonaromatic ring system. a polycyclic aromatic or nonaromatic ring system, and a bridged ring system which may be saturated or unsaturated; or R1 and R2 are independ'elit ly hydrogen or derivative salts, or a substituted heteroatom or substituted carbon atom, or a substituted or unsubstituted, branched or straight chain containing two or more carbon atoms or heteroatoms in any combination; Y1 and Y are independently a substituted or unsubstituted heteroatom; Y3 and Yq are linked together to form a substituted or unsubstituted, carbocyclic or heterocyclic ring system selected from a monocyclic aromatic or nonarornatic ring system, a bicyclic aromatic or nonaromatic ring system, a polycyclic aromatic or nonaromatic ring system, and a bridged ring system which may be saturated or unsaturated; Y5 and Y6 are independently oxygen or sulfur; in which the permissible substituents are Z as defined in Claim 1. 39. A compound of claim 38 selected from the following: EMI171.1 wherein: Z4 is independently substituted or unsubstituted halogen, haloalkyl, polyhaloalkyl, polyhaloalkoxy, alkyl, alkoxy, alkylthio, alkylsulfonyl, alkylsulfinyl, aryl, aryloxy, arylthto, arylsulfonyl, nitro, cyano, dialkoxyphosphinyl, acyl, aroyl, alkoxycarbonyl, alkoxycarbonylalkyl, acylamino, sulfonylamino, alkylsulfonylamino, acyloxy, alkenyl or -CH=CHCH=CH-; n is a value of from 0 to 5; u is 0, S or NR13 wherein R13 is hydrogen or alkyl; Y22 is 0, S, NH or N (alkyl); Y23, Y24, Y25 and Y26 are independently hydrogen, alkyl or halogen; and R12 is hydrogen, ammonium, alkylammonium, polyalkylammonium, hydroxyalkylammonium, poly(hydroxyalkyl)ammonlum, an alkali metal or alkaline earth metal or substituted or unsubstituted alkyl, hydroxyalkyl, alkoxyalkyl, alkoxycarbonylalkyl, alkylaminoalkyl, dialkylaminoalkyl, aryl, mercaptoalkyl, alkylthioalkyl, arylthioalkyl, aryloxyalkyl, alkylsulfonylalkyl, alkylsulfinylalkyl, acylalkyl, aroylalkyl, dlalkoxyphosphlnylalkyl, diaryloxyphosphinylalkyl, hydroxyalkylthioalkyl, hydroxyalkylsulfonylalkyl, alkoxyalkylthioalkyl, alkoxyalkylsulfonylalkyl, poly(oxyalkylene)alkyl, cyanoalkyl, nitroalkyl, alkylideneamino, carbamoylalkyl, alkylcarbamoylalkyl, dialkylcarbamoylalkyl, aminoalkyl, acylaminoalkyl, acyloxyalkyl, alkoxycarbonylaminoalkyl, cyanoaminoalkyl, carbamoyloxyalkyl, alkylcarbamoyloxyalkyl, dialkylcarbamoyloxyalkyl, alkoxycarbonyloxyalkyl, alkoxycarbonylthioalkyl, aminosulfonylalkyl, alkylam1nosulfo,nylalkyl or dialkylaminosulfonylalkyl; EMI173.1 wherein: Z2 is independently substituted or unsubstltuted halogen, haloalkyl, polyhaloalkyl, polyhaloalkoxy, alkyl, alkoxy, alkylthio, alkylsulfonyl, alkylsuylfinyl, aryl, aryloxy, arylthio, arylsulfonyl, nitro, cyano, dialkoxyphosphinyl, acyl, aroyl, alkoxycarbonyl, alkoxycarbonylalkyl, acylamino, sulfonylamino, alkylsulfonylamino, acyloxy, alkenyl or -CH=CHCH=CH-; n is a value of from Oto 5; Y13 is 0, S or NR9 wherein Rg 15 hydrogen or alkyl; Y14 is 0, S, NH or N (alkyl); Y15 and Y16 are as indicated in Claim 38; or Y15 and Y16 may be linked together to form a substituted or unsubstituted heterocyclic rlng system selected from a monocyclic aromatic or nonaromatic ring system, a bicyclic aromatic or nonaromatic ring system, a polycyclic aromatic or nonaromatic ring system and a bridged ring system which may be saturated or unsaturated; and R8 is hydrogen, ammonium, alkylammonium, polyalkylammonium, hydroxyalkylammonium, poly(hydroxyalkyl)ammontum, an alkali metal or alkaline earth metal or substituted or unsubstituted