DD254318A5 - METHOD FOR REDUCING HUMIDITY LOSS IN PLANTS - Google Patents

Abstract

The invention relates to a method for lowering the Transpirationsfeuchtigkeitsverlustes of plants and to increase the crop yield by applying a heterocyclic, nitrogen-containing compound on the plant surface or crop.

Description

Field of application of the invention

The invention relates to a method for reducing the Transpirationsfeuchtigkeitsverlustes of plants and to increase the crop yield by applying novel, heterozykliBcher, nitrogen-containing compounds.

Characteristic of the known state of the art

Transpiration is a well-known physiological process involving the passage of water in the form of live tissue vapor. During plant perspiration, water vapor enters the atmosphere through the stomata of the plant, facilitating the absorption and translocation of the aqueous nutrients by plant root systems. The stomata also allow for the necessary gas exchange between plant tissue and outside air. It is believed that only about one percent of the total amount of water absorbed by the plant roots is utilized for plant growth, while the remainder is released through the stomata of the plant via transpiration into the atmosphere.

It has been found that only a very slow transpiration rate of the plants is needed for the necessary nutrient transport and plant growth. Although the complete end of transpiration for the plants would most likely be detrimental or even fatal, it is believed that a reduction in plant transpiration rate of up to about 40 to 50 % would not be detrimental to the plants, see, for example, U.S. Patent 4,094,845 · Reduction The loss of plants' water through transpiration is important for a variety of reasons; in particular for reducing water requirements for irrigation in arid climates, for protecting plants from withering or other damage during transplanting or shipping or in very cold weather and for reducing water pollution in certain types of environment. By water stress or water stress is meant in this context situations in which the transpiration rate exceeds the rate of water absorption by the plant. Water stress occurs in the form of a reduction in plant water potential and turgor, and can lead to withering or other forms of damage or even death of the plant.

Various methods have been developed to reduce the transpiration moisture loss of plants. Such methods are described, for example, in US Pat. Nos. 4,094,845, 4,397,681, 3,890,158, 3,847,641, 3,826,671, 3,676,102, 3,539,373, 3,339,990, 3,199,944 and also in EP 73 760-B. Carboxylated hydrophilic acrylic polymers, wax emulsions, animal tallow, alkenyl succinic acids, long chain esters of lower organic acids, polyisocyanates, liquid polyterpenes, benzyl alkylammonium salts, and others are examples of the various materials described in the patent literature and used to reduce water loss by transpiration similar. But if these materials can also reduce the transpiration moisture loss of plants, many of them have a detrimental effect on other plant processes such as photosynthesis, respiration, cell division, and the like.

the use of S-chloro-ethylamino-e-isopropylaminos-triazine (atrazine) to reduce the water loss of plants by transpiration has also been reported in the literature. See, for example, G. D. Wills et al. a., Weeds 11: 253-255 (1963), and also James C. Graham et al. a., Weed Science 16; 389-392 (1968). With the use of atrazine as an antiperspirant compound, however, the inhibition of plant reactions that take place photosynthetically and therefore light "need, connected, for example, the photosynthetic electron transport, and phytotoxicity.

Object of the invention

It is therefore an object of the present invention to provide a method for the use of certain heterocyclic, nitrogen-containing compounds for lowering the moisture content.

Loss of plants by transpiration and thus to make more effective use of soil moisture. Another object of the present invention is to use certain heterocyclic nitrogen-containing compounds to increase crop yields

Explanation of the invention of the invention

The invention relates to a method for reducing the moisture loss of plants, which consists in applying to the plant surface an effective amount of a compound which is sufficient to reduce the loss of moisture from the plant surface, without substantially inhibiting the photosynthetic electron transport of the plant Compound has the following formula:

and X have the following definition.

The invention also relates to a method of increasing the crop yield, which comprises applying to the crop an effective amount sufficient to increase crop yield, without substantially inhibiting the photosynthetic electron transport of the plant, to produce a compound having the following formula :

R ₁ -ZR ₂

wherein R

I ¹

and X have the following definition.

As stated above, the invention relates to a method for reducing the moisture loss of plants and increasing crop yields through the use of certain heterocyclic nitrogen-containing compounds. More particularly, the invention relates to a method for reducing the moisture loss of plants by transpiration and increasing crop yields, which consists of adding to a compound an effective amount sufficient to reduce the moisture loss from the plant surface or to increase crop yield. without appreciably inhibiting the photosynthetic electron transport of the plant, to the plant surface or crop, the compound having the formula:

wherein:

R _{1 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 bridging ring system which may be saturated or unsaturated in which the permissible substituents (Z) are identical or different and one or more hydrogen atoms, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiozyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxy, formamidino, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, Polyhaloalkoxysulfonyl, hydroxy, amino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, nitro, cyano, hydroxycarbonylgru ppe and derived salts are formamido, alkyl, alkoxy, polyhaloalkyl, polyhaloalkoxy, alkoxycarbonyl, substituted amino in which the permissible substituents are the same or different and one or two propargyl, alkoxyalkyl, alkylthioalkyl, alkyl Alkenyl, haloalkenyl or polyhaloalkenyl group; Alkylthio, polyhaloalkylthio, alkylsulfinyl, polyhaloalkylsulfinyl, alkylsulfonyl, polyhaloalkylsulfonyl, alkylsulfonylamino, alkylcarbonylamino, polyhaloalkylsulfonylamino, polyhaloylalkylcarbonylamino, trialkylsilyl, aryldialkylailyl, triarylsilyl, sulfonic acid and derived salts, phosphonic acid and derived salts, Alkoxycarbonylamino, alkylaminocarbonyloxy, dialkylaminocarbonyloxy, alkenyl, polyhaloalkenyl, alkenyloxy, alkyl

nyl, alkynyloxy, polyhaloalkenyloxy, polyhaloalkynyl, polyhaloalkynyloxy, polyfluoroalkenes, cyanoalkylamino, semicarbazonomethyl, alkoxycarbonylhydrazonomethyl, alkoxyiminomethyl, unsubstituted or substituted aryloxyiminomethyl, hydrazonomethyl, unsubstituted or substituted arylhydrazonomethyl, a hydroxy group condensed with a mono-, Di- or polysaccharide, haloalkyl, haloelkenyl, haloalkyriyl, alkoxyalkyl, aryloxy, aralkoxy, arylthio, aralkylthio, alkylthioalkyl, arylthioalkyl, arylaulfinyl, arylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, haloalkenyloxy, haloalkynyloxy, haloalkynylthio -, haloalkenylsulfonyl, polyhaloalkenylsulfonyl, alkoxysulfonyl, aryloxysulfonyl, propargyloxy, aroyl, haloazyl, polyhaloazyl, aryloxycarbonyl, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, arylaminosulfonyl, carboxyalkoxy, carboxyalkylthio, alkoxycarbonylalkoxy, azyloxy -, Haloazyloxy-, Polyhaloazyloxy-, Aroyloxy-, Alkylsu lfonyloxy, alkenylsulfonyloxy, arylsulfonyloxy, haloalkylaulfonyloxy, polyhaloalkylsulfonyloxy, aroylamino, haloazylamino, alkoxycarbonyloxy, arylsulfonylamino, aminocarbonyloxy, cyanato, isocyanato, isothiocyanato, cycloalkylamino, trialkylammonium, arylamino, aryl ( alkyl) amino, aralkylamino, alkoxyalkylphosphinyl, alkoxyalkylphosphinothioyl, alkylhydroxyphosphinyl, dialkyloxyphosphino, hydroxyamino, alkoxyamino, aryloxyamino, aryloxyimino, oxo, thiono, alkylaminoalkoxy, dialkylaminoalkoxy, alkoxyalkylene, alkoxyalkenyl, cyanoalkoxy Dialkylsulfonium group, -X, = 2, -X = R ₃ , = XR ₃ ,

-XR ₃ , -P-Y ₂ R ₄ ,

Y ₃ R ₅

JL

Y ₃ R ₅

or

R 1 is a substituted heteroatom or substituted carbon atom, or is a substituted or unsubstituted, branched or straight chain containing two or more carbon atoms or heteroatoms in any combination in which the permissible substituents (Z) are the same or different and one or; more of the following are hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiozyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxy, e-aminamidino, alkylsulfamido, dialkylsulfamido , Alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, nitro, cyano, hydroxycarbonyl and derived salts, ammamido, alkyl, alkoxy, polyhaloalkyl, polyhaloalkoxy, alkoxycarbonyl , substitutes amino group in which the permissible substituents are identical or different and one or two propargyl, alkoxyalkyl, alkylthioalkyl, alkyl, alkenyl, haloalkenyl or polyhaloalkenyl group are alkylthio, polyhaloalkylthio, alkylsulfinyl, polyhaloalkylsulfinyl, alkylsulf onyl, polyhaloalkylsulfonyl, alkylsulfonylamino-j alkylcarbonylamino, polyhaloalkylsulfonylamino, polyhaloalkylcarbonylamines, trialkylsilyl, aryldialkylailyl, triarylsilyl, sulfonic and derived salts, alkoxycarbonylamino, alkylaminacarbonyloxy, dialkylaminocarbonyloxy, alkenyl, polyhaloalkenyl, alkenybxy Alkynyl, alkynyloxy " polyhaloalkenybxy, polyhaloalkynyl, polyhaloalkynyloxy, polyfluoroalkanol, cyanoalkylamino, semicarbazonomethyl, alkoxycarbonylhydrazonomethyl, alk, oxyiminomethyl, unsubstituted or substituted aryloxyiminomethyl, hydrazonomethyl, unsubstituted or substituted arylhydrazonomethyl, hydroxy, condensed with a mono-, di- or polysaccharide, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, aryloxy, aralkoxy-r, arylthio, aralkylthio, alkylthioalkyl, arylthioalkyl, arylsulfinyl, arylsulfonyl, haloalkylsulfinyl, haloalkylaulmono- , Haloalkenyloxy, haloalkynyloxy, haloalkynylthio, haloalkenylsulfonyl, polyhaloalkenylsulfonyl,

Alkoxyaulfonyl, aryloxysulfonyl, propargyloxy, aroyl, haloazyl, polyhaloazyl, aryloxycarbonyl, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, arylamino-sulfonyl, carboxyalkoxy, carboxyalkylthio, alkoxycarbonylalkoxy, azyloxy, haloalzyloxy, polyhaloyazyloxy, Aroyloxy, alkylaulonyloxy, alkenylsulfonyloxy, arylsulfonyloxy, haloalkylaulfonyloxy, polyhaloalkylaulonyloxy, aroylamino, haloazylamino, alkoxycarbonyloxy, arylsulfonylamino, aminocarbonyloxy, cyanato, isocyanato, isothiozyano, cycloalkylamino, trialkylammonium, arylamino, , Aryl (alkyl) amino, aralkylatnino, alkoxyalkylphosphiayl, alkoxyalkylphoaphinothioyl, alkylhydroxyphoaphinyl, dialkoxyphoaphino, hydroxyamines), alkoxyamino, aryloxyamino, aryloxyimino, oxo, thiono, alkylaminoalkoxy, dialkylaminoalkoxy, alkoxyalkoxy, Alkoxyalkenyl, cyanoalkoxy, dialkylsulfonium group, -X, = X, -X = R ,, = X-Rn,

-X - R ₃ ,

I ¹

P- Y ₂ R ₄ ,

^Y 3 ^R 5

i ¹

-X ₄ -P-

Y ₃ R ₅

^Y 2 ^R 4

^Y -3 ^R 5

X is a divalent single or double bond iat, a substituted or non-substituted heteroatom or subatomized carbon atom, or a substituted or unsubstituted, branched or straight chain containing two or more carbon atoms or heteroatoms in any combination wherein the permissible substituents (Z) are the same or and one or more of the following: hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, ₍ thiozyano, propargylthio, hydroxyimino, alkoxyimino, irialkylsilyloxy, aryldialkylsilyloxy, triarylailyloxy, pormamidino , Alkylsulfamido, dialkylsulfamido, alkoxyaulfonyl, polyhalolakoxysulfonyl, hydroxy, amino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, nitro, cyano, hydroxycarbonyl and derived salts; ammmamido, alkyl,

Alkoxy, polyhaloalkyl, polyhaloalkoxy, alkoxycarbonyl, subatized amino group in which the permissible substituents are the same or different and one or two of the following: propargyl, alkoxyalkyl, alkylthioalkyl, alkyl, alkenyl, haloalkenyl or polyhaloalkenyl; Alkylthio, polyhaloalkylthio, alkylhalfinyl, polyhaloalkylaulfinyl, alkylsulfonyl, polyhaloylsulfonyl, alkylsulfonylamino, alkylcarbonylamino, polyhaloalkylsulfonylamino, polyhaloalkylcarbonylamino, trialkylsilyl, aryldialkylailyl, triarylailyl, sulfonic acid and derived salts, phoaphonic acid and derived salts, alkoxycarbonylamino -, alkylaminocarbonyloxy, dialkylaminocarbonyloxy, alkenyl, polyhaloalkenyl, alkenyloxy, alkynyl, alkynyloxy, polyhaloalkenyloxy, polyhaloalkynyl, polyhaloalkynyxy, polyfluoroalkanol, zyaaoalkylamino, semicarbazonomethyl, alkoxycarbonylhydrazonomethyl, alkoxyiminomethyl, non-dusted or aubatituted aryloxyiminomethyl, hydrazonomethyl, unsubstituted or substituted with arylhydrazonomethyl, a hydroxy group, condensed with a mono-, di- or polysaccharide haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, aryloxy, aralkoxy, aralthio, aralkylthio, alkylthioalkyl, arylthioalkyl, arylsulfonyl, A rylsulfonyl, Haloalkylaulfinyl, haloalkylsulfonyl, Haloalkenyloxy-, Haloalkynyloxy-, Haloalkynylthio-, Haloalkenylsulfonyl, PoIyhaloalkenylsulfonylgruppe, alkoxysulfonyl, aryloxysulfonyl, Pröpargyloxygruppe, aroyl, Haloazyl, Polyhaloazyl, Aryloxykarbonyl, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, arylaminosulfonyl, Karboxyalkoxy-, Karboxyalkylthio-, Alkoxykarbonylalkoxy-, Azyloxy, haloazyloxy, polyhaloazyloxy, araoyloxy, alkylsulphonyloxy, alkenylsulphonyloxy, arylaulfonyloxy, haloalkylsulphonyloxy, polyhaloalkylsulphonyloxy, aroylamino, haloazylamino, alkoxycarbonyloxy, arylsulphonylamino, aminocarbonyloxy, cyanato,

Isocyanato, isothiozyano, cycloalkylamino, trialkylammonium, arylamino, aryl (alkyl) amino, aralkylamino, alkoxy. alkylphoaphinyl, alkoxyalkylphosphinothioyl, alkylhydroxyphoaphinyl, dialkoxyphosphino, hydroxyamines, alko-xyamino, aryloxyamino, aryloxyimino, oxo, thiono, alkylaminoalkoxy, dialkylaminoalkoxy, alkoxyalkoxy, alkoxyalkenyl, cyanoalkoxy, dialkylphthalonium groups,

-X, = X, -X

}, = Χ-Κ ·,)

-Χ - R ^ f - P - Xp

, ^Y 2 ^R 4

Y ₃ R ₅

-Y ₄ - P-

"Y ₃ R ₅

and

R ₂ is an aliphatic or unsubstituted heterocyclic ring anatate having less than one nitrogen atom, it is 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 bridging ring acid that may be saturated or unsaturated; wherein the permissible substituents (Z) are identical or different and are one or more of the following: hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, ihiozyano, propargythio, hydroxyimino, alkoxyimino, trialkysilyloxy, Aryldialkylailyloxy, triarylailyloxy, imomamidino, alkylsulfamido, dialkylsulfamido, alkoxy sulfonyl, polyhaloalkoxyaulfonyl, hydroxy, amino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylamine othiocarbonyl, vitro, cyano, hydroxycarbonyl and derived salts, formamido, alkyl, alkoxy, polyhaloalkyl, polyhaloalkoxy, alkoxycarbonyl, substituted amino in which the permissible substituents are the same or different and one or two of the following: propargyl, alkoxyalkyl, alkylthioalkyl, Alkyl, alkenyl, haloalkenyl or polyhaloalkenyl; Alkylthio, polyhaloalkylthio, alkylsulfinyl, polyhaloalkylsulfinyl, alkylaulphonyl, polyhaloalkylsulfonyl, alkylsulfonylamino, alkylcarbonylamino, polyhaloalkylsulfonylamino, polyhaloalkylcarbonylamino , trialkylailyl, aryldialkylsilyl, triarylsilyl, sulfonic acid and derived salts, phoaphonic acid and derived salts, alkoxycarbonylamino -, ~ Alkylaminokarbonyloxy, Dialkylaminokarbonyloxygruppe, alkenyl, Polyhaloalkenyl, alkenyloxy, alkynyl, alkynyloxy, Polyhaloalkenyloxy group, Polyhaloalkynyl, Polyhaloalkynyloxygruppe, Polyfluoroalkanol, Zyanoalkylaminogruppe, Semikarbazonomethyl, Alkoxykarbonylhydrazonomethyl, Alkoxyiminoraethyl, unaubatituiertea or substituted Aryloxyiminomethyl, Hydrozonomethyl, unsubatituiertes or aobstituiertes Arylhadrazonomethyl, a hydroxy group condensed with a mono-, di- or polysaccharide, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, aryloxy, aralkoxy, arylthio, aralkylthio, alkylthioalkyl, arylthioalkyl, Arylsulfinyl, Arylaulfonyl, HaIoialkylaulfinyl, haloalkylsulfonyl, Haloalkenyixy-, Haloalkynyloxy-, Haloalkynylthiogruppe, Haloalkenylsulfonyl, PoIyhaloalkenylaulfonyl, Alkoxysulfonyl, aryloxysulphonyl _s PROPAR gyloxygruppe, aroyl, Haloazyl, Polyhaloazyl, Aryloxykarbonyl, Aminoaulfonyl, Alkylaminoaulfonyl, dialkylaminosulfonyl, Arylaminoaulfonyl, Karboxyalkoxy-, Karboxyalkylthio-, Alkoxykarbonylalkoxy Aayloxy _S haloazyloxy, polyhaloazyloxy, aroyloxy, alkylsalphonyloxy, alkenylaulfonyloxy, arylsulphonyloxy, haloalkylaulofonyloxy, polyhaloalkylsulphonyloxy, aroylamino, haloazylamino, arkoarykarbonyloxy, arylsulphonylamino, aminocarbonyloxy, cyanato, isocyanato, Isothiocyanato, cycloalkylamino, trialkylammonium, arylamino, aryl (alkyl) amino, aralkylamino, alkoxyalkylphoaphinyl, alkoxyalkylphophinothioyl, alkylhydroxyphosphinyl, dialkoyphosphino, hydroxyamino, alkoxyamino, aryloxyamino, aryloxyimino, oxo, thiono, alkylaminoalkoxy

oxy, dialkylaminoalkoxy, alkoxyalkoxy, alkoxyalkenyl, cyanoalkoxy, dialkylsulfonium,

-X, = X, -X = R ₁ , = XR ₁ ,

, -P- ϊ ₂ κ ₄ ,

wherein?

K _{3 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 bridging ring system which may be saturated or unsaturated in which the permissible substituents (Z) are the same or different and are one or more of the following: hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiozyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy , Aryldialkylsilyloxy, triarylsilyloxy, formamidino, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminothioc arbonyl, nitro, cyano group, hydroxy carbonyl and derived salts, pormamido group, alkyl, alkoxy group, polyhaoalkyl, polyhaloalkoxy group, alkoxy carbonyl, substituted amino group in which the permissible substituents are the same or different and are one or two of the following: propargyl, alkoxyalkyl, alkylthioalkyl, Alkyl, alkenyl, haloalkenyl or polyhaloalkenyl; Alkylthio, polyhaloalkylthio, alkylsulfinyl, polyhaloalkylsulfinyl, alkylsulfonyl, polyhaloalkylsulfonyl, alkylsulfonylamino, alkylcarbonylamino, polyhaloalkylsulfonylamino, polyhaloalkylcarbonylamino, trialkylailyl, aryldialkylsilyl, triarylsilyl, sulfonic acid and derived salts, phosphonic acid and derived salts, alkoxycarbonylamino, alkylaminocarbonyloxy, dialkylaminocarbonyloxy Alkenyl, polyhaloalkenyl, alkenyloxy group, alkynyl, alkynyloxy, polyhaloalloxy group, polyhaloalkynal, polyhaloalkynyoxy group, polyfluoroalkanol, cyanoalkylamino group, semicarbazonomethyl, alkoxycarbonylhydrazononemethyl, alkoxyiminomethyl, unsubstituted or substituted aryloxyiminomethyl, hydrazonomethyl, unsubstituted or substituted arylhydrazonomethyl, hydroxy group condensed with a mono-, di or polysaccharide, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, aryloxy, aralkoxy, arylthio, aralkylthio, alkylthioalkyl, arylthioalkyl, aryl lsulfinyl, arylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, HaIoalkenyloxy-, Haloalkynyloxy-, Haloalkynylthiogruppe, HyIoalkenylsulfonyl, Polyhaloalkenylsulfonyl, alkoxysulfonyl, aryloxysulfonyl, Propargyloxygruppd, aroyl, Haloazyl, PoIyhaloazyl, Aryloxykarbonyl, aminosulfonyl, Alkylaminojsulfonyl, dialkylaminosulfonyl, arylaminosulfonyl, Karboxyalkoxy-, Karboxyalkylthio-, Alkoxykarbonylalkoxy- , Azyloxy, haloazyloxy, polyhaloazyloxy, aroyloxy, alkylsulfonyloxy, alkenylsulfonyloxy, arylsulfonyloxy, haloalkylsulfonyloxy, polyhaloalkylsulfonyloxy, aroylamino, haloazylamino, alkoxycarbonyloxy, arylsulfonylamino, aminocarbonyloxy, cyanato, isocyanato, isothiozyano , Cycloalkylamino, trialkylammonium, arylamino, aryl (alkyl) amino, aralkylamino, alkoxyalkylphosphinyl, alkoxyalkylphosphinothioyl, alkylhydroxyphosphinyl, dialkcsyphosphino, hydroxyamino, alkoxyamino, aryloxyamino, aryloxyimino, oxo, thiono, alkylaminoalkoxy, dialkylaminoalkoxy, , AIk-. oxyalkoxy group, alkoxyalkenyl, cyanoalkoxy group, dialkylsulfonium,

-X, = Σ, -Χ

/ ₂ ^R 4

or

R is a substituted heteroatom or substituted carbon atom or a substituted or unsubstituted, branched or straight chain having two or more carbon atoms or heteroatoms in any combination in which the permissible substituents (Z) are the same or different and are one or more of the following: Hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiozyano, propagylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxy, pormamidino, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy , Amino, arminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, nitro, cyano, hydroxycarbonyl and derived salts, imideamido, alkyl, alkoxy, polyhaloalkyl, polyhaloalkoxy, alkoxycarbonyl, substituted Amino group in which the permissible substituents are the same or different and are one or two of the following: pisopargyl, alkoxyalkyl, alkylthioalkyl, alkyl, alkenyl, haloalkenyl or polyhaloalkenyl; Alkylthio, polyalkylalkylthio, alkylsulfonyl, alkylsulfinyl, polyhaloalkylsulfinyl, polyhaloalkylsulfonyl, alkylsulfonylamino, alkylcarbonylamino, polyhaloalkylsulfonylamino, polyhaloalkylcarbonylamino, trialkylsilyl, aryldialkylsilyl, triarylsilyl, sulfonic acid and derived salts, phosphonic acid and deprotected salts, alkoxycarbonylamino, alkylaminocarbonyloxy, Dialkylaminocarbonyloxy, alkenyl, polyhaloalkenyl, alkenyloxy, alkynyl, alkynyoxy, polyhaloalkenyloxy, polyhaloalkynyl, polyhaloalkynyloxy, polyfluoroalkanol, cyanoalkylamino, semicarbazo-oxyethyl, alkoxycarbonylhydrazonomethyl, alkoxyiminomethyl, unsubstituted or substituted aryloxynitninomethyl, hydrozonomethyl, unsubstituted or substituted arylhydrazonomethyl, a hydroxy group condensed with a mono , Dt or polysaccharide, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, aryloxy, aralkoxy, arylthio, aralkylthio, alkylthioalkyl, arylthioalkyl, arylsulfinyl, A rylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, Haloalkenytoxy-, HaIoalkynyloxy-, Haloalkynylthiogruppe, Haloalkenylsulfonyl, Polyhaloalkenylsulfonyl, alkoxysulfonyl, aryloxysulfonyl, propargyloxy, aroyl, Haloazyl, Polyhaloazyl, Aryloxykarbonyl, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, arylaminosulfonyl, Karboxyalkoxy-, Karboxyalkythio-, Alkoxykarbonylakoxy-, Azyloxy , Haloazyloxy, polyhaloazyloxy, aroyloxy, alkylsulfonyloxy, alkenylsulfonyloxy, arylsulfonyloxy, haloalkylsulfonyloxy, polyhaloalkylsulfonyloxy, aroylamino, haloazylamino, alkoxycarbonyloxy, arylsulfonylamino, aminocarbonyloxy, cyanato, isocyanato, isothiocyano, Zykloalkylaminogruppe, trialkylammonium _s arylamino, aryl (alkyl) amino, aralkylamino, AIkoxyalkylphosphinyl, AIkoxyalkylphösphinothioyl, Alkylhydroxyphosphinyl, Dialkpiyphosphino-, Hydroxyamine-, alkoxyamino, Aryloxyamino-, Aryloxyimino-, oxo, thiono, alkylaminoalkoxy, Dialkylaminoalkoxy-, AIkoxyalkoxygruppe , A alkoxyalkenyl, cyanoalkoxy, dialkylsulfonium,

 · * ·> = 2, t ".χ χ - R ₃ -P-

JX- j

X-R.

Y ₃ R ₅ '

X ₁ and Y are independently oxygen or sulfur;

Y ₂ and Y are independently oxygen, sulfur, amino or a divalent bond, and

R. and R ₅ are independently hydrogen or substituted or niohtsubstituiertes alkyl, polyhaloalkyl, phenyl or benzyl, in which the permissible substituents (Z) are identical or different and one or more of the following are: hydrogen, halogen, Alkylkarbonyl, Alkylkarbonylalkyl, Alkoxykarbonylalkyl, Alkoxycarbonylalkylthio, polyhaloalkenylthio, thiozyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxy, formamidino, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, Aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, nitro, cyano, hydroxycarbonyl and derived salts, formamido, alkyl, alkoxy, polyhaloalkyl, polyhaloalkoxy, alkoxycarbonyl, substituted amino in which the permissible substituents are the same or different and one or two any of the following are: propargyl, alkoxyalkyl, alkylthioalkyl, alkyl, alkenyl, haloalkenyl or polyhaloalkenyl; Alkylthio, Polyhaloalkylthiogruppe, alkylsulfinyl, Polyhaloalkylsulfinyl, alkylsulfonyl, Polyhaloalkylsulfonyl, alkylsulfonylamino, Alkylkarbonylamino-, Polyhaloalkylsulfonylamino-, Polyhaloalkylkarbonylaminigruppe, Trialkylsi-yi, aryldialkylsilyl, triarylsilyl Sulfonaäure and derivative salts, phosphonic acid and derivative salts, Alkoxykafbonylamino-, Alkylaminokarbonyloxy-, Dialkylaminokarbonyloxygruppe, Alkenyl, polyalkenyl, alkenyloxy group, alkynyl, alkynyloxy group, polyhaloalkenyloxy group, polyhaloalkenyl, polyhaloalkynyloxy group, polyfluoroalkanol, cyanoalkylamino group, semicarbazonomethyl, alkoxycarbonylhydrazonomethyl, alkoxyiminomethyl, unsubstituted and substituted aryloxyimiriomethyl, hydrozonomethyl, unsubstituted or substituted arylhydrazonomethyl, a hydroxy group condensed with a mono-, di- or Polysaccharide, alkylthioalkyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, aryloxy, aralkoxy, arylthio, aralkylthio group, Arylthioalkyl, arylsulfinyl, arylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, Haloalkenyloxy-, Haloalkynyloxy-, Haloalkynylthiogruppe, Haloalkenylsulfonyl, Polyhaloalkenylsulfonyl, alkoxysulfonyl, aryloxysulfonyl, propargyloxy, aroyl, Haloazyl, Polyhaloazyl, Aryloxykarbonyl, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, arylaminosulfonyl, Karboxyalkoxy-, Karboxyalkylthio-, Alkoxycarbonylalkoxy, azyloxy, haloazyloxy, polyhaloazyloxy, aroyloxy, alkylsulfonyloxy, alkenylsulfonyloxy, arylsulfonyloxy, haloalkylaulofonyloxy, polyhaloalkylsulfonyloxy, aroylamino, haloazylamino, alkoxycarbonyloxy, arylsulfonylamino, aminocarbonyloxy, cyanato, isocyanato , Isothiocyanato, cycloalkylamino, trialkylammonium, arylamino, aryl (alkyl) amino, aralkylamino, alkoxyalkylphoaphinyl, alkoxyalkylphosphinothioyl, alkylhydroxyphoaphinyl, dialkoxyphosphino, hydroxyamines, alkoxyamino, aryloxyamino, aryloxyimino, oxo, thiono, alkylaminoakoxy , Dialkylamino alkoxy, alkoxyalkoxy, alkoxyalkenyl, cyanoalkoxy, dialkylsulfonium,

-Χ, = X, -Χ

-X - R ₃ , -P 5 ^ X ₂ R ₄ , or Y R ^{3 5} · X ₃ R

The above-mentioned alkyl-containing components may contain between 1 and about 100 carbon alanes or more, preferably 1 to about 30 carbon atoms, and most preferably between 1 and about 20 carbon atoms. The polysaccharide component may contain up to about 50 carbon atoms. It will be a-

estimated that all compounds included in formula J _{- are} compounds with no unfilled binding positions. It is further estimated that the valency of a sub-substituent, in order for it to be permissible for the compounds included in the formula J _, must be matched to the binding capacity of the particular carbon atom or heteroatom.

and R. in the formula I

Monocyclic ring systems by

J _- can be represented by the generalized formula 2 as follows:

^B 1 Z '

wherein B ^ represents a saturated or unsaturated carbon atom and A _{1 represents} a ring-shaped chain of atoms which together with B- form a cyclic system containing from 0 to 4 double formations or from 0 to 2 triple bonds. A ^ may contain a total of 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 independently selected from W, O, S, P or other heteroatoms, or may be 4 ring-forming heteroatoms contained alone.

Monocyclic ring systems,

those represented by R "in the formula 2

may include any monocyclic ring system of R 1 and R 2 having at least one nitrogen atom.

Ring-forming heteroatoms may in some cases carry oxygen atoms, as in aromatic and aliphatic N-oxides and ring systems containing the sulfinyl, sulfonyl, selenium oxide and phosphine oxide components.

Selected atoms in the cycles formed by B ^ and A ^ containing more than three ring-forming atoms can carry carbonyl, thiocarbonyl, substituted or unsubstituted imino groups, or substituted or unsubstituted methylidene groups.

The group designated Z represents one or more sub-substituents independently selected from the group of substituents defined herein for Z. If the cycle formed by B., and A. contains less than 4 ring-forming members, it should be a saturated carbocycle, ie, cyclopropyl. If the cycle formed by B ₁ and A- contains less than 5 ring-forming members, it should not contain more than 1 heteroatom.

Illustrative monocyclic ring structures included by R and Ro in the formula J _- include the following:

6th

Y f *

d &

¹ I ¹

wherein Bp and Bo independently represent a saturated or unsaturated carbon atom or a saturated nitrogen atom, A ₂ and A ₃ independently represent the ring-forming chains of atoms described below, and Z represents one or more substituents independently the group of substituents defined herein for Z are selected. Combinations of A ₂ and A, in combination with B ₂ or B _3, may contain from O to five double bonds, A ₂ and A ₃ may contain, independently of B ₂ and B ₃ , in total between 1 and carbon atoms, a combination of 1 to 3 heteroatoms independently selected from K, O, S, P or other heteroatoms, together with 1 to 10 carbon atoms, or they may contain 1 to 3 ring-forming heteroatoms alone.

Ring-forming heteroatoms may in certain cases carry oxygen atoms, as in aromatic and aliphatic H-oxides and ring systems containing sulfinyl, sulfonyl, selenium oxide and phoaphinoxide groups. Selected carbon atoms contained in A ₂ and A- can carry carbonyl, thiocarbonyl, substituted or unsubstituted imino groups or substituted or unsubstituted methylidene groups.

where Z has the definition given herein.

Bizyclic ring systems, which are included in the formula by R.sup.1 and R.sup.2, can be represented by the generalized formulas ^ and ^ - as follows:

Bicyclic ring systems included by B ₂ in Formula ₁ may include any bicyclic ring system of R, and R having at least one nitrogen atom. , ·

To those by the formulas 3, and is to be noted the following:

enclosed structures

(a) When B ₂ and B _{3 are} both nitrogen, the groups Ag and A _{3 should} each contain not less than three ring atoms;

(b) If A ₂ or A ₃

but not B ₃

g _{3 is} nitrogen, should either

_{2 3} at least three Ringafcome and the other contain at least two ring atoms;

i.FJ -tv Oi

(ο) If one of the groups A ₂ or A contains less than three ring atoms, the other should contain at least three ring atoms, and the bridgehead atoms should be saturated; (d) When the group A "or A- contains a carbon atom bearing a carbonyl, thiocarbonyl, imino or methylene group, it should form a cycle with at least four members together with B ₂ and B;

(e) When an annular double bond is exocyclic to one of the two rings shown in Structures 2 and A , it should be contained in a ring containing at least five members and be exocyclic to a ring containing at least five members; and

Z Z

Z Z

Z Z

(f) When a group A ₂ or Aj is linked to bridgehead B ₂ and B by double bonds, it is considered that the group A contains ₂ or A-, a double bond, and the bridgehead atoms are considered to be unsaturated.

One can recognize that bicyclic ring systems that are defined for R ^ · and Ro, may be spiro cyclic ring systems, not t on the fused bicyclic structures of IOrmeln 2 ¹¹ * are ί limited. "Spiro cyclic ring systems can be saturated or unsaturated carbocyclic or heterocyclic ring systems and may be independently substituted by one or more substituents Z as defined herein.

Currently ZZ

Illustrative bicyclic ring structures represented by R ₁ and R-.

β · J

in the formula J _- include, among others, the following:

Z Z 2 2

k5 43 \

ΑΛΙ

'Μ

Polycyclic ring systems, ie, more than 2 rings, which are included by R ₁ and R 1 in formula 1_ can be represented by the generalized formulas J j, 6, % ¹ d 8 as follows:

wherein B., B ", Bg and B" may independently be a saturated or unsaturated carbon atom or a saturated nitrogen atom and A., A-, Ag and A "independently represent ring-forming chains of atoms together with one or the other (but not both) of the two associated bridgehead atoms can contain between 0 and 2 double bonds. The groups Z represent one or more substituents independently selected from the group of substituents defined herein for Z.

The ring-forming elements of A., A _5, Ag and A "may, independently of example, Bc Bg and B" between 1 and 11 carbon atoms, a combination of 1-10 carbon atoms and 1-3 heteroatoms may contain the are independently selected from N, O, S, P or other heteroatoms, or may contain 1-3 heteroatoms alone. Ring-forming heteroatoms may in certain cases carry oxygen atoms, as in aromatic N-oxides and ring systems containing sulfinyl, sulfonyl, selenium oxide and phosphine oxide groups. The group Ag can sometimes be defined as a bond. Selected carbon atoms contained in A., A, -, Ag and A ₁ may carry one or more carbonyl, thiocarbonyl or substituted or unsubstituted imino groups.

In the structure 8, the groups Bg, Bg and Bq independently represent a saturated or unsaturated carbon atom or a saturated nitrogen atom. The group B ₁₁ may represent a saturated or unsaturated carbon atom or a nitrogen or a phosphorus atom. The groups Ag, Ag and A ₁ Q represent ring-forming chains of atoms which together with one of the groups Bg, Bg,

and

0-2 double bonds may contain.

The ring-forming elements of the groups Ag, Ag and A ₁₀ can, independently of the. Groups Bg, B_, B ₁₀ and B ₁₁ contain between 2 and 10 carbon atoms, may contain from 1 to 10 carbon atoms in combination with 1-3 heteroatoms, which may independently be selected from N, O, S, P or other heteroatoms, or may contain 2 to 3 heteroatoms alone. Ring-forming heteroatoms may carry oxygen atoms in some cases, such as in Η-oxides and in ring systems containing the sulfinyl, sulfonyl, selenium oxide and phosphine oxide groups. Selected carbon atoms contained in the groups Ag, A _g and A ₁₀ may carry one or more carbonyl, thiokarbonyl or substituted or unsubstituted imino groups *

It can be seen that the polycyclic ring systems defined for R ₁ and R can be spirocyclic ring systems and are not limited to the fused polycyclic structures of formulas jj, §_, J. and 8. Spirocyclic ring systems may be saturated or unsaturated, carbocyclic or heterocyclic, and may be independently substituted by one or more of the substituents Z defined herein.

Polycyclic ring systems, which are included by Rg in the formula J _- can be any polycyclic ring system or Shen.

and R, with at least one nitrogen atom einschlieIllustrative polycyclic ring structures that are encompassed by the terms R ₁ and R j in the formula \, include the following:

UK

The ring-forming elements of A ₁₁ , A ₁₂ and A ₁ , independently of B ₁₂ and B ₁ , may contain from 1 to 11 carbon atoms in total, may contain from 1 to 10 carbon atoms and from 1 to 3 heteroatoms independently may be selected from M, O, S, P or other heteroatoms, or may contain 1 to 3 heteroatoms only under the condition that when one of the groups A ₁₁ , A. 2 and A _{1 is} a single heteroatom, the other two groups should contain two or more ring-forming atoms. A second condition is that the groups A ₁₁ , A ₁ J and A ₁ should contain at least two saturated ring-forming atoms when one or both of the groups B ₁₂ and B _{13 are} nitrogen.

Ring-forming he-fero atoms can, in certain cases, carry oxygen atoms, as in US Pat. Sulfinyl, sulfonyl, selenium oxide and phosphine oxide components. Selected, in A ₁₁ , A ₁ - and A .., containing carbon atoms may carry one or more Kar'bonyl-, thiocarbonyl, substituted or unsubstituted imino groups.

Bizyclic bridge structures included by E ₂ in the formula J _- may include any bicyclic bridge system of R ₁ and R with at least one nitrogen atom.

Illustrative bicyclic bridge structures included by R ₁ and R in the formula J_ include the following:

2

2

2

2

2

Z Z

Z

2 2

Z

2

2 z

Z Z

Z Z

Z Z

Z Z

Z Z

The substituent X may be an unsubstituted heteroatom such as, oxygen or sulfur, as in carbonyl and thiocarbonyl systems, or it may be a substituted heteroatom or carbon atom. X can also be a bivalent single or double bond. Further, X may be a saturated or unsaturated, branched or straight chain of carbon atoms; a branched or straight, saturated or unsaturated chain of atoms consisting of both carbon and heteroatoms; or it may be a branched or straight, saturated or saturated, all heteroatom-containing chain. Selected heteroatomic components of X can carry oxygen atoms, as in the case of groups containing sulfonyl, sulfinyl, N-oxide and phosphine oxide components. Selected heteroatom components of X may carry one or more of the substituents Z defined herein. Selected carbon atoms involved in X may carry carbonyl, thiocarbonyl, substituted or unsubstituted imino groups, substituted or unsubstituted alkylidene, or one or more of the substituents Z defined herein.

Illustrative structures included by the substituent X include the following:

8th ,

CO "R _fi CUHR _R K _Q j B M £>

λ Λ. A-, γ,

CN CCl, CF, O C (

λ, λ \ Λ ³ , Λ, Λ

-SO ₂ NR ₈ -,

Oil

ce

sr

Z Il

ae-ae

O I

cn

QC

1/1 I

CM O ΙΛ

Oil

t / l

Oil

OC

cn

^: v

oo

OC

cn

Coz-OC1 ·

wherein m is a value of 0 to 8, η is a value of O to and Rg ₉ Rg , R ^ q and R ^ independently represent hydrogen or substituted or unsubstituted alkyl, polyhaloalkyl, phenyl or benzyl wherein the permissible substituents are as herein are defined for Z.

From Formula I _- it will be appreciated that this includes a wide variety of heterocyclic, nitrogen containing compounds. Illustrative heterocyclic nitrogen-containing compounds within the scope of Formula 1 which can be used to reduce the moisture loss of plants by transpiration and to increase crop yields are given in Tables 43 to 43 below

 Table 1

Representative heterocyclic nitrogen-containing compounds

Representative Heterocyclic Nitrogen - Containing Compound; Representative Heterocyclic Nitrogen - Containing Compounds

"Ί

" '2

4-Cl

4-F

3.4-Cl ₂

4-CM ₃

4-CH ₃ O

3.4-Cl ₂

2,3-Cl ₂

2, S-Cl ₂

3-Cl

2-Cl

3, S-Cl ₂

4-CF ₃

4-C ₆ H ₅ O-

2-NO ₂

3-NO ₂

4-NO ₂

2,4-Cl ₂

0 ci Cl 0 Cl Cl 0 Cl Cl 0 Cl ci 0 Cl ci 0 Cl ci 0 Cl Cl 0 ' ci ci 0 Cl Cl 0 Cl ci 0 Cl Cl 0 ci Cl 0 ci ci 0 ci oi 0 Cl ci 0 Cl ci 0 Cl CJ 0 Cl OCH ₃

4-CO ₂ CH ₃ 4 -CH ₂ CO ₂ CH ₃

4-CH ₃ CO-

2,3.4,5, (- CI j

3-CH ₃ CONH

0 Cl ci 0 F F 0 Cl Cl 0 Cl Cl 0 Cl Cl 0 Cl Cl 0 Cl ci 0 Cl Cl 0 Cl Cl 0 Cl el 0 ci ci 0 Cl Cl 0 Cl Cl 0 Cl Cl 0 ci ci 0 ci ci 0 ci Cl

" '2

4- [C ₂ H ₅ CH (CH ₃ ) O] 0 Cl ci 3,4,5- (CH ₃ I ₃ 0 Cl ci 3,5- (CH ₃ ) ₂ -4-Br 0 Cl ci 2-Br-4-Cl 0 Cl ci 4-O.CH- 0 ct Cl 4-nC ₄ Hj0- 0 Cl ci 4-nC) H | ₅ O- 0 Cl Cl 4-Cl-5,6- (CHi) ₄ - 0 Cl Cl 3- (CH ₃ J ₂ N- 0 ci ci 4- (C ₆ H ₅ -NN-) 0 ci Cl 2,4-CI ₂ -I-COOH 0 ' . " Cl 4-C ₆ H ₅ 0 Cl Cl 3-F 0 Cl ci 2,4-Cl ₂ 0 ar br

Representative Heterocyclic Nitrogen - Containing Compound s Representative Heterocyclic Nitrogen - Containing Compound s Representative Heterocyclic Nitrogen - Containing Compound s

"Ί

R'l

" '2

J, 4-Cl ₂ O

4- (4-C ₂ H ₅ OC ₆ H ₄ NN -) - O 2,3- (CR-CH-CH-CH) -

2-CH ₃ 0-4-ally 1 0

2,4-CI ₂ 0

2,4-Cl ₂ D

3,4- (CH-CH-CH-CH) - 0

2,3- (CHj) ₄ - 0

2,3- (CH ₂ ) ₄ -4 Cl 0

2,3- (CH-CH-CH-CH) - 0

2.3- (CH.CH-CH-CH) -4-Cl- D

2,3- (CH-CH-CH-CHM-CH ₃ OO

4-Ct S

3-Cl S

2,6-Cl ₂ S

4-CH ₃ S

2.4-Cl ₂ S

Cl I ci Cl el Cl ci CH ₃ br CH ₃ Cl Cl Cl ci Cl ci Cl Cl ci Cl Cl ci ci Cl Cl ci ci Cl ci ci Cl Cl

4-CH ₃ O 5 4-F S 4-C1-2-CH1CH ₃₎ C ₆ H ₅ O 2-Cl NH 4-Cl NH 4-Cl NH 4- (4-01-2-BrC ₆ H ₄ O) -2-CH ₃ NH 2-CH ₃ -4- (4-Cl-2-BrC ₆ H ₄ O) -S-Cl NH 4-Cl NH 4-NO ₂ NH 4-NO ₂ NH

4- (c, H _r

Cl Cl Cl Cl Cl Cl Cl Cl ci Cl F F ci Cl

Cl

Br Cl Br

Cl

br

ci

3-nC ₄ H ₉ 0

-0-O-

3-C ₆ H ₅ -CH ₂ O-4- [4- (C ₆ H ₅ CH ₂ O) -C ₆ H ₄ CH ₂ BJ-

2-Br

2-CH ₃ (M-CHO 2. ₃ - (CH ₂ ), - 2,3-O-C (CH ₃ J ₂ O-3-CH ₂ -CHCH ₂ O-3-ClCH ₂ CH ₂ O-3 CH ₃ SO ₂ -O-2-CH ₃ O-

2-nC ₇ H ₁₅ O-

0 0

NH

Cl

Cl

Cl

Cl ci Cl ci ci ci ci Cl Cl Cl ci Cl Cl ci Cl Cl Cl ci ci Cl Cl Cl

Representative Heterocyclic ttttrogen - Containing Compounds Representative Heterocyclic Nitrogen - Containing Compounds Representative Heterocyclic Nitrogen - Containing Compounds

" ¹ I

2-C ₅ H ₆ CH ₂ O-

egg

Cl

_t 2-nC ₄ H ₉ 0-4 Br 0 egg Cl JIC ₃ H ₇ OS-Cl 0 Cl CI 2-C ₆ H ₅ SO ₂ -O- 0 , egg Cl J-CF ₃ CO ₂ - 0 egg egg 2-nC ₄ H ₉ CO- 0 egg Cl 2-C ₂ H ₅ OCO- 0 egg Cl 0 2-BrCH ₂ CH ₂ - 0 egg Cl J-CH ₂ -C (CH ₃ ) CH ₂ - 0 egg egg

»Ι« Ί

4-HO 0 Cl Cl 3-HO 0 Cl Cl 2-HO 0 ci Cl 4- (1-C ₃ H,) - 0 Cl Cl 3-C ₂ H ₅ - 0 ci Cl 3- (CHj) ₃ C- 0 Cl Cl 2-nC ₄ H ₉ - 0 Cl ci 2-SeC-C ₄ H ₉ - 0 Cl Cl j-Cl-4-nC ₃ H, 0 Cl Cl JC ₂ H ₅ -4-Br 0th ci Cl

CH,

3,4- (CH-CH-CH-CH) -

Cl

Cl

«-Fi

Cl Cl

Cl Cl

Cl Cl

ei ει

egg

Representative Heterocyclic Nitrogen - Containing Compounds Representative Heterocyclic Nitrogen - Containing Compounds Representative Heterocyclic Nitrogen - Containing Compounds

"Ί

X ', Y'i V ₂

"Ί

"Ί

Cl

Cl

4-11-C ₄ H ₉ S- O Cl Cl 2-1-C ₃ H ₇ S- O Cl Cl 3-nC, H ₁₅ S- O Cl Cl 4-HOCCH ₂ O- O Cl Cl 3-HClCCH ₂ O- O Cl ci 2-HCSCCH ₂ O- O Cl Cl 4- (C ₂ H ₅ SCH ₂ O) - O Cl Cl 3- (C ₂ H ₅ SCH ₂ O) - O ci Cl 2- (C ₂ H ₅ SCH ₂ O) - O Cl Cl 4- (C ₂ H ₅ OC-CH ₂ O) O Cl Cl

i - (/ » Vo-C-CH /)) -

2 - [(CH ₃ J ₃ COC-CH ₂ O-] 3,5- (CH ₃ O) ₂ 0 O 3.5- (C ₆ H ₅ CH ₂ O) ₂ 3,5- (CH ₃ COj) ₂ 0 2,6- (C ₂ H ₅ O) ₂ 0 2-C ₆ H ₅ - 0 3-C ₆ H ₅ - 0 3-C ₆ H ₅ -O 0 2-Cl-4-Br 0 2-C1-4-F 0 2.4-F ₂ 0 0 0

Cl

ci

Cl Cl

ci ci

Cl

ci

Cl Cl

ci

ci

Cl

ci

Cl

ci ci

Cl

ci ci

Cl

ci

Cl Cl

2-F-4-C1-2-NO ₂ -SC ₂ H ₅ 2.4- (NO ₂ J ₂ 2.5- (CH ₃ C) ₂

2,3,4-Cl ₃ 2 -CH ₃ O-CH ₂ -2,4- (C ₂ H ₅ C) ₂ O

4-C ₆ H ₅ SO ₂ -2.3- (CH ₃ ) ₂

3- (4-Cl-C ₆ H ₄ O) 2.3- (CH ₃ SO ₂ I ₂ 4. (2-01-4-BrC ₆ H ₄ ) 2-Cl-4-nC ₄ H ₉ O-

k;

NH NH NH

NH NH NH

NH NH NH 0

Cl Cl Cl Cl

Cl

Cl

Cl

Cl

Cl

ci

" '2

Cl Cl Cl

ci

ci

Cl

Cl Cl

ci

Representative Heterocyclic Nitrogen - Containing Compound s Representative Heterocyclic nitrogen - Containing Compounds

- Representative Heterocyclic Nitrogen - Containing Compounds

"Ί

"Ι

Η · </ Γ \ -ο) - ο

4-In-C ₄ H ₉ OCO-) 0

4- (Cf ₃ -CO-) 0

4 - [(CH ₃ J ₃ CCJ 0

egg

Cl

egg

egg

egg

egg

ei ει

Cl

egg

3-CH ₃ CO-

"Ί

Cl

Cl

" '2

Cl

egg

" ¹ I

" '2

2-Br-SDC ₄ H ₉ O- 0 Cl Cl 3-RC ₃ HjC-O Il Cl Cl 0 3- (CH ₃ OCO-] 0 Cl Cl 0 2-CH ₃ O - ^ - JCHj) ₃ C- 0 ci Cl 4-C ₆ H ₅ CH-CHCO- 0 Cl Cl 2,6-Cl ₂ - «- N0 ₂ O Cl Cl 4-CONH ₂ 0 Cl Cl 3-C ₆ H ₅ NHCO- S F F 4-CONHNH ₂ β ci ci 4-CH-C (CN) ₂ a Cl Cl

2-CH ₃ O-4-CH ₃ C (HO ₂ J-CH- 0 ci Cl 4-CH ₃ SO ₂ O Cl Cl 2-CH ₃ -4-Cl- 0 ci Cl 2-CH ₂ Cl-4-NO ₂ 0 ci ci 2.4-CU-3.5- (CH ₃ J ₂ - O . " ci 2-ClHg-4-N0 ₂ 0 ci ci 4-NO ₂ S ci ci 4- (CH ₃ J ₃ C- S ci ci 2,4-Cl ₂ -S-CH ₃ S ci ci 2,3- (CH-CH-CH-CH) - S Cl ci 4-C ₆ H ₅ O- S ci Cl 2,4-Cl ₂ S F F 2,4-Cl ₂ S br br 3,5-CLJ S Cl Cl 3-C ₆ H ₅ O- S F I 2,4-Cl ₂ O F F 2,4-Cl ₂ 0 br br

Representative Heterocyclic KUrogen - Containing Compounds Representative Heterocyclic Nitrogen - Containing Compounds Representative HeterocycHc Nitrogen - Containing Compounds

"Ί

3.5-Cl ₂ 0 Cl Cl 3-C ₆ H ₅ O- 0 f I 3- (4-Cl-C ₆ H ₄ CO-) S Cl ci 2-NO S Cl Cl

3- (4-Cl-C ₆ H ₄ CO-) 2-NO ₂

Cl Cl

Cl

Cl

ci ci

ci

4- (H ₂ N-COCH ₂ -) 4-CO ₂ (CH ₂ J ₁₁ CH ₃

-O)

4- (H ₂ NC-NH-)

2.4-Cl ₂ -5-CH ₃ 2-Cl-4-N0 ₂ 2 -CH ₂ OIM-Cl 2 -CH ₂ OCH ₃ 2 -CH ₃ C0-4-Cl

"Ί

Cl Cl

Cl ClR ¹ I

O Cl Cl O Cl Cl NH Cl ci NH Cl Cl NH Cl ci O Cl ci

-2.6-Cl ₂

»·, Y ¹ I V'2

ci ci

O Cl Cl

O Cl Cl

ο ci ci

S Cl Cl

3-CjH _n O-

2,3,5- (C ₂ H ₅ I ₃ -

Cl Cl

Cl

ci

Representative Heterocyclic Nitrogen - Containing Compounds Representative Heterocyclic Nitrogen - Containing Compounds Representative Heterocyclic Nitrogen - Containing Compounds

⁴ - [ ^CI

4-MC = I

X'l V, V ₂

egg

egg

egg

ci et

Cl Cl

^ Ci - ^^ - SO ₂ J- P -J

ci ci

O Cl Cl

Cl Cl

NH Cl Cl

ci ci

"Ί

X "

CH, -.

V-NHCNH-CH2 H-HHC-NH-I-II

O CH, O ^J

4-IcH ₁ O-CHCH ₁ OCH CH ₂ OI CH, CH, '' -

H (CH ₃ ) F

Br Br

Representative Heterocyclic nitrogen - Containing Compound s Table 2

Representative heterocyclic, nitrogen-containing compounds

Representative Heterocyclic Nitrogen - Containing Compounds

x, v,

X'2

'' 3

X'2

2-CH ₃ O-4-CO ₂ H

2,3,4,5,6-F ₅

3-CF3

2.4.5-Cl ₃

3-C ₆ H ₅

Cl Cl

Cl Cl

egg

ci ci

Cl Cl

Cl -O

0 F

Cl -O

ci

2,4-Cl ₂ O Cl CH ₃ 2,4-CLJ O br CH ₃ 2.3- (CH-CH-CH-CH) - O Cl CH ₃ 2,4-Cl ₂ O Cl CH3O

2.4-CLJ

Cl Pl-O) (OC ₂ H ₅₎ ;,

ci

2.4 CLJ-6-C0jH O Cl OCHjCF ₃ 2.4-CLJ O Cl CN 2,4-Cl ₂ O Cl SCH ₃ 2.4-CLJ O ci CCl ₃ H O ci CH ₃ CO- 2,4-CLJ O ci CH ₃ COCH ₂ - 2.4-Cl ₂ O Cl CF ₃ 2.4-Cl ₂ O Cl CH ₃ SOj 2.4-CLJ O ci -SCIN 2,4-CLJ O Cl H 2,4-CI ₂ O ci

Representative Heterocyclic nitrogen - Containing Compounds

, Hi ₁ Hetero ryric Witrons - Containing Compounds

Representative Heterocyclic Nitrogen - Containing Compounts

"I

' "3

'' 3

'' 3

'' 3

" '3

2.4-Cl ₂ 2,4-Cl ₂

2,4-Cl; 2,4-Cl ₂ 2,4-Cl ₂ 2,4-Cl ₂

2,4-Cl ₂ 2,4-Cl ₂ 2,4-Cl ₂ 2,4-Cl ₂ 2 -CH ₃ -4 (2-Br-4-Cl-C ₆ H ₃ O)

2,4-Cl ₂

0 Cl H 0 Cl -CsCH 0 Cl -CH-CH ₂ 0 Cl -C = CH 0 F -CsCH 0 Cl CHF ₂ 0 ci CONH ₂ 0 Cl -C-CH ₂ Cl S 0 Cl CH ₂ CO ₂ C ₂ H ₅ 0 F -N (CH ₃ J ₂ 0 Cl -P (.O) (OC ₆ H ₅ ) ₂ 0 Cl -OC n NH ci Cl NH ci CN 0 ci -Pf-O) (OC ₂ H ₅ I ₂

2,4-Cl ₂ 2,4-Cl ₂ 3-C ₆ H ₅ O-3-NO ₂

3-In-C ₉ H ₁₉ ) -

NH Cl 0 F 0 F NH F

ο - I o ei

α egg

oi

CN CH ₃ C ₂ H ₅ CH ₃

OCH ₂ CF ₃

CCl ₃

SO ₂ CH ₃

4-In-C ₇ H ₁₅ O) -

Cl

Cl

OSO ₂ CH ₃

OCF ₃

OC ₂ H ₅

SC ₃ H,

OCH ₃

Representative Heterocyclic Nitrogen - Containing Compounds Representative Heterocyclic Nitrogen - Containing Compounds

" '2

-R- \ η 1

i- \ «· - C, H _q S- / QV ^S ~

L - α - ·

1-1 HC = CCH ₁ O - (^ - S - I NH

* - O

-1

Ii J

«- C ₁ H ₁₁ NH-O ^ n-NH-

-S-I

* - \ CH, = CHCH, O- / OV ^NH -

rl

NH

-CH ₁ O-

OSO ₂ CH ₃ CF ₃

CCl ₂ Cl

Cl

NH F

SC ₂ H ₅

SCH ₃

CH ₂ CHF ₂

N (CH ₃ J ₃ OCF ₃

OSO ₂ CF ₃ OSO ₂ CF ₃

«H (OHO) -O-O-1-t-cH,

2,3- (CH-CHCH-CH) 2,4-Cl ₂

Cl

Cl

Cl

Cl Cl

CF,

OSO ₂ CH ₃ N (C ₂ H ₅ I ₃ ®

3U ₂ LII ₃ OCH ₃

CH ₃

OCH ₂ CF ₃ C ₂ H ₅ O

Table 3

Representative Heterocyclic, Nitrogen-Containing Compounds __ ^ _

Table 4

Representative heterocyclic, nitrogen-containing compounds

'' 3

'' 5

2.4-CI ₂ 0 CN CH ₃ 2,4-Cl ₂ 0 CN H 2,4-Cl ₂ 0 NO ₂ H 2.4-Cl ₂ 0 COCH ₂ Cl H 2.4-Cl ₂ 0 CN CN 4-C ₆ H ₅ O 0 OCH ₂ CF ₃ ' OCH ₂ CF ₃ 4-Cl 0 OCH ₂ CF ₃ OCH ₂ CF ₃ 4-Bt S OCF ₃ OCF ₃ 2,3- (OUCH-CH-CH) - S cci ₃ CCl ₃ 3.4- (CH ₂ ) ₄ 0 CF ₃ "3 3, S-Cl ₂ 0 OSO ₂ CH ₃ OSO ₂ CH ₃ J-KO ₂ 0 OSO ₂ CF ₃ OSO ₂ CF ₃ 3-C ₆ H ₅ CO NM OSO ₂ CF ₃ OSO ₂ CF ₃ 3,4- (CH.CH-CH-CH) - 0 OSO ₂ CH ₃ <= 2 "5 4-CH ₃ S 0 CN OSO ₂ CH ₃ 4-C ₆ H ₅ WH OCOCH ₃ OCOCH ₃ 3.4-Cl ₂ 0 SO ₂ CH ₃ SO ₂ CH ₃

" '6

"'11

H H H H H 0 1 Cl H CI H M 0 1 Cl H H H H 0 1 H CI H H M 0 1 H H CI H M 0 1 H ir H H H 0 1 H H br H H 0 1 F H H H H 0 1 H F H H H 0 1 H H F H H 0 1 H H 1 H H 0 1 H CI. egg H H 0 1 H Cl H CI H 0 1 Cl H H H CI 0 1 f H Cl H H 0 1 H H CH ₃ H H 0 1 H CH ₃ H H H 0 1

H H 0 H H 0 H H 0 H H 0 H H 0 H H 0 H H 0 H H 0 H H 0 H H 0 H . H 0 H H 0 H H 0 H H 0 H H 0 H H 0 U H 0

Representative Heterocyclic Nitrogen - Containing Compound ;

Τ «m Ίι η ^N CI

'' 5

1't

" '7

n ¹ »'10

"'12

CH ₃ H H H H 0 1 H H isopropyl H H 0 1 H H t-butyl H H 0 1 OCH ₃ H H H H 0 1 H OCN ₃ H H H 0 1 H H OCH ₃ H H 0 1 H H n-butyloxy H H 0 1 H "3 H H H 0 1 H H CF ₃ H H 0 1 H   H C ₂ F ₅ H H 0 1 H OCF ₃ H H H 0 1 H H OCF ₃ H H 0 1 H H OCF ₂ H H H 0 1 H OCF ₂ H H H H 0 1 H NO ₂ ' H H H 0 1 H H NO ₂ H H 0 1 H CN Ί H H 0 1

H H O H H O H H O H H O H H O H H O H H O H H O H H O H H O H H O H H D H H O H H O H H O H H O H H O

Representative Heterocyclic Nitrogen - Containing Compounds

% ν;

ILiO- -! In- JIn

H H CN H H 0 1 H SO ₂ CH ₃ H H H 0 1 H H SO ₂ CH ₃ H H 0 1 H H SO ₂ N (CH ₃ J ₂ H H 0 1 H H CO ₂ CH ₃ H H 0 1 H H N (CH ₃ J ₂ H H 0 1 H SCH ₃ H H H 0 1 H H SCH ₃ H H 0 1 H H C ₆ H ₉ SO ₂ H H 0 1 H H OCONHCH ₃ H H 0 1 H H DCOCh ₃ H H 0 1 H H OC ₆ H ₅ H H 0 1 H H CCGcF ₃ H H 0 1 H H CON (CH ₃ J ₂ H H 0 1 Cl H 'Cl H H 0 1 H H H H H 0 1 H H Cl H H 0 1

H H H H H H H H H H H H H H H H H H H H H H H H H H H H H CH ₃ H CH ₃ H CH ₃

ΑΤΑ

Representative Heterocyclic Nitrogen - Containing Compound s

v, V,

H H CN H H NO ₂ H H CH ₃ H H CF ₁ H H OCF ₂ H H K OCF _: r H H OCH ₃ H H H Cl H Cl Cl H Cl H H H H H Cl Cl H Cl Cl H F H H CH ₃ H NO ₂ H H H Noo

-JC.7- JLU- -Si J H H 0 1 H H 0 1 H H 0 1 H H 0 1 H H 0 1 H H 0 1 H H 0 1 H H 0 1 H H 0 1 H H 0 1 H H 0 1 H H 0 1 H H   ο 1 H H 0 1 H H 0 1 H H 0 1 H H 0 1

CH ₃

CH ₃

H'

H H H H H

CH ₃

CH ₃

CH ₃

CH ₃

CH ₃

CH ₃

CH ₃

CH ₃

CH ₃

sec-butyl

CF ₃

CF ₃

CF,

CF ₃ CF,

-AU-

0 0 0 0 0 0 0 0 0 0 0

0 0 0 0 0

Representative Heterocyclic Nitrogen - Containing Compound ;

Cl

A- -5-

iI ₇ - JLU-JtIJtlio- Jt ¹ U-

H CH H H H 0 1 H H CN H H 0 1 Ή H SO ₂ CH ₃ H H 0 1 H H H H H O ' 1 Cl H Cl   H H 0 1 H H H H H 0 1 Cl H Cl H H 0 1 H H H H H 0 1 Cl H Cl H - H O 1 Cl H H H H O 1 H Cl H H H 0 1 H H Cl H H 0 1 H br H H H 0 1 H H br H H 0 1 H Cl Cl H H 0 1 F H H H H 0 1

H CF ₃ 0 H CF ₃ O H CF ₃ 0 H C ₂ F ₅ 0 H C ₂ F ₅ 0 H CH ₂ CF ₃ O H CH ₂ CF ₃ 0 H CN 0 H CN 0 H CN O H CN 0 H CN O H CN 0 H CN 0 H cn 0 H CN 0

// 32nd

Representative Heterocyclic Nitrogen - Containing Compound s

Jtl4- -Ü5- JC *. -Ϊ17- JtIe- W ' _n H F H H H 0 1 H H F H H 0 1 H CH ₃ H H H 0 1 H H CH ₃ H H O 1 H H isopropyl H H 0 1 H H t-butyl H H 0 1 H OCH ₃ H H H 0 1 H H OCH ₃ H H 0 1 H H CF ₃ H H 0 1 H H OCF ₃ H H 0 1 H H OCF ₂ H H H 0 1 H H OCF ₂ CI H H O 1 H H SCH] H H 0 1 0 H H SCH ₃ H H 0 1 H H SO ₂ CH ₃ H H 0 1 H NO ₂ H H H 0 1 H H NO ₂ H H 0 1

Jt'u -Ili2l

H CN H CN H CN H CN H CN H CN H CN H CN H CN H CN H CN H CN H CN H CN H CN H CN H CN

JIt- 0 0 0 0 0 0 0 0 0 0 0

Representative Heterocyclic Nitrogen - Containing Compound s

ν; ν;

JLiS-

JE17-

JLl-JÜ9- JfIl

Jl'll- JL.12-

H CN H H H 0 1 - - H CN 0 H H CN H H 0 1 - - H CN O H H H H H O 1 • - - CH ₃ CN 0 Cl H Cl H H 0 1 - - CH ₃ CN 0 H H H · H H 0 1 - - CsH ₅ CN O Cl H Cl H H O 1 - - C ₆ H ₅ CN 0 H H H H H 1 1 H H H CN 0 Cl H Cl H H 1 1 H H H CN O H H H H H 1 1 H H H H O Cl H Cl H H 1 1 H H H H O H H , Cl H H 1 1 H H H H 0 H H NO ₂ H H 1 1 H H H H 0 H H CH ₃ H H 1 1 H H H H 0 H H OCH ₃ H H 1 1 H H H H O H H CF ₃ H H 1 1 H H H H 0 Cl H Cl H H 1 1 H H H CH ₃ 0 Cl H Cl H H 1 1 H CH ₃ H H 0 Cl H Cl H H 3 1 H H H H 0

/ 133

Representative Heterocyclic Nitrogen - Containing Compound s

Y ' ₇ JLLfl- ι »' η '

CT H H H Cl H H H H H H H H H H H H H H H H H H H H H Cl H H ^- H Cl H

Cl H H S 1 H H H 0 Cl H H 0 1 CI H H 0 1 CH ₃ H H 0 1 OCH ₃ H H 0 1 NO ₂ H H 0 1 CN H H 0 1 N (CH ₃ J ₂ H H 0 1 CF ₃ H H 0 1 OCF ₂ H H H O 1 OCF ₂ Cl H H 0 1 H H H 1 1 Cl H H 1 1 H .H H 0 1 Cl H H 0 1

IU JLLio- JL ¹ U- JtII ₂ H H H H - - H H - - H H - - H H - - H H - - H H - - H H - - H H - - H H - - H H - - H H - - H H H H H H H H H , H H H H CH ₃ H H H CH ₃

HH 0 1 - - HH Representative Heterocyclic nitrogen - Containing Compound s

JilS-

Jtl7-JLU

JLU-JLLlO- -I'll- JLLl2_

CH, '

OCH ₃

CF,

CN

H H

H H N (CH ₃ ) J H H 0 1 H H H H H 0 1 Cl H Cl H H 0 1 H H CH ₃ H H 0 1 H H OCH ₃ H H 0 1

H H H H H H H H H H

Jueu

Representative Heterocyclic Nttroqen - Containing Compounds

JIII.

JL.7- JtU- Jül. JLL -Ü9- JCiO- Jt ¹ Ii- -ϊΐιζ- Table 5 Representative heterocyclic nitrogen-containing impurities

JL.4-

H H CF ₃ H H 0 1 - - H H SO ₂ H H CN H H 0 1 - - H H SO ₂ H H NO ₂ H H 0 1 - - H H SO ₂ H H N (CHj) ₂ H H 0 1 CHj - H H SO ₂ Cl H Cl H H 1 1 H CH ₃ CH ₃ CH ₃ 0 H CF ₃ H H H 1 1 Cl CH ₃ CH ₃ H 0 H br H br H 1 1 - Cl C ₂ H ₅ H 0 H H H H H 0 1 C ₂ H ₅ - H H se NO, H H H H 1 0 H - - se

IU-1 H H Cl XLT ! U m * η · Cl H -OUCH-CIUCH- CK ₃ H H 0 0 H CH ₃ H Cl CH ₃ H 0 0 -UUCH-CIUCH- 4-CIC ₆ H ₄ O H H H 0 0 - (CNj) ₄ - 4-ClC ₆ H ₄ O C ₆ H ₅ COHH H H 0 0 N H H H 0 0 N C ₆ H ₅ O Cl H H 0 0 Cl Cl H H H 0 0 H -CN-CH-CH-CH- H H H 0 0 H CM ₃ C ₆ H ₅ H CH ₃ 0 0 H C ₂ H ₅ H Η ' 0 0 H Cl H H 0 0 H CH ₃ H H 0 0 C ₆ H ₅ O H H 0 0 H H 0 0

YV! Left! 111-! 111-

SU ! 111- Ii 4_ SO ₂ Cl Cl SO ₂ Cl Cl SO ₂ Cl Cl So ₂ Cl Cl SO ₂ Cl Cl SO ₂ Cl Cl SO ₂ 1 t SO ₂ I I So ₂ Cl .CHjO SO ₂ Cl CH ₃ SO ₂ Cl 1 so Cl Cl so Cl Cl so Cl Cl

so

Cl

Representative.Heterocyclic Nitrogen - Containing Compound s

IU H ₅ - -0-CH ₂ -O- IU H ₇ - Ha- "Ι η ". rs. HlO- HII HL 2- IU Hl3- hu H H C ₂ H ₅ H H H Ο O - - - - SO Cl Cl Cl H CH ₃ br H H O O - - - - SO Cl Cl H H H H H ^V H 1 1 H H H H So ₂ Cl Cl H H H C ₆ H ₅ O H H 1 1 H H H H SO ₂ Cl Cl Cl H H Cl H H 1 1 CH ₃ H CH ₃ H SO ₂ ci Cl H br H H 1 1 CH ₃ CH ₃ H H SO ₂ Cl CHj H H H H 1 1 H H H H so ci ci H CH ₃ H H 1 1 H H CH ₃ CH ₃ so ci CH ₃ H H H H 1 1 H H H H so ci I H CH ₃ CH ₃ H 1 1 H H H H so I I H CsH ₅ H H 1 1 H H H H so Cl I Cl br H H 1 1 CH ₃ H H H so Cl br

Table 6

Representative heterocyclic, nitrogen-containing compounds,

Ha HS_ IU Hi- IU  Ι -fi il H N H H ο β H H Cl H H 0 O Cl H Cl H H O O N N CH ₃ N H O O H N KH ₃ H N O α H H "3 N N O 0 H H NO ₂ H N O 0 H H CN H H O 0 H N H H H O O H H Cl H H O O Cl H Cl H H O 0 H H CH ₃ H H O 0 H H OCM ₃ H H O 0 H H CF ₃ H M O O H H NO ₂ H H O O H H CN H H O O H H H H H O 1 H H Cl H H O 1

IU- HiO- US

O S O S O S S S O S O S O S O S S S S S S S S S S S S S S S S S S S S S

AZb

Representative Heterocyclic Nitrogen - Containing Compounds

_ (χ · _{> ν} ί_ _χ ·, _0

H ₄ - H ₅ - H IU Cl OCH ₃ Cl H H H H H CF ₃ H H NO ₂ H H CN H H CH ₃ H H H H H Cl Cl OCH ₃ Cl H H H H NO ₂ CF ₃ H NO ₂ H H CN H H H H H H CH ₃ H H H H H Cl Cl Cl

Ü7- H H' J! ¹ - H ₉ - !! ίο- ϊ-15 "U- H H 0 1 - 0 S S H H 0 1 - 0 S S H H 0 1 - 0 S S H H 0 1 - 0 S S H H 0 1 - 0 S S H H 0 1 - ' 0 S S H H 0 1 - 0 S 0 H H 0 1 - 0 S 0 H H 0 1 - 0 S 0 H H 0 1 - 0 S 0 H H 0 1 - 0 S 0 H H 0 1 - 0 S 0 H H 0 1 - 0 S 0 H H 0 1 - 0 S 0 H H 0 1 - 0 S 0 H H 1 1 H H 0 S S H H 1 1 H H 0 S S H 1 1 H H 0 S S

Representative Heterocyclic Nitrogen - Containing Compounds

νίν;

π "- Ηί- Hi- Π7- Ηβ_ ι » ¹ η ' Ϊΐ9_ ϊΐιο- 4Is- Hl 5- X ' H H CH ₃ H H 1 1 H H 0 S S H H OCH ₃ H H 1 1 H H 0 S S H H CF ₃ H H 1 1 H H 0 S S H NO ₂ H H H 1 1 H H 0 S S H CN H H H 1 1 H H 0 S S H H H H H 0 1 - - NH S S H H Cl H H 0 1 - - NH S S Cl H Cl H H 0 1 - - NH S S H H CH ₃ H H 0 1 - - NH S S H H OCH ₃ H H 0 1 - - NH S S H NO ₂ H H H 0 1 - - NH S S H CN H H H 0 1 - - NH S H H H H H 0 1 - - 0 0 0 H H C ₆ H ₅ O H H 0 1 _ 0 0 0

Table 7

Representative heterocyclic, nitrogen-containing compounds ^

Ϊ14- Hs- IU Ϊΐ7. 11 * - JL. »17- ϊ-1 H H H H N 1 CO H H H Cl H H 1 CO H Cl H Cl H H 1 CO H H Cl Cl H H 1 CO M H Cl M H M 1 CO H H Ir H H H 1 CO H M H Ir H H 1 CO H H F F H M 1 CO H H H I H H 1 CO H F H Cl H H 1 CO H H H CH ₃ H H 1 CO H H CH ₃ H H H 1 CO H CH ₃ H H H M 1 CO H H N Isoprepyi ti ' H 1 CO H H H t-butyl H H 1 CO H OCH ₃ H M H H • ι CO H H OCH ₃ H H K 1 , εο H H H OCH ₃ H H 1 CO H

IU Ϊΐ5- Vt VJ Χΐβ- M ' Ü7- Χ116- H CF ₃ H H H 1 CO H H H CF ₃ H H 1 CO H H OCF ₃ H H H 1 CO H H H OCF ₃ H K 1 CO H H H OCF ₂ H H H 1 CO N H H OCF ₂ CI H H 1 CO H H NO ₂ H H H 1 CO H H H NO ₂ H H 1 CO H H CN H H H 1 CO H H H CN H H 1 CO H H H SO ₂ CH ₃ H H 1 CO H H H SO ₂ N (CH ₃ J ₂ H H 1 CO H H H SCH ₃ H H 1 CO H H H H H H • 1 CO CH ₃ H H CI H H 1 CO CH ₃ CI H CI H H 1 CO CH ₃ H H CH ₃ H H 1 CO CH ₃ H H OCH, H H 1 CO CH.

43 *

Representative Heterocyclic Hitrogen - Containing Comoound s

Ϊ14- Ϊΐ5_ Ϊ16- H NO ₂ H H CN H H H CF ₃ H H H H H Cl Cl H CI H Cl H H H OCH ₃ H CH ₃ H H H CH ₃ H H SCH ₃ H H CF ₃ H H OCF ₂ H H H OCF ₂ Cl H NO ₂ H H CN H H H H Cl H Cl

Ϊΐ7_ Ha- 1 Ϊ17- hu H H 1 CO CH ₃ H H 1 CO CH ₃ H H O CO CH ₃ H H 0 - COCH ₃ H H 0 - COCH ₃ H H 0 - COCH ₃ H H 0 '- COCH ₃ H K 0 - COCH ₃ H H 0 - COCH ₃ H H 0 - COCH ₃ H H 0 - COCH ₃ H H 0 - COCH ₃ H H 0 - COCH ₃ H H 0 - COCH ₃ H H 0 - COCH ₃ H H 0 - COCH ₃ H H 0 - COCF ₃ H H COCF,

Representative Heterocyclic Nitrogen - Containing Compounds

VJi- Γ-6- H H H Cl H Cl H H H H H Cl Cl H Cl CO ₂ CH ₃ H H H H CH ₃ H H OCH ₃ H OCH ₃ H NO ₂ H H H CN H H H "3 H H H H H ci Cl H Cl H H CH ₃ H H OCH ₃ H H "3

"L7 LLA re' Ϊΐ7- ϊΐτβ-  α S H H 1 CS H C H ' H 1 CS H J H H 1 SO ₂ H C H ' H 1 SO ₂ H conl H H 1 SO ₂ H S H H 1 SO ₂ H I H H 1 SO ₂ H H H 1 SO ₂ H "μ H H 1 SO ₂ H H H 1 SO ₂ H (U X H H 1 SO ₂ H ttve H H 1 SO ₂ H • 0 C α » H H 0 - SO ₂ CH ₃ O) Q H H 0 - SO ₂ CH ₃ £ H H 0 - SO ₂ CH ₃ H H 0 - SO ₂ CH ₃ H H 0 - SO ₂ CH ₃ H H 0 SO ₂ CH ₃

I U U U U U JO fti Λ * (V CXJ (M M

- I (Λ 1 / ϊ (O (Λ to (/ J

Table 8

Representative heterocyclic, nitrogen-containing compounds .

Representative Heterocyclic Kltroqen - containing compound «

N = N Table 9 ''

Representative heterocyclic nitrogen-containing compounds

IU Hs- H - Ht Hg H"_ Hs- H ₄ - Ht_ Ha- H M Cl H M H H SO ₂ CH ₃ H H H H Cl ₄ H H H H N (CH ₃ I ₂ H H Cl H H H H H H CO ₂ CH ₃ H H H Cl Cl H H OH H H CH ₃ H H Cl • r N M H H F H H H H CF ₃ H H H H CH ₃ H H H H H i H H H OCHj OCH ₃ H H H H SCH ₃ H H H H li fj i H H H CO ₂ M H H H H . H H K CN H H

SCH ₃

XU

Cl

Cl

Cl

IIS-H

M M H M M H H M H H H H

CN H

Cl

Cl

CH,

OCH ₃

CF ₃

SCH ₃

SO ₂ CH ₃

Cl

Cl

CH ₃

OCH ₃

CF ₃

Hi-H H H H H H H H H H Η H H H H

H-H H N H H H H M H H H H H H

'H H

SU

NH

NH

NH

NH

Xli7-O O 0 0 0 0 0 0 S S

0 0 0 0 0 S

Representative Heterocyclic Nitrogen - Containing Compounds

Xll «- H

H H H N H H H H H H

H H H H H

Cl

H ₄ -

ci

C ₆ H ₅ O

Ϊ.1- H

H ₈ -

NH

Table 10

Representative heterocyclic, nitrogen-containing compounds

Σα / 9 * Ν. ~ ._ ^ Σα Σι Σα single bond Y ¹ Σα Y "Y" Cl Σα. Σι Σα X ₁₂ H ^Υ 8 ' Cl H H H single bond H A ^Y 8 H H H Inclusion γ | Cl Σϊ Cl H H single bond 'H CP ₃ H H single bond Cl H H H H single bond H Σζ OCH ₂ H H H single bond H H H H H single bond H CP ₃ OCP ₂ cl H H single bond H H Cl H H single bond Cl H Cl Cl Cl Easy connection H CL br H H - single bond P H P P P single bond P H H H H single bond H H H H H single bond H H H H H single bond H Cl NO ₂ H   H single bond H H F H H Easy connection H P H H H single bond H F I H H single bond H NO ₂ CN H H single bond CH ₃ H H H H single bond H H SCH ₃ H H single bond H H H H H single bond H CN SO ₂ CH ₃ H H single bond H H CH. H H single bond H H N (CH ₃ J ₂ H  Η single bond H CH isopropyl H H single bond H H CO ₂ CH ₃ H H single bond H H t-rButyl H H single bond H H H H H CH ₂ OCH, H H H H single bond Cl H Cl H H CH ₂ H H H H H single bond H H H H H CH ₂ H H Ocho H H H H Cl H H CH_ OCH, H H Cl Cl

Representative Heterocyclic nitrogen - Containing Compounds Representative Heterocyclic Httroqen - Containing Compounds Representative Heterocyclic Nitrogen - Containing Compounds

.cl

.cl

IU Ϊΐ5- IL6 Υ.Ι7- ϊ-'β- "19- IU Ü5- ui- νίτ- IU "19- IU I ₅ - Ü6- ! 1τ_ IU "19- O H H br H H CH ₂ H H CN H H CHCN H NO ₂ H H H -CH-CH- CH ₂ C- H f H H H CH ₂ H H CF ₃ H H CHCN H CN. H H H -CH-CH- H H F H H CH ₂ H H H H H CHCO ₂ CH ₃ 0 F H Cl H H CH ₂ CI H egg H H CHCO ₂ CHj H H H H H -C- H NO ₂ H H H CH ₂ H H H H H -CSC- 0 H CN H H H CH ₂ H H Cl H H -CM- H H Cl ' H H -C- H H OCH ₃ H H CH ₂ Cl H Cl H H -CSC- 0 H CH ₃ H H H CH ₂ H H CH ₃ H H -CSC- Cl H Cl H H -C- H H CH ₃ H H CH ₂ H H OCH ₃ H H -CSC- 0 H H SCH ₃ H H CHj H H CF ₃ H H -CiC- H H CH ₃ H H -ί H H SO ₂ CH ₃ H H CH ₂ H NO ₂ H H H -CSC- ο H H NfCH ₃ J ₂ H H CH ₂ H CN H H H -CSC- H H OCH ₃ H H -C- H H H H H CHCN H H H M M -CH-CH- O 0 H H Cl H H CHCN H H Cl H H -CH-CH- H H CF ₃ H H -C- Cl H egg H H CHCH Cl H et η H -CH-CH- O H H CH ₃ H H CHCN H H CFJ κ ' H -CH-CH- H H N (CH ₃ I ₂ H H -C- H H OCH ₃ H H CHCN K H CH ₃ H H -CH-CH- H H NO ₂ H H CHCN H H OCH ₃ H H -CH-CH- H H H H H

Representative Heterocyclic Nitrogen - Containing .Compounds

IU Us-

Cl

CH ₃ OCH ₃

CH ₃

OCH ₃

Cl

H ₈ -

CHjC-0

-CCHj-

Σα H Σα Υ » Li γι ^Υ 8 X ₁₂ η: H OC ₆ H ₅ H H -C (CH ₃ ) ₂ - br H br H H -CH (C ₂ H ₅ ) - H H -0-CH ₂ -O- Ή -C (Cl ₂ ) - H -0-CH ₂ -O- H -C-C Il Il 0 0 H 0 0 Cl Cl H H -C-C H P H H H H -S-CHG = CH-CH-CH- 0 CH = -CH = CH-CH = H H H Easy connection H MO ₂ = CH- H H single bond H H H H H single bond H O ₆ H ₅ O- C ₆ H ₅ O- H H single bond H H H H H single bond H O ₆ H ₅ H H single bond

Y ¹ ih H H Σα Σι Σα Σι ^C 6 ^H 5 H H Cl H H H single bond -CH = CH-CH = CH- C ₂ H ₅ O H H single bond CH ₃ H H single bond Cl H H single bond

Table 11

Representative heterocyclic, nitrogen-containing compounds

iL & -10- H phenyl -C (CHj) -ho- 2,4-Cl ₂ phenyl -CH-HO- J.4-Cl ₂ phenyl -CH-HO- 4-IIOj phenyl -CH-HO- J-CH ₃ O-C ₅ M _n O phenyl -CH-NO 4-Cl phenyl -COCH NO- H phenyl -CH ₂ W) NHCH ₂ CH. *) - "-C1 Bhenyl -SCH ₂ C (CHj) -HO- 4-Cl phenyl -SII ₂ CH ₂ C (CHj) iodine H phenyl se 2,4-Cl phenyl se "Sr phenyl St Z-Cl-5-CH phenyl -PO (OCH ₃ ) - 3.4- (CH ₃ ) ₂ phenyl -Ph (O) - H phenyl -0-PO (OCHj) - H phenyl -SI (CH ₃ I ₂ - 4-CjH ₅ CONH phenyl -HH-SO ₂ - 4-chloro-l- -HH-SO ₂ naphthyl

Ϊ ^ Ο- 1 ^ 1- Cl Cl Cl Cl Cl egg Cl Cl Cl Cl Cl Cl Cl Cl Cl egg egg egg Cl egg Cl Cl Cl egg Cl Cl f f Cl Cl Cl Cl Cl egg Cl SC ₂ H ₅

Representative Heterocyclic Huourqen - Containing Compounds

Ϊ-10 phenyl -CSC- phenyl -CiC- phenyl c: c- 2-pyr1d1nyl -CJC- 2-pyrldlnvl -CH.CH- (ds) S-psridinyl -CH-CH- (trans)

F F Cl

Cl Cl Cl

OCH ₃ OCH ₂ CF ₃

Cl Cl Cl

-CH ₂ CH ₂ -

phenyl 0 3,4-Cl ₂ phenyl -NII-C- 0 i, 5- (CHj) ₂ phenyl -NH-C 3,4,5- (CHj) ₃ phenyl CO- 3-Cl CO-

Cl

Cl Cl Cl OC ₆ H ₅ 1 I

Table 11 (continued)

Representative heterocyclic, nitrogen-containing compounds

-CH ₂ CO-

1-naphthyl-NHO-

2,4-Cl ₂ phenyl H pehnyl

2-P-3-C1 phenyl 2,3- (CH = CHCH = CH) - phenyl 3-NO ₂ phenyl 4-C ₆ H ₆ "phenyl 2-Cl phenyl H phenyl

2,3- (CH = CHCH = CH; -phenyl

-S-S -S-S -S-S

br

Cl Cl Cl Cl

Single Bond Cl Single Bond Cl Single Bond Cl Single Bond Cl Single Bond Kin Compound Cl

21

Cl Cl Cl Cl CH CN CN -C = CH

Cl CCIn

A '

3,4,5- (CH ₃ J ₃ phenyl phenyl single bond Cl CH ₃ SO ₂ O H phenyl .Phenyl single bond Cl CP ₃ CH ₂ O 2-C ₆ H ₅ phenyl single bond P P 2,3- (CH-CHCH = CH) -phenyl phenyl single bond Cl -SO ₃ ⁶ W 4-CH ₃ phenyl -SO ₂ NHCONH- Cl Cl 2-Cl phenyl -SO ₂ NHCONH- Cl Cl phenyl / \ 3,4-Cl ₂ -CH-CH- Cl Cl 3-C H / ⁰ X -CH-CH- Cl Cl 3-NO ₂ -CH ₂ COCH ₂ Cl Cl 4-C ₆ H ₅ O -CH ₂ COCH ₂ Cl Cl

2,4-Cl ₂

H H H H

3-C ₆ H ₅

A ¹ phenyl

phenyl

^YI

-N-N-

20

Cl

Cl

Cl

Cl

Phenyl single bond OCH ₂ CP ₃ OCH ₂ CP ₃ 1-naphthyl single bond OSO ₂ CH ₃ OSO 1-naphthyl single bond CH ₃ phenyl -C = C- OCH ^ CP

CH

OSO ₂ CH ₃

T ¹ 3

oc:

-H ₂ CP ₃

1-naphthyl single bond CN phenyl single bond CN

Phenyl -CH ₂ N = CHC = C-Cl

Phenyl -CHONHCH ₀ C = C-Cl

-CH ₂ NHCH ₂ C = C-

CN H Cl Cl

Representative Heterocyclic Nitrogen - Containing Compounds

"1 "llO- CH ₃ phenyl -CH ₂ NCH ₂ CiC- CH ₃ phenyl -NH-CN phenyl -OCH ₂ CH ₂ O- phenyl -OCH ₂ - phenyl -OCH (CH ₃ ) - phenyl -OC (CH ₃ I ₂ - phenyl -OCH ₂ O-

H20

Cl Cl Cl Cl Cl Cl

Cl

Cl Cl Cl Cl Cl Cl

Table 12

Representative Heterocyclic Nitrogen-Containing Compounds _ ^ _ ^ __

Cl

Cl

OCH ₃

OCH ₂ CM,

OCH ₂ CM ₃

OCH ₃

phenyl

Table 13

Representative heterocyclic, nitrogen-containing compounds

gene

"Cl

EI10-

CH ₃

illl-CH ₃

CH ₃

t-butyl

CH ₃

CH ₃

Table Η

Representative heterocyclic, nitrogen-containing compounds

Representative Heterocyclic Hitrogen - Containing Compounds Table 15

Representative heterocyclic nitrogen-containing compounds;

Cj - ^ 3V C-OCW-O ^ ~~ ^ O CH,

-S- Cl

S-

OSO ₂ CH ₃ OSO ₂ CH ₃

OCH ₂ Cf ₃ Cl "Cl -» - "J)

Cl Cl

OCH ₃

Cl Cl-O-OJ) -O-

Cl Cl

- ° - \ uy " ^c ~ \ Ly ~ ° ~ ei ei Ih, -

Cl Cl

Ct CH ₃ SO ₂

eye Π <Γ ~ Ν1 trogen - Containing Compounds

"HO

ΪΛ2-

CI CI

-ο-

Cl Cl

-O-

-s

egg

Cl Cl

Table 16

Representative heterocyclic, nitrogen-containing compounds

Representative Heterocyclic Huourqen - Containing Compounds Representative Heterocyclic Nitrogen - Containing Compounds

13

10

Ul ΙΟ

Ü26- Ϊ127-! IiB-

-S

H CH ₃ CO

K S

-S-S- -KH-HH- -K-H-single bond

0 -CH.CH-

CH ₃ SOj-

CI Cl

Cl Cl

Cl Cl

Cl Cl

Cl Cl

Cl Cl

C! Cl

Cl Cl

Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl

«Lll- -C-

0 -C5C-

0 -CNH-

SO ₂ ϊΡ.Ο

OC ₂ H ₅

Flil- IUb-

Cl C!

Cl Cl

Cl Cl

Cl Cl

Cl Cl

Cl Cl Cl Cl Cl Cl

ΙΪ13

13

- "7Ϊ

-O-

-O-

Representative Heterocyclic Nitrogen - Containing Compounds Representative Heterocyclic nitrogen - Containing Compounds Representative Heterocyclic Nitrogen - Containing Compounds

Hi 3-

Ü29-

Ü30-

»130-

Cl

OCH ₂ CF ₃

C ₂ H ₅ SOj

br

BC ₁ H ^

-O-

CH ₁

ο o

-s ^ oys-

Il S ^ l / it O ο

-O-

OSO ₂ CH ₃ OSO ₂ CH ₃

-o-ci

n-C.H.0-

Cl

Cln-C / ί ,, Ο-

Il

-S-Il O

CCl ₃

-O- CH ₃ S

CCl ₃

CH

OCH ₃

Representative Heterocyclic Nitrogen - Containing Compounds Representative Heterocyclic Mt trogen - Containing Compounds Representative Heterocyclic nitrogen - Containing Compounds

Ϊ130-

-CH ₁ -

α-O-c.c-

α-O-ene

C ₂ H ₅ O-CtC-

Cl

Cl

-C-O

Cl

"S

-CiC-

Cl

Representative Heterocyclic Nitrogen - Containing Compound »

¹ HO

-S-NH-IIO

-C-NH-O

; c.Ho-

Hepresentatlve Heterocyclic Nitrogen - Containing Compounds

Eli 3-

Cl ₂ CH-O-

-CH.CHCN

-CH-CNCOCH ₃

-CH-CHCO ₂ C ₂ H ₅

-CO ₂ C ₆ H ₅

-NHCOC ₂ Hj

CH ₃ SO ₂ NH-

-CH ₂ CN

Cl Cl Cl Cl Cl Cl Cl Cl Cl

Ilao-

Cl Cl Cl Cl Cl Cl Cl Cl Cl

Table 17

Representative heterocyclic nitrogen-containing compounds _ __;

O O

Cl

Cl

Representative Heterocyclic Hitrogen - Containing Compounds

O O

Reference Heterocyclic nitrogen - Containing Compounds Representative heterocyclic mtrogen - Containing Compounds Representative Heterocyclic Nitrogen - Containing Compounds

o- O-. Q-

CI

SIL

O ₁

Cl

Cl o

ci o

CH, ¹

Cl

Cl

Representative Heterocyclic Nitrogen - Containing Compounds Representative Heterocyclic Nitrogen - Containing Compounds Representative Hetero

CH,

»132-

Xlai-

ct

"O

Table 18

Representative Heterocyclic Nitrogen-Containing Compounds ______ ^ _______

Representative Heterocyclic Nitrogen - Containing Compounds

CH ₁ CH

(6l

»132-Ct

A ',

2-pyridinyl-3-pyridinyl

ql

^L 33

Y '

34

A · X- ₂

^X '12

triple binding Cl Cl

Cl

Cl

NH

Cl

Cl

Cl

Cl Cl Cl

Table 18 (continued)

Representative Heterocyclic, Nitrogen-Containing Compounds ^

Representative Heterocyclic NUrogen - Containing Compounds

Y>

34

12

JLI

yi

LJL

Oil

single bond Cl

Sinfachbindung Cl

Sinfachbindung Cl

HH

Cl

Cl

Cl

Qj Sinfachbindung Cl Cl

Cl

Cl

Cl H ₁ COC ₁ H,

H ₁ F

Ill 2. XU3-

NH Cl Cl

NH Cl Cl

single bond Cl Cl

Cl Cl

Cl Cl

NH Cl Cl

Cl Cl

Representative HeterocvcUc Nitrogen - Containing Compound s Representative Heterocyclic nitrogen - Containing Compounds Representative Heterocyclic nitrogen - Containing Compound s

com

OCH,

Ill 2- Ü33-

Cl Cl

Cl Ct

Cl Cl

Cl Cl

Cl Cl

Cl Cl

Cl Cl

CM ₁

I " ¹

into]

CH>

«LlJ-Ü33- Ü34-

Cl Cl

egg

NH Cl Cl

SIH Cl Cl

NH Cl Cl

NH Cl Cl

NH Cl Cl

»12

^ CH ₁ -

P) "

Ϊ133. ΪΙ34-

NH Cl Cl

NH Cl Cl

Cl Cl

NH Cl Cl

Cl Cl

Cl Cl

Cl C1

Table 18 (continued)

Representative heterocyclic nitrogenous Verbindun gen

NH

MH

MH

MH

NH

"34

Cl

Cl

Cl

Cl

Cl

Single bond Cl

Single bond Cl

Cl

Cl Cl

Cl Cl

Cl Cl Table 18 (continued)

Representative heterocyclic, nitrogen-containing compounds

^l 33

12

Y '

33

Single Bonding Cl Single Bonding Cl

Single bond Cl Single bond Cl

NH

NH

Cl

Cl

Cl

Ch.

Cl Cl

Cl Cl

Cl Cl Cl

TABLE 18 [Cont. I Representative Heterocyclic Nitrogen - Containing Compounds

HN

NH

ti

Cl

Cl

IA IBt Cont.l Representative Heterocyclic Nitrogen Containing Compounds

Ali

Ϊ133-

NH

Cl

Cl

Cl

Cl

Cl

Cl

TA BLE 16 (Cant.) Representative Heterocyclic nitrogen - Containing Compounds

ro}

101

XIl 2_ ΪΙ33- Ϊ134-

Cl Cl

C) Cl

Cl Cl

Cl Cl

Cl Cl

Cl Cl

Cl Cl

Table 18 (continued)

Representative heterocyclic, nitrogen-containing compounds

^Y 33

34

12

Cl

Single bond Cl

Single bond Cl

Single bond Cl

NH

Cl

Single bond Cl

NH

Cl

Cl

Cl

Cl

Cl

Cl

Cl

Cl

cyclic Nitrogen - Containing Compounds

CH,

Cl C)

Cl Cl

Cl Cl

Cl Cl

Cl Cl

Cl Cl

Cl Cl

Representative Heterocyclic Nitrogen - Containing Compounds

O Cl Cl

Cl Cl

NH Cl Cl

CH ₂ Cl C)

O Cl Cl

α ei ei

CH ₂ Cl Cl

Table 19

Representative heterocyclic, nitrogen-containing compounds,.

Cl

CD"

SO ₂

Table 20 ·

Representative heterocyclic, nitrogen-containing compounds

(CH ₃ J ₃ pcs Cl Cl C ₂ H ₅ O- Cl Cl CH ₃ OC- Cl Cl D CH ₃ NH-CH (CH ₃ ) - Cl Cl (CH ₃ J ₂ C (OH) - Cl Cl

Cl

CH ₂ -CH-O- CI Cl (CH ₃ J ₂ NCH ₂ - Cl Cl (CH ₃ I ₃ SIOCH ₂ - Cl Cl

T ABLE 20 (Cont. ) Representative Heterocyclic Nitrogen - Containing Compounds

-Q-CH ₁ -

CH ₃ OCH ₂ --S-CH, -

CH ₃ SCH; - CI Cl CK ₂ -CH- Cl Cl CH ₃ -C- Cl Cl CH; HCiC (CH ₂ J ₅ - cl * Cl HC = C (CH;) ₄ - Cl Cl Cl-CH ₂ - Cl Cl Br-CH ₂ - Cl Cl HO-CH ₂ - Cl Cl CH3O-CH.CH- Cl Cl

Representative Heterocyclic Nitrogen - Containing Compounds

HIGH;);- Cl Cl C ₂ H ₅ CH (OH) - Cl Cl CH ₃ (CH ₂ I ₄ CH (OH) - Cl Cl

H ₂ NCH; - - Cl Cl (CH ₃ I ₂ NCH ₂ - Cl Cl (C ₂ Hs) ₂ IICH ₂ - Cl C! HCSCCH ₂ -NH-CH ₂ - Cl Cl (HCICCH ₂ ); N-CH; -Q Cl Cl CH ₃ -C- Cl Cl

Table 21

Representative heterocyclic, nitrogen-containing compounds. ;

Representative Heterocyclic Nitrogen - Containing Compounds

HO ₂ C- H Cl Cl C ₂ H ₅ OC- 1.-C ₃ H, - Cl Cl 0 (CH ₃ J ₃ C- Cl Cl Cl Cl Cl Cl

EIi 5-

-N-CCI ₂

-CH-NOH-NHCOCF ₃ -NHCOCH ₃ -CONH ₂ -CH ₂ CN-CH-CHCN-CH-CHCOCH ₃ -CH-CHCO ₂ CH ₃ -OCOC (H ₅ -NHCOC ₂ Hs-N (CH ₂ Cl) ₂ CH ₃ SO ₂ NH- (CH ₃ I ₂ N- (CH ₃ J ₂ N- (CH ₃ I ₂ CIlO- (CH ₃ I ₂ C.NO-

Ϊΐ39-

Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl (CH ₃ I ₂ N br br Cl Cl

Table 22

Representative heterocyclic nitrogenous Verbindun gen;

Table 23

Representative heterocyclic, nitrogen-containing compounds

5-C ₆ H ₅ O-

Rui »14 ill 4  Hai. IU3- ! Ut 2,4-Cl phenyl O H H Cl 2,4-Cl phenyl O Cl H H 2,4-Cl phenyl O H Cl H 3,5-Cl phenyl S H H Cl 2-CH3-4-, phenyl S Cl H Cl

4-C ₆ H ₅ - phenyl 0 H Br no 4-Cl phenyl 0 F -CH-CHCH-CH- 2,4-Cl ₂ phenyl 0 Cl -CH-CH-CH-CH- H phenyl 0 Cl Cl Cl

Ϊ145- * LS xiis- Ϊ146- "U7 1 H 2,4-Cl ₂ phenyl 0 Cl H H 2,4-Cl ₂ phenyl 0 Cl CH ₃ H 2.4-Cl ₂ phenyl 0 Cl Cl H 3,5-Cl ₂ phenyl 0 F F H 4-Cl phenyl S Cl Cl H 3.4-Cl ₂ phenyl 0 br br Cl 3,5-Cl ₂ phenyl 0 Cl Cl Cl ?. "- Cl _? phenyl 0 Cl Cl Cl H 1-naphthyl 0 Cl Cl Cl 4-C ₆ H ₅ O- phenyl S Cl Cl Cl H phenyl 0 Cl Cl

Table 24,

Representative heterocyclic nitrogen-containing compounds _:

Table 26

Representative heterocyclic nitrogen-containing compounds

3,5-Cl ₂

2,4-Cl ₂

3-C ₆ H ₅ O-

phenyl phenyl phenyl phenyl phenyl phenyl

O 0 0 O 0 S CH ₂

£ 49- £ .50- £ 51 Cl Cl Cl Cl Cl Cl Cl Cl Cl F F F br br br Cl Cl Cl Cl Cl CH ₃

£ 56- i a_! IL-IB £ S7 £ 5B £: 3-Cl phenyl 0 Cl H H 2,4-Cl ₂ phenyl 0 Cl H H 3.4-Cl ₂ phenyl 0 Cl Cl H 4-Cl phenyl S Cl Cl Cl 3.4- (CH ₃ I ₂ phenyl 0 F F F H 1-naphthyl 0 br br br 2.4-Cl ₂ phenyl 0 Cl Cl H

Table 25

Representative heterocyclic nitrogen-containing compounds

Table 27

Representative heterocyclic, nitrogen-containing compounds

* l52-

"in-

£ .53-

£ .54-

4- [CH ₃ CH (CO ₂ CH ₂ CH ₃ ) -] phenyl 0 Cl H Cl H phenyl -CH ₂ CH ₂ - Cl Cl Cl H phenyl 0 Cl Cl Cl

- * "Il9_ £ 60- £ 41- £ 42- * - phenyl 0 Cl H· Cl £ 59- phenyl 0 H Cl Cl 2,4-Cl ₂ phenyl S Cl H Cl 4-Cl-C ₆ H ₄ O- 2-CH3-4 Cl

Table 28

Representative heterocyclic, nitrogen-containing compounds.

Representative »HeteroocHc Nitrogen - Containing Compounds

tlti-

4- (4'-CK ₆ H ₄ O-)

4- (3 * .4'-Br ₂ C ₆ H ₃ HH-)

3- (2 ', 4'-Cl ₂ C ₆ H ₄ -)

1- (4'-O ₂ HC ₆ H ₅ -)

4- (2'-naphthaxy-)

3-C1 5-Cl.

3-H

i-Cl 4-CCl ₁

ti

"V ^ ³ · ⁵ - ° '2

χχ ....

4- (C ₆ HjO-C ₆ H ₄ O-]

F ₂ ! -CH ₃

4- (4'-Cl-C ₆ H, -)

5- (3'-C ₆ H ₅ OC ₆ H ₄ -)

4- (0'-ClC ₆ H ₄ -S

2.5-C1,

2.5-rj

2,4-Cl ₂

1- (4'-C ₆ H ₅ OC ₆ H ₄ O-]

3,4,5-Cl ₃ 4- [3-C ₆ H ₅ (CH ₂ ) J-]

2,5-Cl ₂

Representative Heterocyclic Nitrogen - Containing Compounds

A '"'

11 * 3

5- [3-O ₂ NC ₆ H ₄ -]

J ₁ S-Cl ₂ 1-C ₂ H ₅

5- [3'.4'-Cl ₂ C ₆ H ₃ O-]

, 2-f

4-CCl ₃ -IH-

4- [4'-Cl-C ₆ H ₄ CH 1 H-]

2,5-Cl ₂ 1-H

3-Cl 1-H

5- (C ₆ H ₅ CO-)

3-Cl 1-CH ₁

Representative Heterocyclic Nitrogen - Containing Compounds

1- [C ₆ H ₅ CH ₂ -]

3- [4-Cl-C ₆ H ₄ -]

S- (l-naphthoxy)

2- (2 ', 4'-Cl ₂ -C ₆ H ₃ O-)

2- [3'.4 '- (O ₂ N) ₂ C ₆ H ₃ -]

3- [3'.5''-Cl ₂ -C ₆ H ₃ -S-]

y ,,

ϊ ^ 3-3.5-F ₂

5-F S-Cl

5-f

Representative Heterocyclic Nitrogen - Containing Compounds

- [crt

5-C1

2- [l-naphthyl-C] XX 2- [4'-C ₆ H ₅ C-) 0 XX 0 2- [3'-O ₂ HC ₆ H ₄ SJ XX

5-Br

6- [3'-BrC ₆ H ₄ OI

Representative Heterocyclic Nitrogen - Containing Compounds

MC ₆ H ₅ SJ

Ü43- ϊΐί «-

1-H-9,7- (HO ₂ I ₂

& - [3 *, 4'-CI ₂ C ₆ H ₃ -]

4.5.7-H ₃

6 - [(1'-C ₆ H ₅ -C ₆ H, -)

2-Cl

5-NO ₂

4- [C ₆ H ₅ O-]

2-F

(-CH ₃ SO ₂

4- [4'-NO ₂ C ₆ H ₄ O-)

Ι- [3 ', 4 · .5'-CI ₃ -C ₆ H ₂ CH ₂ -)

2-C1

5.6,7-H ₃

4.5.6-H ₃

Representative heterocyclic nitrogen compounding compounds

GH

Table 29

Representative heterocyclic, nitrogen-containing compounds

ill 0 = ^ 20-

5- [2 x .4'-Cl ₂ C ₆ H ₃ -]

6-C ₆ H ₅ CH ₂ -

7- [4'-C ₆ H ₅ -C ₆ H ₄ ]

3-Cl

3-Cl

4,6,7-H ₃

4,6,7-H ₃

4-HO ₂ -5,7-H ₂

4,5,6-Hj

6- [2'.4'-Cl ₂ C ₆ H ₃ O-] 2-Cl. 4-Cl 3,5-H ₂ 0 0 0 5- [4'-ClC ₆ H ₄ -O-) 2-Cl 4-Cl 3-H 6-C1 0 4-C ₆ H ₅ O- 2-Cl 6-Cl 3,5-H ₂ 0 6- [4'-C ₆ H ₅ OC ₆ H ₄ O-] 2-F 4-F 3,5-H ₂ 0 6 ^ [2'.4 '- (O ₂ N) ₂ C ₆ H ₃ NH-] 2-F 4-F 3-H 5-CH3 0 4- [4'-ClC ₆ H ₄ S-] 2-F 6-F 3,5-H ₂ 0 5-C ₆ H ₅ CH ₂ - 2-Cl 4-Cl 3,6-H ₂ 0 4- (l-naphthoxy) 2-F 6-Cl 3, SH ₂ 0 4- [2'.6'-Cl ₂ -4'-pyridylnyl-S-] 2-Cl 6-Cl 3,5-H ₂ 0 6- [4'-C ₆ H ₅ OC ₆ H ₄ CH ₂ -] 2-F 3-F 4,5-H ₂ 0 5- [2'.4'-Cl ₂ C ₆ H ₃ O-) 2-Cl 3-Cl 4-H 1 4- [4'-C ₆ H ₅ OC ₆ H ₄ O-] 2-F 6-F 3,5-H ₂ ' 1 6- (3 ', 4'.5'-Br ₃ C ₆ H ₂ NH-) 2-F 5-F 3,4-H ₂ 1 6-C ₆ H ₅ -O- 2-Cl - 3-N0 ₂ -4.5-H ₂ 0 4- [3'.5'-Cl ₂ C ₆ H ₃ S] 2-F 3-CN 5.6-H ₂ ' 0 4- [2'.4'-Cl ₂ C ₆ H ₃ O-] 2-Cl - _{6-CCl3 -3,5-H?} 5- [3'-C ₆ H ₅ OC ₆ H ₄ O-] 2-Cl 6-Cl 3-CCI3-4-H

Table 30

Representative heterocyclic, nitrogen-containing compounds

Representative Heterocyclic nitrogen - Containing Compounds

5-C ₆ H ₅ SO ₂ 2-C1 4-Cl 6-Cl 0 5- (2.4-Cl ₂ C ₆ H ₃ ) SO ₂ - 2-Cl 4-Cl 6-Cl 0 4-C ₆ H ₅ S 2-Cl 3-Cl S-Cl 1 4-CF ₃ ^ -NO ₂ C ₆ H ₃ 2-Cl 4-Cl H 0 5- (4-ClC ₆ H ₄ ) SO ₂ - 2-Cl 4-Cl 6-Cl 0

H phenyl 0 Cl Cl 2.4-CLJ phenyl 0 Cl Cl 3,5-CLJ phenyl 0 Cl Cl 4-βΓ phenyl 0 Cl Cl 3-NO ₂ phenyl S Cl Cl J-CK phenyl 0 Cl 'Cl 4- (4'-ClC ₆ H (OJ phenyl 0 Cl Cl 4-Cl phenyl KH F F SC ₂ H ₅ , 2-pyrldyl NH C! Cl

O-

4-Cl 2.4-Cl ₂ H

1-naphthyl ο Cl

Phenyl CH ₂ Cl

phenyl single bond Cl

phenyl -CSC-Cl

Cl Cl Cl Cl

Table 31

Representative heterocyclic, nitrogen-containing compounds; , _

Table 32

Representative Heterocyclic, Nitrogen-Containing Compounds ___

Ϊ170-

S-Cl

4-Cl 2,4-Clj

H phenyl 0 Cl Cl 2.4-CLJ phenyl 0 Cl Cl 3,5-CLJ phenyl 0 Cl Cl 4-Br phenyl 0 Cl Cl 3-NO ₂ phenyl S Cl Cl 2-CN phenyl 0 Cl Cl 4- (4'-ClC ₆ H ₄ O) phenyl 0 Cl Cl 4-Cl phenyl NH f F 5-CjH ₅ J-P: rydyl NH Cl Cl

Cl

1-naphthyl 0 Cl

phenyl CHj Cl

phenyl single bond Cl

phenyl -CiC- Cl

Cl Cl Cl ClS Cl

5-C ₂ H ₅ H

5-Cl

* lis_

2.4-CLJ phenyl 0 Cl Cl 3.5-CLJ phenyl 0 Cl Cl 4-NOj phenyl 0 Cl Cl 4-CN phenyl 0 Cl Cl 3.5-Cl ₂ phenyl S Cl Cl 4-Cl 1-naphthyl 0 Cl Cl 3-C ₆ H ₅ O phenyl NH Cl Cl

phenyl

NH 0

Cl Cl

Cl

Cl Cl

Cl

2,4-Cl ₂ phenyl ^Y 73 ^A 15 NH Cl II ^f 75 4- (4'-ClC ₆ H ₄ O) phenyl 0 Cl Cl 4-Cl phenyl CHj Cl Cl γι 74 N Hi, '', NN

2,4-Cl ₂ .

ILTI

Phenyl single bond Cl phenyl -C = C- Cl

Table 33

Representative heterocyclic nitrogen-containing compounds

! L.76-

S-Cl

5-C ₂ H ₅

5-Cl

2,4-Cl ₂

Ü16-

"125-

H phenyl 0 Cl Cl 2.4-CI2 phenyl 0 Cl Cl 3.5-Cl ₂ phenyl 0 Cl Cl 4-NO ₂ phenyl 0 Cl Cl 4-CN phenyl 0 Cl Cl 3.5-Cl ₂ phenyl S Cl Cl 4-Cl 1-naphthyl 0 Cl Cl 3-C ₆ H ₅ O- phenyl NH Cl Cl

phenyl

Table 34

Representative heterocyclic nitrogen-containing compounds;

3, S-CIj phenyl O Cl Cl 4-ND ₂ phenyl O Cl Cl 4-CN phenyl O Cl Cl 2,4-Cl ₂ phenyl NH Cl Cl 2.4-Cl ₂ phenyl O Cl Cl 3-C ₆ H ₅ O phenyl NH Cl Cl 2,6-Cl ₂ phenyl -CK.NO- Cl Cl 3, S-Cl ₂ phenyl S Cl Cl 2-11O ₂ phenyl MH Cl Cl 2.3- (CH ₂ J ₄ phenyl O Cl Cl 2,4-Cl ₂ phenyl O f F 3.5-Cl ₂ phenyl α br br 2,5-Cl ₂ phenyl O f f 3, S-Cl ₂ phenyl> S br br 2-C1-2.3- (CH ₂ J ₄ - phenyl O Cl Cl 4- (4'-C ₆ H ₅ O- C ₆ H ₄ ) - phenyl O Cl Cl

A ·

16

phenyl

4- (4'-ClC ₆ H ₄ O) phenyl 0 4-Cl Phenyl 2,4-Cl ₂ phenyl

Cl

CH ₂ Cl

Single bond Cl -C = C-Cl

Υ ·

78

Cl Cl Cl Cl

R epresentative Heterocyclic Nitrogen Containing Compounds

3-C ₆ H ₅ O-4-CH ₃ O-5-C ₆ H ₅ O-2,4-Cl ₂

2,6- (C ₂ H ₅ I ₂

phenyl

phenyl

fc

/ COC ₃ H ₃

phenyl S 1-naphthyl 0 phenyl 0 1-naphthyl 0 phenyl S phenyl 0 3-pyr1d1nyl S

Cl Cl Cl Cl CN CN OSO ₂ CH ₃ OSO ₂ CH ₃ cci ₃ CCl ₃ CN OSO ₂ CF ₃ CN OCOC ₂ H ₅ OCH ₂ CF ₃ OCH ₂ CF ₃

-N® (CH ₃ I ₃ CN

3,4,5-Br ₃

phenyl

yrl1c NI trough »" - Containing compounds

XlBO-

phenyl 0 phenyl 0 phenyl 0 phenyl 0 phenyl 0 phenyl 0 phenyl 0 phenyl 0 phenyl 0 phenyl 0 phenyl 0 phenyl S phenyl 0 phenyl 0 phenyl O

< MO ₂ 0 -ν SO Cl OCC ₂ H ₅ ( Cl OCH ₃ Cl CN Cl OCH ₂ CF ₃ Cl SC ₂ H ₅ OCH ₂ CF ₃ SO ₂ CH ₃ OCH ₂ CF ₃ OCH ₂ CF ₃ CH ₃ S- Cl CCl ₃ Cl CH ₃ O- Cl Cl Cl F CH ₃ O- NO ₂ (CHj) ₂ N- Cl Cl Cl Cl Cl

Aft

IP

u'uu

uuu

O = O = CZL

• rH

60 • Η-ρrH

α Λ Ή <H OP

tu ο • Η Ρ ra

φ ο

CQ

O rl ω -ρ ω Φ > • rl -P in e \ • Ρ υ CD φ H CQ H (D

! η

, α ft Cl

Μ ω ω

EH CU bd

U-U υ

'O

I O

I

W = O

.ι

Representative Heterocyclic Nitrogen Containing Compounds

5ÜB2-

Cl Cl Cl Cl Cl Cl Cl C1 Cl. Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl

-NH-NH- -N.N- -S- -SO

-SO ₂

single bond -S-S-

-C: C -C -NH-

BIl 7- ILfl «. IUI

Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl

Cl Cl

Representative Heterocyclic NI troneη - Containing Compound s

ils2-

Bll7_

Cl Cl

  CO

Cl Cl

'CH ₃ COCl

Cl Cl

Cl Cl

CHP

Cl

Cl Cl

ⁿ -C, H, jC

Cl

Cl Cl

Cl Cl

-CH, O-

Cl Cl

Representative Heterocyc l ic nit rogen - Containing Compounds

Representative Heterocyclic Nitrogen - Containing Compounds

Cl Cl

Cl Cl

I) -C ₄ Hg Cl

Cl Cl N CH ₂ .CHCH ₂ - Cl Cl Cl Cl H CH ₃ O-CO- Cl Cl Cl Cl N CH ₃ SO ₂ - Cl Cl Cl Cl N CF ₃ SO ₂ - Cl Cl Cl Cl P Cl Cl Cl

Cl Cl P OC ₂ H ₅ Cl Cl Cl Cl P.O. Cl Cl Cl

"U2-Cl

Cl

Cl Cl

Ill. 7

CH ₃ O-Cl Cl

Cl Cl

Cl Cl

, Cl Cl

Cl Cl

Cl Cl

Cl Cl

Representative Heterocyclic Nitrogen - Containing Compounds Representative Heterocyclic Nitrogen - Containing Compounds

inland

SIl J_! Ü * 4_ ϊ ^ 5-

CI Cl

CH,

Cl Cl

-O

Cl Cl

Cl ClCl ClCl ClCl Cl Cl Cl

CHP

CHP;

O-

-O

O-

-O

Cl Cl

Cl Cl

Cl Cl

Cl Cl

Cl Cl

Cl Cl

Cl Cl

Cl Cl

Cl Cl -O-

Cl Cl

O-

Cl Cl

Cl Cl

Cl Cl

Cl Cl

Cl

OCOCH ₁

Native Heterocyclic Nitrogen - Containing Compounds

Representative Heterocyclic Nitrogen - Containing Compounds

"127-

8iw_ Hi 4-RIi 7-,

Cl Cl

-S

Cl Clci ci

Cl Cl

CHp

IHCNH-i (JVq-Ö

c, c, -o-pWrKOVo-

ci ci! LJI IvJJ IvJ

 O-

_ ₀

Cl Cl

Cl Cl

Cl Cl

Cl Cl

Cl Cl

Cl Cl

Cl Cl

Cl Cl

CH ₃ O Cl -O

-O-

-O-

Cl Cl

Cl · Cl

Cl Cl

Cl Cl

Cl Cl

Cl Cl

Representative Heterocyclic Nitrogen - Containing Compounds Representative Heterocyclic nitrogen - Containing Compounds

Cl Cl

-OCHCH, CHCHjP- / Q \ - _o _ CH ₁ CH ₁ ^ _Br

Cl Cl

Cl Cl

Cl Cl

Cl Cl

-CHC Hpc HC HJC CH ₁ CH,

-O-

Cl Cl

Cl Cl

MHCCHjCH / O

Cl Cl

CH,

CH ₁

_c , -OCCH-CH-O-C-CH-CH-O - ((I) -CH ₁ -

Ii Μ ι y-y *

O CH ₁ O CH ₁

Cl Cl

Cl Cl

-OCHjCH ₁ CO-ZQV-COO O

Cl Cl

Cl Cl

Cl Cl

-NHCHjCHjCCHjCHjCO-O

ο-

α Cl

Cl Cl

Cl Cl

Cl Cl

-OCHjCHjOCH ₁ CHP-ZQy ₀ _

Cl Cl

Cl Cl

Cl Cl

ο o

Cl Cl

Cl Cl

Cl Cl

Representative Heterocyclic Huourqen - Containing Compounds Table 36 Representative heterocyclic, 3ticksotffhaltise compounds

ν,

Cl ClCl ClCl ClCl Cl

Cl Cl

Cl Cl

CH ₁ Cl

CH, CH,

-O-C-CH-CH-O-C-CH-CH-O-OCH, (J CH,

-O-

O

CH ₁ O

Cl Cl -0-

CH ₂ CHiOC-NO

-O-

CH -

-S

-NHCH ^ H ₁ CCHJCHjCOHfO) -OO O ^ '

-O-

CH,

CH,

-O-

Cl Cl

Cl Cl

Cl Cl

CI CI

Cl Cl

Cl Cl

Cl Cl

Cl Cl

CH ₁ O-

HC ₉ H ₁₉ -

-CHJ

-CH.CH-CH.CH-

-CH ₁ O-

Representative Heterocyclic Nitrogen - Containing Compounds Representative Heterocyclic Nitrogen - Containing Compound s

Ilaa.

CH ₁

CH,

CI

Cl

Cl

Cl

Cl

Cl Cl

HCSCCH ₁ OO ^) - C (CH ₁ ), - Cl

-S

CH, = CHCHp - <(J> -S -

Cl

Cl

Representative Heterocyclic HUrogen - Containing Compounds Representative Heterocyclic Nitrogen - Containing Compounds

Ü28-

HCSCCHp-

CH ₃

ο o

Ii Vy β

O O

Re present

itive heterocyclic nitrogen - Containing compounds

Representative Heterocyclic Nitrogen - Containing Compounds

ϊ! ίβ_

Ϊΐβ6-

-NHC (CHi) ICNH-Ii O

^ OCHCHO-CHCH ₁ O-LUJ CH, CH ₁

CH ₁

-NHCNH-CH-CH-NHC-NH II I II

O CH ₁ O

CH ₃

SO ₂

Cl

"C.H.C-O-O

CH ₃ CH ₂ (CH ₂ ) JjCH ₂ -

CH ₃ OCH ₂ Ch ₂ OC-CH ₂ -CH ₂ CO

 0

Cl Cl

Cl

-CNHCHCH ₁ NHCHCH ₁ Nh-O CH ₁ CH ₁

CH ₁ Oi

CH ₁

H H

H H

Table 37

Representative heterocyclic, nitrogen-containing compounds,

18

H phenyl 0 Cl "-C1 phenyl 0 Cl 2.4-CI ₂ phenyl 0 Cl 3-CH phenyl 0 Cl 2.4- (CHj) ₂ phenyl 0 Cl 2-CH ₃ - «- C» phenyl 0 Cl 4-C ₆ H ₅ O- phenyl 0 Cl 3-C ₆ H ₅ CH ₂ O- phenyl 0 Cl 3.5-CI ₂ phenyl 0 ci 2.4.5-Br ₃ phenyl S Cl 2.4-Cl ₂ phenyl S Cl 3- (4-Cl-C ₆ H ₄₎ - phenyl S ci 4-C1 phenyl NH Cl 4-Cl phenyl NH F 3.4,5- (CHj) j phenyl NH F 3-C ₆ H ₅ O- phenyl NH F 3- «0 ₂ phenyl 0 F 3.4-Cl, phenyl CH. Cl

2,4-Cl ₂ phenyl single bond 0 0 Cl H phenyl single bond 0 -CH ₂ O- Cl 4- (C ₆ H ₅ O) - phenyl single bond 2-benzoxalyl-NH P 4-CF ₃ phenyl -COHH- 2-naphthyl Cl 3-Cl phenyl -C = C- phenyl Cl H 1-Haphthyl 0 Cl 4-Cl 1-naphthyl 0 Cl 5,6,7,8-H ₄ 1-Waphthyl 0 F 6-CH ₃ 3-pyridinyl 0 F 3-Cl 4-pyridinyl 0 Cl 5-Cl 2-thienyl Cl 3-Cl phenyl br H br H Cl 2,4-Cl ₂ Cl

Table 38

Representative heterocyclic, nitrogen-containing compounds

W-

"90

A '

18

3,5-Cl ₂

Phenyl Phenyl Phenyl Phenyl Phenyl Phenyl

2,4-Br ₂

4-CH ₃

3- (4-Cl-C ₆ HO) phenyl

3-C ₆ H ₅ O-phenyl

3-C ₆ H ₅ O-phenyl

2,4-Cl ₂ phenyl

2,4,5-Cl ₃ phenyl

4-CH ₃ O-phenyl

3,5- (CH ₃ O) ₂ phenyl

2-Br-4-Cl phenyl

3-C 1-4 -CH ₃ CH ₂ O phenyl -CH ₂ CH ₂

3-CH ₃ CH ₂ O-4-CH ₃ phenyl -COWH-

H 1-Waftyl 0

WH

WH

CH ₂

single bond

single bond

Cl Cl Br Cl Cl Cl

Representative Heterocyclic Nitrogen - Containing Compounds

2.4-Cl ₂

5,6,7,8-H

3,4,5-Cl

*! IE

"129-

2-naphthyl 0 Cl 3-pyridinyl -NH- F 2-tMenyl 0 Cl 2-thlazolyl -NH- F phenyl -CiC- Cl phenyl -CHjO- Cl phenyl -CH ₂ O- Cl 1-naphthyl 0 Cl phenyl CH, br

Table 39

Representative heterocyclic, nitrogen-containing compounds

^RI 18 ^At 18 phenyl ^XI 29 Y ' H phenyl phenyl 0 Cl 2,4-Cl ₂ Phenyl. phenyl 0 Cl 2,6-Cl ₂ phenyl phenyl 0 Cl 3-C ₆ H ₅ O- phenyl phenyl 0 Cl 4-C ₆ H ₅ CH ₂ - phenyl phenyl 0 Cl 3,4- (CH ₃ ) ₂ phenyl phenyl S Cl 3,5-Cl ₂ phenyl phenyl S Cl 4- (4-ClC ₆ H ₄ O) phenyl phenyl S Cl 2,4- (CH ₃ O) ₂ phenyl 0 Cl 3,4-CCH ₂ O- 0 Cl 2.3-0CH ₂ O- NH P 4-C1 NH P 3-WO ₂ 0 P 2-NO ₂ 0 Cl 3-CH ₃ CH ₂ 0 Cl H CH ₂ Cl H single bond Cl 3,5-Br ₂ single bond Cl

Representative Heterocyclic Nitrogen _R Containing Compounds

"LLB

2-CH ₃ - «- Cl

3-Cl4-Cl

"C14-CH ₃

5-Cl5-CH ₃

2.5-C1,

"I29-

phenyl chjo Cl phenyl ^CH 2 br phenyl chjo br 1-naphthyl 0 Cl 2-niphthyl 0 Cl l-naphthyl 0 Cl 2-pyrldlnyl 0 Cl 3-pyrtdlnyl 0 f 2-thlenyl 0 Cl 3-lsoxizolyl NH F phenyl -CSC- Cl phenyl D br

Table 40

Representative heterocyclic, nitrogen-containing compounds

ZJ

γ * * 91

^ i

^Z 2

(CH ₃ J ₂ CHCH ₂ CH ₂ - single bond 0

Single bond 0

Single bond 0

Single bond 0

CH ₂ = CHCH ₂

HC = CCH ₂

NH ₂ HO-

Single bond 0

single bond

Cl Cl Cl Cl

Cl 01

3i

Cl Cl Cl Cl

Cl Cl

Y '

 91

z *.

CHo (CH ₀ ) _1S O- single bond 0 H ₀ NC single bond 0

S (HIGHg) ₃ C- single bond 0

H ₀ NC single bond 0

0 OH ₃ OCH ₂ CH ₂ single bond 0

5-Brorao-2-

thiazolyl single bond 0

0 Cl Cl 0 Cl Cl 0 Cl Cl 0 Cl Cl 0 Cl Cl

Cl

R. ₉ -X. _o -N

91 92

2-pyridinyl single bond 5-bromo-2

pyridinyl single bond 6-methyl-4-

pyrimidinyl single bond 2-benzimida-

zolyl single bond 2- (2-indo-

IyI) ethyl single bond 2-thienylcarboxylic

boxamido single bond

Z '. 0

0 0 0 0 0

Z ',

0 0 0 0 0 0

y'r

Cl Cl Cl Cl Cl egg Cl Cl Cl Cl Cl Cl

zl

2-Benzoxa-

zolyl single bond 2-benzo

thiazolyl single bond 3-pyridinyl

methyl single bond 2-pyridinyl

methyl single bond 4-pyridinyl

methyl single bond 3-phenyl

2-propenyl single bond

Z '.

0 Cl Cl 0 Cl Cl 0 Cl Cl 0 egg Cl 0 Cl Cl 0 Cl Cl

Table 40 (continued) Representative heterocyclic sticks containing compounds

¹ 92

χ ·

' 1

phenyl

Ethynyl Efnfachbindung 0 4-Tolylsulfonyl

Single bond 0 3-phenylpropyl single bond 0

Single bond 0

Single bond O Single bond O

phenyl

2-phenyl

ethyl singlet bond benzenesulfonyl

Single bond benzyl single bond C ₂ H ₁ - single bond cyclohexyl single bond cyclohexyl single bond

O O O O

O O

Ignition,

Y ' Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl F F

br

O O CH, Cl O O Cl br O O. F Cl O O F Cl O O F H

DC ₃ H)

Cl '

Representative Heterocyclic Nitrogen - Containing Compounds

R ₁₁ -X ₁ , -!

single bond-CH ₂ CH ₂ --CH ₂ CH ₂ --CH ₂ CH ₂ -

4-nwthyl-2-th1szolyl

"-CHioro-J-benzothtazolyl -HH-

i'l

4S8

Representative Heterocyclic Nitrogen - Containing Compounds

Z '.

R ', 9

X'30

3-i-thyl-S-isoxazolyl-NH-

5-methyl-3-lsoxaiolyl

3-methyl-S-1soth1a {olyl-NH-

5-bromo-3-1soth1a Olyl!

5-ethyl-2- (1,3,4-th1 ad1azolyl) -NH-

3,5-d1methyl-2-pyr1in-1-yl-NH-

Representative Heterocyclic Nitrogen - Containing Compounds

O O

o ~

2-th1enyl

2-methoiyphenyl

'30.

-CH ₂

-CH ₂ -

- (CHj) ₃ -

- (CH ₂ ), -

-CH ₂ -

ClClCl

3,4-dichlorophenyl

phenyl

4-chiorophenyl

3-methyl-4-chlorophenyl

phenyl

TABLE 40 fCont.) Representative Heterocyclic Nitrogen - Containing Compounds

-CH ₂ -

CH -

sIngle bond

-CH ₂ -

ts ^Ä »·? (j

CH ₃

Table 40 (continued)

Representative heterocyclic nitrogen-containing compounds

R ¹ I ₉ & 30

1-methyl-

3-indolyl-CH (CH ₃ ) -

3-chloro-

phenyl -W (CH ₃ ) -

Z '.

Ignition,

O-

-CH ₂ single bond 0

Single bond 0

C ₂ H ₅ H 0 0 0 0 0

Cl

Cl Cl

Cl Cl

Cl

H Cl

2-furyl

CH -

CH ₃ N

Table 41

Representative heterocyclic, nitrogen-containing compounds

^RI 20 ^X> 31 ± \ i L21 LM LM _. 2,4-Dichlo- rophenyl single bond S Cl Cl Cl 2,4-Dichlo- rophenyl single bond CH ₂ Cl Cl Cl phenyl single bond CH ₂ E ¹ F 2,4-Dichlo- rophenyl single bond NH H H br phenyl single bond KCH, j? P i ¹ 4-Chloro- phenyl single bond KH Cl Cl Cl

^Y 95 * ' ₃ 1 Z ' ₃ Cl Vt LM .11 Cl 2,4-Dichlo- single bond HH Cl Cl Cl rophenyl -CH ₂ CH ₂ - 0 Cl Cl Cl phenyl -CH ₂ - S Cl Cl Cl phenyl -CH (CH ₃ ) - 0 Cl Cl Cl phenyl -CH ₂ - 0 Cl Cl phenyl OH = CH- 0 Cl Cl phenyl

phenyl -C = C- phenyl -S (= O) - phenyl -SO ₂ - Two-CThloro- phenyl -CH ₂ -

1-Hapthyl single bond

1-Haphthyl-

methyl single bond 0

W93

Lsi y 1 - 0 Cl Cl Cl 0 Cl Cl Cl 0 Cl Cl Cl IIH Cl Cl Cl 0 Cl Cl Cl

Phenyl single bond cyclohexyl single bond η-butyl single bond

0 0 0

Single bond 0

Single bond 0

4-phenoxy

single bond of phenyl

Cl

Cl

Cl

Cl

Cl

Cl

Cl

Y '

Lai

Cl Cl Cl

Cl

Cl

Cl

Cl Cl

Table 41 (continued) Representative Heterocyclic Nitrogen Containing Compounds;

3-phenoxy

single bond of phenyl

Cyclohexyl single bond

Cyclohexyli single bond

Phenyl - ^CH ₂ -

H ₄ 'single bond

H single bond

^Z> 3 Y ^'1 93 cm zsi 0 Cl Cl Cl 0 H H , br 0 F F F 0 H H Br. 0 br br OSO ₂ CH ₃ 0 H H OSO ₂ CH ₃

Phenyl phenyl phenyl

Single bond Single bond Single bond Single bond

Cyclohexyl single bond phenyl single bond

0 0 0 0 0 0

CH ₃

br

Cl

Cl

cm

br

OCH ₃

OCOCH ₃

Cl

Cl

OSO ₂ CH ₃ OSO ₂ CH ₃ OSO ₂ CH ₃ OSO ₂ CH ₃ OSO ₂ CH ₃ CN "95

phenyl

2,4-Dichlo-

rophenyl

phenyl

phenyl

phenyl

Single bond 0

4-methyl single bond 0 phenyl

Phenyl single bond 0

4-Morpholi-

nylmethyl single bond 0

4-aminophenyl single bond 0 4-kitro

phenyl single bond 0

single bond 0 Cl Cl OP (= S) (0C ₂ H ₅ ) ₂ single bond 0 Cl Cl SCH ₃ single bond 0 Cl Cl CF ₃ Introduction 0 Cl Cl OC ₂ H ₅ single bond 0 Cl Cl Cl single bond 0 OCTU Cl Cl

Vl Z21 Cl Cl " ¹ C ⁰ H Cl H j Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl

Table 41 (continued)

Representative heterocyclic, nitrogen-containing compounds

Z !, Γ 93

Phenyl hxenyl CH,

Single bond O CH ₀ ο

CH.

Cl Cl Cl

^: 93

^L 95

Single bond O Cl Cl Br

Single bond O 'SCH ₂ COIiHNHCSlJH H Cl · single bond ο PPQ]?

Cl Cl

Cl 'Cl

Br Cl

Pl TI ^R 20 ^X 31 ^z * 3 ^Y * 93 Υ '* 94 read 3-chloro-CH ₂ 0 Cl Cl Cl 2-pyridyl 2-3enzothia- zοIyI single bond 0 Cl Cl Cl 5-chloro 2-thienyl CH (CH ₃ ) - 0 Cl Cl Cl 5-methyl-3- isoxazolyl single bond 0 Cl Cl Cl 3,5-Dimethylr- 2-pyrirai- dinyl single bond 0 Cl Cl Cl 2-Fursrl CH ₀ 0 Cl Cl Cl

hj M 13 υ PO

ty · * ρ * ι ι ^

(D -1 ^ · (D Η3

H-

HS

(D

H H-

O O • β ty ρ · H (D O P hl O (- " ¹ O P " (D P

Hi iS ¹

I- ¹ O

O ^

O ί ^

B ro

(D P

et «<4

ty η V

I II

O Ω Ω

W W ffi Ω

tV) '-χΓΟ tB

vj

office

ω ω ω ω bd ω ω

H h H h h HH

W bd td td Κ K hl hi hl

Ω W H

κ κ κ κ

HJ

L-

103

Representative Heterocyclic Nitrogen - Containing Compounds

phenyl

cyclohexyl

n-propyl

2-chlorophenyl

phenyl

phenyl

2-methoxy-phenyl

-CONH-

-CH ₂ -

-CH ₂ -

-HH-

-CH ₂ -

-CH ₂ -

CH -

br

br

br

br

br

phenyl Einfa 3-Metlioxyphenyl -CH ₂ - 3-Pluorophenyl -CH ₂ - 3-Bromophenyl -CH ₂ - 2.Ethoxyphenyl -KH- n-propyl -CH ₂ - 2-Puryl -CH ₂ -

Cl

Cl

Cl

Cl

Cl

br

Y'Lsi γι Y " Cl H Cl Cl H H Cl H H H H H Cl H H H Cl H H , br H

Table 43

Representative heterocyclic, nitrogen-containing compounds

Representative Heterocyclic HI trogen - Containing.Compounds

2-norbornyl single bond Cl 3-pyridinyl -N (CH ₃ ) - r 5-1soKazoly1 -NH- F 2-naphthyl -CH (CH ₃ ) - Cl 3,5-dlchlorophenyl -CH ₂ CH, - Cl

Cl

Cl

Cl

Cl

Cl

H CH ₃ CHj CM ₃ CH ₃ CH ₂ It-C ₁ H ₉ CH ₃ benzyl CH ₃ CH ₂ 3-chlorobenjyi CH ₃ phenyl H "chlorophenyl BC ₃ H, pheno "y CH ₃ CH ₂ phenoxy CH ₃ CH ₂ l-naphthvi CH ₃

CH ₃ H

_COCH3 H

CH ₃ H

COC ₂ H ₅ CH ₃ Representative Heterocyclic Nitrogen Containing Compounds

XUO ₁ C OZi

Cl

'33

2,4-dichlorophenoxy CH ₃

3-pyrtdinylmethyl CH ₃ CH ₂

<-. chloroth1eny1oxy OH

OCH ₃

CO ₂ C ₂ H ₅

It can be seen that the particular compounds listed above in Tables 1 to 43 are examples of heterocyclic nitrogen-containing compounds which can be used to lower the transpiration water loss of plants and to increase crop yields according to the invention. The invention is not limited to the use of only these compounds, but the invention includes the heterocyclic nitrogen-containing compounds represented by the above-mentioned formula J_.

The novel heterocyclic, stannous-containing compounds of this invention can be represented by the following formulas:

(I)

woring:

R _{2 represents} unsubstituted or substituted phenyl, 1- or 2-naphthyl or heteroaryl;

X ₁₀ 0, S ,. SO, SO ₂ , HH, -CH ₂ O-, -CH ₂ S-, -CH (CH ₃ ) O-, -CH (CN) O-, -CH = KO-, -C (CHJ = NO-, -CH ₂ CH ₂ O-, -CH ₂ CH ₂ -, -C = C-, -CH ₂ SO-, -OCH ₂ CH ₂ O-. -CH (alkyl) - or -CONH-;

j is a value of 0 or 1;

a is a value from 2 to 4 inclusive and

Y.JQ is the same or different and is halogen, alkyl, cyano-polyhalocyl, alkoxy, polyhaloalkoxy, alkylthio, Al

kylsulfinyl, alkylsulfonyl, nitro group, acyl or polyhaloalkylsulfonyl, provided that (i) at least two ring-position pairs selected from 2 and 4, 2 and 6, 2 and 3 and 3 and 4 are substituted with the same or a different halogen are; (ii) R "/ is unsubstituted phenyl when ring positions 2, 4 and 6 are substituted with chlorine and J is 0 and X ₁₀ is SOg; (iii) R ₂ is not a phenyl unsubstituiertea when the ring positions 2, 3 and 5 are substituted with chlorine and 3, a value of 1 and X ₁₀ S is the same.

(Ii)

wherein:

Rpc represents unsubstituted or substituted phenyl, 1- or 2-naphthyl or heteroaryl;

X ₁₁ O, S, SO, SO ₂ , NH, CH ₂ , a single, bivalent bond, -CH ₂ O-, -CH ₂ S-, -CH (CH ₃ ) O-, -CH (CN) O- , -CH = NO-, -C (CH ₃ ) = NO-, -CH ₂ CH ₂ O-, -CH ₂ CH ₂ -, -C = C-, -CHgSO-, -CH ₂ SO ₂ -, - OCHgCHgO-, -CH (alkyl) - or -CONH-;

b is a value of 2 to 3, and

Y _{20 may be the} same or different and represents halogen, alkyl, cyano, polyhaloalkyl, polyhaloalkoxy, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, nitro, azyl or polyhaloalkylsulfonyl, provided that at least two of the ring-position pairs are those of 2 of Y ₂₀ Selected are halogen;

^L 22

(Iii)

wherein:

R ₂ g represents unsubstituted or substituted phenyl, 1- or 2-haphthyl or heteroaryl;

X ₁₂ O, S, SO, SO ₂ , HH, CH ₂ , a single, bivalent bond, -CH ₂ O-, CHgS-, -CH (CH ₃ ) O-, -CH (CN) O-, -CH = HO-, -C (CH ₃ ) = 110-, CHgCH ₂ O, CH ₂ CH ₂ , -C = C--, -CHgSO-, CH ₂ SO ₂ - represents -CH (alkyl) - or -COKH- ;

Y ₂₁ and Y _{22 are} independently the same or different halogens and

Y _{23 represents} hydrogen, halogen, alkyl, polyhaloalkyl, alkoxy, polyhaloalkoxy, cyano, alkylthio, alkylsulfinyl, alkylsulfonyl, kitro group, acyl or polyhaloalkylsulfonyl;

₂₇

(Iv)

γ y

^Y 26 ^X 25

wherein:

R ₂ "represents unsubstituted or substituted phenyl, 1- or 2-haphthyl or heteroaryl;

X ₁₃ O, S, SO, SO ₂ , HH, CH ₂ , a single, bivalent bond, -CH ₂ O-, -CH ₂ S-, -CH (CH ₃ ) O-, -CH (CH) O- , -CH = NO-, -C (CH ₃ ) = 110-, -CH ₂ CH ₂ O-, CH ₂ CH ₂ -, -C = C-, -CH ₂ SO-, -CHgSOg-, -OCH ₂ CH _{2 represents} O-, -CH (alkyl) - or -COHH-;

Y ". Represents halogen and

Ypc and Y "g independently represent hydrogen, halo, alkyl, polyhaloalkyl, alkoxy, polyhalo, oxy, cyano, alkylthio, alkylsulfinyl, alkylsulfonyl, hitro group, acyl or polyhaloalkylsulfonyl, provided that at least one of the two Y ₂ c and Y ₂ g is a halogen, and further provided that Rg ~ is not unsubstituted phenyl when Y ₂ -, Yg, - and Ygg chloro and X ₁₃ is equal to 0;

wherein:

^Y 29

(V)

R _{28 is} unsubstituted or substituted phenyl, 1- or 2-caphyl or heteroaryl;

X-. 0, S, SO, SOp, HH, CH ₂ , a single, bivalent bond, -CH ₂ O-, -CH ₂ S-, -CH (CH ₃ ) O-, -CH (CH) O-, -CH = HO-, -C (CH ₃ ) = WO-, -CHgCH ₂ O-, -CH ₂ CHg-, -C = C-, TCHgSO-, -CH ₂ , -OCHgCHgO-, -CH (alkyl) - or -CONH- represents;

and

are independently halogen, and

Ygq represents hydrogen, halogen, alkyl, polyhaloalkyl, alkoxy, polyhaloylkoxy, cyano, alkylthio, alkylsulfinyl, alkylsulfonyl, hitro group, acyl or polyhaloalkylsulfonyl;

^R 29 ^Χ Λ 5

(Vi)

wherein:

Rpg represents unsubstituted or substituted phenyl, 1- or 2-naphthyl or heteroaryl;

X 1 e, S, 30, SO ₂ , NH, CHg, a single, bivalent bond, "-CHgO, -CH ₂ S-, -CH (CH ₃ ) O-, -CH (CH) O-, - CH = HO-, -C (CH ₃ ) = WO-, -CH ₂ CH ₂ O-, -CH ₂ CH ₂ -, -C = C-, -CHgSO-, - CHgSOg-H ^ O-, - CH (alkyl) - or -COHH- represents and

L ₃ ^ uuiu. Y represent ₃₂ are independently hydrogen, halogen, alkyl, cyano group, polyhaloalkyl, alkoxy, Polyhaloalkoxy-, alkylthio, alkylsulfinyl, alkylsulfonyl, Hitrogruppe, acyl or Polyhaloalkylaulfonyl, provided that at least two of HaIogen are yoq »^ 31 ^ ¹ ^ ^ 32 ;

^R 3O ~ ^X 16 '

wherein:

unsubstituted or substituted phenyl, 1- or

2-naphthyl or heteroaryl;

X./j O, S, SO, SO ₂ , HH, CH ₂ , a single bivalent bond, -CH ₂ O-, -CH ₂ S-, -CH (CH ₃ ) O-, -CH (CN) O -, -CH = HO-, -C (CH ₃ ) = NO-, -CH ₂ CH ₂ O-, -CH ₂ CH ₂ -, -C = C-, -CH ₂ SO-, CH ₂ SO ₂ , -OCH ₂ CH ₂ O-, -CH (alkyl) - or -CONH represents and

Y-34 and

independently of one another represent hydrogen, halogen, alkyl, cyano group, polyhaloalkyl, alkoxy, polyhaloalkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, hitro group, acyl or polyhaloalkylaulfonyl, provided that (i) at least two of Y ₃₃ , Y ₃ . and Y ₃₁ - are halogen, (ii) R _{30 is} not unsubstituted phenyl when Y is ₃ . and Y ₃ C are both chloro and X ₁ g is 0, and (iii) R ₃ Q is not unsubstituted phenyl or 4-methoxyphenyl when Y-, ·, and Y- ,. both are chloro and X ₁ / - is equal to 0.

(Viii)

wherein:

d is a value from 0 to 4 inclusive,

e is a value of 1 or 2, provided that d and e are not greater than 5 sirid;

Rt is the same or different and is unsubstituted or substituted aryl, provided that d is not 0 when R ₃₁ is 2- or 4-A _r yl, aralkyl, provided that d is not 0 when R ₃₁ R -Aralkyl, an alkoxy, cycloalkoxy, aryloxy, araikoxy group, provided that d is not 0, when R ^ _{1 is} a 4-aralkoxy group, an arylaryloxy group, aralkoxyaralkyl, arylaralkoxy group, aryloxyaralkyl, aryloxyalkyl, aryloxyaryloxy group, aralkoxyaralkoxy, Aryloxyalkoxy, allylthio, alkenylthio, arylthio, aralkylthio, arylthioaralkyl, arylsulfonylarylsulfonyl, alkylamino, dialkylamino, azyloxy, aroyloxy, alkoxycarbonyloxy, phenylazo, provided that Χ ^ γ is 0 or S, a haphthylazo group or -OCHgO- or -OCHgCHgO connecting adjacent carbon atoms to form a five- or six-membered ring;

Y ₃ g is the same or different and halogen, alkyl, alkenyl, alkynyl, -CH = CHCH = CH-, the adjacent carbon atoms to

Combine formation of a six-membered ring, - (CH ₂ ) * »represents mitro, cyano group, haloalkyl or polyhaloalkyl;

X _{17 represents} 0, 3, NH, CH ₂ , -CH ₂ O-, -CH ₂ S- or -OCH ₂ CH ₂ O-; , Υ-, γ represents halogen and

Y., g represents halogen, alkoxy, alkylthio, alkylsulfonyl, polyhaloalkoxy, polyhaloalkyl, cyano, nitro or unsubstituted or substituted arylthio, aryloxy or arylsulfonyl;

(Ix)

40

wherein:

f is a value from 0 to 5;

R 32 is identical or different and is halogen, alkyl, alkenyl, alkynyl, polyhaloalkyl, cyano, mitro, alkylamino, dialkylamino, alkoxy, polyhaloalkypoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, polyhaloalkylsulfonyl, acyl, C0 ₂ (alkyl), COMH (alkyl), COK (alkyl) ₂ , SO ₂ N (alkyl) ₂ , alkylcarbonyloxy, alkoxycarbonyloxy or unsubstituted or substituted aryloxy, arylthio, arylsulfonyl or aroyl;

Lg 0, S, CH ₂ , a single, bivalent bond or -C = C-;

Y, q represents halogen, polyhaloalkoxy group, polyhaloalkyl, cyano group, alkylsulfonyl, alkylsulfonyloxy group, polyhaloalkylsulfonyl or polyhaloalkylsulfonyloxy group, and YQ represents haloalkyl, polyhaloalkyl, alkoxy group, provided that X ₁ Q is not S or a single divalent bond, polyhaloalkoxy, cyano, alkylthio group, provided that X ^ q is 0 or a single divalent linking, alkylsulfonyl, Hitrogruppe, Dialkoxyphoaphinyl or ammonium Trialky!;

^L 42

(X)

worxn:

Y.sup.1 is the same or different and is halogen;

Y.P is the same or different and represents halogen, alkoxy, alkylthio or polyhalalkoxyl group and

X ₁₉ 0, dithio group, -P (= O) (O-alkyl) -, -P (alkyl) -, P (O-alkyl) -, sulfinyl, sulfonyl, thiosulfinyl, a single, bivalent bond,! Carbonyl, aminocarbonylamino -, Arminooxalylatnino », aminocarbonylalkylenecarbonylamino, aminoalkyleneamino, ungrafted or substituted oxyaryloxy group provided that 1,3-arylenebis (oxy) is substituted by at least one substituent, oxyarylalkylaryloxy, oxyarylthioaryloxy, oxyarylsulfonylaryloxy and oxyarylaryloxy group;

• 52

* X 20 "

(Xi)

wherein:

Υ, -ο and Yno are independently halogen;

g is a fourth from 0 to 5 inclusive;

R, - are the same or different and are halogen, alkyl, alkenyl, alkynyl, polyhalosyl, cyano, tristro, amino, alkylamino, dialkylamino, alkoxy, polyhaloalkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, polyhaloalkylsulfonyl, alkoxycarbonyl, Alkylaminocarbonyl, aminocarbonyl, dialkylaminocarbonyl, dialkylaminosulphonyl, alkylaminosulphonyl, aminosulphonyl, alkylcarbonyl, dialkalkylalkyl, alkylcarbonyloxy, alkylcarbonylalkylamino, -CH = CHCH = CH- linking adjacent carbon atoms to form a six-membered ring, or unsubstituted or substituted aryl, aralkyl, aryloxy, Arylthio group, arylsulfonyl or aralkoxy group, and

X _{20 represents} -CH (alkyl) O-, -C (alkyl) ₂ O-, OCHg-, -CHgO-, -CHg-, -C (halo, -OCHgO-, -OCHgCHgO- or -O = G- , provided that g is at least 1, -OCH (alkyl) -, -OC (alkyl) ₂ , -OCH (alkyl) O-, OC (alkyl) gO-, -OCH (alkyl) CHgO-, -OCH (Alkyl) CH (alkyl) O-, -CH (alkyl) CH (allyl) -, -CH (alkyl) -, -C (alkyl) g-, -CH ₂ CH ₂ O-, -OCH ₂ CH ₂ - , -CH (alkyl) CH ₂ O-, -CH ₂ CH ₂ -, -CH (CK) O-, -C (alkyl) (CW) O -, -CH (polyhaloalkyl) O-, -C (CW) - WO-, -C (WH-alkyl) = H0-, -C / w (alkyl) ₂ 'J = W0-, -C (S-alkyl) = WO-, -C (O-alkyl) = HO-, -SC (= O) O-, -WHC (= O) O-, -W (alkyl) C (= O) O-, SO, SO ₂ , CHgS (O) _h -, -CH (alkyl) S ( O) _h -, -S (O) _h CHg-, -OC (= S) S-, -C (= O) S-, -C (= S) -S-, -WH (alkyl) C (= O) S, -O (C = O) S-, -H (R 1) - -SO ₂ WH-, -SO ₂ W (alkyl) -, -COWH-, -COH (alkyl) -, -SC (= O) W (A1-kyl) -, -SC (OO) HH-, -WHSO ₂ WH-, -W (alkyl) SO ₂ W (alkyl) -, H (alkyl) SO ₂ HH- HHSO ₂ W (alkyl) -, -C (O-alkyl) = W-, -C (S-alkyl) = W-, -CH (halo) -, -C (alkyl) (halo), -CH (CW ) -, -C (alkyl) (CW) -, -KH (alkyl) HH-, -HH-H (alkyl) -j-WH-WH- or -W = H-, provided that that R _{33 is} not a Hitro group; -C (= O) -, -C (= O) C (= O) -, -CH (O-alkyl) -, -CH ₂ C (= O) -, -C (= O) CH _2> - CH (alkyl) C (= O) -, -C (= O) CH (alkyl) -, -CH = CH-, -C (alkyl) = CH-, -CH = C (alkyl) -, -C ( Alkyl) = C (alkyl) -, -C (= O) CH = CH-, P (Y ₄₃ ) Y ₄₄ alkyl) -, unsubstituted or substituted -P (Y ₄ ) (Y ₄₄ - aryl) or arylene , 3i (halo) ₂ -, Si (alkyl) ₂ -, -Oc (= O) H (alkyl) -, -OCH ₂ C (= O) H (alkyl) -, -H (alkyl) COW (alkyl ) -; -OC (= O) WH-, -WHCOHH-, -SO ₂ KHC (= 0) KH- or -WHC (= 3) HH, provided that g is at least 1; -CH-CH-, -C (alkyl) -CH-,

HCH

Represents -CH-C (alkyl) or -C (alkyl) - £ (alkyl) -,

b-

wherein h is a value from 0 to 2 inclusive, R _{34 is} azyl, alkylsulfonyl, polyhaloalkyl, polyhaloazyl, polyhaloalkylsulfonyl or unsubstituted or substituted aroyl or arylsulfonyl-id; and Y ₄₃ and Y _{44 are} O or S;

wherein:

35 ^Λ

Uli)

R _{31 represents} an unsubstituted or substituted heterocyclic ring system selected from isoxazole, ^. Isothiazole, pyrazole, imidazole, 1,2,4-triazole, 1,2,4-oxadicarbazole, 1,3,4-oxadiazole, 1,2,4-thiadiazole, 1,3,4-thiadiazole , Oxazole, thiazole, benzopyrazole, benzimidazole, benzoxazole, benzothiazole, indole, pyrrole, furan, thiophene, benzofuran, benzothiophene, pyridine, pyrimidine, pyridazine, pyrazine, 1,3,5-triazine, 1,2,4-triazine, quinolene , Isoquinoline, quinazoline, phthalazine, benzopyridazine, benzopyrazine, carbazole, dibenzofuran, dibenzothiophene, benzoxazine, phthalimide, benzopyran, dibenzopyridine, pyridopyridine, pyrazolopyrimidine, tetrahydropyrimidinedione, coumarin, piperidine, morpholine, tetrahydrofuran, tetrahydrothiophene, pyrrolidine, thiomorpholine, piperidin-2-one , Piperidine-2,6-dione, 2,5-pyrrolidinedione, 3-morpholine, 2-oxohexamethyleneimine, 2-oxotetralethyleneimine, 1-pyrazoline, 2-pyrazoline, pyrazolidine, 2-imidazolidinone, 2-imidazolidinethione, 2,4-imidazolidinedione , 1,2-oxathiolane, 1,3-oxathiolane, 1,3-oxathiane, 1,4-oxathiane, 2- (1H) -pyrazinone, 2H-pyran-2-one, 4H-pyran-4-one, 2H Pyran-2-thione, 4H-pyran-4 thion, tetrahydropyran, tetrahydrothiopyran, 7-oxabicyclo [2.2.i] heptene, 7-azabicyclo [2.2.ijhepten, oxetane, coumarin, 1,3-dioxane, 1,4-dioxane or 1,3-dioxolane;

X _{21 represents} O, S, or NH, provided that R ₃ , - is not pyridine when X 1 is WH, and that R ₃₁ - is not unsubstituted benzothiazole when X pi is S, and

Y ₄ , - and

are independently halogen;

3J.

Π if

47

wherein:

R-JY and R-jg independently represent halogen, nitro, cyano, polyhaloalkyl, polyhaloalkoxy, alkylsulfonyl, polyhaloalkylsulfonyl, acyl, alkoxycarbonyl, polyhaloalkylsulfonyl or R ₃₉ ~X ₂ 2 ~, provided that only one of R ₃ , and R ₃₈ R ₃ QX ₂₂ ^{may be} "Rjq unsubstituted or substituted phenyl, 1- or 2-naphthyl or heteroaryl;

X ₂₂ O, S, SO, SO ₂ , CH ₂ , a single, bivalent bond, -OH ₂ O-, -CH ₂ S-, -CH (CH ₃ ) O-, -CH = NO-, -C ( CH ₃ ) = 110-, -CHgCHgO-, -CH ₂ CH ₂ -JC = C-, -CH ₂ SO-, -CH ₂ SO ₂ -, OCHgCHgO-, -CH (alkyl) or -CONH;

Y _{47 represents} halogen and

B ₁₄ 0, S, NH or NR. _Q is wherein R _{40 is} alkyl, alkylsulfonyl, alkenyl, alkynyl, alkoxycarbonyl; unsubstituted or substituted aryl, aralkyl, aryloxy, arylaraino, aroyl or arylsulfonyl; provided that (i) both R ₃₇ and R ₃₈

_{37 38} other than R ₃₉ -X ₂₂ ^{are when} B ₁₄ R ₃₉ -NC, R ₃₉ -AlkVl-Nr, R ₃₉ -C (= 0) -H £, R ₃₉ -SO ₂ Ni, R ₃₉ -ON ^

is; one of R ₃₇ and ^R ₃ 8 ^R 39 ~ ^X 22 ~ ^is » ^{when B} H ^{et W (} * ^{s on} " is other than R ₃₉ -N-, R ₃₉ -AllySi-N *, R ₃₉ -Ci = O) - Ni, R ₃₉ -SO ₂ NS, R ₃₉ -ON - or R ₃₉ -NH-N * (ii); and (iii) R _{39 is} not unsubstituted phenyl when R ₃₈ and Y _{47 are} both chloro and X "p is a single divalent bond in the formula (xiii);

or

^ 42

1 ^Β 15 ^Η 42

(Xvi)

wherein:

R ₄₁ and R ₄₂ are independently halogen or R ₄₃ -X ₂₃ -darstellen, provided that only one of R and Rg je_ weils "R _-10 -X _n - is;

R _{43 is} unsubstituted or substituted phenyl, 1- or 2-naphthyl or heteroaryl;

0, S, SO, SO ₂ , CH ₂ , a single, bivalent bond, -CH ₂ O-, CH ₂ S-, -CH (CH ₃ ) O, -CH (CN) O-, -CH = NO- , -C (CHO = NO-, -CH ₂ CH ₂ O-, -CH ₂ CH ₂ -, -C = C-, -CHgSO-, -CH ₂ SO ₂ -, -OCHgCHgO-, -CH (alkyl) - represents, -CONH-, and

B ₁ C represents 0, S, NH or NR ₄₄ , wherein R _{44 is} alkyl, alkylsulfonyl, polyhaloalkylsulfonyl, alkenyl, alkynyl, alkoxycarbonyl; unsubstituted or substituted aryl, aralkyl, aryloxy, arylamino, aroyl or arylsulfonyl, provided that R ₄₁ and R _{42 are} both other than

R ₄₃ -X ₂₃ - are when B ₁

R _AV -Ni, R _Aq -alkyl-Ni, R ₄ , -C (= O) -Ni,

"43

43

43 ~ ^S0 2 ^W '' ^R ₄₃ - ° - ^N '~ ^or R ₄₃ -HH-Ni, and further provided that one of R ₄₁ and R ₄₂ is R ₄₃ -X ₂₃ - when B ^ c is something other than R ₄₃ -N ^, R ₄₃ -alkyl-NC, R ₄₃ -C (= O) -N "f, R ₄₃ -SO ₂ N ':, R ₄₃ -O-NC or R ₄₃ -NH-K is?

or

wherein:

^R 45 ^'R 46' ^R 47 ¹ ^ ¹⁴ ^ 48 ^{independently} ä ⁿ GIS represent hydrogen, halogen, nitro, cyano group, polyhaloalkyl, Polyhaloalkoxygruppe, alkylsulfonyl, Polyhaloalkylsulfonyl, acyl, alkyl thio, alkyl, alkoxy, alkylsulphinyl or R ₄ ^ - X ₂₄ -, provided that one of R ₄₅ , R ₄₆ , R ₄₇ and R ₄₈ is R ₄₉ -X ₂₄ , and further provided that R ₄ (j, R ₄ £, R y and R ₄₈ each no longer have two of the components hydrogen, alkyl or alkoxy group;

R.Q unsubstituted or substituted phenyl, 1- or 2-naphthyl. or heteroaryl;

X ₂₄ O, S, SO, SO ₂ , CHg, a single, bivalent bond, -CH ₂ O-, -CH ₂ S-, -CH (CH ₃ ) O-, -CH (CH) O-, -CH = HO-, -C (CH ₃ ) = HO-, -CH ₂ CH ₂ O-, -CH ₂ CH ₂ -, -C = C-, -CH ₂ SO-, -CH ₂ SO ₃ -, -CH (Alkyl) -, -CONH- represents;

Y ₄ O is halogen and B ₁ V represents O, S or NH;

wherein:

is selected from a monocyclic aromatic or non-aromatic ring system, a bicyclic aromatic or non-aromatic ring system, a polycyclic aromatic or non-aromatic ring system, and a bridgehead ring system which may be saturated or unsaturated;

B is -CH = N-, -Ii = CH-, -CH = CH-, -CO-, -SO ₃ -, .CH ₂ CO-, -COCHg-, -C & H-, -IiHCO-, -SO ₂ NH -, -MHSO ₂ -, -SO ₂ N (alkyl) -, -N (alkyl) SO ₂ - -OSO ₂ -, -CS-, -K <, -NH-, -N (alkyl) -, -OCH ₂ , -SCH ₂ -, -NHCH ₂ -, -N (.. alkyl) CH ₂ -, -SCO-, -OCH ₂ -, -OCQ-, -CH ₃ -, -CH ₂ CH ₂ - or -SCH _{2 represents} CO, provided that phenyl is substituted when B ^ is -CO- and R ^ ₀ is phenyl, and

Yg ₄ and Irr are independently halogen;

(Xx)

wherein:

Rp _{51 represents} an unsubstituted or substituted, 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 bridging ring system which may be saturated or unsaturated; B -CH = N-, -N = CH-, -CH = CH-, -CO-, -SO ₃ -, -CH ₃ CO-, -COCH-, -C§HH-, -NHCO-, -SO ₃ HH-, -HHSO ₂ -, -SO ₃ N (alkyl) -, -N (alkyl) -SO ₂ -, -OSO ₂ -, -CS-, -Ni, -HH-, -N (alkyl) -, -OCH ₂ -, -SCH ₂ -, -HHCH ₂ -, -N (alkyl) CH ₂ , -S-CO-, -OCHg-, -OCO-, -CH ₂ -, -CH ₂ CH ₃ - or - Represents SCH ₂ CO-;

B _{19 is} -CH ₂ or -CH (alkyl) - and i is 0 or 1 and

R ^ represents ₀ an unsubstituted or substituted, carbocyclic or heterocyclic ring system, which Removing

Y ₅₆ and

are independently halogen;

(Xxi)

wherein:

B ₂₀ -CH ₂ C (CH ₃ ) ₂ SCH ₂ -, -CH ₂ CH = C (CH ₃ ) OCH ₂ -, -CH ₂ CH ₂ SCH ₂ CH (CH ₃ ) -, -CH ₂ CH ₂ SCH ₂ CH ₂ -, -CH ₂ SCH ₂ CO-, -COCHgC (CH ₃ ) gCHgCO-, -COCH ₂ CH (C ₆ H ₅ ) CH ₂ CO-, -COHH (C ₆ H ₅ ) CH ₂ CH ₂ O- , -COC (CHJ ₂ IiHCO-, -CH ₂ CH ₂ W (C ₆ H ₅ ) CH ₂ CH ₂ -, -CH ₂ N (C ₆ H ₅ ) CH ₂ CH ₂ , -CH ₂ CH ₂ CH (C ₆ H ₅ ) CH ₂ CH ₂ -, -CO (CH ₂ ) ₃ CO-, - CO (CH ₂ J ₂ CO-, -COCH ₂ CH (CH ₃ ) CH ₂ CO-, -COCH (CH ₃ ) CH ₂ CO-, -COC (CH ₃ ) ₂ CH ₂ CO-, -COC (CH ₃ ) ₂ C (CH ₃ ) ₂ CO-, -CO (CH ₂ ) ₄ CO-, -CO (CHg) ₅ CO- .

-CO (CHg) ₅ CH ₂ -, -CO (CH _{2) 4} CH ₂ -, -CO (CHg) ₃ CH ₂ -, -CO (CHg) ₂ CH ₂ -, -COCH ₂ SCHgCO-, -COCH ₂ II (R ₅₂ ) CHgCO-, -COCH ₂ OCH ₂ CO-, -COCH ₂ SCS-, -COCH = CH-H = CH-, -CH ₂ CH (C ₆ H ₅ ) CH ₂ -H = CH- or -CO _{2 represents} -CH ₂ CH ₂ ;

R _{52 represents} hydrogen, alkenyl, unsubstituted or substituted aryl or alkaryl and

Y ₅₈ and

are independently halogen;

4ί

^L 60

(Xxii)

wherein!

Rc _{3 represents} unsubstituted or substituted cycloalkenyl, cycloalkadienyl, cycloalkatrienyl, bicyclicalkyl, bicyclicadienyl, iricycloalkyl, bicyclickenyl, tricyclic alkenyl or trxcycloalkadtenyl, the permissible substituents being the same or different and one or more of the following: alkyl, halogen, haloalkyl, polyhaloalkyl, alkoxy , Alkylthio group, alkylsulfonyl, polyhaloylkoxy, hitro, cyano, acyl, aroyl, aryl, alkoxycarbonyl, alkoxycarbonyloxy, azyloxy, oxo group or -CH = CHCH = CH- or -CH = CHCHg, which join adjacent carbon atoms to form a six to form - or five-membered ring; Y ₆₀ and Y ₆ -) are independently halogen and

X _{25 represents} 0, S, HH, CHg, -CHgO- or a single divalent bond;

(Xxiii)

wherein:

Ec. may be the same or different and is one or more of the following: hydrogen, halogen, alkyl, aryl, aralkyl, alkenyl, alkynyl, polyhaloalkyl, HHg, HH (alkyl), H (alkyl) 2 alkoxy, polyhaloalkoxy, alkylthio , Alkylsulfinyl, alkylsulfonyl, aralkoxy, COgAlkyl, CONH (alkyl), COHH ₂ , C0H (alkyl) ₂ , SO ₂ H (alkyl) g, SOgNH (alkyl), SO ₂ NHg, acyl, C0 (O-alkyl) ₂ , Acyloxy group, acyl-CON (alkyl) or 2,3 - (- CH = CHCH = CH-), 3,4 - (- CH = CHCH = CH-), 2,3- (CHg) ₄ - or 3,4 - (CH ₂ ) .- connecting the adjacent carbon atoms to form an unsubstituted or substituted six-membered ring;

₂ 0, S, SO, SO ₂ , CH ₂ , a single divalent bond, -CH ₂ O-, -CH ₂ S-, -CH (CH ₃ ) O, -CH (CH) O-, -CH = HO -, -C (CH ₃ ) = NO-, -CH ₂ CH ₂ O-, -CH ₂ CH ₂ -, -C = C-, -CH ₂ SO-, -CH ₂ SO ₂ -, -OHO -OCHgCH ₂ - or -OCH ₂ - represents and

Y ₅₀ and

are the same or different and are halogen;

^R 68 ~ ^X 27 ~ ^W <

(Xxiv)

^Z 2 ^Y 68

wherein:

Rg _{8 represents} unsubstituted or substituted phenyl or 1- or 2-naphthyl;

X _{27 is} -CH (alkyl) O-, -C (alkyl) gO-, -OCH ₂ -, -C (halo) ₂ , -O-OCH ₂ CH ₂ O-, -CH ₂ O-, -C = C -, -OCH (alkyl) -, -OC (alkyl) ₂ , -OCH (alkyl) O-, -OC (alkyl) ₂ O-, -OCH (alkyl) CHgO-, -OCH (alkyl) CH (alkyl) 0, -CH (alkyl) CH (alkyl) -, -CH (alkyl) -, -C (alkyl) ₂ -, -CH ₂ CH ₂ O-, -OCH ₂ CH ₂ -, -CH (alkyl) CHgO -, -CH ₂ CH ₂ -, -CH) CN) O-, -C (alkyl) (CN) O-, -CHiPolyhaloylkyDO-, -C (CN) = NO-, -C (NH-AIkyI) = NO -, -CJN (alkyl) ₂ J = N0-, -C (S-alkyl) = HO-, -C (O-alkyl) = NO-, -SC (= O) O-, -MHC (= 0) 0-, N (alkyl) C (= O) O-, SO, SO ₂ , -CH ₂ S (O) _h -, -CH (alkyl) S (O) _h -, -S (O) _h CH ₂ -, -OC (= S) S-, -C (= O) S-, -C (= S) -S-, -NH (alkyl) C (= O) S-, -N (alkyl) - , -N (R ₃₄ ) -, -SO ₂ NH-, -SO ₂ N (alkyl) -, -CONH-, -CON (alkyl) -, -SC (= O) N (alkyl) -, -SC ( = O) NH-, -NHSO ₂ NH-, -N (alkyl) SO ₂ N (alkyl) -, -N (alkyl) SO ₂ NH-, -NHSO ₃ N (alkyl) -, -C (O-alkyl ) = N-, -C (S-alkyl) = N-, -CH (halogen) -, -C (alkyl) (halogen) -, -CH (CN) -, -C (alkyl) (CN) -, -NH (alkyl) NH-, -NH-N (alkyl) -; -NH-NH-, -N = N-, -C (= O) -, -C (= O) C (= O) -, -CH (O-alkyl) -, -CH ₂ C (= 0 ) -, -C (= O) CH ₂ , -CH (alkyl) C (= O) -, -C (= O) CH (alkyl) -,

-CH = CH-, -C (alkyl) = CH-, -CH = C (alkyl) -, -C (alkyl) = C (alkyl) -, -Ci = O) CH = CH-, -PiY ₄₃ ) (Y ₄₄ alkyl), unsubstituted or substituted -PiY ₄₃ ) (Y ₄₄ -aryl) or arylene, -Si (halo ₂ -,. -Si {alkyl) ₂ , -OC (= O) N (alkyl) - , -OCH ₂ C (= O) N (alkyl) -, -N (alkyl) CON (alkyl) -; -OCi = O) NH-, -NHCONH-, -SOgNHCi = O) NH-, -NHCi = S) NH, -CH-CH-, -C (alkyl) -CH-, -CH-C (alkyl) - or

V ^ / V

V -q

-C (alkyl) -C (alkyl) - represents,

wherein h is a value from 0 to 2 inclusive, R _{34 is} azyl, alkylsulfonyl, polyhaloalkyl, polyhaloazyl, polyhaloalkylsulfonyl or unsubstituted or substituted aroyl or arylsulfonyl, and Y ₄₃ and Y _{44 are} independently 0 or 3;

ZJ and Z _{2 are} independently 0, S, C 1 -C 6 alkylidene, substituted or unsubstituted benzylidene, HH or NR ¹ ", wherein R '" is alkyl, aryl, aralkyl, alkenyl or alkynyl, and

Yg "and Yg _{8 are the} same or different and are hydrogen, halogen, alkyl, cyano, polyhaloalkyl, alkoxy, polyhaloalkoxy, haloalkyl, alkylthio, alkylsulfinyl, alkylsulfonyl, nitro, aryl, polyhaloalkylsulfonyl, alkylamino, dialkylamino, acylamino, azyloxy , Alkylsulfonyloxy, arylsulfonyloxy, alkenylsulfonyloxy, haloalkylsulfonyloxy, polyhaloalkylsulfonyloxy, phosphono or phoaphino group;

(Xxv)

wherein:

R _{fiq represents} unsubstituted or substituted phenyl or 1- or 2-naphthyl;

X _{28 is} NH, CHg or a divalent bond;

Z ₃ and Z _{4 are} independently 0, S, C 1 -C 6 -alkylidene, substituted or unsubstituted benzylidene, NH or NR ¹ "wherein R ¹ " is alkyl, aryl, aralkyl, alkenyl or'alkynyl, and

YgQ and Y "q are the same or different and are hydrogen, halogen, alkyl, cyano, polyhaloalkyl, alkoxy, polyhaloalkoxy, haloalkyl, alkylthio, alkylsulfinyl, alkylaulphonyl, nitro, kryl, polyhaloalkylsulfonyl, alkylamino, dialkylamino, azylamino, azyloxy , Alkylsulfonyloxy, arylsulfonyllosy, alkenylsulfonyloxy, haloalkylsulfonybxy, polyhaloalkylsulfonyloxy, phosphono or phosphino group, provided that Yg "and Y" _Q together do not represent either the same halogen or halogen and hydrogen;

^R 7O " ^X 29 ~ ^]

(Xxvi)

wherein:

R _{70 represents} an unsubstituted or substituted, unsaturated or saturated, aromatic or non-aromatic, heterocyclic ring system selected from isoxazole, isothiazole, pyrazole, imidazole, 1,2,4-triazole, 1,2,4-oxadiazole, 1,3 , 4-oxadiazole, 1,2,4-thiadiazole, 1,3,4-thiadiazole, oxazole, thiazole, benzopyrazole, benzimidazole, benzoxazole, benzothiazole, indole, pyrrole, furan, thiophene, benzofuran, benzothiophene, pyridine, pyrimidine, pyridazine , Pyrazine, 1,3,5-triazine, 1,2,4-triazine, quinoline, isoquinoline, quinazoline, phthalazine, benzopyridazine, benzopyrazine, carbazole, dibenzofuran, dibenzothiophene, benzoxazine, phthalimide, benzopyran, dibenzopyridine, pyridopyridine, pyrazolopyridine, Tetrahydropyrimidinedione, piperidine, morpholine, tetrahydrofuran, tetrahydrothiophene, pyrrolidine, thiomorpholine, piperidin-2-one, piperidine-2,6-dione, 2,5-pyprolidinodione, 3-morpholinone, 2-oxohexamethyleneimine, 2-oxotetramethyleneimine, 1 Pyrazoline, 2-pyrazoline, pyrazolidine, 2-imidazolidinone, 2- Imidazolidinethione, 2,4-imidazolidinedione, 1,2-oxathiolane, 1,3-oxathiolane, 1,3-oxathiane, 1,4-oxathiane, 2 (1H) -pyrazinone, 2H-pyran-2-one, 4H-pyran 4-one, 2H-pyran-2-thione, 4H-pyran-4-thione, tetrahydropyran, tetrahydrothiopyran, 7-0xabtzyklo- [2.2.1] heptane, 7-azabicyclo [2.2.1heptane, oxetane, coumarin, 1, 3-dioxane, 1-4-dioxane or 1,3-dioxolane;

X _{29 is} -CH (alkyl) O-, -C (alkyl) ₂ O, -OGH ₂ -, -CHgO-, -CH ₂ -, a bivalent bond, -G (halo) ₂ -, -OCH ₂ O-, -OCHgCHgO-, -C = C-, -OCH (alkyl) -, -OC (alkyl) ₂ , -OCH (alkyl) O-, -OC (alkyl) ₂ O-, -OGH (alkyl) CH ₂ O- , -OCH (alkyl) CH (alkyl) O-, -CH (alkyl) CH (alkyl) -, -CH (alkyl) -, -C (alkyl) ₂ -, -CH ₂ CH ₂ O-, -OCH ₂ CH ₂ -, -CH (alkyl) CH ₂ O-, -CHgCHg-, -CH (CN) O-, - (C (alkyl) (CN) O-, -CH (polyhaloalkyl) O-, -C (CN ) = NO-, -C (NHalkyl) = N0-, -CJN (alkyl) ₂ ] = NO-, -C (S-alkyl) = NO-, -C (O-alkyl) = NO-, -SC (= O) O, -ira C (= O) O-, -N (alkyl) C (= O) O-, SO, SO ₂ , -CH ₂ S (O) ₁₁ -, -CH (alkyl) S (O) _h -, -S (O) _h CH ₂ -, -OC (= S) S-, -C (= O) S-, -C (= S) -S-, -NH (alkyl) C (= 0) S-, -O (C = O) S-, -NH-, -N (alkyl) -, -N (R ₃₄ ) -, -SO ₂ NH-, -SO ₃ N (alkyl) - , -CONH-, -CON (alkyl) -, -SC (= O) Ji (alkyl) -, -SC (= O) NH-, -NHSO ₂ NH-, -N (alkyl) SO ₂ N (alkyl) -, -N (alkyl) SO ₂ NH-, -NHSO ₂ N (alkyl) -, -C (O-alkyl) = N-, -C (S-alkyl) = H-, -CH (halogen) -, -C (alkyl) (halo) -, -CH (CN) -, -C (alkyl) (CN) -, -NH (alkyl) NH-, -NH-N (alkyl) -; -NH-NH -, -N = N-, -C (= O) -, -C (= O) C ( = O) -, -CH (O-alkyl) -, -CH ₂ C (= O) -, -C '(= O) CH ₂ , -CH (alkyl) C (= O) -, -C (= 0) CH (alkyl) -, -CH = CH-, -C (alkyl) = CH-, -CH = C (alkyl) -, -C (alkyl) = C (alkyl) -, -C (= 0) CH = CH-, -P (Y ₄₃₎ (Y ₄₄ alkyl) -, unsubstituted or substituted -P (. Y) (Y ₄₄ -A _r yl7 or arylene, -Si (halo) ₂ -, -Si ( alkyl) ₂ , -OC (= O) N (alkyl) -, -OCH ₂ C (= O) N (alkyl) -, -N (alkyl) CON (alkyl) -; -OC (= O) NH-, -NHCONH-, -SO ₂ NHC (= O) NH-, -NHCC = S) NH-J-SfH-CH-, -C (alkyl) -CH-, -CH- C (alkyl) - or

\ (\ "^ O ^ ^X 0 -C (alkyl) -C (alkyl) -,

wherein h is a value of 0 to 2 inclusive, R _{34 is} azyl, alkylsulfonyl, polyhaloalkyl, polyhaloazyl, polyhaloalkylsulfonyl or unsubstituted or substituted aroyl or arylsulfonyl and Y ₄ . and Y _{43 are} independently 0 or S;

Z 1 and Z 2 are independently 0, S, C ₁ -C ₈ -alkyl, substituted or unsubstituted benzylidene, NH or NR ¹ ", wherein R ¹ " is alkyl, aryl, aralkyl, alkenyl or alkynyl and

Υγί and Υγ2 are the same or different and are hydrogen, halogen, alkyl, cyano, polyhaloalkyl, alkoxy, polyhaloalkoxy, haloalkyl, alkylthio, alkylsulfinyl, alkylsulfonyl, nitro, acyl, polyhaloalkylsulfonyl, amino, alkylamino, dialkylamino, azylamino, azyloxy -, alkylsulfonyloxy, arylsulfonyloxy, alkenylsulfonyloxy, haloalkylsulofnyloxy, polyhaloalkylsulfonyloxy, alkoxycarbonyl, alkylaminocarbonyl, aminocarbonyl, di-alkylaminocarbonyl, dialkylaminosulfonyl, alkylaminosulfonyl, aminosulfonyl, dialkoxyalkyl, arylsulfonyl, phosphono or phosphino;

(Xxvii)

Ry represents unsubstituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkadienyl, cycloalkytrienyl, bicyclalkyl, bicyclickenyl, bicyclicadienyl, tricyclicalkyl, tricyclic alkenyl or tricyclicycadienyl;

X ₃₀ -CH (alkyl) O-, -C (alkyl) _g 0-, -OCH ₂ -, -CH ₂ O-, -CH ₂ -, a bivalent bond, -C (halogen ₂ , -OCH ₂ O-) , -OCH ₂ CH ₂ O-, -3 = C-, -OCH (alkyl) -, -0C (alkyl) ₂ , -OCH (alkyl) O-, -OC (alkyl) ₂ 0-, -OCH (alkyl ) CH ₂ 0-, -OCH (alkyl) CH (alkyl) O-, -CH (alkyl) CH (alkyl) -, -CH (alkyl) -, - <C (alkyl) ₂ -, -CH ₂ CH ₂ O-, -OCH ₂ CH ₂ -, -CH (alkyl) CH ₂ O-, -CH ₂ CH ₂ -, -CH (CN) O-, -C (alkyl) (CN) O-, -CH (polyhaloalkyl ) 0-, -C (CN) = NO-, -C (NHalkyl) = NO-, -CJN (Al-)

₂ = EO-, -C (S-alkyl) = HO-, -C (O-alkyl) = NO-, -SC (= O) O-, _T NHC (= O) O-, -Ii (alkyl) C (= O) O-, SO, SO ₂ , -CH ₂ S (OOj ₁ -, -CH (alkyl) S (O) _h -, -S (O) ₁₁ CH ₂ -, -O C (= 3) S-, -C (= O) S-, -C (= S) -S-, -NH (alkyl) C (= O) S-, -O (C = O) S-, -MH-, - N (alkyl) -, -N (R ₃₄ ) -, -SO ₂ HH-, -SO ₂ N (alkyl) -, -CONH-, -CONO-alkyl) -, -SC (= O) H (Al-1-cy) _, -SC (= O) HH-, -NHSO ₂ NH-, -N (alkyl) SO ₂ N (alkyl) -, -N (alkyl) SO ₂ NH-, -HHSO ₂ N (alkyl) -, - C (O-alkyl) = N-, -C (S-alkyl) = N-, -CH (halo) -, -O (alkyl) (halo) -, -CH (CN) -, -C (alkyl) (CM) -, -NH (alkyl) NH-, -HH-N (alkyl) -; -HH-NH-, -H = N-, -C (= O) -, _C (= O) C (= O) -, -CH (O-alkyl) -, -CH ₂ C (= O) - , -Ci = O) CH ₃ , -CH (alkyl) C (= O) -, -C (= O) CH (alkyl) -, -CH = CH-, -C (alkyl) = CH-, -CH = C (alkyl) -, -C (alkyl) = C (alkyl) -, -C (= O) CH = CH-, -P)

-Alkyl), unsubstituted or substituted

-P (Y ₄₃ ) (Υ- aryl) or arylene, -Si (halo ₂ -, -Si (alkyl) ₂ , -OC (= O) H (alkyl) -, -OCH ₂ C (= O) N (alkyl) -, -N (alkyl) CON (alkyl) -; -OC (= O) NH-, -HHCOHH-, -SO ₂ HHC (= O) NH-, -NHC (= S) HH, - CH-CH-,

^V 0 -C (alkyl) -CH-, -CH-C (alkyl) - or -C (alkyl) -C (alkyl) - dar-

^^ 0 ^ ^X 0 ^ * O ^

provides,

wherein h is 0 to 2 inclusive, R _{34 is} acyl, alkylsulfonyl, polyhaloalkyl, polyhaloazyl, polyhaloalkylsulfonyl or unsubstituted or substituted aroyl or arylsulfonyl, and Y ₄₃ and Y _{44 are} independently 0 or S;

Z ₇ and Z _{8 are} independently O, S, C 1 -C 6 alkylidene, substituted or unsubstituted benzylidene, HH or NH ¹ ", wherein R" ^{1 is} alkyl, aryl, aralkyl, alkenyl or alkynyl, and

Υγ ₃ and Y _{74 are} identical or different and are hydrogen, halogen, alkyl, cyano group, polyhaloalkyl, alkoxy, polyhaloalkoxy, alkylthio, haloalkyl, alkylsulfinyl, alkylsulfonyl, nitro, aryl, polyhaloalkylsulfonyl, alkylamino, dialkylamino, acylamino, azyloxy Alkylsulfonyloxy, arylsulfonyloxy, alkenylsulfonyloxy, haloalkylsulfonyloxy and polyhaloalkylsulfonyloxy group;

(Xxviii)

wherein:

-CH ₂ C (CH ₃ )

2 ₂ -, -CH ₂ CH = C (CH ₃ ) OCH ₂ -, -CH ₂ CH ₂ SCH ₂ CH (CH ₃ ) -, -, - CH ₂ SCH ₂ CO-, -COCH ₂ C (CH ₃ ) ^ H ₂ CO-,

₂₆₅ CH ₂ CO-J-CONH (C ₆ H ₅₎ CH ₂ CH ₂ O-, -COC (CH ₃ J ₂ KHCO-, -CH ₂ CH ₂ N (C ₆ H ₅₎ CH ₂ CH ₂ -, - CH ₂ N (C ₆ H ₅ ) CH ₂ CH ₂ -, -CH ₂ CH ₂ CH (C ₆ H ₅ ) CH ₂ CH ₂ -, -00 (CH ₃ ) ₃ CO-, -C0 (CH ₂ ) ₂ CO -, - COCH ₂ CH (CH ₃ ) CH ₂ CO-, -COCH (CH ₃ ) CH ₂ CO-, -COC (CH ₃ J ₂ CH ₂ CO-, -COC (CH ₃ ) ₂ C (CH ₃ ) ₂ CO, -CO (CH ₂ ) ₂ CO-, -CO (CH ₂ ) ₅ CO-, -CO (CH ₂ ) ₅ CH ₂ r-, -CO (CH ₂ ) ₄ CH ₂ -, -CO ( CH ₂ ) ^ H ₂ -, t

-COCH ₂ SCH ₂ CO-, -COCH ₂ K (R ₅₂ ) CH ₂ CO-, -COCH ₂ OCH ₂ CO-, -COCH ₂ SCS-, -COCH = CH-N = CH-, CH ₂ CH (C ₆ H ₅ ) CH ₂ -K = CH- or -CO ₂ -CH ₂ CH ₂ - wherein R _{52 is} hydrogen, alkenyl, unsubstituted or substituted aryl or alkaryl;

and

independently of one another 0, S, Cj-Cg-alkylidene, t d

jg

substituted or unsubstituted benzylidene, NH or NR " ¹ , wherein R" ^{1 is} alkyl, aryl, aralkyl, alkenyl or alkynylate, and

Y " ₆ and ϊγ _{5 are} identical or different and are hydrogen, halogen, alkyl, cyano group, polyhaloalkyl, alkoxy, polyhaloalkoxy, haloalkyl, alkylthio group, alkylsulfinyl, Aulkysulfonyl, hitro group, acyl, polyhaloalkylsulfonyl, amino group, alkylamino, dialkylamino, azylamino , Azyloxy, alkylsulfonyloxy, arylsulfonyloxy, alkenylsulfonyloxy, haloalkylsulfonyloxy, polyhaloalkylsulfonyloxy, phosphono or phosphino group;

(Xxix) wherein:

R _{72 is} unsubstituted or substituted phenyl or 1- or 2-naphthyl;

X ^ ₁ -OCH ₂ -, -CH ₂ -, a bivalent bond, -c (halogen) ₂ - -C = C-, -OCH (alkyl) -, -OC (alkyl) ₂ , -CH (alkyl) CH (Alkyl) -, -CH (alkyl) -, -C (alkyl) ₂ -, -OCH ₂ CH ₂ -, -CH ₂ CH ₂ -, 30, -S-, SO ₂ , -CH ₂ S (O) ₁₁ -, -CH (alkyl) S (O) _H, -S (0) _h CH ₂ -, -CH (halo) -, -C (alkyl) (halo), -CH (CK) -, C (alkyl ) (CN) or -C (= O) -, -CH (O-alkyl) -, -CH ₂ C (= O) -, -C (= O) CH ₂ , -CH (alkyl) C (= O ) -, -C (= O) CH (alkyl) -, -CH = CH-, -C (alkyl) = CH-, -CH = C (alkyl) -, -C (alkyl) = C (alkyl) - , -C (= O) CH = CH-, arylene, -Si (halo, -Si (alkyl) o. -CH-CH-, -C (alkyl) -CH-, -CH-C (alkyl) - or

V \ ο- ^κ V

-C (alkyl) -C- (alkyl) - represents,

where h is a value of 0 to 2 inclusive;

Z _{11 represents} O, S, C 1 -C 6 alkylidene, substituted or unsubstituted a benzylidene, NH or NR ¹ ", wherein R" ^{1 is} alkyl, aryl, aralkyl, alkenyl or alkynyl, and

Y ", Y" o and Υ ™ - are identical or different and are hydrogen, halogen, alkyl, hydroxyl, cyano, polyhaloalkyl, alkoxy, polyhaloalkoxy, haloalkyl, alkylthio, alkylsulfinyl, alkylsulfonyl, nitro, acyl, polyhaloalkylsulfonyl, alkylamino representing amino, dialkylamino, Azylamino-, Azyloxy-, alkylsulfonyloxy, arylsulfonyloxy, Alkenylsulfonyloxy-, haloalkylsulfonyloxy, Polyhaloalkylsulf onyloxy-, phosphono or phosphino group, on condition ,,. that X _"8 none amino, alkylamino , Y.sup.-, and Y.sup.g are hydrogen, and under the further condition that Y.sup.yg can not be hydrogen or a hydroxy group when Y.sup.n and Y.sup.g are the same halogen;

^Z 12, ^Y 80

^X 82

wherein:

(Xxx)

73 represents an unsubstituted or substituted, unsaturated or saturated, aromatic or non-aromatic, heterocyclic ring system selected from isoxazole, isothiazole, pyrazole, imidazole, 1,2,4-triazole, 1,2,4-oxadiazole, 1,3, 4-oxadiazole, 1,2,4-thiadiazole, 1,3,4-thiadiazole, oxazole, thiazole, benzopyrazole, benzimidazole, benzoxazole, benzothiazole, indole, pyrrole, furan, thiophene, benzofuran, benzothiophene, pyridine, pyrimidine, pyridazine, Pyrazine, 1,3,5-triazine, 1,2,4-triazine, quinoline, siochinoline, quinazoline, phthalazine, benzopyridazine, benzopyrazine, carbazole, dibenzofuran, dibenzothiophene, benzoxazine, phthalimide, benzopyran, dibenzopyridine, pyridopyridine, pyrazolopyridinium, tetrahydropyrimidinedione, Piperidine, morpholine, tetrahydrofuran, tetrahydrothiophene, pyrrolidine, thiomorpholine, piperidin-2-one, piperidine-2,6-dione, 2,5-pyrrolidinedione, 3-morpholinone, 2-oxo-hexylmethylene-imine, 2-oxo-tetraethyleneimine, 1-pyrazoline, 2- Pyrazoline, pyrazolidine, 2-imidazolidinone, 2- Imidazolidinethione, 2,4-imidazolidinedione, 1,2-oxathiolane, 1,3-oxathiolane, 1,3-oxathiane, 1,4-oxathiane, 2- (1H) -pyrazinone, 2H-pyran-2-one, 4H- Pyran-4-one, 2H-pyran-2-thione, 4H-pyran-4-thione, tetrahydropyran, tetrahydrothiopyran, 7-oxabicyclo [2.2.i] heptane, 7-azabicyclo [2.2.i-heptane, oxetane,! Coumarin, 1 , 3-dioxane, 1,4-dioxane or 1,3-dioxolane; X _{32 is} -OCH ₂ -, -CH ₂ -, a bivalent bond, -C (halogen) ₂ , -C = C-, -OCH (alkyl) -, -OC (alkyl) ₂ -, -CH (alkyl) CH (Alkyl) -, -CH (alkyl) -, -C (alkyl) ₂ -, OCH ₂ CH ₂ -, -CH ₂ CH ₂ -, SO, -S-, SO ₂ , -CH ₂ S (O) ₁₁ -, -CH (alkyl) S (O) _h -, -S (O) _h CH ₂ -, -C (alkyl) (halo) -, -CH (halo) -, -CH (CW) -, -C (Alkyl) (CN) -, -C (= O) -, -CH (O-alkyl) -, -CH ₂ C (= O) -, -C (= O) CH _2> -CH (alkyl) C (= 0) -, -C (= O) CH (alkyl) -, -CH = CH-, -C (alkyl) = CH-, -CH = C (alkyl) -, -C (alkyl) = C ( Alkyl), -C (= O) CH = CH-, arylene, -SI (alkyl) ₂ , -Si (halogen) ₂ -, -CH-CH-, -C (alkyl) -CH-, -CH- C (AIkVl) - or