alkyl, hydroxyalkyl, alkoxyalkyl, alkoxycarbonylalkyl, alkylaminoalkyl, dlalkylaminoalkyl, aryl, mercaptoalkyl, alkylthioa,lkyl, arylthioalkyl, aryloxyalkyl, alkylsulfonylalkyl, alkylsulfinylalkyl, acylalkyl, aroylalkyl, dialkoxyphosphinylalkyl, diaryloxyphosphinylalkyl, hydroxyalkylthioalkyl, hydroxyalkylsulfonylalkyl, alkoxyalkylthioalkyl, alkoxyalkylsulfonylalkyl, poly(oxyalkylene)alkyl, cyanoalkyl, nitroalkyl, alkylideneamino, carbamoylalkyl, alkylcarbamoylalkyl, dialkylcarbamoylalkyl, aminoalkyl, acylaminoalkyl, acyloxyalkyl, alkoxycarbonylaminoalkyl, cyanoaminoalkul, carbamoyloxyalkyl, alkylcarbamoyloxyalkyl, dialkylcarbamoyloxyalkyl, alkoxycarbonyloxyalkyl. alkoxycarbonylthioalkyl, amlnosulfonylalkyl, alkylaminosulfonylalkyl or dialkylaminosulfonylakyl); EMI174.1 wherein: Z5 is independently substituted or unsubstituted halogen, haloalkyl, polyhaloalkyl, polyhaloalkoxy, alkyl, alkoxy, alkylthio, alkylsulfonyl, alkylsulfinyl, aryl, aryloxy, arylthio, arylsulfonyl, nitro, cyano, dialkoxyphosphinyl, acyl, aroyl, alkoxycarbonyl, alkoxycarbonylalkyl, acylamino, sulfonylamino, alkylsulfonylamino, acyloxy, alkenyl or -CH=CHCH=CH-; n is a value of from 0 to 5; Y27 is 0, S or NR15 wherein R15 is hydrogen or alkyl; Y28 is O S, NH or N (alkyl); Y29, Y30, Y31, Y32, Y33 and T34 are independently hydrogen, alkyl or halogen; and R14 is the same as R12 ; and EMI175.1 wherein: Z6 is independently substttuted or unsubstiuted halogen, haloalkyl, polyhaloalkyl, polyhaloalkoxy, alkyl, alkoxy, alkylthio, alkylsulfonyl, alkylsulfinyl, aryl, aryloxy, arylthio, arylsulfonyl, nitro, cyano, dialkoxyphosphinyl, acyl, aroyl, alkoxycarbonyl, alkoxycarbonylalkyl, acylamino, sulfonylamino, alkylsulfonylamino, acyloxy, alkenyl or -CH=CHCH=CH-;' n is a value of from 0 to 5; Y35 Is 0, S or NR17 wherein R17 is hydrogen or alkyl; Y36 is O or S; and R16 is the same as R12 in which the permissible substituents for the above formulae are as described for Z in Claim 38, 40. The compound of claim 38 having the formula: EMI176.1 wherein: Z4 is independently substituted or unsubstituted halogen, haloalkyl, polyhaloalkyl, polyhaloalkoxy, alkyl, alkoxy, alkylthio, alkylsulfonyl, alkylsulfinyl, aryl, aryloxy, arylthio, arylsulfonyl, nitro, cyano, dialkoxyphosphinyl, acyl, aroyl, alkoxycarbonyl, alkoxycarbonylalkyl, acylamino. sulfonylamino. alkylsulfonylamino, acyloxy, alkenyl or -CH=CHCH=CH-; n is a value of from 0 to 5; Y21 is O, S or NR13 wherein R13 is hydrogen or alkyl; Y22 is 0, S, NH or N (alkyl); Y23, Y24, Y25 and Y26 are independently hydrogen, alkyl or halogen; and Ra2 is as defined in Claim 39; in which the permissible substituents are as defined for Z in claim 38. 41. The compound of claim 38 having the formula: EMI177.1 wherein: Z5 is independently substituted or unsubstltuted halogen, haloalkyl, polyhaloalkyl, polyhaloalkoxy, alkyl, alkoxy, alkylthio, alkylsulfonyl, alkylsulfinyl, aryl, aryloxy, arylthio, arylsulfonyl, nitro, cyano, dialkoxyphosphinyl, acyl, aroyl, alkoxycarbonyl, alkoxycarbonylalkyl, acylamino, sulfonylamino. alkylsulfonylamino, acyloxy, alkenyl or -CH=CHCH=CH-; n is a value of from 0 to 5; Y27 is O, S or NR15 wherein R15 is hydrogen or alkyl; Y28 is 0 S, NH or N (alkyl); Y29, Y30, Y31, Y32, Y33 and Y34 are independently hydrogen, alkyl or halogen; and Rl4 is as defined in Claim 38; in which the permissible substituents are as defined for Z in claim 38. 