^X θ ' ^V "' ^ 0 S ^ O

-C (alkyl) -C (alkyl) - represents,

where h is a value from 0 to 2 inclusive;

Z ₂ , O 3, C 1 -C 6 -alkylidene, substituted or unsubstituted benzylidene, NH or KR ", where R" ¹ is alkyl, aryl, aralkyl, alkenyl or alkynyl, and

Yqq, Yq-J and Yg _{2 are the} same or different and are hydrogen, halogen, alkyl, hydroxy, cyano, polyhaloalkyl, alkoxy, polyhaloalkoxy, haloalkyl, alkylthio, alkylsulfinyl ,. Alkylsulfonyl, nitro group, acyl, polyhaloalkylsulfonyl, alkylamino, amino, dialkylamino, acylamino, acyloxy, alkylsulfonyloxy, arylsulfonyloxy, alkenylsulfonyloxy, haloalkylsulfonyloxy, polyhaloalkylsulfonyloxy, phosphono or phosphino group;

(Xxxi)

wherein:

R ". unsubstituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkadienyl, cycloalkatrienyl, bicyclicalkyl, bicyclickenyl, bicyclicadienyl, tricyclicalkyl, tricycloalkenyl or tricyclicycadienyl;

Xj2 -OCHg-r'-CHp- »a bivalent bond, -C (halo) _2> -C = C-, -OCH (alkyl) -, -OC (alkyl) ₂ ,. -CH (alkyl) CH (alkyl) -, -CH (alkyl) -, -C (alkyl) ₂ -, -OCHgCHg-, -CH ₂ CH ₂ -, SO, -S-, SO ₂ T -CH ₂ S (O) ₁₁ -, -CH (alkyl) S (O) _h -, -S (0) _h CH ₂ ~, -CH (halo) -, -C (alkyl) (halo) -, -CH (CN) -, -C (alkyl) (CN) - or -C (= 0) -, -CHCO-alkyl) -, -CH ₂ Ci = O) -, -C (= O) CH _2S -CH (alkyl) C (= O) -,

-C (= O) CH (alkyl) -, -CH = CH-, -C (alkyl) = CH-, -CH = C (alkyl) -, -C (alkyl) = C (alkyl) -, -CC = O) CH = CH-, arylene, -Si (halo) ₂ ~, -Si (alkyl) ₂ , -CHKiHy, -C (alkyl) -CH-, -CH-C (alkyl) - or

^ c / ^ o ^ "o

-C (alkyl) -C (alkyl) - represents,

where h is a value from 0 to 2 inclusive;

Z ₁ - represents O, S, C ₁ -C 6 -alkylidene, substituted or unsubstituted benzylidene, NH or HR ¹ ", wherein R ^11! Alkyl, aryl, aralkyl, alkenyl or alkynyl, and ^Y 83 ' ^Y 84 ⁰ ^ ^ 85 are each of the same or different and are hydrogen, halogen, alkyl, hydroxy, cyano, polyhaloalkyl, alkoxy, polyhaloalkoxy, haloalkyl, alkylthio, alkylsulfinyl, Alkylsulfonyl, nitro group, acyl, polyhaloalkylsulfonyl, alkylamino, amino, dialkyl, acylamino, acyloxy, alkylsulfonyloxy, arylsulfonyloxy, alkenylsulfonyloxy, haloalkylsulfonyloxy or polyhaloalkylsulfonoyloxy group;

the permissible substituents for the formulas (i) to (xxxi) above are the same or different and are one or more of the following: hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiocyanato, Propargylthio-, hydroxyimino, alkoxyimino, trialkylsilyloxy, Aryldialkylsilyloxy-, triarylsilyloxy, Pormamidino-, Alkylsulfamido-, Dialkylsulfamidogruppe, alkoxysulfonyl, Polyhaloalkoxysulfonyl, Hadroxy-, amino group, Aminokarbonyl, Alkylaminokarbonyl, Dialkylaminokarbonyl, Aminothiokarbonyl, Alkylaminothiokarbonyl, Aminothiokarbonyl, Alkylarainothiokarbonyl, Dialkylaminothiokarbonyl , Nitro, cyano group, hydroxy carbonyl and derived salts, chloro group, alkyl, alkoxy group, polyhaloalkyl, polyhaloalkoxy group, alioxy carbonyl, substituted amino group in which the permissible substituents are the same or different and one or two of the following are propargyl, alkoxyalkyl, Alkyl thiolakyl, alkyl, alkenyl, haloalkenyl or polyhaloalkenyl; Alkylthio l ^ olylialoalkylthiogruppe, alkylsulfinyl, Polyhaloalkylsulfinyl, alkylsulfonyl, Polyhaloalkylsulfonyl Alkylsulfonylatnino-, Alkylkarbonylamino-, Polyhaloalkylsulfonylamino-, Polyhaloalkykarbonylaminogruppe, trialkylsilyl, aryldialkylsilyl, triarylsilyl sulfonic acid and derivative salts, acid, phosphonic acid and derivative salts, Alkoxykarbonylamino-, Alkylaminokarbonyloxy-, Dialkylaminokarbonyloxygruppe, Alkenyl, polyhaloalkenyl, alkenyloxy group, alkynyl, alkynyloxy, polyhaloalkenyloxy group, polyhaloalkynyl, polyhaloalkynyloxy group, polyfluoroalkanol, cyanoalkylamino group, semicarbazonomethyl, alkoxycarbonylhydrazonomethyl, alkoxyiminomethyl, unsubstituted or substituted aryloxyiminomethyl, hydrazonomethyl, unsubstituted or substituted arylhydrazonomethyl, one condensed with a mono-, di- or polysaccharide Hydroxy, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, aryloxy, aralkoxy, arylthio, aralkylthio, alkylthioalkyl, arylthioalkyl , Arylsulfinyl, arylsulfonyl, Haloalkylsulf ynyl, haloalkylsulfonyl, Haloalkenjäoxy-, Haloalkynyloxy-, Haloalkynylthiogruppe, Haloalkenylsulfonyl, PoIyhaloalkenylsulfonyl, alkoxysulfonyl, aryloxysulfonyl, propargyloxy, aroyl, Haloazyl, Polyhaloazyl, Aryloxykarbonyl, amino sulfonyl, Alkylaminosulf onyl, Dialkylaminosul- ,, fonyl, arylaminosulfonyl, Carboxyalkoxy, carboxyalkylthio, alkoxycarbonylalkoxy, azyloxy, haloalloxy, polyhaloacyloxy, aroyloxy, alkylsulfonyloxy, alkenylsulfonyloxy, arylsulfonyloxy, haloalkylsulfonyloxy, polyhaloalkylsulfonyloxy, aroylamino, haloazylamino, alkoxycarbonyloxy, arylsulfonylamino, aminocarbonyloxy , Cyanato, isocyanato, isothiocyanato, cycloalkylamino, trialkylammonium, arylamino, aryl (alkyl) amino, aralkylamino, alkoxyalkylphosphinyl, alkoxyalkylphosphinothioyl, alkylhydroxyphosphinyl, dialkylaminoalkoxy, dialkoxyphosphino, hydroxyamino, alkoxyamino, aryloxyamino, aryloxyimino, Oxo, thiono, alkylaminoalkox y-, alkoxyalkoxy, alkoxyalkenyl, cyanoalkoxy, dialkylsulfonium,

X f - X 1 * λ. - R-Jj - XR -, y

Y ₁ Y ₁

-X - R ₃ , - JU Y ₂ R ₄ , -Y ₄ - P- Y ₂ R ₄

Y ₃ R ₅

^R 1 " ^Ζ - ^R 36

(Xxxii)

(Xxxiii)

^L 66

^L 64

wherein:

₃ lodges are;

^Y 64 »

65 ^ * ^{1 Y} 66 el ^EICN or different and HAR ₁ 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 Bridging ring system which may be saturated or unsaturated, wherein the permissible substituents are the same or different and are one or more of the following: hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiozyano, propargylthio, hydroxyimino, Alkoxyimino, trialkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxy, lmmamidino, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylamine othiocarbonyl, dialkylaminothiocarbonyl, nitro, cyano, hydroxycarbonyl and derived salts, orthoramido, alkyl, alkoxy, polyhaloalkyl, polyhaloalkoxy, alkoxycarbonyl, substituted amino in which the permissible substituents are the same or different and are one or two of the following: propargyl, alkoxyalkyl, Alkylthioalkyl, alkyl, alkenyl, haloalkenyl or polyhaloalkenyl; Alkylthio, polyhaloalkylthio group, alkylsulfinyl, polyhaloalkylene sulfinyl, alkylsulfonyl, polyhaloalkylsulfonyl, alkylsulfonyimino, alkylcarbonylamino, polyhaloalkylsulfonylamino, polyhaloalkylcarbonylamino, trialkylsilyl, aryldialkylsilyl, triarylsilyl, sulfonic acid. and salts derived, and salts derived Phcqphonsäure, Alkoxykarbonylamino-, Alkylaminokarbonyloxy-, Dialkylaminokarbonylpxygruppen, alkenyl, Polyhaloalkenyl, alkenyloxy, alkynyl, alkynyloxy, Polyhaloalkenyloxygruppe, Polyhaloakynyl, Polyha loalkynyl oxy group, Polyfluorolakanol, Zynaoalkylaminogruppe, Semikarbazonomethyl, AIkoxykarbonylhydrazonomethyl, alkoxyiminomethyl, unsubstituted or substituted Aryloxyiminomethyl , Hydrazonomethyl, unsubstituted or substituted Arylhsrdrazonometyhl or mono-, di- or pdysaccharide fused hydroxy, haloalkyl, haloalkenyl, haloalkynyl, Alkoxjal kyl, aryloxy, aralkoxy, arylthio, Aralkylrthiogruppe, alkylthioalkyl, arylthioalkyl, arylsulfinyl, arylsulfonyl, haloalkylsulfinyl , Haloalkylsulfonyl, haloalkenyloxy, haloalkyny, cyano, haloalkynylthio, haloalkenylsulfonyl, polyhaloalkenylsulfonyl, alkoxysulfonyl, aryllexysulfonyl, propargyloxy, aroyl, haloazyl, polyhaloazyl, aryloxycarbonyl, Aminosulfonyl, alkylaminosulfonyl, dialkylaminosuflonyl, arylaminosulfonyl, carboxyalkoxy, carboxyalkylthio, alkoxycarbonylalkoxy, azyloxy, halooxyloxy, polyhalo-azyloxy, aroyloxy, alkylsulfonyloxy, alkenylsulfonybxy, arylsulfonyloxy, haloalkylsulfonyloxy, polyhaloalkylsulfonyloxy, aroylamino, haloazylamino, Alkoxy karbonyloxy, arylsulfonylamino, aminocarbonyloxy, cyanato, isocyanato, isothiocano, cycloalkylamino, ammonium, arylamino, aryl (alkyl) amino,

Alkylamino group, alkoxyalkyphosphinyl, alkoxyalkylphosphinothioyl, alkylhydroxyphosphinyl, dialkoxyphosphino, hydroxyamino, alkoxyamino, aryloxyamino, aryloxyimino, oxo, thiono, alkylaminoalkoxy, dialkylatinoalkoxy, alkoxyalkoxy, alkoxyalkenyl, cyanoalkoxy, dialkylsulfonium, -X, = X, - groups X = R ₃ , = XR ₃ ,

Y ₁ -XR ₃ , -P 1 -Y ₂ R ₄ , -Y ₄ -

or

R _{1 is} a substituted heteroatom or a substituted carbon atom or a substituted or unsubstituted, branched or straight chain containing two or more carbon atoms or heteroatoms in any possible combination, the permissible substituents being the same or different and one or more of the following: hydrogen , Halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiozyano, propargylthio, hydroximino, alkoxyimino, trialkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxy, sartnamidino, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy , Amino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, nitro, cyano, hydroxycarbonyl and derived salts, pormamido, alkyl, alkoxy, polyhaloalkyl, polyhaloalkoxy, alkoxycarbonyl, substituted te amino group, wherein the permissible substituents are identical or different and one or two of the following: propargyl, alkoxyalkyl, alkylthioalkyl, alkyl, alkenyl, haloalkenyl or polyhaloalkenyl; Alkylthio, Polyhaloalkylthiogruppe, alkylsulfinyl, Polyhaloalkylsulfinyl, Alkylsulf onyl, Polyhaloalkylsulfonyl, Alkylsulofnylamino-, Alkylkarbonylamino-, Polyhaloalkylsulfonylamino-, Polyhaloalkylkarbonylaminogruppe, trialkylsilyl, aryldialkylsilyl, triarylsilyl, Sülfonsäure and derived salts, and salts derived Phosphonaäure, Alkoxykarbonylatnino-, Alkylaminokarbonyloxy-, Dialkylaminokarbonyloxygruppe, alkenyl , Polyhaloalkenyl, alkenyixy group, alkynyl, alkynyloxy, polyhaloalkenyloxy group, polyhaloalkynyl, polyhaloalkynyloxy group, polyfluorosalkanol, cynaoalkylamino group, semicarbazonomethyl, alkoxycarbonylhydrazonomethyl, alkoxyiminomethyl, unsubstituted or substituted aryloxyiminomethyl, hydrazonomethyl, unsubstituted or substituted arylhydrazonomethyl, one condensed with a mono-, di- or polysaccharide Hydroxy group, haloalkyl, halolakenyl, haloalkynyl, alkoxyalkyl, aryloxy, aralkoxyv, arylthio, aralkylthio, alkylthioalkyl, arylthioalk yl, arylsulfinyl, arylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, HaIoalkenyloxy-, Haloalkynyloxy-, Haloalkynylthiogruppe, Haloalkenylsulfonyl, Polyhaloalkenylsulfonyl, alkoxysulfonyl, aryloxysulfonyl, propargyloxy, aroyl, Haloazyl, PoIyhaloazyl, Aryloxykarbonyl, aminosulfonyl, alkylaminosulfonyl, Dialkylaminosuflonyl, Arylatninosulfonyl, Karboxyalkoxy-, Karboxyalkylthio-, Alkoxycarbonylalkoxy, azyloxy, haloacyloxy, polyhaloazyloxy, aroyloxy, alkylsulphonyloxy, alkenylsulphonyloxy, arylsulphonyloxy, haloalkylsulphonyloxy, polyhaloalkylsulphonyloxy, arylsulphonylamino, haloazylamino, alkoxycarbonyloxy, arylsulphonylamino, arminocarbonyloxy, cyanato, isocyanato, , Isothiocyanato, cycloalkylamino, trialkylammonium, arylamino, aryl (alkyl) amino, aralkyl

t amino group, alkoxyalkylphosphinyl, alkoxyalkylphosphinothioyl, alkylhydroxyphosphinyl, dialkylatinoalkoxy, dialkoxyphosphino, hydroxyamino, alkoxyamino, aryloxyamino, aryloxyimino, oxo, thiono, alkylaminoalkoxy, alkoxyalkoxy, alkoxyalkenyl, cyanoalkoxy, dialkylsulfonium,

-X, = X.-X = R ₃ , = XR

-X -R ₃ , -

^Y 2V -h - \ ^Y 2 ^R 4 V ₅ ^Y 3 ^R 5

X is a divalent single or double bond, a substituted or unsubstituted heteroatom or substituted carbon atom, a substituted or unsubstituted, branched or straight chain containing two or more carbon atoms or heteroatoms in any combination, the permissible substituents being the same or different and one or more of the following are: hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiozyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, aryldialkylsilyoxy, triarylsilyloxy, formamdino, alkylsulfamido, Dialkylsulfamido group, alkoxysulfonyl, polyhaloalkoxyaulfonyl, hydroxy-amino group, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, hitro, cyano, hydroxycarbonyl and derived salts, formamido, alkyl, alkoxy, pol yhaloalkyl, polyhaloalkoxy, alkoxycarbonyl, substituted amino in which the permissible substituents are the same or different and one or two of the following: propargyl, alkoxyalkyl, alkylthioalkyl, alkyl, alkenyl, haloalkenyl or polyhaloalkenyl; Alkylthio, Polyhaloalkylthiogruppe, alkylsulfinyl, Polyhaloalkylsulfinyl, alkylsulfonyl, Polyhaloalkylsulfonyl, alkylsulfonylamino, Alkylkarbonylamino-, Polyhaloalkylsulfonylamino-, Polyhaloalkylkarbonylaminogruppe, trialkylsilyl, aryldialkylsilyl, triarylsilyl sulfonic acid and derivative salts, phosphonic acid and derivative salts, Alkoxykarbonylamino-, Alkylaminolarbonyloxy-, Dialkylaminokarbonyloxygruppe, alkenyl, Polyhaloalkenyl, alkenyloxy group, alkynyl, alkynyloxy, polyhaloalkenyloxy group, polyhaloalkynyl, polyhaloalkynyloxy group, polyfluoroalkanol, cyanoalkylamino group, semicarbazonomethyl, alkoaycarbonylhydrazonomethyl, alkoxyimxnomethyl, unsubstituted or substituted aryloxyiminomethyl, hydrazonomethyl, unsubstituted arylhydrazonomethyl, a mono-, di- or polysaccharide-fused hydroxy group, haloalkyl, Haloalkenyl, haloalkynyl, alkoxyalkyl, aryloxy, aralkoxy, arylthio, aralkylthio, alkylthioalkyl, arylthioalkyl, arylsulfinyl, aryl lsulfonyl, Haloalkylsulf onyl, haloalkylsulfinyl, Haloalkenyloxy-, Haloalkynyloxy-, Haloalkynylthiogruppe, Haloalkenylsulfonyl, Polyhaloalkenylsulfonyl, alkoxysulfonyl, aryloxysulfonyl, propargyloxy, aroyl, Halaazyl, Polyhaloazyl, Aryloxykarbonyl, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, arylaminosulfonyl, Karboxyalkoxy-, Karboxyalkylthio-, Alkoxykarbonylalkoxy-, Azyloxy, haloazyloxy, polyhaloazyloxy, aroyloxy, alkylsulphonyloxy, alkene-ylsulfonyloxy, arylsulfonyloxy, haloalkylsulfonyloxy, polyhaloalkylsulfonyloxy, aroylamino, haloazylamino, alkoxycarbonyloxy, arylsulfonylamino, aminocarbonyloxy, cyanato, Isocyanato, isothiocyanato, cycloalkylamino, trialkylammonium, arylamino, aryl (alkyl) amino, aralkylamino, alkoxyalkylphosphinyl, alkoxyalkylphosphinothioyl, alkylhydroxyphosphinyl, dialkyloxyphosphino, hydroxyamino, alkoxyamino, aryloxyamino, aryloxyimino, oxo, thfano, , Alkylaminoalkoxy, dialkylaminoalkoxy, alkoxyalkoxygr uppe, alkoxyalkenyl, cyanoalkoxy, dialkylsulfonium,

-X, - X, -X s5 Red - X-R-Λj

-XR ₃ , -P ^ -

^ Y ₃ R ₅

s.

Y ₃ R ₅

and

R-ig is a substituted or unsubstituted asymmetric heterocyclic ring system having at least three nitrogen atoms 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 is saturated or unsaturated in which the permissible substituents are identical or different and are one or more of the following: hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiozyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy , Aryldialkylsilyloxy, iaryllyilyloxy, formamidino, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminothio carbonyl, dialkylaminothiocarbonyl, hitro, cyano, hydroxycarbonyl and derived salts, loramamido, alkyl, alkoxy, polyhaloalkyl, polyhaloalkoxy, alkoxycarbonyl, substituted amino wherein the permissible substituents are the same or different and one or two of the following: propargyl, alkoxyalkyl, alkylthialkyl Alkyl, alkenyl, haloalkenyl or polyhaloalkenyl; Alkylthio, polyhaloalkylthio group, alkylsulfinyl, polyhaloalkylsulfinyl, alkylsulfonyl, polyhaloalkylsulfonyl, alkylsulfonylamino, alkycarbonylaminob, polyhaloalkylsulfonylamino, polyhaloalkylcarbonylamino, "trialkylsilyl, aryldialkylsilyl, triarylsilyl, suflonic acid and derived salts, phosphonic acid and derived salts, alkoxycarbonylamino, alkylaminocarbonyloxy, dialkylamine" okarboyl, nyloxy, alkenyl, polyhaloalkenyl, alkenyloxy, alkynyl, alkynyloxy, polyhaloalkenyloxy, polyhaloalkynyl, polyhaloalkynyloxy, polyfluoroalkanoyl, cyanoalkylatnino, semicarbazonomethyl, alkoxycarbonylhydrazonomethyl, alkoxyiminomethyl, unsubstituted or substituted aryloxyiminomethyl, hydrazonomethyl, unsubstituted or substituted arylhydrazonomethyl, one with a mono- , Di- or polysaccharide condensed hydroxy group, haloalkyl, halolakenyl, haloalkynyl, alkoxyalkyl, aryloxy, Ai-alkoxy, arylthio, aralkylthio, alkylthioalkyl, arylt hioalkyl, arylsulfonyl, arylsulfinyl, haloalkylsulfinyl, haloalkylsulfonyl, Haloalkenyloxy-, Haloalkynyloxy-, Haloalkynylthiogruppe, Haloalkenylsulfonyl, Polyhaloalkenylsulfonyl, alkoxysulfonyl, aryloxysulfonyl, propargyloxy, aroyl, Haloazyl, Polyhaloazyl, Aryloxykarbonyl, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, arylaminosulfonyl, Karboxyalkoxy-, Karboxyalkylthio-, Alkoxycarbonylalkoxy, azyloxy, Haloazyloxy, Polyhaloazyloxy, Aroyloxy, Allglsulf onyloxy, Alkenylsulfonyloxy, Arylsulfonyloxy, Haloalkylsulfonyloxy, Polyhaloalkylsulfonyloxy, Aroylamino, Haloazylamino, Alkoxycarbonyloxy, Arylsulfonylamino, Aminocarbonyloxy, Cyanato, Isocyanato , Isothiocyanato, cycloalkylamino, trialkylammonium, arylamino, aryl (alkyl) amino, aralkylamino, alkoxyalkylphosphinyl, alkoxyalkylphosphinothioyl, alkylhydroxyphosphinyl, dialkoxyphosphino, hydroxyamino, alkoxyatnino, aryloxyamino, aryloxyimino, oxo, thiono, alkylaminoalkoxy , Dialkylaminoalkox y, alkoxyalkoxy, alkoxyalkenyl, cyanoalkoxy, dialkylsulfonium,

-X, = X, -X = R ₃ , = XRj,

γ Y

I ₃ R ₅

^Y 3 ^R 5

, ^Y 2 ^R 4

wherein:

R is a substituted or unsubstituted karbocyclic or heterocyclic ring system selected from a monocyclic aromatic or nonaromatic

Ring system, a cyclic aromatic or non-aromatic ring system, a polycyclic aromatic or nonaromatic ring system and a bridging ring system which may be saturated or unsaturated in which the permissible substituents are the same or different and one or more of the following: hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl , Alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, shiozyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxy, formamydio, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino, aminocarbonyl, alkylaminocarbonyl , Dialkylaminocarbonyl, aminothiocarbonyl, Alkylaminothiokarbpnyl, dialkylaminothiocarbonyl, Ilitro-, cyano group, hydroxy carbonyl and derived salts, Pormamido group, alkyl, alkoxy group, polyhaloalkyl, polyhaloalkoxy, alkoxycarbonyl, substituted amino group, in we lcher the permissible substituents the same or different. and one or two of the following are: propargyl, alkoxyalkyl, alkylthioalkyl, alkyl, alkenyl, haloalkenyl or polyhaloalkenyl; alkylthio, polyhaloalkylthio, alkylsulfinyl, polyhaloalkylsulfinyl, alkylsulfonyl, polyhaloalkylsulfonyl, alkylsulfonylamino, alkylcarbonylamino, polyalkylsulfonylamino, polyhaloalkylcarbonylamino, trialkylsilyl , Aryldialkylsilyl, triar'ylsilyl, sulphonic acid and derived salts, phosphonic acid and derived salts, alkoxycarbonylamino, alkylaminocarbonylcsy, dialkylaminocarbonyloxygygroup, alkenyl, polyhaloalkenyl, alkenyloxy group, alkynyl, alkynyloxy, polyhaloalkenyl, polyhaloalkynyl, polyhaloalkynyloxy group, polyfluoroalkanol, cyanoalkylamino group, semicarbazonomethyl, alkoxycarbonylhydrazonomethyl, Alkoxyiminomethyl, unsubstituted or substituted aryloxyiminomethyl, hydrazonomethyl, unsubstituted or substituted arylhydrazonomethyl, a mono-, di-, or polysaccharide-fused hydrox ygroup, haloalkyl, haloalkenyl, haloalkynyl, alkoxylalkyl, aryloxy, aralkoxy, arylthio, aralkylthio, alkylthioalkyl, arylthioalkyl, arylsulfinyl, arylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, haloalkenyloxy, haloalkynyloxy, haloalkynylthio, haloalkenylsulfonyl, poly-haloalkenyl-r sulfonyl, alkoxysulfonyl, aryloxysulfonyl, propargyloxy, aroyl, haloazyl, polyhaloazyl, aryloxycarbonyl, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, arylaminosulfonyl, carboxyalkoxy, carboxyalkylthio, alkoxycarbonylalkoxy, azyloxy, haloazyloxy, polyhaloazyloxy, aroyloxy, alkylsulfonyloxy, Alkenylsulfonyloxy, arylsulfonyloxy, haloalkylsulfonyloxy, polyhaloalkylsulfonyloxy, aroylamino, haloazylamino, alkoxycarbonyloxy, arylsulfonylamino, aminocarbonyloxy, cyanato, isocyanato, isothiocyano, cycloalkylamino, trialkylammonium, arylamino, aryl (alkyl) amino, , Aralkylamino, alkoxyalkylphosphinyl, alkoxyalkylphosphinothioyl, alkylhydroxyph osphinyl, dialkoxyphosphino, hydroxyamino, alkoxyamino, aryloxyamino, acryloxyimino, oxo, thiono, alkylaminoalkoxy, dialkylaminoalkoxy, alkoxyalkoxy, alkoxyphenyl, cyanoalkoxy, dialkylsulfonium,

-X, = X, -X = Ro, = X-R ,,

^Y 1

-X - R ₃ , - P - YgR ^. »~

Ϊ1

^£ 3 ^R 5

or

R "is a substituted heteroatom or a substituted carbon atom, or a substituted or unsubstituted, branched or straight chain containing two or more carbon atoms or heteroatoms in a single or random combination in which the permissible substituents are the same or different and one or more of the following: Hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiozyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, aryldialkylsilyl

oxy, trialkylsilyloxy, formamidino, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, amino thiocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, nitro, cyano, hydroxycarbonyl and derived salts, formamido, alkyl Alkoxy group, polyhaloalkyl, polyhaloalkoxy group, alkoxycarbonyl, substituted amino group in which the permissible substituents are the same or different and one or two of the following: propargyl, alkoxyalkyl, alkylthioalkyl, alkyl, alkenyl, haloalkenyl or polyhaloalkenyl; Alkylthio, Polyhaloalkylthiogruppe, alkylsulfinyl, Polyhaioalkylsulfinyl, alkylsulfonyl, Polyhaloalkylsulfonyl, alkylsulfonylamino, Alkylkarbonylamino-, Polyhaloalkylsulf onylamino-, Polyhaloalkylkarbonylaminogruppe, trialkylsilyl, Aryldialkjasilyl, triarylsilyl, sulfonic acid and phosphonic acid and salts derived salts derived, AIkoxykarbonylamino-, Alkylaminokarbonyloxy-, Dialkylaminokarbonyloxygruppe, alkenyl , Polyhaloalkenyl, alkenyloxy group, alkynyl, alkynyloxy, polyhaloalkenyloxy group, polyhaloalkynyl, polyhaloalkynyloxy group, polyfluoroalkanol, cyanoalkylamino group, semicarbazonomethyl, alkoxycarbonylhydrazonomethyl, alkoxyiminomethyl, unsubstituted or substituted aryloxyiminomethyl, hydrazonomethyl, unsubstituted or substituted arylhydrazonomethyl, one with a mono-, di- or EL-saccharide condensed hydroxy group-e, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, aryloxy, aralkoxy, .arylthio, arakylthio group, alkylthioalkyl, arylthio alkyl, arylsulfinyl, arylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, Haloalkenyloxy-, Haloalkynyloxy-, Haloalkynylthiogruppe, Haloalkenylsulfonyl, Polyhaloalkenylsulfonyl, alkoxysulfonyl, aryloxysulfonyl, propargyloxy, aroyl, Haloazyl, Polyhaloazyl, Aryloxykarbonyl, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, arylaminosulfonyl, Karboxyalkoxy-, Karboxyalkylthio-, Alkoxycarbonylalkoxy, azyloxy, haloazyloxy, polyhaloazyloxy, aroyloxy, A'-alkylsulphonyloxy, alkenylsulphonyloxy, arylsulphonyloxy, haloalkylsulphonyloxy, polyhaloalkylsulphonyloxy, aroylamino, haloazylamino, alkoxycarbonyloxy, arylsulphonylamino, aminocarbonyloxy, zaynato, Isocyanato, isothiocyanato, cycloalkylamino, trialkylammonium, arylamino, iryl (alkyl) amino, aralkylamino, alkoxyalkylphosphinyl, alkoxyalkylphosphinothioyl, alkylhydroxyphosphinyl, dialkoxyphosphino, hydroxyamino, alkoxyamino, aryloxyamino, aryloxyimino, oxo, thiono, alkylaminoalkoxy , Dialkylaminoalkoxy, Alkoxyalkoxy group, alkoxyalkenyl, cyanoalkoxy group, dialkylsulfonium,

-A, = A, -AW ₃₁ - AK ₃ ,

Y ₃ R ₅

Y ₁ and Y. are independently oxygen or sulfur;

Y "and Y _{3 are} independently oxygen, sulfur, amino or a divalent bond, and

R. and Rg are independently hydrogen or substituted or unsubstituted alkyl, polyhaloalkyl, phenyl or benzyl, the permissible substituents being the same or different and one or more of the following: hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio , Thiozyanao-jPorpargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxy, lmmamidino, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy,

Amino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, hitro, cyano, hydroxycarbonyl and derived salts, formamido, alkyl, alkoxy, polyhaloalkyl, polyhaloalkoxy, alkoxycarbonyl, substituted amino in which the permissible substituents are the same or different and one or two of the following are: propargyl, alkoxyalkyl, alkylthioalkyl, alkyl, alkenyl, haloalkenyl or polyhaloalkenyl; Alkylthio, PoIyhaloalkylthiogruppe, alkylsulfinyl, polyhalo & lkylsulfinyl, alkylsulfonyl, Polyhaloalkylsulfonyl, alkylsulfonylamino, Alkylkarbonylamino-, Polyhaloalkylsulfonylatnino-, Polyhaloalkylkarbonylaminogruppe, trialkylsilyl, aryldialkylsilyl, triarylsilyl sulfonic acid and derivative salts, phosphonic acid and derivative salts, Alkoxykarbonylatnino-, Alkylaminokarbonyloxy-, Dialkylaminokarbonyloxygruppe, alkenyl, Polyhaloalkenyl, alkenyloxy group, alkyityl, alkynyloxy, polyhaloalkenyloxy group, polyhaloalkynyl, polyhaloalkynyloxy group, polyfluoroalkanol, cyanoalkylamino group, semicarbazonomethyl, alkoxycarbonylhydrazorioethyl, alkoxyiminomethyl, unsubstituted or substituted aryloxyiminomethyl, hydrazonomethyl, unsubstituted or substituted arylhydrazonomethyl, a hydroxy, condensed with a mono-, di- or polysaccharide, Haloalkyl, halolakenyl, haloalkynyl, alkoxyalkyl, aryloxy, aralkoxy, aralthio, aralkylthio, alkylthioalkyl, arylthio alkyl, Aryleulfinyl, arylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, HaIoalkenyloxy-, Haloalkynyloxy-, Haloalkynyothiogruppe, HaIoalkönylsulfonyl, Polyhaloalkenylsulfonyl, Alkoxysulfonyl, aryloxysulphonyl, propargyloxy, .Aroyl, Haloazyl, PoIyhaloaayl, Aryloxykarbonyl, aminosulfonyl, alkylaminosulfonyl, · dialkylaminosulfonyl, arylaminosulfonyl, Karboxyalkoxy-, KarboHyalkylthio Alkoxycarbonylalkoxy, azyloxy, haloazyloxy, polyhaloazyloxy, aroyloxy, alkylsulphonyloxy, alkenylsulphonyloxy, arylsulphonyloxy, haloalkylsulphonyloxy, polyhaloalkylsulphonyloxy, aroylamino, haloazylamino, alkoxycarbonyloxy, arylsulphonylamino, aminocarbonyloxy, cyanato, Isocyanato, isothiocyano, cycloalkylamino, täalkylammonium, arylamino, aryl (alkyl) amino-aralkylamino, alkoxyalkylphosphinyl, alkoxyalkylphosphinothioyl, alkylhydroxyphosphinyl, dialkoxyphosphino, hydroxyamines, alkoxyamino, aryloxyamino, aryloxyimino, oxo, thiono, alkylaminoalkoxy , Dialkylaminoalkoxy, Alkoxyalkoxy, alkoxyalkenyl, cyanoalkoxy, dialkylsulfonium,

"V _ -r -r TJ - _r j,

"Λ η - Λ." * Λ. ⁼ JX, β ~ A. ~ t

, 4 -Y ₂ H ₄ , -Y ₄ -PY ₂ R ₄ YR Y ₃ R ₅

Y ₃ R ₅

^Y 3 ^R 5

The heterocyclic nitrogen-containing compounds encompassed by the formula Λ can be prepared by conventional techniques known to those skilled in the art, and many are also available from various manufacturers. The novel heterocyclic nitrogen-containing compounds of formulas (i) through (xxxiii) above which can be used in the method of the present invention can be prepared by the reaction of suitable starting ingredients by the conventional methods described in the literature, such as US Pat shown below.

The novel heterocyclic nitrogen-containing compounds of formula (i) can be prepared according to the following general reaction scheme:

^R 24 " ^X 10 ^H -

I /

^R 24 " ^X 10

Scheme I

wherein R ₂₄ , X ₁₀ , a, j and Y _{19 are} as defined above. Reactions of this general type for the preparation of substituted pyridines, including the process conditions, are described, for example, by Mertel, HH, The Chemistry of Heterocyclic Compounds, Pyridines and Derviatives - Part Two, Halopyridines (The Chemistry of Heterocyclic Compounds, Pyridine and Derivatives - Part Two, Halopyridines ), P. 351, Interscience, Wiley, Hew York (1961). Intermediates such as 2,4,6-trichloropyridine are described in U.S. Patent 3,830,820. Other preparation methods for the novel compounds of formula (i) are described in Fuson, R.C., Advanced Organic Chemistry, p. 124, Wiley, New York (1950), and Ochiai, S., Aromatic Amine Oxides (Aromatic Amine Oxide), p. 21, Elsevier, Hew York (I967).

The novel heterocyclic, nitrogen-containing compounds of the formula (ii) can be prepared according to the following general reaction scheme:

R ₂₅ - X ₁₁ H

(γ

20 * b

R _ocr

Scheme II

wherein R

25 '

b and Yp _{0 are} as defined above. Reactions of this general type for the preparation of substituted pyrazines, including the process conditions. are described, for example, in US Pat. No. 4,254,125.

The novel heterocyclic nitrogen-containing compounds of formula (iii) can be prepared according to the following general reaction scheme:

26 "" Scheme III

H + ·

- X

22 wherein R

• 26 '

^L 12 '

'2V

Y ₂₂ and

as defined above and

Yg is halogen. Reactions of this general type for the preparation of 2-substituted pyrimidines, including the process conditions, are described, for example, by Hurst, DT, Introduction to the Chemistry and Biochemistry of Pyrimidines, Purines and Pteridines (Introduction to the Chemistry and Biochemistry of Pyrimidines, Purines and Pteridines), pp. 49-53, Wiley, Hew York (1980). Intermediates in which Y ₂₁ and Y _{23 are} an alkylthio group are described by Eilingsfeld, H. and Schevermann, H., Chem. Ber., 100 , pp. 1874-1891 (1967). Other preparation methods for the novel compounds of the formula, (iii), such as the Rembry-Hull pyrimidine synthesis, are described by Brown, DJ, The Pyrimidines; The Chemistry of Heterocyclic Compounds, p98, I69-170, 166, Interscinece, Wiley, Hew York (1960).

The novel heterocyclic nitrogen-containing compounds of formula (IV) can be prepared according to the following general reaction scheme:

- X ₁₃ H + Y

49 '

M /

 / 'S

 24

^{I #} 26 ^xY 25

R ₂₇

 24

26 ^Y 25

Scheme IV wherein R,

Y ₂₆ and Y ₄₉

as defined above

27 '13' 24 '25' are. Reactions of this general type for the preparation of 4-substituted pyrimidines, including the process conditions, are described, for example, by Josima, T. et al. Sankyo Kenkyusho Hewpo, ^ 2, pp. 114-120 (1980). ,

The novel heterocyclic nitrogen-containing compounds of formula (v) can be prepared according to the following general reaction scheme:

, γ

29

Scheme V

/) ™ ^H0 -

wherein R _o

Y " ₈ and

as defined above.

^Λ 28 · ^Λ 14 'x 27' Reactions of this general type for preparing 5-substituted pyrimidines, including the process conditions and the preparation of intermediates, wer_ the (for example, Fieser, 1. F. and Fieser, H., Organic Chemistry Organic Chem.), P. 310, Heath, Boston (1972), and also by Brown, DJ, The Pyrimidines, The Chemistry of Heterocyclic Compounds, p. 50, 166, Interscience, Wiley, New York (1962). The novel heterocyclic nitrogen-containing compounds of formula (vi) can be prepared according to the following general reaction scheme:

Y ₄₉

Y Y '

 32

YY 30/31

'K = H

Scheme VI

₃₀ ,

and

as defined above

are. Reactions of this general type for the preparation of 3-substituted pyridazines, including the process conditions and the preparation of intermediates, are described, for example, by Jojima, T., et al., Agric. Biol. Chem., 21 (11) » ¹ 376-1381 (1968), and Eilingsfeld, H. and Schevermann, H., Chem. Ber., 100 . 1874-1891 (1967).

The novel heterocyclic nitrogen-containing compounds of formula (vii) can be prepared according to the following general reaction scheme:

Scheme VII wherein R ₃

Y ₃₄ , Y ₃₅ and Y ₄₉

as defined above

^ 30 '16' ^± 3V . Reactions of this general type for the preparation of 4-substituted pyridazines, including process conditions and the preparation of intermediates, are described, for example, by Jojime, T., et al., Agric. Biol. Chem. J32 (11), 1376-1381 (1968).

Novel heterocyclic nitrogen-containing compounds of formula (viii) can be prepared according to the following general reaction scheme:

Scheme VIII

where Y,

R

and X

as defined above

37 x 38 '' ^ 49 ^{'= "1Ι} 31 are defined." Reactions for the preparation of this general type of substituted 1,3,5-triazines, including the process conditions and the preparation of intermediates, for example in German Patent 952,478, in U.S. Patent 2,824,823 to Koopraan, H., et al., Rec. Trav. Chim., JQ, 967-980 (1959), Drabek J. and Skrobal, M., Chem. Zvesti, 17, (7), 482 - 487 (1963), Hirt, R. et al., '

Helv. Chim. Acta, 33, 1365 (1950) and German Patent 1,076,696. Other preparation methods for the novel compounds of formula (viii) are disclosed in U.S. Patent Nos. 4,220,765, 2,696,019 and Chakrabarti, J.K. a., J. Chem. Soc. 861 (1974).

The novel heterocyclic nitrogen-containing compounds of formula (ix) can be prepared according to the following general reaction scheme:

(R ₃₂ ) _f

Scheme X

Scheme IX

wherein R ₃₂ , f, X ₁₈ , Y ₃₉ , ₄₀ and Y _{41 are} as defined above. Reactions of this general type for the preparation of substituted 1,3,5-triazines, including process conditions and the preparation of the intermediates, are described, for example, in U.S. Patent 3,316,264. Intermediates such as 2,4-dichloro-6- (diethoxyphosphinyl) -1,3,5-triazine are described in Japanese Patent 74 46635. Other preparation methods for the novel compounds of formula (ix) are described by Mendoza, CE et al., J. Ag. Food Chem., Jj., (1), 41-45 (1972). ,

The novel heterocyclic nitrogen-containing compounds of formula (x) can be prepared according to the following general reaction scheme:

^L 41

K 'V ^h - ^:

X ₁₉ -H

^L 41

19X _- . where Y

41 '42'

Y ₄₉ and

as defined above. reaction

Such general type of preparation of bis-1,3,5-triazines, including process conditions and intermediates, conforms to the procedures used to prepare the above compounds of formula (viii).

The hay heterocyclic nitrogen-containing compounds having the formula (xi) can be prepared according to the following general reaction scheme:

Ά J

^L 54

Scheme XI

and Υ. "as defined above.

_ 'S' ^Χ 20 · ^Υ 52 '

Reactions of this general type for the preparation of substituted 1,3,5-triazines, including the process conditions and the preparation of the intermediates, correspond to the procedures used above for the preparation of compounds of formula (viii). Other preparation methods for the novel compounds of formula (xi) are described by Allen, CFH and Convers, S., Org. Syn. Coll., Vol. I, 226-227, U.S. Patent 1,911,689, to Bessiere-Chretien, Y. and Serne, H., Bull. Soc, China. France, (6), Part 2, 2039-2046 (1973), Japanese Patent 28,101, Japanese Patent 28,100, Japanese Patent 28,098, Japanese Patent 9155, Loew, P., and Weis, CD, J. Heterocyclic Chem., JjS, 829-833 (1976) and Richter, GH, Textbook of Organic Chemistry, p. 486, Wiley, New York (1967).

^l 42

The novel heterocyclic nitrogen-containing compounds of formula (xii) can be prepared according to the following general reaction scheme: '

Scheme ZII

45

'46

R ₃₅ -X.

45

'46

wherein R ₃₅ , X ₂₁ , Y ₄₅ , Y ₄₆ and Y _{49 are} as defined above. Reactions of this general type for the preparation of heterocyclic substituted 1,3,5-triazines, including process conditions and the preparation of intermediates, are in accordance with the procedures used above for the preparation of compounds of formula (viii). Other preparation methods for the novel compounds of formula (xii) are described by Koopman, H. and Daams, J., Rec. Trav, Chim., H, 235-240) 1958) and British Patent 908,352.

The novel heterocyclic nitrogen-containing compounds of formula (xiii) can be prepared according to the following general reaction scheme:

Vf

X ₃₇

R-

Scheme XIII

wherein R

37 ^!

R ₃₈ , B ₁₄ and Y ₄₇

as defined above. Reactions of this general type for the preparation of substituted azoles, including process conditions and the preparation of intermediates, are described, for example, by Hautzsch, A., Chem. Ber., 2Tj-495 (1981), Adembri, G., and Tedeshi, P. , Bull, Sei. Facul. Ghim. Ind. Bologna, 2,3, 203 (1965) and Carr, J.B. and others, J. Med. Chem., 20, (7), 934-939 (1977).

The novel heterocyclic nitrogen-containing compounds of formula (xiv) can be prepared according to the following general reaction conditions:

Scheme XIV

wherein 1 * 37> ^ 38 ' ^B 14 ^ ¹⁰ - ^ 47 are ^as defined ^above . Reactions of this general type for the preparation of substituted azoles, including process conditions and the preparation of intermediates, are described by Pahanayak, BK, J. Ind. Chem. Soc., £ 5. (3), 264-267 (1978) and Young, TS and Amstutz, 3rd D., J. Amer. Chem. Soc., 12, 4773-4775 (1951). Other methods of preparing the novel compounds of formula (xiv) are described by Tripathi, H. et al., Agric Biol. Chem., 37, 1375 (1973), and Young, TE and Amstutz, ED, J. Amer. Chem. Soc. 13, 4773-4775 (1951).

The novel heterocyclic nitrogen-containing compounds of formula (xv) can be prepared according to the following general reaction scheme:

Scheme XV

wherein R

 41 '

and

as defined above. Reactions in which R.

and Y. _Q as defined above

of this general type for the preparation of substituted 1,2,4-azoles, including the process conditions and the preparation of intermediates, are described by Selim, M. and Selim, M., Bull. Soc. Chim. France, 1219-1220 (1967).

The novel heterocyclic nitrogen-containing compounds of the formula (xvi) can be prepared according to the following general reaction scheme:

15 R

42

Scheme XVI

₄₂ ,

R4'2

and Y.Q are as defined above, reactions of this general type for the preparation of substituted 1,3,4-azoles, including process conditions and the preparation of intermediates, are described by Koopman, H.E. a., Rec. Trav. Chim., 78, 967-980 (1959). A useful intermediate is described in British Patent 913,910.

The novel heterocyclic nitrogen-containing compounds of the formula (xvii) can be prepared according to the following general reaction scheme:

45 ' ^ri 46' 47 '^ 48'"16""" ^ 48 are. Hecations of this general type for the preparation of substituted benzazoles, including process conditions and the preparation of intermediates, are described by Hugershoff, A., Chem. Ber., J! 6, 3121-3134 (1903), and Young, ET and Amstutz, E, D., J. Atner. Chem. Soc., 3, 4773-4775 (195).

The novel heterocyclic nitrogen-containing compounds of the formula (xviii) can be prepared according to the following general reaction scheme:

, ^R 48 Scheme XVIII

in which R.

^R 4

and

as defined above

_ * ₄ 6 '' 47 '-.--is.. Reactions of this general type for preparing substituted benzisoxazoles, including the process conditions and the preparation of the intermediates, are described in Comprehensive Heterocyclic Chemistra (Comprehensive heterocyclic chemistry), Volume 16, S 58, Pergamon Press, New York (1984).

The novel heterocyclic nitrogen-containing compounds of the formula (xix) can be prepared according to the following general reaction scheme:

hA \

Scheme XVII

Scheme XIX

wherein R ₁₅₀ , Β-γ, Y ₅ , Y ₅₅ and Y _{49 are} as defined above. Reactions of this general type for the preparation of substituted 1,3,5-triazines, including process conditions and the preparation of intermediates, correspond to the procedures used for the preparation of compounds of formula (viii) above. Other preparation methods for the novel compounds of formula (xix) are described by Beech, WF, J. Chem. Soc, (C), 4 "S6-472 (1967).

The novel heterocyclic nitrogen-containing compounds of the formula (xx) can be prepared according to the following general reaction scheme:

or-

Scheme XX

wherein R _c

B "

and Y.Q as defined above

^Λ "51 ^a 18""19" ^X 56 ". Reactions of this general type for preparing substituted 1,3,5-triazines, including process conditions and the production of the intermediate products corresponding to the methods with above for the preparation of compounds of general formula (viii).

The novel heterocyclic nitrogen-containing compounds of the formula (xxi) can be prepared according to the following general reaction scheme:

58

wherein B ₂₀ , Y ₅₈ , Y ^ and Y. ^ are as defined above. Reactions of this general type for the preparation of substituted 1,3,5-triazines, including process conditions and the preparation of intermediates, correspond to the procedures used above for the preparation of compounds of formula (viii).

The novel heterosyclic nitrogen-containing compounds of the formula (xxii) can be prepared according to the following general reaction scheme:

^L 60

Scheme XXII . ·

wherein R53 '- ^ ♦ 25 ^Y 60' ^Y 61 ""^"1 ^ ^ 49 ^as defined ^otlen reactions of this general type for the preparation of substituted 1,3,5-triazines, including the process conditions and the preparation of the intermediates. correspond to the procedures used above for the preparation of compounds of formula (viii ').

The novel, heterocyclic nitrogen-containing compounds of the formula (xxiii) can be prepared according to the following general reaction scheme:

Scheme XXIII

wherein R ₁ -

X.

26 '

Y ₅₀ and Y ₅₁

as defined above. reaction

tions of this general type for the manufacture of

xyhydro-1,3,5-triazines, including the process conditions, are described, for example, by Meyers, A.I. a., J. Amer. Chem. Soc., 21, 763 (1969). The preparation of suitable intermediates corresponds to the procedures used for the preparation of the above compounds of formula (viii).

The novel heterocyclic nitrogen-containing compounds of formula (xxiv) can be prepared according to the following general reaction scheme:

Z "Y

R ₆₈ -X ₂₇ -HH _{2 +} θ

AcOH

^Z 2 ^Y 68

^Z 2 ^Y 68

Scheme X) LIV

Yg ₇ and Yg ₈ "are defined above.

Reactions of this general type for the preparation of substituted maleimides, including the process conditions and the preparation of intermediates, are described, for example, in Japanese Patent 75,117,929. Other preparation methods for the novel compounds of the formula (xxiv) are described in US Pat. No. 3,129,225 and in Japanese Pat. No. 75,132,229.

The novel heterocyclic nitrogen-containing compounds of the formula (xxv) can be prepared according to the following general reaction scheme:

^R 69 ~ ^X 28 "

wherein R, -

Z.

Y_ and _o are as defined above.

^Λ 69 '' 28 ^'and y * 4' Reactions of this general type for the manufacture of substituted maleimides, including the process conditions and the production of intermediate products corresponding to the methods employed for the preparation of the above compounds of formula (xxiv) become.

The novel heterocyclic nitrogen-containing compounds of the formula (xxvi) can be prepared according to the following general reaction scheme:

^R 7O " ^X 29 ^{rI <}

Scheme XXVI

wherein R ₇₀ , X ₃₉ , Z ₅ ,

and Y _{72 are} as defined above.

Reactions of this general type for the preparation of substituted maleimides, including process conditions and the preparation of intermediates, are in accordance with the procedures used above for the preparation of compounds of formula (xxiv).

The novel heterocyclic, nitrogen-containing compounds of the formula (xxvii) can be prepared according to the following general reaction scheme:

R "- X" q-NHp +

Scheme XXVII

^Z 8 ^Y 74

AcOH

wherein R ^, Xqq »Z ₇ , Z _g , Y ₇₃ and Y ₇ . as defined above. Reactions of this general type for the preparation of substituted maleimides, including the process conditions and the preparation of intermediates, corresponding to

the methods used above for the preparation of compounds of formula (xxiv).

The novel heterocyclic nitrogen-containing compounds of the formula (xxviii) can be prepared according to the following general reaction scheme:

" n?

AOOH

10

10

and

as defined above. Re-

Scheme XXVIII wherein B _21, Z _9, Z _10, X ₇₅ Actions of this general type for preparing substituted maleimides, including the process conditions and the production of intermediate products are carried out according to the process for the preparation of the above compounds of formula (xxiv) ,

The novel heterocyclic, nitrogen-containing compounds. fertilizers of the formula (xxix) can be prepared according to the following general reaction scheme:

Scheme XXIX

wherein R _n

Y ₇₈ and

as defined above.

^V 72 '31' 11 ' ^x The suitable halogenating agents include, for example, PCl ₅ , POCl ₃ , PBr ₅ and POBr ₃ and mixtures thereof. Reactions of this general type for the preparation of substituted pyridazinones, including the process conditions and the preparation of intermediates, are described, for example, in Yuki Gosei Kagaku Kyotai Shi 28, (4), 462-463 (1970). Other preparation methods for the novel compounds of the formula (xxix) are described in Yakugaku Zasshi 86, (12), 1168-1172 (1966), Acta DoI. Pharm. 36 (3), 301-306 (1979), U.S. Patent 2,963,477, Japanese Patent 6,822,309, Org. Prep. Proced. Int. 17, (2), 107-114 (1985), Arm. Khim. Zh. 21 (6), 515-520 (1968) and in German Patent 1,948,550.

The novel heterocyclic nitrogen-containing compounds of the formula (xxx) can be prepared according to the following general reaction scheme:

R ₇₃ -X ₃₂ -NHHH ₂ +

Scheme XXX

wherein R _73, X ₃₂ ^»z i _2» ^ 80 ^'Y 81 ¹ ^ ^ 82 ^{as otien} are defined. "Reactions of this general type for preparing substituted pyridazinones, including the process conditions and the preparation of intermediates, corresponding to the above-mentioned methods for the preparation of compounds of the formula (xxix).

The novel heterocyclic nitrogen-containing compounds of the formula (xxxi) can be prepared according to the following general reaction scheme:

HCl

^R 74 " ^X 33" ¹ \

"62

 -PY

"74 '

^X 83 '

and Yg, as defined above

are. Reactions of this general type for the preparation of substituted pyridazinones, including the process conditions and the preparation of intermediates, correspond to the procedures used above for the preparation of compounds of the formula (xxix).

The novel heterocyclic nitrogen-containing compounds of the formula (xxxii) can be prepared according to the following general reaction scheme:

R ₁ XH + Y ₄₉ - R ₃₆ > R ₁ -XR ₃₆

Scheme XJCXII

wherein R ₁ , X, R, ₆ and Y ^ q are as defined above, reactions of this general type for the preparation of substituted asymmetric compounds, including process conditions and the preparation of intermediates, conform to the procedures described above for the preparation of Compounds of formula (viii) can be used using the appropriate starting materials.

The novel heterocyclic, nitrogen-containing compounds of the formula (xxxiii) can be prepared according to the following general reaction scheme: -H ₊ / _x

Y ^ H

^L 64

65

Scheme XXXIII

wherein R ₁

^Y 65

and X as defined above

62 ' ^I 63' ^X 64 * ^X 65 '. Reactions of this general type for the preparation of substituted cyclotriphosphazenes, including the process conditions and the preparation of intermediates, correspond to the procedures used for the preparation of the above compounds of formula (viii) using the appropriate starting materials.

The above are illustrative other methods that can be used to prepare the heterocyclic nitrogen-containing compounds encompassed by the formula J _- , for example, in the following sources: Italian Patent 589,543, Italian Patent 588,280, British Pat. No. 872,313, Canadian Patent No. 659,610, PCT application AU81 / 00046, U.S. Pat. No. 3,203,550, U.S. Pat. No. 3,931,165, U.S. Pat. No. 2,720,480, U.S. Pat. No. 4,038,197, U.S. Pat. U.S. Patent 3,682,903, U.S. Patent 3,775,406, U.S. Patent 3,932,167, U.S. Patent 4,390,538, U.S. Patent 3,361,746, U.S. Patent 4,414,221, U.S. Patent 4,237,127, U.S. Patent 3,951,971 and U.S. Patent 3,973,947.

It has been found that the antiperspirant compounds of formula 1_ substantially reduce the water consumption by Pllanze and fruit, d. h., lower the transpiration rate and increase the resistance of the plant leaf surfaces to the loss of moisture vapor, d. h., increase the diffusion resistance. In addition, the antiperspirant compounds used in the present invention do not substantially inhibit the photosynthetic, light-requiring reactions, are substantially non-phytotoxic to the growing plants, and serve to reduce crop yields as compared to untreated ones

To increase plants under the same conditions, especially in areas where the plants are exposed to moisture conditions. The antiperspirant compounds used in the present invention serve to maintain soil moisture by reducing water consumption by plant and crop at various developmental periods, e.g. During the vegetative period, whereby the unused water is available at other periods of plant or crop development, e.g. During the reproductive growth period.

As noted above, stomata are tiny stomata in the epidermis of the plant leaf surfaces through which gas exchange occurs between the atmosphere and the intercellular spaces within the leaf. It is believed that the antiperspirant compounds of formula J_ effectively lower the transpiration patches of the plants by closing the plant stomata or narrowing the stomata of the plants to such an extent that the loss of moisture is reduced, and moreover the compounds are substantially noxious The photosynthetic process in plants consists of light-demanding reactions, ie light reactions, and non-light-sensitive reactions, ie, dark reactions · The dark reactions generally involve a complex of enzyme-mediated reactions which cause the conversion of carbon dioxide into sugar. Weaving the carbon dioxide, the dark reactions need reducing power and chemical energy, which are generated and mediated by the light reactions. "In general, the photosynthesis of plants are associated with two light-demanding reactions, the commonly referred to as photosystem I and photosystem II. See, for example, Salisbury, F.B. and Ross, C.W., Plant Physiology (Plant Physiology), pp. 131-135 (1978). These photosystems are linked by an electron transport chain and provide the reducing power and the chemical energy for the dark reactions. The inhibition of one or both of these photosystems can adversely affect the photosynthesis, which can lead to plant damage or even death of the plant.

Thus, it has been found that the antiperspirant compounds used in the present invention cause no or substantially no inhibition of Photosystem I or Photosystem II. In contrast, it is known that the herbicide atrazine substantially inhibits the photosynthetic light reactions, in particular the electron transport chain. See, for example, Jachetta, JJ and Radosevioh, SR, Weed Science 29: 37-43 (1981). This herbicidal inhibition leads to a build-up of carbon dioxide within the leaf, which leads to the closing of the stomata. See, for example, Smith, D. and Buchholtz, KP, Plant Physiology 39: 572-578 (1964). Thus, in contrast to the antiperspirant activity of the compounds used in this invention, the antiperspirant activity of atrazine is associated with its herbicidal properties. The term "substantially no inhibition of the photosynthetic electron transport ¹¹ as used herein refers to no or little inhibition of photoxythetic electron transport.

Hereafter, an effective amount of a heterocyclic nitrogen-containing compound for reducing plant moisture loss is understood to be an antiperspirant effective amount of the invention which is sufficient to reduce the transpiration moisture loss of plants without substantially inhibiting photophysical electron transport of the plants. Also, by an effective amount of a heterogeneous cyclic nitrogen containing compound to increase crop yields, an amount of compound effective to increase yield is understood to be sufficient to increase crop yield without substantially inhibiting photosynthetic electron transport of the plant. In both cases, the effective amount of the compound may vary over a wide range, depending on the specific compound used in each case.

is dependent on environmental and climatic conditions and the like, provided that the amount of compound used does not result in substantial inhibition of the photosynthetic electron transport of the plant or substantial P.hytotoxicity, e.g. B. combustion of the plants, Ghlorose or necrosis, leading to the plant. In general, the compound may preferably be applied to plants and poppy crops at a concentration of about 0.113 to 2.267 kg of the compound per 4047 m, as described in more detail below.

The heterocyclic nitrogen-containing compounds set forth in Formula J _- may be employed in a variety of conventional ways known to those skilled in the art. Compositions containing the compounds as the active ingredient generally also consist of a carrier and / or diluent, in liquid or solid form.

Suitable liquid diluents or carriers are u. a. Water, petroleum distillates or other liquid carriers with or without surfactants. Liquid concentrates may be prepared by dissolving one of these compounds in a non-phytotoxic solvent such as acetone, xylene, nitrobenzene, cyclohexanone or dimethylformamide, and dispersing the active ingredients in water with the aid of suitable surface active emulsifying and dispersing agents.

The choice of dispersing and emulsifying agent and the amount employed are dictated by the nature of the composition and the ability of the agent to facilitate dispersion of the active ingredient. In general, it is desirable to use as little of the agent as possible, consistent with the desired dispersion of the active ingredient in the spray, so that the rain does not re-emulsify the active ingredient after it has been applied to the plant the plant is washed off. It is possible to use nonionic, anionic or cationic dispersants and emulsifiers, for example the condensation products of alkylene oxides with phenol and organic acids, alkylarylsulphites, complex ether alcohols, quaternary ammonium compounds and the like.

In the preparation of wettable powders or dust compositions, the active ingredient is dispersed in and on a suitably dispersed solid carrier such as clay, talc, bentonite, diatomaceous earth, fullers earth and the like. In the preparation of wettable powders, the above-mentioned dispersants as well as lignosulfonates may also be included.

The required amount of the active ingredient treated herein may be from 1 to 200 gallons (3.785 dm ³ to 757 dm ³ ) or more of the liquid carrier and / or diluent per acre treated (4047 m) or from about 5 to 500 pounds (about 2.267 to 226.7 kg) of wearing solid carrier and / or diluent can be used. The concentration in the liquid concentrate will typically vary between about 5 and 95 weight percent and will be between about 0.5 and about 90 weight percent for solid compositions. Satisfactory spray or dust for general use contains between about 0.1 and about 100 pounds (0.0454 to 45.359 kg) of the active ingredient per acre (4047 m), preferably between about 0.25 to about 15 pounds (about 0.113) to 6.804 kg) of the active ingredient per acre, and most preferably between about 0.5 to about 5 pounds (0.227 to 2.267 Iq) of the active ingredient per acre.

Optionally, compositions which are useful in the practice of the invention may also contain other ingredients, such as stabilizers or other biologically active ingredients, as long as they do not affect or reduce the activity of the active ingredient and damage the plant to be treated. The other biologically active compounds include, for example, one or more insecticidal compounds.

ticidal, herbicidal, fungicidal, nematocidal, miticidal compound, plant growth regulator or other known compounds. These combinations can be used for the known and other purpose of each ingredient and have an xynergistic effect.

The antiperspirant compounds of the formula I _- are preferably applied to the plants or crops under conditions of little or no water stress or under the conditions which may be termed average or normal growth conditions. A preferred condition for application of the compound is that of substantial moisture loss of the soil. Although the authors do not wish to be bound by any particular theory, it is believed that application of the antiperspirant compounds will not result in a reduction in the total minimum water requirement of a treated plant or crop, but the application of these compounds will serve to provide more effective watering by treated plants and crops bring about. It is believed that the antiperspirant effect does not reduce the total amount of water required for the growth of a given plant or crop, apart from water inputs possible with certain irrigated crops, but rather the antiperspirant effect Yields of the treated fruits, which are irrigated or irrigated, or only partially irrigated, compared to untreated fruits. ter similar conditions. In addition, the antiperspirant compounds of formula J _{- are} preferably applied to plants and fruits under conditions which favor large gradients in water vapor pressure between the saturated atmosphere within the leaf and the atmosphere around the leaf. These conditions include low humidity, high light / heat load of the sheet. and high rates of air movement.

In particular, it is believed that the application of the antiperspirant compounds of formula 1 to plants, for example, during the period of vegetative growth, reduces the amount of water the plant uses over a period of about 1 to 6 weeks, thereby providing a greater reservoir of water the other developmental periods of the plant, such as the critical reproductive growth phase, remain in the soil. This soil moisture maintenance can minimize any water deficiency in the plant tissues during critical developmental phases, such as the reproductive growth phase, thereby increasing yields. The antiperspirant compounds used in the present invention may also be used during the reproductive growth phase of the plant to achieve similar results.

In general, the Antitranspirationaverbindungen the formula J _- useful in reducing the need for irrigation water, especially in dry climates, in protecting the plants from withering or other damage during transplanting or transport or in very cold weather and to reduce water pollution under certain environmental conditions, as stated above. Such tetrahedra can be used in agriculture, horticulture and the like, and can be applied to plant growth such as evergreen shrubs, evergreen trees, trees and the like to protect them from dying in winter. One of the major causes of plant dying in winter is the excessive moisture loss of leaf surfaces on sunny or windy days when the soil is frozen and the root system can not replace water loss. The antiperspirant compounds may also be used in other ornamental plants such as roses and other flowers, Christmas trees and the like to maintain their freshness and delay the hading. Further, the antiperspirant compounds can be used to avoid or minimize the effects of summer blight and transplant shock.

In the light of the above, it has been recognized that the antitrarine compounds of formula I can also be used to control leaf diseases on such plants as wheat and oats. See, for example, Avant Gardener, Vol. 18, i <3 1, November 1985, where antiperspirants are used to combat fungal diseases.

The term crops here refers generally to agronomic or horticultural crops, ornamental plants and turf grasses. By way of illustration, for the plants which can be treated with antiperspirant compounds of the formula J _- treated by the method of this invention, quays, cotton, sweet potatoes, white potatoes, alfalfa * wheat, rye, highland rice, barley, oats, may be mentioned, for example. Sorghum, dried beans, soybeans, sugar beets, sunflowers, tobacco, tomatoes, canola, fruits of deciduous trees, citrus fruits, tea, coffee, olives, pineapple, cocoa, bananas, sugarcane, oil palms, perennial shrub plants, shrubs, grasses, ornamentals, evergreens Plants, trees, flowers and the like. Fruit is generally understood to mean any of the agricultural or horticultural fruits mentioned above. Transplanted material is generally understood to mean tobacco plants, tomatoes, egg plants, cucumbers, lettuce, strawberries, plants of perennial borders, wood shrubs, tree seedlings and the like.

The antiperspirant compounds proposed herein lower the transpiration moisture loss of plants and increase crop yields. These compounds have a high safety margin in that, when used in sufficient quantity to produce an antiperspirant effect or an enhancement effect, they do not inhibit the photosynthetic electron transport of the plant or burn or damage the plant, and they withstand weathering, which includes washout by rain, decomposition by, ultraviolet light, oxidation or hydrolysis in the presence of moisture or at least such decomposition, oxidation and hydrolysis which would substantially reduce the desirable antiperspirant property of the active ingredient or the transfer of undesirable properties such as phytotoxicity , on the active ingredients. If desired, mixtures of the active ingredients as well as combinations of the active compounds with other biologically active compounds or ingredients as set forth above may be employed.

The invention is illustrated by the following examples.

Example I:

Preparation of 2,4-dichloro-6- (4-methylphenylthio) -1,3,5-

triazine .

To a solution containing 18.4 g (0.1 mole) of cyanuric chloride in 200 ml of acetone was added, while cooling at a temperature of 0-5 ° C. with magnetic stirring, a solution containing 12.4 g (0. 1 mole) of 4-methylthiophenol and 10.7 g (0.1 mole) of 2,6-lutldine in 50 ml of acetone. The solution was added at such a rate as to keep the reaction temperature at 0 ° -5 ° C. The resulting mixture was magnetically stirred for 2 hours, allowed to warm to room temperature and washed with acetone after the precipitated 2,6-lutidine hydrochloride had been filtered out. The combined filtrates were then poured onto ice and the resulting precipitated solid was collected by filtration. The solid was washed with 100 ml of 10% aqueous HaOH and then with 100 ml of water. After drying, the solid was recrystallized twice from hexane to give a crude yield of 5 g. This material was further purified by vacuum sublimation to give 1.16 g (0.004 mol) of pure 2,4-dichloro-6- (4-methylphenylthio) -1,3,5-triazine having a melting point of 112 ° -114 ° C. Elemental analysis of the product gave the following values:

Analysis: C ₁₀ H ₇ Cl ₂ Ii ₃ S

Calculated: C - 44.13, H - 2.59, K - 15.44. Calculated: C - 44.24, H - 2.61, N - 15.34.

This compound will be referred to as Compound 1 below.

Example II:

Other compounds are prepared in the same manner as in Example I. The structures and analytical data for compounds 2 to 36 used in the examples below for the reduction of plant moisture loss are given in Table A below. Compound 18 was purchased from Maybridge Chemical Company, Limited, Trevillet, Tintagel, Cornwall, United Kingdom, was recrystallized three times from hexane.

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Table A, continued

Representative heterocyclic. nitrogenous compounds

, substituents ^X 1 ^Y 5 ^Y 6 ^Y 6 Ar1ementaranaIy a e H 1.55 N determined H  11 1.84 15.84 Melting point verb 1.76 3.18 14.69 C 1.95 14.35 3.43 11.28 ⁰ C IJ R ₁₂ 0 Cl Cl 2.48 14.79 43,60 2.65 14.58 0 Cl Cl calculated 2.70 18.73 47.47 3.00 x 18.58 3,4-OCH ₂ O- 0 Cl Cl C 2.45 14.58 43.82 2.38 14.31 i40 - 142 10 4-CH ₃ CO- 0 Cl Cl 41.98 1.50 20.98 41.12 1.62 20.98 137-139 11 3-CH ₃ COKH- 0 Cl Cl 46 ΰ 1.50 20.98 46.81 1.69 20.98 137-139. 12 4-CH ₃ S- 0 Cl Cl 44.17 3.55 13.46 45.28 3.69 13.83 121 - 123 13 4-CUE 0 Cl Cl 41.68 50,20 185-187 14 3-CiT 44.97 KIvIR (CDCIt ₁ ): ί 6.80 - 7 , 50 particles / mill. (M, 139 - 143 15 2-CH ₃ 0-4- 0 Cl Cl 44.97 aromatische.Protonen) 100-102 16 -CH ₂ CH = CH ₂ 50.02 41.57 16.16 42.05 3-I ¹ 0 Cl Cl 53.64. 11.04 53.53 83.5 - 84 17 0 Cl Cl 4_I? 107-108 18 4-C1-2- boiling point 19 CH (CH ₃ ) CgH ₅ 240/2 mm

labeile A, continued

Representative heterocyclic, nitrogen-containing compounds

- R ₁₂ X ₁ ^Y 5 Y ₆ R ₁₂ 38 determined 14.29 s, CH ₃ ), Melting point 38 NCH 12.98 ⁰ C 4-Cl S Cl Cl ßlementaranalyse 92 14.36 37.01 1, 13,00 Verb. Substituents 3-Cl S Cl Cl calculated 46 14.36 32.79 2, 15,01 116-118 .α 2,6-Cl ₂ S Cl Cl C H 45 12,85 33,23 O ₁ 14,60 101 - 102 4-F S Cl Cl 36.94 1, ): 15,22 37,32 1, (complex 114-116 20 4-CH ₃ O- S Cl Cl 36.94 1, 14.58 41.44 2, Multiplet, aromatic protons) 112-114 21 H 0 Cl Cl 33.05, ): S 7.07-7.60 particles / mill. (FROM- 98 - 100 22 39.15 1, Quartet, aromatic 112-114 23 4-Cl 0 Cl Cl 41.68 2, ): 5 3.85 particles / mill. 24 HMR (CDCl ₃ 3 protons) 108-111 25 4-CH ₃ 0 Cl Cl , 38 , (3Η, KMR (CDCl ₃ , 44. 90 - 93 26 , 73 HIR (CDCIo , 69 27 , 61 $ 7.1 - 7.7 Particles / Mill.

6.85 - 7.32 particles / mill. (4H, aromatic protons)

Example III:

Preparation of 2,4-dichloro-6- (2 ', 3'-dichlorophenoxy) -

1,3,5-triazine

To a solution containing 18.4 g (0.1 mol) of cyanuric chloride in 150 ml of acetone was added, while cooling at a temperature of 0-5 C with magnetic stirring, a solution containing 16.3 g (0.1 Mole) of 2,3-dichlorophenol and 14.3 g (0.1 mole of quinaldine in 50 ml of acetone) The solution was added at such a rate as to maintain the reaction temperature at 0 ° -5 ° C. The resulting mixture was passed over was magnetically stirred for one hour, allowed to warm to room temperature, and the precipitated quinaldine hydrochloride was filtered off and washed with acetone The combined filtrates were then poured onto an iea and the resulting precipitated solid was collected by filtration washed with 100 ml of 10% aqueous NaOH and then with 100 ml of water After drying, the solid was crystallized from hexane to give a crude residue of 14.5 g. This material was evacuated by vacuum Purified to give 1.7 g (0.005 KoI) of 2,4-dichloro-6- (2 ', 3'-dichlorophenoxy) -1,3,5-triazine having a melting point of 154.5 ° - 156 ° C. The analysis of the product revealed the following:

Analysis: C ₉ H ₃ Cl ₄ H ₃ O

Calculated: C - 34.76, H - 0.97, N - 13.51. Determined: C - 34.30, H - 0.89, N - 13.80.

This compound is hereinafter referred to as Compound 37.

Example IV:

Other compounds were prepared in the same manner as in Example III. The structures and analytical data for compounds 38 to 45 used in the examples below to reduce plant moisture loss are given in Table B below.

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Table B. '

Representative heterocyclic, nitrogen-containing compounds

-c

verb , substituents X ₂ ^Y 7 ^Y 8 ulementaranalyse H K determined H K Melting point - 135 R ₁₃ calculated 1.40 19.52 C 1.25 19,66 ⁰ C - 95 0 Cl Cl C 1.46 15.20 37.04 1.49 15,80 - 120 38 2-IoO ₂   0 Cl Cl 37.65 0.97 13.51 39.01 0.76 13.92 132 - 208 39 2-Cl 0 Cl Cl 39.09 - 10.14 34.64 - 10.07 92 - 83 40 2,5-Cl ₂ 0 Cl Cl 3.4,76 2.08 14.46 27.41 2.26 14.57 118 41 Ci ₅ 0 Cl Cl 26,09 41.75 205 - 90 42 2-CH ₃ -4-Cl 41.34 6.43 9.25 6.19 9.12 82 - 122 43 4-Cn-C ₁₂ H ₂₅ - 0 Cl Cl 0.97 13.51 58.04 1.04 13,49 - 171 0-CO) - 0 Cl Cl 58.15 2.98 11.29 34.78 3.57 11.35 88 44 2,4-Cl ₂ 4-C ₆ H ₅ CH = CHCO- 0 Cl Cl 34.76 58.21 121 45 58.08 169

Example V:

Preparation of 2-chloro-4,6-bis (2 ·, 4 ^f -dichlorophenoxy) -

1,3,5-triazine

To a solution containing 9.2 g (0.05 mol) of cyanuric chloride in 100 ml of acetone was added 8.15 with cooling at a temperature of 0 ° -5 ° C with magnetic stirring. g (0.05 mol) of 2,4-dichlorophenol and 7.25 g (0.05 mol) of potassium carbonate. The ingredients were added so that the reaction temperature was maintained at 0 ° -5 ° C. The mixture was poured onto ice and the resulting solid precipitate collected by filtration, washed with 100 ml of 10% aqueous sodium hydroxide and then with water. After drying, the solid was recrystallized from hexane. The first crop of crystals was recrystallized twice from hexane to give 2.0 g (0.005 mol) of 2-chloro-4,6-bis (2 ·, 4'-dichlorophenoxy) -1,3,5-triazine having a melting point of 165 ° to 168 ° C. The elemental analysis of the product gave the following:

Analysis: C ₁₅ HgCl ₅ N ₃ O

Calculated: C - 41.18, H - 1.38, N - 9.60.

Determined: C - 41.41, H - 0.96, N - 9.86.

This compound is hereinafter referred to as compound 46 »

Example VI:

Preparation of 2,4-dichloro-6- (3 ', 5'-dichlorophenoxy) -

1,3,5-triazine

Into a stirred solution containing 5.24 g (0.032 mol) of 3,5-dichlorophenol in 15 ml of acetone was added 3.45 g (0.032 mol) of 2.6 under cooling at a temperature of 0 ° -5 ° C -lutidine, followed by a solution of 5.93 g (0.032 mol) of cyanuric chloride in 185 ml of acetone. The cyanuric chloride-acetone solution was added dropwise while maintaining the temperature at 0 ° -5 ° C. After completion of the addition of the material, stirring was continued at a temperature of about 0 ° C for one hour, then the mixture was warmed to ambient temperature, lutidine hydrochloride was removed by filtration, and the filtrate was treated with charcoal and filtered through celite. From the acetone solution, the solvent was removed under reduced pressure, and the residue was dissolved in toluene. This solution was washed with 0.5 N HaOH (twice) and water over MgSO 4. dried and ία vacuo evaporated to give 9.1 g of the crude solid product. Recrystallization from hexane and vacuum sublimation gave 1.0 g (0.003 mol) of pure 2,4-dichloro-6- (3, 5'-dichlorophenoxy) -1,3,5-triazine having a melting point of 109 ° -111 C Elemental analysis of the product gave the following: Analysis: C ₉ H ₃ Cl ₄ OM ₃

Calculated: C - 34.76, H - 0.97 ,. H - 13.51. Determined: C - 34.41, H - 0.90, H - 13.33.

This compound will be referred to as compound 47 below.

Example VII,

Preparation of 4,6-dichloro-2- (3'-dimethylaminophenoxy) -1,3,5-triazine and 6-chloro-2,4-bis (3'-dimethylaminophenoxy ) -1,3,5-triazine .

To a suspension containing 4.2 g (0.09 mol) of HaOH (50 % in oil) in 100 mL of dry tetrahydrofuran was added dropwise a solution containing 10.0 g (0.07 mol) of 3- (11 , N-dimethylamino) containing phenol in 200 ml of dry tetrahydrofuran, the temperature was 4 ⁰ C the mixture was warmed to room temperature, placed in an addition funnel and added dropwise to a solution containing 13.4 g (0.07 mol) of cyanuric chloride in 100 The mixture was stirred at 0 C over a period of three hours, evaporated and the residue extracted with hot CH ₂ Cl ₂ . The CH ₂ Cl ₂ solution was evaporated and the residue was purified by flash column chromatography on florosif ^ using 5 % EtOAc in hexane to give 1.70 g (0.004 mol), after recrystallization from uteroac-hexane, from 6- Chloro-2,4-bis (3'-dimethylaminophenoxy) -1, 3,5-triazine with a

Melting point of 134 ° - 136.5 ° C and 0.65 g (0.002 UoI) of 4,6-dichloro-2- (3'-dimethylaminophenoxy) -1,3,5-triazine as an oil. The elemental analysis of the two products revealed the following:

4,6-dichloro-2- (3'-dimethylaminophenoxy) -1,3.3-triazine

Analysis: C ₁₁ Ii ₁₀ Cl ₂ H ₄ O

Calculated: C - 46.34, H - 3.53, K - 19.65, Cl - 24.87. Determined: C - 48.69, H - 3.74, H - 17.17, Cl - 20.88. '

This connection will be referred to as a drain 48 hereinafter.

6-chloro-2,4-bis (3'-dimethylaminophenoxy) -1,3,5-triazine

Analysis: ^c - | g ^H ·

Calculated: C - 59, H ^ H - 5,22, H - 18,15, 0 - 8,28, Cl - 9,19. Determined: C - 58.52, H - 5.04, H - 17.85, 0 - 8.90, Cl - 9.46.

This compound will be referred to as compound 49 below.

Example VIII:

Preparation of 4,6-dichloro-2- (4'-bromo-3 ', 5'-dimethylphenol)

oxy) -1,3,5-triazine.

In a solution containing 9.2 g (0.05 mol) of cyanuric chloride in 80 ml of acetone was added 5.8 ml of 2,6-lutidine dissolved in 10 ml of acetone at a temperature of -60 ° C. Then, a solution of 10.0 g (0.05 mol) of 4-bromo-3,5-dimethylphenol in 30 ml of acetone was added while maintaining the temperature of -60 ° C. The mixture was stirred at -60 ° C for one hour and at room temperature for 30 minutes, then it was filtered and the precipitate washed with acetone. The filtrate was poured on ice and the resulting precipitate was collected by suction filtration. The crude product was washed with water and crystallized from hot hexane to give 1.49 g (0.004 mol) of 4,6-dichloro-2- (4'-bromo-3 ', 5'-dimethylphenoxy) -1,3,5- triazine as pink-orange crystals with a melting point of 149-151C. The clementar analysis of the product revealed the following:

Analysis: C ^

Calculate: C - 37.86, H - 2.31, N - 12.04. Determined: C - 38.63, H-2.47, H-11.55.

The tile connection will be referred to as compound 50 below.

Example IX:

Other compounds were prepared in the same manner as in Example VIII. The structures and analytical data for compounds 51 to 61 used in the following examples for the reduction of moisture loss of plants are given in Table C below. To prepare Compound 61, instead of 2,6-lutidine, triisopropanolamine was used as the acid acceptor.

Table C Representative heterocyclic. nitrogenous compounds

Verb. Substituents

R ₁₄ -χ

Elemental analysis

calculated

determined

Melting point

on

53 Cl / Q

44.47 1.87 15.56 '44.75 2.02. 16.06 HO - 141

56.63 2.85 13.21 56.01 2.68 13.37 189

49.32 3.18 8.85 47.92 3.05 12.68 121-123

Table C (continued)

Representative heterocyclic, nitrogen-containing compounds

Verb. Substituents

¹⁴ ~ -it.

Cl member analysis

calculated

Srtnittelt

Melting point

oV o)

53.45 2.41 - 53.60 2.82 - 92.5 - 93.5

52,72,3,7,14,19 51,55 4,18 14,56 '133-139

47,82 1,85 12,87 48,82 1,95 12,45 126 - 127

Table C (continued)

Representative heterocyclic, nitrogen-containing compounds

Verb. Substituents

^R H ~~ ^X 3 '

^ Cl elemental analysis

calculated

determined

H K

Melting point, ⁰ C

53.45 2.41 H.38 52.65 2.61 13.97 154 · - 155

38.83 1.83 11.32 39.18 1.95 11.45 172-174

30.41 0.85 11.82 ¹³ C KMR (CDCl ₃ ) J 116 366, 126

123 788, 128 881, 129 179, 133 513, 147 137, 170 460, 173 331 'Particles / Wed !!. '

Table C (continued).

Representative heterocyclic, nitrogen-containing compounds

Verb. Substituents

Elemental analysis

calculated

determined

HN

Melting point

60 CH-

CH,

50.72 3.90 14.79 51.34 4.09 14.90 147 - 149

52.20 2.82 13.04 52.28 2.96 13.08 176 - 177.5

Example X:

Preparation of 4,6-dichloro-2- (2'-phenylphenoxy) -1,3,5-

triazine

Into a magnetically stirred solution containing 10.83 g (0.06 mol) of cyanuric chloride in 100 ml of acetone was added a solution containing 11.24 g (0.06 mol) of triisopropanolamine in 100 ml of acetone, the. Temperature was -70 ° C. Then, at a temperature of -70 ° C, a solution of 10.0 g (0.06 mole) of 2-phenylphenyl in 100 ml of acetone was added dropwise. This mixture was stirred at room temperature for one hour, filtered and the filtrate poured onto ice-water. After removal of the acetone solvent by evaporation, the resulting mixture was partitioned between water and CH ₂ Cl ₂ , the organic layer was evaporated using anhydrous Na ₂ SO ₄ . dried and evaporated. The remaining product was purified by flash column chromatography using silica gel and eluted with 5 % ethyl acetate in hexane to obtain 6.0 g (0.02 mole) of 4,6-dichloro-2- (2'-phenylphenoxy) -1 To give 3,5-triazine as an oil. The elemental analysis of the product gave the following:

Analysis: C ₁₅ H ₉ Cl ₂ N ₃ O

Calculated: C - 56.63, H - 2.85, N - 13.21, Cl - 22.29.

Determined: C - 55.65, H - 2.99, K - 13.46, Cl - 24.18.

This compound will be referred to as Compound 62 below.

Example XI:

Preparation of 2,4-dichloro-6- (2'-chlorophenylamino) Ti, 3,5- triazine

In the same manner as in Example VIII, 4.63 g (0.04 mol) of 2-chloroaniline and 6.69 g (0.04 mol) of cyanuric chloride in the presence of 3.89 g (0.04 mol) of 2,6 -Lutidine reacted, however, the cooling bath was removed at the end of the feed period and the stirred mixture was allowed to warm to quench temperature. After filtering out the lutidine hydrochloride, the filtrate was freed from the acetone solvent under reduced pressure, and the resulting gum was crystallized from a mixture of hexane and benzene. The first yield of the product was 1.1 g (0.004 mol) of 2,4-dichloro-6- (2-chlorophenylamino) -1,3,5-triazine with a melting point of 153 ° -156 ° C. The nuclear magnetic resonance of the product gave the following: WMR: 7.0-8.35 particles / mill. (complex multiple,

aromatic and MH).

This compound will be referred to as compound 63 below.

Example XII: "

Preparation of 2,4-dichloro-6- (4'-chlorophenylamino) -1,3,5- triazine

In the same manner as in Example XI, 6.94 g (0.05 mol) of 4-chloroaniline, 10.04 g (0.05 mol) of cyanuric chloride and 5.83 g (0.05 mol) of 2,6-lutidine in Acetone solution reacts. After completion of the feed, the reaction mixture was stirred for one hour at a temperature of 0 ° C and then for a period of about 16 hours at room temperature. The preparation gave after washing in water and drying, 14.0 g (0.05 mol) of 2,4-dichloro-6- (4 ^l -chlorophenylamino) -1,3,5-triazine with a melting point of 181 ° - 184 ° C. The nuclear magnetic resonance analysis of the product showed the following: ¹³ C-HMR (dg-acetone) 171.38, 165.29, 136.74, 130.56, 129.72, 123.79 particles / mill.

This compound is described below as. Designated connection 64

 Example XIII:

Preparation of 2,4-dichloro-6- (5 ', 6', 7 ', 8'-tetrahydronaphyl -1'-amino) -1,3,5-triazine

Into a stirred solution containing cyanuric chloride (5.0 g, 0.03 mol) in A2 ezone (120 ml) was added dropwise at a temperature of 0 ° C a solution containing 2,6-lutidine (3.15 ml , 0.03) and 1-amino-5,6,7,8-tetrahydroaaphthalene

(3.97 g, 0.03 mol) in acetone (200 ml). After two hours at 0 ° C, the reaction mixture was warmed to room temperature and stirred for a period of one hour. The reaction mixture was filtered, and the filtrate was filtered through silica gel and washed with acetone to give 2,4-dichloro-6- (5 ', 6', 7 ', 8-tetrahydronaphthyl-τΐ'-amino) -1,3 To give 5-triazine as a solid (7.0 g, 0.02 mol) having a melting point of 158-162 ° C. The elemental analysis of the product gave the following:

Analysis: C ₁₃ H ₁₂ Cl ₂ H ₄

Calculated: C - 52.89, H - 4.10, N - 18.98. Determined: C - 53.03, H - 4.06, N - 18.89.

This compound will be referred to as Compound 65 below.

Example XIV:

Preparation of 4,6-dichloro-2- (4'-nitrophenylamino) -1,3,5-triazine

Into a solution containing 20 g (0.11 mol) of cyanuric chloride in 300 ml of acetone was added a solution containing 15.0 g (0.11 mol) of p-nitroaniline in 200 ml of acetone, and a solution containing 12.6 ml (0.11 mol) of 2,6-Lutidln contained in 100 ml of acetone. The resulting mixture was stirred at room temperature under a nitrogen atmosphere for about 16 hours. Then, the mixture was filtered, the filtrate was poured onto ice-water, and the resulting precipitate was collected to give 5.6 g of a crude product. The crude product was recrystallized from acetone-toluene to give 3.72 g (0.01 mol) of 4,6-dichloro-2- (4'-nitrophenylamino) -1,3,5-triazine as a yellow solid having a melting point of 240 ° C (decomposition). The blementar analysis of the product gave the following:

Analysis: C ₉ H ₅ M ₅ O ₂ Cl ₂

Calculated: C - 37.79, H - 1.76, N - 24.48, 0 - 11.19, Cl 24.79 ·

Determined: C - 38.04, H - 2.01, H - 24.20, 0 - 11.14, Cl 23.74.

This connection will be referred to as connection 66 below.

Example XV:

Preparation of 4,6-dibromo-2- (4'-nitrophenylamino) -1,3,5- triazine

To a solution containing 600 mg (0.002 mol) of 4,6-dichloro-2- (4'-nitrophenylamino) -1,3,5-triazine, as prepared in Example XIV, was dissolved in 300 ml of CH ₂ Cl ₂ , was bubbled with HBr gas over a period of 4 hours at room temperature. The resulting mixture was stored in a refrigerator for about 48 hours, and an oil, which thereby settled from CHgClg, was collected by decantation. Daa oil was rinsed with CH ₂ Cl ₂ (3 × 20 mL) and then recrystallized from toluene to give 600 mg (0.002 mole) of 4,6-dibromo-2- (4'-nitrophenylamino) -1,3,5- triazine as a yellow solid. The elemental analysis of the product gave the following:

C ₉ H ₅ H ₅ O ₂ Br ₂

Analysis:

Calculated: C - 28.81, H - 1.34, H - 18.67. Determined: C - 29.85, H - 2.75, N - 18.85.

This compound will be referred to as Compound 67 below.

Example XVI:

Preparation of 4,6-dibromo-2- (4'-chlorophenylamino) -1,3,5-

triazine

In the same manner as in Example XV, 4,6-dichloro-2- (4'-chlorophenylamino) -1,3,5-triazine was reacted with hydrogen bromide to give 4,6-dibromo-2- (4'-chlorophenylamino) - 1,3,5-triazine with a melting point of 197.5 ° - 200 ° C to produce. The elemental analysis of the product gave the following:

Analysis: CH ₅ N-ClBr ₂

Calculated: C - 29.66, H - 1.39, W - 15.38, Cl - 9.73, Br -

43.85

 Finds C-29.49, H-1.48, N-15.19, Cl-9.36, Br-43.40.

This connection will be referred to as compound 68 below.

Example XVII:

Preparation of 2- (4'-chlorophenylamino) -4 »6-difluoro-1,3,5-

triazine _:

In a stirred solution containing 16.21 g (0.12 mol) of cyanuric fluoride in 120 ml of toluene, a solution of 12.75 g (0.10 mol) was added while cooling to a temperature of -10 ° to 0 ° C. 4-chloroaniline in 120 ml toluene over a period of two hours. The mixture was then stirred at room temperature for 15 minutes and at 50 ° C for thirty minutes. After filtering, the filtrate was reduced to half volume by rotary vacuum evaporation of the solvent. The crude crystalline product (12.6 g) was separated from the concentrated solution and recrystallized from toluene after filtering and drying, yielding 6.3 g (0.03 mol) of 2- (4 ^l -chlorophenylamino) -4, 6-difluoro-1,3,5-triazine in the form of white crystals having a melting point of

tis 13

144 ° - 147 ° C. The nuclear magnetic resonance analysis of the product gave the following: ' ^U C-NMR (dg-acetone) | 177.09 (m), 168.21 (m), 130.75, 129.75, 124.12 particles / mill.

This compound will be referred to as compound 69 below.

Example XVIII:

Preparation of 4-chloro-6-; iodo-2- (2 ^l, 4'-dichlorophenoxy) -

1.3,5-triazine

To a suspension containing 6.0 g (0.02 mol) of 4,6-dichloro-2- (2 ·, 4'-dichlorophenoxy) -1,3,5-triazine in 60 ml of acetone was added a solution containing 5.8 g (0.04 mol) of NaI in 60 ml of acetone. The resulting mixture was stirred and heated to a temperature of 90 ° C over a six hour period in a sealed bottle. Then, the mixture was filtered, the filtrate evaporated to give 9.2 g of a solid and to this solid was added 40 ml of methylene chloride, and then the suspension was filtered. The filtrate was evaporated and the residue was sublimed in vacuo at 90 ° C for 10 hours. Then, the temperature was raised to 160 ° -190 ° C, and the cold finger collected 2.0 g of an off-white solid. This solid was recrystallized from CH, CN-water to give 1.0 g (0.002 mol) of 4-chloro-6-; iodo-2- (2 ', 4'-dichlorophenoxy) -1,3,5-triazine a white solid with a melting point of 155-158C.

The elemental analysis of the product gave the following; Analysis: C ₉ H ₃ Cl ₃ IN ₃ O

Calculated: C - 26.84, H - 0.75, W - 10.44, I - 31.54. determined; C - 26.87, H - 0.77, N - 10.27, I - 30.61.

This connection will be referred to as connection 70 below.

Example XIX:

Preparation of 4,6-dibromo-2- (2 ', 4'-dichlorophenoxy) -

1,3,5-triazine

A portion of 2,4-dichloro-6- (2 ', 4'-dichlorophenoxy) -1,3,5-triazine, prepared in the same manner as in Example III, of 4.0 g (0.01 mol ) was dissolved in 200 ml toluene. For a period of 5 hours, HBr gas was continuously bubbled through this mixture in the reflux. The reaction mixture was cooled to room temperature and nitrogen gas was bubbled through the mixture to remove any excess HBr that may be present. The reaction mixture was then evaporated to dryness and the residue was recrystallized from CHgClg / hexane to give 1.97 g (0.005 mol) of 4,6-dibromo-2-one.

(2 ·, 4'-dichlorophenoxy) -1,3,5-triazine in the form of silver-gray crystals with a melting point of 1.74 ° -176 ° C. The elemental analysis of the product gave the following: Analysis: C ₉ H ₃ Br ₂ Cl ₂ W ₃ O

Calculated: C - 27.00, H - 0.75, K - 10.50, Cl - 17.50. Determined: C - 27.41, H - 0.65, W - 10.01, Cl - 16.70.

This connection is hereinafter referred to as connection 71.

Example XX:

Preparation of 2- (4'-chlorophenoxy) -4,6-difluoro-1,3,5-

triazine

Into a stirred solution containing 3.91 g (0.03 mol) of cyanuric fluoride in 150 ml of acetone was added dropwise a mixture containing 3.72 g (0.03 mol) of 4-chlorophenol and 3.10 g (0 , 03 mol of 2,6-lutidine, the temperature was 0 ° C. After the reaction mixture had been stirred for about 16 hours, it was poured onto ice, whereby an oil settled down.The oil was taken up in ether, first with 0, 5N NaOH and then washed with water and then dried Evaporation gave a white pest that was recrystallized from hexane and vacuum sublimed to give 0.47 g (0.002 mol) of 2- (4'-chlorophenoxy) -4,6-difluoro -1, 3,5-triazine with a melting point of 81 ° -82.5 ° C. The elemental analysis of the product showed the following: Analysis: C ₉ H ₉ ClPN ₃ O ₄

Calculated: C - 44.74, H - 1.67, K - 17.39. Calculated: C - 44.80, H - 1.72, N - 17.23.

This connection will be referred to as connection 72 below.

Example XXI:

Preparation of 2-Pluoro-4,6-bis- (4'-chlorophenoxy) -1,3,5-

triazine

Into a mixture containing 3.72 g (0.03 mol) of 4-chlorophenol and 3.10 g (0.03 mol) of 2,6-lutldin in 15 ml of acetone was heated with magnetic stirring and cooling to a temperature of 0 ° to 5 ° C, a solution containing 3.91 g (0.03 mol) of cyanuric fluoride in 185 ml of acetone. After stirring at 0 ° to 5 ° C for one hour, the mixture was stirred for another approximately 70 hours at ambient temperature. The mixture was then stirred and heated under reflux for about 28 hours, cooled to room temperature and poured on ice to give a solid. The solid was washed in water, taken up in toluene, and the resulting solution was washed successively with 0.5 N NaOH and water, then dried over MgSO 4, and evaporated under reduced pressure. The residual plating substance was recrystallized from hexane to give 1.20 g (0.003 mol) of a first crop of 2-pluoro-4,6-bis (4'-chlorophenoxy) -1,3,5-triazine having a melting point of 149 ° - 150 C. The elemental analysis of the product showed the following:

Analysis:

Calculated: C - 51.15, H - 2.39, N - 11.93, P - 5.39. Determined: C - 51.20, H - 2.21, N - 11.89, P - 5.16.

This compound will be referred to as compound 73 below.

Example XXII:

Preparation of 2,4-dichloro-6- (4'-sec-butyloxyphenoxy) -

1,3,5-triazine

Part A: Preparation of 4- (sec-butyloxy) phenol

In a 500 ml Eundboden bottle under a nitrogen atmosphere, NaOH (2.91 g, 0.07 mol) and 125 ml of water / dioxane (degassed) in the ratio of 1: 1 was added. After all the HaOH was dissolved, hydroquinone (4.0 g, 0.04 mol) was added and the resulting solution immediately turned dark brown. At this time, 2-iodobutane (4.15 ml, 0.04 mol) dissolved in 5 ml of dioxane was added,

and the mixture was stirred at room temperature for 72 hours and then acidified to a pH of about 2 with a 10% aqueous solution of HCl solution. The aqueous solution was extracted with EtOAc (2 x 150 ml) and the combined extracts were washed with water and saturated NaCl, dried (MgSO 4) and concentrated in vacuo to give

to give a mixture of the crude product. This mixture was purified by flash chromatography to give a small amount of a dialkylated product, 2.31 g (0.01 mol) of 4- (sec-butyloxy) phenol and the starting hydroquinone in the order of elution. The nuclear magnetic resonance analysis of the product showed the following: NMR (CDCl ₃ ) (i 0.95 (t, 3H, J = 7 Hz), 1.29 (d, 3H, J = 6 Hz), 1.29-1.40 (m, 2H), 4.12 (sextet, 1H, J = 6Hz), 6.35 (brs, 1H), 6.72 (s, 4H) particles / Mill.

Part B: Preparation of 2,4-dichloro-6- (4'-sec-butyloxyphenoxy ) -1,3,5-triazine

Into a 100 ml round-bottomed three-necked flask equipped with thermometer, addition funnel and nitrogen inlet was added 2.22 g (0.01 mol) of cyanuric chloride dissolved in 20 ml of acetone. After cooling to a temperature of 0-5 C, 4- (sec-butyloxy) -phenol (2.0 g, 0.01 mol), prepared in part A, and 2,6-lutidine (1, 40 ml, 0.01 mol) dissolved in 20 ml of acetone was slowly added dropwise via the addition funnel. The reaction temperature was maintained between 0 ° and 5 ° C during the addition. The reaction mixture was then stirred at room temperature over a period of 16 hours. After this time, the reaction mixture was filtered through a celite pad and the pad rinsed with acetone. Ice-water was added and the oil which settled out was extracted with EtOAc. The EtOAc layers were washed with water, dried (MgSO 4), concentrated by urine to give a semi-solid, brown fabric. The crude product was purified by flash chromatography on silica (eluant 10 % EtOAc / hexane) to give 2.43 g (0.008 mol) of 2,4-dichloro-6- (4'-sec-butyloxyphenoxy) -1,3,5-triazine as pale yellow crystals with a melting point of 52.0 ° to 55.0 ° C. The elemental analysis of the product gave the following:

Analysis: C ₁₃ H ₁₃ Cl ₂ N ₃ O ₂

Calculated: C - 49.70, H - 4.17, N - 13.37. Determined: C - 50.26, H - 4.51, N - 13.10.

This connection will be referred to as connection 74 below.

Example XXIII :

Other compounds were prepared in the same manner as in Example XXII. The structures and analytical data for Compounds 75 to 83 used in the examples below for reducing plant moisture loss are given in Table D below.

Table D '

Representative heterocyclic, nitrogen-containing compounds

Verb. substituents Elemental analysis C 49,70 H N determined H 13.32 Melting point IIaE ^R 15 calculated 53.94 4.17 13.37 C 4.27 11.87 ⁰ C 52.96 5.38 11,80 49,66 5.33 12.02 75 ¹ Λ. Q 55.19 4 * 44 12.35 53.96 · 4.58 11.22 51.0 - 52.5 76 62.28 3.18 12.07 53,30 3.42 10.28 51.5 - 53.5 77 3.56 9.90 • 55 .98 3.74 95.0 - 96.0 78 4- (O) -CH ₂ - 60.82 130.5 - 132.5 79 4- / ÖWÖV 174.0 - 176.0 -CH ₂ -

Table D (continued)

Representative heterocyclic, nitrogen-containing compounds

R ₁₅ O

Cl

Cl

Verb. substituents

Elemental analysis

calculated

determined

melting point

C H N C H K 86 , 0 - 89 , 0 44.14 2.59 15.44 44.13 2.67 15.68 46 , 0 - 48 , 0 49,70 4.17 13.37 49.92 4.49 13.42 oil 52.96 4.44 12.35 52.51 4.41 12.69 oil 55.19 3.18 12.06 59.64 3.89 10.28

3-CH,

Example XXIV:

Preparation of 4-chloro-6-methyl-2- (2 ', 4'-dichlorophenoxy) -1,3,5-triazine ; __ ^

To a solution containing 5.0 g (0.02 mol) of 2,4-dichloro-6- (2 ·, 4'-dichlorophenoxy) -1,3,5-triazine, which was prepared in the same manner as in Example III 5.9 milliliters of a 2.7 M solution of methylmagnesium bromide in ether was added dropwise at a temperature of 0 C in 400 ml of dry tetrahydrofuran. The resulting mixture was stirred at room temperature under a nitrogen atmosphere for about 18 hours. The mixture was concentrated and the residue was purified by flash column chromatography on silica gel using 10 % EtOAc in hexane to give 2.00 g (0.007 mol) of 4-chloro-6-methyl-2- (2 ·, 4'-dichlorophenoxy ) -1,3,5-triazine with a melting point of 107 ° -108 ° C. The blementar analysis of the product gave the following:

Analysis: C ₁₀ HgCl ₃ N ₃ O

Calculated: C - 41.34, H - 2.08, M - 14.46, Cl - 36.61. Determined: C - 41.35, H - 2.39, N - 14.46, Cl - 36.85.

This connection will be referred to as compound 84 below.

Example XXV:

Preparation of 4-Brotno-6-methyl-2- (2 ·, 4'-dichlorophenoxy) -1,3,5-triazine '

In a solution containing 2.0 g (0.007 mol) of 4-chloro-6-methyl-2- (2 ^!, 4 * -dichlorophenoxy) -1,3,5-triazine, prepared as in Example XXIV, in 300 ml of CH ₂ Cl, dry HBr gas was bubbled over a period of 3 hours. The mixture was allowed to stand at room temperature for about 18 hours. Then the suspension was filtered and the pesticides were separated between NaHCO ₃ solution and CH ₂ Cl ₂ . The organic layer was over anhydrous Ha ₃ SO. dried, and the solvent was evaporated to give 0.7 g (0.002 mol) of 4-bromo-6-methyl-2- (2 ', 4 ^l -dichlorophenoxy) -1,3,5-triazine having a melting point of 123 ° - 127 ° C received. Slementar analysis of the product gave the following:

Analysis: C ₁₀ g ₂₃

Calculated: C - 35.85, H - 1.81, N - 12.54, Cl - 21.17, Br -

23.85

 C - 36,22, H - 2,15, N - Ϊ2,46, Cl - 22,00, Br 21,20.

This compound will be referred to as compound 85 below.

Example XXVI:

Preparation of 4-chloro-6-methyl-2- (1-naphthoxy) -1,3,5- triazine

In a solution containing 5.0 g (0.02 mol) of 4,6-dichloro-2- (1-naphthoxy) -1,3,5-triazine prepared in Example IX in 300 ml of tetrahydrofuran 7.0 ml of 2,7M-methylmagnesium bromide in 200 ml of tetrahydrofuran was added dropwise at a temperature of 4 ° C. The resulting mixture was stirred at room temperature for about 18 hours and then evaporated. The residue was purified by flash column chromatography on silica gel using 7 % ethyl acetate in hexane to give 2.0 g (0.007 mol) of 4-chloro-6-methyl-2- (1-naphthoxy) -1,3,5-triazine a melting point of 80 ° - 83 ° C (recrystallized from CHgCI ₂ -hexane). The elemental analysis of the product gave the following:

C ₁₄ H ₁₀ CBI ₃ O

Analysis:

Calculated: C - 61.89, H - 3.71, N - 15.4ß, Cl - 13.05. Determined: C - 61.86, H - 3.72, N - 15.46, Cl - 13.07.

This compound will be referred to as Compound 86 below.

Example XXVII:

Preparation of 2-chloro-4-methoxy-6- (2 ^l , 4'-dichlorophene)

oxy) -1.3.5-triazine

Into a stirred solution containing 10.0 g (0.03 mol) of 2,4-dichloro-6- (2 ', 4'-dichlorophenoxy) -1,3,5-triazine in 200 ml of acetone were added a temperature of 0 ° - 5 ° C 3.49 g (0.03 mol) of 2,6-lutidine. To this mixture was added dropwise 1.03 g (0.03 mol) of methanol while warming to room temperature. The mixture was heated to 50 ° C and held at this temperature for about 6 hours, then it was cooled to room temperature and stirred for about 60 hours. The lutidine hydrochloride was filtered off, the solvent evaporated and the residue dissolved in ether and dried over MgSO 4. dried. The solution was subjected to flash chromatography on a silica column, eluting with CH ₂ Clg / hexane (9: 1). Evaporation of the solvent gave 3.14 g of a crystalline product which was recrystallized from hexane and 1.86 g (0.006 mol) of 2-chloro-4-methoxy-6- (2 ', 4'-dichlorophenoxy) -1,3 5-triazine with a melting point of 87 ° -89 ° C. The elemental analysis of the product gave the following:

Analysis: C ₁₀ HgCl ₃ M ₃ O ₂

Calculated: C - 38.67, H - 1.97, W - 13.71. Determined: C - 38.94, H - 2.00, N- 14,09.

This compound was hereinafter referred to as compound 87.

Example XXVIII:

Preparation of 4,6-bis- (2 ·, 2 ', 2'-trifluoroethoxy) -2-phenyl-

1,3.5-triazine

Into a stirred solution containing 1.06 g (0.02 mol) of KaH (50 % in oil) in 30 ml of dry tetrahydrofuran was added dropwise a solution containing 1.72 ml (0.01 mol) of 2.2 , 2-trifluoroethanol in 10 ml of dry tetrahydrofuran, the temperature was 4 C. This mixture was stirred at room temperature under a nitrogen atmosphere for 20 minutes. The mixture was then passed to an addition funnel under a nitrogen atmosphere and dropwise to a solution of 5.0 g (0.02 mol) of 4,6-dichloro-2-phenyl-1,3,3,5-triazine in 60 ml of dry tetrahydrofuran at room temperature stirred, stirred for about 18 hours and then evaporated to dryness. The residue was purified by Entspannungskolonnenchromatografie on silica gel using 2% EtOAc in hexane to give 0.9 g of a tubular product, the ₂ C1 ₂ -hexane was recrystallized from CH and 0.48 g (0.001 mol) of 4,6-bis- (2 ·, 2 ·, 2'-trifluoroethoxy) -2-phenyl-1,3,5-triazine in the form of white plates with a melting point of 92 ° - 93 ° C. The elemental analysis of the product gave the following:

Analysis: C ₁₃ H ₉ N ₃ O ₂ F ₆

Calculated: C - 44.20, H - 2.57, N - 11.89, F - 32.27. Determined: C - 44.51, H - 2.57, N - 12.03, F - 31.56.

This compound will be referred to as compound 88 below.

Example XXIX:

Preparation of 4-chloro-6- (2 ', 2', 2'-trifluoroethoxy) -2-

phenyl-1,3,5-triazine

The fractions from the column chromatography of Example XXVIII were examined and a group identified, the second component being 4-chloro-6- (2 ·, 2 ·, 2 ·, trifluoroethoxy) -2-phenyl-1,3,5-triazine contained. These were combined and purified by preparative liquid chromatography (silica gel) using 10 % ethyl acetate in hexane as the eluent to give 320 mg (0.001 mol) of 4-chloro-6- (2 ', 2', 2'-trifluoroethoxy) -2 -phenyl-1,3,5-triazine as an oil. The elemental analysis of the product gave the following:

Analysis: C Calculated: C - 45.61, H - 2.44, 19.68.

- 14.51, Cl - 12.24,

Determined: C - 45.43, H - 2.41, N - 14.45, Cl - 12.28, P -. 18.02.

This compound will be referred to as compound 89 below.

Example XXX:

Preparation of 2-chloro-4- (2 ·, 4'-dichlorophenoxy) -6- (di- ethoxyphosphin-1-i3,5-triazine

Part A. Preparation of 2,4-dichloro-6- (diethoxyphosphinyl) -1,3,5-triazine

Into a stirred solution containing 36.9 g (0.02 mol) of cyanuric chloride in 150 ml of toluene was added 33.2 g (0.02 mol) of triethyl phosphite in small portions. The exothermic reaction was controlled by cooling in an ice bath until completion of the reaction. The reaction mixture was stirred for a period of about 18 hours at a temperature of 60 ° - 90 ° C and heated. Toluene was removed under reduced pressure and the residue was extracted with hexane. After filtering through Celite, the crude product of 2,4-dichloro-6- (diethoxyphosphinyl) -1,3,5-triazine had the following nuclear magnetic resonance spectrum (CDCl ₃ ): 1) 1.15 - 1.65 particles / mill. (3H, t, CH _3), 4.16 to 4.75 (2H, pentet, _CH2). This product was used without cleaning in part B.

Part B. Preparation of 2-chloro-4-i2 ·, 4'-dichlorophenoxy ) -6-diethoxyphosphinyl) -1,3,5-triazine

A portion of 10 g (0.035 mol) of 2,4-dichloro-6- (diethoxyphosphinyl) -1,3,5-triazine prepared in Part A is dissolved in 50 ml of acetone and the resulting solution over a period of 15 minutes, a stirred mixture of 102 g E3.S and added 54 ml of water. To this stirred suspension was added a solution containing 5.7 g (0.035 mol) of 2,4-dichlorophenol in 18 ml of 8% aqueous sodium hydroxide. This mixture was stirred at 0 ° to 5 ° C for one hour and then for an additional hour at room temperature. The aqueous layer was decanted and the organic residue was taken up in ether, washed with water, dried, filtered and the solvent evaporated to give 9.1 g (0.02 mol) of 2-chloro-4- (2 x 10) '-dichlorophenoxyj-e-idiethoxyphosphinyl) -1,3,5-triazine as an oily residue product. The elemental analysis of the product gave the following:

C ₁₃ H ₁₃ Cl ₃ N ₃ O ₄ P

Analysis: _1313334

Calculated: C - 37.84, H - 3.18, P - 7.51, Cl - 25.78. Determined: C - 38.93, H - 3.43, P - 7.37, Cl - 25.32.

This compound will be referred to as compound 90 below.

Example XXXI:

Preparation of 2,4-dichloro-6- (2'-carbomethoxyphenylsulfo)

nylamino) -1.3.5-triazine

A mixture of 5.7 g (0.03 mol) of cyanuric chloride and 7.11 g (0.03 mol) of the sodium salt of 2-carbomethoxybenzenesulfonamide in 150 ml of toluene was stirred at room temperature over a period of 20 minutes. The mixture was then heated to 80 ° C for 3 hours, filtered hot, the filtrate diluted with hexane and cooled. A white solid was precipitated and taken up by suction and dried. This gave 3.0 g (0.008 mol) of 2,4-dichloro-6- (2'-carbomethoxyphenylsulfonylamino) -1,3,5-triazine having a melting point of 212 ° -215 ° C. The elemental analysis of the product gave the following:

Analysis: C ₁₁ H ₄₄

Calculated: C - 36.38, H - 2.22, N - 15.42. Calculated: C - 38.36, H - 1.63, N - 15.42.

This compound will be referred to as Compound 91 below

Example XXXII:

Preparation of 2- (2 ', 4'-dichloro-alpha-methylbenzyloxy) -

4,6-dichloro-1,3,5-triazine

Into a solution containing 7.4 g (0.04 mol) of cyanuric chloride in 50 ml of acetone under a nitrogen atmosphere was added dropwise, when cooled to 0 ° C, a mixture of 7.6 g (0.04 mol) of 2,4- Dichloro-alpha-methylbenzyl alcohol and 4.3 g (0.04 mol) of 2,6-lutidine in 25 ml of acetone added. The resulting dark red reaction mixture was stirred at 0 ° C for 30 minutes, during which time a white precipitate formed. For two days stirring was continued at room temperature. Then, the precipitate between filters was separated, and the filtrate was concentrated under reduced pressure. The unreacted cyanuric chloride was distilled out using a Kugelrohr apparatus (0.25 mm Hg, 50 ° -70 ° C). The dark residue on silica gel was then chromatographed using a 9: 1 hexane-EtOAc eluent. This gave 5.0 g of an orange-yellow oil which was distilled using a Kugelrohr apparatus and a diffusion pump (10 ~ 4 mm Hg, 120 ° C) to give 2.0 g of a colorless solid. Recrystallization from hexane gave 1.4 g (0.004 mol) of 2- (2 ·, 4'-dichloro-alpha-methylbenzyloxy) -4,6-dichloro-7i, 3,5-triazine as colorless needles with a melting point of 97, 5 ° - 99.5 ° C. The elemental analysis of the product gave the following:

C ₁₁ H ₇ Cl ₄ N ₃ O

Analysis:

Calculated: C - 38.97, H - 2.08, N - 12.40. Calculated: C - 39.02, H - 1.92, N - 12.58.

This connection will be referred to as connection 92 below.

Example XXXIII;

Other compounds are prepared in the same way as in Example XXXII. The structure and analytical data for the compounds '93 to 95 used in the following Examples for the reduction of moisture loss of plants are given in Table E below.

Table E-. Representative heterocyclic, nitrogen-containing compounds ^

Verb. Substituents elementary analysis

4 ·

calculated

determined

Smelter ¹ C

point, o

H Ν

93 2,4-Cl ₂ -CH ₂ O- 36,96 1,55 12,93 37,10 1,61 12,77 99,0 bis

103.5

94 2,4-Cl ₂ -CH-O- 37.75 1.15 16.01 38.06 1.34 16.19 96.0 l

CN 98.5

95 H -CH-O- 40,77 1,87 12,97 40,90 2, "'-"" ^r '" ⁿ -

Example XXXIV:

Preparation of 2,4-dichlorobenzaldehyde- O- (4,6 " 1,3,5-triazin-2-yl) oxime

, 04 12,76 68,0 to 70,0

• dichloro-

Part A. Preparation of 2,4-dichlorobenzaldehvdoxime

Into a solution containing 8.8 g (0.13 mol) of hydroxylamine hydrochloride in 20 mL of water and cooled to a temperature of 0 C was added 10.6 g (0.13 mol) of sodium bicarbonate and a solution of 14.7 g (0.08 mol) of 2,4-dichlorobenzaldehyde in 50 ml of ethanol. At room temperature and under nitrogen pressure stirring was continued for 3.5 hours. Then. The reaction mixture was diluted with 150 ml of water and extracted with CH ₂ Cl ₂ (3 × 100 ml). The combined organizational

Nisohen layers were over MgSO. and concentrated under reduced pressure to give 15.7 g of a colorless solid. Chromatography on silica gel using dichloromethane as the eluant afforded 14.2 g (0.07 mol) of 2,4-dichlorobenzaldehyde oxime as a colorless solid. The magnetic Kernresnnanzspektrum of this material was as follows: NMR _(CDCl3) J 7.21 (1H, dd, J = 9.2 Hz), 7.40 (1H, d, J = 2 Hz), 7.75 (1H , d, J = 9 Hz), 8.09 (1H, s), 8.49 (1H, s) particles / mill.

Part B. Preparation of 2,4-dichlorobenzaldehyde- O- (4,6-di- chloro-1,3,5-triazin-2-yl) oxime .

2,4-Dichlorobenzaldehyde oxime prepared in Part A was reacted with cyanuric chloride using the same procedure as Example XXXII above. The reaction mixture was filtered to remove the precipitate, and the filtrate was poured onto ice to form a yellow, solid. The solid was separated and recrystallized from acetone-water to give 2.1 g (0.006 mol) of 2,4-dichlorobenzaldehyde-O- (4,6-dichloro-1,3,5-triazin-2-yl) oxime Form pale yellow needles with a melting point of 124 ° - 124.5 ° C. The elemental analysis of the product gave the following:

Analysis: C ₁₀ H ₄ Cl ₄ N ₄ O

Calculated: C - 35.54, H - 1.19, N - 16.58. Determined: C - 35.72, H - 1.35, N - I674.

This connection is referred to below as compound 96.

Example XXXV:

Preparation of acetophenone 0- (4,6-dichloro-1,3,5-triazine-2-one

yl) oxime .

Acetophenone oxime and cyanuric chloride were reacted according to the procedure of Example XXXIV to produce acetophenone-O- (4,6-dichloro-1,3,5-triazin-2-yl) oxime having a melting point of 123 ° to 127 ° C. The elemental analysis of the product gave the following:

Analysis: C ₁₁ N ₄ O ₂ HgCl

Calculated: C - 46.67, H - 2.85, N - 19.79.

Calculated: C - 47.10, H - 2.80, N - 19.77.

This compound is hereinafter referred to as compound 97.

Example XXXVI:

Preparation of 2,6-dichlorobenzaldehyde-O- (4,6-dichloro)

1,3,5-triazin-2-yl) oxime

In 300 ml of ice-cold acetone were added 18.9 g (0.1 mol) of 2,6-dichlorobenzaldoxime and 18.4 g (0.1 mol) of cyanuric chloride. The pH of the resulting solution was maintained at 6 by the addition of 5% sodium bicarbonate solution. After a three-hour stirring, during which time the pH was maintained at 6, crystals precipitated out, which was added by suction filtration, washed three times with 100 ml of 20% igetn, washed aqueous acetone and _o in a vacuum oven for about 18 hours at 60 ° C were dried to 4.92 g (0.02 mol) of 2,6-dichlorobenzaldehyde-O- (4,6-dichloro-1,3,5-triazin-2-yl) oxime having a melting point of 134.9 ° to give 135.9 ° C. The elemental analysis of the product gave the following:

Analys: C ₁₀ H ₄ Cl ₄ N ₄ O

Calculated: C - 35.54, H - 1.19, N - 16.58.

Determined: C - 35.78, H - 1.04, N - 16.40.

This compound will be referred to as Compound 98 below.

Example XXXVII:

Preparation of N- (2,4-dichlorophenyl) -N ^l - (4,6-dichloro-

1.3.5-triazln-2-yl) hydrazine

Bine portion of 2,4-dichlorophenyl hydrazine to 4.3 g (0.02 mol) was combined with 5.64 g (0.03 mol) cyanuric chloride in the presence of 3.11 g (0.03 mol) of 2,6-lutidine in 125 ml of CH ₂ Gl ₂ treated in a similar manner and in the same way as was the case in Example XXXII. After the reaction mixture is stirred at room temperature for about 18 hours, it is concentrated under reduced pressure and the residue is recrystallized from CHCl- to give 3.4 g (0.01 mol) of N- (2,4-dichlorophenyl) -H '. - (4,6-dichloro-1,3,5-triazin-2-yl) hydrazine in the form of colorless needles with a melting point of 185.0 ° - 1% 0 ° C (decomposition) to give. The elemental analysis of the product gave the following:

Analysis: C ₉ H ₅ Cl ₄ N ₅

Calculated: C - 33.26, H - 1.55, M - 21.55. Calculated: C - 32.88, H - 1.60, N - 20.74.

This compound will be referred to as Compound 99 below.

Example XXXVIII:

Preparation of N - ^^ - Dichlorophenyl ^ - N - ^ ö-dichloro- 1,3,5-triazin-2-yl) methanesulfonamide

Tell A. Preparation of 2,4-diochlorophenyl (methanesulfonamide)

Into a magnetically stirred solution containing 13.5 g (0.08 mol) of 2,4-dichloroaniline, 10.1 g (0.1 mol) of triethylamine and 80 ml of dry tetrahydrofuran was added dropwise a solution containing 11, 5 g (0.1 mol) of methanesulfonyl chloride in 10 ml of tetrahydrofuran. After the addition was complete, a white precipitate settled. Stirring was continued at room temperature for about 16 hours, then the mixture was heated to reflux for 4 hours. The product was isolated by cooling, filtering to remove the precipitate and concentration under reduced pressure to yield 21.6 g of a yellow solid. Chromatography on silica gel using a 9: 1 toluene-butyl acetate eluent gave 1.5 g (0.006 mol) of 2,4-dichlorophenyl (methanesulfonamide) as a yellowish solid. Nuclear magnetic resonance analysis of the product revealed the following: NMR _(CDCl3) A 3.10 (3H, s), 7.0 (1H, bs), 7.37 (1H, dd, J: 2.9 Hz), 7, 55 (1H, d, J: 2 Hz), 7.71 (ΪΗ, d, J: 9 Hz) Particles / Mill.

Part B. Preparation of N- (2,4-dichlorophenyl) -N- (4,6-dichloro-1,3,5 -triazine: tn-2-yl) methanesulfonamide

Using a similar procedure to Example XXXVII, 1.15 g (0.006 mol) of cyanuric chloride was treated with a, 5 g (0.006 mol) of 2,4-dichlorophenylmethanesulfonamide and 670 ml (0.006 mol) of 2,6-lutidine. A colorless precipitate was collected by filtration, and the filtrate was concentrated under reduced pressure to give 2.8 g of a yellow solid. This was subjected to flash chromatography on silica gel using a 3: 1 hexane-ethyl acetate eluent to give 1.6 g of a yellow solid. Recrystallization from toluene-hexane gave 1.0 g (0.003 mol) of N- (2,4-dichlorophenyl) -N- (4,6-dichloro-1,3,5-triazin-2-yl) -methanesulfonamide as a yellow one Solid with a melting point of 145 ° - 157 ° C. In addition, 200 mg of yellow needles were obtained with a melting point of 154.5 ° - 157 ° C. The nuclear magnetic resonance analysis of the product gave the following:

NMR _(CDCl3): J 3.74 (3H, s), 7.10 to 7.68 (3H, m) particles / Mill. IR (CHCl ₃ ) 1540, 1590 cm ^-1 .

¹³ C-HMR (CDCl-) i 171.60, 165.40, 136.98, 134.00, 133.08, 130.97, 130.51, 128.64, 43.50 particles / mill.

This connection will be referred to as compound 100 below. '-

Example XXXIX:

Preparation of 2-Banzyloxy-4,6-dichloro-1,3,5-triazine

In a magnetically stirred solution containing 4.22 g (0.04 mol) of benzyl alcohol in 15 ml of acetone and adjusted to a temperature of

When cooled to ^0-5 ° C, 4.18 g (0.04 mol) of 2,6-lutidine were added dropwise, followed by a solution containing 7.2 g (0.04 mol) of cyanuric chloride in 185 ml Acetone contained. After the completion of the feed, the reaction mixture was stirred at 0 ° C for about one hour and then warmed to room temperature. After reaching about 20 C, a precipitate of lutidine hydrochloride was separated and filtered out. The filtrate was poured onto ice, whereby the crude product precipitated. This crude product was washed with water and dried to give 5.79 g of the material. Two recrystallizations from hexane gave 0.41 g (0.002 mol) of 2-benzyloxy-4,6-dichloro-1,3,5-triazine with a melting point of 78-81.5 C. The magnetic resonance analysis of the product gave the following: NMR (CDCl ₃ ):, {5.55 particles / mill. (2H, s, CH _3), 7.46 (5H, s, aromatic).

This connection will be referred to as compound 101 below.

Example Xl:

Preparation of 2- (2 ', 4'-dichlorobenzyl) -4,6-dichloro-1,3,5- triazine

A portion of magnesium turnings of 1.2 g (0.05 mol) and 20 ml of ether were added to a 100 ml round-bottomed three-necked flask under a nitrogen atmosphere. Two drops of a solution containing 9.7 g (0.05 mole of 2,4-dichlorobenzyl chloride in 15 mL of ether to initiate the reaction were added and the remaining portion of this solution was then added rapidly to cause vigorous reflux.

The Grignard reagent prepared above was added dropwise to a mixture of 9.2 g (0.05 mole) of cyanuric chloride and 125 ml of ether which was cooled to a temperature of 3 ° C. An exothermic reaction to 7 ° C and the formation of a white precipitate were observed while the addition was continued. Stirring was continued at room temperature for about 16 hours, and the resulting heterogeneous mixture was filtered to remove the magnesium salt. The filtrate was washed with water and the organic phase was dried over MgSO4. and concentrated under reduced pressure to give 12.6 g of a yellow pesticide. A 4.0 g portion of this material was chromatographed on silica gel using 9: 1 hexane and EtOAc as the eluent to give 2.9 g of the product. Recrystallization from hexane gave 1.7 g (0.005 mol) of 2- (2 ', 4'-dichlorobenzyl) -4,6-dichloro-1,3,5-triazine as colorless needles with a melting point of 110 ° -112 , 5 ° C. The elemental analysis of this product gave the following:

Analysis: C ₁₀ H ₅ Cl ₄ N ₃

Calculated: C - 38.87, H - 1.63, N - 13.60. Calculated: C - 38.71, H - 1.70, N - 13.51.

This connection will be referred to as connection 102 below.

Example XII:

Preparation of 2- (2 ', 4'-dichloro) kαyl) -4 _s 6-dichloro-1,3,5-triazine

A Grignard reagent was prepared from 11.1 g (0.04 mol) of 2,4-dichloroiodobenzene in the same manner as in Example XI. The reagent was added dropwise to a solution of 7.5 g (0.04 mol) of cyanuric chloride in 75 ml of dry tetrahydrofuran cooled to a temperature of 3 ° C. This gave an exothermic reaction to 8 C and the formation of a white solid. The reaction mixture was stirred at room temperature for seven hours and then heated to reflux for three days. The solid was separated by filtration and a black filtrate was separated under reduced pressure. The residue was partitioned between EtOAc and water and the organic phase was dried over MgSO 4. dried and concentrated to yield 14.9 g of a black solid. Most of the unreacted cyanuric chloride was distilled out using a Kugelrohr apparatus. The residue was then applied to silica gel using hexanes s

EtOAc in the ratio of 9: 1 as the elution medium chromatographed. This gave 5.4 g of a raw material. The sublimation (0.05 mm Hg, 80 ° -85 ° C) gave 2.0 g (0.007 mol) of 2- (2 ', 4'-dichlorophenyl) -4,6-dichloro-1,3,5-triazine as a colorless solid with a melting point of 111 ° -115 ° C. The elemental analysis of the product gave the following:

C ₉ H ₃ Cl ₄ N ₃

Analysis:

Calculated: C ~ - ~ 36.65, H - 1.03, N - 14.25. Determined / C - 34.22, H - 0.92, H - 13.20.

This connection is hereinafter referred to as connection 103.

Example XLII:

Preparation of 2,4-dichloro-6-phenyl-1,3,5-triazine

A portion of clean magnesium turnings at 1.40 g (0.06 mol) was placed in suspension in 4 mL of ethyl ether under a dry nitrogen atmosphere in a 50 mL reaction flask equipped with an addition funnel. Bromobenzene (9.48 g, 0.06 mol) and about 21 ml of ether were added to the addition funnel of the bottle and about 2 ml of this solution was added to the bottle, which was heated to initiate the reaction. The residual bromobenzene solution was added over a period of about one hour to give a controlled reflux rate. The mixture was stirred at room temperature for about 16 hours and then heated to reflux. The Grignard reagent prepared above was then transferred by syringe to a dry addition funnel attached to a stirred, nitrogen-purged, dry flask containing a solution of 8.15 g (0.04 mol) cyanuric chloride in 75 ml benzene which was cooled to a temperature of 3C. The Grignard reagent solution was added dropwise with stirring and the resulting mixture was allowed to warm to room temperature over a period of 4 days. This reaction mixture was quenched with 50 ml of water and extracted with ether, whereupon the organic layers were dried and evaporated solvent-free to give a solid. Crystallization from hexane gave 4.91 g (0.05 mol) of a first crop of product which was recrystallized from cyclohexane and then vacuum sublimed to give 2,4-dichloro-6-phenyl-1,3,5-triazine in the form of a white, crystalline material having a melting point of 117 ° -118 ° C. The elemental analysis of the product revealed the following:

Analysis: CqH ₁ -CIpIJ ^

Calculated: C - 47.80, H - 2.23, N - 18.58. Calculated: C - 47.50, H - 2.26, K - 18.49.

This connection will be referred to as connection 104 below.

Example ZLIII: Preparation of 2- (1-Maphthyl) -4,6-dichloro-1,3,5-triazine

To, 0.66 g (0.03 molar magnesium turnings) was added a solution containing 3.77 ml (0.03 mol 7-bromonaphthalene in 50 ml dry tetrahydrofuran.) The resulting mixture was stirred at room temperature for 20 minutes Added to 150 ml of dry tetrahydrofuran and the mixture stirred at room temperature under a Stickstoffatmosphä re over a period of one hour.

The Grignard reagent prepared above was added to an addition funnel and added dropwise to a solution containing 5.0 g (0.03 mol) of cyanuric chloride in 300 ml of dry tetrahydrofuran at room temperature. After this mixture was stirred for three hours, the solvent was evaporated to give a solid residue which was partitioned between 10% aqueous HaOH solution and Ht "O. The Et ₂ O layer was over anhydrous WagSO. stirred and evaporated, and the residue was purified by preparative plate chromatography (silica gel) using 20 % EtOAc in hexane to give 160 mg (0.0006 mol) of 2- (1-naphthyl) -4,6-dichloro-1, 3,5-triazine as a yellow solid with a melting point of 166 ° -167 ° C. The elemental analysis of the product gave the following

Analysis: C ₁ OH ₇ Cl ₂ M ₃ Calculated: C - 56.54, H - 2.56

 Determined: C - 55.27, H - 2.62.

This connection is hereinafter referred to as connection 105.

Example XLIV:

Preparation of 2- (2-naphthyl) -4,6-dichloro-1,3,5-triazine

In the same manner as in Example XLIII, but using ethyl ether as a solvent instead of tetrahydrofuran and changing that the Grignard reagent was prepared from 2-bromonaphthalene in ether under reflux over a period of 1.5 hours, was prepared 2- (2-Maphthyl) -4,6-dichloro-1,3,5-triazine having a melting point of 193 ° - 194 ° C. The elemental analysis. of the product gave the following:

Analysis: C ₁₃ H ₇ Cl ₂ N ₃ '

Calculated: C - 56.54, H - 2.56, K - 15.22, Cl - 25.68. Determined: C - 54.48, H - 2.63, N - 14.54, Cl - 27.98.

This connection will be referred to as connection 106 below.

Example XLV: Preparation of 2-benzyl-4,6-dichloro-1,3,5-triazine

A Grignard reagent prepared from 1.40 g (0.06 mol) of magnesium and 0.91 g (0.09 mol) of benzyl chloride was charged with 8.15 g (0.04 mol) of cyanuric chloride As in the example XLII responds. The crude product (2.70 g) was vacuum sublimed and then sublimed again to give 0.99 g (0.004 mol) of pure 2-benzyl-4,6-dichloro-1,3,5-triazine having a melting point of 82 ° -85 ° C to give. The elemental analysis of the product gave the following:

Analysis: C ₁₀ H ₇ Cl ₂ W ₃

Calculated: C - 50.02, H - 2.94, H - 17.49. Determined: C - 49.90, H - 2.85, K - 17.57.

This connection is hereinafter referred to as connection 107.

Example XLVI:

Preparation of 2- (2 ', 4'-dichlorobenzylthio) -4,6-dichloro

1,3,5-triazine .

Part A. Preparation of 2,4-dichlorobenzylmercaptan

A mixture of 4.8 g (0.06 mol) of thiourea, 12.2 g (0.06 mol) of 2,4-dichlorobenzyl chloride and 50 ml of ethanol was stirred and refluxed under nitrogen atmosphere for 4 ¹ / Heated for 2 hours. Then, the reaction mixture was cooled and a solution of 6.25 g (0.16 mol) of NaOH in 50 ml of water was added dropwise. After completion of the addition, the mixture was heated to reflux for a period of two hours, during which time it turned yellow. Subsequently, the stirring was continued at room temperature for a period of 2 days. Then, the ethanol was removed under reduced pressure, and the aqueous residue was extracted with CHgCl ₂ (6 κ 100 ml). The combined organic layers were over MgSO4. dried and concentrated to give 12.1 g (0.06 mol) of 2,4-dichlorobenzylmercaptan as a tan colored liquid. Magnetic resonance analysis of the product gave the following: HMR (CDCl ₃ ); S 1.90 (1H, t, J = 8 Ήζ), 3.79 (2H, d, J = 8Hz), 7.18-7.33 (2H, m), 7.33-7.48 ( 1H, m) particles / Mill.

Part B. Preparation of 2- (2 ', 4'-dichlorobenzylthio) -4,6- dichloro-1,3,5-triazine

To a solution containing 6.5 g (0.03 mol) of cyanuric chloride in acetone was added 6.7 g (0.03 mol) of 2,4-dichlorobenzylmercaptan prepared in Part A. A similar procedure was used as in Example XXXII to produce the product. The crude product was on

Silica gel was randomly chromatographed using a 1: 1 hexane-toluene eluant to give 2.0 g of the pure product. Recrystallization gave 1.9 g (0.006 mol) of 2- (2 ', 4'-dichlorobenzylthio) -4,6-dichloro-1,3,5-triazine having a melting point of 55.5 ° to '58.5 ° C. Elemental analysis of the product showed the following:

Analysis: C ₁₀ H ₅ Cl ₄ K ₃ S

Calculated: C -.35.22, H-1.48, N-12.32.- · Averages: 0-35.56, H-1.62, N-12.47.

This connection is hereinafter referred to as connection 108.

Example XLVII:

Preparation of 6-chloro-2,4-t> is- (2 ', 4'-diochlorobenzylthio) -

1,3,5-triazine ,

The early chromatographic fractions of Example XIVI contained 2.3 g of a colorless solid which was recrystallized from hexane to give 2.2 g (0.004 mol) of 2,4-t-iso- (2 ', 4'-dichloro-topicylthio) -6- chloro-1,3,5-triazine having a melting point of 76.0 ° -80.0 ° C. The elemental analysis of the product gave the following:

Analysis: C ₁₇ H ₁₀ Cl ₅ KoS ₂

Calculated: C - 41.03, H - 2.03, H -8.44. ,

Determined: C - 41.35, H-2.25, N - 8.93. "

This compound is hereinafter referred to as Compound 109.

Example XLVIII:

Preparation of 2- (2 ', 4'-dichlorophenethoxy) -4,6-dichloro- 1,3,5-triazine

Part A. Preparation of 2,4-dichlorophenethoxy alcohol

A portion of 124 ml of a 1 M solution of the borane-tetrahydrofuran complex in tetrahydrofuran was placed in a 500 ml three-neck round bottom trap and cooled to 0 ° C with an ice bath. A solution containing 12.7 g (0.06 mol) of 2,4-dichlorophenylacetic acid in 100 ml of tetrahydrofuran was added dropwise at a rate such that the temperature was kept below 5 ° C. During the addition, gas evolution was observed. After completion of the addition, the colorless mixture was heated to reflux for one hour and then stirred at room temperature for about 16 hours. The reaction mixture was then treated with 125 ml of methanol. The solvent was removed under reduced pressure and the residue was dissolved in ether and washed with 5% aqueous NaOH. The organic phase was over MgSO 4. dried and concentrated to give 12.7 g (0.066 mol) of 2,4-dichlorophenethyl alcohol as a colorless oil. The magnetic resonance resonance analysis of the product gave the following: NMR (CDClO) * & 1.62 (1H, s), 2.98 (2H, t, J = 7 Hz), 3.88 (2H, t, J = 7 Hz) , 7.10-7.48 (3H, m) particles / Mill.

Part B. Preparation of 2- (2 ', 4'-dichlorophenethoxy) -4,6- dichloro-1,3,5-triazine

A solution containing 6.45 g (0.04 mol) of cyanuric chloride in acetone was prepared by a similar procedure as in Example XXXII with 6.7 g (0.04 mol) of 2,4-DichlorophenethyIaI-kohol, in part A was prepared, treated. The crude product was chromatographed on silica gel using a toluene-hexane eluant at a 1: 1 ratio. The recovered material was recrystallized from hexane to give 2.2 g (0.006 mol) of 2- (2 _'4'-t Dichlorophenethoxy) -4,6-dichloro-i, 3,5-triazine in the form of colorless needles having a melting point of 106.5 ° - 108 ° C. The elemental analysis of the product gave the following:

Analysis: C ^^

Calculated: C - 38.97, H - 2.08, N - 12.40. Determined: C - 39.14, H - 2.35, N - 12.54. This connection will be referred to as connection 110 below.

Example XLIX:

Preparation of N- (4,6-dichloro-1,3,5-triazin-2-yl) -2,4-

dichloro benzamide

In a stirred solution containing 2.2 g (0.01 mol) of 2,4-dichloro-benzoyl chloride, 1.7 g (0.01 mol) of 2-amino-4,6-dichlorotriazine and 80 ml of acetone and cooled to a temperature of 0 C, a solution containing 400 mg NaOH in 4 ml water was added. The HaOH solution was added at such a rate as to keep the temperature below 4 ° C. After completion of the addition, the stirring was continued for 3 hours. The reaction mixture was then poured onto ice to give a milky solution which was extracted with dichloromethane (4 x 75 ml). The combined extracts were over MgSO4. and concentrated under reduced pressure to give 3.6 g of a colorless solid. Relaxation chromatography using hexane-EtOAc eluent in a ratio of 9: 1 gave 900 mg of a colorless solid. This material was then dissolved in CHgCIg and washed with saturated aqueous NaHCO _3. The organic layer was dried over MgSO ₄ and concentrated on a rotovap. The residue was recrystallized from toluene-hexane to give 3OO mg (0.001 mol) of N- (4,6-dichloro-1,3,5-triazin-2-yl) -2,4-dichlorobenzamide) having a melting point of 162 ° - 166 ° C. The elemental analysis of the product gave the following:

Analysis: Ο ^ Η, ΟΙ, Ν-, Ο

Calculated: C - 35.54, H - 1.19, N - 16.58.

Determined: C - 36.03, H - 1.54, N - 16.23.

This connection will be referred to as connection 111 below. · Example L:

Preparation of N- (4,6-dichloro-1,3,5-triazin-2-yl) -2,4-dichloroacetanilide

Part A: Preparation of 2.4-Diehloroazetanilide

Into a three-necked round-bottomed flask of 100 ml capacity was placed 20 ml (0.21 mol) of acetic anhydride under a nitrogen atmosphere and cooled to a temperature of 3 ° C in an ice bath. Thereafter, 13.5 g (0.08 mol) of 2,4-dichloroaniline were added in small portions. The mixture was stirred at room temperature for another 17! Hours. The solid, colorless material that formed was removed by filtration and dried in a vacuum oven to give 16.5 g (0.08 mole) of 2,4-dichloroacetanilide. The nuclear magnetic resonance analysis of the product showed the following: HMR (CDCl ₃ ): O 2.22 (3H, s), 7.18 (1H, dd), 7.34 (1H, d), 7.40-4.48 ( 1H bs), 8.28 (1H, d) particles / mill.

Part B. Preparation of W- (4,6-dichloro-1,3,5-triazin-2-yl) -2,4-diochloroethane etanilide _; ,

Using a similar procedure to Example XLIX, a mixture containing 6.0 g (0.03 mol) of 2,4-dichloroacetanilide as prepared in Example A was added to 5 g (0.03 mol) of cyanuric chloride and 5 g 120 ml of acetone, treated with a solution containing 1.18 g (0.03 mol) of HaOH in 12 ml of water. The work up gave 10.5 of a colorless oil which was chromatographed on silica gel using 9: 1 hexane-ethyl acetate eluant. Recrystallization from hexane gave 6.4 g (0.02 mol) of colorless prisms from H- (4,6-dichloro-1,3,5-). triazin-2-yl) -2,4-dichloroacetanilide having a melting point of 106 ° -108.5 ° C. The nuclear magnetic resonance analysis of the product showed the following: NMR (CDCl ₃ ): δ 2.82 (3H, s), 7 , 18 (1H, d, J = 9Hz), 7.45 (1H, dd, J = 2.9Hz), 7.6 (1H, d, J = 2Hz) Particles / Mill.

This product will be referred to as compound 112 below.

Example LI: manufacture; of 2,4-dichloro-6-phen.ylethynyl-1,3,5-triazine

To ethyl magnesium bromide (49 ml of a 2 M solution in tetrahydrofuran, 0.1 mol) was added phenylacetylene (10 g, 0.1 mol) in tetrahydrofuran (50 ml). Dripping procedure. Cyanuric chloride (12 g, 0.07 mol) in benzene (65 ml) was added keeping the reaction temperature below 25 ° C. After six hours of stirring, the solvent was evaporated and the residue was extracted with ether. The solution. was evaporated, and the residue was triturated with ether to give 1.5 g (0.006 mol) of 2,4-dichloro-6-phenylethynyl-1,3,5-triazine as a yellow solid having a melting point of 125 ° To give 131 ° C. Elemental analysis of the product showed the following: Analysis: C ₁₁ H ₅ Cl ₂ Ii,

Calculated: C -52.83, H-2.02, N-16.80. Determined: C - 53.37, H - 2 * 28, K - 16.25.

This connection is hereinafter referred to as connection 113.

Example LII:

Preparation of 2-chloro-4- (phenylethynyl) -6- (2 ·, 2 ', 2'-trifluoroethoxy) -1,3,5-triazine and 2,4-bis- (2', 2 ·, 2 ' trifluoro ethoxy) -6-phenylethynyl) -1,3,5-triazine

In the same manner as in Examples XXVIII and XXIX, 2,4-dichloro-6-phenylethynyl-1,3,5-triazine was reacted with 2,2,2-trifluoroethanol to give 2-chloro-4- (phenylethynyl ) -6- (2 · , 2 > , 2'-t-rif luoroethoxy) -1,3,5-triazine having a melting point of 48 ° - 51 ° C and also 2,4-bis- (2 ·, 2 '-2'-trifluoroethoxy) -6- (phenylethynyl) -1,3,5-triazine with a melting point of 68 ° -72 ° C. The elemental analysis of the two products gave the following:

2-Chloro-4- (phenylethynyl) -6- (2 ', 2', 2'-trifluoroethoxy) -1,3,5-triazine

Analysis: Cjoj

Calculated: C - 49.78, Ή - 2.25, P - 18.17.

Determined / C - 50.98, H - 2.42, P - 17.11.

This compound is hereinafter referred to as compound II4.

2,4 ~ bis- (2 ', 2' _S 2'-trifluoroethoxy) -6- (phenylethylnyl) -1,3,5-triazine _i

Analysis: C ₁₅ H ₉ P ₆ K ₃ O ₂

Calculated: C - 47.76, H - 2.40, H - 11.14, P - 30.22.

Determined: C - 48.42, H - 2.32, K - 11.26, P - 29.33.

This connection will be referred to as connection 115 below.

Example LIII

Preparation of 2- [4- (phenylazo) phenoxyj-4,6-dichloro-1,3,5-

triazine

Into a 250 ml round-bottomed three-necked flask equipped with thermometer, addition funnel and nitrogen inlet was added cyanuric chloride (4.67 g, 0.03 mol) dissolved in 30 ml of acetone and cooled to 0 ° - 5 ° C in an ice bath. The addition funnel was filled with a solution containing 4-phenylazophenol (5.0 g, 0.03 mol) and 2,6-lutidine (2.91 ml, 0.03 mol) in 30 ml of acetone, and this mixture became added dropwise, the reaction temperature was maintained between 0 and 5 C. After the addition was complete, the reaction mixture was stirred at room temperature for 16 hours, filtered through a celite pad, and ice-water (40 ml) was added. The forming precipitate was recorded with a Buchner funnel. The precipitate was dissolved in EtOAc, washed with saturated HaHCO-j and water, dried (MgSO 4) and concentrated. The crude product was recrystallized twice from hexane: CHCl- (2 to 1) to give 750 mg (0.002 mol) of 2- (4- (phenylazo) phenoxy] -4,6-dichloro-1,3,5-tria3ine with a

Melting point of 162.0 ° - 164.0 ° C. The EletnentaranalyQe of the product gave the following:

Analysis: G ₁₅ H ₉ Cl ₂ W ₅ O

Calculated: C - 52.04, H - 2.62, K - 20.23. Calculated: C - 52.37, H - 2.82, N - 20.20. Analysis: C ₁₂ H ₄ Gl ₄ K ₆ O ₂

Calculated: C - 35.50, H - 0.99, M - 20.70. Finds: C - 35.07, H - 0.91, K - 20 ^ 0.

This connection will be referred to as connection 117 below.

This connection is hereinafter referred to as connection 116.

Example LIV:

Preparation of 2,2'- [1,3-phenylenebis (oxy) J-bis [4,6-dichloro]

ro-1.3.5-triazinj

Into a 250 ml round-bottomed three-necked flask equipped with nitrogen inlet, thermometer and addition funnel was added cyanuric chloride (13.46 g, 0.07 mol) dissolved in 100 ml of acetone and placed in an ice bath on a Temperature of 0 ° - 5 ° C was cooled. Reeorcinol (4.0 g, 0.04 mol) and 2 ', 6-lutidine (8.50 ml, 0.07 mol) dissolved in 100 ml of acetone were added to the addition funnel. This solution was slowly added dropwise while maintaining the reaction temperature at 0 ° -5 ° C. Then, the reaction mixture was stirred at room temperature for 16 hours. At this time, the precipitate was removed by filtering through a celite pad. Addition of ice-water (40 ml) to the filtrate gave an oil which was extracted from the aqueous solution with EtOAc (2 × 150 ml). The combined organic layers were dried (MgSO ₄ ) and concentrated in vacuo . The crude product was purified by flash chromatography on silica gel (eluant 5 % EtOAc / hexane) to give 2.8 g (0.007 mol) of 2,2 '- $, 3-phenylenebis-bis-oxy-bis-dichloro-i, 3,5- triazine in the form of a white solid having a melting point of 145 ° -148 ° C. Elemental analysis of the product gave the following:

Example LV:

Other compounds were prepared in the same way as in the LIV example. The structures and analytical data for compounds 118 to 121 used in the examples below for the reduction of plant moisture loss are given in Table F below.

Table F

Representative heterocyclic, nitrogen-containing compounds

Cl.

cl "

Cl

- <

Cl

Verb «- Substituents elemental analysis

calculated

determined

Melting point ¹ C

point, o

^{35 '50 0>} " ^2Ol7 ° ³⁶ ' ^{04 1} · ^{19 19f94 253} '° ^to

257.0

48,11 ² » ⁶ 9 16 | O3 48,06 2,67 15,92 115,0 to

Table F (continued)

Representative heterocyclic, nitrogen-containing compounds

Cl

η 0'Vo-X ₄ -O- (O

Cl '

.cl

¹ Cl

Verb. Substituents Elemental Analysis IS X.

melting

calculated

point, determined o "

HN

HN

0 / - ^c - {0 / -38,10 1,52 12,69 38,04 1,69 12,31 228,0 -

Cl CH ₃ Cl

232.0

42.05 1.57 16.35 42.26 2.00 16.65 161.0 -

163.0

Example LVI:

Preparation of bis (4,6-dichloro-1,3,5-triazin-2-yl) amine

In a 250 ml round-bottomed, three-necked round bottom flask equipped with a thermometer and addition funnel was added cyanuric chloride (2.78 g, 0.02 mol) in 50 ml of acetone heated to a temperature of 0 ° -5 ° C was cooled, · given. It was 2-amino-4,6-dichloro-1,3,5-

"triazine (2.48 g, 0.02 mol) was added and the reaction temperature was brought to 0-5 ° C. A cold solution of NaOH (0.6 g, 0.02 mol) in 6 mL of water became slow drops-

* added over a period of 20 minutes. Thereafter, the reaction mixture was stirred at room temperature for 4 hours and then poured into 250 ml of ice water in which 4.5 g of DJagCO was dissolved. The solution was

, to remove a solid precipitate (tris [4,6-dichloro-1,3,5-triazin-2-yl-amine) and the filtrate was acidified. A white precipitate was caught with a Buchner trichetr. The resulting powdery crystals (1.51 g) were sublotted over a period of 2 days to give 0.97 g (0.003 mol) of pure bis (4,6-dichloro-1,3,5-triazin-2-yl ) amine with a melting point of 204.0 to 207.0 ° C. The elemental analysis of the product gave the following:

C ₆ HCl ₄ H ₆

Analysis:

Calculated: C - 23.03, H - 0.32, N - 31.33. Calculated: C - 22.67, H - 1.20, N - 30.67.

This connection is hereinafter referred to as connection 122.

Example LVII: 'Preparation of N, H-bis (4,6-dichloro-1,3,5-triazin-2-yl) -4'- fluorobenzenamine .

N, N-bis (4,6-dichloro-1,3,5-triazin-2-yl) -4'-fluorobenzenamine was purchased from Maybridge Chemical Company, Limited, Trevillet, Tintagel, Cornwall, United Kingdom, and toluene recrystallized. The melting point was determined to be 231.0 ° - 233.0 ° C. Elemental analysis of the compound gave the following:

Analysis: C ₁₂ H ₄ Ql ₄ FN ₇

Calculated: C - 35.41, H - 0.99, N - 24.08. Determined: C - 34.41, H - 1.06, N - 23.82.

This connection will be referred to as connection 123 below.

Example LVIII:

Preparation of W, N-bis (4,6-dichloro-1,3,5-triazin-2-yl) -3'- chloro-4'-fluorobenzenamine

N, N-bis (4,6-bichloro-i, 3,5-triazin-2-yl) -3'-chloro-4'-fluorobenzenamine was obtained from Maybridge Chemical Company, Limited,

Trevillet, Tintagel, Cornwall, United Kingdom, and recrystallized from toluene. The melting point was determined to be 228.5 ° - 229.5 ° C. Elemental analysis of the compound gave the following:

G ₁₂ H ₃ GI ₅ FM ₇

Analysis:

Calculated: C-32.65, H-0.68, H-22.21. Determined: C - 32.21, H - 0.66, M - 21.65.

This connection will be referred to as connection 124 below.

Example LIX:

Preparation of 2,2'.4.4'-tetrahydorohydrazo-1,3,5-triazine

Into a three-necked round bottom flask with a capacity of 100 ml equipped with a mechanical stirrer, thermometer, addition funnel and nitrogen inlet was added cyanuric chloride (3.68 g, 0.02 mol) in 20 ml of tetrahydrofuran and stirred vigorously to a temperature cooled between -15 ° C and -10 ° C. Hydrazine hydrate (1.90 S »55 S hydrazine content, 0.03 mol) in 4 mL of water was added slowly via the addition funnel keeping the reaction temperature between -15 and -10 ° C. After completion of the addition, the reaction mixture was stirred at 0 C for 15 minutes. Ice-water (40 ml) was added and the aqueous solution was then extracted with EtOAc (2 x 100 ml) and the extracts dried (MgSO 4) and concentrated in vacuo to give 2.92 g (0.009 mol) of 2.2 ', 4,4' · Tetrachlorohydrazo-1,3,5-triazine was obtained as a fine, white solid which began to decompose above 250 ° C. The elemental analysis of the product gave the following:

Analysis:. C ₆ H ₂ Cl ₄ H ₈

Calculated: C - 21.97, H - 0.61, Ή - 34.17. Calculated: C - 23.64, H - 1.34, Ή - 36.23.

This compound will be referred to as Compound 125 below.

Example LX:

Preparation of 2,2 ', 4 "4'-tetrachloroazo -1,3,5-triazine

into a 250 ml round-bottomed three-necked flask equipped with a septum, an acid trap outlet, and a stopper was added 2,2 ', 4,4'-tetrachlorohydrazole-1,3,5-triazine (3.20 g, 0.01 mol) and '100 ml CHCl'. Sodium bicarbonate (1.64 g, 0.02 mol) dissolved in 50 ml of water was then added. The two-phase solution was stirred slowly so that the phases remained separate. Then, a slow stream of Cl ₂ -GaS was bubbled through the OHCl ₃ layer until the CHCl ₃ layer was homogeneous and deep red, ie, for about 75 minutes. At this time, the CHCl 2 layer was separated and washed with water, dried (MgSO 4) and.

concentrated in vaouo to give orange crystals, which were slurried in ether, cooled and filtered. The resulting pale orange solid was recrystallized from CH 2 Cl 2, yielding 2.1 g (0.006 mol) of 2,2 ', 4,4'-tetrachloroazo-1,3,5-triazine having a melting point of 186.0 ° -190 ° C The elemental analysis of the product gave the following:

Analysis: GgCl.K

Calculated: C - 22.11, H - 0.00. N - 34.38. Determined: C - 22.78, H - 0.28, K - 33.98.

This connection will be referred to as compound 126 below.

Example LXI:. ,

Preparation of 2,4-dichloro-6- (4'-formyl-2'-methoxyphenoxy) -

1,3.5-triazine

To a solution containing cyanuric chloride (5.0 g, 0.03 mol) in acetone (H 2 mL) at 0 ° C was added dropwise a solution containing 2,6-lutidine (3.15 mL, 0.03 Mole) and 4-hydroxy-3-methoxybenzaldehyde (4.125 g, 0.03 mol) in acetone (25 mL), keeping the temperature below 5 ° C

has been. After stirring for 2 h, the reaction mixture was filtered and the filtrate was filtered through silica gel and washed with acetone to give 650 mg (0.002 mol) of 2,4-diChIOrO-O- (4'-formyl-2-methoxyphenoxy) -1, 3,5-triazine as a white pesticide with a melting point of 156 ° to 157.5 ° C. The nuclear magnetic resonance analysis of the product gave the following: ¹ H-HMR (GDCl ₃ ): $ 3.8 (s, 3H), 7, 2 to 7.7 (m, 3H), 10.05 (s, 1H) particles / mill.

This compound will be referred to as compound 127 below.

example

Other connections were made in the same way as in the example LXI. The structures and analytical data for compounds 128 to 131 used in the examples below to reduce moisture loss from plants are given in Table G below.

Table G ~~ Representative heterocyclic, nitrogenous compounds [

.cl

Cl

Verb. substituents ElementaranaIys e determined N enamel MS R ₁₇ calculated C H point, ⁰ C C HN

33.68 1.26 13.09 33.61 1.33 13.03 88 -

48.47 1.56 13.05 49.58 1.93 12.49 152

162 Table G (continued)

Representative heterocyclic, nitrogen-containing compounds

MT

Cl

Cl

Verb. Substituents elementary analysis

^V 17

calculated

determined

Melting "point,

H H

130 0

39.44 1.84 15.33 35.36 1.65 16.78 126 bis

135

39.44 1.84 15.33 39.93 1.91 14.63 177 to c§

180

Example LXIII:.

Preparation of 2,4-dichloro-6- (5 ^l -methylisoxazolyl-3'-amino)

no) -1,3,5-triazine __ ^ __

To a solution containing cyanuric chloride (5.0 g, 0.03 mol) in acetone (100 ml) at a temperature of 0 ° C was added dropwise a solution containing 2,6-lutidine (3.15 ml, 0.03 mole) and 3-amino-5-methylisoxazole (2.66 g, 0.03 mole) in acetone (50 ml), keeping the temperature below 5 ° C. After stirring for 2 hours, the reaction mixture was heated to room temperature and then poured into 200 ml of ice-water. The mixture was filtered, the solid dried and recrystallized from chloroform to give 800 mg (0.003 mol) of 2,4-dichloro-6- (5'-methylisoxazolyl-3'-amino) -1,3,5-triazine as a solid with a melting point of 128 ° - 132 ° C. The elemental analysis of the product is as follows:

Analysis: C ₇ H ₅ Cl ₂ H ₅ O

Calculated: C - 34.17, H - 2.05, N - 28.06. Finds: C - 34.24, H - 2.11, N - 28.15.

This connection will be referred to as connection 132 below.

Example LXIV:

Preparation of 2,4-dichloro-6- (2-pyridinylamino) -1,3,5- triazine

To a solution containing cyanuric chloride (18.4 g, 0.1 mol) in acetone (1 ml) and crushed ice-water (200 ml) was added dropwise 2-aminopyridine (9.4 g, 0.1 mol) in Acetone, keeping the reaction temperature below 5 ° C. The amount of acetone was 68 ml. Then, sodium hydroxide (50 ml of a 2N solution, 0.1 mol) was added keeping the temperature below 5 ° C and the pH below 8.0. The reaction mixture was filtered and chromatographed on silica gel to give 590 mg (0.002 mol) of 2,4-dichloro-6- (2-pyridinylamino) -1,3,5-traizin as an orange solid with a melting point of 170 ° Lis ¹ I72 ⁰ C. The elemental analysis of the product gave the following:

Analysis: C ₈ H ₅ Cl ₂ H ₅

Calculated: C - 39.69, H - 2.08, N - 28.93. Calculated: C - 34.08, H - 1.47, K - 27.92.

This connection will be referred to as connection 133 below

 Example LXV:

Preparation of 2-benzoxazolylamino-4,6-dichloro-1,3,5-triazine

Into a mixture containing 2-aminobenzoxazole (1.0 g, 0.007 mol) and cyanuric chloride (1.38 g, 0.007 mol) in acetone (12 ml) was added, at 0 ° C, 5 % sodium hydroxide solution (34 ml ) was added at such a rate that the temperature of the reaction mixture was kept below 10 ° C and the pH between 6.5 and 7.0. After completion of the addition, the reaction mixture was filtered and the solid (0.75 g) recrystallized from chloroform to give 100 mg (0.003 mol) of 2-benzoxazolylamino-4,6-dichloro-1,3,5-triazine as a white solid with a melting point greater than 250 ° C. The elemental analysis of the product revealed the following:

Analysis:. C ₁₀ H ₅ Cl ₂ K ₅ O

Calculated: C - 42.58, H - 1.79, H - 24.83. Calculated: C - 41.68, H - 1.78, K - 23.58.

This compound is hereinafter referred to as compound I34.

Example LXVI:

Preparation of 2-4-dichloro-6- (4'-quinazolinoxy) -1,3,5- triazine

To a mixture containing 4-hydroxyquinazoline (5 g, 0.03 mol) and cyanuric chloride (6.3 g, 0.03 mol) in acetone (110 ml) was added 2% sodium hydroxide solution at such a rate that the temperature of the reaction mixture was kept below 10 C and the pH between 6.5 and 7.0. Upon completion of the addition, the reaction mixture was allowed to warm to room temperature and stirred for about hours. The reaction mixture was filtered, the solid added to a Soxhlet extractor and extracted with refluxing chloroform. Evaporation of the solvent and chromatography on silica gel yielded 100 mg (0.0003 mol) of 2,4-dichloro-6- (4'-quinazolinoxy) -1,3,5-triazine as a solid having a melting point of greater than 250 ° C. The nuclear magnetic resonance analysis of the product gave the following:

¹ H-KMR (CDCl ₃ ): h 7.2-8.2 (particles / mill.) (5H, m), 8.5 particles / mill. (1H, s).

This compound is also referred to as compound 135.

Example LXJTII:

Preparation of 2- (2-carboxyloxy) -4,6-dichloro-1,3,5- triazine

To a mixture containing 2-hydroxy-carbazole (3 g, 0.02 mol) and cyanuric chloride (3 g (0.02 mol) in acetone (130 ml) was added, at 0 ° C, a 2% sodium hydroxide solution (130 ml at a rate such that the temperature of the reaction mixture was kept below 10 ° C and the pH between 6.5 and 7.0 After the completion of the addition, the reaction mixture was stored in a refrigerator for about 16 hours and then the solid Product was filtered and recrystallized from acetone The solid was placed in a Soxhlet extractor and extracted with refluxing chloroform for about 16 hours Evaporation of the solvent gave 3.75 g (0.01 mol) of 2- (2-carbazolyloxy) -4 , 6-dichloro-1,3,5-triazine as a solid having a melting point of 249 ° -256 ° C. Elemental analysis of the product indicated the following:

Analysis: C ₁ I-H ₂ Cl ₂ CO

Calculated: C - 54.40, H - 2.44, N - 16.92. Determined: C - 53.38, H - 2.51, N - 16.50.

This compound is hereinafter referred to as compound 136.

Example LXVIII:

Preparation of 2,4-dichloro-6- [4- (2,3-dimethyl-1-phenyl- 3-pyrazolin-5-onamino) -1,3,5-triazine

To a solution containing cyanuric chloride (18.4 g, 0.1 mol) in acetone (200 ml) and crushed ice-water (200 ml) was added dropwise 4-aminoantipyrine (20.3 g, 0.1 mol) in acetone (180 ml) was added while maintaining the reaction temperature below 5 ° C. Then sodium hydroxide (50 ml of a 2N solution, 0.1 mol) was added, the temperature being below 5 ° C below the pH below 8, 0 were held. The reaction mixture was filtered, the filtrate evaporated to remove the acetone, and the residue extracted continuously with ether over a period of about 16 hours. The solvent was evaporated to give 860 mg (0.003 mol) of 2,4-dichloro-6-i4- (2,3-dimethyl-1-phenyl-3-pyrazolin-5-onamino)] - 1,3,5 triazine as a white solid with a melting point greater than 250 ° elemental analysis of the product gave the following:

C. The

Analysis:

Calculated: C - 47.88, H - 3.45, N - 23.92. Calculated: C - 46.57, H - 3.49, N - 23.05.

Analysis: C ₁₄ H ₁₂ Cl ₂ K ₂ O

Calculated: C - 47.88, H - 3.45, N - 23.92. Determined: C - 46.57, H - 3.49, N -

This connection will be referred to as compound 137 below.

Example LXIX: Preparation of 4,6-dichloro-2- (N-phthalimido) -1,3,5-triazine

In a solution containing 20.8 g (0.1 mol) of cyanuric chloride in 100 ml of acetone was added a suspension of 20.8 g (0.1 mol) of potassium phthalimide in 200 ml of acetone while cooling to a temperature of 0 °. 4 ° C given. The resulting mixture was stirred at ⁰ ° -4 .0 C for three hours and then for about 16 more hours at room temperature. The mixture was filtered and the filtrate was poured into ice-water while trituration to effect precipitation. The mixture was filtered and the solid dried in vacuo to give 17 g of the crude product. This crude product was recrystallized from CHgClg-hexane to give 4.5 g (0.02 mole) of 4,6-dichloro-2- (H-phthalimido) -1,3,5-triazine having a melting point of 176 ° -177 ° C. Elemental analysis of the product showed the following:

Analysis: C ₁₁ H ₄ Cl ₂ M ₄ O ₂ Calculated: C - 44.90, H - 1 yy, 6

 Measured: C - 45.05, H - Γ.97.

This connection will be referred to as compound 138 below.

Example IXX:

Preparation of 4,6-dichloro-2- (H-3,4,5,6-tetrachlorophthalamate)

limido) -1,3,5-triazine J.

In a. Suspension, containing 4.02 g (0.04 mol) of 35% by weight KH in oil, was charged with 100 ml of tetrahydrofuran and a solution containing 3,4,5,6-tetrachlorophthalimide (10.0 g, The mixture was stirred at room temperature for 30 minutes, cooled to 0 ° C, and a solution was added which contained 6.47 g (0.04 mol) of tetrahydrofuran. Cyanuric chloride in 150 ml of dry tetrahydrofuran. The mixture was stirred at room temperature for about 16 hours, filtered and the filtrate poured onto ice-water. The precipitate was filtered, yielding 20 g of a crude product. This material was extracted with hot CH ₂ Gl ₂ . The methyl trifluoride solution was cooled to room temperature and hexane was added to crystallize the product. Filtering gave 700 mg (0.002 mol) of 4,6-dichloro-2- (N-3 ', 4 ", 5,6-tetrachlorophthalimido) -1,3,5-triazine as a white solid with a melting point of 298 ° - 300 ° C. The infrared analysis of the product gave the following:

IR (KBr) 1745, 1510, HOO, 1370, 1300 and 1235 cm " ¹ .

This connection is hereinafter referred to as connection 130

 Example LXXI:

Preparation of 2- (4 ', 6'-dichloro-1 ·, 3', 5'-triazin-2'-yl) -1,2.-benzisothiazol-3 (2H) one-1,1-dioxide

In a solution containing 100 g (0.054 mol) of cyanuric chloride in 200 ml of acetone was added a suspension containing 10 g (0.054 mol) of saccharin in 100 ml of acetone. The mixture became homogeneous after several minutes and 5.5 ml (0.054 mol) of 2,6-lutidine were added, followed by stirring at room temperature for about 16 hours under a nitrogen atmosphere. Then the suspension was filtered, the filtrate evaporated and the residue partially crystallized from CH ₂ Cl ₂ -hexane. This pesticide was filtered and the filtrate was evaporated to give a residue which was recrystallized from CHgClg-hexane and 2.0 g (0.006 mol) of 2- (4 ', 6'-dichloro-1', 3 ', 5'-triazin-2'-yl) -1,2-benzisothiazol-3 (2H) one-1,1 dioxide. The elemental analysis of the product gave the following:

Analysis: C ₁₀ H ₄ O ₃ Cl ₂ N ₄ S

Errechrxfc: C - 38.60, H - 1.30, N - 18.01, Cl - 22.79. Determined: C - 36.59, H - 1.43, N - 16.27, Cl - 20.71.

This compound is hereinafter referred to as compound HO.

Example LXXII:

Preparation of 2,4-dichloro-6-triethylsilylethynyl 1-1,3,5- triazine

Ethylmagnesium bromide (35.4 ml of a 2 M tetrahydrofuran solution) was added dropwise to a solution of trimethylsilylacetylene (14, 4 ml, 0.1 mol) in tetrahydrofuran (80 ml) at a temperature of -60 ° C Stirred to room temperature, stirred for 2 hours and then heated at 40 ° C for 1 hour. The solution was cooled to room temperature and then added dropwise to a solution of cyanuric chloride (12 g, 0.07 mol) in tetrahydrofuran (65 mL). added. After 1 h at room temperature, the solvent was evaporated and the residue was extracted with ether. The ether was evaporated and the residue chromatographed on silica gel to give 1.2 g (0.005 mol) of 2,4-dichloro-6-trimethylsilylethyne 1- 1,3,5-triazine in the form of a brown oil. The elemental analysis of the product gave the following:

Analysis: CgH ₉ Cl ₂ N ₃ Si ₁

Calculated: C - 39.03, H - 3.69, N - 17.07. Determined: C - 39.67, H - 3.90, N - 15.97.

This compound is hereinafter referred to as compound I4I.

Example LXXIII:

Preparation of 2,4-dichloro-6-ethoxyethynyl-1 .3.5-triazine

In ethyl magnesium bromide (21.0 ml of a 2M solution in tetrahydrofuran) was added dropwise a solution of ethoxyacetylene (3.0 g, 0.04 mol) in tetrahydrofuran (21 ml) at a temperature of 0 ° C. After completion of the addition, the Bauer's reaction mixture was heated at 40 ° C for one hour, then cooled to 0 ° C and added dropwise to a solution of cyanuric chloride (7.9 g, 0.04 mol) in tetrahydrofuran (21 ml). The reaction mixture was stirred for about 16 hours, the solvent evaporated and the residue extracted with ether. The ether was evaporated and the residue was chromatographed on silica gel to give 1.5 g (0.007 mol) of 2,4-dichloro-6-ethoxyethynyl-1 »3,5-triazine as an orange oil. The nuclear magnetic resonance analysis of the product showed the following: ¹ H-HMR (CDCl ₃ ): i 1.4 (t, 3H), 4.55 (q, 2H) particles / Mill.

This connection is hereinafter referred to as connection 142.

BeispielLXXIV:

Preparation of 2,4-dichloro-6-methylsulonamido-1,3,5-triazine in

Into a mixture containing methanesulfonate nitride (9.5 g, 0.1 mol) and barium hydroxide (4 g, 0.1 mol) in water (0.5 L) was added a solution at a temperature of 25 ° C, the cyanuric chloride (18.4 g, 0.1 mol) in acetone (100 ml) ent_ held. Finally, the addition was added dropwise. Sodium hydroxide (4.0 g, 0.1 mol) in water (25 mL) where _{T was} kept below 8.0 at the pH of the reaction mixture. The reaction mixture was placed in a refrigerator for about 16 hours, heated to room temperature and filtered to give a white solid. Recrystallization from chloroform gave 400 mg (0.002 mol) of 2,4-dichloro-6-methylsulfonamido-1,3-5-triazine as a white, solid having a melting point of 204 ° to 206 ° C. Elemental analysis of the product gave the following:

Analysis: C ₄ H ₄ Cl ₂ H ₄ O ₂ S

Calculated: C - 19.76, H - 1.66, U - 23.05. Calculated: C - 19.48, H - 1.68, H - 22.44.

This connection is referred to below as connection 143.

Example LXXV:

Preparation of 2,4-dichloro-6- (1'-piperidinoamino) -1,3,5- triazine.

To a solution containing cyanuric chloride (5.0 g, 0.03 mol) in acetone (120 mL) was added dropwise at 0 ° C a solution containing 2,6-lactldin (3.15 milliliters). 0.03 mole) and H-aminopiperidine (2.7 g, 0.03 mole) in acetone (21 ml) while maintaining the temperature below 5 ° C. After stirring for 2 hours, the reaction mixture was warmed to room temperature and stirred for an additional 1 hour. Then the reaction mixture was filtered and the filtrate evaporated. The residue was chromatographed on silica gel to give 620 mg (0.002 mol) of 2,4-dichloro-6- (1'-piperidinoamino) - -, 3,5-triazine as a yellow solid with a melting point of 114 ° C 117 ° C. The elemental analysis of the product gave the following:

Analysis: C ₈ H ₁₁ Cl ₂ M ₅

Calculated: C - 38.72, H - 4.47, H - 28.23. Calculated: C - 37.31, H - 4.51, H - 26.75.

This connection will be referred to as connection 144 below.

Example LXXVI: Preparation of 2,4-bis (dimethylamino) -6-chloro-1,3,5-tria-

z in

To a solution containing cyanuric chloride (92.2 g, 0.5 mol) dissolved in acetone (350 ml) and cooled to a temperature of -30 ° C was added liquid dimethylatnine (90 g, 2.0 mol ), the reaction temperature was below -20 ° C

was held. After the stirring of the reaction mixture was completed, the temperature rose to 5 ° C. Then, the reaction mixture was poured onto crushed ice (2 kg) and the acetone was evaporated by blowing air over the surface while maintaining the mixture at 0 ° C , Upon filtering, the solid (124 g) was recrystallized from pentane and chromatographed on silica gel to give 400 mg (0.002 mol) of 2,4-bis (dimethylamino) -6-chloro-1,3,5-triazine as a yellow, solid To give substance with a melting point of 62 ° - 64 ° C. The elemental analysis of the product gave the following:

Analysis: C ₇ H ₁₂₅

• Calculated: C - 41.69, H - 6.00, H - 34.73. Determined: C - 41.32, H - 5.94, W - 35.18.

This compound will be referred to as compound 145 below.

Example IXXVII: Preparation of 2,4 -dichloro-6-dimethylamino-1,3,5-triazine

Into a solution containing cyanuric chloride (92.2 g, 0.5 mol) dissolved in acetone (380 ml) and cooled to a temperature of -30 ° C was added dropwise 40% aqueous dimethylamine (79 g, 0.7 mol) while keeping the reaction temperature below -20 ° C after the addition was completed, the reaction mixture was stirred at -10 ° C for 30 minutes. The reaction mixture was poured onto crushed ice (2 kg) and the acetone was evaporated by blowing air over the surface while maintaining the temperature of the mixture at 0 ° C. After filtering, the solid was recrystallized from pentane to give ¹ 59.0 g (0.3 mol) of 2,4-dichloro-6-dimethylamino-1,3,5-triazine as a white solid with a melting point of 111 , 5 ° - 115.5 ° C. Elemental analysis of the product indicated the following

Analysis: C ₅ HgCl ₂ H ₄

Calculated: C - 31.11, H - 3.13, W - 29.03. Calculated: C - 31.06, H - 3.06, H - 29.46.

This compound will be referred to as compound I46 below.

Example LXXVIII:

Preparation of 2,4-dichloro-6- (1-morpholinyl) -1,3,5. Triazin

To a solution containing cyanuric chloride (18.4 g, 0.1 mol) in acetone (120 mL) and crushed ice-water (200 mL) was added dropwise morpholine (17.4 g / 0.1 mol) while the reaction temperature kept below 5 ° C. To this mixture was added sodium hydroxide solution (25 ml of a 2H solution) while maintaining the temperature below 5 ° C and the pH below 8.0. The reaction mixture was filtered and the separated solid was recrystallized from ether to give 8.0 g (0.03 mol) of 2,4-dichloro-6- (1-morpholinyl) -1,3,5-triazine as a white Solid substance with a melting point of 154 ° -157 ° C. The blazed analysis of the product gave the following:

Analysis: C ₇ HgCl ₂ H ₄ O

Calculated: C - 35.76, H - 3.43, H - 23.84. Calculated: C - 35.58, H - 3.60, H - 23.83.

This compound is hereinafter referred to as compound 147.

Example LXXIX:

Other compounds were prepared in the same way and in the same way as in the example LXXVIII. The structures and the analytical data for. the compounds I48 and 149 used in the examples below for the reduction of moisture loss of plants are given in Table G below.

Table H

Representative heterocyclic nitrogen-containing compounds; J_

Cl ^ - \

₁₈

Cl

Verb. Substituents elementary analysis

* 18

calculated

determined

Melting point, ⁰ C

⁴¹ » ^{22 4 '32 24} ' ⁰⁴

^{4 '19 23} ' ^{86 82} "

149 I JJ-38,38 3,68 25,58 38,60 3,78 25,46 107 bis

¹ ^ 109

Example LXXX:

Preparation of 2-bis (chloromethyl) amino-4,6-dichloro-1,3,5- triazine

2,4-Dichloro-6-dimethylamino-1,3,5-triazine (18.0 g, 0.09 mol), prepared in Example LXXVII, was heated to a temperature of 130 ° C, introducing chlorine gas and irradiating the solution with ultraviolet light over a period of 5 hours. The resulting residue was chromatographed on silica gel to give 300 mg (0.001 mol) of 2-bis (chloromethyl) amino-4-6-dichloro-1,3,5-triazine as an oil. The elemental analysis of the product gave the following:

Analysis: C ₅ H ₄ Cl ₄ N ₄

Calculated: C - 22.92, H - 1.54, H - 21.39. Calculated: C - 23.10, H - 1.87, K - 21.93. This compound is hereinafter referred to as compound ISO.

Example LXXXI:

Preparation of 2,2'- [1,2-phenylenebis (oxy)] -bis | 4,6-dichlo-

ro-1.3.5-triazine.l · _ ^ __

In the same manner as in the example LIV, cyanuric chloride was reacted with 1,2-dihydroxybenzene in the presence of 2,6-lutidine as an acid acceptor to give 2,2 · - [1,2-phenylenebis (oxy) j-bis [ 4,6-dichloro-1,3,5-triazine] with a melting point of 154 ° -156 ° C. The elemental analysis of the product gave the following:

Analysis: C ₁₂ H ₄ Cl ₄ WgO ₂

Calculated: C - 35.50, H - 0.99, H - 20.70. Calculated: C - 35.60, H - 1.29, N - 20.68.

This connection will be referred to as connection 151 below.

Example LXXXII:

Preparation of 2,4-dibromo-6-isopropoxy-1,3,5-triazine

Part A. Preparation of 2,4-dichloro-6-isopropoxy-1,3,5- triazine

In a stirred solution containing 20.0 g (0.108 mol) of cyanuric chloride in 150 ml of acetone, 12.6 ml (0.12 mol) of 2,6-lutidine was added dropwise at a temperature of -70 ° C. I2-Propanol (8.3 ml, 0.11 mol) was added and the resulting mixture was stirred under a nitrogen atmosphere at room temperature for about 16 hours. The solvent was evaporated in the reaction mixture and the residue was partitioned between ethyl acetate and water. The organic layer was dried (anhydrogenated NBgSO ₄ ), evaporated and the residue was distilled in vacuo to give 2.0 g (0.01 mol) of 2,4-dichloro-6-isopropoxy-1,3,5-triazine in the form an oil with

a boiling point of 152 ° -155 ° C / 42 mm Hg.

Part B. Preparation of 2,4-dibromo-6-isopropoxy-1,3,5-triazine

2,4-Dichloro-6-isopropoxy-1,3,5-triazine prepared in Part A was treated with gaseous hydrogen bromide in a methylene chloride solution at a temperature of 25 ° C following the same procedure as in Example 1 XIX to give 2,4-dibromo-6-isopropoxy-1,3,5-triazine as an unstable, solid S ^ off. The elemental analysis of the product gave the following:

Analysis: CgH ₇ Br ₂ W ₃ O

Calculated: C - 24.24, H - 2.36, N - 14.14, Br - 53.87. Determined: C - 21.14, H - 2.83 ₅ N - 13.89, Br - 53.88.

This connection will be referred to as connection 152 below.

Example LXXXIII:

Preparation of 5- (3 ', 5'-dichlorophenoxy) -3,6-dichloro- 1,2,4-triazine

A. Preparation of 3,5,6-trichloro-i, 2,4-triazine

A mixture containing 6-azaurazil (50 g, 0.44 mol), bromine (49.8 ml, 1 mol) and water (625 ml) was stirred with a magnetic stirrer for 27 hours. The mixture was filtered to give a white powder. Concentration of the product gave another product which was combined with the first. The white solid was recrystallized from water and dried, yielding 53.4 g (0.33 mol) of 5-bromo-6-azaurazil having a melting point of 234-237 ° C.

In 14.4 g (0.08 mol) of S-bromo-δ-azaurazil prepared above were added 299.5 ml (3.4 mol) of phosphorus oxychloride, 30 g (0.14 mol) of phosphorus pentachloride and 30 ml ( 0.19 mol) of Η, Η-diethylaniline. The mixture was stirred magnetically and heated to reflux for two hours, then allowed to stand at room temperature for 24 hours. The excess solvent was removed under reduced pressure and the residue extracted with eight portions of dry ether to 200 ml. The ether was removed and the residue was distilled at 70 ° C / 0.007 mm to yield 8.77 g (0.05 mol) of 3,5,6-trifluoro-1,2,4-triazine having a melting point of 56-58 ° C ,

Part B. Preparation of 5- (3 ', 5'-dichlorophenoxy) -3,6-di- chloro-1,2,4-triazine

Into a solution containing 1.84 g (0.01 mol) of 3,5,6-trichloro-1,2,4-triazine prepared in Part A, in 50 ml of acetone, were added under cooling and Stir 1.07 g (0.01 mol) of 2,6-lutidine and 1.63 g (0.01 mol) of 3,5-dichlorophenol dissolved in 10 ml of acetone at such a rate that the reaction temperature is at 0 ° - '5 ⁰ C remained. The reaction mixture was stirred magnetically for 2 hours and allowed to warm to room temperature. The precipitated 2,6-lutidine hydrochloride was filtered off and washed with 50 ml of acetone. The acetone solution was poured onto about 100 g of ice and the precipitated product was collected and washed with 20 ml of cold, 10% aqueous NaOH and 10 ml of cold water. The solid was dried and crystallized from hexane to give 2.3 g (0.007 mol) of S-O '-' - dichlorophenoxy-1,3-dichloro-1,2,4-triazine as a white solid having a melting point of 130 ° following:

point of 130 ° - 132 ° C.The elemental analysis of the product

C ₉ H ₃ Cl ₄ M ₃ O

Analysis:

Calculated: C - 34.76, H - 0.97, H - 13.51. Determined: C - 34.64, H - 0.93, N - 13.69.

This compound is hereinafter referred to as compound 153.

Example LXXXIX:

Other compounds were prepared in the same manner as in the example LXXXVIII. The structures and analytical data for the compounds 154 Ms 156, which are used in the examples below to reduce the moisture loss of plants, are given in Table I.

Table I

Representative heterocyclic, nitrogen-containing compounds

Verb. substituents N- < ^Y 10 elemental analysis determined enamel IIS D TVV 19 5 9 10 calculated C H point, - ⁰ C CHW

154 4-NO ₂ 0 Cl Cl 37.66 1.40 19.52 37.71 * 1.74 19.63 169-

155 4-CN 0 Cl Cl 44.97 1.51 20.98 44.88 1.67 21.14 149 -

156 2,4-Cl ₂ Cl Cl 34,87 1,30 18,08 34,86 1,42 17,44 175 -

NH

Example XC:

Preparation of 5- (2,4'-di-chlorophenoxy) -3,6-dichloro- 1,2,4-triazine

from hexane. Infrared analysis of the product gave the following: IR (KBr) 3090, 153C ₊ 1505, 1470, 1470, 1400, 1295, 1235, 1205, 1100, 1050, 985, 865, 830, 750 cm ^-1 .

This compound will be referred to as compound 157 hereinafter.

Example XGI:

Other compounds were prepared in the same manner as in Example XC. The structure and analytical data for compounds 158-160, which are used below in the Examples for the reduction of moisture loss of plants, are given in Table J below.

3,5,6-Trichloro-1,2,4-triazine and 2,4-dichlorophenol were reacted in an acetone solution using quinaldine as the acid acceptor in the same manner as in Example III to give 3.0 g (0 , 01 mol) 5- (2 ', 4'τ Dichlorophenoxy) -3,6-dichloro-1,2,4-triazine having a melting point of 9Q ° - 93 ° C after recrystallization

kl

- o

O, Φ

N P

VD O VD ΓΙ I

CTi O ν- VO

I i

 qj- ·. ·.

a * νο

ο ir \ in

-ρ -P -rl

Ε- VD

τ- O

O O

σ \ -P CO ia O I ca Ι ö ti th " Sh O * v • rl O ^ in 3 IA ψ.

φ Β

03 J3 WHERE

Φ Η "Φ

6 ft 6D

WO-P

(O Sh

Table J Representative heterocyclic. nitrogenous compounds

Verb. Substituents

Elemental analysis

Melting point, C

R.

calculated

determined

4-CH ₃ S-O Cl Cl 41 ,

2.45 H, 58 41.80 2.65 14.78

0.92 12.85 33.52 0.95 12.47 160 3-C ₆ H ₅ O-NH Cl Cl 54.07 3.03 16.82 54.32 2.84 16.96

159.. 3,5-Cl ₂ S Cl Cl 33.05 0.92 12.85 33.52 0.95 12.47

- 125

- 117 - 134

(A) 2,6-Lutidine was used as the acid acceptor instead of quinaldine.

Example XCIV:

Other compounds were prepared in the same manner as in Example XCIII. The structures and analytical data for Compound 163 used in the following examples to reduce plant moisture loss are given in Table K below.

CTi VuJ

-J

ul

σ. cn

O CO

todo

(D

Cii

N ¹ O

ro ρ

ö σ ¹

- (B

ρ: Η

co Η

(B (B

Example XCV:

Preparation of tris (4 _< 6-dichloro-1,3 _> 5-triazin-2-yl) amine

In the procedure used in the example of LVl for the preparation of bis (4,6-dichloro-1,3,5-triazin-2-yl) amine, a solid precipitate was isolated by filtration to give tris (4,6-dichloro-1 , 3,5-triazin-2-yl) amine as a by-product having a melting point greater than 360 ° C (decomposition). The elemental analysis of the product gave the following:

Analysis: C ₉ CIgN ₁₀

Calculated / C - 23.45, H - 0.00, N - 30.39. Determined / C - 21.85, H - 1.18, N - 33.65.

This compound will be referred to as compound I64 below.

Example XCVI:

Other compounds were prepared in the same manner as in Example XCIII. The structures and analytical data for the compound used in the examples below for the reduction of plant moisture loss are given in Table L below ,

Table L

Representative hot-cyclic, nitrogenous compounds'

22

Verb. substituents Elemental analysis determined N enamel κ? ^R 22 ^X 8 ^Y 15 calculated C H point, ⁰ C C HN

165 2,4-Cl ₂ 0 Cl 43,59 1,83 10,1? 43.62 1.62 9.97 95 - 97

Example XCVII:

Preparation of 3-chloro-6- (3'-chlorophenoxy) pyridazine

To a solution containing 1.93 g (0.015 mol) of 3-chlorophenol and 1.5 g (0.005 mol) of tetrabutylammonium bromide in 24 mL of 1.25 N aqueous sodium hydroxide was added 2.23 g (0.015 mol) of 3, 6-dichloropyridazine dissolved in 50 ml toluene. The mixture was heated to a temperature of 50 ° C and stirred for 3 hours. The organic layer was separated, washed with dilute MaOH solution and water, dried over MgSO 4, and evaporated. The recovered residue was crystallized from hexane to give 1.55 g (0.006 mol) of 3-chloro-6- (3'-chlorophenoxy) pyridazine as a white solid having a melting point of 85 ° -88 ° C. Elemental analysis of the product indicated following:

Analysis: C ₁₀ HgCl ₂ N ₂ O

Calculated: C - 49.82, H - 2.51, N - 11.62. , average-.C-49.87, H-2.48, N-11, "5.

This compound is hereinafter referred to as compound 166.

Example XCVIir:

Preparation of 4- (4'-Kitrophenaxy) -2,5,6-trichloropyrimidine

In the same manner as in Example I, 2,4,5,6-tetrachloropyrimidine and 4-nitrophenol in acetone solution were reacted using 2,6-lutidine as the acceptor to give 0.8 g (0.002 mol) of 4- (4-nitrophenol). 4'-nitrophenoxy) -2,5,6-trichloropyrimidine having a melting point of 114 ° -116 ° C after vacuum sublimation and two recrystallizations from hexane. The elemental analysis of the product gave the following:

Analysis: C ₁₀ H-Cl ₃ N ₃ O ₃

Calculated: C - 37.47, H - 1.26, N - 13.11, Cl - 33.18. Determined: C - 36.89, H - 1.52, N - 13.00, Cl. - 32.79.

This compound is hereinafter referred to as Compound 167.

Example XCIX:

Other compounds were prepared in the same manner as in Example XCVIII. The structures and analytical data for Compounds 168 and 169 used in the following examples for reducing plant moisture loss are given in Table M below.

, on σ- · VO 03

ro Uj

t Y ¹

Ω Ω

HH ¹

Ω Ω H H "

Ω Ω H Η "

ω σιH H ¹

U) .ρ » U) -ρ- m -5 co -3 ο ο ω ω "cd cd

U) VJl U) VJl -ρ- ο σ \ j ο ο σ. ΟΛ co CO IV) VD sl- ' 108 VD -P- ι I -> VO IVI

to

K) U)

VO ^ K on

-J

_κ co

(D

σ-

03 P er ω rf-Η ·

C +

(B

rf

O (D ¹ O

O Ω

Example C:

Preparation of 2- (2 ', 4'-dichlorophenoxy) pentachlorocyclo

triphophazen

In a solution containing 10.8 g (0.03 mol) of phosphonitrile chloride trimer in 50 ml of acetone at a temperature of -60 ° C was under a nitrogen atmosphere dropwise 3 «! ml (0.03 mol) of 2,6-lutidine in 10 ml of acetone and 5.0 g (0.03 mol) of 2,4-dichlorophenol in 40 ml of acetone. The mixture was allowed to warm to room temperature, stirred for 16 hours, filtered and poured into the filtrate in the läiswasaer. The solid (6.8 g) was taken by filtration, sublimed to remove the unconverted 2,4-dichlorophenol. The pink, semi-solid, which remained in the sublimation blister, was collected to give 0.9 g (0.002 mol) of 2- (2 x 1'-dichlorophenoxy-pentachloro-cyclotriphosphaseh. Magnetic resonance analysis of the product indicated the following: ¹ H-NMR (CDCl ₃ ): i 7.20 - 7.55 particles / mill. (m, aromatic protoaes).

This compound will be referred to as compound I70 below.

Example CI:

Preparation of 2,4-dichloro-6- (2 ', 4'-dichlorophenoxy) hexa- hydro-1,3,5-triazine ,

In a suspension containing 340 mg (0.00 to 1 mole) of 2,4-dichloro-6- (2 ^1, 4'-dichlorophenoxy) -1,3,5-triazine contained in 50 ml of anhydrous ethyl ether, 400 mg (0.01 mol) of sodium borohydride and 5 ml of methanol in portions. The mixture was stirred for 5 minutes and an additional 420 ml (0.01 mol) of sodium borohydride was added. After the mixture was stirred for 15 minutes, 150 ml of ether was added, then the mixture was partitioned between ether and water. The organic layer was dried (Na ₂ SO ₄ ) and evaporated to give 340 mg (0.001 mol) of 2,4-dichloro-6- (2 ·, 4'-dichlorophenoxy) -hydroxy-1,3,5-triazine an unstable, white pesticide; the nuclear magnetic resonance ana-

lysis of the product gave the following:

¹³ C-MR (CD ₃ CN / D ₂ O): δ 118.53, 121.86, 124.87, 125.71, 128.82, 129.5, 130.09, and 130.93 particles / mill.

This compound is hereinafter referred to as compound 171.

Example CII:

Preparation of 2,4-dichloro-6-J4- (4-ethoxyphenylazo) -1-

naphthoxyj-1,3.5-triazine

In the same manner as in Example LIII, 2,4-dichloro-6- [4- (4- ^e 'fcho ^x yphenylazo) -1-naphthoxy _; ] i, 3,5-triazine having a melting point of 173 ° - 177 ° C made. The elemental analysis of the product gave the following:

Analysis: C ₂₁ H ₁₅ Cl ₂ N ₅ O ₂

Calculated: C - 57.29, H - 3.43, W - 15.90.

Determined: C - 57.52, H - 4.08, N - 15.66.

This connection will be referred to as connection 172 below.

Example CIII:

Preparation of 2,4-dichloro-6- (2-methoxyphenoxy) -1,3,5-

triazine ^ ___

In the same manner as in Part B of Example XXII, cyanuric chloride was reacted with 2-methoxyphenol in the presence of 2,6-lutidine as the acid acceptor to give 2,4-dichloro-6- (2-methoxyphenoxy) -1 , 3,5-triazine with a melting point of 93 ° - 94.5 ° C. Slementar analysis of the product showed the following: Analysis: C ₁₀ H ₇ Cl ₂ H ₃ O ₂

Calculated: C - 44, H, H - 2,59, N - 15,44. Calculated: C - 43.99, H-3.00, H - 15.27.

This compound will be referred to as compound 173 below.

Example CIV:

Preparation of 2,4-dichloro-6- (2-benzyloxyphenoxy) -1,3,5- triazine

In the same manner as in Example XXII, Part B, cyanuric chloride was reacted with 2-benzyloxyphenol in the presence of 2,6-lutidine as the acid acceptor to give 2,4-dichloro-6- (2-benzyloxyphenoxy) -1,3 , 5-triazine with a melting point of 92 ° - 94 ° C. The elemental analysis of the product gave the following:

Analysis:

Calculated: C -. 55.19, H - 3.18, N - 12.07. company / C - 55.59, H - 3.19, W - 11.76 '.