42, The compound of claim 38 having the EMI177.2 wherein: Z6 is independently substituted or unsubstituted halogen, haloalkyl, polyhaloalkyl, polyhaloalkoxy, alkyl, alkoxy, alkylthio, alkylsulfonyl, alkylsulfinyl, aryl, aryloxy, arylthio, arylsulfonyl, nitro, cyano, dialkoxyphoxphinyl, acyl, aroyl, alkoxycarbonyl, alkoxycarbqnylalkyl, acylamino, sulfonylamino, alkylsulfonylamino, acyloxy, alkenyl or -CH=CHCH=CH-; n is a value of from O to ; Y35 is 0, S or NRa7 wherein R17 is hydrogen or alkyl; Y36 is O or S; and Ra6 is as defined in Claim 39; in which the permissible substituents are as defined for Z in claim 38. 43. A compound having the. formula: EMI178.1 wherein,: Z2 is independently substituted or unsubstituted halogen, haloa,lkyl1 polyhaloalkyl, polyhaloalkoxy, alkyl, alkoxy, alkylthio, alkylsulfonyl, alkylsulfinyl, aryl, aryloxy, arylthio, arylsulfonyl, nitro, cyano, dialkoxyphosphinyl, acyl, aroyl, alkoxycarbonyl, alkoxycarbonylalkyl, acylamino, sulfonylamino, alkylsulfonylamino, acyloxy, alkenyl or -CH=CHCH=CH-; n is a value of from 0 to 5; 'Y13 is 0, S or NRg wherein R9 is hydrogen or alkyl; Y14 is 0, S, NH or N (alkyl); ; Y15 and Y16 are independently hydrogen, alkyl, halogen, alkoxy, alkylthio, alkenyl, alkynyl, hydroxy, cyano, nitro, formyl, amino, alkylcarbonyl, dialkoxyalkyl, alkylcarbonylamino, formylamino, hydroxyalkyl, haloalkyl or polyhaloalkyi with the following provisos: : (a) when Y15 is alkoxy other than methoxy, at least one of Y16 and Z2 is other than hydrogen; (b) when Y15 is acyl, cyano or nitro, then Y16 is alkyl, alkenyl, alkynyl or halogen; (c) when Ya5 is hydroxy or mercapto, Z2 is other than hydrogen; (d) when Y15 is amino or dialkylamino and Y16 is hydrogen, Z2 is neither 2,6-dimethyl nor ortho-2-fluoro-4-lodobenzoyl; (e) when Y15 15 alkylamino and Y16 15 methoxy, then Z2 is other than hydrogen; (f) when Y15 is bromo and Y16 is hydrogen, then Z2 is other than hydrogen or 2.6-dimjethyl and further provided that at least one of Y15 and Y16 is othr than hydrogen; and Y5 and Y6 are independently oxygen or sulfur; in which the permissible substituents are Z as defined in Claim 1. 44. The composition of Claim 43 having the formula EMI180.1 wherein Y13 is nitrogen, Y14 is oxygen, Y15 is hydrogen, Y16 is methoxy, R8 is C1 C8 alkyl and Z2 is C1, Br. F or CF3. 45. A composition for retarding plant growth comprising an acceptable carrier and an effective amount, sufficient to retard plant growth, of a compound of claim 38. 46. The method of claim 1 in which the compound is used in combination with one or more other biologically active compounds. 47. The method of claim 1 in which the compound is a derivative salt. 48. The method of claim 45 in which the derivative salt is selected from an alkali metal, an alkaline earth metal, ammonium, alkylammonium, polyalkylammonium, hydroxyalkyl'ammonium, poly(hydroxyalkyl)ammon1um or mixtures thereof. - 49. . The method of clalm 1 in which the compdund has the formula: EMI181.1 - 50 . The method of claim 1 in which the compound has the formula: EMI181.2 - 51, A compound having the formula: EMI181.3

Inventors: CAPPY JAMES JOSEPH, COOKE ANSON RICHARD, FRITZ CHARLES DAVID, MANNING DAVID TREADWAY, SEE RAYMOND MICHAEL, WHEELER THOMAS NEIL, CAPPY, JAMES, JOSEPH, COOKE, ANSON, RICHARD, FRITZ, CHARLES, DAVID, MANNING, DAVID, TREADWAY, SEE, RAYMOND, MICHAEL, WHEELER, THOMAS, NEIL
Applicants: RHONE POULENC BV, RHONE-POULENC BV
Application year: 1987
Main classification: C07C103
IPC codes: A01N37, A01N39, A01N41, A01N43, A01N53, A01N55, C07C67, C07C69, C07C233, C07C239, C07C327, C07D213, C07D237, C07D239, C07D241, C07D251, C07D257, C07D261, C07D275, C07D277, C07D285, C07D295, C07D307, C07D317, C07D333, C07D339, C07F9