This connection will be referred to as compound 174 below.

Example CV:

Preparation of 2,4-dichloro-6 ~ [4- (1-methyl-1- [4-propoxy]

phenyllithyphenoxy-1,3,5-triazine

Part A. Preparation of 4-L, 1-methyl-1- (4-propoxyphenyl) ethyl-1-phenol '

A mixture of bisphenol A (5 x 0 g, 0.02 mol), potassium carbonate (3.04 g, 0.02 mol) and 100 ml of acetophenone was stirred at a temperature of 150 ° C over a period of 2 hours and heated , After cooling to room temperature, 1-iodopropane (3.22 ml, 0.03 mol) was added, then the mixture was stirred at a temperature of 100 ° C over a period of about 16 hours and heated. The reaction mixture was allowed to cool and the solid was removed by filtration. The aeetophenone was removed by distillation under reduced pressure and the residue was purified by Snt chromatography (5 % ethyl acetate / hexane eluant) to give 2.12 g (0.008 mol) of 4- [i-methyl-1- (4-propoxyphenyl) ethyl ] phenol. The nuclear magnetic resonance analysis of the phenol intermediate

gave ¹ H-KMR (CDCl ₃ ): h 0.80-1.91 (ra, 11H7, 3.90 (t, 2H, J = 7 Hz), 5.15 (s, H), 6, 57 - 7,21 (in, SH) particles per mill.

Part B. Preparation of 2,4-dichloro-6- [4- (1-methyl-1- [4- propoxyphenyl-ethyl) -phenoxy-1,3,5-triazine

In the same manner as in Part B of Example XXII, cyanuric chloride was treated with 4-methyl-1- (4-propoxyphenyl) ethylenephenol prepared in Example CV, Part A above, in the presence of 2 , 6-lutidine as the acid acceptor gave 2j4-dichloro-6- [4- (1-methyl-1- [4-propoxyphenyl] -ethyl)] phenoxy-1,3,5-triazine as an oil. The elemental analysis of the product gave the following:

Analysis: C ₂₁ H ₂₁ Cl ₂ N ₃ O ₂

Calculated: C - 60.30, H - 5.06, N - 10.04. Determined: C - 59.62, H - 5.06, N - 10.84.

This connection will be referred to as connection 175 below.

Example CVI:

Preparation of 2,4-dioxoro-6- [4- (1-methyl-1-L4-methoxy)

phenyl ·] ethyl)] phenoxy-1,3,5-triazine

Part A. Preparation of 4- [i-methyl-1- (4-methoxyphenyl) -ethyl phenol -

In the same manner as in Example CV, Part A, bisphenol A was reacted with methyl iodide in acetone solution and in the presence of potassium carbonate as the acid acceptor to add 4- [1-methyl-1- (4-methoxyphenyl) ethyl] phenol result. Nuclear Magnetic Resonance Analysis of the intermediate phenol gave the following: ¹ H-NMR (CDCl ₃ ): J 1.63 (s, 6H), 3.77 (s, 3H7, 5.62 (s, H), 6.55-7, 27 (m, 8H) particles / Mill.

Part B. Preparation of 2,4-dichloro-6- [4- (1-methyl) -1- [4- methoxyphenyl-ethyl) -phenoxy-1,3,5-triazine

In the same manner as in Example XXII, Part B, cyanuric chloride with 4 μg of iMethyl 1- (4-methoxyphenyl) ethyl] phenol prepared in Part A above was obtained by the hand of 2,6-lutidine as the acid acceptor to give 2,4-dichloro-6- [4- (1-methyl-1- [4-methoxyphenyl] -ethyl) -phenoxy-1,3,5-triazine having a melting point of 108 ° -111 ° C. Elemental analysis of the product gave the following: Analysis: C ^ H ^ Clp-, 02

Calculated: C - 58.47, H - 4.39, H - 10.77. Calculated: C - 58.35, H - 4.40, Ii - 10.76.

This compound is hereinafter referred to as Compound 176.

Example CVII:

Preparation of 2,4-dichloro-6- [4-O-methyl-1- [4-benzyloxy-

phenyi ethyl)! pehnoxy-1,3,5-triazine

Part A. Preparation of 4- [i-methyl-1- (4-benzyloxyphenyld ethyl ] phenol

Bisphenol A was reacted with benzyl chloride in acetone solution in Vorhandenseion of potassium carbonate as acid acceptor in the same manner as in part A of Example ¹ CV to give 4- [1-methyl-1- (4-benzyloxyphenyl) ethyl] phenol. The nuclear magnetic resonance analysis of the intermediate phenol gave the following: 'H-HMR (CDCl ₃ ): 1.60 (s, 6H), 4.57 Is, H, 5.00 (s, 2H), 6.56-7.48 (m, 8H) Particles / Mill.

Part B. Preparation of 2,4-Di'chloro-6- [4- (1-methyl-1-J4-benzyloxyphenyl] ethyl)! phenoxy-1,3,5-triazine

In the same manner as in Part B of Mspiel XXII, cyanuric chloride was treated with 4- [i-methyl-1- (4-benzyloxyphenyl) ethyl] phenol prepared in Part A above, in the presence of 2.6 -Lutidine reacted as an acid acceptor to give 2,4-dichloro-6-4- (1-methyl-1-4-benzyloxyphenyl ethyl) phenoxy-1,3,5-triazine, mp 117.5

to 119 of:

C. Elemental analysis of the product showed the following analysis: C ₂₅ H ₂₁ Cl ₂ M ₃ O ₂

Calculated: C - 64.39, H - 4.54, K - 5.01. Determined: C - 64.09, H -. 4,59, K - 8,87.

This compound is hereinafter referred to as compound 177.

Example CVIII:

Preparation of 2,4-dichloro-6- (2-n-butyloxyphenoxy) -1,3,5-

triazine

Part A. Preparation of 2- (n-butyloxy) phenol

In the same manner as in Part A of Example XXII, catechol was reacted with 1-bromobutane in the presence of sodium hydroxide as the acid acceptor to give 2- (n-butyloxy) phenol. Nuclear Magnetic Resonance Analysis of the intermediate phenol gave the following: ¹ H-KMR (CDCL,): 0.73 - 1.95 (m, 7H), 3.63 - 4.08 (t, 2H), 6.02-7, 32 (m, 4H) parts / mill.

Part B. Preparation of 2,4-dichloro-6- (2-n-butyloxy-phenoxy ) -1,315-triazine

In the same manner as in Part B of Example XXII, cyanuric chloride was reacted with the 2- (n-butyloxy) phenol prepared in Part A above in the presence of 2,6-lutidine as the acid acceptor to give 2,4-dichloro-6 - (2-n-butyl oxyphenoxy) -1,3,5-triazine in the form of an oil. The elemental analysis of the product gave the following: Analysis: C ₁₃ H ₁₃ Cl ₂ H ₃ O ₂

Calculated: C - 49.70, H - 4.17, N - 13.37. Determined: C - 50.82, H - 4.69, M - 12.98.

This connection is hereinafter referred to as connection 178 '.

example QJX:

Other compounds were prepared in the same manner as in Example CVIII. The structures and analytical data for compounds 179 to I84 used in the examples below for the reduction in moisture loss of plants are given in Table N below.

Table N Representative heterocyclic, nitrogen-containing compounds

Verb 5u.bstituen.ten

R.

55

R =

c ι

Elemental analysis

calculated

determined

HN

Melting point, C

179 2-130 4-181 4-

In-C ₃ H ₇ O

53.11 4.16 12.39 51.94 4.53 12.80 'oil

57.46 4.02 11.17 57.44 4.05 11.01 164.5 - 165.5

61.88 5.65 9.41 62.01 5.81 9.17 141.5 -n142.5

Verb. Substituents

Elemental analysis

calculated

determined

HN

183 4 184

Melting point, C

182 4- | cH ₃ 0- (oVcH ₂ - J 56,37 3,61 11,60 56,61 3,88 11,87 136,0 - 137,0 - £ -C ₃ H ₇ O- / q \ -CH ₂ - [58,55 4,38 10,75 58,08 4,50 10,74 91,5 - 93,0. " ^{63 '03 3} ' ^{91 9 '59} 62,95 4,20 9,27 113.5 to 115.0

Apples CX:

Preparation of 2-4-dichloro-6- | 4- (4-benzyloxyphenylthio) J -

phenoxy-1,3,5-triazine ;

Part A. Preparation of 4-I (4-benzyloxyphenylthio) -phenol

A mixture of 5.0 g (0.02 mol) of 4,4'-thiobisphenol, 3.79 g (0.03 mol) of potassium carbonate and 75 ml of acetone was heated at reflux over a period of 2 hours. After cooling to room temperature, 4.35 g (0.03 mol) of benzyl chloride were added dropwise to the reaction mixture, which was heated at reflux for 16 hours. Then, the reaction mixture was cooled to room temperature and filtered through Celite to remove the solid substances. The Piltrat was concentrated in vacu o and the residue purified by flash to give 2.82 g (0.01 mol) of 4-j (4-Benzyloxyphenylthio)] phenol. Nuclear magnetic resonance analysis of the intermediate phenol gave the following: ¹ H-HMR (CDCL.,): J 4.98 (s, H), 5.08 (s, 2H), 6.65-7.50 (m, 13H) particles / Mill.

Part B. Preparation of 2,4-dichloro-6- [4- (4-benzyloxyphenylthio ) -1-phenoxy-1,3,5-triazine ;

In the same manner as in Part B of Example XXII, cyanuric chloride was reacted with 4- | J [4-benzyloxyphenylthio] J phenol prepared in Part A above in the presence of 2,6-lutidine as the acid acceptor to give 2 , 4-Sichloro-6-4- (4-benzyloxyphenylthio). phenoxy-1,3,5-triazine having a melting point of 119 ° -120 ° C. Elemental analysis of the product indicated the following:

Example CXI:

Other compounds were prepared in the same manner as in Example CX. The structures and analytical data for compounds 186 and 187, which are used in the following Examples for the reduction of moisture loss of plants, are given in Table 0 below.

Table ο '

Representative heterocyclic, nitrogen-containing compounds

Verb. Substituents elementary analysis

56

187 4-y

calculated

determined

Melting point

HN

H W

186 4- [n-C3H ₇ O-Zo) -SJ 77.0 -

52.95 3.70 10.29 52.89 3.72 10.56 80.0

S-J 107.0 -

50.54 2.92 11.05 50.33 3.17 10.72 109.0

Analysis: C ₂₂ H ₁₅ Cl ₂ N ₃ O ₂ S

Calculated: C - 57.90, H - 3.31, W - 9.20. Calculated: C - 58.49, H - 3.60, N - 8.94.

This connection will be referred to as connection 185 below.

Example CXII:

Preparation of 2-chloro-4-methyl-6-L4- (1-methyl-1-r4-methoxy)

oxyphenyl-ethyl) - phenoxy-ri, 3,5-triazine

To a stirred solution of 0.72 g (0.002 mol) of 2,4-dichloro-6- [4- (1-methyl-1- (4-methoxyphenyl-ethyl) phenoxy-1,3,5-triazine prepared in the example CVI in 50 ml of tetrahydrofuran was slowly added 2.04 ml (0.006 mol of 2.7M methylmagnesium bromide in ethyl ether solution while the mixture was cooled in an ice-bath, then the mixture was allowed to warm to room temperature and then stirred for a period of 15 The solvents were removed by vacuum evaporation, the residue was purified by flash chromatography (3 % ethyl acetate in a hexane eluant) to give 0.43 g (0.001 mol) of 2-chloro-4-methyl-6- £ 4- (1-methyl). 1- [V-methoxyphenyl] ethyl)] phenoxy-1,3,5-triazine in the form of pale yellow crystals with a melting point of 65.0 ° -6.7 ° C. The elemental analysis of the product showed the following:

Analysis: Cp (Jl

Calculated: C - 64.95 ^ H - 5.45 ·, H - 11.36.

Calculated: C - 64.58, H - 5.57, N - 11.25.

This compound will be referred to as compound 188 below.

Example CXIII:

Preparation of 2,4-dichloro-6- (4-chlorophenylsulfonyl) phenoxy-1,3,5-triazine

Part A. Preparation of 4-chlorophenyl-4'-hydroxyphenylsulfone

To a stirred solution of 28.7 g (0.01 mole) bis (4-chlorophenyl) sulfone in 100 ml dimethylsulfoxide was added a solution of 13.1. Over a period of 10 minutes while heating the reaction mixture to a temperature of -40 ° C g (0.23 mol) of potassium hydroxide in 15 ml of water. Then, the reaction mixture was heated at a temperature of 105 ° C over a period of 5 hours, cooled to room temperature, and poured into 300 ml of water. A white, milky precipitate was filtered out and, as a result, the filtrate was made acidic with HCl. The aqueous solution was extracted with ether (3 × 100 ml) and the combined ether layers were washed with 10% aqueous K.KaOH (2 × 50 ml). The combined basic layers were made with HCl and extracted with ether (2 × 50 ml). Evaporation of the ether gave 19.21 g (0.08 mol) of 4-chlorophenyl-4'-hydroxyphenylsulfone having a melting point of 143.0-146.0 ° C.

Part B. Preparation of 2,4-dichloro-6-J4- (4-chlorophenylsulfonyl ) -1-phenoxy-1,3,5-triazine

In the same manner as in Example XXII, Part B, cyanuric chloride was reacted with the 4'-chlorophenyl-4'-hydroxyphenylaulphon prepared in Part A above in the presence of 2,6-lutidine as the acid acceptor to give 2.4 Dichlo- XO-G- J4- (4-chlorophenylsulphonyl) -1-phenoxy-1,3,5-triazine having a melting point of 167 ° C. The elemental analysis of the product showed the following:

Analysis: C ₁ CHgCl ₃ Ii ₃ O ₃ S

Calculated: C-43.24, H-1.93, N-10.08. Determined: C - 43.16, H - 2.01, W - 10.01.

This compound is hereinafter referred to as compound 189.

Example CXIV:

Preparation of bis-4- (4,6-dichloro-1,3,5-triazin-2-yloxy) -

pehnyl sulfide on.

In the same manner as in Part B of Example XXII, cyanuric chloride was reacted with bis (4-hydroxyphenyl) sulfone in the presence of 2,6-lutidine as the acid acceptor to give | 4- (4,6-dichloro-1,3, 5-triazin-2-yloxy) phenylsulfone having a melting point of 230 ° -235 ° C. The elemental analysis of the product gave the following:

Analysis:. C ₁₈ HgCl ₄ N ₆ O ₄

Calculated: C - 39.58, H - 1.48, M - 15.39. Determined: C - 41.30, H - 1.73, N - 14.61.

This connection is hereinafter referred to as connection 190.

Example CXV:

Preparation of (4,6-dichloro-i, 3,5-triazine-2-yl) - {4,6-di-

methoxy-1,3,5-triazin-2-yl) ether ; · _

Part A. Preparation of 2,4,6-trimethoxy-1,3,5-triazine

To a stirred solution of 12.0 g (0.30 mol) of sodium hydroxide in 100 ml of methanol was slowly added over a period of one hour 18.5 g (0.10 mol) of cyanuric chloride in small portions, while the reaction temperature at 25 ° - 30 ⁰ C was maintained: .. After this period, the reaction mixture was stirred at room temperature for two hours. The mixture was filtered and methanol evaporated from the filtrate under reduced pressure. The residue was vacuum dried and crystallized from water to give 4.3 S (0.025 mole) of 2,4,6-trimethoxy-1,3,5-triazine, mp 122 ° -129 ° C. Analysis by in-phase high pressure liquid chromatography gave the product a purity of about 75 %.

Part B. Preparation of sodium 4,6-dimethoxy-1,3,5-triazine- 2-olate

To a stirred solution of 1.86 g (0.05 mol) of sodium hydroxide in -25 ml of methanol was added 4.0 g (0.02 mol) of the 2,4,6-trimethoxy-1,3,3,3-trifluoromethane prepared in Part A above, 5-triazine which was heated under reflux for a period of one hour. The solution was allowed to cool and a white gum was collected and dried to yield 3.95 g (0.02 mole) of sodium 4,6-dimethoxy-1,3,5-triazine-2-olate.

Part C. Preparation of (4,6-dichloro-1,3,5-triazin-2-yl) - (4,6 -dimethoxy-1, 3,5-triazin-2-yl) ether

The sodium 4,6-dimethoxy-1,3,5-triazin-2-olate (1.5 g, 0.01 mol) prepared in Part B above was brought to 25 ml acetonitrile for suession dissolution and the mixture was brought to a temperature from 5 - 10 C in an ice bath cooled. Then, a solution of 1.54 g (0.01 mol) of cyanuric chloride in 25 ml of acetonitrile was added dropwise with stirring while keeping the temperature below 10 ° C. The reaction mixture was stirred in an ice bath and allowed to warm slowly to room temperature. After the reaction mixture was stirred for 16 hours, it was filtered and the solvent removed by evaporation. A white, solid residue was purified by flash chromatography (30 % ethyl acetate in hexane) to give 1.34 g (0.004 mol) of (4,6-dichloro-1,3,5-triazin-2-yl) - (4, 6-dimethoxy-1,3,5-triazin-2-yl) ether having a melting point of 158.5 ° -160 ° C. The elemental analysis of the product gave the following:

Analysis: CgH ₆ Cl ₂ N ₆ O,

Calculated: C - 31.50, H - 1.98, N - 27.55. Determined: C - 31.74, H - 2.07, N - 27.47.

This compound will be referred to as compound 19'1 below.

Example CXVI: Preparation of 2,2'-thiobis (4.6-dichloro-1,3,5-triazine)

To a stirred solution of 10.0 g (0.05 mol) of cyanuric chloride in 100 ml of acetone was added a solution of 3.26 g (0.01 mol) of sodium sulfide nonahydrate in 30 ml of water over a period of 30 minutes while the temperature of the Reaction mixture was kept by cooling from the outside at 0 ° - 5 ° C. The reaction mixture was stirred at a temperature of 0 ° -5 ° C over a period of 15 minutes, and 150 ml of Biswaaser was added. It formed a white precipitate, which immediately filtered out and

was dried. Neat-reacted cyanuric chloride was removed from the crude product by vacuum sublimation and the residual solid recrystallized from hexane / methylene chloride to give 2,2'-thiobis (4,6-diohloro-1,3,5-t: riazine) as a white, one-melting pesticide of I4O ⁰ bia 145 ° C. analysis of the product by high pressure liquid chromatography indicated a purity of 75% "resulted infrared analysis of the product, as follows: IR (CHCl _3): 1500, 1240, 850 om ~. Mass spectrometric analysis of the product showed m / e 330 (calculated molecular weight 329> 98).

This connection will be referred to as connection 192 below.

Example CXViT:

Preparation of (4-chloro-6-methoxy-1,3,5-triazin-2-yl)

(4.6-dimethoxy-I.3.5-triazin-2-yl) ether

Part A. Preparation of 2 ', 4-dichloro-6-methoxy-1,3,5- triazine

A mixture of 20.2 g (0.11 mol) cyanuric chloride, 18.4 g (0.22 mol) of sodium bicarbonate, 100 ml of methanol and 125 ml of water was stirred at room temperature for 40 minutes and then diluted with 100 ml of water, the resulting solid was filtered out. The white solid was vacuum dried to yield 13.4 g (0.08 mol) of 2,4-dichloro-6-methoxy-1,3,5-triazine having a melting point of 88 ° -90 ° C.

T'eil B. Preparation of ^ -Chloro-ö-methoxy »·! 3,5-triazin- 2-yl) (4,6-dimethoxy-1-methyl-S-triazine) ether

To a stirred suspension of 2.91 g (0.02 mole) of the sodium 4,6-dimethoxy-1,3,5-triazin-2-olate prepared in Part B of Example CXV in 50 ml of acetonitrile was added dropwise a solution of 2.93 g (0.02 ml of 2,4-dichloro-6-methoxy-1,3,5-triazine prepared in Part A above were added.) The reaction mixture was stirred at reflux for a period of 48 hours and heated and then after the addition of 1.17 g (0.003 mole) of dibenzo-18-crown-6 is heated by a second period of 48 hours under reflux. the mixture was allowed to cool, it was diluted with 75 ml methylene chloride and then filtered "after evaporation the '· solvent, the residue was purified by flash (20%> ethyl acetate in a Hexaneluierungsmittel) to give 1.60 g (0.005 mol) of (4-chloro-6-methoxy-1,3,5-triazin-2-yl) (4,6-dimethoxy-1,3,5-triazin-2-yl) ether having a melting point of 126.5 ° -128 ° C. Elemental analysis of the product indicated the following:

C ₉ H ₉ ClU ₆ O ₄

Analysis:

Calculated: c "-'35.95 ', H-3.01, H-27.95, C-35.92, H-3.12, H-28.08.

This compound will be referred to as compound 193 below.

Example CXVIII:

Preparation of 2-chloro-4,6-dimethoxy-1,3,5-triazine

A mixture of 18.5 g (0.10 mol) of cyanuric chloride, 16.8 g (0.20 mol) of matrium bicarbonate, 57 ml of methanol and 5 ml of water was vigorously stirred and when the temperature rose to about 40 ° C. " After a period of 20 minutes, the formation of carbon dioxide had slowed down and the reaction mixture was refluxed over a period of 30 minutes. The mixture was cooled and diluted with water resulting in the settling of a carbon dioxide The solid was collected, washed with water, vacuum dried and the crude product crystallized from cyclohexane to give 10.0 g (0.06 mole 2-chloro-4,6-dimethoxy-1,3,5-triazine in the form of a white, crystalline pesticide having a melting point of 69 ° -71 ° C. The elemental analysis of the product gave the following:

Analysis: OA

Calculated: C - 34.20, H - 3.44, N - 23.93. Determined: C - 34, H, H - 3.60, N - 23.96.

This compound is hereinafter referred to as compound 194.

Example CXIX:

Preparation of 6- (2,4-dichlorophenylazo) -2,4-dichloro

1,3,5-triazine

A slow stream of chlorine gas was passed over a ten minute period through a Zweiphaserlgemisch consisting of a solution of 2.6 g (0.008 mol) of N- (2,4-dichlorophenyl) -N ^l - (4,6-dichloro- 1,3,5-triazin-2-yl) hydrazine in 75 ml CHCl ₃ and from a solution of 1.34 g (0.02 mol) HaHCO ₃ in 40 ml water. Nitrogen was then bubbled through the mixture to remove the excess chlorine and the organic layer was separated, washed with water and anhydrous MgSO 4. dried and yielded 2.4 g of a dark red solid. This was combined with 980 mg of product recovered from a previous, identical reaction, except that 1.0 g '(0.003 mol) of H- (2,4-dichlorophenyl) -1- (4,6-dichloro) 1,3,5-triazin-2-yl) hydrazine had been used. The combined products were subjected to flash silica gel relaxation chromatography using a 9: 1 v / v hexane-ethyl acetate eluent. subjected and gave a red solid. This crude product was recrystallized from hexane to give a material which was sublimed and 0.91 g (0.003 mol) of 6- (2,4-dichlorophenylazo) -2,4-dichloro-1,3,5-triazine as a red, solid substance with a melting point of 119 ° - 123 ° C resulted. The elemental analysis of the product gave the following:

Analysis: CgH ₃ Cl-H ₅

Calculated: C - 33.47, H - 0.94, N - 21.68. Calculated: C - 32.95, H - 0.97, M - 21.14.

This compound is hereinafter referred to as compound 195.

Example CJGi:

Preparation of 2- (4-methoxyphenyl) -4,6-dichloro-1,3,5-tria-

In the same manner as in Example XL, cyanuric chloride was reacted with the Grignard reagent of 4-bromoanisole to give 2- (4-methoxyphenyl) -4,6-dichloro-1,3,5-triazine having a melting point of 136 , 5 - 138.5 C. Elemental analysis of the product showed the following:

C ₁₀ H ₇ Cl ₂ H ₃ O

Analysis:

Law: C - 4'6,9O ^ H - 2,76, N * · 16,41. Calculated: C - 46.76, H - 2.78, N - 16.29.

This compound is hereinafter referred to as compound 196.

Example CXXI:

Other compounds were made in the same way as in Example CXX. The structures and analytical data for compounds 197 to 199v, which are used in the following Examples for the reduction of moisture loss of plants, are given in Table P below.

Table P

Preparation of representative heterocyclic nitrogen-containing compounds

Verb substituents elementaryanalysc

57

calculated

determined

Melting point ¹ C

point, o

H M.-C

H H

197 4-CH ₃ 50.03 2.94 17.50 50.58 3.17 17.36 148.0

to 150.5

198 4-Cl 41.50 1.55 16.13 41.13 1.83 16.06 150.0

up to 151.0

199 2,4-Cl ₂ 36,65 1,03 14,25 36,27 1,39 14,19 143,0

up to 145.0

Example CXXII:

Preparation of 2- [(2-phenoxy) ethoxyj-4,6-d ± chloro-1,3,5-

triazine.

In the same manner as in Example XXXII, phenoxyethanol was reacted with cyanuric chloride in the presence of 2,6-lutidine as the acid acceptor to give 2 - [(2-phenoxy) ethoxy-3,4,6-dichloro-1,3,5-triazine with a melting point of 81 ° - 83 ° C. The elemental analysis of the product gave the following:

Analysis: C ₁₁ H ₉ Cl ₂ N ₃ O ₂

Calculated: C - 46.17, H -'3.17, H - 14.69.

Calculated: C - 46.41, H - 3.44, N - 14.68.

This connection is hereinafter referred to as connection 200.

Example CXXIII:

Preparation of 2- [2- (2,4-dichlorophenoxy) ethoxy] -4,6-di-

chloro-1 _t 3,5-triazine

Part A. Preparation of 2- (2,4-dichlorophenoxy) ethanol

To a solution of 2.44 g (0.06 mol) of WaOH in 20 ml of water was added. the 10.0 g (0.06 mol) of 2,4-dichlorophenol added in portions. Then, a portion of 2-bromoethanol was added to 4.8 ml (0.07 mol) and the mixture heated at a temperature of 60 ° C over a period of about 16 hours. Upon cooling, the reaction mixture was extracted with dichloromethane and the combined organic extracts were then washed with a 1N NaOH solution and water and dried over MgSO 4. dried. Concentration under reduced pressure gave 8.02 g (0.04 mol) of 2- (2,4-dichlorophenoxy) ethanol. The nuclear magnetic resonance analysis of the intermediate phenol gave the following: ¹ H-HMR (CDCl ₃ ): } 2.73 (m, H), 3.7-4.4. (M, 4H), 6.97 (d, H, J = 8 Hz), 7.33 (dd, H, J = 3.8 Hz), 7.47 (d, H, J = 3 Hz) Particles / Mill.

Part B. Preparation of 2- [2- (2,4-dichlorophenoxy) ethoxy] -4,6 -dichloro-1,3,5-triazine

In the same manner as in Example XXXII, cyanuric chloride was reacted with the 2- (2,4-dichlorophenoxy) ethanol prepared in Part A above in the presence of 2,6-lutidine as the acid acceptor to give 2- ^ 2- (2, 4-dichlorophenoxy) ethoxy] -4,6-dichloro-1,3,5-triazine having a melting point of 103 ° -104.5 ° C. Elemental analysis of the product gave the following:

C ₁₁ H ₇ Cl ₄ N ₃ O ₂

Analysis:

Calculated: C - 37.21, H - 1.99, N - 11.84. Calculated: C - 37.06, H - 2.19, H _ 11.73.

This connection is hereinafter referred to as connection 201.

Example CXXIV:

Preparation of 2- (2,4-dichlorobenzyloxy) ethoxy-4,6-di-

chloro-1.3,5-triazine

Part A. Preparation; of 2- (2,4-dichlorobenzyloxy) ethanol To a slurry of 125 g of neutral alumina in 125 ml

Ether was added to 5.0 g (0.03 mol) of 2,4-dichloro-benzylalcohol and 62.5 ml (0.12 mol of a 2M solution of ethylene oxide in ether.) This mixture was added over a period of about 16 hours Stirred, poured into 500 ml of methanol and allowed to stand for 6 hours, the alumina was filtered off, washed with methanol and the filter was concentrated under reduced pressure to give 9.26 g of the crude product as a clear liquid Product which had been prepared in a previous, identical reaction but using 2.0 g (0.01 mol) of 2,4-dichlorobenzyl alcohol. The combined products were subjected to flash chromatography using hexane-ethyl acetate. 1: 1 v / v) as the eluting agent, and 1.3 g (0.006 mol) of 2- (2,4-dichlorobenzyloxy) ethanol in I ¹ DBm of a colorless liquid were obtained s: 'H-WMR (CDCl ₃ ): b 2.47 (br s, H), 3.5-4.0 (m, 4H), 4.60 (s, 2H), 7.1-7, 6 (m, 3H) particles / Mill.

Part B. Preparation of 2- ( 2m4-dichlorobenzyloxy) ethoxy] -4,6-dichloro-1,3,5 -triazine

In the same manner as in Example XXXII, cyanuric chloride was prepared with the 2- (2,4-dichlorobenzyloxy) ethanol prepared in Part A above in the presence of 2,6-lutidine as the acid acceptor, giving 2- [(2,4- Dichlorobenzyloxy) ethoxy- "J-4,6-dichloro-1,3,5-triazine in the form of a colorless oil." Elemental analysis of the product indicated the following:

Analysis: C ₁₂ H ₉ Cl ₄ K ₃ O ₂ .

Calculated: C - 39.05, H - 2.46, N - 11.39. Determined: C-39.82, H-2.55, N-11.32.

This connection is hereinafter referred to as connection 202.

Example CXXV:

Preparation of 2- (2- [2- (2-4-dichlorophenoxy) ethoxy] ethoxy) -

4.6-dichloro-1,3,5-triazine

Part A. Preparation of 2- [2- (2,4-dichlorophenoxy) ethoxy] ethanol

In the same manner as in Part A of Example CXXIII, 2,4-dichlorophenol was reacted with 2- (2-chloroethoxy) ethanol in the presence of sodium hydroxide as the acid acceptor to give 2- [2- (2,4-dichlorophenoxy) ethoxy] ^ ethanol in the form of a colorless liquid. The nuclear magnetic resonance of this intermediate gave the following: 'H-HMR (CDCl ₃ ): <2.83 (br s, H), 3, -5-4.0 (m, 6H), 4.1 to 4 , 4 (m, 2H), 6.83 (d, H, J = 2 Hz), 7.20 (dd, H, J = 2.8 Hz), 7.37 (d, H, J = 2 Hz ) Partcheiji / Iill.

Part B. Preparation of 2- (2- [2- (2,4-dichlorophenoxy) ethoxy ] ethoxy) -4,6-dichloro-1,3,5-tria2in

In the same manner as in Example XXXII, cyanuric chloride was reacted with the 2- [2- (2,4-dichlorophenoxy) ethoxylethanol prepared in Part A above in the presence of 2,6-lutidine as the acid acceptor to give 2- (2- Γ 2- (2,4-dichlorophenoxy) ethoxyl ethoxy) -4,6-dichloro-1,3, S-tria-

zin with a melting point of 59.5 ° - 61.5 ° C. The elemental analysis of the product gave the following:

Analysis: C ₁₃ H ₁₁ Cl ₄ N ₃ O ₃

Calculated: C - 39.12; H - 2.78;,: N - 10.53. Calculated: C - 38.65, H - 2.76, N - 10.71.

This connection is hereinafter referred to as connection 203.

Example CXXVI:

Preparation of Z- [4- (2,4-dichlorophenyl) butoxy-4,6-dichloro-1, 3,5-triazine

Part A. Preparation of 2- (2,4-dichlorophenyl) othylbromide

A mixture of 30.1 g (0.16 mol) of the 2,4-dichlorophenethyl alcohol prepared in Part A of Example XLVIII and 140 ml of 48% aqueous HBr was heated at reflux over a period of 5 hours. On cooling, the reaction mixture was partitioned between ether and water, then the ethereal phase was extracted with saturated aqueous NaHCO 3, over MgSO 4. dried and concentrated under reduced pressure, giving a brown liquid. Kugelrohr distillation afforded 29.7 g (0.12 mol) of 2- (2,4-dichlorophenyl) ethyl bromide as a colorless liquid with a boiling point of 70 ° C at 0.025 mm Hg. Magnetic resonance analysis of this intermediate gave the following ¹ H-NME (CDCl,): jf 3.0 to 3.8 (m, 4H), 7.0 to 7.4 (rn, 3H) particles / Mill

Part B. Preparation of 4- (2,4-dichlorophenyl) butan-1-ol

To 0.96 g (0.04 mol) of magnesium turnings in 20 ml of anhydride-soluble tetrahydrofuran was added dropwise a solution of 2- (2,4-dichlorophenyl) ethyl bromide prepared in Part A above in 30 ml of tetrahydrofuran. After the magnesium was consumed, the yellow solution of Grignard reagent was added dropwise to a cold (-30 ° C) mixture of 1.9 g (0.01 mol) of cuprous iodide in 30 ml of tetrahydrofuran. This mixture was stirred for a period of 5 minutes, then 35 ml of tetrahydrofuran was added. This mixture was stirred for an additional 5 minutes and 35 ml (0.07 mol) of a 2M solution of ethylene oxide was added dropwise. The reaction mixture was stirred for two hours at a temperature of 0 ° C and then for one hour at room temperature, then quenched with 50 ml of water. The volume was reduced in vacuo and the residue extracted with ether. The ethereal layer was dried (MgSO 4) and concentrated under reduced pressure to give a liquid which was chromatographed on silica gel, yielding 2.37 g (0.01 mol) of 4- (2,4-bichlorophenyl) butan-1-ol in the form of a pale yellow liquid. The nuclear magnetic resonance analysis of this intermediate gave the following: ¹ H-NMR (CDCl ₃ ): i 1.43-1.83 (m, 4H), 2.53-2.90 (m, 3H), 3.50-3, 77 (m, 2H7, 7.07 (m, 2H), 7.33 (m, H) particles / Mill.

Part C. Preparation of 2-S.4- (2,4-dichlorophenyl) butoxyj 4.6-dichloro- 1,3,5 -t

In the same manner as in Example XXXII, cyanuric chloride was reacted with the 4- (2,4-dichlorophenyl) butan-1-ol prepared in Part B above in the presence of 2,6-lutidine as an acid acceptor to give 2- {4 - (2,4-D, dichlorophenyl) butoxy. -J-4,6-dichloro-1,3,5-triazine in the form of a pale yellow oil.

Analysis: C ₁₃ H ₁₁ Cl ₄ N ₃ O

Calculated: C - 42.53, H - 3.02, N - 11.45. Sirents: C - 43.30, H - 3.08, N - 10.76.

This connection is hereinafter referred to as connection 204.

Example CXXVII:

Preparation of 2,4-dichloro-6- (2,4-dichloro-3,5-dimethyl)

phenoxy) -1.3.5-triaain

In the same manner as in Example I, cyanuric chloride was reacted with 2,4-dichloro-3,5-dimethylphenol in the presence of 2,6-lutidine as the acid acceptor, giving 2,4-dichloro-6- (2,4- dichloro-3,5-dimethylphenox _y ) -1,3,5-triazine with a melting point of 118 ° -120 ° C. The elemental analysis of the product gave the following:

Analysis: C ₁₁ H ₇ Cl ₄ N ₃ O

Calculated: C - 38.97, H - 2.08, N - 12.39. Calculated: C - 39.18, H - 2.25, N - 12.47.

This connection is hereinafter referred to as connection 205.

Example CXXVHI:

Other compounds were prepared in the same manner as in Example CXXVII. The structures and analytical data for compounds 206-210, which are used in the following examples for the reduction of plant moisture loss, are given in Table Q below

 Table Q

Representative Heterocyclic , Nitrogenous Compounds -

Verb. Substituents elementary analysis

58

calculated

determined

Melting trace ⁰ C

Points

or

HW

206 2,3,4,5,6-F ₅ 32,56 - 12,66 32,72 - 12,46 88 bis

207 3-CH ₁

38.73 1.30 13.55 39.12 13.36 13.29 88 bis

90 IR (KBr) 1490, 1400, 1290, 1245, 98 bis

1190, 1140, 1000, 960, 840, 795 101 -1

209 2-Cl-4-N0 ₂ 33,62 0,94 17,43 33,88 1,08 17,55 131 bis «

210 4-H ₉ NC- 42,13 2,12 19,65 42,71 2,67 19,30 189 bis

0 191

Example CXXIX:

Preparation of acetone-0- (4,6-dichloro-1,3,5-triazin-2-yl) -

ox in ;

In the same manner and as in Example XXXVI, cyanuric chloride was reacted with acetone oxime in the presence of sodium bicarbonate as the acid acceptor to give 0- (4,6-dichloro-1,3,5-triazin-2-yl) oxime having a melting point from 60 ° - 62 ° C. The elemental analysis of the product gave the following:

Analysis: CgHgCl ₂ NO

Calculated: 'C - 32.60, H - 2.74, N - 25.35. Determined: C - 32.24, H - 2.90, N - 25.28.

This connection is hereinafter referred to as connection 211.

Example CXXX:

Other compounds were prepared in the same manner as in the example LXXIII. The structures and analytical data for compounds 212 and 213 used in the examples below for the reduction of plant moisture loss are given in Table R below

 Table R

Representative heterocyclic, nitrogen-containing compounds

Cl

Cl

Verb substituents iilementaranalyse

59

calculated

determined

Schmols- ρunkt, ⁰ C

212 CH ₃ CH ₂ CH ₂ C = G 44.47 3.27 19.45 40.13 2.72 19.47 oil

213 (CH ₃ J ₃ CC = C- 46.98 3.94 18.26 47.86 4.21 17.41 oil

Example CXXXI:

Preparation of 2-chloro-4-ethynyl-6-metho: scy-1, 3,5-triazine

To 1.0 g (0.004 mol) of 2,4-dichloro-6-trimethylsilylethynyl-1,3,5-triazine prepared in Example IXXII in methanol solution was added 0.235 g (0.004 mol) of potassium fluoride at a temperature of 0 ° C added. The reaction mixture was stirred for a period of 30 minutes, to which was added a saturated aqueous solution of ammonium chloride, and then the methanol was evaporated in vacuo . The residue was extracted with ether and the ether solution was added via Wa ₂ SO. dried, filtered and evaporated to give 0.33 g (0.002 mol) of 2-chloro-4-ethynyl-6-methoxy-1,3,5-traizin having a melting point of 108 ° -110 ° C. The eletronene analysis of the product gave the following:

C ₆ H ₄ ClM ₃ O

Analysis:

Calculated: C - 42.50, H - 2.38, W - 24.78. Calculated: C - 41.58, H - 2.29, N - 23.91.

This connection will be referred to as connection 214 below.

Example CXXXII:

Other compounds were prepared in the same manner as in the example LXI. The structures and analytical data of compounds 215 to 217 used in the following examples for the reduction of moisture loss of plants are given below in Table S '.

Table S

Representative heterocyclic 'nitrogenous compounds'

Cl

Verb. Substituents elementary analysis

60

calculated

determined

Schraelapunkt,

H W

HN

οιί

N '

CH ₃ O

42.05 2.35 21.79 39.68 2.98 19.60 16O to

162 (decomposition)

41.79 2.23 13.29 41.1.4 3.02 13.77 110 bis - * =

138

53,50 2,25 15,60 53,46 2,66 15,48 118 bis

Example CXXXIII:.

Preparation of 2,4-dichloro-6-phenylsulfonamido-1,3,5-tria-

In the same manner as in Example LXXIV, cyanuric chloride was reacted with benzenesulonate nitride in the presence of sodium hydroxide as the acid acceptor to give 2,4-dichloro-6-phenylsulfonamido-1,3,5-triazine having a melting point of 185 ° -186 ° C. Elemental analysis of the product showed the following:

Analysis: C ₉ H ₆ Cl ₂ K ₄ O ₂ S

Calculated: C -'35.42, H-1.98, K-18.36. Calculated: C - 35.04, Ii - 2.32, M - 18.09.

This connection is hereinafter referred to as connection 218.

Example CXXXlV:. 'Preparation of 2-chloro-4- (2,4-dichlorophenoxy) -6-hexafluoroisopropoxy- 1,3,5-triazine

To a solution of 5.0 g (0.02 mol) of the 2,4-dichloro-6- (2,4-dichlorophenoxy) -1,3,5-triazine prepared in Example IV in 100 ml of acetone was added at a temperature of At 40 ° C, add a solution of 1.9 ml (0.02 mol) of 2,6-lutidine in 75 ml of acetone, followed by a solution of 1.9 ml (0.02 ml) of hexafluoroisopropyl alcohol in 75 ml of acetone. The resulting mixture was heated under reflux for a period of 10 hours and then evaporated in vacuo to dryness. The residue was subjected to flash column chromatography on silica gel, eluting first with 5 % ethyl acetate in hexane and then with 15 % dichloromethane in hexane to give 1.34 g (0.0035 mol) 2-chloro-4- (2,4- dichlorophenoxy) -6-hexafluoroisopropoxy-1,3,5-triazine in the form of an oil. The elemental analysis of the product gave the following:

Analysis: C ₁₂ H ₄ Cl ₃ FgM ₃ O ₂

Calculated: C-37.38, H-1.05, H-10.90. Calculated: C - 32.52, H - 0.89, N - 9.48.

This compound is hereinafter referred to as compound 219.

Example CXXXV:

Preparation of 2-chloro-4- (1-naphthoxy) -6-6 (2,2,2-trifluoro-

roethoxy) -1,3,5-triazine

In the same manner as in Example CXXXIV, the 2,4-dichloro-6- (1-naphthoxy) -1,3,5-triazine prepared in Example IX was reacted with 2,2,2-trifluoroethanol in the presence of 2.6 -Lutidine reacts as an acid acceptor to give 2-chloro-4- (1-naphthoxy) -6- (2,2,2-trifluoroethoxy) -1,3,5-triazine as an oil. The elemental analysis of the product gave the following:

Analysis: C ₁₅ H ₁₉ ^ ₂

Calculated: C - 50.65, H - 2.55, II - 11.84.

Calculated: C - 51.04, H - 2.75, M - 11.53.

This connection will be referred to as connection 220 below.

Example CXXXVI:

Preparation of 2-chloro-4- (2,4-dichlorophenoxy) -6-ethoxy

1,3,5-triazine

To a suspension of 0.39 g (0.02 mol) of magnesium in 70 ml of dry tetrahydrofuran was added a solution of 3.17 g (0.02 mol) of bromoacetaldehyde diethylacetal in 10 ml of dry tetrahydrofuran. The resulting mixture was stirred at room temperature for 1 h, then a solution of 5.0 g (0.02 mol) of 2,4-dichloro-6- (2,4-dichlorophenoxy) -1,3,5-triazine was added dropwise added. The reaction mixture was stirred at room temperature for about 16 hours, evaporated to dryness, and the residue was purified by column chromatography on silica gel, eluting with 5 % ethyl acetate in hexane, yielding 1.9 g (0.01 mol) of 2-chloro-4 - (2,4-dichlorophenoxy) -6-ethoxy-1,3,5-triazine in the form of an oil. The elemental analysis of the product gave the following *

C ₁₁ H ₈ Cl ₃ N ₃ O ₂

Analysis:

Calculated: C. - 41.22, H - 2y51, H - 13.11.

Calculated: C - 41.24, H - 2.50, N - 12.75.

This connection is hereinafter referred to as connection 221.

Example CXXXVIIi

Preparation of 2-4-dichloro-6- (2,2,2-trichloroethoxy) -1,3,5-triazine +

To a solution of 5.0 g (0.03 mole of cyanuric chloride in 100 ml of acetone at a temperature of 4 ° C was added a solution of 3.16 ml (0.03 EoI) of 2,6-lutidine, followed by a solution of 2 , 60 ml (0.03 h) of 2,2,2-trichloroethanol in 150 ml of acetone was added The mixture was stirred at room temperature for about 16 hours and the solvent was removed by evaporation The residue was partitioned between water and dichloromethane The organic layer was dried over anhydrous sodium sulfate and the residue after evaporation of the solvents was purified by flash column chromatography on silica gel. Elution by ethyl acetate-hexane gave 1.1 g (0.004 H 2 O) of 2,4-dichloro-6- (2,2, 2-trichloroethoxy) -1,3,5-triazine in the form of crystals having a melting point of 72 ° -73 ° C. The elemental analysis of the product gave the following:

Analysis: C ₅ H ₂ Cl ₅ N ₃ O

Calculated: C - 20,20. H - 0.68, N - 14.13.

Determined: C - 20.19, H - 0.68, M - 14.48.

This connection will be referred to as connection 222 below.

Example CXXXVIII:

Preparation of 2-4-dichloro-6- [2- (W-methylpyrrolyl) J-1,3,5 tii

triazine

A mixture of 2.4 ml (0.03 mol) of N-methylpyrrole, 5.0 g (0.03 mol) of cyanuric chloride and 50 ml of p-dioxane was refluxed for 5 hours. The reaction mixture was poured into water, and the resulting precipitate was collected by suction filtration and dried. Crystallization from hexane gave 2.0 g (0.01 mol) of 2,4-dichloro-6- [2- (W-methylpyrrolyl)] - 1,3,5-triazine as pale yellow crystals with a melting point of 153 ° - 154 ° C The product analysis of the product showed the following:

Analysis:. CgHgCl ₂ N ₄

Calculated: C - 41.95, H - 2.64, W - 24.46.

Calculated: C - 42.00, H - 2.73, H - 24.46.

This compound is hereinafter referred to as compound 223.

Example CXX) CIX:

Preparation of ton H- (4,6-dichloro-1,3,5-triazin-2-yl) -2-oxo

hexamethyleneimine -

To a suspension of 10.0 g (0.09 mol) of potassium hydride in oil was added 200 ml of dry tetrahydrofuran at a temperature of -60 ° C, followed by the addition of 10.0 g (0.09 mol) of f.- Caprolactam at the same temperature. The mixture was warmed to room temperature and stirred for one hour whereupon a solution of 16.3 g (0.09 mol) of cyanuric chloride in 100 ml of tetrahydrofuran was added and stirring continued for a further two hours. The reaction mixture was vacuum evaporated and the residue was purified by flash chromatography, yielding 1.2 g (0.005 mol) of M - (* 4,6-dichloro-i, 3,5-triazin-2-yl) -2-oxahexamethyleneimine in the form of a Oil resulted. The elemental analysis of the product gave the following:

Analysis: C ₉ H ₁₀ Cl ₂ N ₄ O

Calculated: C - 41.40, H - 3.86, N - 21.46.

Calculated: C - 40.85, H - 4.40, N - 21.01.

This connection is hereinafter referred to as connection 224.

Example CXL:

Preparation of N- (4,6-dichloro-1,3,5-triazin-2-yl) -2-oxo

tetramethyleneimine ,

In the same manner as in Example CXXXIX, 2-pyrrolidinone was treated with potassium hydride, and the resulting potassium salt was then reacted with cyanuric chloride to give N- (4,6-dichloro-1,3,5-triazin-2-yl). -2-oxotetra-

methylenimine having a melting point of 192-194C. Elemental analysis of the product indicated the following:

C ₇ H ₆ Cl ₂ W ₄ O

Analysis:

Calculated: C-36.07, H-2.60, K-24.04. Determined: C - 35.86, H - 2.54, N - 24.01.

This compound will be referred to as compound 225 below. ^ Example CXLI:

Preparation of H- (4,6-dichloro-1,3,5-triazin-2-yl) -1,3,5-trimethyl-6-azabicyclo [3.2.1] octane and 2,4-bis (1,3, 3-trimethyl-6-azabicyclo) -3,2,2-octan-6-yl) -6-chloro-1,3,5-tria- 2 in

In the same manner as in Example CXXXIX, 1,3,3-trimethyl-6-azabicyclo [3.2.i3octane was treated with potassium hydride and the resulting potassium salt was then reacted with cyanuric chloride to give H- (4,6-dichloro-1 , 3,5-triazin-2-yl) -1,3,3-trimethyl-6-azabicycloJ3.2.1 ^ joktane having a melting point of 133 ° - 135 ° C and 2,4-bis (1,3,3-) Trimethyl-6-azabicyclo3.3.1.1octan-6-yl) -6-chloro-1,3,5-triazine having a melting point of 161.5 ° -163 ° C. by separation of the two products by flash-column chromatography. Elemental analysis and nuclear magnetic resonance analysis of the operated products revealed the following:

W- (4,6-dichloro-1,3,5-triazin-2-yl) -1,3,3-trimethyl-6-aza- bicyclo Γ3.2. i1 octane

Analysis: C ^ H-iqCIoNq

Calculated: C - 51.83, H - 6.02, N - T8.60, Cl - 23.54. Determined: C - 51.82, H - 5.81, N - 18.47, Cl - 23.78.

This connection is hereinafter referred to as connection 226.

2,4-bis (1,3,3-trimethyl-6-azabicyclo [3.2.1-octan-6-yl] -6-

chloro-1,3,5-triazine

'H-NMR _(CDCl3): 5 0.80 (s, 6H), 0.94 (s, 6H), 1.10 (s, 6H), 1.30 to 2.30 (m, 12H), 2.90-3.70 (m, 4H), 4.30-4.68 (m, 2H) Particles / Mill.

This connection will be referred to as connection 227 below.

Example CXLII:

Preparation of 4,6-dichloro-2- (3-phenylphenoxy) -1,3,5-tria-

In the same manner as in Example X, cyanuric chloride was reacted with 3-phenylphenol in the presence of triisopropanolamine as the acid acceptor, giving 4,6-dichloro-2 (3-phenylphenoxy) -1,3,5-triazine having a melting point of 183 ° - 185 ° C. The elemental analysis of the product gave the following:

Analysis: C ₁₅ H ₉ B ₃ O

Calculated: C - 56.63, H - 2.85, N - 13.21, Cl - 22.29. Determined: C - 56.33, H - 3.29, M - 13.15, Cl - 21.55.

This connection is hereinafter referred to as connection 228.

Example CXLIII: Preparation of 2,3-dichloro-N. (2-chloroanilino) ma limide

A stirred mixture of 5.0 g (0.03 mol) of o-chlorophenyl hydrazine hydrochloride, 4.7 g (0.03 mol) of dichloromaleic anhydride and 20 ml of acetic acid was heated at a temperature of 100 ° C over a period of 45 Heated for a few minutes. The mixture was cooled to room temperature and water was added dropwise, resulting in the formation of a precipitate. The first yield of the product was filtered off, and a second yield was obtained by slowly evaporating the mother liquor and a second filtrate.

tration. The combination of the two yields gave 5.55 g (0.02 mol) of 2,3-dichloro-N- (2-chloroanilino) arnlimi in the form of yellow crystals with a melting point of 137 ° to 138 ° C. The elemental analysis of Product gave the following:

Analysis: C ₁₀ H ₅ Gl ₃ H ₂ O ₂

Calculated: C - 41.20, H - 1.73, K - 9.61. Calculated: C - 40.80, H - 1.97, H - 9.75.

This compound will be referred to as compound 229 hereinafter.

Example CXLIV:

Other compounds were prepared in the same manner as in Example CXLIII. The structures and analytical data for compounds 230-250, which are obtained from plants in the examples below for reducing moisture loss, are given in Table T below

 Table T

Representative heterocyclic, nitrogen-containing compounds

Cl Cl

Verb. Substituents elementary analysis

calculated

determined

Melting point, ⁰ C

HN

HN

232

^{41 '20 1} » ^{73 9} ' ^{61 40 '68 1} ' ^{73 9 '34 173}

, 174

36,85 1,24 8,59 36,68 1,40 8,47 184,5 -

185.5

Table T (continued)

Representative Heterocyclic, Nitrogenous Compounds' «

Mr* ^{l |}

Cl

Cl

Verb. Substituents elementary analysis

* 61

calculated

determined

Melting point, ⁰ C

H K

H U

CP,

N-

OCH.

H"

40,64 1,55 8,62 40,73 1,63 8,62 174,5 -

175.5

46.02 2.81 9.76 46.06 2.82 9.78 136 Ms

138

46.02 2.81 9.76 46.08 2.71 9.66 126 to

128

CH ₂ O

46.72 2.35 10.89 46.69 2.36 10.79 166 to

Table T (continued)

Representative heterocyclioche, nitrogen-containing compounds

Cl

Cl

Verb. Substituents elementary analysis

calculated

determined

Melture C

point, o,

HN

HN

H 39.76 1.67 13.91 39.66 1.69 13.86 183 to ^K ~ 185

237 \ 0 / -CH ₂ - 51,59 2,76 5,47 51,79 2,86 5,44 107 bis

  109 cl

238 C1./qV-6H ₂ 40.65 1.55 4.31 40.65 1.63 4.48 142.5

to

Q,

Cl

240 GH ₃ OyQVcH ₂ 50,38 3,17 4,90 49,69 3,57 4,69 101 to ^ - '102

56.39 4,39 4,70 55,94 4,38 4,71 70 - 71

> v

Cl

egg

Verb. Substituents elementary analysis

enamel

calculated

point, determined o "

H H

, H 50,55 3,53 9,82 50,34 3,66 9,70 140,5 _iO > .H (CH ₂ ) ₂ -141,5

CH. 53.56 3.36 5.19 53.49 3.47 5.19 01 I ³ • CH-

53,36 3,36 5,19 53,58 3,30 5,14 131 bis

Verb. Substituents elementary analysis

R

61

calculated

determined

Melting point

HK CH N

45.47 2.08 4.82 45.83 2.22 .4.58 108 bis

110.5

Table T (continued.}.

Representative heterocyclic, nitrogen-containing compounds

Verb. substituents  Ji'lementaranalyse determined W enamel ^R 61 Erreclinet C H point, ⁰ C C HN

246

247 <p

43.93 2.05 5.69 44.16 2.21 5.76 55-56

46.18 3.88 5.98 45.64 3.91 6.25 66.5 to

48,41 4,47 5,65 48,36 4,51 5,31 138 bis

140 0

Verb. Substituents elementary analysis

calculated

determined

Melting point,

H K

40.81 2.45 6.80 41.03 2.49 6.68 118.5 to

46.34 2.12 9.82 46.33 2.11 9.83 227 to

250

Ul 37,40 1,88 0,72 37,36 1,80 8,78 186,5 bis

189

Example CXLV: Preparation of 6-hydroxy-2-phen-yl-3 (2H) pyi-idazinone

A stirred mixture of 10 ml (0.10 mole) phenylhydrazine, 10 g (0.10 mole) maleic anhydride and 75 ml acetic acid was refluxed over 2 seconds of 6 hours, the mixture was cooled to room temperature, causing crystals to settle which were filtered out to give 10.62 g (0.05 mol) of .6-hydroxy-2-phenyl-3 (2H) pyridazinone as yellow crystals melting at 262C (decomposition). The nuclear magnetic resonance analysis revealed the following: ¹ H-HMR (CDCL ₃ ): S 7.21 (AB, 2H, J = 10 Hz), 7.50 to 7.87 (m, 5H) particle size.

This compound is hereinafter referred to as compound 251.

Example CXLVI:

Preparation of 4,6-dichloro-2-phenyl-3 (2H) pyridazineor ·

A stirred mixture of 30 ml (0.32 mol) phosphorus oxychloride, 30 g (0.14 mol) phosphorus pentachloride and 5.0 g (0.024 mol) of the 6-hydroxy-2-phenyl-3 (2H) prepared in Example CXLV. Pyrxdazinone was mixed at a temperature of 160 ° to 170 ° C over a period of 90 minutes. The mixture was cooled to room temperature and poured into ice water to give a yellow precipitate. The crude product was filtered off and crystallized from methylene chloride-hexane to give 2.1 g (0.01 mol) of 4,6-dichloro-2-phenyl-3- (2H) -pyridazinone as yellow crystals with a melting point of 110 ° TLC of the product gave the following:

with a melting point of 110 ° - 111 ° C. The Slementarana

Analysis: C ₁₀ H ₆ Cl ₂ N ₂ O

Calculated: C - 49.33, H -. 2,56, K - 11,18.

Determined: C - 49.69, H - 2.61, K - 11.57.

This compound will be referred to as compound 252 below.

Beispiä. CXLVII:

Preparation of 6-chloro-2-plienyl-3 (2H) pyridazinone

A stirred mixture of 2.0 g (0.01 mol) of 6-hydroxy-2-phenyl-3- (2H) pyridazinone as prepared in Example CXLV and 20 ml (0.21 mol) of phosphorus oxychloride was added heated to a temperature of 95 C over a period of 2 hours. The reaction mixture was cooled to room temperature and then quenched with ice water. Hexane was added and the mixture was triturated to give white crystals. These crystals were filtered out to give 0.81 g (0.004 mol) of 6-chloro-2-phenyl-3 (2H) -pyridazinone as off-white crystals melting at 112-113 ° C. Elemental analysis of the product indicated the following :

Analysis: C ₁₀₇₃

Calculated: C - 58.13, H - 3.421, M - 13.56, Cl - 17.16.

Sr agent: C - 58.1 Oj H - 3.10, H - 13.41, Cl - 16.47.

This compound will be referred to as compound 253 below.

Example CXLVIII:

Preparation of 4,5-dichloro-6-hydroxy-2- (2,4-dichlorophene)

nyl) -3 (2H) pyridazinone ; ^ _

To a mixture of 18.8 g (0.09 mol) of 2,4-dichlorophenylhydrazine hydrochloride and 600 ml of 1N hydrochloric acid was added 14.7 g (0.09 mol) of dichloromaleic anhydride. The mixture was refluxed for 6 hours and the resulting solid was filtered off and washed with ice-water and hexane, yielding 7.6 g (0.023 mol) of 4,5-dichloro-6-hydroxy-2-2 (2 , 4-dichlorophenyl) -3 (2H) pyridazinone having a melting point of 295-298 ° C (decomposition). The elemeritar analysis of the product gave the following:

Analysis: C ₁₀ H.Cl.K ₂ 0_

Calculated: C - 36.85, H - 1.24, H - 8.59.

Determined: C - 36.69, H - 1.37, U - 8.44.

This compound is hereinafter referred to as compound 254.

Example CXLIX:

Preparation of 4,5-dichloro-6-hydroxy-2- (2-chlorophenyl) -

3 (2H) -pyridazinone

In the same manner as in Example CXLVIII, o-chlorophenylhydrazine hydrochloride was reacted with dichloromaleic anhydride to give 4,5-dichloro-6-hydroxy-2- (2-chlorophenyl) -3 (2H) -pyridazinone having a melting point of 242-244 ° C The elemental analysis of the product gave the following:

C ₁₀ H ₅ Cl ₃ H ₂ O ₂

Analysis:

Calculated: C - 41.20, H - 1.73, K - 9.61.

Calculated: C - 41.19, H - 1.97, N - 9.60.

This connection will be referred to as connection 255 below.

Example CL:

Preparation of 4,5-dichloro-6-hydroxy-2- (3,4-dichlorophene)

nyl) -3 (2H) -pyridazinone

A stirred mixture of 7.5 g (0.03 mol) of 3,4-diphenylhydrazine hydrochloride, 5.0 g (0.3 mol) of dichloromaleic anhydride and 100 mL of glacial acetic acid was heated at reflux for a period of two days. The mixture was cooled to room temperature, causing the precipitation of yellow-orange crystals. Suction filtration of the crystals gave 2.87 g (0.01 mol) of 4,5-dichloro-6-hydroxy-2- (3,4-dichlorophenyl) -3-C 2 H) -pyridazinone having a melting point of 241 ° to 242.5 ° C The elemental analysis of the product gave the following:

Analysis: C ₁₀ H ₄ Cl ₄ N ₂ O ₂

Calculated: C-36.85, H-1.24, H-8.59. Determined: C - 36.47, H - 2.07, K - 7.49.

This connection is hereinafter referred to as connection 256.

Example CLl:

Preparation of 2,3-dichloro-II- (2-methylanilino) malimide and 4,5 -dichloro-6-hydroxy-2- (2-methylphenyl) -3 (2H) pyridazinone

In the same manner and white as in Example CXLIII, o-tolylhydrazine hydrochloride was reacted with dichloromaleic anhydride to give 2,3-dichloro-K- (2-methylalailino) malimide having a melting point of 146 ° -149 ° C. and 4,5-dichloro -6-hydroxy-2- (2-methylphenyl) -3 (2H) pyridazinone having a melting point of 234 ° - 235.5 ° C by separation of the two products by recrystallization from methylene chloride. The elemental analysis of these two products revealed the following:

2.3-dichloro-K- (2-methylanilino) malimide:

Analysis: C ₁₁ H ₈ Cl ₂ W ₂ O ₂

Calculated: C - 48.73, H - 2.97, M - 10.33. Determined: C - 48.64, H - 3.12, N - 10.23.

This compound will be referred to as compound 257 below.

Example CLII:

Preparation of 4,5,6-trichloro-2- (2,4-dichlorophenyl) -3 (2H) -7

pyridazinone .

A stirred mixture of 3.7 g (0.02 mol) of phosphorus penturoride, 37 ml (0.4 mol) of phosphorus oxychloride and 7.6 g (0.023 mol) of the 4,5-dichloro-6-hydroxy-2 prepared in Example CXLVIII - (2,4-dichloro-periyl) -3 (2H) -pyridazinone were heated to a temperature of 160 ° -170 ° C. over a period of 14 hours. The mixture was cooled to room temperature and poured into Ki'swasser adding a small amount of hexane and stirring to promote the precipitation. The crude product was filtered, washed with ice-water and purified by flash chromatography on silica gel, eluting with 5 % ethyl acetate in hexane, yielding 0.85 g (0.0025 mol) of 4,5,6-trichloro-2- (2.4 -dichlorophenyl) -3 (2H) -pyridazinone having a melting point of 154 ° - 155.5 ° C. The elemental analysis of the product revealed the following:

C ₁₀ H ₃ Cl ₅ M ₂ O

Analysis:

Calculated: C - 34.88, H - 0.88, M - 8.13. ' Calculated: C - 34.30, H - 0.96, N - 8.20.

This compound will be referred to as compound 259 below.

Example CLIII:

4,5-dichloro-6-hydroxy-2- (2-raethylphenyl) -3 (2H) -pyridazinone:

Analysis: C ₁₁ HgCl ₂ N ₂ O ₂

Calculated: C - 48.73, H - 2.97, K - 10.33. Calculated: C - 48.29, H - 3.06, N - 10.16.

This compound will be referred to as compound 258 below.

Other compounds were prepared in the same way as in example CLII. The structure and analytical data for compounds 260 to 264 used in the following examples for the reduction of moisture loss of plants are given below in Table U *

Table U

Representative Heterocyclic Nitrogen - Containing Compounds ·. ·

-Cl

Stallen with a melting point of 115 ° - 117.5 ° C. The product analysis of the product showed the following:

Analysis: C ₁₂ H ₁ ^ ₂₂

• Calculated: C - 57.49, H - 4.42, N - 11.17. Retrieved: C - 57.49, H - 4.32, N - 11.15.

This connection will be referred to as connection 265 below.

Verb. Substituents elementary analysis

62

lirrechnet

determined

Melting paste ¹ C

point, o

H W

HN

260 H 43.59 1.83 10.17 43.33 1.81 10.01 109 to

261 2-CH ₃ 45,63 2,44 9,67 45,63 2,53 9,12 130 bis

262 2-Cl 38,75 1,30 9,04 38,89 1,39 8,79 150 bis

263 3,4-Cl ₂ 34,88 0,88 8,13 36,34 1,23 8,30 150 bis

264 3-CF ₃ 38.46 1.17 8.15 38.50 1.14 8.06 109 to

Example ClIV:

Preparation of 2,3-dimethyl-H- (2-chloroanilino) malimide

A stirred mixture of 7.1 g (0.04 mol) of o-chlorophenylhydrazine hydrochloride, 5.0 g (0.04 mol) of 2V3-dimethylmaleic anhydride and 25 ml of acetic acid was heated at a temperature of 100 ° C for one hour. The reaction mixture was cooled to room temperature and water was added dropwise, causing re-precipitation to form. The precipitate was filtered off and the filtrate was cooled, causing the crude product to settle out as a solid. The solid was crystallized from methylene chloride-hexane to give 2.3 g (0.01 mol) of 2,3-dimethyl-N- (2-chloroanilino) malimide in the form of orange-colored crystals.

Example CLV:

Other compounds were prepared in the same manner as in Part B of Example DQCXIII. The structures and analytical data for compounds 266 and 267 used in the following examples for reducing plant moisture loss are given in Table V below.

Table V

Representative heterocyclic, nitrogen-containing compounds

Verb. Substituents elementary analysis

melting

^ 63

calculated

Point,

Determines o 'υ

H H

HN

266 2,4-F ₂ 38,88 1,08 15,11 38,87 1,37 15,03 89 bis

91

267 2,3- (CH = CHCH = CH (-)

53.45 2.42 14.38 53.65 2.83 14.66 135 to

137

Example CLVI:

Preparation of H-hydroxymalimide

M-hydroxymalimide having a melting point of 133 ° -135 ° C. was purchased from Aldrich Chemical Company and used without further purification. A log P determination for the product indicated the following: octanol / log log P by high pressure liquid chromatography with phase inversion 0.00.

This compound will be referred to as compound 268 below.

Example CLVII:

Preparation of 4,5-dichloro-6-hydroxy-2- (3-trifluoromethyl- phenyl) -3 (2H) -pyridazinone ^^ _ ^

In the same manner and in the same manner as in Example CXLVIII, m-trifluoromethylphenylhydrazine hydrochloride was reacted with dichloromaleic anhydride to give 4,5-dichloro-6-hydroxy-2- (3-trifluoromethylphenylH-3 (2H) pyridazinone having a melting point of 171 ° - 172 ° C. The elemental analysis of the product gave the following:

Analysis: C ^ HcClpF ^ WpOp

Calculated: C - 40.64, H - 1.55, N - 8.62. Determined: C - 40.55, H - 1.50, N - 8.61.

This compound is hereinafter referred to as compound 269.

Example CLVIII:

Other compounds were prepared in the same manner as in Example CXLIII. The structures and analytical data of Compounds 270 to 275, which are used in the following Examples for the reduction of moisture loss of plants, are given below in Table VI.

Table ;"'

PiEprüSentative heterocyclic, nitrogen-containing compounds, '

Verb. substituents Elemental analysis determined W enamel 13 ^R 64 ^Y 86 ^Y 87 calculated C H point, ⁰ C C Hf

48.21 2.94 5.11 48.05 2.28 5.05 92 - 93.5

Cl Θ1

Cl Cl 48.21 2.94 5.11 48.14 2.28 5.05 72 - 73 -CH ₂ -

Br 49.65 3.03 5.26 49.73 3.03 5.24 51 - 52 ·

'86

Verb. Substituents Elemental Analysis '

liä -

^R 64 ^Y 86 ^Y 87

determined

H K

H IJ

Melting point ⁰ C

k2

Cl Cl 48.21 2.94 5.11 47.98 2.29 5.05 115 -

Cl Cl 41.24 1.92 5.34 41.37 2.06 5.22 86.5 -

Cl Cl 50,40 5,00 5,34 50,65 4,98 5,30 109 bis

Example CLIX:

Preparation of 2-LiIethyl-4,5i6-trichloro-3 (2H) pyridazinone

Part A. Preparation of 2-methyl-4,5-dichloro-6-hydroxy- 3 (2H) pyridinezinone

In the same manner as in Example LXLVIII, methylhydrazine was reacted with dichloromaleic anhydride in aqueous HCl solution to give 2-methyl-4,5-dichloro-6-hydroxy-3 (2H) -pyridazinone having a melting point of 229 ° to 230 ° C.

Part B. Preparation of 2-methyl-4,5,6-trichloro-3 (2H) pyridazinone

A mixture of the 2-methyl-4,5-dichloro-6-hydroxy-3 (2H) pyridazinone prepared above in Part A (3.0 g, 0.02 mol) and 20 ml of phosphorus oxychloride was heated until a solution and the excess of phosphorus oxychloride was evaporated under reduced pressure. The residue was immersed in ice water, and this mixture was then stirred for one hour to give a slurry of a ledergelfeea Peststoffs' was isolated and ^etr On ^ ⁰ ₂ SS ocknet and 0.6 g (0.003 mole) of 2-methyl- 4,5,6-trichloro-3 (2H) -pyridazinone with a melting point of 96 ° -98 ° C.

This compound is hereinafter referred to as compound 276.

Example CLX: Preparation of 2-benzyl-4 _< 5-dichloro-3 (2H) pyridazinone

Part A. Preparation of 4,5-dichloro-3 (2H) pyridazinone To a refluxing solution of 33.6 g (0.2 mol) of mucochloric acid in 160 ml of absolute ethanol was slowly added a solution of 6.7 g (0.2 Mol) of 95% hydrazine in 20 ml of ethanol. The reflux treatment was continued for an additional 2 hours after completion of the addition, after which the mixture was cooled causing precipitation of solids which were filtered off and air dried to yield 24.4 g (0.15 mole) of 4,5-dichloro-3 (2H ) pyridazinone with a melting point of 193 ° '- 194 ° C resulted.

Part B. Preparation of 2-Benzyl-4,5-dichloro-3 (2H) yyridazinone

A mixture of 6.6 g (0.04 mol) of the 4,5-dichloro-3 (2H) pyridazinone prepared above in Part A, 9.1 ml (0.08 mol) of benzyl chloride, 20 g (0.14 mol ) Potassium carbonate and 120 ml of E, N-dimethylfortnamide were heated to a temperature of 40 ° to 90 ° C, resulting in the formation of a gel from the mixture. The mixture was acidified, extracted with ether / acetone and filtered to give a brown, solid. The filtrate was partitioned between ether and water, the ethereal phase was washed with 10 % sodium carbonate solution and then with water and then dried and evaporated to give 0.5 g (0.002 mol) of 2-benzyl-4,5-dichloro-3- (2H) pyr ida zinon in the form of white crystals with a melting point of 81 ° -82 ° C. This compound is hereinafter referred to as compound 277.

Example CLXI:

Preparation of 2- (o-chlorobenzyl) -4,5-dichloro-3 (2H) pyridine

da zinon,

A mixture of 3.4 g (0.02 mol) of mucochloric acid, 5.1 g (0.02 mol) of o-chlorobenzylhydrazine-H ₂ SO.sub.5 salt and 50 ml of absolute ethanol was heated at reflux for 6 hours , The mixture was cooled and the precipitate formed was collected and air dried to give 3.8 g (0.01 mol) of 2- (o-chlorobenzyl) -4,5-dichloro.

3 (2H) -pyridazinone in i'Orm of white crystals having a melting point of 114 ⁰ C.

This compound is hereinafter referred to as compound 278.

Example CKQI:

Preparation of 2-chloro-H- (2-methylphenyl) malimide

Part A. Preparation of 2- (or 3-) chloro-IJ- (2-methylpheriyl) -maleamic acid __

A mixture of 132 g (1.0 mole) of chloromaleic anhydride and xylene was stirred and heated to a temperature of 70 ° C while slowly adding 107 g (1.0 mole) of 2-methylaniline via a dropping funnel. Upon completion of the addition of 2-methylaniline, the reaction mixture was heated at a temperature of 70 ° C for one hour. The mixture was cooled and a solid filtered, washed with xylene and hexane and then dried at room temperature yielding 225 g (0.94 mol) of 2- (or 3-) chlorophenyl- N- (2-methylphenyl) maleamic acid with a melting point of 110 ° C. .

Part B. Preparation of 2-chloro-H- (2-methylphenyl) malimide

A stirred mixture of 8 g (0.10 mol) of sodium acetate and 95.0 g (0.40 mol) of the 2- (or, 3-chloro-1- (2-methylphenyl) -maleamic acid prepared in Part A above were heated at room temperature 122 ° C , 0 g (1.2 mol) of acetic anhydride, and the resulting mixture was then stirred at a temperature of 80 ° C over a period of 40 minutes. Then the reaction mixture was cooled to a temperature of 25 C and added to 2 Ί ice water. The resulting mixture was extracted with 600 ml of ethyl ether and the kthere extract then distilled through an unfilled 1ft column (1 foot = 0.308m), yielding 75.0g (0.34 mol) of 2-chloro-M- (2-methylphenyl ) malice having a boiling point of 132 ° C at 2 mm Hg.

This compound is referred to below as compound 279.

Example CLXIII:

Other connections are made in the same way as in example CLXII. The structures and analytical data for compounds 280 to 283, which are used in the following Examples for the reduction of moisture loss of plants, are given in Table X below.

Table X

Representative heterocyclic nitrogen-containing compounds; ;

Verb. NS substituents, Rg ₅ Physical properties

3-CH ₃ 4-CH ₃

2,4- (CH ₃ ) ₂ 2-C ₂ H ₅

Boiling point 139 ° - 140 ° C / 3 mm Hg Melting point I48 ⁰ C Boiling point 148 ° - 150 ° C / 2 mm Hg Boiling point 136 ° C / 2 mm Hg

Example CLXIV:

Preparation of M-Ethyltnalimid

N-ethyltalimide was purchased from Aldrich Chemical Company and used without further purification. A log P determination for the product gave the following / octanol / water log P by high pressure liquid chromatography with phase inversion 1.10.

This compound will be referred to as compound 284 below.

Example CLXV:

Additional compounds were purchased from Maybridge Chemical Company, Limited, Trevillet, Tintagel, Cornwall, United Kingdom and evaluated for their activity. The structures and analytical data for compounds 285 to 288 used in the examples below for reducing plant moisture loss are given in Table Y below.

Table Y

Representative heterocyclic 'nitrogenous compounds'

^R 66 ~

Verb. MS substituents

^R 66 © - ^Y 88 ^Y 8? With Cl, 285 H br 2.31 286 Cl Cl Cl 2.74 287 C ₃ H ₅ O Cl Cl O 2.57

log P octanol / water by reverse phase HPLC

Verb. Substituents

"66

log P octanol / water by reverse phase HPLC

-CH _p HH 1.83

Beispiel.CLXVI:

Preparation of 2- (3-trifluoromethyl) -4,5-dichloro-3 (2H) py-

ridazinon

2- (3-trifluoromethyl) -4,5-dichloro-3 (2H) -pyridazlone was purchased from Aldrich Chemical Company and used without further purification. Determination of log P for the product gave the following: log P octanol / water by high pressure liquid chromatography with phase inversion 2.90.

This compound will be referred to as compound 289 below. ,

Example CLXVII:

Preparation of N- (2-ethoxyphenyl) -siikzinimide

A mixture of 50 g (0.5 mol) of succinic anhydride and 300 ml of toluene was stirred and heated at a temperature of 115 ° to 120 ° C, and to this mixture was added 69 g (0.5 mol) of 2-ethoxyaniline through a dropping funnel , Then the reaction mixture was heated to boiling and the toluene distilled to a circulation temperature of 180 ° - 190 ° C. The mixture was heated to a temperature of 180 ° -190 ° until the theoretical amount of water from the system was distilled. The reaction mixture was cooled, diluted with one liter of 95% isopropyl alcohol and allowed to stand for about 16 hours. The settled solid was filtered off, washed with isopropyl alcohol and dried to give 72.0 g (0.33 mol) of N- (2-ethoxyphenyl) succinimide having a melting point of 108:

C. Elemental analysis of the product revealed

Analysis: C ₁₂ H ₁₃ MO ₃ Calculated: N - 6.39

 Retrieved: K - 6.73.

This connection will be referred to as connection 290 below.

BeispielCLXVIII:

Preparation of 3,5-dichloro-6- (3,5-dichloro-4-msthoxyphenyl) -

4-hydroxypyridazine

3,5-dichloro-O- (3,5-dichloro-4-methoxyphenyl) -4-hydroxypyridazine was purchased as a sample from Chemie Linz Company and used without further purification. The magnetic resonance analysis of the product gave the following: ¹ H-NMR (CDCl3, / DMSO-dg): 0 164.50, 152.77, 147.92, 141.99, 131.05, 130.58, 128.88 , 128.34 and 60.51 particles / mill.

This compound will be referred to as compound 291 below.

Example CLXIX:

Other compounds were prepared in the same manner as in Example CLXII. The structures and analytical data for compounds 292 to 296 used in the examples below for reducing plant moisture loss are given in Table Z below.

ro

VD

ro

VD

Ω I- ¹ Ω Ω I- ¹ Ω H J> O VJI 03 VD VD VJI -> ro VJ 03 VD VD 4 * VJL VJl 03 £ VJL OD O VD VJ

VJI 03

VJI

03

ro ro 03 VJL ι - 125 VJJ O

Ω H

to

VJ

Cn VJ

cn O

O ro

03

VJL VJ

VD O

(Dhj

he ¹

td 1-3

0 H

cn

-J

S =!

VD

VD O

[3 * (D tf- (0 H O

to

(D

ο to

O H>

(D

σ

Kn te!

ο Ω H ro α H ο H 33 ' K ο 59,6- OD U) ro Ul U) U) ro Ul VO

U) O

U) (V)

fei

(D

D ¹

a ¹ m

ct "

H-

cl · P

CO O

(D H

o °

K K

D KD ->. O

(D (D - ISI

ro ro

rf-to

Example CLXX:

Exposure of Representative Heterocyclic Nitrogen Containing Compounds to Foliar Diffusion Resistance and Transpiration Rate ______________________

Sheet diffusion resistance is a measure of the resistance to diffusion of water vapor from a sheet and is an indication of the rate of transpiration. The transpiration rate is the measurement of the evaporation of water from the cell walls and the diffusion of water from the Bla.tt through the stomata (stomata) over a given period of time. The relationship between sheet diffusion resistance and transpiration rate can be summarized as follows: the higher the sheet diffusion resistance, the lower the transpiration rate, and the lower the sheet deflection resistance, the higher the transpiration rate. Leaf diffusion resistance and transpiration rate, as used below in Table AA, were determined by the following general procedure:

Solutions of the test compounds were prepared by dissolving 30.3 mg of the compound in 5.5 ml of acetone and adding water to a volume of 11.0 ml. When turbidity of the solution appeared on addition of water, the addition of water was discontinued, and it was acetone to a final volume of 11.0. ml added. The resulting stock solutions contained 2530 parts / mill. the connection on weight basis. The experimental concentrations in parts of the test compound per milliliter parts by weight of the final solution used, which were used below in Table AA, were prepared by appropriate concentrations of the stock suspensions with water.

One cup of pottery was placed in 13.5 cm plastic tubes, ie one third sandy loam, one third peat moss and one third perlite on a volume basis, and three bean seeds ( Phaseolus

vulgaria var. cranberry). Five to ten days after planting, the plants were diluted to one plant per pot. Ten to twelve times after planting at the time the primary leaves were fully deployed, the respective concentration of the test compounds (each pot was sprayed with 5 ml of the solution) was sprayed on three bean plants as foliage spray using a suction sprayer with a 10 psig (70.31 x 10 " ¹ kp / cm ² gauge pressure.) A water-acetone solution without test compound was also applied to three bean plants, after drying all plants were kept at a temperature of 80 ° -5 ° F (about 27 ° G). brought and a humidity of 50 ± 5% in a greenhouse. Twenty-four and 48 hours after treatment, the sheet diffusion resistance were in s / cm (seconds / cm), and the transpiration rate in> ig H ₂ 0 / cm ² .s (micrograms water / Square centimeter second) using a steady state porometer Li-COR 1600 as commercially available from Li-Cor, Inc./Li-Cor.Ltd., Lincoln, Nebra ska, available, certainly. The values obtained for the individual concentrations of the test compounds and the control sample were used to form the average, in order to obtain the values given in Table AA. Fourth to determine.

Table A'A

Effect of Representative Heterocyclic, Nitrogen-containing Compounds on Sheet Diffusion Resistance and Transpiration Rate

Verb. Leaf diffusion resistance Transpiration rate KS (s / cm) Cug H ₂ 0 / cm ² .s)

1840 part./Mill. control 1840 part./Mill. Contr. 1 13.8 3.3 0.3 1.4 2 14.0 6.0 1.3 3.3 3 12.1 3.4 0.8 2.3 4 15.5 (c) 5.6 0.6 (c) 2.2 5 7.8 4.8 1.2 1.9 6 16.5 4.3 0.5 1.7 7 11.0 5.5 0.6 1.2 8th 14.0 3.3 0.5 1.7 9 7.5 6.0 0.8 1.0 10 4.6 2.2 0.8 1.5 11 4.6 2.2 , 0.8 1.6 12 4.8 (c) 2.5 0.8 (c) 1.2 13 12.7 7.6 1.0 1.5 H 4.9 2.9 0.8 1.2 15 25.8 5.0 0,4 ' 1.6 16 18.0 5.7 0.5 1.5 17 11.1 5.8 0.8 1.3 18 9.4 4.9 1.0 2.2 19 9.9 6.0 0.8 1.3 20 18.0 5.4 o, 7 2.1 21 8.7 1.7 1.1 5.0 22 8.9 2.8 • 1.0 2.9 23 13.6 4.7 0.8 2.0 24 24.9 (b) 4.6 0.4 (b) 1.3 25 26.5 5.8 0.6 2.5

Table AA (continued)

Effect of representative heterocyclic nitrogen containing compound on leaf diffusion resistance and transpiration rate

Verb. Leaf diffusion resistance transpiration rate IS s / cm) (^ Ag H ₂ 0 / cm .s)

Teil./Mill. 1840 control 1840 TeiWMill. Contr. 26 24.8 6.2 0.4 1.9 27 6.9 (b) 2.2 2,3 (b) 6.5 28 5.9 1.9 2.6 5.9 29 13.8 4.3 0.8 2.9 30 30.7 3.7 0.4 2.8 31 28.2 6.1 0.6 2.6 32 16.6 3.4 0.9 3.6 33 , 11.8 6.4 0.9 1.7 34 10.7 5.6 0.7 1.2 35 12.9 (b) 5.7 0.5 (b) 1.3 36 7.2 3.8 0.9 1.6 37 6.7 3.8 0.6 1.0 38 4.4 2.5 0.7 1.4 39 5.1 2.5 0.7 1.4 40 7.6 3.0 0.6 1.5 41 3.6 3.0 1.0 1.4 42 14.6. 4.0 0.4 1.5 43 13.7 9.3 0.6 0.9 44 16.7 4.3. 1.0 3.5 45 6.6 5.9 1.7 1.8 46 9.3 3.3 2.3 4.0 47 25.6 3.8 0.7 4.1

Table AA (continued)

Effect of representative heterocyclic nitrogen containing compounds on leaf diffusion resistance and transpiration rate

Verb. Leaf diffusion resistance control transpiration , Contr. (S / cm) 9.4 (^ g H ₂ 0 / cm. 0.9 1840 part./Mill. 9.1 1840 part./Mill 1.3 48 10.1 (b) 4.8 0.8 (b) 1.9 49 10.2 5.6 1.1 1.5 50 9.3 3,3, 1.0 3.4 51 15.8 4.4 0.5 1.3 52 13.2 2.4 1.8 3.3 53 · 11.6 4.3 0.5 3.3 54 7.8 6.2 1.0 2.5 55 8.4 2.1 1.1 3.7 56 16.1 2.8 1.0 2.3 57 ' 6.4 2.8 1.3 2.2 58 3.8 1.8 1.7 3.8 59 8.2 5.6 0.8 1.5 60 3.9 5.5 2.1 1.5 61 9.5 6.9 0.9 1.4 62 15.4 4.2 0.6 ³³ J ' 63 8.5 13.9 1.1 0.8 64 8.7 8.5 1.6 0.8 65 21.7 8.1 0.4 0.9 66 11.2 (c) 4.4 0.7 (c) 1.4 67 10.7 4.4 0.7 1.3 68 5.2 1.2 69 12.1 0.5

Table AA (continued)

Effect of Representative Heterocyclic Nitrogen-containing Compounds on Sheet Diffusion Stability and Transpiration Rate

Verb. Leaf Diffusion Perspiration Transpiration Rate Hi (s / cm) (jug H ₂ O / cm ² .s)

1840 Teil./Mill, control 1840 Teil./Mill. Contr. 70 3.4 2.2 0.8 1.3 71 2.5 2.0 1.4 1.6 72 14.4 2.1 1.4 4.3 73 5.4 3.6 1.4 2.0 74 5.0 (B) 3.2 0.9 (B) 1.4 75 10.3 6.3 1.3 1.8 76 12.7 7.4 1.0 1.7 77 13.5 4.4 0.6 1.9 78 10.3 3.7 1.1 2.8 79 19.8 5.3 0.4 1.4 80 14.4 (C) 7.6 0.8 (O) 1.5 81 10.1 (C) 4.7 1.0 (O) 2.0 82 19.0 , 6.1 0.5 1.3 83 26.7 6.5 0.3 1.2 84 7.4 (C) 6.5 1.1 (C) 1.3 85 13.4 9.2 1.0 1.6 86 6.8 4.0 1.1 1.5 87 14.8 4.3 0.9 2.8 88 6.5 6.8 1.0 1.2 89 11.4 (B) 9.7 1.0 (B) 1.2 90 10.4 (E) 5.8 1.2 (E) 2.0 91 4.8 3.3 1.6 2.2

Table AA (continued)

Effect of representative heterocyclic nitrogen containing compounds on leaf diffusion resistance and transpiration rate

Verb. Leaf diffusion resistance Transpiration rate P (s / cm) Hg H _o 0 / cm ² .s)

1840 part. / Mill. control 18 * 40 Teil./Mill. Contr. 92 9.5 3.9 0.7 1.6 93 8.1 3 »5 0.9 2.0 94 12.0 6.8 0.8 1.3 95 10.0 (b) 6.4 0.9 (B) 1.4 96 10.0 6.5 1.0 1.4 97 3.1 1.7 1.6 ί 2.1 98 2.7   1.3 1.4 2.6 99 17.1 9.9 0.5 0.9 100 6.2 4.3 1.3 1.8 101 15.2 (b) 7.9 0.7 (B) 1.3 102 13.3 (b) 4.7 0.9 (B) 2.0 103 10.5 (b) 5.5 1.8 (B) 2.5 104 8.6 2.1. 1.2 4.2 105 9.9 5.4 0.9 1.6 106 12.3 10.1 1.0 1.3 107 7.4 2.4 0.5 1.4 108 22.8 9.5 0.4 1.0 109 7.1 5.1 1.4 2.0 110 14.2 (b) 6.3 0.7 (B) 1.4 111 11.2 .5,7 0.8 1.4 112 10.9 6.7 1.0 1.6 113 13.3 (b). 5.6 0.6 (B) 1.3

Table AA (continued)

Effect of representative heterocyclic nitrogen containing compounds on leaf diffusion resistance and transpiration rate .

Verb. Leaf Diffusion Transpiration Rate

, ρ

ti? (s / cm) jig HgO / cm.

1840 Teil./Mill. control 1840 Teil./Mill. Contr. 114 15.0 (B) 6.0 0.6 (B) 1.4 115 8.0 6.6 0.9 1.1 116 8.6 7.0 1.2 1.7 117 13.5 3, -6 0.7 2.2 118 3.3 2.0 1.2  1.8 119 8.7 7.1 0.6 0.8 120 10.1 9.8 1.1 1.3 121 11.4 5.7 0.7 1.3 122 8.7 (B) 6.6 0.8 (B) 1.4 123 1.9 1.0 2.4 3.9 124 1.8 (B) 1.3 2.3 (B) 2.6 125 8.9 6.6 0.8 1.1 126 6.2 5.8 · 1.2 1.3 127 7.9 5.4 1.0 1.4 128 12.1 5.8 0.7 1.6 129 5.1 4.2 1.1 1.4 130 6.8 5.0 0.8 1.0 131 11.2 5.0 0.6 1.3 132 12.6 (c). 7.3 0.9 (C) 1.5 133 6.6 4.3 1.3 2.0 125 9.7 8,3. 1.2 1.5 134 11.0 8.4 "1.3 1.5

Table AA (continued)

Effect of Representative Heterocyclic Nitrogen Containing Compounds on Sheet Diffusion Resistance and Transpiration Rate

Verb. Leaf Diffusion Transpirabion Rate

liä (s / cm) (^ HgO / cm.

Teil./Mill. Control 1840 Part./Mill. Contr.

136 3.9 (C) 3.7 137 6.4 (O) 5.7 138. 6.7 (C) 2.6 139 7.7 5.3 HO 8.8 (C) 7.1 Hi 10.8 (C) 6.2 142 8.4 6.7 143 6.5 5.2 144 8.1 (C) 4.9 145 12.6 8.6 146 8.4 8.2 147 7.8 (C) 4.8 148 11.1 (O)- 7.4 H9 6.3 (C) 5.4 150 5V5 4.6 151 8.3 (C) 6.1 152 12.7 6.5 153 H _S 9 (B) 2.3 154 9.4 (B) 8.1 155 28.4 6.7 156 12.0 5.8 157 9.5 2.2

2.4

1.3 (c) 0.6 (c) 1.0 (o) 1.5 0.7 (c)

1.3 (c) 1.3 0.9

0.8 (c) 1.1

1.1 0.5 (c ·)

1.4 (c) 1.4 (c) 1.7

0.7 (c) 0.6

0.8 (b) 0.3 (b) 0.6 '0.6

2.6 1.4 1.4 1.5 1.3 1.2 1.8 1.7 1.4 1.1 1.2

1.7 0.8 1.6 1.6 2.3 1.3 3.5 1.0 1.1 1.2 1.9

Table AA (continued)

Effect of Representative Heterocyclic Nitrogen Containing Compounds on Sheet Diffusion Resistance and Transpiration Rate

Verb. Leaf Diffusion Transpiration Rate Ι »? (s / cm) (ug H ₂ 0 / cm ² .s)

158 10.8 5.0 0.6 1.3 159 6.3 1.9 0.7 1.6 160 6.5 4.4 0.9 1.4 161 17.2 8.2 0.3 0.8 162 4.3 (a) 3.4 • 0.9 (a) 1.2 163 3.2 (a)   2.6 1.0 (a) 1.3 164 4.6 4.4 '2,3 2.4 165 4.0 3.6 2.5 2.9 166 5,6 (d) 4.9 1.1 (d) 1.3 167 9.9 9.7 1.2 1.3 168 4.2 3.5 2.2 2.7 169 5.4 5.2 1.9 2.1 170 6.8 3.1 1.2   3.0 171 6.4 5.2 1.2 1.5 172 11.2 8.1 1.1 1.4 173 22.2 4.9 0.5 2.0 174 10.6 6.3 0.8 1.9 175 6.4 4.2 1.8 2.6 176 6.3 4.9 2.1 2.6 177 7.3 6.6 1.4 1.6 178 38.0   5.5 0.5 3.1 179 12.4 4.8 /H 2.3

Table AA (continued)

Effect of representative heterocyclic nitrogen containing compounds on leaf diffusion resistance and transpiration rate

Ver. Leaf Diffusion Transpiration Rate iiJ (s / cm) (ng H ₂ 0 / cm ² .s)>

Teil./Mill. Control 1840 Part./Mill. Contr.

1.8 2.7 2.3 3.5 2.0 1.8 2.0 2.3 3.7 2.6 2.6 3.3. 1.7 1.8 1.9 3.5 2.6 4.6 5.1 5.1 4.0 3.9 3.7

180 7.3 6.9 · 1.7 181 10.8 5.4 2.0 182 5.7 3.5 2.0 183 16.6 8.5 1.0 184 7.1 4.0 1.0 185 5.4 · 4.9 1.9 186 7.3 5.8 1.7 187 6.7 2.6 1.1 188 8.7 4.7 1.6 189 11.5 5.7 1.6 190 2.7 2.5 3.1 191 12.3 6.4 1.1 192 15.0 9.3 1.1 193 5.2 4.0 1.4 194 3.7 2.5 2.5 195 9.5 3.9 1.3 196 14.1 2.2 0.9 197 23.1 3.3 0.7 198 19.2 1.8 0.7 199 17.1 3.7 0.9 200 8.2 2.5 1.3 201 20.4 3.8 0.8

Table AA (continued)

Effect of representative heterocyclic nitrogen containing compounds on leaf diffusion resistance and transpiration rate

Verb. Leaf Diffusion Transpiration Rate IiS (s / om) (_ug H _g O / om ² .s)

Ί840 part./mill. control 1840'Teil. / Mill. Contr. 202 9.5 3.5 2.0 4.3 203 19.7 8.8 0.7 1.7 204 30.3 4; i 0.6 3.5 205   7.7 6.2 1.4 1.7 206 9.3 6.0 1.4 2.0 207 20.9 6.6 0.6 1.7 207 13.5 4.8 1.1 3.0 209 8.1 5.4 1.1 2.0 210 7.1 5.4 1.7 2.3 211 6.0 (c) 5.6 2,3 (c) 2.5 212 7.8. (B) 4.5 1.6 (b) 2.7 213 6.0 (b) 5.9 2.0 (b) 2.1 214 9.3 7.1 1.2 1.6 215 6.6 5.5. 1.0 1.3 216 '7,9 5.8 1.4 1.9 217 5.9 4.6 1.7 2.1 218 7.5 4.6 1.5 2.0 219 8.3 3.1 1.8 4.6 220 14.0 4.6 0.8 2.3 221 10.6 5.5 1.2 2.4 222 23.0 6.9 0.5 1.6 223 9.9 5.6 1.3 a, i 224 9.4 3.8 1.7 3.7

Table AA (continued)

Effect of Representative Heterocyclic Nitrogen-containing Compounds on Sheet Diffusion Resistance and Transpiration Rate

Verb. Leaf diffusion resistance Transpiration rate Kä (e / ctn) Qig H ₂ 0 / cm ² .s)

1840 part. /Mill.Kontrolle 1840 part./Mill. Contr. 225 6.7 5.7 2.4 3.1 226 9.6 6.9 1.7 2.2 227 8.4 (b) 6.7 1.8 (b) 2.3 228 31.1 5.7 0.5 2.3 229 25.0 3.6 0.4 2.5 230 25.1 6.7 O,' 1.6 231 5.9 2.1 1.9 4.3 232 6.9 3.8 2.8 · 4.0 233 11.8 4.2 1.6 4.4 234 15.4 (b) 3.7 0.9 (b) 3.3 235 12.6 3.1 1.0 4.0 236 6.7 5.3 1.7 2.1 237 21.8 2.6 0.7 5.1 238 3.7 2.6 2.9 3.9 239 25.1 2.6 0.8 4.4 240 11.4 5.5 1.3 2.7 241 11.2 (c) 3.6 1.3 (c) 3.5 242 11.5 2.1 1.3 6.2 243 18.3 5.6 0.6 ' 1.8 244 11.5 2.9 0.4 1.4 245 10.8 3.4 1.4 3.9 246 11.4 3.0 1.1 3.9 247 10.4 2.6 1.5 5.2

Table AA (continued)

Effect of representative heterocyclic, nitrogen-containing compounds on. leaf diffusion resistance and transpiration rate

Table AA (continued)

Effect of representative heterocyclic nitrogen containing compounds on leaf diffusion resistance and transpiration rate

Verb. Leaf diffusion resistance Transpiration rate SS (s / cm) (> g H ₂ O / cm ² .s)

Verb. Leaf Diffusion Transpiration Rate

(S / cm)

18840 part. / Mill. control 1840 part./Mill. Contr. 248 3.8 2.5 1.1 1.6 249 3.1 2.8 3.9 4.3 250 2.6 1.9 6.0 8.2 251 3.3   2.8 3.8 4.1 252 5.1 4.1 2.3 2.9 253 3.3 (b) 2.7 3.5 (b) 4.1 254 "5., 4 4, '2 1.5 2.0 255 5.0 3.8 2.0 2.9 256 4.3 2.2 3.2 5.5 257 28.8 3.9 0.5 3.4 258 2.9 2.7 4.0 4.7 259 14.2 4.7 0.7 1.9 260 30.1 • 2.9 0.4 3.2 261 10.4 3.2 0.4 1.2 262 17.8 2.8 0.5 3.6 263 10.2 3.3 0.4 1.2 264 22.8 4.6 0.6 2.7 265 3.7 2.6 2.5 3.5 266 14.3 5.7 1.2 2.9 267 12.0 4.1 1.0 2.4 268 6.1 2.6 3.2 6.7 269 11.3 6,9. 1.7 2.6 270 19.5 6.4 ° "? 2.6

H ₂ O / crn .s)

1840 Teil./Mill. control 1840 Teil./Mill. Contr. 271 19.5 (C) 7.9 0.9 (C) - 2.4 272 18.6 4.7 0.9 3.5 273 18.8 5.1. 0.8 3.1 274 21.8 4.9 0.8 3.3 275 6.9 3.3 1.6 3.2 276 5.3 4.3 2.2 2.9 277 5.0 (C) 3.5 3.0 (Ο) 3.4 278 11.0 4.5 1.8 2.7 279 14.6 4.0 0.9 2.8 280 17.6 3.1 0.6 3.4 281 14.8 , 5.3 0.9 2.3 282 12.4 3.3 1.1 3.1 283 9.3 3.7 1.8 4.4. 284 8.8 (D) 3.9 1.5 (D) 3.0. 285 13.9 2.4 1.0 5.5 286 9.7 2.0 1.2 5.1 287 5.6 2.4 0.7 1.5 288 6.2 3.4 2 _S 2 3.8 289 3.5 2.8 3.3 4.3 290 9.0 6.2 2.0 2.7 291 2.1  1.9 1.4 1.5 292 23.8 (D) 6.2 0.6 (B) 2.3 293 4.8 (C) 4.4 2.3 (C) 2.4

Table AA (continued)

Description of representative heterocyclic nitrogenous compounds on leaf diffusion resistance and transpiration rate

Verb. Leaf Diffusion Resistance:. Transpiration Rate Hi (s / cm) (jig LO / cm, s)

1840 5 Part. / Mill. control 3 1840 5 Part. / Mill. Contr. ,8th 294 31 3 9 .5 0 5 1 , 4 295 28 6 (O) 7 , 7 C., 5 (C) 1 , 0 296 27 6 0 2

(a) Treated with 115 particles / mill.

(b) Treated with 230 particles / mill.

(c) Treated at 460 troughs / mill

 Cd) Treated at 920 particles / mill., (E) Treated at 3220 particles / mill. ·

The results in Table AA show that the representative heterocyclic nitrogen-containing compounds used in the method of the present invention increase leaf diffusion resistance significantly and lower the transpiration rate, both compared to untreated control plants.

Example ClXXI:

Effectiveness of the use of water of the representative hetero-

cyclic, nitrogenous compounds

The effectiveness of water use (WUE) is the determination of both the effectiveness of an antiperspirant compound, i. H. the control of water use by the plants, as well as the effect of such a compound on plant growth, d. h., the effect on the photosynthesis of the plant. The WUE is specifically defined as the unit of dry matter mass produced per unit of water used over a given period of time. The WUE, as used in Tables BB to PF below, is determined by the following general procedure:

Solutions of the compounds listed in Tables BB to W were prepared by dissolving 62.5 mg of the test compound in 5 ml of acetone. Two, one and 0.5 milliliters of this solution were placed in separate tubes, to each of which tubes acetone was added to a total volume of 12 ml and then water to a total volume of 20 ml. The final concentration of the uptake compound in the stock solutions above was 1250 particles / mill., 625 x particles / mill. and 312 particles / mill. on a weight basis. The other concentrations of test compound particles per million weight particles of final solutions used in the experiments described below were prepared by appropriate dilution of the stock solutions with water.

In 10.2 cm diameter plastic pots containing potting soil, ie one-third sandy loam, one-third peat bog and one-third perlite, all on a volume basis, were seeded 12 mg of Kentucky cattle grass seeds or fescue seeds. The plastic containers and the potting soil were weighed before sowing the seeds. The cattle grass and the fescue grass were grown 8 b ^ s 12 weeks after sowing, and the height of the grass was found to be 2.5 to 3.8 cm in this period. Twelve hours before application of the test compounds shown in Tables 0 to S, cattle grass and fescue were cut to a uniform height of 2.5-3.8 cm, and the weight of each vessel was determined before treatment. The individual concentrations of the test compounds, including the control samples, were applied by spraying four vessels (each pot was sprayed with 5 ml of the solution) with a suction sprayer which had an air pressure of 10 psig (70.31 x 10, kp / cm ² gauge). As a control, a water-acetone solution containing no experimental compound was also applied to four vessels. After drying, all vessels were placed in a greenhouse at a temperature of 80 ° to 5 ° F (about 27 ° C) and a humidity of 50 r-5% by weight for a period of 7 days without irrigation.

ben. All vessels were weighed every 24 hours and the amount of water used was determined by calculation using the daily weights given with the initial weight. At the end of the 7-day time period, the (irises in all vessels were visually estimated, then the grasses were cut to a uniform height, the cut grasses were collected for each vessel, dried and weighed, and the water usage was calculated using the following equation :

Viassernutzung =

G H_0 used by treated grasses

the contr.) g BLO (control) used by untreated grasses

The WUE was calculated using the following equation:

mg of the dry weight of the lawn cut

WUE = _: .-.---

g of the water used

The WUE was standardized for control for each of the experiments using the following equation:

«Abeile BB:

Effectiveness of Water Utilization of Representative Heterocyclic Nitrogen Containing Compounds in Kentucky ViehKi-as :

Verb, iiä Concentration Water solution ViUE WUE Index (Particle / Mill) {% d. Contr.)

Control - 312 28 625th 1250 312 30 625 1250 312 44 625 1250

100

55 57 54

62 64 65

66 48 35

0.59 '1.00

1.45 2.46 2,0.4 3.46 2.59 4.39 1.25 2.12 1.53 2.59 1.33 2.25 1.76 2.98 2.40 4.07 4.05 6.86

WUE Index

TOE for. Treated grasses

WUE for untreated grasses (control)

For the values determined for the individual concentrations of the test compounds and the control samples, average values were calculated which were used in tables BB to PF to determine the results.

Table CC:

Effectiveness of Vector Use of Representative Heterocyclic Nitrogen Containing Compounds in Kentucky Cattle Grass

Verb, ilä Concentration Water Use WUE WUE Index (Particles / Mill.) (% D.

Control - 1250 39 atrazine * 78 156 312 312 26 625 1250 312 44 625

100

48 36 37 36

63 59 65

41 39 36

0,78 1,00

1.42 1.82

1.34 1.72

0.44 0.56

0.31 0.40

2.49 3.19

1.72 2.21

1,20 1,54

3.07 3.94

3.56 4.56

3,51 4,50

Grass damaged at all concentrations; Almost all grasses died at concentrations greater than 78 particles per mill. considerable phytotoxicity.

Table DD:

Effectiveness of hatred of representative heterocyclic nitrogenous compounds in Kentucky cattle grass

Verb IS concentration water use WUE WUE index (particles / mill.) (% Of control)

2,47 1,00

2.87 1.03

2.42 1.16

2.65 0.98

2.65 1.07

2,85 1,15

3.00 1.21

3,70 1,50

4.38 1.77

3.94 1.59

2.54 1.03

2,47 1,00

2.73 1.11

Grass damaged at all concentrations'; considerable phytotoxicity.

Control - 20 100 Atrazine ^x 10 39 65 312 ' 64 625 65 32 1250 89 625 81 938 87 44 1250 58 312 52 625 49 64 1250 86 87 86

Table EE:

Effectiveness of water utilization of representative heterocyclic nitrogenous compounds in Kentucky cattle grass

Comp. B Concentration Water use WUE WUE Index (Particles / Mill.) {% D. Control)

Control - 625 100 3.90 1 00 44 938 49.0 8, "00 2 , 05 312 41.3 12,00 3 , 08 54 625 63.9 7.00 1 , 79 63.1 6.50 1 .67

Table Fi ¹ :

Effectiveness of water utilization of representative cyclic, nitrogenous compounds in Schwingel grass

Cons. KS Concentration Water Use WUE WUE Index (Particles / Mill.) (.% Of control)

0,74 1,00

1.26 1.70 1.09 1.47 0.80 1.35

1.28 1.60 2.02 2.73 1.75 2.36

1.56 2.11 2.04 2.76

1.77 2.39 0.99 1.34 1.86 2.51

^x grass damaged at all concentrations; considerable phytotoxicity.

The results in Tables BB to FF show that. compounds representative heterocyclic nitrogen-containing Yer, the · be used in the present invention to reduce the water consumption in comparison with untreated control plants considerably, without giving rise to negative effects on plant growth, that is, no negative effect on the photosynthesis of plants, On the other hand caused the treatment the grass with atrazine to a considerable phytotoxicity.

Control - VJL 100 atrazine 10 81 20 83 312 106 18 625 62 1250 61 625 57 44 1250 78 312 54 101 625 96 1250 58 52

Example CIXXII:

Effect of Representative Heterocyclic, Nitrogen-containing Compounds on Increasing Harvest - Cereals

The agricultural use of compounds with antiperspirant activity includes not only the water saving, but also the increase of crop yields. Thus, an antiperspirant compound applied to a fruit can not only reduce water demand but also increase actual crop yield by reducing water loss during periods of critical water demand. The increase in crop yield, as shown below in Table GG, was determined for cereals according to the following general procedure:

Solutions of compound 44 were prepared by dissolving 0.78 g, 1.55 g, or 3.10 g of the compound in 780 mL of acetone. Immediately prior to the time of application, water was added to each of the above solutions to a final volume of 1300 ml. Also, solutions of a control sample without trial compound were prepared, to which 780 ml of acetone and 520 ml of water were mixed to a total volume of 1300 ml.

The above compositions were applied to cereals using a 42-surface statistical treatment method. Each area consisted of 4 each 20 feet long Riehnhn (about 6.1 m) with a row spacing of about 3 feet (about 91 cm). Each experiment was constructed as a randomized, complete block of six different repeats, the repetitions including: <1) treatment with a control solution without trial compound; (2) treatment with a solution of 0.78 g / square of Compound 44 to ZeIfT ₁ designated in Table GG; (3) treatment with 1.55 g of compound 44 / area at time T ₁ , designated in Table GG; (4) treatment with 3.10 g of compound 44 / area at time T ₁ designated in Table GG;

(5) treatment with 0.78 g of compound 44 / area at time T "designated in Table GG; (6) treatment with 1.55 g of compound 44 / area to the T cell T ₂ designated in Table GG; and (7) treatment with 3.10 g of the compound 44 area at time T ₂ reported in U.S. Pat Table GG is designated. The above compositions were applied with a carbon dioxide backpressure sprayer set at an air pressure of 20-40 psig (about 1.406 to 2.812 kp / cm ² gauge). Planting, application and harvest time for the crop are detailed in Table GG. For the determination of the yield, the gascntete grain of the middle 10 feet (3.048 m) of the two middle rows of each area was used (5 feet about 1.5 m) from the ends of the two middle rows). During at least a portion of the growth period, water stress conditions existed to some extent. The values obtained for each area in each repetition were used to obtain the mean to obtain the results in Table GG

 • Table GG-

Effect of Representative Heterocyclic Nitrogen-Containing Compounds on Increasing Harvest - Cereals

verb , Concentration application schedule 0.78 3 - ^x Actual He , 87 (Kg / area) Ks' (G / area) 1.55 3 Scar threads (T ₁ ) contract , 71 Control - 3.10 3 Scar threads (T ₁ ) -9. , 62 44 0.78 Ilarben threads (T ₁ ) 10 , 3? 1.55 Weeks after Harbenfäden 10 11 3.10 Weeks after scarring 10 11 17 44 Weeks after scarring (T ₂ ) 10 , 18 (T ₂ ) 30 (T ₂ )

^x First application with trained Ilarbenfäden (T ₁ ), 46 days after planting; application three weeks after formation of the scar threads (T ₂ ), 67 days after planting,

Jl "Ο

The results in Table GG show that the treatment of cereals (corn) with a representative heterocyclic, nitrogenous compound, i.e. h>, Compound 44, according to the method of the present invention substantially increases the yield of cereals (maize) compared to untreated cereal seeds under similar conditions.

Example GLXIII:

Effect of representative heterocyclic nitrogenous compounds on increasing crop cotton

The agricultural use of compound with antiperspirant activity includes not only the saving of water, but also the increase of crop yield. By way of illustration, an antiperspirant compound applied to a fruit can increase actual crop yields by reducing water loss during periods of critical water consumption. · The increase in crop yield for cotton used in Table HH above was determined by the following general procedure:

Solutions of compound 44 were prepared by dissolving .78 S> 1.55 g or 3.10 g of the compound in 780 ml of acetone. Immediately prior to the application time, water was added to each of the above solutions to a total volume of 1300 ml. Also, solutions of a control sample without trial compound were prepared, to which 780 ml of acetone and 520 ml of water were mixed to a total volume of 1300 ml.

The above compositions were applied to cotton by a statistical treatment method with 36 separate areas. Each surface consisted of 4 rows of 20 feet each (about 6.1 meters) and a row spacing of about 3 feet (about 91 centimeters). Each experiment was constructed as a randomized complete block of six different repetitions in which each repetition included: (1) treatment with the control sample without trial compound; (2) Treatment with 0.78 g of compound 44 / area at time T .. designated in Table HH; (3) treatment with 1.55 S of compound 44 / area at time T 1, designated in Table HH; (4) treatment with 3.10 g of Compound 44 per area at time T ^ indicated in Table HH; (5) Treatment with 0.78 g of compound 44 / area at time To », which is indicated in Table HH; (6) Treatment with 3.10 g of compound 44 / area at the point T ₂ designated in Table HH. The above compositions were applied to each area using a carbon dioxide backbone sprayer set at an air pressure of 20 to 40 psig (1.4 to 2.8 kp / cm gauge). Planting, application and harvesting times for cotton plantations are listed in Table HH. For the determination of yield, the harvested cotton of the two middle rows in each area on the middle 10 feet (about 3, o5 m) (in each case 5 feet from the ends of the two Kttelreihen inside) was used. During at least a portion of the growth period, water stress conditions existed to some extent. The values for each area in each repetition were used to calculate the mean to determine the results in Table HH.

Table HH:

Effect of Representative Heterocyclic, Nitrogen-Containing Compounds on Increasing Harvesting - Cotton

Verb concentration application schedule KS (g / area)

Actual yield (g / area)

Control -

0.78

1 ', 55 3,10

0.78 3.10

Flower (T ₁ ) flower ( ¹ I ₁ ) flower (T ₁ )

3 weeks after flowering

984.5

1081.0 1160.4 1175.3

) 1057,8

₂ 3 weeks after flowering (T ") 1065.1

^x First application at flowering (T ₁ ), 47 days after planting; second application three weeks after flowering (T, -,), ⁶⁷ days after planting, and harvest 126 days after planting.

The results in Table HH show that the treatment of cotton with a representative heterocyclic nitrogen-containing compound, i.e., compound 44, by the method of the present invention, gives the crop yield of cotton compared to untreated cotton SEA's under similar conditions considerably improved. Example CLXJtIV:

Effect of Representative Heterocyclic Nitrogen-containing Compounds on Increase in Yield - Sweet Potatoes

The agricultural use of compounds with antiperspirant activity includes not only the saving of water, but also the increase of crop yield. By way of illustration, an antiperspirant compound applied to a fruit can increase actual crop yields by reducing water loss during periods of critical water demand. The increase in crop yield for sweet potatoes used in Table II below was determined according to the following general procedure:

Solutions of Compound 44 were prepared by dissolving 0.78 S, 1.55 g or 3.10 g of the compound in 780 mL of acetone. Immediately prior to the time of application, water was added to each of the above solutions to a final volume of 1300 ml. Also, solutions of a control sample without a trya compound were prepared, including 780 ml of acetone and 520 ml of Was.ser. Total volume of 1300 ml were mixed.

The above compositions were applied to sweet potatoes by a separate patch statistical method. Each area consisted of 4 rows, each 20 feet long and about 3 feet apart. Each experiment was constructed as a randomized, complete block of six different repetitions, each repetition involving: treatment with the control compound without trial compound (1); (2) Treatment with 0.78 g of compound 44 / area at time T ₁ indicated in Table II; (3) treatment with 1.55 g of compound 44 / area at time T ₁ designated in Table II; (4) treatment with 3.10 g of Compound 44 / I at time T ₁ indicated in Table II; (5) Treatment with 0.78 g of compound 44 / area at time T ₂ designated in Table II, and (6) treatment with 1.55 g of compound 44 / area at time T ₂ , which is described in U.S. Pat Table II is designated. The above compositions were applied to each surface with a carbon dioxide backbone sprayer set at an air pressure of 2Q-40 psig (about 1 ^ -8.8 kp / cm gauge). Planting, application and harvesting times · for sweet potato seed sowing are given in table II. In order to determine yield for the harvested sweet potatoes, the yields from the inner 10 feet (approximately 3.05 m) of the two middle rows of each area were taken into account.

scored (5 feet - 1.5 m from the ends of the two center rows). During at least a portion of the growth period there was, to some degree, V / asser stress conditions. The values obtained for the individual areas at the individual repetitions were used to establish the mean values in order to determine the results in Table II.

Table II:

Effect of Representative Heterocyclic Nitrogen-Containing Compounds on Increase in Yield - Sweet Potatoes

Verb concentration application schedule KS (g / area)

Actual yield (kg / area)

Control 44 0.78 1.55 3.10

44 0.78 1.55

95.48

Beginning tuber formation

(T ₁ ) 111.10

Beginning tuber formation

(T ₁ ) 99.88

Beginning tuber formation

(T ₁ ) 99.88

4 weeks after onset of tuber formation (T ₂ ) 107.36 4 weeks after onset of tuber formation (T ₂ ) 98.78

First application at the beginning of tuber formation (T ₁ ), 43 days after transplanting; second application 4 weeks after the onset of tuber formation (T ₂ ), 77 days after transplanting, and harvesting HO days after transplanting. The results in Table II. Demonstrate that the treatment of sweet potatoes with a representative heterocyclic nitrogen containing compound, ie, Compound 44, by the method of the present invention, yields sweet potato compared to untreated sweet potato control plantings under similar conditions considerably increases.

Example CLXXV:

Effect of Representative Heterocyclic, Nitrogenous Compounds on Increasing Harvesting Soybeans

The agricultural use of compounds with antiperspirant activity. includes not only the saving of water, but also the increase in crop yield. By way of illustration, an antiperspirant compound applied to a crop can reduce actual crop yields by reducing water loss during periods of critical water demand. The increase in crop yield of soybeans used in Table JJ below was determined according to the following general procedure:

Solutions of Compound 44 were obtained by dissolution of. 0.78 g, 1.55 g or 3.10 g of compound 44 were prepared in 780 ml of acetone. Immediately prior to the time of application, each of the above solutions was added to Wagser to a final volume of 13P0 ml. Also, solutions of a control sample without trial compound were prepared, to which 780 ml of acetone and 520 ml of water were mixed to a total volume of 1300 ml.

The above compositions were applied to soybeans by a statistical treatment procedure with 36 separate areas. Each surface consisted of 4 rows each 20 feet long (about 6.1 meters) and a row spacing of about 3 feet (about 91 centimeters). Each experiment was constructed as a randotnised, complete block of six different repetitions, each repetition involving: (1) treatment with the control solution without trial compound; (2) Treatment with 1.55 g of Compound 44 / area at time T ₁ indicated in Table JJ; (3) Treatment with 3.10 g of Compound 44 / area at time T ₁ indicated in Table JJ; (4) Treatment with 0.78 g of the compound per area at time Tp indicated in Table JJ.

is net; (5) treatment with 1.55 g of Compound 44 / area at the time! ", Designated iat in Table JJ, and (6) treatment with 3.10 3 of Compound 44 / area at time T ₂ , ^which is indicated ^{in the} table JJ. The above compositions were applied to the individual surfaces with a carbon dioxide backpack sprayer set at an air pressure of 20-40 psig (about 1.4 to 2.8 kp / cm gauge). Planting, application and harvesting times for soybean seeds are given in Table JJ. Yields for the harvested soybeans were taken into account from the inner 10 feet (approximately 3.05 m) of the two middle rows of each surface (5 feet - 1.5 m - each from the ends of the two center rows inward). During at least a portion of the growth period, V / asser stress conditions existed to some extent. The values obtained for the individual areas at the individual repetitions were used for the formation of averages in order to obtain the results in the table JJ. to determine. Table JJ:

Effect of representative heterocyclic nitrogenous compounds on increasing crop yield soybeans

verb , concentration 1.55 Application schedule ^x the Actual He ns (G / area) 3.10 load (kg / area) Control - 0.78 - the 0.48 44 Flower (T ₁ ) 0.55 1.55 Flower (T ₁ ) the 0.55 44 3 weeks after 3.10 Flower (T ₂ ) 0.58 3 weeks after Flower (T ₂ ) 0.60 3 weeks after Flower (T ") 0.52

First application in flower formation (T ₁ ), 63 days after planting; second application 3 weeks after flower formation (T ₂ ), 86 days after planting, and harvest 201 days after planting.

The results in Table JJ show that the treatment of soybean with a representative heterocyclic, nitrogenous compound, i. i.e., compound 44, according to the method of the present invention significantly increases crop yields of soybeans over untreated soybean control soils under similar conditions.

Example ClXJCVI:

Effect of Representative Heterocyclic Nitrogen-Containing Compounds on Increasing Crop Yield - Cotton and Potatoes

The agricultural use of compounds with antiperspirant activity includes not only the saving of water, but also the increase in crop yield. By way of illustration, an antiperspirant compound applied to a crop can increase actual crop yields by reducing water loss during periods of critical water demand. The increase in crop yield of cotton and potatoes used in Tables KIC and LL was determined according to the following general procedure:

An emulsifiable concentrate of compound 44 was prepared containing 39.3 weight percent propylene carbonate, 39.3 weight percent Exxate 700 (Exxon Chemicals, Houston, Texas), 10.0 weight percent Atlox 3455F (ICI Americas , Wilmington, Delaware) and 11.4% by weight of compound 44. Immediately prior to the application time, 31 ml (3.5 g of compound 44) or 62 ml (7.0 g of compound 44) of the above emulsion preparation water was added to a final volume of 3125 ml.

The above compositions were applied to the respective seeding as described in Tables KK and LL according to a statistical treatment method using 30 separate areas. Each surface consisted of 4 rows of 30 feet each with a row spacing of about 3 feet. Each experiment was constructed as a randomized, complete block of six different repetitions, each repetition consisting of the following steps: (1) treatment with a control preparation without a trya compound; (2) Treatment with 3.5 g of compound 44 / area at time T ₁ , which is indicated in Tables KK and LL; (3) treatment with 7.0 g of compound 44 / area at time T, designated in Tables KK and LL; (4) treatment with 3.5 g of Compound 44 / area at time Tp indicated in Tables ICK and LL, and (5 ') treatment with 7.0 g of compound 44 / area at time T ₂ , referred to in Table KK and Table LL. The above compositions were applied to the individual areas. applied to a carbon dioxide backpack sprayer operating at an air pressure of 20-40 .psig

(about 1.4 - 2.8 kgf / cm overpressure) was set. Planting, application and harvesting times for each sowing are given in Tables KK and LL. In order to determine the yield of each unified fruit, the yields were taken into account from the inner 20 feet (approximately 6.1 m) of the two middle rows of each area (5 feet - 1.5 m - in each case from the ends of the two rows of medians). During at least a portion of the growth period, up to one degree of water stress conditions existed. The values determined for the individual areas at the individual repetitions were used for the formation of average values to determine the results in Tables KK and LL.

Table KK:

Effect of Representative Heberocyclic Nitrogen-Containing Compounds on Increasing Crop Yield - Cotton

Verb. Concentration Application Schedule Actual Erliä (g / Area) 'Trag (kg / Area)

Control -

3.5 7.0

3.5 7.0

3.18

2 week flowering (T ₁ ) 3,49 2 weeks before flowering (T.,) 3,48

Flower (T ₂ ) flower (T ₂ )

3.61 3.35

^x first applying two weeks before flowering (T _1), 61 days after planting; second application at flowering (T ₂ ), 73 days after planting, and harvest 167 days after planting.

Table LL:

Effect of Representative Heterocyclic Nitrogen-Containing Compounds on Increasing Harvest - Potatoes

Verb. Concentration application schedule ^x Actual ER- m (g / area). load (kg / area)

Control - 3.5 - the 9 44 7.0 Flower (T ₁ ) 10 3.5 Flower (T ₁ ) the 10 44 3 weeks after 7.0 Flower (T ₂ ) 10 3 weeks after Blossom (To) 9 01 94 23 30 , 87

^X First application at flowering (T ^), 75 days after planting; second application 3 weeks after flowering (T ₂ ), 96 days after planting * and 125 days after planting.

The results in Tables KK and LL show that the treatment of cotton and potatoes with a representative heterocyclic nitrogen-containing compound, i. i.e.,% binding 44, according to the method of the present invention significantly increases crop yields compared to untreated control seeds under similar conditions.

Example CLXXVII:

Effect of Representative Heterocyclic Nitrogen-containing Compounds on Increase in Yield - Soybeans

The agricultural use of compounds with antiperspirant activity includes not only the saving of water, but also the increase in crop yield. By way of illustration, an antiperspirant compound applied to a crop can increase actual crop yields by reducing water loss during periods of critical water demand. The increase in crop yield of soybean used in Table MM below was made according to the following general procedure. determined:

An emulsifiable concentrate of compound 44 was prepared from 39.3% by weight of propylene carbonate, 39.3% by weight of Exxate (Exxon Chemicals, Houston, Texas), 10.0% by weight of Atlox 3455F (ICI Americas, Wilmington, Delaware) and 11.4 μg / volume of compound 44. Immediately prior to the application time, 31 ml (3.5 g of compound 44) or 62 ml (7.0 g of compound 44) of the above-mentioned emulsifiable concentrate V / asser were added to a final volume of 3125 ml. The above compositions were applied to soybeans using a statistical treatment method with 18 separate areas. Each surface consisted of 4 rows of 3P feet each with a 3-foot row spacing (about 91 cm). Each experiment was constructed as a randomized, complete blook of six different repetitions, each repetition consisting of the following steps: (1) treatment with a control preparation without trial compound; (2) treatment with 3.5 g of compound 44 / area at time T ^ designated in Table MM, and (3) treatment with 7.0 g of compound 44 / area at time T ₁ , which is described in U.S. Pat Table MM is designated. The above compositions were applied to each surface with a carbon dioxide backpressure sprayer set at an air pressure of 20-40 psig (about 1.4-2.8 kp / cm gauge). Planting, application and harvesting times for soybean sowing are given in Table MM. Yields for the harvested soybeans were taken into account from the inner 20 feet (approximately 6.1 m) of the two middle rows of each area (each 5 feet - 1.5 m) from the ends of the two center rows inward. During at least a portion of the growth period, water stress conditions existed to some extent. The values determined for the individual areas at the individual repetitions were used for the formation of mean values in order to determine the results in Table MM.

Table MM:

Effect of Representative Heterocyclic Nitrogen-containing Compounds on Increase in Harvest - Soybeans - _

Verb. Concentration Application schedule ^x Actual Er-HS (g / area) _: · load (kg / area)

"Control - - (T ₁ ) / * D , 29 44 3.5 blossom (T ₁ ) 6 , 87 7.0 blossom 6 50

^X First application at flowering (T ₁ ), 48 days after planting, and harvest 186 days after planting.

The results in Table MM show that the treatment of soybeans with a representative heterocyclic, nitrogenous compound, i. i.e., compound 44, according to the method of the present invention, substantially increases the yield of soybeans over untreated control soybean soya beans under similar conditions.

Example CLZXVIII:

Effect of Representative Heterocyclic Nitrogen-containing Compounds on Increasing Harvest Yield - Alfalfa

The effect of representative heterocyclic nitrogenous compounds on increasing crop yield has also been determined for alfalfa according to the following general procedure:

Solutions of compound 44 were prepared by dissolving 6.60 g or 13.20 g of compound 44 in 3300 ml of acetone. Immediately prior to the time of application, water was added to each of the above solutions to a total volume of 5500 ml. Also, solutions of a control sample without trial compound were prepared by mixing 3300 ml of acetone and 2200 ml of water to a total volume of 5500 ml. The above compositions were applied to designated laughs of annual grown alfalfa seeds using a self-propelled chemical sprayer which had an air pressure of 40

2 2

Pound / inch (about 2.8 kp / cm overpressure) was set. Each surface had the following dimensions: 20 feet (30 feet) wide by 30 feet (9.15 meters) in length, Each treatment, including the control surface, consisted of 6 repetitions on 6 separate surfaces. The above compositions were applied 20 days after a cut, the alfalfa was then harvested 28 days after the treatment. For the determination of the yield, the harvested alfalfa from an area of one quarter square meter from the center of each area was taken into account. To some extent, at least during part of the growth period, water stress conditions existed. The values obtained for the individual areas at each repetition were used to obtain the mean value to determine the fourth given in Table M below. Table HII:

Effect of Representative Heterocyclic, Nitrogen-Containing Compounds on Increasing Harvesting - Alfalfa

Verb. M Concentration (g / area) Real earnings Frischgewichf * Z V ¹ X "dry weight Control - 44 6,60 13,20 (g / m ² ) (g / m ² ) 301.2 331.2 342.8 128.2 146.7 153.2

The fresh weight was determined by weighing the alfalfa immediately after harvest.

^xx The dry weight was determined by drying the harvested alfalfa in an oven at 90 ° C for the duration of 24 hours and then weighing the dried alfalfa.

The results in Table MN show that the treatment of alfalfa with a representative herero-cyclic, nitrogen-containing compound, i. h., the compound 44, according to the method of the present invention substantially increases the yield of alfalfa compared to untreated control areas of alfalfa.

Example CLXXIX:

Effect of Representative Heterocyclic Nitrogen-Containing Compounds on Photosynthetic Electron Transport

Since the two Bhotosysteme, d. For example, when photosystems I and II, which are involved in photosynthesis of plants, are interconnected by an electron transport chain, the use of artificial electron donors and acceptors allows the study of specific partial reactions of light reactions of photosynthesis. Following the procedure described by Brewer, PE, Arntzen, CJ and Slife, FW, Weed Science 27: 300-308 (1979), an isolated chloroplast study was used to determine the degree of photosynthetic inhibition caused by the connections mentioned in the tab 00 are caused. In general, the method involves osmotic disruption of isolated pea chloroplasts, introduction of the chloroplasts into a reaction mixture, and the use of methyl viologen as the final electron acceptor. Oxygen consumption was measured with a Clark electrode attached to a Gilson A.uxograph. The results in Table 00 are given as percent inhibition compared to an untreated control.

Table 00:

Effect of Representative Lietero-cyclic, Nitrogen-Containing Compounds on Photosynthetic Electron Transport

Verb. I; a concentration, g / l% ual inhibition (O "uptake)

Control 0 44 622

93 650

Atrazine 108 Diuron 47

The results in Table 00 show that the compounds used in the present invention do not inhibit photosynthetic electron transport, while both atrazine and diuron cause considerable inhibition of photosynthetic electron transport.

Although the invention has been illustrated by the above examples, it is not limited by them; rather, the invention includes the generic range shown above. Various modifications and embodiments may be made without departing from the spirit and scope thereof.

Claims (74)

claims A method for reducing moisture loss of plants characterized by applying to the plant surface an effective amount of a compound sufficient to reduce the loss of moisture from the plant surface without substantially inhibiting the plant's photosynthetic transport of boron, the compound having the formula: : wherein: R _{1 is} a substituted or unsubatituted, 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, or a bridging ring system which may be saturated or unsaturated in which the permissible substituents are the same or different and one or more of the following are hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiozyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxy , Formamidino, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarb onyl, ni tro, cyano group, hydroxy carbonyl and derived salts, formamdio group, alkyl, alkoxy group, polyhaloalkyl, polyhaloalkoxy group, alkoxy carbonyl, substituted amino group in which the permissible substituents are identical or different and one or two of the following are propargyl, alkoxyalkyl, alkylthioalkyl, Alkyl, alkenyl, haloalkenyl or polyhaloalkenyl; Alkylthio, Polyhaloalkylthiogruppe, alkylsulfinyl, Polyhaloaikylsulfinyl, alkylsulfonyl, Polyhaloalkylsulfonyl, A.lkylsulfonylamino-, Alkylkarbonylamino-, Polyhaloaikylsulfonylamino-, Polyhaloalkylkarbonylaminogruppe, trialkylsilyl, aryldialkylsilyl, triarylsilyl sulfonic acid and derivative salts, phosphonic acid and derivative salts, Alkoxykarbonylamino-, Alkylaminokarbonyloxy-, Dialkylaminokarbonyloxygruppe, Alkenyl, polyhaloalkenyl, alkenyloxy group, alkynyl, alkynyloxy, polyhaloalkenyloxy group, polyhaloalkynyl, polyhaloalkynyloxy group, polyfluoroalkanol, cyanoalkylamino group, semicarbazomomethyl, alkoxycarbonylhydrazonomethyl, alkoxyiminomethyl, unsubstituted or substituted aryloxyiminomethyl, hydrazonomethyl, unsubstituted or substituted arylhydrazonomethyl, one condensed with a mono-, di- or polysaccharide Hydroxy, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, aryloxy, aralkoxy, arylthio, aralkylthio, alkylthioalkyl, arylthioalkyl, Arylsulfonyl, arylsulfinyl, haloalkylsulfinyl, haloalkylsulfonyl, Haloalkenybxy-, Haloalkynyloxy-, Haloalkynylthiogruppe, Haloalkenylsulfonyl, Polyhaloalkenylsulfonyl, alkoxysulfonyl, aryloxysulfonyl, propargyloxy, aroyl, Haloazyl, Polyhaloazyl, Aryloxykarbonyl, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, arylaminosulfonyl, Karboxyalkoxy-, Karboxyalkylthio-, Alkoxycarbonylalkoxy, azyloxy, haloazyloxy, polyhaloazyloxy, aroyloxy, alkylsulphonyloxy, alkenylsulphonyloxy, arylsulphonyloxy, haloalkylsulphonyloxy, polyhaloalkylsulphonyloxy, aroylamino, haloazylatnino, alkoxycarbonyloxy, arylsulphonylamino, aminocarbonyloxy, cyanato, isocyanato , Isothiocyanato, cycloalkylamino, trialkylammonium, arylamino, aryl (alkyl) amino, aralkylamino, alkoxyalkylphosphinyl, alkoxyalkylphosphinothioyl, alkylhydroxyphosphinyl, dialkoxyphosphino, hydroxyamino, alkoxyamino, aryloxyamino, aryloxyimino, oxo, thiono, alkylaminoalkoxy, Dialkylaminoalkoxy, alkoxyalkoxy, alkoxyalkenyl, cyanoalkoxy, dialkylsulfonium, -Aj = X, -X = Ro, -
Ϊ1 -X - R ₃ , - or Y ₃ R ₅ -Y ₃ R ₅ ^Y 2 ^R 4 ; or Y ₃ R ₅ R 1 is a substituted heteroatom or a substituted carbon atom or a substituted or unsubstituted, branched or straight chain containing two or more carbon atoms or heteroatoms in any combination, the permissible substituents being the same or different and one or more of the following being hydrogen , Halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthiophenyl, polyb.alalkenyltb.io, thiozyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxy, pormamidino, alkylsulfamido, dialkylsulfamyl , Alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, nitro, cyano, hydroxycarbonyl and derived salts, formamido, alkyl, alkoxy, polyhaloalkyl, polyhaloalkoxy, alkoxycarbonyl, subs a substituted amino group in which the permissible substituents are identical or different and one or two of the following are propargyl, alkoxyalkyl, alkylthioalkyl, alkyl, alkenyl, haloalkenyl or polyhaloalkenyl; Alkylthio, polyhaloalkylthio group, alkylsulfinyl, polyhaloalkylsulfinyl, alkylsulfonyl, polyhaloalkylsulfonyl, alkylsulfonylamino, alkylcarbonylamino, polyhaloalkylsulfonylamino, polyhaloalkylcarbonylamino group, trialkylailyl, aryldialkylsilyly, triarylsilyl, sulfonic acid and derived salts, phosphonic acid and derived salts, alkoxycarbonylamino, alkylaminocarbonyloxy, dialkylaminocarbonyloxy group, Alkenyl, polyhaloalkenyl, alkenyloxy group, alkynyl, alkynyloxy, polyhaloalkenyloxy group, polyhaloalkynyl, polyhaloalkynyloxy group, polyfluoroalkanol, cyanoalkylamino group, semicarbazonomethyl, alkoxycarbonylhydrazonoraethyl, alkoxyiminomethyl, unsubstituted or substituted aryloxyiminomethyl, hydrazonomethyl, substituted or substituted arylhydrazonomethyl, one with a mono-, di- or Polysaccharide condensed hy- droxygruppe, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, aryloxy, aralkoxy, arylthio, aralkylthio, alkylthioalkyl, arylthioalkyl, arylsulfinyl, arylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, haloalkenyl, haloalkynyloxy, haloalkynylthio, haloalkenylsulfonyl, polyhaloalkenylsulfonyl, alkoxysulfonyl , Aryloxysulfonyl, propargyloxy group, aroyl, haloazyl, polyhaloazyl, aryloxycarbonyl, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, arylaminosulfonyl, carboxyalkoxy, carboxyalkylthio, alkoxycarbonylalkoxy, azyloxy, haloazyloxy, polyhaloazyloxy, aroyloxy, alkylsulfonyloxy, alkenylsulfonyloxy, arylsulfonyloxy , Haloalkylsulphonyloxy, polyhaloalkylsulphonyloxy, aroylamino, haloazylamino, alkoxycarbonyloxy, arylsulphonylamino, aminocarbonyloxy, cyanato, isocyanato, isothiozyano, cycloalkylamino, trialkylammonium, arylamino, aryl (alkyl) amino, aralkylamino, alkoxyalkylphosphinyl, Alkoxyalkylphosphinothioyl, alkylhydroxyphspsp hinyl, dialkylaminoalkoxy, dialkoxyphosphino, hydroxyamino, alkoxyamino, aryloxyamino, aryloxyimino, oxo, thiono, alkylaminoalkoxsr, alkoxyalkoxy, alkoxyalkenyl, cyanoalkoxy, dialkylsulfonium, -X - R ₃ , - P - Y ₂ R ₄ , -Y ₄ -P- ^ Y ₃ R ₅ , ' ^Y 3 ^R 5 X is a divalent single 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 the same or and one or more of the following are hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiozyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, formamidino, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl , Hydroxy, amino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylatninothiocarbonyl, diaikylaminothiocarbonyl, nitro, cyano, hydroxycarbonyl and derived salts, formamido, alkyl, alkoxy, polyhaloalkyl, polyhaloalkoxy, Alkoxy carbonyl, substituted amino group, in which the permissible substituents are the same or different and a? or two of the following are propargyl, alkoxyalkyl, alkylthioalkyl, alkyl, alkenyl, haloalkenyl or polyhaloalkenyl; Alkylthio, polyhaloalkylthio group, alkylsulfinyl, polyhaloalkylsulfinyl, alkylsulfonyl, polyhaloalkylsulfonyl, alkylsulfonylamino, alkylcarbonylamino, polyhaloalkylsulfonylamino, polyhaloalkylcarbonylamino group, Trialkylsilyl, aryldialkylsilyl, triarylsilyl SuIfonsäure and derivative salts, phosphonic acid and derivative salts, Alkoxykarbonylamino-, Alkylaminokarbonyloxy-, Dialkylaminokarbonyloxygruppe, alkenyl, Polyhaloalkenyl, alkenyloxy, alkynyl, alkynyloxy, Polyhaloalkenyloxygruppe, Polyhaloalkynyl, Polyhaloalkynyloxygruppe, Polyfluoroalkanol, Zyanoalkylaminogruppe, Semikarbazonomethyl, Alkoxyka'rbonylhydrazonomethyl , Alkoxyiminomethyl, unsubstituted or substituted aryloxyiminomethyl, hydrazonomethyl, unsubstituted or substituted auyliiydrazonomethyl, a hydroxy group condensed with a mono-, di- or polysaccharide, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, aryloxy, aralkoxy, arylthio, aralkylthio, alkylthioalkyl , Arylthialkyl, arylsulfinyl, arylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, haloalkenyloxy, haloalkynyloxy, haloalkynylthio, haloalkenylsulfonyl, polyhaloalkenylsulfonyl, alkoxysulfonyl, aryloxysulfonyl, propargylox ygroup, aroyl, haloazyl, folyhalazyl, aryloxycarbonyl, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, arylaminosulfonyl, carboxyalkoxy, carboxyalkylthio, alkoxycarbonylalkoxy, azyloxy, haloazyloxy, polyhaloazyloxy, aroyloxy, alkylsulfonyloxy, alkenylsulfonyloxy, arylsulfonyloxy, Haloalkylsulfonyloxy, polyhaloalkylsulfonyoxy, aroylamino, haloazylamino, alkoxycarbonyloxy, arylsulfonylamino, aminocarbonyloxy ,. Cyanato, isocyanato, isothiocyanato, cycloalkylamino, trialkylammonium, arylamino, aryl (alkyl) amino, aralkylamino, alkoxyalkylphosphinyl, alkoxyalkylphosphinothioyl, alkylhydroxyphosphinyl, dialkoxyphosphino, hydroxyamino, alkoxyamino, aryloxyamino, aryloxyimino, oxo, thiono , Alkylaminoalkoxy, dialkylaminoalkoxy, alkoxyalkoxy, alkoxyalkenyl, cyanoalkoxy, dialkylsulfonium, D - T T? ¹ V ~ 3 ' -X - R ₃ , - P - X ₂ R ₄ , -X ₄ - P- Y ₂ R ₄ ^Y 3 ^R 5 - / ; and R "is an substituted or unsubstituted heterocyclic ring system having at least one nitrogen atom 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 bridging ring system which may be saturated or unsaturated in which the permissible substituents are identical or different and one or more of the following are hydrogen, halogen, alkylcarbonyl, alkylcarbonyltalkkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiozyano, propargythio, hydroxyimino, alkoxyimino, trialkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxy , ammmamidino, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino, aminocarbonyl, alkylaminocarbonyl, dialkylamino carbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, nitro, cyano, hydroxycarbonyl and derived salts, formate-nido, alkyl, alkoxy, polyhaloalkyl, polyhaloalkoxy, alkoxycarbonyl, substituted amino in which the permissible substituents are the same or different and one or two of the following are propargyl, Alkoxyalkyl, A 1 -thioalkyl, alkyl, alkenyl, haloalkenyl or polyhaloalkenyl; Alkylthio, Polyhaloalkylthiogruppe, alkylsulfinyl, Polyhaloalkylsulfinyl, AlkylsulfQnyl, Polyhaloalkylsulfonyl, alkylsulfonylamino, Alkylkarbonylamino-, Polyhaloalkylsulfonylamino-, Polyhaloalkylkarbonylaminogruppe, trialkylsilyl, aryldialkylsilyl, triarylsilyl, sulfonic acid and phosphoric acid and salts derived salts derived, Alkoxykarbonylamino-, Alkylaminokarbonyloxy-, Dialkylaminokarbonyloxygruppe, alkenyl, Polyhaloalkenyl, alkenyloxy group, alkynyl, alkynyloxy, polyhaloalkenyloxy group, polyhaloalkynyl, polyhaloalkynyloxy group, polyfluoroalkanol, cyanoalkylamino group, semicarbazonomethyl, alkoxycarbonylhydrazonomethyl, alkoxyiminomethyl, unsubstituted or substituted aryloxyiminomethyl, hydrazonomethy], unsubstituted or substituted arylhydrazonomethyl, one having a mono-, di- or poly-acylchard condensed hydroxy, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, aryloxy, aralkoxy, arylthio, aralkylthio, alkylthioalkyl, arylthioalkyl, Arylsulfinyl, arylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, Haloalkenyoloxy-, Haloalkynyloxy-, Haloalkynylthiogruppe, Haloalkenylsulfonyl, Polyhaloalkenylsulfonyl, alkoxysulfonyl, aryloxysulfonyl, propargyloxy, aroyl, Haloazyl, Polyhaloazyl, Aryloxykarbonyl, Atninosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, arylaminosulfonyl, Karboxyalkoxy-, Karboxyalkylthio-, Alkoxykarbonylalkoxy- , Azylosy, haloazyloxy, polyhaloazyloxy, aroyloxy, alkylsulfonyloxy, alenylsulfonyloxy, arylsulfonyloxy, haloalkylsulfonyloxy, polyhaloalkylsulfonyloxy, aroylamino, haloazylamino, alkoxycarbonyloxy, arylsulfonylamino, aminocarbonyloxy, cyanato, isocyanato , Isothiocyanato, cycloalkylamino, trialkylammonium, arylamino, aryl (alkyl) amino, aralkylamino, alkoxyalkylphosphinyl, alkoxyalkylphosphinothio / 1, alkylhydroxyphosphinyl, dialkoxyphosphino, hydroxyamino, alkoxyamino, aryloxyamino, aryloxyimino, oxo, thiono, Alkylaminoalkoxy, dialkylaminoalkoxy, alk oxyalkoxy group, alkoxyalkenyl, cyanoalkoxy group, dialkylsulfonium, Fι f _r X - R ₃ , - P ^ - Y ₂ R ₄ , -Y ₄ -P- Y ₂ R ₄ ^Y 3 ^R 5 ^Y 3 ^R 5 wherein: R is a substituted or unsubstituted, carbocyclic or heterocyclic ring system selected from a monocyclic, aromatic or nonaromatic ring system, a bicyclic, aromatic or non-aromatic ring system, a polycyclic, aromatic or non-aromatic ring system and bridge ring system which may be saturated or unsaturated in which the permissible substituents are the same or different and one or more of the following: hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio , Polyhaloalkenylthio, thiozyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxy, formamidino, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, Alkylaminothiocarbonyl, dialkylaminothiocarbonyl, keto, cyano, hydroxycarbonyl and derived salts, lamidamido, alkyl, alkoxy, polyhaloalkyl, polyhaloalkoxy, alkoxycarbonyl, substituted amino in which the permissible substituents are the same or different and one or two of the following are: propargyl, alkoxyalkyl, alkylthioalkyl, 'alkyl, alkenyl, haloa'lkenyl or polyhaloalkenyl; Alkylthio, Polyhaloalkylthiogruppe, alkylsulfinyl, Polyhaloalkylsulfinyl, alkylsulfonyl, Polyhaloalkylsulfonyl, alkylsulfonylamino, Alkylkarbonylamino-, Polyhaloalkylsulfonylamino-, Polyhaloalkylkarbonylaminogruppe, trialkylsilyl, aryldialkylsilyl, triarylsilyl sulfonic acid and derivative salts, phosphonic acid and derivative salts, Alkoxykarbonylamino-, Alkylaminokarbonyloxy-, Dxalkylaminokarbonyloxygruppe, alkenyl, Polyhaloalkenyl, alkenyoxy group, aynyl, alkyayloxy, polyhaloalkenyloxy group, polyhaloalkynyl, polyhaloalkynyloxy group, polyfluoroalkanol, cyanoalkylamino group, semicarbazonomethyl, alkoxycarbonylhydrazonomethyl, alkoxyiminomethyl, and unsubstituted or substituted aryloxyiminomethyl, hydrazonomethyl, unsubstituted or substituted arylhydrazonomethyl, a mono-, di- or polysaccharide-fused hydroxy group, Haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, aryloxy, aralkoxy ,. Arylthio, aralkylthio, alkylthioalkyl, arylthioalkyl, arylsulfinyl, arylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, Haloalkenyloxy-, haloalkynyl ^ oxy, Haloalkynylthiogruppe, Haloalkenylsulfonyl, PoIyhaloalkenylsulfonyl, Alkoxysulfonyl, aryloxysulphonyl, propargyloxy, aroyl, Haloazyl, Polyhaloazyl, Aryloxykarbonyl, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl , Arylaminosulfonyl, carboxyalkoxy, carboxyalkylthio, alkoxycarbonyloxy, azyloxy, halo-azyloxy, polyhalo-azyloxy, aroyloxy, alkylsulfonyloxy, alkenylsulfonyloxy, arylsulfonyloxy, haloalkylsulfonyloxy, polyhaloalkylsulfonyloxy, aroylamino, haloazylamino, alkoxycarbonyloxy, arylsulfonylamino , Aminocarbonyloxy, cyanato, isocyanato, isothiocyanato, cycloalkylamino, trialkylammonium, arylamino, aryl (alkyl) amino, aralkylamino, alkoxyalkylphosphinyl, alkoxyalkylphosphinothioyl, alkylhydroxyphosphinyl, dialkylaminoalkoxy, dialkoxyphosphino, hydroxyamino, alkoxyamino, aryoxyamine o-, aryloxyimino, oxo, thiono, alkylaminoalkoxy, alkoxyalkoxy, alkoxyalkenyl, cyanoalkoxy, dialkylsulfonium, -X - R ₃ , - P - X ₂ R ₄ , -Y ₄ -P- ^Y 2 ^R 4 , or Y, R _C S is a substituted heteroatom or a substituted carbon atom or a substituted or unsubstituted, branched or straight chain containing two or more carbon atoms or heteroatoms in any combination, the permissible substituents being the same or different and one or more of the following: hydrogen , Halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiozyano, pr'opargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxy, JOrmamidono, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, Hydroxy, amino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, nitro, cyano, hydroxycarbonyl and derivative salts, pormamido, alkyl, alkoxy, polyhaloalkyl, polyhaloalkoxy, alkoxycarbonyl, substituents amino group in which the permissible substituents are identical or different and one or two of the following: propargyl, alkoxyalkyl, alkylthioalkyl, alkyl, alkenyl, haloalkenyl or polyhaloalkenyl; Alkylthio, Polyhaloalkylthiogruppe, alkylsulfinyl, Polyhaloalkylsulfinyl, alkylsulfonyl, Polyhaloalkylsulfonyl, alkylsulfonylamino, Alkylkarbonylamino-, Polyhaloalkylsulfonylamino-, PoIyhaloalkylkarbonylaminogruppe, trialkylsilyl, aryldialkylsilyl, triarylsilyl sulfonic acid and derivative salts, phosphonic acid and derivative salts, Alkoxykarbonylamino-, Alkylaminokarbonyloxy-, Bialkylaminokarbonyloxygruppe, alkenyl, Polyhaloalkenyl, alkenyloxy group, alkynyl, alkynyloxy, polyhaloalkenyloxy group, polyhaloalkynyl, polyhaloalkynyloxy group, polyfluoroalkanol, cyanoalkylamino group, semicarbazonomethyl, alkoxycarbonylhydrazonomethy], alkoxyiminomethyl, unsubstituted or substituted aryloxyiminomethyl, hydrazonomethyl, unsubstituted or substituted arylhydrazonomethyl, one with a mono-, di-, or polysaccharide condensed hydroxy group, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, aryloxy, aralkoxy, arylthio, aralkylthio, alkylthioalkyl, arylthioal kyl, arylsulfonyl, arylsulfinyl, haloalkylsulfinyl, haloalkylsulfonyl, haloalkenybxy, haloalkynyloxy, haloalkynylthio, haloalkenylsulfonyl, polyhaloalkenylsulfonyl, alkoxysulfonyl, aryloxysulfonyl, propargyl '. aroyl, haloazyl, polyhaloazyl, aryloxycarbonyl, aminosulphonyl, alkylaminoaulfonyl, dialkylsminosulphonyl, arylaminosulphonyl, carboxyalkoxy, carboxyalkylthio, alkoxycarbonylalkoxy, azyloxy, halooxynxy, polyhaloazyloxy, aroyloxy, alkylsulphonyloxy, alkenylsulphonyloxy, arylsulphonyloxy, haloalkylsulphonyloxy , Polyhaloalkylsulfonyloxy, aroylamino, haloazylamino, alkoxycarbonyloxy, arylsulfonylamini-, amino- karbonyloxy, cyanato, isocyanato, isothiocyanato, cycloalkylamino, trialkylammonium, arylamino, aryl (alkyl) amino, aralkylamino, alkoxyalkylphosphinyl, alkoxyalkylphosphinothioyl, alkylhydroxyphosphinyl, dialkoxyphosphino, hydroxyamines, alkoxyamino, aryloxyamino, aryloxyimino, oxo , Thiono, alkylaminoalkoxy, dialkylaminoalkoxy, alkoxyalkoxy, alkoxyalkenyl, cyanoalkoxy, dialkylsulfonium, -X, = X, -X = R ₃ , = XR ₃ ,
Y " -XR ₃ , -P ^ - Y ₂ R ₄ , -Y ₄ - P ^ - Y ^ R
or ₂ R ₄ ^YR Y.J and Υ "are independently oxygen or sulfur; Y ₂ and Yo are independent of any oxygen, sulfur, an amino group or a divalent bond and R. and independently of one another are hydrogen or substituted or unsubstituted alkyl, polyhaloalkyl, phenyl or benzyl, the permissible substituents being identical or different and one or more of the following: hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiozyano-, Propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxy, pormamidino, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, methyl, cyano, Hydroxy carbonyl and derivative salts, pormamido group, alkyl, alkoxy group, polyhaloalkyl, polyhaloalkoxy group, alkoxycarboxylyl, substituted amino group in which the permissible substituents are the same or different and one or two of the following: Prop argyl, alkoxyalkyl, alkylthioalkyl, alkyl, alkenyl, haloalkenyl or polyhaloalkenyl; Alkylthio, Polyhaloelkylthiogruppe, alkylsulfinyl, Polyhaloalkylsulfinyl, alkylsulfonyl, Polyhaloalkylsulfonyl, Alkylsulfonylaminor, Alkylkarbonylamino-, Polyhaloalkylsulfonylamino-, Polyhaloalkylkarbonylaminogruppe, trialkylsilyl, aryldialkylsilyl, tri-r arylsilyl, sulfonic acid and salts derived Phosphonsäüre and salts derived, Alkoxykarbonylamino-, Alkylaminokarbonyloxy-, Dialkylaminokarbonyloxygruppe, Alkenyl, polyhaloalkenyl, alkenyloxy group, alkynyl, alkynyloxy, polyhaloalkenyloxy group, polyhaloalkynyl, polyhaloalkynyloxy group, polyfluoroalkanol, cyanoalkylamino group, semicarbanzonomethyl, alkoxycarbonylhydrazonomethyl, alkoxyiminomethyl, unsubstituted or substituted aryloxyiminomethyl, hydrazonotethyl, unsubstituted or substituted arylhydrazonomethyl, one condensed with a mono-, di- or polysaccharide Hydroxy, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, aryloxy, aralkoxy, arylthio, aralkylthio, alkylthioalkyl, arylthio alkyl, arylsulfinyl, arylsulfonyl, Haloalkylsulfinyl, haloalkylsulfonyl, Haloalkenyloxy-, Haloalkynyloxy-, Haloalkynylthiogi-oup, Haloalkenylsulfonyl, Polyhaloalkenylsulfonyl, alkoxysulfonyl, Arytoxysulfonyl, propargyloxy, aroyl, Halazyl, Polyhaloazyl, Aryloxykarbonyl, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, arylaminosulfonyl, Karboxyalkoxy-, Karboxyalkylthio- ,. Alkoxycarbonylalkoxy, azyloxy, haloazyloxy, polyhaloacyloxy, aroyloxy, alkylsulfonyloxy, alkenylsulfonyloxy, arylsulfonyloxy, haloalkylsulfonyloxy, polyhaloalkylsulfonyloxy, aroylamino, haloazylamino, alkoxycarbonyloxy, arylsulfonylamino, aminocarbonyloxy, cyanato, isocyanatoisothiozyano , Cycloalkylamino, trialkylammonium, arylamino, aryl- (alkyl) amino, aralkylamine, alkoxyalkylphosphinyl, alkoxyalkylphosphinothioyl, alkylhydroxyphosphinyl, dialkoxyphosphino, hydroxyamines, alkoxyamino, aryloxyamino, aryloxyimino, oxo, thiono, alkylaminoalkoxy, , Dialkylaminoat oxy group, alkoxyalkenyl, Zyanoalkoxygruppe, dialkylsulfonium, -X, = X, -X = R ₃ , = XR ₃ , 2. The method according to claim 1, characterized in that R ₁ and R_ are independently a substituted or unsubatituiertes, carbocyclic or heterozykliaches Ringaystem which is selected from a mono cyclic aromatic or non-aromatic ring system with the
formula a bicyclic aromatic or non-aromatic ring system having a formula selected from -X - R ₃ , - PY ₂ R ₄ , -Y ₄ - Y ₃ R ₅ Y ₂ R ₄ Y ₃ R ₅ a polycyclic aromatic or non-aromatic ring system having a formula selected from ζ ζ i / 7 Z Z II) ^A ₇ and a bridged ring sateem which may be saturated or unsaturated and has a formula selected from and 12 ^A 13 ^A 12 Z Z wherein,:. A _{1 represents} a ring-forming chain of atoms which, together with B _{1, form} a carbocyclic or heterocyclic. Form ring system containing between 0 and 4 double bonds or between 0 and 2 triple bonds; B _{1 represents} a saturated or unsaturated carbon atom; and A, independently of each other, form a ring-forming chain of Represent atoms which, together with B "and B, represent a carbocyclic or heterocyclic ring system; B "and B are independently a saturated or unsaturated carbon atom or a saturated nitrogen atom; A., Ar, Ag and A "independently represent a ring-forming chain of atoms which together with B., B, -, Bg and B" form a carbocyclic or heterocyclic ring system; B., Bp, Bg and B "independently represent a saturated or unsaturated carbon atom or a saturated nitrogen atom; Ag, Ag and A.JQ independently represent each other a ring-forming chain of atoms which together with Bg, B_ and B ₁₀ , B ^ _{1 form} a carbocyclic or heterocyclic ring system; and independently of one another a saturated or Bo »Bq unsaturated carbon atom or a saturated nitrogen atom; B _{11 represents} a saturated or unsaturated carbon, nitrogen or phosphorus atom; A ₁₁ , A .. £ and A ₁ ^ independently represent a ring-forming chain of atoms which together with B ^ and B ₁ ^ form a carbocyclic or heterocyclic ring system; Β., £ and are independently a saturated carbon atom or a nitrogen atom, and Z is the same or different and one or more of the following is hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiozyano, propargylthio, hydroxyimino, alkoxyimino, tri-alkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxy, formamidino , Alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxy-sulfonyl, hydroxy, amino, atninocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, nitro, cyano, hydroxycarbonyl and derived salts, imomamido, alkyl, alkoxy, polyhaloalkyl, polyhaloalkoxy, alkoxycarbonyl, substituted amino group in which the permissible substituents are the same or different and one or two of the following: propargyl, alkoxyalkyl, alkylthioalkyl, alkyl, alkenyl, haloalkenyl or polyhaloalkenyl; Alkylthio, Polyhaloalkylthiogruppe, alkylsulfinyl, Polyhaloalkylsulfinyl, Alkylaulfonyl, PoIyhaloalkylsulfonyl, alkylsulfonylamino, Alkylkarbonylamino-, Polyhaloalkylsulfonylamino-, Polyhaloalkylkarbonylaminogruppe, trialkylsilyl, aryldialkylsilyl, triarylsilyl sulfonic acid and derivative salts, phosphonic acid and derivative salts, Alkoxykarbonylamino-j Alkylaminokarbonyloxy-, Dialkylaminokarbonyloxygruppe, alkenyl, Polyhaloalkenyl, alkenyloxy group, alkynyl, alkynyloxy, polyhaloalkenyloxy group, polyhaloalkynyl, polyhaloalkynyloxy group, polyfluoroalkane, cyanoalkylamino group, semicarbazonomethyl, alkoxycarbonylhydrazonomethyl, alkoxyiminomethyl, unsubstituted or substituted aryloxyiminomethyl, hydrazonomethyl, unsubstituted or substituted aryl-hydrazonometh.yl, one with a mono-, di- or polysaccharide condensed hydroxy group, haloalkyl, halo alkenyl, haloalkynyl, alkoxyalkyl, aryloxy, aralkoxy, arylthio, aralkylthio, alkylthioalkyl, arylthioalkyl, arylsulfinyl, arylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, haloalkenyloxy, haloalkynyloxy, haloalkynylthio, haloalkenylsulfonyl, polyhaloalkenylsulfonyl, alkoxysulfonyl, aryloxysulfonyl, propargyloxy, aroyl, Haloazylin, polyhaloazyl, aryloxycarbonyl, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, arylaminosulfonyl, karoxyalkoxy, carboxyalkylthio, alkoxycarbonylalkoxy, azyloxy, haloazyloxy, polyhaloazyloxy, aroyloxy, alkylsulfonyloxy, alkenylsulfonyloxy, arylsulfonyloxy, haloalkylsulfonyloxy, polyhaloalkylsulfonyl oxy, aroylamino, haloazylimino, alkoxycarbonyloxy, arylsulfonylamino, aminocarbonyloxy, cyanato, isocyanato, tothiozyano, cycloalkylamino, trialkylammonium, arylamino, aryl (alkyl) amino, aralkylamino, alkoxyalkylphosphinyl, alkoxyalkylphosphinothioyl, hydroxyamino, Alkoxyamino, dialkylami- alkoxy group, alkylhydroxyphosphinyl, dialkoxyphosphino, aryloxyamino, arlyoxyimino, oxo, thiono, alkylaminoalkoxy, alkoxyalkoxy, alkoxyalkenyl, cyanoalkoxy, dialkylsulfonium, X-y -tr Tj Ύ "Ό Y ₁ Y ₁ • I ¹ II ¹ -X - R ₃ , -P -Y ₂ R ₄ , -Y ₄ -P- Y ₃ R ₅ ^Y 2 ^R 4 ^Y 3 ^R 5 wherein R 1, R ₄ , R 1, Y 1, Y ₂ , Y ₃ , Y ₄ and X are as defined in claim 1. 3. The method according to claim 1, characterized in that the compound has the following formula: wherein Ri is the same or different and one or more of the following is hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiozyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxyt, formamidino , Alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothipcarbonyl, alkylarainothiocarbonyl, dialkylaminothiocarbonyl, nitro, cyano, hydroxycarbonyl and derived salts, formamidino, alkyl, alkoxy, polyhaloalkyl, polyhaloalkoxy, alkoxycarbonyl, substituted amino group in which the permissible substituents are the same or different and one or two of the following: propargyl, alkoxyalkyl, alkylthioalkyl, alkyl, alkenyl, haloalkenyl or polyhaloalkenyl; Alkylthio, polyhaloalkylthio group, alkylsulfinyl, polyhaloalkylsulfinyl, Alkylsulfonyl, Polyhaloalkylsulfonyl, alkylsulfonylamino, Alkylkarbonylamino-, Polyhaloalkylsulfonylamino-, PoIyhaloalkylkarbonylaminogruppe, trialkylsilyl, aryldialkylsilyl, triarylsilyl, sulfonic acid and salts derived, phosphonic acid and derivative salts, Alkoxykarbonylatnino-, Alkylaminokarbonyloxy-, Dialkylaminokarbonyloxygruppe, alkenyl, Polyhaloalkenyl, alkenyloxy, alkynyl, alkynyloxy-j Polyhaloalkenyloxy group, polyhaloalkynyl, polyhaloalkynyloxy group, polyfluoroalkanol, cyanoalkylamino group, semicarbazonomethyl, alkoxycarbonylhydrazonomethyl, alkoxyiminomethyl, unsubstituted or substituted aryloxyiminomethyl, hydrozonomethyl, unsubstituted or substituted arylhydraBonomethyl, a mono-, di- or polysaccharide-fused hydroxy group, haloalkyl, haloalkenyl, haloalkynyl, alkoxy .alkyl, aryloxy, aralkoxy, arylthio, aralkyl, alkylthioalkyl, arylthioalkyl, arylsulfinyl, arylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, haloalk enyloxy-, Haloalkynyloxy-, Haloalkynylthiogruppe, Haloalkenylsulfonyl, Polyhaloalkenylsulfonyl, Alkoxyaulfonyl, aryloxysulfonyl, Propprgyloxygruppe, aroyl, Haloazyl, Polyhaloazyl, Aryloxykarbonyl, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, arylaminosulfonyl, Karboxyalkoxy-, Karboxyalkylthio-, Alkoxykarbonylalkoxy-, Azyloxy-, HaIoazyloxy-, Polyhaloazyloxy , Aroyloxy, alkylsulfonyloxy, alkenylsulfonyloxy, arylsulfonyloxy, haloalkylsulfonyloxy, polyhaloalkylsulfonyloxy, aroylamino, haloazylamino, alkoxycarbonyloxy, arylsulfonylamino, aminocarbonyloxy, cyanato, isocyanato, isothiozyano, cycloalkylamino, trialkylammonium, arylamino, , Aryl (alkylamino, aralkylamino, alkoxyalkylphosphino), alkoxyalkylphosphino, alkylhydroxyphosphinyl, dialkoxyphosphino, hydroxyamino, alkoxyamino, aryloxyamino, aryloxyimino, oxo, thiono, alkylaminoalkoxy, dialkylaminoalkoxy, alkoxyalkoxy, alkoxyalkenyl, cyanoalkoxy, dialkylsulfonium, -X, = X, -X = R ₃ , = XR ₃ , -X - R ₃ , - PY ₂ R ₄ , -Y ₄ - PY ₂ R ₄ ^Y 3 ^R 5 or X, O, S, SO, SO _2, J NH, CH ₂ , CO, a single bivalent bond, GH ₂ O, CHgS, -CH (CH ₃ ) O, -CH (CN) O-, -CH = HO- , -C (CH ₃ ) = NO-, -CH ₂ CH ₂ O-, -CH ₂ CH ₂ -, -C = C-, -CH ₂ SO-, -CH ₂ SO ₂ - -OCH ₂ CH ₂ O -, -CH (alkyl) - or -CONH- are and Y ^ and Y | independently of one another are halogen, alkyl or an alkoxy group, wherein X, R ₃ , R ₄ , R ₅ ,
Finished are. Y ₂ Y ₃ and Y ₄ as defined in claim 1 4. The method according to claim 1, characterized in that the compound has the following formula: ^Y 3 wherein: R 1 and R 'are identical or different and R 1 is one or more of the following: hydrogen, halogen, alkylcarbonyloxy, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiozyano, propargylthio, hydroximino, alkoxyimino, trialkylsilyloxy , Aryldialkylsilyloxy, triarylsilyloxy, imomamidino, alkylsulfamido, dialkylaulamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino, aminocarbonyl. Alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, nitro, cyano, hydroxycarbonyl and derived salts, lmmamido group, alkyl, alkoxy group, polyhaloalkyl, polyhaloalkyl, polyhaloalkoxy group, alkoxycarbonyl, substituted amino group in which the permissible substituents are the same or different and one or two of the following are / propargyl, alkoxyalkyl, alkylthioalkyl, alkyl, alkenyl, haloalkenyl or polyhaloalkenyl; Alkylthio, polyhaloalkylthio group, alkylsulfinyl, polyhaloalkylsulfinyl, alkylsulfonyl, polyhaloalkylsulfonyl, alkylsulfonylamino, alkylcarbonylamino, polyhaloalkylsulfonylamino, polyhaloalkylcarbonylamino, trialkylsilyl, aryldialkylsilyl,. Triarylsilyl, sulfonic acid and derived salts, phosphonic acid and derived salts, alkoxycarbonylamino, alkylaminocarbonyloxy, dialkylaminocarbonyloxy, alkenyl, polyhaloalkenyl, alkenyloxy, alkynyl, alkynyloxy, , Plyhaloalkenyloxy group, polyhaloalkynyl, polyhaloalkynyl group, polyfluoroalkanol, cyanoalkylamino group, semicarbazonomethyl, alkoxycarbonylhydrazonomethyl, alkoxyiminomethyl, unsubstituted or substituted aryloxyiminomethyl, hydrazonomethyl, unsubstituted or substituted arylhydrazonomethyl, a hydroxyl group condensed with a mono-, di- or polysaccharide, halo alkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, * aryloxy, aralkoxy, arylthio, aralkylthio, · alkylthioalkyl, arylthioalkyl, arylsulfinyl, Ärylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, Haloalkenyloxy-, Haloalkynyloxy-, Haloalkynylthiogruppe, Haloalkenylsulfonyl, PoIyhaloalkenylsulfonyl, Alkoxysulfonyl, aryloxysulphonyl, propargyloxy , Aroyl, haloazyl, polyhaloazyl, aryloxycarbonyl, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyi, arylaminesulfonyl, carboxyalkoxy, carboxyalkylthio, alkoxycarbonylalkoxy, azyloxy, haloazyloxy, polyhaloazyloxy, aroyloxy, alkylsulfonyloxy, alkenylsulfonyloxy, arylsulfonyloxy, haloalkylsulfonyloxy, Polyhaloalkylsulfoyloxy, aroylamino, haloazylamino, alkoxycarbonyloxy, arylsulfonylamino, aminocarbonyloxy, cyanato, isocyanato, isothiozyano, cycloalkylamino, trialkylammonium, arylamino, aryl (alkyl) amino, aralkylamino, alkoxyalkylphosphinyl, alkoxy alkylphosphinothioyl, alkylhydroxyphosphinyl, dialkoxyphosphino, hydroxyamino, alkoxyamino, aryloxyamino, aryloxyimino, oxo, thiono, alkylaminoalkoxy, dialkylaminoalkoxy, alkoxyalkoxy, alkoxyalkenyl, cyanoalkoxy, dialkylsulfonium,
^Y 1 ^Y 1 Y ₃ R ₅ Y ₃ R ₅ or ^Y 2 ^R 4
Y ₃ R ₅ Xi east, S, SO, SO _2, HH, GH _2, CO, a single divalent bond, -CH (CH ₃₎ O-, -CH (CW) O-, (-CH = NO-, -C CH ₃ ) = NO-, CH ₂ CH ₂ O-, -C = C-, -CH ₂ SO-, -CH ₂ SO ₂ -, -OCH ₂ CH ₂ O-, -CH (alkyl) - or -COMH- and Yl is halogen, wherein X, R ₃ , R, R 1, Y 1, Y ₂ , Y ₃ and Y are as defined in claim 1. A method according to claim 1, characterized in that the compound has the following formula wherein: RS, Rl and R ^ are the same or different and R '. one or more of the following is hydrogen, halogen, alkylcarbonyl, alkylcarbonylacyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiozyano, propargylthio, hydroxyimino, alkoxyimino,! crialkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxy, formamidino, alkylsulfamido , Dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino, aminocarbonyl, alkylaminokaibonyl, dialkylaminocarbonyl, aminothiocarbonyl 1, alkylaminothiocarbonyl, dialkylaminofiocarbonyl, nitro, cyano, hydroxycarbonyl and derivative salts, formamidoalkyl, alkoxy, polyhaloalkyl, polyhaloalkoxy, alkoxycarbonyl, substituted amino, in the permissible substituents are the same or different and one or two of the following: propargyl, alkoxyalkyl, alkylthialkyl, alkyl, alkenyl, haloalkenyl or polyhaloalkenyl; Alkylthio, polyhaloalkylthio, alkylsulfinyl, polyhaloalkylsulfinyl, alkylsulfonyl, polyhaloalkylsulfonyl, alkylsulfonylamino, alkylcarbonylamino, polyhaloalkylsulfonylamino, polyhaloalkylcarbonylamino, trialkylsilyl, aryldialkylsilyl, triarylsilyl, sulfonic and derived salts, phosphonic and derived salts, alkoxycarbonylamino, alkylaminocarbonyloxy, dialkylaminocarbonyloxy , alkenyl, Polyhaloalkenyl, alkenyloxy, alkynyl, alkynyloxy _s PoIyhaloalkenyloxygruppe, Polyhaloalkynyl, Polyhaloa \ lkynyl- oxygruppe, Polyfluoroalkanol, Zyanoalkylaminogruppe, Semikarfcazonomethyl, Alkoxykarbonylhydrazonomethyl, alkoxyiminomethyl, unsubstituted or substituted aryloxyiminomethyl, hydrazonomethyl, unsubstituted or substituted arylhydrazonomethyl, one condensed with a mono-, di- or Ppossaocharid hydroxy group, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, aryloxy, aralkoxy , arylthio, aralkylthio, alkylthioalkyl, Arylthialkyl, arylsulfinyl, arylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, HaloalkenyJbxy-, Haloalkynyloxy-, Haloalkynylthiogruppe, Haloalkenylsulfonyl, Polyhaloalkenylsulfonyl, alkoxysulfonyl, aryloxysulfonyl, propargyloxy, aroyl, Haloazyl, Polyhaloazyl, Aryloxykarbonyl, aminosulfonyl, alkylaminosulfonyl, DialkylaminosuEonyl, Arylaminosulfonyl, carboxyalkoxy, carboxyalkylthio, alkoxycarbonylalkoxy, azyloxy, haloazyloxy, polyhaloazyloxy, aroyloxy, alkylsulfonyloxy, alkenylsulfonyloxy, arylsulfonyloxy, haloalkylsulfonyloxy, and the like lyhaloalkylsulfonyloxy, aroylamino, haloazylamino, alkoxycarbonyloxy, arylsulfonylamino, aminocarbonyloxy, cyanato, osizyanato, isothiozyano, cycloalkylamino,, trialkylammonium, arylamino, aryl (alkyl) amino, aralkylamino, alkoxyalkylphosphinyl, alkoxyalkylphosphino. thioyl, alkylhydroxyphosphinyl, dialkoxyphosphino, hydroxyamino, alkoxyamino, aryloxyamino, aryloxyimino, oxo, TÜiono, Alkylatninoalkoxy-, dialkylaminoalkoxy, alkoxyalkoxy, alkoxyalkenyl, cyanoalkoxy, dialkylsulfonium, or y ^Y 2 ^R 4
--- C; and • ^Y 3 ^R 5 X'O, S, SO, SO ₂ , NH, CH ₂ , CO, a single bivalent bond, -CH (CH ₃ ) O-, -CH (CN) O-, -CH = NO-, -C (CH ₃ ) = NO-, -CH ₂ CH ₂ O-, -C = C-, -CHgSO-, -CHgSOg-, -OCH ₂ CH ₂ O-, -CH (alkyl) - or -CONH-, wherein X, R ₃ , R, R _g ,
are defined. Y ₃ and Y. as in claim 1 6. The method according to claim 1, characterized in that the compound has the formula: wherein: Y 1, Y 1, Y 1, Y 1 and Y 3 are identical or different and the following are: halogen, hydrogen, alkyl kibonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiozyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy , Aryldialkylsilyloxy, triarylsilyloxy, e-amidamido, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, nitro, cyano, hydroxycarbonyl and derived salts, formamido, alkyl, Alkoxy group, polyhaloalkyl, polyhaloalkoxy group, alkoxycarbonyl, substituted amino group in which the permissible substituents are the same or different and one or two of the following: propargyl, alkoxylalkyl, alkylthioalkyl, alkyl, alkenyl, haloalkenyl or polyhaloalkenyl; Alkylthio, polyhaloalkylthio group, alkylsulfinyl, polyhaloalkylsulfinyl, alkylsulfonyl, polyhaloalkylsulfonyl, alkylsulfonylamino, alkylcarbonylamino, polyhaloalkylsulfonylamino, polyhaloalkylcarbonylamino, trialkylsilyl, aryldialkylsilyl, triarylsilyl, sulfonic acid and derived salts, phosphonic acid and derived salts, alkoxycarbonylamino, alkylaminocarbonyloxy , Dialkylaminocarbonyloxy, alkenyl, polyhaloalkenyl, alkenyloxy, alkynyl, ABcynyloxy, polyhaloalkenyloxy, polyhaloalkynyl, polyhaloalkynyloxy, polyfluoroalkanol, cyanoalkylamino, seraikarbazonomethy, alkoxycarbonylhydrazonomethyl, alkoxyiminomethyl, unsubstituted or substituted aryloxyiminotethyl, hydrazonomethyl, unsubstituted or substituted arylhydrazonomethyl, one with a mono-, di or polysaccharide fused hydoxy, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, aryloxy, aralkoxy, arylthio, aralkylthio, alkylthioalkyl, arylthio lkyl, arylsulfinyl, arylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, Haloalkenyloxy-, Haloalkynyloxy-, Haloalkynylthiogruppe, Haloalkenylsulfonyl, Polyhaloalkenylsulfonyl, Alkoxysulf onyl, aryloxysulfonyl, propargyloxy, aroyl, Haloazyl, Polyhaloazyl, Aryloxykarbonyl, Atninosulfonyl, Alkylatninosulfonyl, dialkylaminosulfonyl, Arylatninosulfonyl, Karboxyalkoxy-, Karboxyalkylthio- , Alkoxycarbonylalkoxy, azyloxy, haloalkyloxy, polyhaloazyloxy, aroyloxy, alkylsulphonyloxy, alkenylsulphonyloxy, arylsulphonyloxy, haloalkylsulphonyloxy, polyhaloalkylsulphonyloxy, aroylamino, haloazylamino, alkoxycarbonyloxy, arylsulfonylamino, aminocarbonyloxy, cyanato, Isocyanato, isothiocyanato, cycloalkylamino, trialkylammonium, arylamino, aryl (alkyl) amino, aralkylaraino, alkoxyalkylphosphinyl, alkoxyalkylphosphinothioyl, alkylhydroxyphosphinyl, dialk. oxyphosphino, hydroxyamino, alkoxyamino, aryloxyaralno, aryloxyimino, oxo, thiono, alkylaminoalkoxy, dialkylaminoalkoxy, alkoxyalkoxy, alkoxyalkenyl, cyanoalkoxy, dialkylsulfonium, -X, = X, -X = Rt) = X-Ro, worm: -XR ₃ - P- Y ₂ R ₄ , -Y ₄ - P ^ - Y ₂ R ₄ Y ₃ R ₅ Y ₃ R ₅ or Y ₃ R ₅ Y 'Yl ₀ , YIj ₁ and YiJ _{2 are the} same or different and are hydrogen, halogen, alkyl, polyhaloalkyl, a cyano group or aryl; m 'and n' are the same or different and have a value of ο to 5; X is O, S, SO, SO ₂ , NH, CH ₂ , CO, a single bivalent bond, -CH (CH ₃ ) O-, -CH (CN) O-, -CH = NO-, -C (CH ₃ J = NO, -CH ₂ CH ₂ O-, -C = C-, -CH ₂ SO-, -CH ₂ SO ₂ -, -OCH ₂ CH ₂ O-, -CH (allcyl) - or -CONH - is and Ϋ »and Yi. are the same or different and are halogen, alkyl or an alkoxy group, wherein X, R ₃ , R ₄ , H ₅ , Y ₁ , Y ₂ , Y ₃ and Y _{4 are} as defined in claim 1. 7. The method according to claim 1, characterized in that the compound has the following formula:  ΐ N_ Yl, Yi, Y, Y and Y are the same or different and the following are: hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiozyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxy -, Formamidlno-, Alkylsul- £ amido, Dialkylsulfymido-, alkoxysulfonyl, PoIyhaloalkoxysulfonyl, hydroxy, amino, Aminokarbonyl, Alkylaminokarbonyl, Dialkylaminokarbonyl, Aminothiokarbonyl, Alkylaminothiokarbonyl, Dialkylaminothiokarbonyl, nitro, cyano group Hydroxykarbonyl and derived salts, formamido, alkyl, alkoxy Polyhaloalkyl, polyhaloalkoxy group, alkoxycarbonyl, substituted amino group in which the permissible substituents are the same or different and one or two of the following: propargyl, alkoxyalkyl, alkylthioalkyl, alkyl, alkenyl, haloalkenyl or polyhaloalkenyl; Alkylthio, polyhaloalkyl thio, alkylsulfinyl, Polyhaloalkylsulfinyl, alkylsulfonyl, Polyhaloalkylsulfonyl, alkylsulfonylamino, Alkylkarbonylamino-, Polyhaloalkylsulfonylamino-, Polyhyloalkylkarbonylaminogruppe, trialkylsilyl, Aryldialkylsi-yi, Triarylsxlyl, sulfonic acid and salts derived, phosphonic acid and derivative salts, Alkoxykarbonylamino-, Alkylaminokarbonyloxy-, Dialkylaminokarbonyloxygruppe , Alkenyl, polyhaloalkenyl, alkenyloxy group, alkynyl, alkynyloxy, polyhaloalkenyloxy group, polyhaloalkynyl, poly- IO m ' haloalkynyloxy group, polyfluoroalkanaol, cyanoalkylamino group, semicarbazonomethyl, alkoxycarbonylhydrazonomethylj alkoxyiminomethyl, unsubstituted or substituted aryloxyiminomethyl, hydrazonomethyl, unsubstituted or substituted arylhydrazonomethyl, a mono-, di- or polysaccharide-fused hydroxy group, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, aryloxy, aralkoxy, arylthio, aralkylthio, alkylthioalkyl, arylthioalkyl, arylsulfinyl, arylsulfonyl, Haloalkylsulf ynyl, haloalkylsulfonyl, Haloalkenyloxy-, HaIoalkynyloxy-, Haloalkynylthiogruppe, Haloalkenylsulfonyl, Polyhaloalkenylsulfonyl, alkoxysulfonyl, aryloxysulfonyl, Propargyloiygruppe, aroyl, Haloazyl, Polyhaloazyl, Aryloxykarbonyl, aminosulfonyl, Alkylatninosulfonyl, dialkylaminosulfonyl, Arylaminosulfonyl, carboxyalkoxy, carboxyalkylthio, alkoxycarbonylalkoxy, azyloxy, haloazyloxy, polyhalo-azyloxy, aroyloxy, alkylsulfonyloxy, alkenylsulfonyloxy, arylsulfonyloxy, haloalkyls ulfonyloxy, polyhaloalkylsulfonyloxy, aroylamino, haloalaylamino, alkoxycarbonyloxy, arylsulfonylamino, aminocarbonyloxy, cyanato, isocyanato, isothiozyano, cycloalkylamino, trialkylammonium, arylamino, aryl (alkyl) amino, aralkylamino, alkoxyalkylphosphinyl, alkoxyalkylphosphinoethioyl, alkylhydrosophosphinyl , Dialkoxyphosphino, hydroxyamino, alkoxyamino, aryloxyamine ', aryloxyitnino, oxo, thiono, alkylaminoalkoxy, dialkylaminoalkoxy, alkoxyalkoxy, alkoxyalkenyl, cyanoalkoxy, dialkylsulfonium, -X, = X, -X = R ₃ , = XR ₃ , -X - R ₃ , - Y ₃ R ₅ Y ₃ R ₅ ΥΛ and Y ^ _{0 are} identical or different and are hydrogen, halogeno, alkyl, polyhaloalkyl, a cyano group or aryl; m ⁹ and n * are the same or different and have a value of O to 5; X _{5 are the} same or different and O, S, SO, SOg, NH, CHg, CO, a single bivalent bond, -CH (CH ₃ ) O-, -CH (CN) O-, -CH = NO-, -C (CH ₃₎ = ir0-, -CH ₂ CH ₂ O-, -C = C-, -CHgSO -, - CH ₂ SO ₂ -, -OCH ₂ CH ₂ O-, -CH (alkyl) - or -CONH - is; YiJ _{5 is} 0 or S; Yq ₁ . and YA _{2 are} independently halogen and XJ is 0 or S, wherein X, R ₃ , R, R ₅ , Y ₁ , Y ₂ , Y ₃ and Y are as defined in claim 1. 8. The method according to claim 1, characterized in that the compound has the following formula: γ »93 wherein: ΥΪ, YJ, Yi, Yi and Υ £ are the same or different and are hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiozyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, aryldialkylsilyloxy , Triarylsilyloxy, iormamidino, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, nitro, cyano, hydroxycarbonyl and derived salts, pormamido, alkyl, alkoxy, Polyhaloalkyl, polyhaloalkoxy group, alkoxycarbonyl, substituted amino group in which the permissible substituents are the same or different and one or two of the following: propargyl, alkoxyalkyl, alkylthioalkyl, alkyl, alkenyl, haloalkenyl or polyhaloalkenyl; Alkylthio, polyhaloalkyl thio, alkylsulfinyl, Polyhaloalkylsulfinyl, alkylsulfonyl, Polyhaloalkylsulfonyl, alkylsulfonylamino, Alkylkarbonylamino-, Polyhaloalkylsulfonylamino-, Polyhaloalkylkarbonylaminogruppe, trialkylsilyl, aryldialkylsilyl, triarylsilyl, Sulfonaäure and derived salts, phosphonic acid and derivative salts, Alkoxykarbonylamino-, Alkylaminokarbonyloxy-, Dialkylaminokarbonyloxygruppe, alkenyl, Polyhaloalkenyl, alkenyloxy group, alkynyl, alkynyloxy, polyhaloalkenyloxy, polyhaloalkynyl, polyhaloalkynyloxy group, polyfluoroalkanol, cyanoalkylamino group, semicarbazonomethyl, alkoxycarbonylhydrazonomethyl, alkoxyiminomethyl, unsubstituted or substituted aryloxyiminomethyl, hydrazonomethyl, unsubstituted or substituted arylhydrazonomethyl, a mono-, di- or polysaccharide-fused hydroxy group , Haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, aryloxy, aralkoxy, arylthio, aralkylthio, alkylthioalkyl, arylthio alkyl, arylsulfinyl, arylsulfonyl, haloalkylsulfinyl, Haloalkylsulf onyl, HaIoalkenyloxy-, Haloalkynyloxy-, Haloalkynylthiogruppe, HaIoalkenylsulfonyl, Polyhaloalkenylsulfonyl, ^{Alkoxysulfonyl:!} Aryloxy sulfonyl, propargyloxy group, aroyl, haloazyl, polyhaloazyl, aryloxycarbonyl, aminosulfonyl, alkylaminosulfonyl, dialkylatninosulfonyl, arylaminosulfonyl, carboxyalkoxy, carboxyalkylthio, alkoxycarbonylalkoxy, azyloxy, haloazyloxy, polyhaloazyloxy, aryloxy, alkylsulfonyloxy, alkenylsulfonyloxy -, Arylsulf onyloxy, Haloalkylsulfonyoloxy-, Polyhaloalkylsulfonyloxy-, Aroylamino-, Haloazylamino-, Alkoisykarbonyloxy-, Arylsulfonylamino-, Aminocarbonyloxy-, Cyanato-, Isozyarafco-, Isothiozyano-, Cyclalkylamino-, Trialkylammonium-, Aryl- amino, aryl (alkyl) amino, aralkylamino, alkoxyalkylphosphinyl, alkoxyalkylphosphinothioyl, alkylhydroxyphosphinyl, dialkoxyphosphino, hydroxyamino, alkoxyamino, aryloxyamino, aryloxyimino, oxo, thiono, alkylaminoalkoxy, dialkylaminoalkoxy, alkoxyalkoxy, alkoxyalkenyl, cyanoalkoxy , Dialkylsulfonium, -X, = X, -X = R ₃ , = XR ₃ , -XR ,, -P- Y ₀ R, -Y - E- Y _P R Y ₃ R ₅ ^Y 2 ^R 4
Y ₃ R ₅ Y ₃ R ₅ Xl same or different and is 0, S, SO, SO ₃ \ NH, CH _3, CO, a single divalent linking, -OH, (GH ₃₎ O-, -CH (CN) O-, -CH = HO-, - C (CH ₃ J = NO-, -CH ₂ CH ₂ O-, -C = C-, -CHgSO-, -CH ₂ SO ₂ -, -CH ₂ SO ₂ -, -OCH ₂ CH ₂ O-, - CH is (alkyl) - or -CONH-, m 'is a value from 0 to 5; Is YJ ₆ is hydrogen, alkyl, Alkylkarbonyl, alkylsulfonyl or Polyhaloalkylsulfonyl and Y ^ ₃ and YA _{4 are} independently halogen; wherein X, R ₃ , R ₄ , R ₅ , Y ₁ , Y ₂ , Y ₃ - and Y _{4 are} as defined in claim 1. 9. The method according to claim 1, characterized in that the compound has the following formula hats N = N ^Y 7 wherein: Y ', Y-, Y', Y 'and Y' are the same or different and the following are: hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiozyano, propargylthio, hydroxyimino, alkoxyimino, Trialkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxy, pormamidino, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino, aaninocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, nitro, cyano, hydroxycarbonyl and derived salts, pormamido, Alkyl, alkoxy group, polyhaloalkyl, polyhaloalkoxy group, alkoxycarbonyl, substituted amino group in which the permissible substituents are the same or different and one or two of the following: propargyl, alkoxyalkyl, alkylthioalkyl, alkyl, alkenyl, haloalkenyl or polyhaloalkenyl; Alkylthio, polyhaloalkylthio group, alkylsulfinyl, polyhaloalkylsulfinyl, alkylsulfonyl, polyhaloalkylsulfonyl, alkylsulfo nylamino-, Alkylkarbonylamino-, Polyhaloalkylsulfonylamino-, Polyhaloalkylkarbonylaminogruppe, trialkylsilyl, aryldialkylsilyl, triarylsilyl, sulfonic acid and phosphoric acid and salts derived salts derived, Alkoxykarbonylamino-, Alkylaminokarbonyloxy-, Dialkylaminokarbonyloxygruppe, alkenyl, Polyhaloalkenyl, alkenyloxy, alkynyl, alkynyloxy, Polyhaloalkynyloxy-, PoIyhaloalkenyloxygruppe , Polyhaloalkynyl, polyfluoroalkanol, cyanoalkylamino, semicarbazonomethyl, alkoxycarbonylhydrazonomethyl, alkoxyiminomethyl, unsubituted or substituted aryloxyiminomethyl, hydrazonomethyl, unsubstituted or substituted arylhydrazonomethyl, a mono-, di- or polysaccharide-fused hydroxy group, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, aryloxy, arylkoxy , Arylthio, aralkylthio, alkylthioalkyl, arylthioalkyl, arylsulfinyl, arylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, haloalkenyloxy, haloalkynyloxy, haloalkynylthio, * Ha loalkenylsulfonyl, Polyhaloalkenylsulfonyl, alkoxysulfonyl, aryloxysulfonyl, propargyloxy, aroyl, Hateyl, Polyhaloazyl, Aryloxykarbonyl, Aminosulfony.1, alkylaminosulfonyl, dialkylaminosulfonyl, Arylaminosul _T fonyl, Karboxyalkoxy-, Karboxyalkylthio-, Alkoxykarbonylalkoxy-, Azyloxy-, Haloazyloxy-, Polyhaloazyloxy-, aroyloxy , Alkylsulfonyloxy, alkenylsulfonyloxy, arylsulfonyloxy, haloalkylsulfonyloxy, polyhaloalkylsulfonyloxy, aroylamino, haloazylamino, alkoxycarbonyloxy, arylsulfonic ammonium, arylamino, aryl (alkyl) amino, aralkylamino, alkoxyalkylphoaphinyl, alkoxyalkylphosphinothioyl, alkylhydroxyphosphinyl, dialkoxyphosphino, hydroxyamino, alkoxyamino, aryloxyamino, , Aryloxyimino, oxo, thiono, alkylaminoalkoxy, dialkylaminoalkoxy, alkoxyalkoxy, alkoxyalkenyl, cyanoalkoxy, dialkylsulfonium, -X, = X, -X = R ₃ , = XR ₃ , Y ₁ Y ₁ H ¹ II ¹ -X - R ₃ , - P- Y ₂ R ₄ , -Y ₄ - P _n - Y ₂ R ₄ or ^Y 2 ^R 4 ; and Yi ₁ - and Y ir are independently halogen, wherein X, R ₃ , R ₄ , R ₅ , Y ₁ , Y ₂ , Y " ₃ and Y _{4 are} as defined in claim 1 de. 10. The method according to claim 1, characterized in that the compound has the following formula: wherein: iq and Yi _{1 are the} same or different and YiJ "one or more of the following: hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthlo, polyhaloalkenylthio, thiozyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxy, lormamidino, alkylsulfamido, dialkylsulfamido, Alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, nitro, cyano, hydroxycarbonyl and derived salts, formamido, alkyl, alkoxy, polyhaloalkyl, polyhaloalkoxy, alkoxycarbonyl, substituted amino, wherein the permitted Substances identical or different and one or two of the following are: propargyl, alkoxyalkyl, alkylthioalkyl, alkyl, alkenyl, haloalkenyl or polyhaloalkenyl; Alkylthio, Polyhaloalkylthiogruppe, alkylsulfinyl, Polyhaloalkylsulfinyl, alkylsulfonyl, Polyhaloalkylsulfonyl, Alkylsulfonyamino-, Alkylkarbonylamino-, Polyhaloalkylsulfonylamino-, Polyhaloalkylkarbonylaminogruppe, trialkylsilyl, aryldialkylsilyl, triarylsilyl, Sui-sulfonic acid and salts derived, phosphonic acid and derivative salts, Alkoxykarbonylamino-, Alkylaminokarbonyloxy-j Dialkylarainokarbonyloxygruppe, alkenyl, polyhaloalkenyl, alkenyloxy group, alkynyl, alkynyloxy, polyhaloalkenyloxy group, polyhaloalkynyl, polyhaloalkynyloxy group, polyfluoroalkanol, cyanoalkylamino group, semicarbazonomahyl, alkoxycarbonylhydrazonomethyl, alkoxyiminomethyl, unsubstituted or substituted aryloxyiminomethyl, hydrazonomethyl, unsubstituted or substituted arylhydrazonomethyl, one condensed with a mono-, di- or polysaccharide Hydroxy, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, aryloxy, aralkoxy, arylthio, aralkylthio, alkylthioalkyl, arylthioalkyl , Arylsulfinyl, arylsulfonyl, HaIoalkylsulfinyl, haloalkylsulfonyl, Haloalkenyloxy-, HaIoalkynyloxy-, Haloalkynylthiogruppe, Haloalkenylsulfonyl, Polyhaloalkenylsulfonyl, Alkoxysulfonyl, aryloxysulphonyl, propargyloxy, aroyl, · Haloazyl, Polyhaloazyl, Aryloxykarbonyl, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, arylaminosulfonyl, Karboxyalkoxy-, Karboxyalkylthio-, Alkoxycarbonylalkoxy, azyloxy, haloazyloxy, polyhaloazyloxy, aroyloxy, alkylsulphonyloxy, alkenylsulphonyloxy, arylsulphonyloxy, haloalkylsulphonyloxy, polyhaloalkylsulphonyloxy, aroylamino, haloazylamino, alkoxycarbonyloxy, arylsulphonylamino, aminocarbonyloxy, cyanato, isocyanato, Isothiocyanine, cycloalkylamino, trialkylammonium, arylamino, aryl (alkyl) amino, aralkylamino, alkoxyalkylphosphinyl, alkoxyalkylphosphinothioyl, alkylhydroxyphosphinyl, dialkoxyphosphino, hydroxyamino, alkoxyamino, aryloxyamino) aryloxyimino, oxo, thiono, alkylaminoakoxy, Dialkylaminoalkoxy, alkoxy alkoxy, alkoxyalkenyl, cyanoalkoxy, dialkylsulfonium,   Λ. j - Λ} ~ Α - Ro $ - Χ * ™ ίΐ -XR ₃ , -P ^ - Y ₂ R ₄ , -Y ₄ -P- Y ₂ R ₄ Ϊ1 or ^Y 2 ^R 4 A 'is as defined for R ₁ in claim 1; X! J ₀ as defined for Σ in claim 1 and X £ _o halogen, a cyano group, alkyl, alkoxy, polyhaloalkyl, a Polyhaloalkoxygruppe or polyhaloalkyl is sulphonyloxy, wherein X, R, R, R ₅ , Y 1, Y ₂ , Y and Y _{4 are} as defined in claim 1. 11. The method according to claim 1, characterized in that the compound has the following formula: ^Y 22 wherein: R _{'12 is} as defined for R ₁ in claim 1; Y is _"22 halogen, a cyano group, alkyl, alkoxy, polyhaloalkyl, Polyhaloalkoxy- or Polyhaloalkylsulfonyloxygruppe and Y _{'23 is} hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiozyano, Pfopargylthio-, hydroxyimino, alkoxyimino, Trialkylsilyloxy-, aryldialkylsilyloxy, triarylsilyloxy, lOrmamidino-, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, Polyhaloalkoxysulfonyl, hydroxy, amino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, atliothiocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, nitro, cyano, hydroxycarbonyl, and derived salts, imideamido, alkyl, alkoxy, polyhaloalkyl, polyhaloalkoxy, alkoxycarbonyl, substituted amino, in which the permissible substituents are the same or different and one or two of the following are / propargyl, alkoxyalkyl, alkylthioalkyl, alkyl, alkenyl, haloalkenyl or polyhaloalkenyl; Alkylthio, polyhaloalkylthio, alkylsulfonylamino group, alkylsulfinyl, polyhaloalkylsulfinyl, alkylsulfonyl, polyhaloalkylsulfonyl, alkylcarbonylamino, polyhaloalkylsulfonylamino, polyhaloalkylcarbonylamino, trialkylsilyl, aryldialkylsilyl, triarylsilyl, sulfonic acid and derived salts, phosphonic acid and derived salts, alkoxycarbonylamino, alkylaminocarbonyloxy, dialkylaminocarbonyloxy group, Alkenyl, polyhaloalkenyl, alkenyloxy group, alkynyl, alkynyloxy, polyhaloalkenyloxy group, polyhaloalkynyl, polyhaloalkynyloxy group, polyfluoroalkanol, cyanoalkylamino group, semicarbazonomethyl, alkoxycarbonylhydrazonomethyl, alkoxyiminomethyl, unsubstituted or substituted aryloxyiminomethyl, hydrazonomethyl, unsubstituted or substituted aryhydrazonomethyl, one condensed with a mono-, di- or polysaccharide Hydroxy, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, aryloxy, aralkoxy, arylthio, aralkylthio, alkylthioalkyl, arylthioalkyl, Arylsulfinyl, arylsulfonyl, haloalkylsulfinyl, Haloalkylsulfonyl, Haloalkenyloxy-, Haloalkynyloxy-, Haloalkynylthiogruppe, Haloalkenylsulfonyl, Polyhaloalkenylsulfonyl, alkoxysulfonyl, aryloxysulfonyl, propargyl 'oxy, aroyl, Haloazyl, Polyhaloazyl, Aryloxykarbonyl, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, arylaminosulfonyl, Karboxyalkoxy-, Karboxyalkylthio-, Alkoxykarbonylalkoxy-, Azyloxy- , Haloazyloxy, polyhaloazyloxy, aroyloxy, alkylsulfonyloxy, alkenylsulfonyloxy, arylsulfonyloxy, haloalkylsulfonyloxy, polyhaloalkylsulfonyl oxy, aroylamino, haloazylamino, alkoxycarbonyloxy, arylsulfonylamino, aminocarbonyloxy, cyanato, isocyanato, isothiozyano , Cycloalkylamino, trialkylammonium, arylamino, aryl (alkyl) amino, aralkylamino, alkoxyalkylphosphinyl, alkoxyalkylphosphinothyoyl, alkylhydroxyphosphinyl, dialkylaminoalkoxy, dialkoxyphosphino, hydroxyamino, alkoxyamino, aryloxyamino, aryloxyimino, oxo, thiono, alkylaminoalkoxy, Alkoxyalkoxy group, alkoxyalkenyl, cyanoalkoxy group e, dialkylsulfonium, -Χ, = X, -Χ = R «, β X-R-, is; in which X, R 1, R ₄₅ R ₅ ,
Finished are. Y ₃ and Y. as in claim 1 de12. A method according to claim 1, characterized in that the compound has the following formula; 31 Y ' 32 wherein: A ' ₁ as R ₂ is defined in claim 1 and Y 'and Y'O _{2 are the} same or different and are halogen, alkyl or an alkoxy group. 13. The method according to claim 1, characterized in that the compound has the following formula: Y '^ o 34 wherein: A'ρ is as defined in claim 1 R ₁ ; X is defined as X in claim 1 and Y »- and Y'o- are identical or different and are halogen, alkyl or an alkoxy group. A method according to claim 1, characterized in that the compound has a formula selected from worm: ν> ν * ν * ν * ν * ν * ν * 'ν * ν ν · ν * * 41' 42 '* 43' 44 '. 45 '* 46 »* 47' ^X 48 * * 49 '5Ο * * 51' Il It ^Υ 48 » ^Υ 52» ^Υ 53 ' ^Υ 54' ^Υ 55 ' ^Υ 5δ' ^Υ 57 ' ^Υ 59' ^Υ 58 » ^Υ 59 ' ^Υ 60' Yi ₁ , and Y ^ p are the same or different and ¥ 5 ..» YJg "Yig, Y52" ¥ 56 ^"11 O- Ϊ59 one or more of the following are: hydrogen, halogen, Alkylkarbonyl, Alkylkarbonylalkyl, Alkoxykarbonylalkyl, Alkoxykarbonylalkylthio-, Polyhaloalkenylthio-, Thiozyano-, Propargylthio-, hydroxyimino, alkoxyimino, trialkylsilyloxy , Aryldialkylsilyloxy, triarylsilyloxy, samaramidino, alkylsulfamido, dialkylsulfamido, hydroxy, amino, alkoxysulfonyl, polyhaloalkoxysulfonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbohyl, dialkylaminothiocarbonyl, nitro, cyano, hydroxycarbonyl and derived salts, formamido, alkyl , Alkoxy group, polyhaloalkyl, polyhaloalkoxy group, alkoxycarbonyl, substituted amino group in which the permissible substituents are the same or different and one or two of the following: propargyl, alkoxyalkyl, A alkylthioalkyl, alkyl, alkenyl, haloalkenyl or polyhaloalkenyl; Alkylthio, polyhaloalkylthio group, alkylsulfinyl, polyhaloalkylsulfinyl, alkylsulfonyl, polyhaloalkylsulfonyl, alkylsulfonylamino, alkylcarbonylatninc ⁷ , polyhaloalkylsulfonylamino, polyhaloalkylcarbonylamino, trialkylsilyl, aryldialkylsilyl, triarylsilyl, sulfonic acid and derived salts, phosphonic acid and derived salts, alkoxycarbonylamino, alkyiaminocarbonyloxy , Dialkylaminocarbonyloxy group, alkenyl, polyhaloalkenyl, alkenyloxy group, alkynyl, alkynyloxy, polyhaloalkenyloxy group, polyhaloalkynyl, polyhaloynyloxy group, polyfluoroalkanal, cyanoalkylamino group, semicarbazonomethyl, alkoxycarbonylhydrazonoethyl, alkoxyiminomethyl, unsubstituted or substituted aryloxyiminomethyl, hydrazonomethyl, unsubstituted or substituted arylhydrazonomethyl, one with a mono-, di-, or polysaccharide condensed hydroxy, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, aryloxy, ayalkoxy, arylthio, aralkylthio, alkylthioalkyl, aryl ioalkyl, arylsulfinyl, arylsulfonyl, haloalkylsulfinyl, Haloalkenyloxygruppe, haloalkylsulfonyl, Ha'loalkynyloxy-, Haloalkynylthiogruppe, Haloalkenylsulfonyl, PoIyhaloalkenylsulfonyl, alkoxysulfonyl, aryloxysulfonyl, propargyloxy, aroyl, Haloazyl, Polyhaloazyl, Aryloxykarbonyl, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, Arylatninosulfonyl, Karboxyalkoxy-, Karboxyalkylthio- , Alkoxycarbonylakloxy, azyloxy, haloazyloxy, polyhaloazyloxy, aroyloxy, alkylsulphonyloxy, Alkenylsulfonyloxy, arylsulfonyloxy, haloalkylsulfonyloxy, polyhaloalkylsulfonyloxy, aroylamino, haloazylamino, alkoxycarbonyloxy, arylsulfonylamino, aminocarbonyloxy, cyanator, isocyanato, isothiocyano, cycloalkylamino, trialkylammonium, arylamino, aryl (alkyl) amino, , Aralkylamino, alkoxyalkylphosphinyl, alkoxyalkylphosphinothioyl, alkylhydroxyphosphinyl, dialkoxyphosphino, hydroxyamino, alkoxyamino, aryloxyamino, aryloxyimino, oxo, thiono, alkylaminoalkoxy, dialkylaminoalkoxy, alkoxyalkoxy, alkoxyalkenyl, cyanoalkoxy, dialkylsulfonium, -X y - X, -JC ⁼ Hn) = Λ.- Ά * j,. -Χ - R ₃ , - P - Y? R? ,, - Y. - P - and Ai like defined in claim 1 Y ₃ R ₅ Ai, AJ, AA, AX,
are and , X ij ^x ifi »^ -17» ^x i8 ^ ⁰¹ ^ ^X 19 δ- '· ⁶ ·' - ⁰ ' ¹ or different and 0, S, SO, SO ₂ , MH, CH ₂ , CO, a single bivalent bond , -CH (CH ₃ ) O-, -CH (CN) O-, -CH = NO-, -C (CH ₃ J = NO-, -CH ₂ CH ₂ O-, C = C-, -CH ₂ SO, -OHgSOg-, -OCH ₂ CH ₂ O-, -CH (Al-) kyl) - or -CONH- are, wherein X, R ,, R ₄ , R ₅ ,
are defined. Y ₃ and Y. as in claim 1. 15 Process according to claim 1, characterized in that the compound has the formula: wherein: AIq as R- is defined in point 1, XAq as X is defined in point 1, Ai- is a substituted or unsubstituted, five-membered heterocyclic ring system having at least one nitrogen atom in which the permissible substituents are the same or different and one or more of the following: hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiozyano , Propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxy, pormamidino, alkylsulfamido, dialkylsulfamido, allcoxysulfonyl, polyhaloalkynysulfonyl, hadroxy, amino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, nitro , Cyano group, hydroxy carbonyl and derived salts, E ammonium amido group, alkyl, alkoxy group, polyhaloalkyl, polyhaloalkoxy group, alkoxycarbonyl, substituted substituted amino group in which the permissible substituents are the same or different and one or two of the following: propargyl, alkoxyalkyl, alkylthioalkyl, alkyl, alkenyl, Haloalkenylooder BiLyhaloalkenyl; Alkylthio, polyhaloalkylthio, alkylsulfonylamino group, alkylsulfinyl, polyhaloalkylsulfonyl, polyhaloalkylsulfinyl, alkylsulfonyl, alkylcarbonylamino, polyhaloalkylsulfonylamino, polyhaloalkylcarbonylamino, trialkylsilyl, aryldialkylsilyl, triarylsilyl, sulfonic acid and derived salts, phosphonic acid and derived salts, alkoxycarbonylamino, alkylaminocarbonyloxy, dialkylaminocarbonyloxy group, ' Alkenyl, polyhaloalkenyl, alkenyloxy group, alkynyl, alkynyloxy, polyhaloalkynoxy group, polyhaloalkynyl, polyhaloalkenyloxy group, polyfluoroalkanaol, cyanoalkylamino group, semicarbazonomethyl, alkoxycarbonylhydrazonomethyl, alkoxyiminomethyl, unsubstituted or substituted aryloxyiminomethyl, hydrazonomethyl, unsubstituted or substituted arylhydrazonomethyl, one with a mono-, di- or Polysaccharide condensed hydroxy, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, aryloxy, aralkoxy, arylthio, aralkylthio, alkylthioalkyl, arylthioalky l, arylsulfinyl, arylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, Haloalkenyloxy-, Haloalkynyloxy-, Haloalkynylthiogruppe, Haloalkenylsulfonyl, Polyhaloalkenylsulfonyl, alkoxysulfonyl, aryloxysulfonyl, propargyloxy, aroyl, Haloazyl, Polyhaloazyl, Aryloxykarbonyl, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, arylaminosulfonyl, Karboxyalkoxy-, Karboxyalkylthio-, Alkoxycarbonylalkoxy, azyloxy, haloazyloxy, polyhaloazyloxy, aroyloxy, alkylsulfonyloxy, alkenylsulfonyloxy, arylsulfonyloxy, haloalkylsulfonyloxy, polyhaloalkylsulfonyloxy, aroylamino, hatozylamino, alkoxycarbonyloxy, arylsulfonylamino, aminocarbonyloxy, cyanato, isocyanato , Isothiocyanato, cycloalkylamino, trialkylammonium, arylamino, aryl (alkyl) amino, arylalkylatnino, alkoxyalkylphosphinyl, alkoxyalkylphosphinothioyl, alkylhydroxyphosphinyl, dialkoxyphosphino, hydroxyamino, alkoxyamino, aryloxyamino, aryloxyimino, oxo, thiono, alkylaminoalkoxy , Dialkylaminoalkoxy, alk oxyalkoxy group, alkoxyalkenyl, cyanoalkoxy group, dialkylsulfonium, -X, = X, -X = R, = X-R. 'H -X - R ₃ , - P - Y ₂ R ₄ , --Y ₄ - P - Y ₂ R ₄ ^Y 2 ^R 4 ^Y 3 ^R 5 Xl Ji. are the same or different and one or more of the following are: hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiozyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxy, fromamido , Alkylsulfamido, dialkylsulfamido, alkoxysulphonic vinyl, polyhaloalkoxysulfonyl, hydroxy, amino groups, aminocarbonyl, alkylaminocarbonyl, dialkylatninocarbonyl, amino thiocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, nitro, cyanogen, hydroxycarbonyl and derivative salts, ortho-damido group, alkyl, alkoxy, polyalkyl, polyhaloalkoxy, alkoxycarbonyl, substituted amino, in which permissible substituents are the same or different and one or two of the following are: propargyl, alkoxyalkyl, alkylthioalkyl, alkyl, alkenyl, haloalkenyl or polyhaloalkenyl; Alkylthio, Polyhaloalkylthiogruppe, alkylsulfinyl, Polyhaloalkylsulfonyl, Polyhaloalkylsulfinyl, alkylsulfonyl, Alkylsulf onylamino-, Alkylkarbonylamino-, Polyhaloalkylsulfonylamino-, Polyhaloalkylkarbonylaminogruppe, trialkylsilyl, aryldialkylsilyl, triarylsilyl, sulfonic acid and derivative salts, and salts derived Phojsphnsäure, AIkoxykarbonylatnino-, Alkylarainokarbonyloxy-, Dialkylaminokarbonyloxygruppe, alkenyl , Polyhaloalkenyl, alkenyloxy, alkynyloxy, alkynyl, polyhaloalkenyloxy, polyhaloalkynyl, polyhaloalkynyloxy, polyfluoroalkanolj, cyanoalkylamino, setnikarbazonotnethyl, alkoxycarbonylhydra-monoethyl, alkoxyiminomethyl, unsubstituted or substituted aryloxyiminomethyl, hydrazonomethyl, unsubstituted or substituted arylhydrazonomethyl, a mono-, di- or polysaccharide-fused hydroxy group, Haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, aryloxy, aralkoxy, arylthio, aralkylthio, alkylthioalkyl, arylthio lkyl, arylsulfinyl, arylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, Haloalkenyloxy-, Haloalkynyloxy-, Haloalkynylthiogruppe, haloalkenyl sulfonyl, sulfonyl Polyhaloalkenyl, alkoxysulfonyl, aryloxysulfonyl, propargyloxy, aroyl, Haloazyl, Polyhaloazyl, Aryloxykarbonyl, Aminoaulfonyi, Alkylamlno sulfonyl, di alkylamino sulfonyl, arylaminosulfonyl, Carboxyalkoxy, carboxyalkyltoio, alkoxycarbonylalkoxy, azyloxy, haloazyloxy, polyhaloacyloxy, aroyloxy, alkylsulfonyloxy, alkenylsulfonyl oxy, alkoxycarbonyloxy, arylsulfonyl oxy, haloalkylsulfonyloxy, polyhaloalkylsulfonyloxy, aroylamino, haloazylamino, arylsulfonylamino -, aminocarbonyloxy, cyanato, laozyanato, isothiocyanato, cycloalkylamino, trialkylammonium, arylamino, aryl (alkyl) amino, aralkylamino, alkoxyalkylphosphino, alkoxyalkylphosphinoethyl, alkylhydroxyphosphinyl, dialkoxyphosphino, hydroxyamino, alkoxyamino, aryloxyamino, Aryloxyimino, oxo, thiono,., Alkylaminoalkoxy, dialkyla minoalkoxy, alkoxyalkoxy, alkoxyalkenyl, cyanoalkoxy, dialkylsulfonium, -X, = X, -X = R ₃ , = XR ₃ , l · wherein X, R ₃ , R ₄ , R ₅ ,
Finished are. , Y _g , Y ₃ , Y ₄ as in claim 1 de 16. The method according to claim 1, characterized in that the compound has a formula which is selected from: wherein: ^Y 6 ₅ « ^Y 66 ' ^Y 67' ^Y 68 ' ^Y 6 ₉ ' ^Y 70 · ^Y 71 ' ^Y 72' ^Y 74 '%' Y ₇₆ , ϊ _γ7 , ϊ ₇₈ . ϊ ₇₉ . * 80 ^ ^{111 'Υ} 81 S are ^{facilitated or} different and Y £ _7> Y _70, Y ₇ ^ * ^ ₇ g and ^y ₇ 9 are one or more of the following: hydrogen, halogen, Alkylkarbonyl, Alkylkarbonylalkyl, Alkoxykarbonylalkyl, Alkoxykarbonyl, alkylthio, polyhaloalkenylthio, thiozyano, propargylthio, hydroxyimino, alkoxyimino, trialkylailyloxy, aryldialkylailyloxy, triarylsilyloxy, iormamidino, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxyeulfonyl, hydroxy, amino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl , Aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, nitro, cyano, hydroxycarbonyl and derived salts, ammonium amido group, alkyl, alkoxy group, polyhaloalkyl, polyhaloalkoxy group, alkoxycarbonyl, substituted amino group in which the permissible substituents are the same or different and one or two of the following: propargyl, Alkoxyalkyl, alkylthioalkyl, alkyl, alkenyl, haloalkenyl or polyhaloalkenyl; Alkylthio, polyhaloalkylthio, alkylsulfonylamino, alkylsulfinyl, polyhaloalkylsulfinyl, alkylsulfonyl, polyhaloalkylsulfonyl, alkylcarbonylamino, polyhaloalkylsulfonylamino, polyhaloalkylcarbonylamino, trialkylsilyl, aryldialkylsilyl, triarylsilyl, sulfonic and derived salts, phosphonic and derived 4 salts, alkoxycarbonylamino, alkylaminocarbonyloxy, dialkylaminocarbonyloxy , Alkenyl, polyhaloalkenyl, alkenyloxy group, alkynyl, alkynyloxy, psylloroalkenyloxy group, polyhaloalkynyl, polyhaloalkynyloxy group, polyfluoroalkanepl, cyanoalkylamino group, semicarbazonomethyl, alkoxycarbonylhydrazonomethyl, alkoxyiminomethyl, unsubstituted or substituted aryloxyiminomethyl, hydrazonomethyl, unsubstituted or substituted arylhydrazonomethyl, one with a mono-, di- or polysaccharide fused hydroxy group, haloalkyl, haloalkenyl, halo alkynyl, alkoxyalkyl, aryloxy, aralkoxy, arylthio, aralkylthio, alkylthioalkyl, arylthioalkyl, Arylsulf ynyl, arylsulfonyl, Haloalkylaulfinyl, haloalkyl _t sulfonyl, Haloalkenyloxy-, Haloalkynyloxy-, Haloalkynylthiogruppe, Haloalkenylsulfonyl, Polyhaloalkenylsulfonyl, alkoxysulfonyl, aryloxysulfonyl, propargyloxy, aroyl , Haloazyl, polyhaloazyl, aryloxycarbonyl, atninosulfonyl ,. Alkylaminosulfonyl, dialkylaminosulfonyl, arylaminosulfonyl, carboxyalkoxy, carboxyalkylthio, alkoxycarbonylalkoxy, azyloxy, haloazyloxy, polyhaloacyloxy, aroyloxy, alkylsulfonyloxy, alkenylsulfonyloxy, arylsulfonyloxy, haloalkylsulfonyloxy, polyhaloalkylsulfo-nyloxy, aroylamino, haloazylamino Alkoxycarbonyloxy, arylsulfonylamino, aminocarbonyloxy, cyanato, isocyanato, isothiozyano, cycloalkylamino, trialkylammonium, arylamino, aryl (alkyl) amino, aralkylamino, etc. alkoxyalkylphosphinyl, alkoxyalkylphosphinothioyl, alkylhydroxyphosphinyl, dialkylaminoalkoxy, dialkoxyphosphino , Hydroxyamino, alkoxyamino, aryloxyamino, aryloxyimino, oxo, thiono, alkylarainoalkoxy, alkoxyalkoxy, alkoxyalkenyl, cyanoalkoxy, dialkylsulfonium, or -X-R ₃ , -P-Y ₉ R 1 -Y, -P-Y ₉ R, ^Y 3 ^R 5 r 'is a value of 0 or 1; ^X \ i ₂ ^A 13 ^'A H' ^A 15 ^'A 16 ^A 17 ^uni as R defined in claim 1 ₁ and X ₁ , X _'22 , X ₂₃ , X ₂₄ , X ₂₅ and X _{26 are defined} as X in claim 1, wherein X, R ₃ , R ₄ , R ₅ , Y ₁ , Y ₂ , Y ₃ and Y _{4 are} as defined in claim 1. 17, A method according to claim 1, characterized in that the compound has the following formula: ^{Υ έ} ₅ where s γ "γ", γ »γ» _ and R ' _{7 are the} same or different and are the following: hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiozyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, Aryldialkylsilyloxy, triarylsilyloxy, formamidino, alkylsulfido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, nitro, cyano, hydroxycarbonyl and derived salts, formamido, alkyl Alkoxy group, polyhaloalkyl, polyhaloalkoxy group, alkoxycarbonyl, substituted amino group in which the permissible substituents are the same or different and one or two of the following: propargyl, alkoxyalkyl, alkylthioalkyl, alkyl, alkenyl, haloalkenyl or polyhaloalkenyl; Alkylthio, Polyhaloalkylthiogruppe, alkylsulfinyl, Polyhaloalkylsulfinyl, alkylsulfonyl, Polyhaloalkylsulfonyl, Alkylsulf onylatnino-, Alkylkarbonylamino-, Polyhaloalkylsulfonylatnino-, PoIyhaloalkylkarbonylaminogruppe, trialkylsilyl, aryldialkylsilyl, triarylsilyl, sulfonic acid and phosphonic acid salts and salts derived abgeMtete, Alkoxykarbonylamino-, Alkylaminokarbonyloxy-, Dialkylaminokarbonyloxygruppe, alkenyl , Polyhaloalkenyl, alkenyloxy group, alkynyl, alkynyloxy, polyhaloalkenyloxy group, polyhaloalkynyl, polyhaloalkynyloxy group, polyfluoroalkanol, cyanoalkylamino group, semicarbazonoraethyl, alkoxycarbonylhydrazonomethyl, alkoxyiminomethyl, unsubstituted or substituted aryloxyiminomethyl, hydrazonomethyl, unsubstituted or substituted arylhydrazonomethyl, one having a mono-, di- or Pd-lysaccharide condensed hydroxy group, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, aryloxy, aralkoxy, arylthio, aralkylthio, alkylrthioalkyl, arylthioal kyl, arylsulfinyl, arylsulfonyl, Haloalkynyloxygruppe, haloalkylsulfonyl, haloalkylsulfinyl, Haloalkenyloxy-, Haloalkynylthiogruppe, Haloalkenylsulfonyl, Polyhaloalkenylsulfonyl, alkoxysulfonyl, aryloxysulfonyl, propargyloxy, aroyl, Haloazyl, Polyhaloazyl, Aryloxykarbonyl, aminosulfonyl, Alkylaminosiolfonyl, dialkylaminosulfonyl, arylaminosulfonyl, Karboxyalkoxy-, Karboxyalkylthio-, Alkoxykarbonylalkoxy , Azyloxy, haloacyloxy, polyhaloazyloxy, aroyloxy, alkylsulphonyloxy, alkenylsulphonyloxy, arylsulphonyloxy, haloalkylsulphonyloxy, polyhaloalkylsulphonyloxy, aroylamino, haloazylamino, alkoxycarbonyloxy, arylsulphonylamino, aminocarbonyloxy, cyanato, isocyanato, Tothiotycano, cycloalkylamino, trialkylammonitim, arylamino, aryl (alkyl) amino, aralkylamino, alkoxyalkylphosphinyl, alkoxyalkylphosphinothioyl, alkylhydroxyphosphinyl, dialkoxyphosphino, hydroxyamino, alkoxyamino, aryloxyamino, aryloxyimino, oxo, thiono, alkylaminoalkoxy, Dialkylaminoalkox y, alkoxyalkoxy, alkoxyalkenyl, cyanoalkoxy, dialkylsulfonium, -X, = X, -X = Ro> ⁼ Χ ~ ί ^ ο, II ¹ II ¹ -XR ₃ , - P- Y ₂ R ₄ , -Y ₄ -P- Y Y ₃ R ₅ Y ₃ R ₅ ^Y 2 ^R 4 5 and Y ₃ R ₅ Xl-vd.e X is defined in claim 1, wherein X, R ₃ , R ₄ , R ₅ , Y ₁ , Y ₂ , Y ₃ and Y _{4 are} as defined in claim 1. 18. Method according to. Claim 1, characterized in that the compound has a formula selected from * © ^Y 60 and wherein: R 'and YA ₀ are the same or different UIdRiJ ₈ is one or more of the following: hydrogen, halogen, Alkylkarbonyl, Alkylkarbonylalkyl, Alkoxykarbonylalkyl, thio Alkoxykarbonylalkyl, Polyhaloalkenylthio-, Thiozyano-, Propargylthio-, hydroxyimino, alkoxyimino, trialkylsilyloxy, Aryldialkylsilyloxy, triarylsilyloxy, lmoramidino, alkylsulfoamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, nitro, cyano, hydroxycarbonyl and derivative salts, orthamido, alkyl, alkoxy , Polyhaloalkyl, polyhaloalkoxy group, alkoxycarbonyl, substituted amino group in which the permissible substituents are the same or different and one or two of the following are / propargyl, alkoxyalkyl, alkylthioalkyl, alkyl, alkenyl, haloalken-. nyl or polyhaloalkenyl; Alkylthio, Polyhaloalkylthiogruppe, alkylsulfinyl, Polyhaloalkylsulfonyl, Polyhaloylkylsulfinyl, alkylsulfonyl, alkylsulfonylamino, Alkylkarbonylamino-Polyhaloalkylsulfonylamino-, Polyhaloalkylkarbonylaminogruppe, trialkylsilyl, aryldialkylsilyl, triarylsilyl, Sui-sulfonic acid and salts derived, phosphonic acid and derivative salts, Alkoxykarbonylamino, Alkylaminokarbonyloxy-, Dialkylaminokarbonyloxygruppe, alkenyl, Polyhaloalkenyl, alkenyloxy group, alkynyl, alkynyloxy, polyhaloalkenyloxy group, polyhaloalkynyl, polyhaloalkynyloxy group, polyfluoroalkanaol, cyanoalkylamino group, semicarbazonomethyl, alkoxycarbonylhydrazonomethyl, alkoxyiminomethyl, unsubstituted or substituted aryloxyiminomethyl, hydrazonomethyl, unsubstituted or substituted arylhydrazonomethyl, a hydroxyl group condensed with a hono-, di- or polysaccharide, Haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, aryloxy, aralkoxy, arylthio, aralkylthio, alkylthioalkyl, arylthioalkyl, Arylsulfinyl, arylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, Haloalkenyloxy-, Haloalkynyloxy-, Haloalkynylthiogruppe, Haloalkenylsulfonyl, Polyhaloalkenylsulfonyl, alkoxysulfonyl, AryloxysulfonjL, propargyloxy, aroyl, Haloazyl, Polyhaloazyl, Aryloxykarbonyl, Atninosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, arylaminosulfonyl, Karboxyalkoxy-, Karboxyalkylthio-, Alkoxykarbonylalkoxy- , Azyloxy, haloazyloxy, polyhaloazyloxy, aroyloxy, alkylsulphonyloxy, alkenylsulphonyl, arylsulphonyloxy, haloalkylsulphonyloxy, polyhaloalkylsulphonyloxy, aroylamino, haloazylamino, alkoxycarbonyloxy, arylsulphonylamino, aminocarbonyloxy, cyanato, isocyanato , Isothiocyanato, cycloalkylamino, trialkylammonium, arylamino, aryl (alkyl) amino, aralkylamino, alkoxyalkylphosphinyl, alkoxyalkylphosphinothioyl, alkylhydroxyphosphinyl, dialkylphosphino, hydroxyamino, alkoxyamino, aryloxyamino, aryloxyimino, oxo, thiono, alkylaminoalkoxy, dialkylaminoalkoxy, alkoxyalkoxy, alkoxyalkenyl, cyanoalkoxy, dialkylsulfonium, -X, = X, -X = Rq. j - X-R-3, Y ₁ ^{3 3} Y ₁ II ¹ II ¹ -X - R ₃ , - PY ₂ R ₄ , -Y ₄ - PY ₂ R ₄ Y ₃ R ₅ Y ₃ R ₅ or ^Y 2 ^R 4 Y ₃ R ₅ AIj ₈ as R ₁ is defined in claim 1 and ₂ O as X is defined in claim 1, wherein X, R, R, R, -, Y ^, Y _2, Yo and Y are as defined in claim 1. Process according to claim 1, characterized in that the compound has the formula: ZA ^ g ₂ wherein: Rig as R ^ is defined in claim 1; XZq as X is defined in claim 1; ZJ and Zi are independently O, S, O-, Cg-alkylidene, substituted or unsubstituted benzylidene, MH or NR "', wherein R ¹ " is alkyl, aryl, aralkyl, alkenyl or alkynyl, and Yi .. and YAp are independently halogen, alkyl or an alkoxy group. 20. The method according to claim 1, characterized in that the compound has the following formula: U = H YAc: ^L 94 wherein: R'q is as defined in claim 1 R ₁ ; X _{1 is} as defined in claim 1; ZA is O, S, CL-Cg alkylidene, substituted a or unsubstituted benzylidene, 1IH or WR "', wherein R"' is alkyl, aryl, aralkyl, alkenyl or alkynyl, and Y ', Y "and YA _{5 are} identical or different and the following are: hydrogen, halogen, alkylcarbonyl, alkylcarbonyl alkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, ihiozyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsllyloxy, aryldialkylsilyloxy, triarylsilyloxy, formamidino, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino, aminocarbonyl, Alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, hydroxycarbonyl, hydroxycarbonyl and derived salts, formamil, alkyl, alkoxy, polyhaloalkyl, polyhaloalkoxy, alkoxycarbonyl, substituted amino in which the permissible substituents are the same or different and one or two of the following: propargyl Alkoxyalkyl, alkylthioalkyl, alkyl, alkenyl, haloalkenyl or polyhaloalkenyl; Alkylthio, Polyhaloalkylthiogruppe, alkylsulfinyl, Polyhaloalkylsulfinyl, Alkylsulf onyl, Polyhaloalkylsulfonyl, alkylsulfonylamino, Alkylkarbonylamino-, Polyhaloalkylsulfonylamino-, Polyhaüoalkylkarbonylaminogruppe, trialkylsilyl, aryldialkylsilyl, 'üriarylsilyl, sulfonic acid and salts derived, phosphonic acid and derivative salts, Alkoxykarbonylamino-, Alkylaminokarbonyloxy-, Dialkylaminokarbonyloxygruppe, Alkenyl, polyhaloalkenyl, alkenyloxy group, alkynyloxyalkynyloxy, polyhaloalkenyloxy group, polyhaloalkynyl, polyhaloalkynyloxy group, polyfluoroalkanol, cyanoalkylamino group, semicarbazonomethyl, alkoxycarbonylhydrazonomethyl, alkoxyiminomethyl, unsubseduated or substituted aryloxyiminomethyl, hydrazonomethyl, unsubstituted or substituted arylhydrazonomethyl, one condensed with a mono-, di- or polysaccharide Hydroxy, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, aryloxy, aralkoxy, arylthio, aralkylthio, alkylthioalkyl, arylthioal kyl, arylsulfinyl, arylsulfonyl, haloalkylsulfinyl, haloalkylulfonyl, haloalkenyloxy, haloalkynyloxy, haloalkynylthio, haloalkenylsulfonyl, polyhaloalkenylsulfonyl, alkoxynesulfonyl, aryl oxy sulfonyl, propargyl oxy, carboxyalkoxy, aroyl, haloazyl, polyhaloazyl, aryloxycarbonyl, amino, sixlfyl , Alkylaminosulphonyl, dialkylaminosulphonyl, arylaminosulphonyl, iarboxyalkylthio, alkoxycarbonylalkoxy, azyloxy, haloazyloxy, polyhaloacyl oxy, aroyloxy, alkylsulphonyloxy, alkenylsulphonyl, arylsulphonyloxy, haloalkylsulphonyloxy, polyhaloalkylsulphonyloxy , Aroylamino, haloazylamino, alkoxycarbonyloxy, arylsulfonylamino, aminocarbonyloxy, cyanato, isocyanato, isothiocyanato, cyclalkylamino, trialkylammonium, arylamino, aryl (alkylamino, aralkylamino, alkoxyalkylphosphinyl, alkoxyalkylphosphinohidioyl, alkylhydroxyphosphinyl) dialkoxyphosphino, hydroxyamino, AIkoxyamino, aryloxyamino, aryloxyimino, oxo, thiono, alkylaminoalkoxy, Dia alkylaminoalkoxy, alkoxyalkoxy, alkoxyalkenyl, cyanoalkoxy, dialkylsulfonium, X, -X = -X - R ₃ , - P _n -
or = XR ₃ , . ^ Y ₂ R ₄ , -YPY ₂ R ₄
Y ₃ R ₅ ^X Y ₃ R ₅ Y ₃ R ₅ wherein X, R ₃ , R ₄ , R ₅ , Y ₁ , Y ₂ , Y ₃ and Y _{4 are} as defined in claim 1. 21. The method according to claim 1, characterized in that the compound has the following formula: ^l 96    97 ^l 99 worm: ^ as R.J is defined in point 1; X ' as X is defined in point 1 and »Yq7» ^ 99 are the same or different and are hydrogen, halogen, alkyl or an alkoxy group » 22. The method according to claim 1, characterized in that the compound has the following formula: C =. N wherein: R 'is defined as R ₁ in point 1 and Xi and Z! independently of one another are hydrogen, halogen, a hydroxy group, alkyl, an alkoxy group, alkylcarbonyl or alkoxycarbonyl. 23. The method according to claim 1, characterized in that the compound has the following formula: Cl Method according to claim 1, characterized in that the compound has the following formula: Cl Process according to claim 1, characterized in that the compound has the following formula: 26. The method according to claim 1, characterized in that the compound has the following formula: 27. The method according to claim 1, characterized in that the compound has the following formula: Cl Cl 28. The method according to claim 1, characterized in that the compound has the following formula: Cl 29. The method according to claim 1, characterized in that the compound has the following formula: Cl
Cl 30. The method according to claim 1, characterized in that the compound has the following formula: Cl 31. The method according to claim 1, characterized in that the compound has the following formula: 32. The method according to claim 1, characterized in that the compound has the following formula: Cl gl Cl Process according to claim 1, characterized in that the compound has the formula: Process according to claim 1, characterized in that the compound has the following formula: O- Cl 0 35. The method according to claim 1, characterized in that the compound has the following formula: Cl Cl OCH, 36. The method according to claim 1, characterized in that the compound has the following formula: \\ Cl Cl 37. The method according to claim 1, characterized in that the compound has the following formula: 38. The method according to claim 1, characterized in that the compound has the following formula: Method according to claim 1, characterized in that the compound has the following formula: Cl 40. The method according to claim 1, characterized in that the compound has the following formula: 0 A method of reducing plant moisture loss, characterized by applying to the plant surface an effective amount sufficient to reduce moisture loss from the plant surface without adversely affecting substantially the photosynthetic electron transport, to a compound selected from the following: ^X 10 - ^(Y 19 ^} a (I) (O) ₃ wherein: Rp4 represents a substituted or unsubstituted phenyl, 1- or 2-naphthyl or heteroaryl; X ₁₀ * 0, S, SO, SO ₂ , KH, -CH ₂ O-, -CHgS-, -CH (CH ₃ ) O-, -CH (CIT) O-, -CH = NO-, -C ( CHo) = NO-, -CH ₂ CH ₂ O-, -CHgCHg-, -C = C-, -CHgSO-, -CH ₂ SO ₂ -, -OCH ₂ CH ₂ O-, -CH (alkyl) - or -CONH- represents; j is a value of 0 or 1; a is a value from 2 to 4 inclusive and Y is the same or different and is halogen, alkyl, cyano, polyhaloalkyl, alkoxy, polyhaloalkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, nitro, azyl or polyhaloalkylsulfonyl, provided that (i) at least two ring-position pairs selected from 2 and 4, 2 and 6 and 2 and 3 and 3 and 4 are substituted with the same or different halogen; (ii) R _{2 is} unsubstituted phenyl when ring positions 2, 4 and 6 are substituted with chlorine and j is 0 and X ₁₀ is SO ₂ , and (iii) R _{24 is} not unsubstituted phenyl when Ring positions 2, 3 and 5 are substituted with chlorine, j is a value of 1 and X ₁ Q is S; ^R 25 " (Ii) wherein: R ₂ C represents unsubstituted or substituted phenyl, 1- or 2-naphthyl or heteroaryl; X ₁₁ O »S, SO, SO ₂ , NH, CH ₂ , a single bivalent bond, -GH ₂ O-, -CH ₂ S-, -CH (CH ₃ ) O-, -GH (CH) O-, -CH = NO-, -C (CH ₃ ) = NO-, -CH ₂ CH ₂ O-, -CHgCHg-, -G = C-, -CHgSO-, -CHgSOg, -OCH ₂ CH ₂ O-, - CH represents (alkyl) - or -CONH-; b is a value of 2 to 3 and Y _{20 is the} same or different and represents halogen, alkyl, cyano, polyhaloalkyl, polyhaloalkoxy, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, nitro, azyl or polyhaloalkylsulfonyl, provided that at least two of the Y _{30 are} halogen; X,
^R 26 " ^Z 12 \ / ~ 22 (Iii) Y ₂₃ Bond, -CHgO-, -CHgS-, -CH (GH ₃ ) O-, -GH (CN) O-, -GH = ITO-, -G (CH ₃ ) = N0-, -CH ₂ GH ₂ O- , -CHgCHg-, -C = C-, -CHgSO-, CH ₂ SO ₂ -, -OGH ₂ CH ₂ O-, -CH (alkyl) - or -CONH-; Yg ^ and Y _{22 are} independently the same or different halogen and Yg _{3 represents} hydrogen, halogen, alkyl, polyhaloalkyl, alkoxy, polyhaloalkoxy, cyano, alkylthio, alkylsulfinyl, alkylsulfonyl, nitro, acyl or polyhaloalkylsulfonyl; R ₂₇ - X ₁ (Iv) ^Y 26 ^Y 25 wherein: wherein: R ₂ "represents unsubstituted or substituted phenyl, 1- or 2-naphthyl or heteroaryl; X ₁₃ O, S, SO, SOg, NH, CH ₂ , a single bivalent bond, -CH ₂ O-, -CH ₂ S-, -CH (CH ₃ ) O-, -CH (CN) O-, - CH = NO-, -C (CH ₃ ) = NO-, -CH ₂ CH ₂ O-, -CH ₂ CH ₂ -, -C = C-, -CH ₂ SO-, -OCHgCHg-, -GH (alkyl ) - or -CONH-; Yg. Represents halogen and unsubstituted or substituted phenyl, 1- or 2-naphthyl or heteroaryl; X ₁₂ O, S, SO, SO ₂ , NH, CH ₂ , a single divalent Yg ^ and Y ₂ g are independently hydrogen, halogen, alkyl, polyhaloalkyl, alkoxy, polyhaloalkoxy, cyano, alkylthio, alkylsulfinyl, alkyl sulfonyl, nitrogroup pe, azyl or polyhaloalkylsulfonyl, provided that at least one of Y ₂ , - and Y "6 is halogen, and further provided that Rg ~ is not unsubstituted phenyl when Y ₂ -, Y ₃₅ and Y _g are ghloro and X ^ _ is equal to 0; ' ^R 28 ~ " ^X 14 ^ 28 (V) worm: R _{28 is} unsubstituted or substituted phenyl, 1- or 2-naphthyl or heteroaryl; X ₁₄ O, S, SO, SO ₂ , NH, CH ₂ , a single bivalent bond, -CH ₂ O-, -GHgS-, -CH (CH ₃ ) O-, -CH (CN) O-, -GH = NO-, -C (CH ₃ ) = NO-, -GH ₂ CH ₂ O-, -CHgCHg-, -G = G-, -CHgSO-, -CH ₂ SO ₂ -, -OCH ₂ GH ₂ O- , -CH (alkyl) - or -CONH-; Y ₂ and Ygg are independently halogen and Y ₂ O represents hydrogen, halogen, alkyl, polyhaloalkyl, alkoxy, polyhaloalkoxy, cyano, alkylthio, alkylsulfinyl, alkylsulfonyl, nitro, azyl or polyhaloalkylsulfonyl; (Vi) wherein: R ₂ Q represents unsubstituted or substituted phenyl, 1- or 2-naphthyl or heteroaryl; X _11-0 , S, SO, SO ₂ , NH, CHg, a single bivalent bond, -CH ₂ O-, -CH ₃ S-, -CH (CH ₃ ) O-, -CH (CN) O-, -CH = NO-,.-C (CH ₃ ) = 1TO-, -CH ₂ CH ₂ O-, -CH ₂ CH ₂ -, -C = C-, -CHgSO-, -CHgSOg- -OCH ₂ CH ₂ O-, -CH (alkyl) - or -CONH- represents and YQ, Y ₃₁ and Y ₃₂ independently of one another are hydrogen, halogen, alkyl, cyano group, polyhaloalkyl, alkoxy, polyhaloalkoxy, alkylthio group, alkylsulfinyl, alkylsulfonyl, nitro group, acyl or polyhaloalkylsulfonyl, Z ₃₂ set that at least two of the Y ^ q »Yo ₁ and Y, ₉ halogen (Vii) wherein: R _{o represents} unsubstituted or substituted phenyl, 1- or 2-naphthyl or heteroaryl; X ₁ , 0, S, SO, SO ₂ , NH, CHg, a single bivalent bond, -CH ₂ O-, -CH ₂ S-, -CH (CH ₃ ) O-, -CH (CN) O- , -GH = HO-, -G (CH ₃ ) = NO-, -CH ₂ CH ₂ O-, -CHgCHg-, -C = C-, -CHgSO-, -CHgSOg- -OGH ₂ GH ₂ O-, Represents -CH (alkyl) - or -GONH- and Y ₃₃ , Y ₃ . and Y _{35 are} independently hydrogen, represent alkyl, cyano, polyhaloalkyl, alkoxy, polyhaloalkoxy, alkylthio, alkylsulfonyl, nitro, azyl or polyhaloalkylsulfonyl, provided that (i) at least two of Ϊ33 "Y34 and Y05 'are halogen, (ii) R-, _{o is} not unsubstituted phenyl when Y-. and Y-jE are both ghloro- and X..g is 0, and (iii) Roq is not unsubstituted phenyl or 4-methoxyphenyl, when Y ^ - and Y "both chloro and X ^ g equal O is; ^(Y 36> d (Viii) wherein! d is a value from 0 to 4 inclusive; e is a value of 1 or 2, provided that d + e is not greater than 5; Ri is the same or different and is unsubstituted or substituted aryl, provided that d is not equal to O when R -, ... is 2- or 4-aryl; an alkoxy, cycloalkoxy, aryloxy, aralkoxy group, provided that d is not O when E, an aralkoxy group is arylaryloxy, aralkoxyaralkyl, arylaralkoxy, aryloxyaralkyl, aryloxyalkyl, aryloxyaryloxy, aralkoxyarylkoxy, aryloxyalkoxy, Represents alkylthio, alkenylthio, arylthio, aralkylthio, arylthioaralkyl, arylsulfonylarylsulfonyl, alkylamino, dialkylamino, azyloxy ", aroyloxy, alkoxycarbonyloxy, phenylazo group, provided that Χ ^ γ O or S: maphthylazo group or -OCH ₂ O- or -OGHgCHgO- which join adjacent carbon atoms to form a five- or six-membered ring; Y., g is the same or different and is halogen, alkyl, alkenyl, alkynyl, -GH = CHGH = OH- connecting adjacent carbon atoms to a six-membered ring, - (CH ₂ ) ^, nitro, cyano, haloalkyl or polyhaloalkyl represents; X _{17 represents} 0, S, MH, CH ₂ , -CH ₂ O-, -CHgS- or -OCHgCHgO-; Yyj represents halogen and Y is halogen, an alkoxy, alkylthio, alkylsulfonyl, polyhaloalkoxy, polyhaloalkyl, cyano, nitro or unsubstituted or substituted arylthio, aryloxy or arylsulfonyl group; (Ix) what: f is a We'rt from 0 to 5; Ro _{2 is} identical or different and halogen, alkyl, alkenyl, alkynyl, polyhaloalkyl, cyano, nitro, alkylamino, dialkylamino, alkoxy, polyhaloalkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, polyhaloalkyl sulfonyl, acyl, CO ₂ ( Alkyl), CONH (alkyl), CONUlkyDg, SO ₂ N (alkyl) ₂ , alkylcarbonyloxy, alkoxycarbonyloxy or unsubstituted or substituted aryloxy, arylthio, arylsulfonyl or aroyl; X ₁₈ O, S, GHg represents a single divalent bond or -C = C-; Y is halogen, polyhaloalkoxy, polyhaloalkyl, cyano, alkylsulfonyl, alkylsulfonyloxy, polyhaloalkylsulfonyl or polyhaloalkylsulfonyloxy, and Y.Q represents haloalkyl, polyhaloalkyl, alkoxy group, provided that Xhq is not S or a single divalent bond; a polyhaloalkoxy, cyano, alkylthio group, provided that X..g is not 0 or a single divalent bond; Alkylsulfonyl, nitro group, dialkosphosphinyl or trialkylammonium; "19 jt ^N (X) ^L 42 worxn: Y.sup.1 is the same or different and is halogen; Yp is the same or different and represents halogen, an alkoxy, alkylthio or polyhaloalkoxy group and X _{19 is} 0, -SS, -P (= O) (O-alkyl) -, -P (alkyl-, -P (O-) Alkyl), sulfinyl, sulfonyl, thiosulfinyl, a single divalent bond, carbonyl, atninocarbonylamino, aminooxylylamino, aminocarbonylalkylenecarbonylamino, amino-oalkyleneamino group, unsubstituted or substituted oxyaryloxy group, provided that 1,3-arylene-bisoxy group has at least one Substituted substituents; oxyarylalkylaryloxy, oxyarylthioaryloxy, oxyarylsulfonylaryloxy, and oxyarylaryloxy groups; (Xi) ^Y 53 worxn: Y ^ 2 and Υ, - ^ are independently halogen; g is a value of 0 to 5, inclusive; is the same or different and is halogen, alkyl, alkenyl, alkynyl, polyhaloalkyl, cyano, nitro, amino, alkylamino, dialkylamino, alkoxy, polyhaloalkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, polyhaloalkylsulfonyl, alkoxycarbonyl, alkylaminocarbonyl, aminocarbonyl, Dialkylaminocarbonyl, dialkylaminosulfonyl, alkylaminosulfonyl, aminosulfonyl, alkylcarbonyl, dialkoxyalkyl, alkylcarbonyloxy, alkylcarbonylalkylamino, -CH = GHCH = CH-, linking adjacent carbon atoms to form a six-membered ring, or unsubstituted or substituted aryl, aralkyl, aryloxy, arylthio -, Aralkoxygruppe or arylsulfonyl represents and X _{20 is} -CH (AIlCyI) O-, -C (AIlCyI) ₂ O-, -OCHg-, -CHgO-, -OH ₂ -, -C (halo) ₂ , -OCH ₂ O-, -OCH ₂ CH ₂ O- or -C = C-, provided that g has a fourth of at least 1; -OCH (alkyl) -, -OC (alkyl) ₂ , -OCH (alkyl) O-, -OC (alkyl) gO-, -OCH (alkyl) CHgO-, -OCH (alkyl) CH (alkyl) O-, -CH (alkyl) -CH (alkyl) -, -CH (alkyl) -, -C (AIlCyI) ₂ -, -CHgCHgO-, -OCHgCHg-, -CH (alkyl) CH ₂ 0-, -CH ₂ CHg- , -CH (CN) O-, -C (alkyl) (CN) O-, -CH (polyhaloalkyl) O-, -C (CN) = ITO-, -C (NH-alkyl) = NO-, -O / "N (alkyl)" / = N0-, -C (S-alkyl) = NO-, -C (O-alkyl) = NO-, -SC (= O) O-, -SHC (= O) O -, -N (alkyl) C (= O) O-, SO, SOg, -CHgS (O) -CH (alkyl) S (O) _h -, -S (O) _h CHg-, -OC (= S ) S-, -C (= O) S-, -C (= S) -S-, -NH (alkyl) C (= O) S-, -O (C = O) S-, -N (R ₃₄ ) -, -SO ₂ NH-, -SO ₂ N (AlClyI) -, -CONH-, -CON (alkyl) -, -SC (= O) N (alkyl) -, -SC (= O) NH- , -NHSOgMH-, -N (alkyl) SOgN (alkyl) -, -N (alkyl) SO ₂ NH-, -NHSO _g N (alkyl) -, -C (O-alkyl) = N-, -C (S Alkyl) = N-, -CH (halogen) -, -C (alkyl) (halogen), -CH (CN) -, -C (alkyl) (CN) -, -NH (AlKyI) NH-, -NH -N (alkyl) -, -NH-NH- or -N = N-, provided that R-, o is not a nitro group; -C (= O) -, -C (= O) C (= O) -, -CH (* O-alkyl) -, -CH ₂ C (= O) -, -C (= O) CH ₂ , -CH (alkyl) C (= O) -, -C (= O) CH (alkyl) -, -CH = CH-, -C (alkyl) = CH-, -CH = C (alkyl) -, -C (Alkyl) = C (alkyl) -, -C (= O) CH = CH-, -P (Y ₃ ) (Y ₄ -alkyl) -, unsubstituted or substituted -PiY.oHY -.- aryl) or arylene, -Si (HaIogen) ₂ -, -Si (alkyl) _2, -OC (= 0) N (alkyl) -, -OCH ₂ C (= O) N (alkyl) -, -N (alkyl) CON ( Alkyl), -OC (= O) NH-, -NHCONH-, -SO ₂ NHC (= O) MH- or -NHC (= S) NH, provided that g has a value of at least 1; -CH-CH-, -C (alkyl) -CH-, O O -CH-C (alkyl) or -C (alkyl) -C (alkyl) - O O wherein ta. is a value from 0 to 2 inclusive, R-. Azyl, alkylsulfonyl, polyhaloalkyl, polyhaloazyl, polyalkyloalkylsulfonyl, or unsubstituted or substituted aroyl or arylaulfonyl, and Y ₄₃ and Y _{44 are} independently O or S; ^R 35 ~ ^X 21 (Xii) worxn: R _, - represents an unsubstituted or substituted heterocyclic ring system selected from isoxazole, isothiazole, pyrazole, imidaaol, 1,2,4-triazole, 1,2,4-oxadiazole, 1,3,4-oxadiazole, 1, 2,4-thiadiazole, 1,3,4-thiadiazole, oxazole, thiazole, benzopyrazole, benzimidazole, benzoxazole, benzothiazole, indole, pyrrole, furan, thiophene, benzofuran, benzothiophene, pyridine, pyrimidine, pyridazine, pyrazine, 1,3, 5, -triazine, 1,2,4-triazine, quinoline, isoquinoline, chianzoline, phthalazine, benzopyrazine, benzopyrasine, carbazole, dibenzofuran, debenzothiophene, benzoxazine, phthalimide, benzopyran, dipenzopyridine, pyridopyridine, pyrazolopyrimidine, tetrahydropyrimidinedione, coumarin, piperidine, morpholine , Tetrahydrofuran, tetrahydrothiophene, pyrrolidine, thiomorpholine, piperidin-2-one, piperidine-2,6-dione, 2,5-pyrrolidinedione, 3-horpholinone, 2-oxohexamethyleneimine, 2-oxotetramethyleneimine, 1-pyrazoline, 2-pyrazoline, pyrazolidine , 2-imidazolidinone, 2-imidazolidinethione, 2,4-imidazolidinedione, 1,2-oxathiolane, 1,3- Oxathiolane, 1,3-oxathiane, 1,4-oxathiane, 2 (1H), pyrazinone, 2H-pyran-2-one, 4H-pyran-4-one, 2H-pyran-2-thione, 4H-pyran-4 -thione, tetrahydropyran, tetrahydrothiopyran, 7-0xabicyclo / ~ 2.2.j7heptane, 2-azabicyclo ~ 2.2. * £ Γ \ ϊβ- £ Ϊ3Χΐ, oxetane, coumarin, 1,3-dioxane, 1,4-dioxane or 1, 3-Dioxolan5 X _{21 represents} 0, S or NH, provided that R _{35 is} not pyridine when X ₃₁ is NH, and that R ₃₅ is unsubstituted benzothiazole if X ₂ is Si, and Y.j-.and are independently halogen; ^B 14 ^Y 47 (Xiii) ^ ₃₇ W ₃₈ H ν. (xiv), ^l 47 wherein: R ₃ y and R ₃₈ independently of one another represent halogen, aro-, cyano, polyhaloalkyl, polyhaloalkoxy, alkylsulfonyl, polyhaloalkylsulfonyl, acyl, alkoxycarbonyl, polyhaloalkylsulfonyl or R ₃₉ -X ₂₂ -, provided that only one of R ₃₇ and R ₃₈ is one Time βο ₉ - ^ 22 ^se ^ ⁿ ; group; R ₃ O represents unsubstituted or substituted phenyl, 1- or 2-haphthyl or heteroaryl; X ₂₂ O, S, SO, SO ₂ , CHg, a single bivalent bond, -CH ₂ O-, -CH ₂ S-, -CH (CH ₃ ) O-, -CH (CH) O-, -CH = HO-, -C (CHJ = HO-, -CH ₂ CH ₂ O-, -CHgCHg-, -C = C-, -CHgSO-, -CH ₂ SO ₂ -, -OCH ₂ CH ₂ O-, -CH (Alkyl) - or -COHH-; one of (ii) ₄ and R ₃₈ is R ₃₉ -X ₂ 2 ^iei ' ^{if β} -ιδ is other than R ₃₉ -H', R ₃₉ -AlkVl-H ', R ₃₉ -CC = O) -H, - R _{39 is} -SO ₂ H ', R _{39 is} -O-H' or R _{39 is} -HH-H 'and (iii) R _{g is} not unsubstituted phenyl when R ₃₈ and Y _{47 are} both chloro and X _{32 is} a single divalent bond in the formula (xiii); ¹¹ Il Cl (Xvi) R 15 _R ^R 41 ^R 4 (Xv) wherein: R ₄₁ and R _{42 are} independently halogen or R ₄₃ -X ₂₃ -represented, provided that only one of R ₄₁ and R ₄₂ at a time is R ₄₃ -X ₃₃ ; R _{43 represents} unsubstituted or substituted phenyl, 1- or 2-haphthyl or heteroaryl; X ₂ O 0, S, SO, SOg, CH _{2 is} a single bivalent bond, -CH ₂ O-, CH ₂ S-, -CH (CH ₃ ) O-, -CH (CH) O-, -CH = HO -, -C (CH ₃ ) = HO-, -CH ₂ CH ₂ O-, -CH ₂ CH ₂ -, -C = C-, -CHgSO-, -CHgSOg-, -O Represents halogen and B _{14 represents} 0, S, HH or HR ₄₀ , wherein R _{40 represents} alkyl, alkylsulfonyl, alkenyl, alkynyl, alkoxycarbonyl; unsubstituted or substituted aryl, aralkyl, aryloxy, arylamino, aroyl or arylsulfonyl; provided that (i) both ^{W e B} 14 S ^leicn as well as R ₃₈ something else. Represents -CH (alkyl) - or -COHH- and B., - O, S, MH or HR., Wherein R _{44 is} alkyl, alkylsulfonyl, polyhaloalkylsulfonyl, alkenyl, alkynyl, alkoxycarbonyl; unsubstituted or substituted aryl, aralkyl, aryloxy, arylamino, aroyl or arylaufflonyl; provided that both R ₄₁ and R _{42 are} other than R ₄₃ -X ₂₃ - when B .., - is equal to R ₄₃ -N; H ₄₃ -AlJCyI-N *, R ₄₃ -CKeO) -N *, R ₄₃ -SO ₂ N ;, R ₄₃ -OW; or R ₄₃ -MH-N 'and further provided that one of R ₄₁ and R _{43 is} -N; R _{43 is} alkyl-N; R _{43 is} -CC = O) -N; R ₄₃ -SO ₂ N; , as R ₄₃ -N ;, R ₄₃ -alkyl-1, R ₄₃ -CC = O) -N ;, R ₄₃ -S; R ₄₃ -ON; or R ₄₃ -NH-N; CXVII) (Xviii) wherein; R j, R w-> R ₄₇ and R _{48 are} independently hydrogen, nitro, cyano, polyhaloalkyl, polyhaloalkoxy, alkylsulfonyl, polyhaloalkylsulfonyl, acyl, alkylthio, alkyl, alkoxy, alkylsulfonyl or RQX ₂₄ , provided that one of R ₄ ^ R ₄₇ and R ₄ R _{40 is} -X ₂₄ , and further provided that R 1 c, R ¹ ig R 4 .7 ¹ d R i -i each contain no more than two hydrogen, alkyl or alkoxy group at a time; R ₄ g represents unsubstituted or substituted phenyl, 1- or 2-naphthyl or heteroaryl; X ₂₄ O, S, SO, SO ₂ , CH ₂ , a single bivalent bond, -CH ₂ O-, -CH ₂ S-, -CH (CH ₃ ) O-, -CH (CN) O-, -CH = NO-, -C (CH ₃ ) = NO-, -CH ₂ CH ₂ O-, -CH ₂ CH ₂ -, -C = C-, -CHgSO-, -CH (alkyl) - or -CONH- represents ; Y _{48 represents} halogen and
B ₁ c represents 0, S or NH; 0 * 54 -'Sir, N - (" wherein: ^J 17 ^L 55 (Xix) R ₁ -Q represents an unsubstituted or substituted, carbocyclic or heterocyclic ring system selected from a monocyclic aromatic or nonaromatic ring system, a bicyclic aromatic or nonaromatic ring system, a cyclic aromatic or nonaromatic ring system, and a bridging ring system which may be saturated or unsaturated; B ₁₇ -CH = N-, -N = CH-, -CH = CH-, -CO-, -SOg-, -CHgCO-, -COCHg-, -COM-, -NHCO-, -SO ₂ NH-, NHSO ₂ -, -SO ₂ N (AIlCyI) -, -U (Al-) kyl) SO ₂ -, -OSO ₂ -, -OS-, -N ^, -MH-, -H (alkyl) -, -O-SC ₂ -, -HHCH ₂ -, -H (alkyl) CH ₂ - , -SCO-, -OCHg-, -OCO-, -CH ₂ -, -CH ₂ CH ₂ - or -SCHgCO-, provided that the phenyl is substituted when Β..γ is -CO- and RcQ is phenyl is and Y ₅₄ and Y, -, - are independently halogen;   worm: R _{51 represents} an unsubstituted or substituted, 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 bridging ring system which may be saturated or unsaturated; B ₁₈ -CH = H-, -M = CH-, -CH = CH-, -CO-, -SOg-, -CHgCO-,., - COCH ₂ -, -COMH-, -MHCO-, -SOgNH- , -HHSO ₂ -, -SOgN (alkyl) -, -M (AIlCyI) SO ₂ -, -OSOg-, -CS-, -N ^, -MH-, -N (alkyl) -, -OCHg-, - represents ₀ or -SCH CO- SCH ₂ -, -HHCH ₂ -, -N (alkyl) CHg, -S-CO-, -OCHg-, -OCO-, -CH - -, -CH CH _{0 0;} R _{19 is} -CHg- or -CH (alkyl) - and i is 0 or 1 and and are independently halogen; (Xxi) wherein: B ₂₀ -CH ₂ C (CH) ₂ SCH ₂ -, -CH ₂ CH = C (CH ₃ ) OCH ₂ -, -C (CH ₃ ) -, -CH ₂ CH ₂ SCH ₂ CH ₂ -, -CH ₂ SCH ₂ CO-, -COCH ₂ C (CH ₃ ) ₂ CH ₂ CO-, -COCH ₂ CH (C ₆ H ₅ ) CH ₂ CO-, -COm (CgH ₅ ) CHgCHgCO-, -000 (0 ^) ^ 00-, -CH ₂ CH ₂ II (C ₆ H ₅ ) CH ₂ CH ₂ -, -CH ₂ H (C ₆ H ₅ ) CH ₂ CH ₂ , -CH ₂ CH ₂ CH (C ₆ H ₅ ) CH ₂ CH ₂ -, -CO (CH ₂ ) ₃ CO-, -C0 (CH ₂ ) ₂ C0-, -COCH ₂ CH (CH ₃ ) Ch ₂ CO-, -COCH (CH ₃ ) CH ₂ CO-, -COC (CH ₃ ) ₂ CH ₂ CO-, -COC (CH ₃ ) ₂ C (CH ₃ ) ₂ CO-, -CO (CH ₄ ) ₄ CO-, -CO (CH ₂ ) ₅ CO-, -CO (CH ₂ ) ₅ CH ₂ -, -C0 (CH ₂ J ₄ CH ₂ -, -CO (CHg) ₃ CHg-, -CO (CHg) ₂ GH ₂ - -COCH ₂ SCH ₂ CO-, -COCH ₂ M (R ₅₂ ) CH ₂ CO-, -COCHgOCHgCO-, -COCH ₂ SCS-, -COCH = CH = M = CH-, -CH ₂ CH (C ₆ H ₅ ) CH ₂ -M = CH- or -CO ₂ -CH ₂ CH ₂ represents; R _{52 is} hydrogen, alkenyl; unsubstituted or substituted aryl or alkaryl, and Y ₅₈ and are independently halogen; ¹ GO (Sxii) wherein: R ₅₃ unsubstituted or substituted cycloalkenyl, cycloalkadienyl, cycloalkatrienyl, bicyclicalkyl, bicyclic alkenyl, bicyclicadienyl, tricyclicalkyl, tricyclic alkenyl nyl or Trizykloallcadienyl, wherein the permissible substituents are the same or different and one or more of the following: alkyl, halogen, haloalicyl, polyhaloalkyl, alkoxy, alkylthio, alkylsulfonyl, polyhaloalkoxy, nitro, cyano, acyl, aroyl, aryl, alkoxycarbonyl Alkoxy-carbonyloxy, azyloxy, oxo group or -GH = GHGH = CH- or -CH = CHGH ₂ - linking adjacent carbon atoms to form a six- or five-membered ring; and are independently halogen and X represents O, S, NH, CH ₂ , -CHO- or a single divalent bond; (Xxiii) H H wherein; R, -. is the same or different and one or more of the following is hydrogen, halogen, alkyl, aryl, aralkyl, alkenyl, alkynyl, polyhaloalkyl, KH ₂ , NH (alkyl), N (alkyl) ₂ , alkoxy, polyhaloalkoxy, alkylthio, alkylsulfonyl , Alkylsulfinyl, aralkoxy, COgAlkyl, CONH (alkyl), COBH ₂ , CON (alkyl) _2> SO ₂ H (AIlCyI) ₂ , SO ₂ NH (alkyl), SOgNHg, azyl, C0 (0-allcyl) _2> azyloxy group, Azyl-CON (alkyl) or 2,3 - (- CH = CHCH = CH-), 3,4 - (- CH = GHCH = CH), 2,3- (CH ₂ ) .- or 3,4- ( CH ") .- connecting the adjacent carbon atoms to form an unsubstituted or substituted six-membered ring; Xgg O, S, SO, SOg, CH ₂ , a single bivalent bond, -GH ₂ O-, -CH ₂ S-, -CH (CH ₃ ) O-, -CH (CN) O-, CH = NO- , -C (CH ₃ ) = NO-, -CH ₂ CH ₂ O-, -CH ₂ CH ₂ -, -C = C-, -CHgSO-, -CH ₂ S -OCH ₂ GH ₂ O-, -OCH _{2 is} CH ₂ - or -OCH ₂ and Y _{1 are the} same or different and are halogen; (Xxiv) wherein: R, -; ·, unsubstituted or substituted phenyl or 1- 00
or 2-haphthyl; X _{27 is} -CH (alkyl) O-, -C (alkyl) ₂ O-, -OCHg-, -G (halo) ₂ , -OCH ₂ O-, -OCH ₂ GH ₂ O-, -CHgO-, -C = C-, -OCH (alkyl) -, -OC (alkyl) ₂ , -OCH (alkyl) O-, -OC (alkylJgO-, -OCH (alkyl) CH ₂ O-, -OCHtAlkyDCHiAlkyDO-, -CH (alkyl ) CH (alkyl) -, -CH (alkyl) -, -C (alkyl) ₂ -, -GH ₂ GH ₂ O-, -OCH ₂ CH ₂ -, -GH (alkyl) CH ₂ O-, -CH ₂ CH ₂ -, -CH (CN) O-, -C (AIlCyI) (CN) O-, -CHiPolyhaloalkyDO-, -C (GN) = NO-, -C (IIH alkyl) = NO-, -C / ~ N (alkyl ) ₂ J = NO-, -C (S-alkyl) = HO-, -G (O-alkyl) = NO-, -SG (= O) O-, -HHG (= O) O-, -N (alkyl) G (= O) O-, SO, SO ₂ , -CHgS (O) ₁₁ -, -CH (alkyl) S (O) _h , -S (O) ₁₁ GH ₂ -, -OC ( = S) -, -G (= O) S-, -G (= S) -S-, -NH (allcyl) C (= O) S, -O (C = O) S-, -N (alkyl ) -, -N (R ₃₄ ) -, -SOgNH-, -SO ₂ N (alkyl) -, -CONH-, -CON (alkyl) -, -SC (= O) N (allcyl) -, -SG ( = O) NH-, -NHSO ₂ NH-, -N (alkyl) SO ₂ N (alkyl) -, -N (alkyl) SO ₂ NH-, -1-ISO ₂ N (alkyl) -, -N (alkyl ) SO ₂ NH-, -NHSO ₂ N (AIlCyI) -, -C (O-alkyl) = N-, -G (S-alkyl) = H-, -CH (halo) -, -C (alkyl) ( Halogen) -, -CH (CN) -, -C (alkyl) (CN) -, -NH (AllCyI) NH-, -NH-N (allcyl) -, -BH-MI-, -Ii = N-, -C (= 0) -, -C (= 0) 0 (= 0 ) -, -CH (O-alcyl) -, -CH ₂ C (= O) -, -C (= O) GH _2> -CH (allcyl) G (= O) -, -O (= O) CH (Alkyl) -, -CH = GH-, -C (alkyl) = CH-, -CH = C (AIlCyI) -, -C (alkyl) = C (alkyl}, -G (= O) GH = CH-, P (Y ₄₃₎ (Y. alkyl.) -, unsubstituted or substituted -P (Y ₄₃ ) (Y ₄₄ -aryl) or arylene, -Si (halogen) ₂ -, -Si (alkyl) ₂ S -OC (.O) N (alkyl) -, -OCH ₂ C (= OKalkyl) -, -N (alkyl) -CON (alkyl) -, -OG (= O) NH-, -NHCOm-, -SO ₂ NHG (= O) NH-, -HHC (= S) HH-, -GH-CH-, -C (AIlCyI) -CH-, -CH-C (AllCyI) - or 0 0 0 -C (alkyl) -C (alkyl) - represents, wherein h is a value from 0 to 2 inclusive, R 1 represents " azyl, alkylsulfonyl, polyhaloalkyl, polyhaloazyl, polyhaloalkylsulfonyl or unsubstituted or substituted arylsulfonyl, and Y. and Y. are independently O or S; Z * and Zp are independently O, S, Cj-Cg-alkylidene, substituted or unsubstituted benzylidene, HH or 'HR ¹ ', where R ¹ 'is alkyl, aryl, aralkyl, alkenyl or alkynyl and Y _c "and Y _{Cq are} identical or different and are hydrogen, halogen, alkyl, cyano group, polyhaloalkyl, alkoxy, polyhaloalkoxy group, haloalkyl, alkylthio group, alkylsulfinyl, alkylsulfonyl, nitro group, aryl, polyhaloalkylsulfonyl, alkylamino, dialkylamino, azylamino, Azyloxy, alkylsulfonyloxy, arylsulfonyloxy, alkenylsulfonyloxy, haloalkylsulfonyloxy, polyhaloalkylsulfonyloxy, phosphono or phosphino group; 17 ν ^Λ 3 69
/ "Γ r \ - (Xxv) "• 70 Rg represents unsubstituted or substituted phenyl or 1- or 2-haphthyl; equal to HH, or a divalent bond; Zj and Z. independently of one another are O , S, C. ~ Co-alkylidene, substituted or unsubstituted benzylidene, HH or HR '", where R ¹ " is alkyl, aryl, aralkyl, alkenyl or alkynyl and YgO and Y "q are the same or different and are hydrogen, halogen, alkyl, cyano, polyhaloalkyl, alkoxy, polyhaloalkoxy, haloalkyl, alkylthio, alkylsulfinyl, alkylsulfonyl, nitro, aryl, polyhaloalkylsulfonyl, .alpha.-alkylamino, dialkylamino, azylamino, azyloxy -, alkylsulfonyloxy, arylsulfonyloxy, Alekynlsulfonyloxy-, Haloalkylsulfonyloxy-, Polyhaloalkylsulfonyloxy-, phosphono, phosphino are, under the condition that YgQ and. Y _"Q together v / ground the same halogen or halogens and hydrogen; ^R 70 ~ ^X 29 ~ ^H '(xxvi) worxn: wherein: R _{70 represents} an unsubstituted or substituted, saturated or unsaturated, aromatic or non-aromatic heterocyclic ring system selected from isoxazole, isothiazole, pyrazole, imidazole, 1,2,4-triazole, 1,2,4-oxadiazole, 1,3 4-oxadiazole, 1,2,4-thiadiazole, 1,3,4-thiadiazole, oxazole, thiazole, benzopyrazole, benzimidazole, benzoxazole, benzothiazole, indole, pyridine rol, furan, thiophene, benzofuran, benzothiophene, pyridine, pyrdtoidine, pyridazine, pyrazine, 1,3,5-triazine, 1,2,4-triazine ₉ quinoline, iaoctiinoline, cttinazoline, phthalazine, benzopyridazine, benzopyrazine, carbazole, dibenzofuran, Dibenzothiophene, benzoxazine, phthalimide, benzopyran, dibenzopyridine, pyridopyridine, pyrazolopyrimidine, tetrahydropyrimidinedione, piperidine, morpholine, tetrahydrofuran, tetrahydrothiophene, pyrrolidine, thiomorpholine, piperidine-2-one, piperidine-2,6-dione, 2,5-pyrrolidinedione, 3-morpholinone, 2-0xohexaethyleneimine, 2-0xotetrarnethyleneimine, 1-pyrazoline, 2-pyrazoline, pyrazolidine, 2-imidazolidione, 2-imidazolidinethione, 2,4-imidazolidinedione, 1,2-oxathiolane, 1,3-oxathiolane, 1,3-oxathiane, 1,4-oxathiane, 2 (1H) -pyrazinone, 2H-pyran-2-one, 4H-pyran-4-one, 2H-pyran-2-thione, 4H-pyran-4-thione, tetrahydropyrane, tetrahydrothiopyran , 7-0xabicyclo / ~2.2.J_7 heptane, 7-azabicyclo- / ~ 2.2. _i 1_7heptane, oxetane,! coumarin, 1,3-dioxane, 1,4-dioxane or 1,3-dioxolane; X _2g represents -CH (alkyl) O-, -C (AIlCyI) ₂ O-, -OOHg-, -CHO-, -CHg-, a bivalent bond, -C (halo) ₂ , -OCH ₂ O. -, -OCH ₂ CH ₂ O-, -C = C-, -OCH (alkyl) -, -O (alkyl) _2> -OCH (alkyl) O-, -OC (alkyl) gO-, -OCHiAlkyDCHgO-, -OCH (alkyl) CH (alkyl) O-, -CH (alkyl) CH (alkyl) -, -CH (alkyl) -, -C (alkyl) g-, -CH ₂ CH ₂ O-, -OCH ₂ CH ₂ -, -ClKalkyiOCHgO-, -CH ₂ CH ₂ -, -CH (ClOO-, -C (alkyl) (CH) O-) , -CH (polyhaloalkyl) 0-, -C (CN) = NO-, -C (BH alkyl) -C = NO- _J / ~ N (alkyl) ₂ _7 = H0-, -C (S-alkyl) = NO-, -C (O-alkyl) = NO-, -SC (= O) O-, -UHC (= O) O-, -N (alkyl) C (= O) O-, SO, SOg-, -CHgS (O) _h -, -CH (alkyl) S (O) _h , -S (0) _h CH ₂ -, -OC (= S) S-, -C (= O) S-, -C ( = S) (- S-, -NH (alkyl) C (= O) S-, -O (C = O) S-, -NH-, -N (alkyl) -, -N (R ₃₄ ) -, -SOgMH-, -SO ₂ N (alkyl) -, -COHH-, -CON (alkyl) -, -SC (= O) H (alkyl) -, -SC (= O) MH-, -NHSO ₂ NH- , -N (alkyl) SO ₂ H (alkyl) -, -N. (Alkyl) SOgMH-,'HHSO ₂ N (alkyl) -, -C (O-alkyl) = H-, -C (S-alkyl) = N-, -CH (halo) -, -C (alkyl) (halo) -, -CH (CN) -, -C (AIlCyI) (CH) -, -MH (alkyl) NH-, -NH-N (Alkyl) -, -NH-HH-, N = N-, -C (= O) -, -C (= O) C (= O) -, -CH (O-alkyl) -, -CHgC (= O) -, -C (= O) CH ₂ , -CH (alkyl) = CH-, CH (alkyl) C (= O) -, -C (= O) CH (alkyl) -, -CH = CH- , -CH = C (alkyl) -, -C (alkyl) = C (alkyl) -, -C (= O) CH = CH-, L) -, unsubstituted o the substituted -P (Y ₄₃ ) (Y ₄₄ -ArYl) or arylene, -Si (halo, -Si (alkyl) ₂ , -CO (= O) N (alkyl) -, -OCH ₂ C (= O ) N (alkyl) -, -H (alkyl) CON (A1-kyl) -, -OC (= O) NH-, -HHCONH-, -SO ₂ HHC (= O) HH-, -NHC (= S) HH-, -CH-CH-, -C (AIiCyI) -CH-, -CH-C (AllCyI) - or -C (alkyl) -C (Al-) 0 0 0 0 wherein h is a value of 0 to 2 inclusive, R _{4 is} azyl, alkylsulfonyl, polyhaloalkyl, polyhaloazyl, polyhaloalkylsulfonyl or unsubstituted or substituted aroyl or arylsulfonyl, and Y ₄₃ and Y _{44 are} independently 0 or S; Zp and Zg are independently 0, S, Cj-Cg-alkylidene, substituted or unsubstituted benzylidene, HH or NR ¹ ", wherein R ¹ " is alkyl, aryl, aralkyl, alkenyl or alkynyl, and. . ,,., And Y " ₂ same or different airid and. Is hydrogen, halogen, alkyl, cyano group, polyhaloalkyl, alkoxy, polyhaloalkoxy, haloalkyl, alkylthio, alkylsulfinyl, alkylsulfonyl, nitro, azyl, polyhaloalkylsulfonyl, amino, alkylamino, dialkylamino, azylamino, azyloxy, alkylsulfonyloxy, arylsulfonyloxy, Alkenylsulfonyloxy, haloalkylsulfonyloxy, polyhaloalkylsulfonyloxy, alkoxycarbonyl, alkylaminocarbonyl, atninocarbonyl, dialkylaminocarbonyl, dialkylaminosulfonyl, dialkoxyalkyl, alkylaminosulfonyl, aminosulfonyl, arylsulfonyl, phosphono or phosphino; .R ₇₁ -X ₃₀ -N wherein: (Xxvii) "74 R ₇₁ unsubstituted or substituted allyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkadienyl, cycloalkyl, alkatrienyl, bicyclicalkyl, bicyclickenyl, bicyclicadienyl, tricyclicalkyl, tricycloalkenyl or tricycloalkadienyl; X ₃₀ -CH (alkyl) O-, -C (AIlCyI) ₂ O-, -OCHg-, -CHgO-, -CHg-,. a bivalent bond, -C (halogen) g, -OCHgO-, -OCH ₂ CHgO-, -C = C-, -OCH (alkyl) -, -OC (alkyl) g, -OCH (alkyl) 0-, - OC (AlClyI) ₂ O-, -OCH (AIlCyI) CH ₂ O-, -OCH (alkyl) CH (alkyl) O-, -CH (alkyl) CH (alkyl) -, -CH (AIlCyI) -, -C (Alkyl) ₂ -, -CH ₂ CH ₂ O-, -OCH ₂ CH ₂ -, -CH (AIlCyI) CHgO-, -CHgCHg-, -CH (CH) O-, -C (AIlCyI) (CH) O -, -CHiPolyhaloalkyDO-, -C (CH) = HO-, -C (HH alkyl) = H0-, -C / "N (alkyl) g_7 = H0-, -C (S-alkyl) = HO-, - C (O-alkyl) = H0-, -SC (= O) O-, -HHC (= O) O-, -K (alkyl) C (= O) O-, SO-, SOg, -CHgS (O ) _h , -CH (AlClyI) S (OJj ₁ -, -S (O) _h CHg-, -OC (= S) S-, -C (= O) S-, -C (= S) -S-) , -KH (alkyl) C (= O) S-, -O (C = O) S-, -HH-, -H (alkyl) -, -H (R ₃₄ ) -, -SOgHH-, -SOgH ( Alkyl) -, -COKH-, -COH (AllCyI) -, -SC (= O) H (alkyl) -, -SC - (= O) HH-, -HHSOgHH-, -H (alkyl) SOg-H ( Alkyl) -, -H (AIlCyI) SOgInI-, -NHSOgHiAlkyl) -, -C (O-alkyl) = K-, -C (S-alkyl) = H-, -CH (halo) -, -C (alkyl ) (Halogen) -, -CH (CH) -, -C (AIlCyI) (CH) -, -HH (alkyl) HH-, -HH-H (AIlCyI) -, -M-KH-, -K = K -, -C (= O) -, -C (= O) C (= O) -, -CH (O-AlClyI) -, -CHgC (= O) -, -CC = O) CHg, -CH ( Alkyl) C (= O) -, -C (= O) CH (alkyl) - , -CH = CH-, -C (alkyl) = CH-, -CH = C (alkylJ-, -C (alkyl) = C (alkyl) -, -C (= O) CH = CH-, -P ( Y ₄₃ ) (Y ₄₄ alkyl), unsubstituted or substituted -P (Y ₄₃ ) (Υ -, - aryl) or arylene, -Si (halo) ₂ -, -Si (alkyl) g, -OC (= 0 ) K (alkyl) -, -OCHgC (= O) K (alkyl) -, -K (alkyl) COK (alkyl) -, -00 (= 0) HH-, -KHCOKH-, -SOgHHC (= 0) KH -, -KHC (= S) KH, -CH-CH-, -C (AIlCyI) -CH-, -CH-C (AIlCyI) - or 0 0 0 -C (alkyl) -C (alkyl) -, where h is a value from 0 to 2 inclusive, R-. Azyl, alkylsulfonyl, polyhaloalkyl, polyhaloazyl, polyhaloalkylsulfonyl or unsubstituted or substituted aroyl or arylsulfonyl, and Y ₄₃ and Y _{44 are} independently 0 or S; Ζγ and Z _{8 are} independently 0, S, C 1 -C 8 substituted or unsubstituted benzylidene, HH or WR "'where R'" is alkyl, aryl, aralkyl, alkenyl or alkynyl ; and Y "_ and Y ₇ . are the same or different and are hydrogen, halogen, alkyl, cyano, polyhaloalkyl, alkoxy, polyhaloalkoxy, haloalkyl, alkylthio, alkylsulfinyl, alkylsulfonyl, hitro, aryl, polyhaloalkylsulfonyl, alkylamino, dialkylamino, acylamino, acyloxy, alkylsulfonyloxy , Arylsulfonyloxy, alkenylsulfonyloxy, haloalkylsulfonyloxy and polyhaloalkylsulfonyloxy group; 75 (Xxviii) wherein: Bg ₁ -CH ₂ C (CH ₃ ) ₂ SCHg, -CH ₂ CH = C (CH ₃ ) OCHg, -CHgCHgSCHgCH (CH ₃ ) -, -CH ₂ CH ₂ SCH ₂ CHg-, -CH ₂ SCHgCO- , -COCHgC (CH ₃ ) gCHg CO-, -COCH ₂ CH (C ₆ H ₅ ) CHgCO-, -COlIH (C ₆ H ₅ ) CH ₂ CH ₂ O-, -COC (CH ₃ ) ₂ iIHCO-, CH ₂ CH ₂ Ii (C ₆ H ₅ ) CHgCHg-, -CHgH (C ₆ H ₅ ) CHgCHg-, -CH ₂ CH ₂ CH (C ₆ H ₅ ) CH ₂ CH ₂ -, -co (cii ₂ ) ₃ co-, -co (ch ₂ ) ₂ co-, -GOCK (CH ₃ ) CH ₂ CO-, -COG (GH ₃ ) _{232 32} -GOC (CH ₃ ) gC (CH ₃ ) g CO-, -CO (CH ₂ ) ₄ CO-, ₃ ) g ₂ ) ₄ C ₃ g ₃ g, ₂₄ , (g) ₅ -CO (CHg) ₅ GH ₂ -, -GO (CHg) ₄ CH ₂ -,. -CO (CHg) ₃ CH ₂ -, -g ₂₂ -COGH ₂ SGH ₂ CO-, -COCH ₂ N (R ₅₂ ) GH ₂ CO-, -GOGH ₂ OCH ₂ CO-, -COCH ₂ SCS-, -COCH = CH-Ii = CH-, -GH ₂ Ch (C ₆ HS) CH ₂ -II = CH- or -COg-CHgCHg, where R _{52 is} hydrogen, alkenyl; unsubstituted or substituted aryl or alkyl-ryl; Zq and Z.JQ are independently 0, S, C 1 -C 6 alkylidene, substituted or unsubstituted benzylidene, HH or NR ", where R 'is" alkyl, aryl, aralkyl, alkenyl or alkynyl ", and Y ₇₅ and Y "g are the same or different and Is hydrogen, halogen, alkyl, cyano group, polyhaloalkyl, alkoxy, polyhaloalkoxy, haloalkyl, alkylthio, alkylsulfinyl, alkyl-3-sulfonyl, hitro, azyl, polyhaloalkylsulfonyl, amino, alkylamino, dialkylamino, azylamino, acyloxy, alkylsulfonyloxy, arylsulfonyloxy Alkenylsulfonyloxy, haloalkylsulfonyloxy, polyhaloalkylsulfonyloxy, phoaphono or phosphino group; 77 (Xxix) wherein: R _{72 is} unsubstituted or substituted phenyl or bland 2-naphthyl; S ^ ₁ -OCH ₂ -, -CH ₂ -, a divalent bond, -G (halo) ₂ , -C = G-, -OGH (alkyl) -, -OC (alkyl) ₂ , -CH (alkyl) GH (Alkyl) -, -CH (alkyl) -, -G (alkyl) ₂ -, -OCHgCHg-, -CHgCIig, SO, -S-, SO ₂ , -CH ₂ S (O) ₁₁ -, -CH ( Alkyl) S (O) _h -, -S (O) _h CHg-, -CH (halo) -, -G (alkyl) (halogen), -GH (CH) -, -C (alkyl) (GN) - or -C (= O) -, -CH (O-alkyl) -, -CHgC (= O) -, -C (= O) CHg, -CH (alkyl) G (= O) -, -G (= O) CH (alkyl) -, -CH = CH-, -C (alkyl) = CH-, -CH = C (alkyl) -, -G (alkyl) = G (alkyl) -, -C (= O) CH = CH-, arylene, -Si (halogen) ₀ -, -Si (alkyl) _o , -CH-CH-, -C (alkyl) -CH-, 0 0 -GH-C (alkyl) - or -C (alkyl) -C- (alkyl) -; where h is a value from 0 to 2 inclusive; Z _{11 represents} 0, S, C 1 -C 6 -alkylidene, substituted or unsubstituted a benzylidene, NH or HR ¹ "wherein R" is alkyl, aryl, aralkyl, alkenyl or alkynyl, and Y ₇₇ , Yrja and Y ^ n are the same or different and are hydrogen, halogen, alkyl, hydroxy, cyano, polyhaloalkyl, alkoxy, polyhaloalkoxy, haloalkyl, alkylthio, alkylsulfinyl, alkylsulfonyl, nitro, acyl, polyhaloalkylsulfonyl, alkylamino , Amino, dialkylamino, azylamino, azyloxy, alkylsulfonyloxy, arylsulfonyloxy, alkenylsulfonyloxy, haloalkylsulfonyloxy, polyhaloalkylsulfonyl oxy, phosphorus or phosphino group, with the proviso that Y _{73 is} not an amino, alkylaiaino, dialkylamino - or Azylaminogruppe can be when Y _{77 is} halogen and Y _{70 is} hydrogen, and among the other Condition that Υ, ™ can not be hydrogen or a hydroxy group when Y "" and Y " _{o are} the same halogen; R ₇₃ -X ₃₂ -H (Xxx) wherein: R "represents an unsubstituted or substituted, saturated or unsaturated, aromatic or non-aromatic, heterocyclic ring system selected from isoxazole, isothiazole, pyrazole, imidazole, 1,2,4-triazole, 1,2,4-oxadiazole, 1, 3 "4-oxadiazole, 1,2,4-thiadiazole, 1,3,4-thiadiazole, oxazole, thiazole, benzopyrazoles, benzimidazole, benzoxazole, benzothiazole, indole, pyrrole, furan, thiophene, benzofuran, benzothiophene, pyridine, pyrimidine, pyridazine , Pyrazine, 1,3,5-triazine, 1,2,4-triazine, ghinoline, isoquinoline, quinazoline, phthalazine, benzopyridazine, benzopyrazine, carbazole, dibenzofuran, dibenzothiophene, benzoxazine, phthalimide, benzopyran, bibenzopyridine, pyridopyridine, pyrazolopyrimidine, tetrahydropyrimidinedione , Piperidine, morpholine, tetrahydrofuran, tetrahydrothiophene, pyrrolidine, thiomorpholine, piperidin-2-one, piperidine-2,6-dione, 2,5-pyrrolidinedione, 3-morpholinone, 2-oxohexamethyleneimine, 2-oxotetramethylene-imine, 1-pyrazoline , 2-pyrazoline, pyrazolidine, 2-imidazolidine on, 2-imidazolidinethione, 2,4-imidizolidinedione, 1,2-oxathiolane, 1,3-oxathiolane, 1,3-oxathiane, 1,4-oxathiane, 2 (1H) -pyrazinone, 2H-pyran-2-one , 4H-pyran-4-one, 2H-pyran-2-thione, 4H-pyran-4-thione, tetrahydropyran, tetrahydrothiopyran, 7-oxabicyclo / "2.2. Ij _1- ZhGPtBn, 7-azabicyclo- /" 2.2.JjHePtBn , Oxetane, coumarin, 1,3-dioxyn, 1,4-dioxane or 1,3-dioxolane; 32 "OöHg-i -CHg-, a divalent bond, -C ^ -C = C-, -OCH (alkyl) -, -OC (AllCyI) ₂ -, -CH (alkyl) CH (alkyl) -, -CH (AIlCyI) -, -C (AllCyI) ₂ -, -OCHgCHg-, -CH ₂ CH ₂ -, SO, -S-, SO ₂ , -CH ₂ S (O) _h -, -CH (alkyl) S ( 0) _h -, -S (O) _h CH ₂ -, -CH (halo) -, -C (alkyl) (halogen) -, -CH (CH) -, -C (alkyl) (CH) -, - C (= O) -, -CH (O-alkyl) -, -CH ₂ C (. = O) -, -C (= O) CH ₂ , -CH (alkyl) C (= O) -, -C (= O) CH (alkyl) -, -CH = CH-, -C (alkyl) = CH-, -CH = C (alkyl) -, -C (alkyl) = C (alkyl) -, -C (= O) CH = CH-, arylene, -Si (halogen) ₂ -, -Si (alkyl) ₂ -, -CH-CH-, -C (alkyl) -CH-, Is -CH-C (alkyl) - or -C (alkyl) -C (alkyl) -; ⁰ 0 - where h is a value of 0 to 2 inclusive; Ζ .., O, S, C ^ -Co-alkylidene, substituted or unsubstituted benzylidene, HH or HR "', where R"' is alkyl, aryl, aralkyl, alkenyl or alkynyl, and YgQ, Y ₈₁ and Ynp are the same or different and are hydrogen, halogen, alkyl, hydroxy, cyano, polyhaloalkyl, alkoxy, polyhaloalkoxy, haloalkyl, alkylthio, alkylsulfinyl, alkylsulfonyl, mitro, azyl, polyhaloalkylsulfonyl, alkylamino, amino, Dialkylamino, azylamino, azyloxy, alkylsulfonyloxy, arylsulfonyloxy, Alkenylsulfonyloxy, haloalkylsulfonyloxy, polyhaloalkylsulfonyloxy, phoaphono or phosphino group; Y ₈₃ R ₇ . unsubstituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkadienyl, cycloalkatrienyl, bicyclicalkyl, bicyclickenyl, bicyclicadyl, tricyclic, tricycloalkenyl or tricyclicycadienyl; X "_ -OCH ₂ -, -CH ₂ -, a bivalent bond, -C (halogen) ₂ , -C = C-, -OCH (alkyl) -, -Oc (alkyl) ₂ , -CH (alkyl) CH (Alkyl) -, -CH (alkyl) -, -C (alkyl) ₂ -, -OCH ₂ CH ₂ -, -CHgCHg-, SO, -S-, SO ₂ , -CH ₂ S (O) ₁₁ -, -CH (alkyl) S (O) _h -, -S (O) _h CH ₂ -, -CH (halo) - _} -C (alkyl) (halo) -, -CH (CN) -, -C (alkyl ) (CN) - or -C (= O) - ₉ -CH (O-alkyl) -, -CH ₂ C (= O) -, -C (= O) CH _2> -CH (alkyl) C (= O) -, -O (= O) CH (alkyl) -, -CH = CH-, -C (alkyl) = CH-, -CH = C (AIlCyI) -, -C (alkyl) = C (alkyl ) -, -C (= O) CH = CH-, arylene, -Si (halo) ₂ -, -Si (alkyl) ₂ -, -CH-CH-, -C (alkyl) -CH-, 0 0 Is -CH-C (alkyl) - or -C (alkyl) -C (alkyl) -; 0 p where h is a value from 0 to 2 inclusive; benzylidene, Iffl or WR ¹ ", wherein R ¹ " is alkyl, aryl, aralkyl, alkenyl or alkynyl, and Y ₈₃ , Yq ₄ and Yg 1 are the same or different and are hydrogen, halogen, alkyl, hydroxy, cyano, polyhaloalkyl, alkylthio, alkoxy, polyhaloalkoxy, haloalkyl, alkylsulfinyl, alkylsulfonyl, eggitro, acyl, polyhaloalkylsulfonyl, alkylamino, amino , Dialkylamino, acylamino, azyloxy, alkylsulfonyloxy, arylsulfonyl oxy, alkenylsulfonyl oxy, haloalkyl sulfonyl oxy or polyhaloalkylaulphonyonyx; wherein the permissible substituents for the above-mentioned formulas (i) to (i) are the same or different and one or more of the following: hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylallcyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, quioiozyanoano, propargylthio , Hydroximino, alkoxyimino, quirialkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxy, iormaniidino, alkylsulfamido, dialkylaulamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyi, nitro, cyano , Hydroxy carbonyl and derived salts, iodomamido group, alkyl, alkoxy group, polyhaloalkyl, polyhaloalkoxy group, alkoxy carbonyl, substituted amino group in which the permissible substituents are the same or different and one or two of the following: propargyl, alkoxyalkyl, alkylthioalkyl, alkyl, alkenyl, Hal oalkenyl or polyhaloalkenyl; Alkylthio, polyhaloalkylthio group, alkylsulfinyl, polyhaloalkylsulfonyl, alkylsulfonyl, polyhaloalkyl O, S, Cj-Cg-alkylidene, substituted or unsubstituted sulfonyl, alkylsulfonylamino, alkylcarbonylamino, polyalkylalcoholsulfonylamino, polyhaloalkylcarbonylamino, trialkylsilyl, aryldialkylsilyl, triarylsilyl, sulfonic acid and derived salts, phosphonic acid and derived salts, alkoxycarbonylamino, alkylaminocarbonyloxy, dialkylaminocarbonyloxy, alkenyl, polyhaloalkenyl, alkenyloxy, alkynyl, alkynyloxy - Polyhaloalkenyloxygruppe, Polyhaloalkynyl, Polatialoalkynyloxygruppe, Polyfluoroalkanal, Zyanoalkylaminogruppe, Seniikarbazonomet.hyl, Alkoxycarbonylhydrazonomethyl, Alkoxyiniinomethyl, unsubatituted or substituted Aryloxyiminomethyl, hydrazonomethyl, unsubstituted or substituted arylhydrazonomethyl, mono-, di- or poly-saccharide-fused hydroxy, haloalkyl, haloalkenyl, haloalkynyl , Alkoxyalkyl, aryloxy, aralkoxy, arylthio, aralkylthio, alkylthioalkyl, arylthioalkyl, arylsulfinyl, arylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, haloalkenyloxy, haloalkynylox y-, haloalkynyl thio group, Haloalkenylsulfonyl, Polyhaloalkenylsulfonyl, alkoxysulfonyl, aryloxysulfonyl, Porpargyloxygruppe, aroyl, Haloazyl, Polyhaloazyl, Aryloxykarbonyl, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, arylaminosulfonyl, Karboxyalkoxy-, Karboxyalkylthio-, Alkoxykarbonylalkoxy-, Azyloxy-, Haloazyloxy-, Polyhaloazyloxy-, Aroyloxy, alkylsulfonyloxy, alkenylsulfonyloxy, arylsulfonyloxy, haloalkylsulfonyloxy, polyhaloalkylsulfonyloxy, aroylamino, haloazylamino, alkoxycarbonyloxy, arylsulfonylamino, aminocarbonyloxy, cyanato, isocyanato, isothiocyano, cycloalkylamino, trialkylamino, arylamino, aryl (alkyl) aniino, aralkylamino, alkylkoxyalkylphosphine, alkoxyalkylphosphinothioyl, alkylhydroxyphosphinyl, dialkoxyphosphino, hydroxyamino, alkoxyamino, aryloxyamino, aryloxyimino, oxo, thiono, alkylaminoalkoxy, dialkylaiainoalkoxy, alkoxyalkoxy, alkoxyalkenyl, cyanoalkoxy, dialkylsulfonium . -Z, = X, -Z = E ₃ , = XR ₃ , -Z-R _3, -P _v -Y ₂ R _4, -Y ₄ -P-Y ₂ R ₄ Y ₃ R ₅ ^Y 2 ^R 4 Y ₃ R ₅ (Xxxii) (Xxxiii) * 64 wherein: Yg2 » ^Y G ₃ » ^Y 64 '^ 65
Halogen are; ^ 66 or different and R _{1 is} a substituted or unsubstituted, carbocyclic or heterocyclic ring system which is selected from a monocyclic aromatic or nonaromatic ring system, a biocyclic aromatic or non-aromatic ring system, a ~ paly cyclic aromatic or nonaromatic ring system and a bridging ring system which may be saturated or unsaturated, the permissible substituents being the same or different and one or more of the following: hydrogen , Halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthics, polyhaloalkenylthio, thiozyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxy, lmmamidino, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl , Hydroxy, amino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, nitro, cyano, hydroxycarbonyl and derived salts, pormamido, alkyl, alkoxy, polyhaloalkyl, Polyhaloalkoxy group, alkoxycarbonyl, substituted amino group, in which the permissible substituents are identical or different and one or two of the following: propargyl, alkoxyalkyl, alkylthioalkyl, alkyl, alkenyl, haloalkenyl or polyhaloalkenyl; Alkylthio, Polyhaloalkylthiogruppe, alkylsulfinyl, Polyhaloalkylsulfonyl, PoIyhaloalkylsulfinyl, alkylsulfonyl, alkylsulfonylamino, Alkylkarbonylamino-, Polyhaloalkylsulfonylaminogruppe, trialkylsilyl, aryldialkylsilyl, triarylsilyl, SuIfonsäure and salts derived phosphonic acid and derivative salts, Alkoxykarbonylamino-, Alkylaminokarbonyloxy-, Dialkylaminokarbonyloxygruppe, alkenyl, Polyhaloalkenyl, alkenyloxy , Alkynyl, alkynyloxy, polyhaloalkenyl, oxy group, polyhaloalkynyl, polyhaloalkynyloxy group, polyfluoroalkanol, cyanoalkylamino group, semicarbazonomethyl, alkoxycarbonylhydrazonomethyl, alkoxymimiminomethyl, unsubstituted or substituted aryloxyiminomethyl, hydrazonomethyl, unsubstituted or substituted arylhydrazonomethyl, one with a mono-, di- or poly-. saccharide condensed hydroxy, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, aryloxy, aralkoxy, arylthio, aralkylthio, alkylthioalkyl, arylthioalkyl, arylsulfinyl, arylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, haloalkenyloxy, haloalkynyloxy, haloalkynylthio, haloalkenylsulfonyl, polyhaloalkenylsulfonyl, alkoxysulfonyl , Aryloxysulfonyl, propargyl oxy group, aroyl, haloazyl, polyhaloazyl, aryloxycarbonyl, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, arylaminosulfonyl, carboxyalkoxy, carboxyalkylthio, alkoxycarbonylalkoxy, azyloxy, haloazyloxy, polyhaloazyloxy, aroyloxy, alkylsulfonyloxy, alkenylsulfonyloxy, Aroyloxy, alkylsulfonyloxy, alkenylsulfonyloxy, arylsulfonyloxy, haloalkylsulfonyloxy, polyhaloalkylsulfonyloxy, aroylamino, haloazylarnino, alkoxycarbonyl oxy, arylsulfonylamino, aminocarbonyloxy, cyanato, isocyanato, isothiocyano, cycloalkylamino, trialkylammonium, arylaraino, Aryl (alkyl) amino, aralky amino group, alkoxyalkylphosphinyl, alkoxyalkylphosphinothioi ", alkylhydroxyphosphinyl, dialkoxyphosphino, hydroxyamino, alkoxyamino, aryloxyamino, aryloxyimino, oxo, thiono, alkylaminoalkoxy, dialkylaminoalkoxy, alkoxyalkoxy, alkoxyalkenyl, cyanoalkoxy, dialkylsulfonium, ~ Λ J = Λ | "" Λ = Kn) • I -XR ₃ . - P - Y ₂ ^R 4 »- ^Y 4 - ¹ ^" ^Y 2 ^R 4 or Y ₃ R ₅ R _{1 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, the permissible substituents being the same or different and one or more of the following: hydrogen, Halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiozyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, aryldialkylsilylox, triarylsilyloxy, samaramidino, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino , Aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylamimothiocarbonyl, dialkylaminothiocarbonyl, nitro, cyano, hydroxycarbonyl and derivative salts, pormamido group, alkyl, alkoxy group, polyhaloalkyl, polyhaloalkoxy group, alkoxycarbonyl, substituted am inogruppe, in which the permissible substituents are the same or different and one or two of the following: propargyl, alkoxyalkyl, alkylthioalkyl, alkyl, alkenyl, haloalkenyl or polyhaloalkenyl; Alkylthio, polyhaloalkylthio group, alkylsulfinyl, polyhaloalkylsulfinyl, alkylsulfonyl, polyhaloalkylsulfonyl, alkylsulfonylamino, alkylcarbonylamino, polyhaloalkylsulfonylamino, polyhaloalkylcarbonylamino, trialkylsilyl, aryldialkylsilyl, triarylsilyl, sulfonic acid and derived salts, phosphonic acid and derived salts, alkoxycarbonylamino, alkylaminocarbonyloxy, dialkylaminocarbonyloxy, Alkenyloxy group, alkenyl, polyhaloalkenyl, alkynyl, alkynyloxy, polyhaloalkenyloxy group, polyhaloalkynyl, polyhaloalkynyloxy group, polyfluoroalkanol, cyanoalkylamino group, semicarbazonomethyl, alkoxycarbonylhydrazonomethyl, alkoxyimincmethyl, unsubstituted or substituted aryloxyiminomethyl, hydrazonomethyl, unsubstituted or _t- substituted arylhydrazonomethyl, one with a mono-, di- or polysacc .harid condensed hydroxy, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, aryloxy, aralkoxy, arylthio, aralkylthio, alkylthioalkyl, arylthioalkyl, Arylsulfinyl, arylsulfonyl, Haloalkylaulfinyl, haloalkylsulfonyl, Haloalkenyloxy-, Haloalkynyloxy-, Haloalkynylthiogruppe, Haloalkenylsulfonyl, Polyhaloalkenylsulfonyl, Alkoxysulfonyl, aryloxysulphonyl, propargyloxy, aroyl, Haloazyl, Polyhalozyl, Aryloxj'karbonyl, jtninosulfonyl, alkylaminosulfonyl, Dialkji-laminosulfonyl, arylaminosulfonyl, Karboxyalkoxy-, Karboxyalkylthio , Alkoxycarbonyltilkoxy, - azyloxy, haloazyloxy, polyhaloazyloxy, aroyloxy, alkylsulphonyloxy, alkenylsulphonyloxy, arylsulphonyloxy, haloalkylsulphonyloxy, polyhaloalkylsulphonioxy, aroylamino, haloazylamino, alkoxycarbonyloxy, arylaulphonynino, aininocarbonyloxy, cyanato , Isocyanato, isothiocyanato, cylcoalkylamino, trialkylamiaonium, arylamino, aryl (alkyl) amino, aralkylamino, alkoxyalkylphosphinyl, alkoxyalkylphospliinothioyl, alkylhydroxyphosphinyl, dialkylphosphino, hydroxamino, alkoxyamino, aryloxyamino, aryloxyimino, oxo, thiono, alkylaminoalkyloxy , Dialkylaminoalkoxy , Alkoxyalkoxy group, alkoxyalkenyl, cyanoalkoxy group, dialkylsulfonium, -X, = X, -X = R ₃ , = XR ₃ , ϊ ' ₃ , - P - Y ₂ R ₄ , - Y ₄ - P - Y ₉ R 3R5 Y ₂ R ₄ X is a divalent single or double bond, a substituted or unsubatituted heteroatom or substituted carbon atom, or a substituted or unbeaten, branched or straight chain containing two or more carbon atoms or heteroatoms in any combination, the permissible substituents being the same or different and one or more of the following are: hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiozyano, propargyltliio, hydroxyimino, alkoxyimino, trialkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxy, 1-amidamido, alkylsulfamido, Dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino, aminocarbonyl, alkylaminocarbonyl, dialkylarainocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, nitro, cyano, hydroxycarbonyl and derivative salts, formamido, alkyl, alkoxy , Polyhaloalkyl, polyhaloalkoxy group, alkoxycarbonyl, substituted amino group in which the permissible substituents are the same or different and one or two of the following: propargyl, alkoxyalkyl, alkylthioalkyl, alkyl, alkenyl, haloalkenyl or polyhaloalkenyl; Alkylthio, Polyhaloalkylthiogruppe, alkylsulfinyl, Polyhaloalkylsulfinyl, alkylsulfonyl, Polyhaloalkylsulfonyl, alkyl sulfonylamino, Alkylkarbonylaniino-, Polyhaloalkylsulfonylamino-, Polyhaloalkylkarbonylarninogruppe, trialkylsilyl, ^r Arj ldialkylsilyl, Triarj ^r lsilyl sulfonic acid and derivative salts, phosphonic acid and derivative salts, Alkoxykarbonylamino-, oxy Alkylaminokarbonyl , Dialkylamino-nocarbonyloxy, alkenyloxy, alkenyl, polyhaloalkenyl, alkynyl, alkynyloxy, polyhaloalkenyloxy, polyhaloalkynyl, polyhaloalkynyloxy, polyfluoroalkanol, cyanoalkylamino, semicarbazonoethyl, alkoxycarbonylhydrazonomethyl, alkoxyiminomethyl, unsubstituted or substituted aryloxyiminomethyl, hydrazono methyl, unsubstituted or substituted arylhydrazonomethyl, a hydroxy group condensed with a ϊ, Ιοηο-, di- or poly-saccharide, ilaloalkyl, haloalkenyl, haloalkyl, alkoxyalkyl, aryloxy, aralkyoxy, arylthio, aralkylthio, alkylthioalkyl, arylthioalkyl, arylsulfinyl, arylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, Haloalkenyloxy-, Haloalkynyloxy-, Haloalkynylthiogruppe, Haloalkenylsulfonyl, Polyhaloalkenylsulfonyl, alkoxysulfonyl, Aryloxy3Ulfonyl, propargyl oxy, aroyl, Haloazyl, Poljrhaloazyl, Aryloxykarbonyl, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, arylaminosulfonyl, Karbdyalkoxy-, Karboxyalkylthio-, Alkoxykarbonylalkoxy-, Azyloxy-, Haloazyloxy -, polyhaloazyloxy, aroyloxy, alkylsulfonyloxy, alkenyl sulfonyl oxy, arylsulfonyloxy, haloalkylsulfonyloxy, polyhaloalkylsulfonyloxy, aroylamino, haloazylamino, alkoxycarbonyl oxy, arylsulfonylamino, aminocarbonyloxy, cyanato, isocyanato, isothiocyanato, Cycloalkylamino group, Tr ialkylammonium, arylamino, aryl (alkyl) amino, aralkylamino, Alkoxyalkylphosphinyl, Alkoxyalkj'lphosphinothioyl, Alkylhydroxyphosphinyl, Dialkoxyphosphino-, Hydroxj ^r amino, alkoxyamino, Aryloxyamino-, Aryloxyimino-, oxo, thiono, alkylaminoalkoxy, Dialkylarninoalkoxy- Alkoxyalkoxy group, alkoxyalkenyl, cyanoalkoxy group, dialkylsulfonium, -X, = X, -X = R ₃ , = XR ₃ , -XR ₃ , -P- Y ₂ R ₄ , -3 3R5 II ¹ - ^p - ^Y 2 ^R 4 ; and R ^ g is a substituted β or unsubstituted, asymmetric heterocyclic ring system having at least three nitrogen atoms selected from a monocyclic aromatic or nonaromatic ring system, a bicyclic aromatic or non-aromatic ring system, a polycyclic aromatic or nonaromatic ring system, and a bridged ring system saturated or may be unsaturated, wherein the permissible substituents are identical or different and one or more of the following: hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiozyano, propargylthio, hydroxyimino, alkoxyimino, Trialkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxy, ponnamidino, alkylaulamido, dialkylsulfamido, alkoxysulfonyl, dialkylaminothiocarbonyl, polyhaloalkoxysulfonyl, hydroxy, amino, aminocarbonyl, alkylamino! Carbonyl, dialkylaminocarbonyl, aminothiocarbo nyl, alkylaminothiocarbonyl, nitro, cyano, hydroxycarbonyl and derived salts, loramamido, alkyl, alkoxy, polyhaloalkyl, polyhaloalkoxy, alkoxycarbonyl, substituted amino in which the permissible substituents are the same or different and one or two of the following: propargyl, alkoxyalkyl, alkylthioalkyl Alkyl, alkenyl, haloalkenyl or polyhaloalkenyl; Alkylthio, Polyhaloalkylthiogruppe, alkylsulfinyl, Polyhaloalkylsulfinyl, alkylsulfonyl, Polyhaloalkylsulfonyl, alkylsulfonylamino, Alkylkarbonylamino-, Polyhaloalkylsulfonylamino-, Polyhaloalkylkarbonylaminogruppe, trialkylsilyl, aryldialkylsilyl, triarylsilyl sulfonic acid and derivative salts, phosphonic acid and derivative salts, Alkoxykarbonylamino-, Alkylaminokarbonyloxy-, Dialkylaminokarbonyloxygruppe, alkenyl, Polyhaloalkenyl, alkenyloxy group, alkynyl, alkynyloxy, polyhaloalkenyloxy group, polyhaloalkynyl, polyhaloalkynyloxy group, polyfluoroalkanol, cyanoalkylamino group, semicarbazonomethyl, alkoxycarbonylhydrazonomethyl, alkoxyiminomethyl, unsubstituted or substituted aryloxyiminomethyl, hydrazonomethyl, unsubstituted or substituted arylhydrazonomethyl, a hydroxyl group condensed with a mono-, di- or poly-saccharide, Haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, aryloxy, aralkoxy, arylthio, aralkylthio, alkylthioalkyl, arylthioalkyl, Arylsulfinyl, arylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, Haloalkenyloxy-, Haloalkynyloxy-, haloalkynyl thio group, Haloalkenylsulfonyl, Polyhaloalkenylsulfonyl, alkoxysulfonyl, aryloxysulfonyl, propargyloxy, aroyl, Haloazyl, Polyhaloazyl, Aryloxykarbonyl, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, arylaminosulfonyl, Karboxyalkoxy-, Karboxyalkylthio-, Alkoxykarbonylalkoxy , Azyloxy, haloazyloxy, polyhaloazyloxy, aroyloxy, alkylsulfonyloxy, alkenylsulfonyl oxy, arylsulfonyloxy, haloalkylsulfonyloxy, polyhaloalkylsulfonyloxy, aroylamino, haloazylamino, alkoxycarbonyloxy, arylaulphonylamino, aminocarbonyloxy, cyanato, isocyanato, isothiocyanato, cycloalkylamino, trialkylammonium, arylamino, aryl (alkyl) amino, Aralkylamino, alkoxyalkylphosphinyl, alkoxyalkylphosphinothioyl, alkylhydroxyphosphinyl, dialkoxyphosphino, hydroxyamino, alkoxyamino, aryloxyamino, aryloxoimino-s oxo, thiono, alkylaminoalkoxy, dialkylaminoalkoxy, alkoxyalkoxy-cyanoalkoxy, alkoxyalkenyl, dialkylsulfonium, -X, = X, -X = R ₃ , - XR ₃ ,
-X - R ₃ , - P - Y ₂ R ₄ , --Y ₄ - P - Y ₂ R ₄ Y ₃ R ₅ Y ₃ R ₅ Y ₃ R ₅ wherein': R 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 bridging ring system which may be saturated or unsaturated, wherein the permissible subatituents are the same or different and one or more of the following: hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiozyano, propargylthio, hydroxyimino, alkoxyimino, trialkylailyloxy, aryldialkylsilyloxy, triarylsilyloxy , Formamidino, alkylsulfamido, dialkylsulfamido, hydroxy, alkoxysulfonyl, dialkylaminocarbonyl, alkoxysulfonyl, polyhaloalkoxysulfonyl, amino, aminocarbonyl, alkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminothioka ribyl, nitro, cyano, hydroxycarbonyl and derived salts, orthoamido, alkyl, alkoxy, polyhaloalkyl, polyhaloalkoxy, alkoxycarbonyl, substituted amino in which the permissible substituents are the same or different and one or two of the following are propargyl, alkoxyalkyl, alkylthioalkyl, alkyl, alkenyl, haloalkenyl or Polyhaloalkenyl5 alkylthio, Polyhaloalkylthiogruppe, Alkyleulfinyl, PoIyhaloalkylsulfinyl, alkylsulfonyl, Polyhaloalkylsulfonyl, alkylsulfonylamino, Alkylkarbonylamino-, Polyhaloalkylsulfonylamino-, Polyhaloalkylkarbonylaminogruppe _s Erialkylsilyl, aryldialkylsilyl, Iriarylsilyl sulfonic acid and derivative salts, phosphonic acid and derivative salts, Alkoxykarbonyl amino-, Alkylaminokarbonyl oxy, dialkylaminocarbonyloxy, alkenyloxy, alkenyl, polyhaloalkenyl, alkkynyl, alkynyloxy, polyhaloalkenyloxy, polyhaloalkynyl, polyhaloalkynyloxy, polyfluoroalkyl kanol, Zyanoalkylaminogruppe, Semikarbazononiethyl, AIkoxykarbonylhydrazonomethyl, alkoxyimlnomethyl, unsubstituted or substituted aryloxyiminomethyl, hydrazonomethyl, unsubstituted or substituted Arylhydrazonomethyl, a condensed with a mono-, di- or polysaccharide hydroxy, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, aryloxy, arylkoxy, arylthio -, aralkylthio, alkylthioalkyl, arylthioalkyl, arylsulfinyl, arylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, Haloalkenyloxy-, Haloakynyloxy-, Haloalkynylthiogruppe, Haloalkenylsulfonyl, Polyhaloalkenylsulfonyl, alkoxysulfonyl, aryloxysulphonyl, propargyloxy, aroyl, Haloazyl, Polyhaloazyl, Aryloxykarbonyl, aminosulfonyl, alkylaminosulfonyl, arylaminosulfonyl, dialkylaminosulfonyl, Carboxyalkoxy, carboxyalkylthio, alkoxycarbonylalkoxy, azyloxy, haloazyloxy, polyhaloalkylsulfonyloxy, polyhaloacyloxy, aroyloxy, alkylsulfonyloxy, alkenylsulfonyloxy, arylsulfonyloxy, haloalkylsulfonyloxy , Aroylamino, haloazylamino, alkoxycarbonyloxy, arylsulfonylamino, aminocarbonyloxy, cyanato, isocyanato, isothiocyanato, cycloalkylamino, trialkylammonium, arylamino, aryl (alkyl) amino, aralkylamino, alkoxyalkylphosphinyl, alkoxyalkylphosphinothioyl, alkylhydroxyphosphinyl, dialkoxyphosphino , Hydroxyamino, alkoxyamino, aryloxyamino, aryloxyimino, oxo, ehiono, alkylaminoalkoxy, dialkylaminoalkoxy, alkoxyalkoxy, alkoxyalkenyl, cyanoalkoxy, dialkylsulfonium, -X, = X, -X = R-3, -X-R-, ₃ R ₅ ^Y 2 ^R 4 ; or ^Y 3 ^R 5 Y ₃ R ₅ R, a substituted heteroatom or a substituted carbon atom: or a substituted or unsubstituted, branched or straight chain having two or more carbon atoms in any combination in which the permissible substituents are the same or different and one or more of the following: hydrogen, Halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiozyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxy, pormamidino, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxyl Carbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, nitro, cyano, hydroxycarbonyl and derived salts, formamido, alkyl, alkoxy, polyhaloalkyl, polyhaloalkoxy, alkoxycarbonyl, substituted amino, i.a. n the permissible substituents are identical or different and one or two of the following: propargyl, alkoxy alkyl, alkylthioalkyl, alkyl, alkenyl, haloalkenyl or polyhaloalkenyl; Alkylthio, polyhaloalkylthio group, alkylhalphinyl, polyhaloalkylsulfinyl, alkylsulfonyl, polyhaloalkylsulfonyl, alkylsulfonylamino, alkylcarbonylamino, polyhaloalkylsulfonylamino, polyhaloalkylcarbonylamino, trialkylsilyl, aryldialkylsilyl, triarylsilyl, sulfonic acid and derived salts, phosphonic acid and derived salts, alkoxycarbonylamino, alkylaminocarbonyloxy Alkenyl, polyhaloalkenyl, alkenyloxy group, alkynyl, alkynyloxy, polyhaloalkenyloxy group, polyhaloalkynyl, polyhaloalkynyloxy group, polyfluoroalkanol, cyanoalkylamino group, semicarbazonomethyl, alkoxycarbonylhydrazonomethyl, alkoxyiminomethyl, unsubstituted or substituted aryloxyiminomethyl, hydrazonomethyl, unsubstituted or substituted arylhydrazonomethyl, one with a mono -, di- or polysaccharide condensed hydroxy, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, aryloxy, aralkoxy, arylthio, aralkylthio, alkylthioalkyl, Ar ylthioalkyl, arylsulfinyl, arylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, Haloalkenyloxy-, Haloalkynyloxy-, Halalkynylthiogruppe, Haloalkenylsulfonyl, Polyhaloalkenylsulfonyl, alkoxysulfonyl, aryloxysulfonyl, propargyloxy, aroyl, Haloazyl, Polyhaloazyl, Aryloxykarbonyl, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, arylaminosulfonyl, Karboxyalkoxy-, Karboxyalkylthio-, Alkoxycarbonylalkoxy, Azyloxy, Haloazyloxy, Polyhaloazyloxy, Arylsulfonyloxy, Aroyloxy, Alkylaulfonyloxy, Alkenyl s.ulfonyl oxy, haloalkylsulfonyl oxy, polyhaloalkylsulfonyloxy, aroylamino, Haloazylamino, Alkoxykarbonyloxy-, aryl sulfonyl amino- , Amino carbonyl oxy, cyanato, isocyanato, isothiocyanato, cycloalkylamino, trialkylammonium, arylamino, aryl (alkyl) amino, arylalkylamino, alkoxyalkylphosphinyl, alkoxyalkylphosphinothioyl, alkylhydroxyphosphinyl, dialkoxyphosphino, hydroxyamino, alkoxyamino, aryloxyamino, Aryloxyimino, oxo, thiono, alkylaminoalkoxy, dial kylaminoalkoxy, alkoxyalkoxy, alkoxyalkenyl, cyanoalkoxy, dialkylsulfonium, II ¹ -XR ₃ , - P- Y ₂ R ₄ , -Y ₄ - P- Y ₃ R ₅ Y and Y are independently oxygen or sulfur; Y ₂ and Y are independently oxygen, sulfur, an amino group or a divalent bond, and R ₄ and R _{5 are} independently hydrogen or substituted or unsubstituted alkyl, polyhaloalkyl, phenyl or benzyl, the permissible substituents being the same or different and one or more of the following: hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, Polyhaloalkenylthio, thiozyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxy, imomamidino, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl , Dialkylaminothiocarbonyl, nitro, cyano group, hydroxy carbonyl and derived salts, formamido group, alkyl, alkoxy group, polyhaloalkyl, polyhaloalkoxy group, alkoxy carbonyl, substituted amino group in which the permissible substituents are the same or different and one or two of the following: propargyl, alkoxyalkyl, alkylthioalkyl, Alkyl, alkenyl, haloalkenyl or polyhaloalkenyl; Alkylthio, Polyhaloalkylthiogruppe, alkylsulfinyl, Polyhaloalkylsulfinyl, alkylsulfonyl, Poiyhaloalkylsulfonyl, alkylsulfonylamino, Alkylkarbonylamino-, PolyhaloalkylBulfonylamino-, Polyhaloalkylkarbonylaminogruppe, trialkylsilyl, aryldialkylsilyl, triarylsilyl sulfonic acid and derivative salts, phosphonic acid and derivative salts, Alkoxykarbonylamino-, Alkylaminokarbonyloxy-, Dialkylaminokarbonyloxygruppe, alkenyl, Polyhaloalkenyl, alkenyloxy group, alkynyl, alkynyloxy group, polyhaloalkenyloxy group, polyhaloalkynyl, polyhaloalkynyloxy group, polyfluoroalkanol, cyanoalkylamino, semicarbazonomethyl, alkoxycarbonylhydrazonomethyl, alkoxyiminomethyl, unsubstituted or substituted aryloxyiminomethyl, hydrazonomethyl, unsubstituted or substituted arylhydrazonomethyl, a hydroxy, fused with a mono-, di- or polysaccharide, haloalkyl , Haloalkenyl, haloalkynyl, alkoxyalkyl , aryloxy, aralkoxy, arylthio, arylalkylthio, alkylthioalkyl, arylthio alkyl, arylsulfinyl, arylsulfonyl, haloalkyl sulf inyl, haloalkylsulfonyl, Halοalkenyl oxy, haloalkynyl oxy, Haloalkynylthiogruppe, Haloalkenylsulfonyl, Polyhaloalkenylsulfonyl, alkoxysulfonyl, aryloxysulfonyl, propargyloxy, aroyl, Haloazyl, Polyhaloazyl, Aryloxykarbonyl, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, arylaminosulfonyl, Karboxyalkoxy- , Carboxyalkylthio, alkoxycarbonylalkoxy, azyloxy, haloazyloxy, polyhaloacyloxy, aroyloxy, alkylsulfonyloxy, alkenylsulfonyloxy, arylsulfonyloxy, haloalkylsulfonyloxy, polyhaloalkylsulfonyloxy, aroylamino, haloazylamino, alkoxycarbonyloxy, arylsulfonylamino, aminocarbonyloxy, cyanato , Isocyanato, Isothiozyano, Cycloalkylamino, Arylamino, Trialkylammonium, Aryl (alkyl) -amino, Aralkylamino, Alkoxyalkylphosphinyl, Alkoxyalkylphosphinothioyl, Alkylhydroxyphosphinyl, Dialkylphosphino, Hydroxyamino, Alkoxyamino ,. Aryloxyamino, aryloxyimino, oxo, thiono, alkylaminoalkoxy, dialkylaminoalkoxy, alkoxyalkoxy, alkoxyalkenyl, cyanoalkoxy, dialkylsulfonium, -Λ, -A, -Λ ⁼ Ro, ~ Λ-R * 3, ^Y 3 ^R 5 Ϊ1 -XR ₃ , - P- Y ₂ R ₄ , -Y ₄ - P- Y ₂ R ₄ ^Υ 2 ^Η 4 · ^Y 3 ^R 5 wherein X, R ₃ , R ₄ , R _c »Y y» Y ₂ »Y ₃
are defined. ^{new in} The method of claim 1, characterized in that the compound is applied to the plant surface in an amount sufficient to reduce the loss of moisture from the plant surface without causing substantial inhibition of the photosynthetic light responses of the plant. A method according to claim 1, characterized in that the compound is applied to the plant surface under conditions where there is substantially no water stress for the plant. A method according to claim 1, characterized in that the compound is applied to the plant surface at a time prior to the reproductive growth phase of the plant. 45. The method according to item 1, characterized in that the compound is applied to the plant surface at a time before a considerable moisture loss of the soil. 46. The method according to item 1, characterized in that the compound is applied to the plant surface at a time during the reproductive growth phase of the plant. 47 «Method according to item 1, characterized in that the compound on the plant surface in a concentration of about 0.045
is brought · - 45.359 kg of the compound per 4047 m 48. The method according to claim 1, characterized in that the compound on the plant surface in a concentration of about 0.113 - 6.8 kg of the compound each 2
4047 m is applied. 49 «The method of claim 1, characterized in that the plant is an agricultural or horticultural garden, ornamental or meadow grass. 50. The method according to claim 1, characterized in that the plant is selected from corn, cotton, sweet potatoes, white potatoes, lucerne, wheat, rye, highland rice, barley, oats, tobacco, sorghum, dried beans, soybeans, sugar beets, sunflowers, tomatoes , Canola, deciduous fruits, citrus fruits, tea, coffee, olives, pineapple, cocoa, bananas, sugar cane, oil palm, perennial border plants, wood shrubs, meadow grasses, ornamentals, evergreens, trees and flowers. 51. The method according to claim 1, characterized in that the plant is a transplanted plant · 52. The method according to claim 51, characterized in that the reacted plant material is selected from tobacco, tomatoes, egg plants, cucumbers, lettuce, strawberries, perennial plant plants, wood shrubs and tree seedlings. A method for increasing crop yields, characterized in that an effective amount sufficient to increase crop yield without substantially affecting the photosynthetic electron transport chain of the plant is applied to the crop to a compound having the formula: - X - wherein: R - is a substituted or unsubstituted, carbocyclic or heterocyclic ring system selected from a monocyclic aromatic or nonaromatic ring yyme, a bicyclic aromatic or nonaromatic ring radical, a polycyclic aromatic or nonaromatic ring system, and a bridging ring system which may be saturated or unsaturated in which the permissible substituents are identical or different and one or more of the following are: hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiozyano, propargylthio, hydroximino, alkoxyimino, trialkylsilyloxy, aryldialkylailyloxy, triarylsilyloxy , ammmamidino, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, nitro , Cyano group, hydroxy carbonyl and derivative salts, pormamido group, alkyl, alkoxy group, polyhaloalkyl, polyhaloalkoxy group, alkoxy carbonyl, substituted amino group in which the permissible sub-substituents are the same or different and one or two of the following: propargyl, alkoxyalkyl, alkylthioalkyl, alkyl, alkenyl, haloalkenyl or polyhaloalkenyl; Alkylthio, Polyhaloalkylthiogruppe, alkylsulfinyl, Polyhaloalkylsulfinyl, alkylsulfonyl, Polyhaloalkylsulfonyl, Alkylaulfonylamino-, Alkylkarbonylamino-, Polyhaloalkylsulfonylamino-, Polyhaloalkylkarbonylaminogruppe, trialkylsilyl, aryl dialkylsilyl, triarylsilyl, sulfonic acid and derivative salts, and salts derived Phosphonaäure, Alkoxykarbonylamino-, Alkylaminokarbonyloxy-, Dialkylaminokarbonyloxygruppe, alkenyl , Polyhaloalkenyl, alkenyloxy group, alkynyl, alkynyloxy, polyhaloalkenyloxy group, polyhaloalkynyl, polyhaloalkynyloxy group, polyfluoroalkanol, cyanoalkylamino group, semicarbazonomethyl, alkoxycarbonylhydrazonomethyl, alkoxyiminomethyl, unsubstituted or substituted aryloxyiminomethyl, hydrazonomethyl, unsubstituted or substituted arylhydroζonomethyl, a mono-, di- or polysaccharide-fused hydroxy group , Haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, aryloxy, aralkoxy, arylthio, aralkylthio, alkylthioalkyl, arylthioalky l, arylsulfinyl, arylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, Haloalkenyloxy-, Haloalkynyloxy-, Haloalkynylthiogruppe, Haloalkenylsulfonyl, Polyhaloalkenylsulfonyl, alkoxysulfonyl, Aryloxyaulfonyl, propargyloxy, aroyl, Haloazyl, Polyhaloazyl, Aryloxykarbonyl, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, arylaminosulfonyl, Karboxyalkoxy-, Karbpxyalkylthio-, Alkoxycarbonyloxy, azyloxy, haloazyloxy, polyhaloalkylsulphonyloxy, polyhaloacyloxy, aroyloxy, alkylsulphonyloxy, alkenylsulphonyloxy, arylsulphonyloxy, haloalkylsulphonyloxy, aroylamino, haloazylamino, alkoxycarbonyloxy, arylsulphonylamino, aminocarbonyloxy, cyanato, isocyanato, , Isothiocyanato, cycloalkylamino, trialkylammonium, arylamino, aryl (alkyl) amino, aralkylamino, alkoxyalkylphosphinyl, alkoxyalkylphosphinothioyl, alkylhydroxyphosphinyl, dialkylaminoalkoxy, di- alkoxyphoaphino, hydroxyamino, alkoxyamino, aryloxyamino, aryloxyimino, oxo, thiono, alkylaminoalkoxy, alkoxyalkoxy, alkoxyalkenyl, cyanoalkoxy, dialkylsulfonium, -X, = X ₉ -X = R ₃ , = XR ₃ , -X-R ₃ , -P-Y ₂ R ₄ , -Y ₄ -P -Y ₂ R ₄ Y ₃ R ₅ Y ₃ R ₅ or ^Y 3 ^R 5 R _{1 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 wherein the permissible substituents are the same or different and one or more of the following are hydrogen, Halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiozyano, propargylthio, hydroxyimino, alkoxyiqiino, trialkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxy, sulfamido, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino, Aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, nitro, cyano, hydroxycarbonyl, and derived salts, amoramido, alkyl, alkoxy ;, oxy, oxyalkylene, alkoxycarbonyl, substituted the amino group in which the zuläasiiuGn substituents are the same or different and one or Kv; ci of the following are: propargyl, Alkoxyalk'yl, Alkylthiofükyl, alkyl, alkenyl, IIaloal3: enyl or Polyhaloalkeuyl; Älktylthio-, Polyhaloalkyltliio-, Alkylsulfonylamino -; ..; group, .Al3;: ylaul: i: 'iiiyl, Polyhaloolkylsulfinyl, Alkylsul'fonyl, Polyhaloalkyloulfonyl, Alkylkarbonylcnviino-, PolyliRloalkj / lsulfonylaraiuo, Polyhsloalkylksrbonylaminogruppe,! Iricilkylsilyl, Aryldialkylsilyl, l'ariarylsilyl , sulfonic acid and deduced Salae, phosphonic acid and deduced üalze, Alkoxykarbonylamino-, Alkylaminokarbonyloxy-, Dialkylaminokorbonyloxygruppo, alkenyl, Polylialoalkenyl, alkenyloxy, alkynyl, alkynyloxy, Polyhaloalkenyloxygruppe, Polylialoalkynyl, Polyhaloalkynyloxygruppe, Polyfluoroalkanol, Zyanoalkylaminogruppe, Semikarbazonornethyl, Alkoxykarbonylhydrazonoraethyl, Alkoxyiminornethyl, unsubstituted or substituted Aryloxyiminomethyl , Hydrazonomethyl, unsubstituted or substituted arylhydrazonomethyl, a hydroxy group condensed with a mono-, di- or polysaccharide, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, aryloxy, arakoxy, arylthio, aralkylthio group, Alkylthioalkyl, arylthioalkyl, Ar _v lsulfinyl, arylsulfonyl, haloalkylsulfinyl, Ilaloalkylsulfonyl, Haloalkenyloxy-, Haloalkynyloxy-, Haloalkynylthiogruppe, Iialoalkeny! Sulfonyl, Polyhaloalkenylsulfonyl, Alkoxysulfonyl, aryloxysulphonyl, propargyloxy, aroyl, Haloazyl, Polyhaloazyl, aryloxy! Carbonyl, amino Ulf onyl, Alkylaminosiilf onyl , Dia-lynylaminosulfonyl, arylaminosulfonyl, carboxy-alkoxy, liarboxyalkylthio », Alkoxycarbonylalkoxy, azyloxy, haloazyloxy, polyhaloazyloxy, aroyloxy, alkylsulphonyloxy, alkenylsulphonyloxy, arylsulphonyloxy, haloalkylsulphonyloxy, polyhaloalkylsulphonyloxy, aroylamino, haloazylamino, alkoxycarbonyloxy, arylsulphonylamino, tonino-carbonyloxy, cyanato , Isocyanato, isothiocyanato, cycloalkylamino, trialkylammonium, arylamino, aryl (alkyl) amino, aralkylamino, alkoxyalkylphosphinyl, alkoxyalkylphosphinothioyl, alkylhydroxyphosphinyl, dialkoxyphosphino, hydroxyamino, alkoxyamino, aryloxyamino, aryloxyimino, oxo, thiono, Alkylaminoalkoxy, dialkylaminoalkoxy, alkoxyalkoxy, alkoxyalkenyl, cyanoalkoxy, dialkylsulfonium, -X, = X, -X = R _v = XR ₃ , -XR ₃ , -P- P
\ ^Y 2 ^R 4 ^Y 3 ^R 5 X is a divalent single bond or double bond, a substituted or unsubstituted heteroatom or a substituted carbon atom or a substituted or unsubstituted, branched or straight chain which. containing two or more carbon atoms or heteroatoms in any combination wherein the permissible substituents are the same or different and one or more of the following: hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiozyano, propargylthio, hydroxyimino -, Alkoxyimino-, Trlarylsilyloxy-, Aryldialkylsilyloxy-, Triarylsilyloxy-, 3'-ammamidino-, Alkylsulfamido, Dialkylsulfamido, Alkoxysulfonyl, Polyhaloalkoxysulfonyl, hydroxy, amino group, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, Alkylaminothiokarbonyl, Dialkylaminothiokarbonyl, Witro-, cyano group , Hydroxy carbonyl and derivative salts, pormamido group, alkyl, alkoxy group, polyhaloalkyl, polyhaloalkoxy group, alkoxy carbonyl, substituted amino group in which the permissible substituents are the same or different and one or two of the following: propargyl, alkoxyalkyl, alkylthio thioalk yl, alkyl, alkenyl, haloalkenyl or polyhaloalkenyl; Alkylthio, polyhaloalkylthio, alkylsulfonylamino, alkylsulfinyl, polyhaloalkylsulfinyl, alkylsulfonyl, polyhaloalkylsulfonyl, alkylcarbonylamino, polyhaloalkylsulfonylamino, polyalkylcarbonylamino, trialkylsilyl, aryldialkylsilyl, triarylsilyl, sulfonic and derived salts, phosphonic acid, and derived salts. Alkoxykarbonylamino-, Alkylaminokarbonyloxy-, Dxalkylaminokarbonyloxygruppe, alkenyl, Polyhaloalkenyl, alkenyloxy, alkynyloxy, alkynyl, Polyhaloalkenyloxygruppe, Polyhaloalkynyl, Polyhaloalkynyloxygruppe, Polyfluoroalkanol, Zyanoalkylaminogruppe, Semikarbazonomethyl, Alkoxykarbonylhydrazonomethyl, alkoxyiminomethyl, unsubstituted or substituted Aryloxyiminomethyl, hydrazonomethyl, unsubstituted or substituted Arylhydraζonomethyl, one with a Mono, di- or polysaccharide condensed hydroxy, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, aryloxy, aralkoxy, arylthio, aralkylthio, alkylthioalkyl, arylthioalkyl, arylsulfinyl, arylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, haloalkenyloxy, haloalkynyloxy, haloalkynylthio, haloalkenesulfonyl, polyhaloalkenylsulfonyl, alkoxysulfonyl , Aryloxysulfonyl, propargyloxy, aroyl, haloazyl, polyhaloazyl, aryloxycarbonyl, aminoaliphonyl, alkylaminosulfonyl, dialkylaminosulfonyl, arylaminosulfonyl, carboxyalkoxy, carboxyalkylthio, alkoxycarbonylalkoxy, azyloxy, haloazyloxy, polyhaloazyloxy, aroyloxy, alkylsulfonyloxy, alkenylsulfonyloxy, arylsulfonyloxy Alkenylsulfonyloxy, haloalkylsulfonyloxy, polyhaloalkylsulfonyloxy, aroylamino, haloazylamino, alkoxycarbonyloxy, arylsulfonylamino, aminocarbonyloxy, cyanato, isocyanato, isothiocyano, cycloalkylamino, trialkylammonium, arylamino, aralkylamino, aryl (alkyl) amino group , Alkoxyalkylphosp hinyl, alkoxyalkylphosphinothioyl, alkylhydroxyphosphinyl, dialkoxyphosphino, hydroxyamino, alkoxyamino, aryloxyamino, aryloxyimino, oxo, thiono, alkylaminoalkoxy, dialkylaminoalkoxy, ATkoxyalkoxy, alkoxyalkenyl, cyanoalkoxy, dialkylsulfonium, -X, = X, -X = R ₃ , = XR ₃ , f -X - R ₃ , - P- Y ₂ R ₄ , -Y ₄ - Ϊ - Y ₂ R ₄ ^Y 3 ^R 5 Y ₃ R ₅ - ^ and Y ₃ R ₅ Rg is a substituted or unsubstituted, heterocyclic-3-ring system having at least one nitrogen atom 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 bridging ring moiety in which the permissible substituents are identical or different and one or more of the following: hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiozyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy , Aryldialkylsilyloxy, triarylsilyloxy, samaramidino, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino, amino carbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialky aminothiocarbonyl, nitro, cyano, hydroxycarbonyl and derived salts, amoramido, alkyl, alkoxy, polyhaloalkyl, polyhaloalkoxy, alkoxycarbonyl, substituted amino in which the permissible substituents are the same or different and one or two of the following: propargyl, alkoxyalkyl, alkylthioalkyl, Alkyl, alkenyl, haloalkenyl or polyhaloalkenyl; Alkylthio, polyhaloalkylthio group, alkylsulfinyl, polyhaloalkylsulfinyl, alkylsulfonyl, poly- haloalkylsulfonyl alkylsulfonylamino, Alkylkarbonylamlno-, Polyhaloalkylsulfonylamino-, Polyhaloalkylkarbonylaminogruppe, trialkylsilyl, aryldialkylsilyl, triarylsilyl sulfonic acid and salts derived, acid, phosphonic acid and derivative salts, Alkoxykarbonylamino-, Alkylaminokarbonyloxy-, Dialkylaminokarbonyloxygruppe, alkenyl, Polyhaloalkenyl, alkenyloxy, alkynyl, alkynyloxy, Polyhaloalkenyloxygruppe, Polyhaloalkynyl, polyhaloalkynyloxy group, polyfluoroalkanol, cyanoalkylamino group, semicarbozonomethyl, alkoxycarbonylhydrazonomethyl, alkoxyiminomethyl, unsubstituted or substituted aryloxyiminomethyl, hydrazonomethyl, unsubstituted or substituted arylhydrazonomethyl, a mono-, di- or polysaccharide-fused hydroxy group, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, aryloxy-, Aralkoxy, arylthio, aralkylthio, alkylthioalkyl, arylthioalkyl, arylsulfinyl, arylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, haloalkenyloxy, haloalkyny loxy-, Haloalkynylthiogruppe, haloalkenyl sulfonyl, Polyhaloalkenylsulfonyl, alkoxysulfonyl, aryloxysulfonyl, propargyloxy, aroyl, Haloazyl, PoIyhaloazyl, Aryloxykarbonyl, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, arylaminosulfonyl, Karboxyalkoxy-, Karboxyalkylthio-, Alkoxykarbonylalkoxy-, Azyloxy-, Haloazyloxy-, Polyhaloazyloxy-, Aroyloxy, alkylsulfonyloxy, alkenylsulfonyloxy, arylsulfonyloxy, haloalkylsulfonyl oxy, polyhaloalkylsulfonyloxy, aroylamino, haloacylamino, alkoxycarbonyloxy, arylsulfonylamino, aminocarbonyloxy, cyanato, isocyanato, isothiocyano, cycloalkylamino, trialkylammonium, arylamino, Aryl- (alkyl) amino, aralkylamino, alkoxyalkylphosphinyl, alkoxyalkylphosphino-thioyl, alkylhydroxyphosphinyl, dialkylaminoalkoxy, dialkoxyphosphino, hydroxyamino, alkoxyamino, aryloxyamino, aryloxyimino, oxo, thiono, alkylaminoalkoxy, alkoxyalkoxy, alkoxyalkenyl, cyanoalkoxy, dialkylsulfonium . -Λ, - A, -A - J n) Tj VP * X ₂ K _4, worxn: R 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 bridging ring system which may be saturated or unsaturated, in which the permissible substituents are identical or different and one or more of the following: hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiozyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxy, Formamido, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino, aminocarbonyl, alkylaminocarbonyl, dialkylarninocarbonyl, aminothiocarbonyl, alkylaminotliocarbonyl, dialkylaminothiocarbonyl, nitro, cyano, hydroxycarbonyl and derived salts, organomidido, alkyl, alkoxy, polyhaloalkyl , Polyhaloalkoxy group, alkoxycarbonyl, substituted amino group in which the permissible substituents are the same or different and one or two of the following: propargyl, alkoxyalkyl, alkylthioalkyl, alkyl, alkenyl, haloalkenyl or polyhaloalkenyl; Alkylthio, Plyhaloalkylthiogruppe, alkylsulfinyl, Polyhaloalkylsulfinyl, alkylsulfonyl, Polyhaloalkylsulfonyl, alkylsulfonylamino, Alkylkarbonylamino-, Polyhaloalkylsulfonylamino-, Polyhaloalkylkarbonylaminogruppe, trialkylsilyl, aryldialkylsilyl, triarylsilyl sulfonic acid and derivative salts, phosphonic acid and derivative salts, Alkoxykarbonyl amino-, Alkylaininokarbonyloxy-, Dialkylaminokarbonyloxygruppe, alkenyl , Polyhaloalkenyl, alkenyloxy group, alkynyl, alkynyloxy, polyhaloalkenyloxy group, polyhaloalkynyl, polyhaloalkynyloxy group, polyfluoroalkanol, cyanoalkylamino group, semicarbazonomethyl, alkoxycarbonylhydrazonomethyl, alkoxyiminomethyl, unsubstituted or substituted aryloxyiminomettiyl, hydrazonomethyl, unsubstituted or substituted arylhydrazonomethyl, one with a mono-, di- or polysaccharide fused hydroxy, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, aryloxy, aralkoxy, arylthio, aralkylthio, alkylthioalkyl, arylthio lkyl, arylsulfinyl, arylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, Haloalkenyloxy-, Haloalkynyloxy-, Haloalkynylthiogruppe, Haloalkenylaulfonyl, Polyhaloalkenylsulfonyl, alkoxysulfonyl, Aryloxy3ulfonyl, propargyloxy, aroyl, HaIoazyl, Polyhaloazyl, Aryloxykarbonyl, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, arylaminosulfonyl, Karboxyalkoxy-, Karboxyalkylthio-, Alkoxycarbonylalkoxy, azyloxy, haloazyloxy, polyhaloazyloxy, aroyloxy, alkylsulphonyloxy, alkenylsulphonyloxy, arylsulphonyloxy, alkenylsulphonyloxy, haloalkylsulphonyloxy, polyhaloalkylsulphonyl oxy, aroylamino, haloazylamino, alkoxycarbonyloxy, arylsulphonylamino, aminocarbonyloxy, Cyanato, isocyanato, isothiocyanato, cycloalkylamino, trialkylammonium, arylamino, aryl (alkyl) amino, aralkylmethyl, alkoxyalkylphosphinyl, alkoxyalkylphosphinothioyl, alkylhydroxyphosphinyl, dialkoxyphosphino, hydroxyamino, alkoxyamino, aryloxyamino, aryloxyimino, oxo, thiono , Alkylaminoalkoxy, Dialkylaminoalkoxy, alkoxyalkoxy, alkoxyalkenyl, cyanoalkoxy, dialkylsulfonium, or Y ₃ R ₅ R-. a substituted heteroatom or a 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 the same or different and one or more of the following: hydrogen, Halogen, alkylcarbonyl, alkylcarbonylalkyl, kalkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiozyano, propagylthio, hydroxyimino, alkoxyimino-T trialkylsilyloxy, aryldialkylsilyloxy, triaryl-3-ylyloxy, formamidino, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, Amino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, nitro, cyano, hydroxycarbonyl and derivative salts, formamido, alkyl, alkoxy, polyhaloalkyl, polyhaloalkoxy, alkoxycarbonyl, substituted Amino group in which the permissible substituents are the same or different and one or two of the following: propargyl, alkoxyalkyl, alkylthioalkyl, alkyl, alkenyl, haloalkenyl or polyhaloalkenyl; Alkylthio, polyhaloalkylthio group, alkylsulfinyl, polyhaloalkylsulfonyl, alkylsulfonyl, polyhaloalkylsulfinyl, alkylsulfonylamino, alkylcarbonylamino, polyhaloalkylsulfonylamino, polyhaloalkylcarbonylamino, trialkylsilyl, aryldialkylsilyl, triarylsilyl, sulfonic acid and derived salts, phosphonic acid and derived salts, alkoxycarbonylamino, alkylaminocarbonyloxy, dialkylaminocarbonyloxy group, alkenyl, Polyhaloalkenyl, alkenyloxy, alkynyl, alkynyloxy, Polyhaloalkenyloxygruppe, Polyhaloalkynyl, Polyhaloalkynyloxygruppe, Polyfluoroalkanol, Zyanoalkylaminogruppe, Semikarbazonomethyl, alkoxy _r karbonylhydrazonomethyl, alkoxyiminomethyl, unsubstituted or substituted Aryloxyiminomethyl, hydrazonomethyl, unsubstituted or substituted Arylhydrazonomethyl, one with a mono-, di- or Plysaccharide condensed hydroxy group, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, aryloxy, aralkoxy, arylthio, aralkylthio, alkylthioalkyl, arylthioal kyl, arylsulfinyl, arylsulfonyl, haloalkylsulfinyl, Haloalkylsulfonylfonyl, Haloalkenyloxy-, Halpalkynyloxy-, Haloalkynylthiogruppe, Haloalkenylsulfonyl, Polyhaloalkenylsulfonyl, alkoxysulfonyl, aryloxysulfonyl, propargyloxy, aroyl, Haloazyl, Polyhaloazyl, Aryloxykarbonyl, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, arylaminosulfonyl, Karboxyalkoxy-, Karboxyalkylthio-, Alkoxycarbonylalkoxy, azyloxy, haloazyloxy, polyhaloazyloxy, aroyloxy, alkylsulfonyloxy, alkenylsulfonyloxy, arylsulfonyloxy, haloalkylsulfonyloxy, phallyloalkylsulfonyloxy, aroylamino, haloazylamino, alkoxycarbonyloxy, arylsulfonylamino, aminocarbonyloxy, cyanato, Isocyanato, isothiocyanato, cycloalkylamino, trialkylammonium, arylamino, aryl (alkyl) amino, aralkylamino, alkoxyalkylphosphinyl, alkoxyalkylphosphinothioyl, alkylhydroxyphosphinyl, dialkoxyphosphino, Hydroxyamines, alkoxyamino, aryloxyamino, aryloxyimino, ΟχO, thiono, alkylaminoalkoxy, dialkylaminoalkoxy, alkoxyalkoxy, alkoxyalkenyl, cyanoalkoxy, dialkylsulfonium, "" Λ, ⁼ X, "Λ ->, - A-Ko, Il y - P- Y ₂ ^R 4 '~ ^Υ 4 ~ \ ~ ^Y 3 ^R 5 Y. and Y. are independently oxygen or sulfur; Y ₂ and Y-> independently of one another are oxygen, sulfur, an amino group or a divalent bond and R. and R ₁ - are independently hydrogen or substituted or unsubstituted alkyl, polyhaloalkyl, phenyl or benzyl, wherein the permissible substituents and one or more of the following are the same or different: hydrogen, halogen, Alkylkarbonyl, Alkylkarbonylalkyl, Alkoxykarbonylalkyl, Alkoxykarbonylalkylthio-, Polyhaloalkenylthio, thiozyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, aryldialkylsilyloxy, triarylailyloxy, pormamidino, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl , Dialkylaminothiocarbonyl, nitro, cyano, hydroxycarbonyl and derivative salts, pormamido group, alkyl, alkoxy group, polyhaloalkyl, polyhaloalkoxy group, alkoxycarbonyl, substituted amino group in which the permissible substituents are the same or different and one or two of the following which are: propargyl, alkoxyalkyl, alkylthioalkyl, alkyl, alkenyl, haloalkenyl or polyhaloalkenyl; Alkylthio, polyhaloalkylthio group, alkylsulfinyl, polyhaloalkylsulfinyl, alkylsulfonyl, polyhaloalkylsulfonyl, alkylsulfonylamino, alkylcarbonylamino, polyhaloalkylsulfonylamino, polyhaloalkylcarbonylamino, trialkylsilyl, aryldialkylsilyl, triarylsilyl, sulfonic acid and derived salts, phosphonic acid and derived salts, alkoxycarbonylamino, alkylaminocarbonyloxy, Dialkylaminokarbonyloxygruppe, alkenyl, Polyhaloalkenyl, alkenyloxy, alkynyl, alkynyloxy, Polyhaloalkynyloxygruppe, Polyhaloalkynyl, Polyhaloalkenyloxj ^r group, Polyfluoroalkanol, Zyanoalkylaminogruppe, Semikarbazonomethyl, Alkoxykarbonylhydrazonomethyl, alkoxyiminomethyl, unsubstituted or substituted Aryloxyiminomethyl, hydrazonomethyl, unsubstituted or substituted Arylhydrazonomethyl, one with a mono-, di- - or polysaccharide condensed hydroxy group, haloalkyl, haloalkenyl, Haloalkynyl, alkoxyalkyl, aryloxy, aralkoxy, arylthio, Aral kyl thio group, alkylthioalkyl, arylt hioalkyl, arylsulfinyl, arylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, haloalkenyloxy, haloalkynyloxy, haloalkynylthio, haloalkenylsulfonyl, polyhaloalkenylsulfonyl, alkoxysulfonyl, aryloxysulfonyl, propargyloxy, aroyl, haloalkyl azyl, polyhaloazyl, aryloxycarbonyl, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, arylaminosulfonyl, carboxyalkoxy, carboxyalkylthio, alkoxycarbonylalkoxy, azyloxy, haloazyloxy, polyhaloazyloxy, aroyloxy, alkylsulfonyloxy, alkenylsulfonyloxy, arylsulfonyloxy, haloalkylsulfonyloxy, polyhaloalkylsulfonyloxy , aroylamino, Haloazylamino-, Alkoxykarbonyloxy-, arylsulfonylamino, Aminokarbonyloxy-, Zyanato-, Isozyanato-, Isothiozyano-, Zykloalkylaminogruppe, trialkylammonium, arylamino, Ari ^r amino- l- (alkyl), aralkylamino, Alkoxyalkylphosphinyl, Alkoxyalkylphosphinothioyl, Alkylhydroxyphoaphinyl, Dialkoxyphosphino, hydroxyamino, alkoxyamino, aryloxyamino, aryloxyimino, oxo, thiono, alkylaminoalkoxy, dialkylaminoalkoxy, alkoxy, alkoxy, alkoxyalkenyl, cyanoalkoxy, dialkylsulfonium, ™ \ A. y ⁼ Λ. 9 ™ * Λ SS »J) Ϊ1 -A- R ₃ , -P-Y ₂ R ₄ , -Y ₄ - P- Y ₂ R ₄ Y ₃ R ₅ or ^Y 2 ^R 4 wherein R-, R ₄ , R ₁ -, Y <, Y ₂ , Y-, »Y ₄ and X are as defined in claim 41. 54. The method according to claim 53, characterized in that R .. and R-, independently of one another, are a substituted or unsubstituted, carbocyclic or heterocyclic ring system which is selected from a heterocyclic, aromatic or nonaromatic ring system with the formula a bicyclic, aromatic or non-aromatic ring system having a formula selected from A ₂ IA ₃ Z Z a polycyclic, aromatic or non-aromatic Ring system with a formula that is selected from .A- Λ- Z. and a bridging ring system which may be saturated or unsaturated with a formula selected from * 13 wherein: A _{1 is} a ring-forming chain of atoms which together with B _{1 forms} a carbocyclic or heterocyclic ring system containing between 0 and 4 double bonds or between 0 and 2 triple bonds; B _{1 represents} a saturated or unsaturated carbon atom; A ₂ and A- independently represent a ring-forming chain of atoms which together with Bp and B- form a carbocyclic or heterocyclic ring system; A ₁₁ A ₁₃ A ₁₂ B ₂ and B- are independently a saturated or unsaturated carbon atom or a ± n saturated nitrogen atom; A., A ₁ -, Ag and Aj independently represent a ring-forming chain of atoms which together with B., B, -, Bg and B "form a carbocyclic or heterocyclic ring system; B ,, B (-, Bg and Bi are independently a saturated or unsaturated carbon atom or a saturated nitrogen atom; Ag, Aq and A..Q independently represent a ring-forming chain of atoms which, together with B ₃₉ B _n , B ₁₀ and B _{11 form} a carbocyclic or heterocyclic Ringaystem; Bo, Β "and B..Q independently represent a saturated or unsaturated carbon atom or a saturated nitrogen atom; B _{11 represents} a saturated or unsaturated carbon atom, nitrogen atom or phosphorus atom; A ₁₁ , A ₁₂ and A ₁₃ independently represent a ring-forming chain of atoms which together with B ₁₂ and B _{13 form} a carbocyclic or heterocyclic ring system; B ₁₂ and B _{13 are} independently a saturated carbon atom or a nitrogen atom, and Z is identical or different and one or more of the following is: hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, ihiozyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxy , Pormamidino, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, nitro, cyano, hydroxycarbonyl and derived salts, formamido, alkyl, alkoxy, polyhaloalkyl, polyhaloalkoxy, Alkoxycarbonyl, substituted amino group in which the permissible substituents are the same or different and one or two of the following: propargyl, alkoxyalkyl, alkylthioalkyl, alkyl, alkenyl, haloalkenyl or polyhaloalkenyl; Alkylthio, polyhaloalkylthio group, alkylsulfinyl, polyhaloalkylsulfinyl, alkylsulfonyl, polyhaloalkylsulfonyl, alkylsulfonyland.no-, alkylcarbonyl-amino, polyhaloalkylsulfonylamino, polyhaloalkylcarbonylamino, trialkylsilyl, aryldialkylsilyl, triarylsilyl, sulfonic acid and derived salts, phosphonic acid and derived salts, alkoxycarbonylamino, alkylaminocarbonyloxy , Dialkylaminocarbonyloxy group, alkenyl, polyhaloalkenyl, alkenyloxy group, alkynyl, alkynyloxy, polyhaloalkenyloxy group, polyhaloalkynyl, polyhaloalkynyloxy group, polyfluoroalkanol, cyanoalkylamino group, semicarbazonomethyl, alkoxycarbonylhydrazonomethyl, alkoxyiminomethyl, unsubstituted or substituted aryloxyiminomethyl, hydrazonomethyl, unsubstituted or substituted arylhydrazonomethyl, one with a mono-, di-, or polysaccharide condensed hydroxy group, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, aryloxy, aralkoxy, arylthio, aralkylthio, alkylthioalkyl, arylthio alkyl, Arylsulfin yes, arylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, HaIoalkenyloxy-, Haloalkynyloxy-, Haloalkynylthiogruppe, haloalkenyl sulf 'onyl, Polyhaloalkenylsulfonyl, alkoxysulfonyl, aryloxysulfonyl, propargyloxy, aroyl, Haloazyl, Polyhaloazyl, Aryloxykarbonyl, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, arylaminosulfonyl, Karboxyalkoxy- , Carboxyalkylthio, alkoxycarbonylalkoxy, azyloxy, haloazyloxy, polyhaloacyloxy, aroyloxy, alkylsulfonyloxy, alkenylolufonyloxy, arylsulfonyloxy, haloalkylsulfonyl oxy, polyhaloalkylsulfonyloxy, arylamino, Haloazylamino, alkoxycarbonyloxy, arylsulfonylavino, aminocarbonyloxy, cyanato, isocyanato, Icothiozyano, cycloalkylamino, trialkylammonium, arylamino, aryl (alkyl) amino, aralkylamino, alkoxyalkylphosphinyl, alkoxyalkylphosphinothioyl, alkylhydroxyphosphinyl, dialkoxyphoaphino, hydroxyairdno Alkoxyamino, aryloxyamino, aryloxyimino, oxo, thiono, alkylaminoalkoxy, dialkylaminoalkoxy, alkoxyalkoxy, alkoxyalkenyl, cyanoalkoxy, dialkylsulfonium,  y -X, = X, -X = R ₃ , = XR -XR ₃ , -P ^ Y ₂ R ₄ , -Y ₄ -P ^ Y ₂ R ₄ Y ₃ R ₅ ^Y 3 ^R 5. wherein R, R, R ₁ -, Y ..,
are defined. , Y ^, Y, and X as in claim Process according to claim 53, characterized in that the compound has the formula: wherein:. R 'is the same or different and represents one or more of the following: hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiozyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, aryldialkylsilyloxy, Triarylsilyloxy, pormamidino, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, nitro, cyano, hydroxycarbonyl and derived salts, formamido, alkyl, alkoxy, Polyhaloalkyl, polyhaloalkoxy, alkoxycarbonyl, substituted amino in which the permissible sub-substituents are the same or different and one or two of the following: propargyl, alkoxyalkyl, alkylthioalkyl, alkyl, alkenyl, haloalkenyl or polyhaloalkenyl; Alkylthio, polyhaloalkylthio group, alkylsulfinyl, polyhaloalkylsulfinyl, alkylsulfonyl, polyhaloalkylsulfonyl, alkylsulfonylamino, alkylcarbonylamino, polyhaloalkylsulfonylamino, polyhaloalkylcarbonylamino, trialkylsilyl, aryldialkylsilyl, triarylsilyl, sulfonic acid and derived salts, phosphonic acid and derived salts, alkoxacarbonylamino, alkylaminocarbonyl oxy, Dialkylaminocarbonyloxy group, alkenyl, polyhaloalkenyl, alkenyloxy group, alkynyl, alkynyloxy, polyhaloalkenyl oxy group, polyhaloalkynyl, polyhaloalkynyloxy group, polyfluoroalkanol, cyanoalkylamino group, semicarbazonomethyl, alkoxycarbonylhydrazonomethyl, alkoxyimino methyl, unsubstituted or substituted aryloxyiminomethyl, hydrazonomethyl, unsubstituted or substituted aryl-hydrazonometb.yl, a hydroxy group condensed with a mono-, di- or oligosaccharide, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, aryloxy, aralkoxy, azylthio, aralkylthio group, alkylthioalkyl, arylthioalkyl, arylsulfinyl, arylsulfonyl, haloalkylsulfinyl, haloalkyl sulfonyl, Halοalkenyloxy-, Haloalkynyloxy-, haloalkynyl thio group, Haloalkenylsulfonyl, Polyhaloalkenylsulfonyl, alkoxysulfonyl, aryloxysulphonyl, propargyloxy, aroyl, Haloazyl, Polyhaloazyl, Aryloxykarbonyl, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, arylaminosulfonyl, Karboxyalkoxy ^ , Carboxyalkylthio, alkoxycarbonylalkoxy, azyloxy, haloazirloxy, polyhaloazyloxy, aryloxy, alkylsulfonyloxy, AJ.kenylsulfonyloxy, arylsulfonyloxy, haloalkylsulfonyloxy, polyhaloalkylsulfonyloxy, aroylamino, haloazylamino, alkoxycarbonyloxy, arylsulfonylamino, aminocarbonyloxy y, cyanato, isocyanato, isothiozyano, cycloalkylamino, trialkylammonium, arylamino, aryl (alkyl) amino, aralkylamino, alkoxyalkylphosphinyl, alkoxyalkylphosphinothioyl, alkylhydroxyphosphinosphinyl, dialkoxyphosphino, hydroxyamino, alkoxyamino, aryloxyamino, aryloxyimino , Oxo, thiono, alkylaminoalkoxy, dialkylaminoalkoxy, alkoxyalkoxy, alkoxyalkenyl, cyanoalkoxy, dialkylsulfonium, -X, = X, -2 = R, = XR ₃ , Il H ¹ -X - R ₃ , - P- Y ₂ R ₄ , -X ₄ - P ^ Y ₂ R ₄ Y ₃ R ₅ .Y ₂ R ₄ Y ₃ R ₅ Y ₃ R ₅ XiJ O, S, SO, SO ₂ , MH, GH ₂ , CO, a single bivalent bond, CH ₂ O, CHgS, -CH (CH ₃ ) O, -CH (CW) O-, -CH = NO-, -C (CH ₃ ) = NO-, -CH ₂ CH ₂ O-, -CHgCHg-, -C = C-, -CHgSO-, -CHgSOg- -OCH ₂ CH ₂ O-, -CH ( Alkyl) - or -COMH- and Y ij and Y ₂ ^{1 are} independently alkyl, halogen or an alkoxy group; wherein X, R ₃ , R ₄ , R ₅ ,
are defined. Y, Y and Y. as in claim 41 56. The method according to claim 53, characterized in that the compound has the following formula: Ri and Ri are the same or different and Ri is one or more of the following: hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiozyano, propargylthio, hydroxyimino, alkoxyimino, trialkylailyloxy, aryldialkylsilyloxy, trialkylsilyloxy , Triarylsilylpxy, formamidino, alkylsulfamido, dialkylsulfamido, polyhaloalkoxysulfonyl, hydroxy, amino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, nitro, cyano, hydroxycarbonyl and derived salts, amoramido, alkyl, alkoxy, polyhaloalkyl , Polyhaloalkoxy group, alkoxy carbonyl, substituted amino group in which the permissible substituents are the same or different and one or two of the following: propargyl, alkoxyalkyl, alkoylthioalkyl, alkyl, alkenyl, haloalkenyl or polyhaloalkenyl5 alkylthio, polyhaloalkylthio, alkylsulfinyl, polyh aloalkylsulfinyl, Al kylsulfonyl, polyhaloalkylsulfonyl, alkylsulfonylamino ,. Alkylcarbonylamino, polyhaloalkylsulfonylamino, polyhaloalkylcarbonylamino group, Ti ¹ -alkylsilyl, aryldialkylsilyl, triarylsilyl, sulfonic acid and derived salts, phosphonic acid and derivative salts, alkoxycarbonylamino, alkylaminocarbonyloxy, dialkylaminocarbonyloxy group, alkenyl, polyhaloalkenyl, alkenyoxy group, alkynyl, alkynyoloxy, polyhaloalkenyloxy group, polyhaloalkynyl , Polyhaloalkynyloxy group, polyfluoroalkanaol, cyanoalkylamino group, semicarbazonomethyl, alkoxycarbonylhydrazonomethyl, alkoxyiminomethyl, unsubstituted or substituted aryloxyiminomethyl, hydrazonomethyl, unsubstituted or substituted arylhydrazonomethyl, a mono-, bi- or polysaccharide-fused hydroxy group, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, aryloxy, aralkoxy , Arylthio, aralkylthio, alkylthioalkyl,. Arylthioalkyl, arylsulfinyl, arylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, Halοalkenyloxy-, Haloalkynyloxy-, Haloalkynylthiogruppe, Haloalkenylsulfonyl, Polyhaloalkenylsulfonyl, Alkoxyaulfonyl, aryloxysulfonyl, propargyloxy, aroyl, Haloazyl, Polyhaloazyl, Aryloxykarbonyl, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, arylaminosulfonyl, Karboxyalkoxy-, Karboxyalkylthio-, Alkoxycarbonylalkoxy, azyloxs ^, haloazyloxy, polyhaloazyloxy, aroyloxy, alkylsulphonyloxy, alkenylsulphonyloxy, arylsulphonyloxy, haloalkylsulphonyloxy, polyhaloalkylsulphonyloxy, aroylamino, haloazylamino, alkoxycarbonyloxy, arylaulonylamino, aminocarbonyloxy, cyanato , Isocyanato, isothiocyanato, cycloalkylamino, trialkylammonium, arylamino, aryl (alkyl) amino, aralkylamino, alkoxyalkylphosphinyl, alkoxyalkylphosphinothioyl, alkylhydroxyphosphinyl, dialkoxyphosphino, hydroxyamino, alkoxyamino, aryloxyamino, aryloxyimino, oxo, thiono, Alkylaminoalkoxy, dialkylamine alkoxy, alkoxyalkoxy, alkoxyalkenyl, cyanoalkoxy, dialkylsulfonium, -X, "Ji., -Ji. ⁼ Rq, "A-R- ^, or 11 -XR ₃ , -PX ₂ R ₄ , -Y ₄ -PY ₂ R ₄ Y ₃ R ₅ Y ₃ R ₅ X ₂ is O, S, SO, SO ₃ , MH ₁ -CH ₂ , CO, a single bivalent bond, -GH (GH ₃ ) O-, -CH (ClT) O-, -CH = UO-,. -C (CH ₃ ) = 1TO-, -CH ₂ CH ₂ O-, -C = C-, -CH ₂ SO- or -CH ₂ SO ₂ - is and YI is halogen, wherein X, R, R, R ₁ -, Y ..,
are defined. Y, and Y. as in claim 41 Process according to claim 53, characterized in that the compound has the formula: wherein R ', RJ and R £ are the same or different and RJ is one or more of the following: hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiozyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy -, Aryldialkylsilyloxy-, (Priacalloxy-, formamidino-, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, Nitro, cyano group, hydroxy carbonyl and derived salts, formamido group, alkyl, alkoxy group, polyhaloalkyl, polyhaloalkoxy group, alkoxy carbonyl, substituted amino group in which the permissible substituents are identical or different and one or two of the following: propargyl, alkoxyalkyl, alkylthioalkyl, alkyl, Alkenyl, haloalkenyl or polyhaloalkenyl; Alkylthio, Polyhaloalkylthiogruppe, alkylsulfinyl, Polyhaloalkyl3Ulfinyl, alkylsulfonyl, Polyhaloalkylsulfonyl, alkylsulfonylamino, Alkylkarbonylamino-, Polyhaloalkylsulfonylainino-, Polyhaloalkylkarbonylaminogruppe, trialkylsilyl, aryldialkylsilyl, Triarylailyl sulfonic acid and derivative salts, phosphonic acid and derivative salts, Alkoxykarbonylamino-, Alkylaminokarbonyloxy-, Dialkylaminokarbonyloxygruppe, alkenyl, Polyhaloalkenyl, alkenyloxy group, alkynyl, alkynyloxy, polyhaloalkenyloxy group, polyhaloalkynyl, polyhaloalkynyloxy group, polyfluoroalkanal, cyanoalkylamino group, semicarbazonomethyl, alkoxycarbonylhiydrazonomethyl, alkoxyiminomethyl, unsubstituted or substituted aryloxyiminomethyl, hydrazonomethyl, unsubstituted or substituted arylhydrazonomethyl, a mono-, di- or polysaccharide-fused hydroxy group, Haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, aryloxy, aralkoxy, arylthio, aralkylthio, alkylthioalkyl, arylthioalky l, arylsulfinyl, arylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, Haiοalkenyloxy-, Haloalkynyloxy-, Haloalkynylthiogruppe, Haloalkenylsulfonyl, Polyhaloalkenylsulfonyl, AIkoxysulfonyl, aryloxysulfonyl, propargyloxy, aroyl, Haloazyl, Polyhaloazyl, Aryloxykarbonyl, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, arylaminosulfonyl, Alkoxykarbonylakoxy-, Karboxyalkoxy-, Carboxyalkylthio, azyloxy, haloazyloxy, polyhaloazyloxy, aroyloxy, alkylsulphonyloxy, alkenylsulphonyloxy, arylsulphonyloxy, haloalkylsulphonyloxy, polyhaloalkylsulphonyloxy, aroylamino, haloazylamino, alkoxycarbonyloxy, arylsulphonylamino, aminocarbonyloxy, cyanato, isocyanato , Isothiocyanato, cycloalkylamino, trialkylammonium, arylamino, aryl (alkyl) amino, aralkylamino, alkoxyalkylphosphinyl, alkoxyalkylphosphinothioyl, alkylhydroxyphosphinyl, dialkoxyphosphino, hydroxyamino, alkoxyamino, aryloxyamino, aryloxyimino, oxo, thiono, alkylaminoalkoxy, Dialkylaminoalkoxy, Alko xyalkoxy group, alkoxyalkenyl, dialkylsulfonium, cyanoalkoxy group, -X - R. XT _ T) X-R, ^Y 3 ^R 5 Y ₂ R ₄ ^Y 3 ^R 5_ and Γ-Ϊ2 »4 X 'is 0, S, SO, SO _2, NH, CH _2, GO, a single divalent bond, -GH _(CH3) O-, -CH (CW) O-, -CH = NO-, -G (CH ₃ ) = NO-, -CH ₂ CH ( or -CONH-; _3
2 CH ₂ O-, -C = C-, -CH ₂ SO-, -C ₃ -, -OGHgCHgO-, -CH (alkyl) - wherein X, R ₃ , R ₄ , R ₅ , Υ., ·, Y ₂ , Y ^ and Y _{4 are} as defined in claim 41. 58. The method according to claim 53 »characterized in that the compound has the following formula: wherein: Υ », Yi, YJ, Yi and ΥΛ are the same or different and are the following: hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiozyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, aryldialkyl siiyioxy, triarylsilyloxy, lmmamidino, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, nitro, cyano, hydroxycarbonyl, and derived salts, amoramido, alkyl, alkoxy , Polyhaloalkyl, polyhaloalkoxy, alkoxylcarbonyl, substituted amino in which d3.e substituents are the same or different and one or two of the following: propargyl, alkoxyalkyl, alkylthioalkyl, alkyl, alkenyl, haloalkenyl or polyhaloalkenyl; Alkyl thio, polyhaloalkyl thio, alkylsulfinyl, Polyhaloalkylsulfinyl, alkylsulfonyl, Polyhaloalkylsulfonyl, alkylsulfonylamino, Alkylkarbonylamino-, Polyhaloalkylsulfonylamino-, Polyhaloalkylkarbonylaminogruppe, trialkylsilyl, aryldialkylsilyl, Triarylsilsrl, Suflonsäure and derived salts, phosphonic acid and derivative salts, Alkoxykarbonylamino-, Alkylaminokarbonyloxy-, Dialkylaminokarbonyloxygruppe, Alkenyl, polyhaloalkenyl, alkenyloxy, alkynyloxy group, alkynyl, polyhaloalkenyloxy group, polyhaloalkynyl, polyhaloalkynyloxy group, polyfluoroalkanol, cyanoalkylaraino group, semicarabzonomethyl, alkoxycarbonylhydrazonomethyl, alkoxyiminomethyl, unsubstituted or substituted aryloxyiminomethyl, hydrazonomethyl, unsubstituted or substituted arylhydrazonomethyl, a hydroxy group condensed with a mono-, di- or polysaccharide , Ilaloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, aryloxy, aralkoxy, arylthio, aralkylthio, alkylthioalkyl, arylthi oalkyl, arylsulfinyl, arylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, haloalkenyl oxy, haloalkynyloxy, haloalkynylthio, haloalkenylsulfonyl, polyhaloalkenylsulfonyl, alkoxysulfonyl, aryloxysulfonyl, propargyloxy, aroyl, haloazyl, polyhaloazyl, aryloxycarbonyl, aminosulfonyl, alkylamin sulfonyl; Dialkylamino sulfonyl, acylamino sulfonyl, liarboxyalkoxy, Karboxyalkylthio-, alkoxy carbonylalkoxy, azyloxy, haloazyloxy, polyhaloazyloxy, aroyloxy, alkylsulphonyloxy, alkenylsulphonyloxy, arylsulphonyloxy, haloalkylsulphonyloxy, polyhaloalkylsulphonyloxy, aroylamino, haloazylamino, alkoxycarbonyloxy, arylsulphonylamino, aminocarbonyloxy, cyanato, isocyanato , Isothiocyanato, cycloalkylamino, trialkylammonium, arylamino, aryl (alkyl) amino, aralkylamino, alkoxyalkylphosphinyl, alkoxyalkylphosphinothioyl, alkylhydroxyphosphinyl, dialkoxyphosphino, hydroxyamino, alkoxyamino, aryloxyamino, aryloxyimino, oxo, thiono, alkylaminoalkoxy, Dialkylaminoalkoxy, alkoxyalkoxy, alkoxyalkenyl, cyanoalkoxy, dialkylsulfonium, -X, = X, -X ⁼ R ο s = XR ~, -Υ - R - P - -Λ - OJ, £ - Y ₃ R ₅ , -Y ₄ -PY ₂ R ₄ Y ₃ R ₅ Y ₂ R ₄ Y ₃ R ₅ Y 'YJq, YJ λ and Yl _{2 are the} same or different and are hydrogen, halogen, alkyl, polyhaloalkyl, a cyano group or aryl; m 'and n' are the same or different and have a value of 0 to 5; X 'is O, S, SO, SO ₂ , H, CH ₂ , CO, a single, bivalent bond, -CH (CH ₃ ) O-, -CH (CN) O-, -CII = NO-, -C (CH ₃ J = NO, -CHgCHgO-, -C = C-, -CHgSO-, -OCH ₂ CH ₂ O-, -CH (alkyl) - or -CONH- is and Yi ₃ and Y; j. are the same or different and are halogen, alkyl or an alkoxy group; wherein X, R ₃ , R,
are defined. , Yg, - Y ₃ and Y. as in claim 41 Method according to claim 53, characterized in that the compound has the following formula: T χ. ^L 92 10 m » wherein: Y ', Y1, Y1, Y1 and YK are the same or different and the following are: hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiozyano, propargylthio, hydroxyimino, alkoxymimino, trialkylsilyloxy, Aryldialkylsilyloxy, triarylsilyloxy, iormamidino, alkylsulfamido, dialkylsulfarnxdogruppe, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino, aminocarbonyl, alkylamino! Carbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaroinothiocarbonyl, nitro, cyano, hydroxycarbonyl and derived salts, Formamido group, alkyl, alkoxy group, polyhaloalkyl, polyhaloalkoxy group, alkoxycarbonyl, substituted amino group in which the permissible substituents are the same or different and one or two of the following: propargyl, alkoxyalkyl, alkylthioalkyl, alkyl, alkenyl, haloalkenyl or polyhaloalkenyl; Alkylthio, Polyhaloalkylthiogruppe, alkylsulfinyl, Polyhaloalkylsulfinyl, Alkylaulfonyl, Polyhaloalkylsulfonyl, alkylsulfonylamino, Alkylkarbonylamino-, Poiyhaloalkylsulfonylamino-, Polyhaloalkylkarbonylaminogruppe, trialkylsilyl, aryldialkylsilyl, triarylsilyl Sulfoneäure and derivative salts, phosphonic acid and derivative salts, Alkoxykarbonylamino-, Alkylaminokarbonyloxy-, Dialkylaniinokarbonyloxygruppe, alkenyl, Polyhaloalkenyl, alkenyloxy group, alkynyl, alkynyloxy, polyhaloalkenyloxy group, polyhaloalkynyl, polyhaloalkynyloxy group, polyfluoroalkanol, cyanoalkylamino group, semicarbazonomethyl, alkoxycarbonyihydrazonomethyl, alkoxyiminomethyl, unsubstituted or substituted aryloxyiminomethyl, hydrazonomethyl, unsubstituted or substituted arylhydrazonomethyl, a mono-, di- or polysaccharide-fused hydroxy group , Haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, aryloxy, aralkoxy, arylthio, aralkylthio, alkylthioalkyl, arylthioal kyl, arylsulfinyl, arylsulfonyl, haloalkylsulfinyl, HaIoalkylsulfonyl, Haloalkenyloxy-, Haloalkynyloxy-, Haloalkynylthiogruppe, Haloalkenylsulfonyl, Polyhaloalkenylsulfonyl, alkoxysulfonyl, aryloxysulfonyl, propargyloxy, aroyl, Haloazyl, Polyhaloazyl, Aryloxykarbonyl, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, Arylaminoaulfonyl, Karboxyalkoxy-, Karboxyalkylthio-, Alkoxycarbonylalkoxy, Azyloxy, Haloazyloxy, Polyhaloazyloxy, Aroyloxjr ,. Alkylsulfonyloxy, alkenylsulfonyl oxy, arylsulfonyloxy, haloalkylsulfonyloxy, polyhaloalkylsulfonyloxy, aroylamino, haloazylamino, alkoxycarbonyl oxy, arylsulfonylamino, amino! Carbonyloxy, cyanato, isocyanato, isothiocyanato, cycloalkylamino, trialkylanemonium, arylamino , Aryl (alkyl) amino, aralkylamino, alkoxyalkylphosphinyl, alkoxyalkylphosphinothioyl, alkylhydroxyphosphinyl, dialkoxyphosphino, hydroxyamino, alkoxyimino, aryloxyamino, aryloxyimino, oxo, thiono, alkylarninoalkoxy, dialkylaminoalkoxy, alkoxyalkoxy, alkoxyalkenyl, cyanoalkoxy, dialkylsulfonium, -X, = X, -X = R ₃ , = XR ₃ , -XR ₃ , - PY ₂ R ₄ , -Y ₄ -PY ₂ R ₄
^Y 3 ^R 5 ^Y 3 ^R 5 ^Y 2 ^R 4 Y ₃ R ₅ Yg and YJq are the same or different and are hydrogen, halogen, alkyl, polyhaloalkyl, a cyano group or aryl; m 'and n' are the same or different and have a value between 0 and 5; Xi is the same or different and 0, S, SO, SOg, MI, GHg, GO, a single divalent bond, -CH (CI] U) O-, -CH (GN) O-, -GH = NO-, - C (CH ₃ ) = NO, -CHgCHgO-, -C = C-, -GH ₂ SO-, -CH ₂ SO ₂ -T -OGH ₂ GH ₂ O-, -CH (alkyl) - or -CONH- corresponds; YIj ₅ is 0 or S; Yi .. and Yi _{2 are} independently halogen and X £ is equal to 0 or S; wherein X, R ₃ , R, R ₅ , Y ₁ , Y ₂ , Y-, and Y are as defined in claim 41. 60. The method according to claim 53, characterized in that the compound has the following formula:  93 jd ^l 94 wherein: Yi, Yi, Y, Yi and Yi are the same or different and are hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiozyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, aryldialkyloilyloxy , Triarylsilyloxy, pormamidino, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, arabic, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, nitro, cyano, hydroxycarbonyl and derived salts, lormaredio, alkyl, alkoxy, Polyhaloalkyl, polyhaloalkoxy group, alkoxycarbonyl, substituted amino group in which the permissible substituents are the same or different and one or two of the following: propargyl, alkoxyalkyl, alkylthioalkyl, alkyl, alkenyl, haloalkenyl or polyhaloalkenyl; Alkylthio, polyhaloalkylthio group, alkylsulfinyl, polyhaloalkylsulfinyl, 'alkylsulfonyl, polyhaloalkylsulfonyl, alkylsulfonylamino, alkylcarbonylamino, polyhaloalkylsulfonylamino, polyhaloalkylcarbonylamino, 3-aralkylsilyl, aryldialkylsilyl, triarylsilyl,' sulfonic acid and derived salts, phosphonic acid and derived salts, alkoxycarbonylamino, alkylaminocarbonyloxy, Dialkjaminocarbonyloxy group, alkenyl, polyhaloalkenyl, alkenyloxy group, alkynyl, alkynyloxy, polyhaloalkenyloxy group, polyhaloalkynyl, polyhaloalkynyloxy group, polyfluoroalkanol, cyanoalkylamino group, semicarbazonomethyl, alkoxycarbonylhydrazonomethyl, alkoxyiminomethyl, unsubstituted or substituted aryloxyiminomethyl, hydrazonomethyl, unsubstituted or substituted arylhydrazonomethyl, one having a mono-, Di- or polysaccharide condensed hydroxy group, Haloalkyl, haloalkenyl, Ilaloalkynyl, alkoxyalkyl, aryloxy, aralkoxy, arylthio, aralkylthio, alkylthioalkyl, arylthi oalkyl, arylsulfinyl, arylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, haloalkenyloxy, haloalkenyloxy, Haloallcynyloxy-, Haloalkynylthiogruppe, Haloallcenylsulfonyl, Polyhaloalkenylsulfonyl, Alkoxysulfonyl, aryloxysulphonyl, propargyloxy, aroyl, Haloazyl, Polyhaloazyl, Aryloxykarbonyl, aminosulfonyl, alkylaminosulfonyl, dialkyl amino sulfonyl, arylaminosulfonyl, Karboxyalkoxy-, Karboxyalkylthio-, Alkoxykarbonylalkoxy-, Azyloxy-., HaIoazyloxy-, Polyhaloazyloxy , Aroyloxy, alkylsulfonyloxy, alkenylsulfonyloxy, arylsulfonyloxy, haloalkylsulfonyloxy, polyhaloalkylsulfonyloxy, aroylamino, haloazylamino, alkoxycarbonyloxy, arylsulfonylamino, aminocarbonyloxy, cyanato, isocyanato, isothiocyano, cycloalkylamino, trialkylammonium , Arylamino, aryl (alkyl) amino, aralkylamino, alkoxyalkylphosphinyl, alkoxyalkylphosphinothioyl, alkylhydroxyphosphinyl, dialkoxyphosphino, hydroxyamino, alkoxyamimo, aryloxyamino, aryloxyimino, oxo, thiono, alkylaminoalkoxy, dialkylaminoalkoxy, alkoxyalkoxy, alkoxyalkenyl, Zyanoalkoxygrup-pe, dialkylsulfonium, , -X = -XR ₃ , - ^ oj Y ₃ R ₅ Y ₂ R ₄ Y ₃ R ₅ X 'is the same or different and 0, S, SO, SO ₂ , Mi, CH ₂ , CO, a single bivalent bond, -CH (CHOO-, -CH (CN) O-, -CH = NO-, -C (CH ₃ ) = 1 * 0, -CHgCHgO-, -C = C-, -CHgSO-, -CH ₂ SO ₂ -, -OCH ₂ CH ₂ O-, -CH (alkyl) - or -CONH- represents ; m 'is a value between 0 and 5; Y'g ₃ and Y'g _{4 are} independently halogen; Y 'is ₁₆ % A, alkyl, alkylcarbonyl, alkylsulfonyl or polyhaloalkylsulfonyl; wherein X, R ₃ , R, R ", Y ₁ , Y ₃ , Y ₃ and Y _{4 are} as defined in claim 41. 61. The method according to claim 53, characterized in that the compound has the following formula: γ " worxn: Y '., Y'cj Y'g' Y 7 ¹⁰¹ ^ l Y'g are the same or different and the following are: V / asaerstoff, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiozyano, propargylthio , hydroxyimino, alkoxyimino, trialkylsilyloxy, Aryldialkylsilyloxy-, triarylsilyloxy, Fromaraidino-, Alkylsul- £ amido, Dialkylsulfamidogruppe, alkoxysulfonyl, polyhalo- alkoxysulfonyl, hydroxy, amino, aminocarbonyl, alkylaminocarbonyl, dialkylamino carbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, nitro, cyano, hydroxycarbonyl and derived salts, formamido, alkyl, alkoxy, polyhaloalkyl, polyhaloalkoxy, alkoxycarbonyl, substituted amino in which the permissible substituents are the same or different and one or two of the following are / propargyl, alkoxyalkyl, alkylthioalkyl, alkyl, alkenyl, haloalkenyl or polyhaloalkenyl; Alkylthio, Polyhaloalkylthiogruppe, alkylsulfinyl, Polyhaloalkylsulfinyl, alkylsulfonyl, Polyhaloalkylsulfonyl, alkylsulfonylamino, Alkyllcarbonylamino-, Polyhaloalkylsulfonylamino-, Polyhaloalkylkarbonylaminogruppe, trialkylsilyl, aryldialkylsilyl, triarylsilyl sulfonic acid and derivative salts, phosphonic acid and derivative salts, Alkoxykarbonylamino-, Alkylaminokarbonyloxy-, Dialkylaminokarbonyloxygruppe, alkenyl, Polyhaloalkenyl, alkenyloxy group, alkynyl, alkynyloxy, polyhaloalkynyloxy group, polyhaloalkynyl, polyhaloalkenyloxy group, polyfluoroalkanol, cyanoalkylamino group, semicarbazonomethyl, alkoxycarbonylhydrazonomethyl, alkoxyirainomethyl, unsubstituted or substituted aryloxyiminomethyl, hydrazonomethyl, unsubstituted or substituted arylhydrazonomethyl, one with a mono-, di- or polysaccharide fused hydroxyl group, haloalkyl, haloalkylene, haloalkynyl, alkoxyalkyl, aryloxy, aralkoxy, arylthio, aralkylthio, alkylthioalkyl, arylthio alkyl, arylsulfinyl, arylsulfonyl, haloalkylsulfinyl, haloalkyl sulfonyl, thio group Haloalkenyloxy-, Haloalkynjrioxy-, haloalkynyl, Haloalkenylsulfonyl, Polyhaloalkenylsulfonyl, alkoxysulfonyl, aryloxysulfonyl, propargyloxy, aroyl, Haloazyl, Polyhaloazyl, Aryloxykarbonyl, aminosulfonyl, alkylaminosulfonyl, Diallcylaminosulfonyl, arylaminosulfonyl, Karboxyalkoxy-, Karboxyalkylthio , Alkoxycarbonylalkoxy, azyloxy, haloazyloxy, polyhaloazyloxy, aroyloxy, alkylsulfonyloxy, alkenylsulfonyloxy, arylsulfonyloxy, haloalkylsulfonyloxy, polyhaloalkylsulfonyloxy, aroylamino, halpazylamino, alkoxycarbonyloxy, arylsulfonylamino, aminocarbonyloxy, cyanato, , Isozyanato-, Isothiozyano-, Zykloalkylaminogruppe, Trialkj ^r lammonium, arylamino, aryl (alkyl) amino, aralkylamino, Alk oxyalkylphosphinyl, Alkoxyalkylphosphinothioyl, Alkylhydroxyphosphinyl, Dialkoxyphosphino-, hydroxyamino, AIkoxyamino-, Aryloxyamino-, Aryloxyimino-, oxo, Thiono, alkylaminoalkoxy, dialkylaminoal koxy, alkoxyalkoxy, alkoxyalkenyl, cyanoalkoxy, dialkylsulfonium, -X, -λ, -α = H-J-X-R_, -X - R. i ¹ 'ΐ ¹ , - P - ΥΛΧ., - Y , - P - Y ₀ R, "2" 4 · 4 ; and and Y 'qg are independently halogen, vrorin X, R_, R, R, -, Y .., Yp, Yo and Y. as defined in FIG. (fit,) 62. The method according to claim 53, characterized in that the compound has the following Israel: worm: Y i ς and YA _{1 are} identical or different and Y ₁ "is one or more of the following: hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiozyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, Aryldialkylsilyloxy, · trialkylsilyloxy, κκα-amidino, alkylsulfarnido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, nitro, cyano, hydroxycarbonyl and derived salts, imideamido groups Alkyl, alkoxy group, polyhaloalkyl, polyhaloalkoxy group, alkoxycarbonyl, substituted amino group in which the permissible substituents are the same or different and one or two of the following: propargyl, alkoxyalkyl, alkylthioalkyl, alkyl, alkenyl, haloalkenyl or polyhaloalkenyl; Alkylthio, polyhaloalkylthio group, alkylsulfinyl, polyhaloalkylsulfinyl, alkylsulfonyl, polyhaloalkylsulfonyl, alkylsulfonylamino, alkylcarbonylamino, polyhaloalkylsulfonylamino, polyhaloalkylcarbonylamino, trialkylailyl, aryldialkylailyl, triarylailyl, sulfonic acid and derived salts, phosphonic acid and derived salts, alkoxycarbonylamino, alcylananocarbonyloxy, dialkylaminocarbonyloxy group, Alkenyl, polyhaloalkenyl, alkenyloxy group, alkynyl, alkynyloxy, polyhaloalkenyloxy group, polyhaloalkynyl, polyhaloalkynyloxy _group , polyfluoroalkanol, cyanoalkyaamino group, semicarbazonomethyl, alkoxycarbonylhadrazonomethyl, alkoxyirninomethyl, unsubstituted or substituted aryloxyiminomethyl, hydrazonomethyl, unsubstituted or substituted arylhydrazonomethyrl, one with a mono-, di- or Polysaccharide condensed hydroxy group, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, aryloxy, aralkoxy, arylthio, aralkylthio, alkylthioalkyl, arylth ioalkyl, arylaulphinyl, arylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, haloalkenyl oxy, haloalkynyloxy, haloalkynylthio, haloalkenylsulfonyl, polyhaloalkenylsulfonyl, alkoxysulfonyl, aryloxysulfonyl, propargyloxy, aroyl, halazyl, polyhaloazyl, aryl oxy! carbonyl, amino sulfonyl, alkylaminoaulfonyl , dialkyl amino sulfonyl, sulfonyl arylamino, Karboxyalkoxy- 'Karboxyalkylthio-, Alkoxykarbonylalkoxy-, Azyloxj ^r -, Haloazyloxy-, Polyhaloazyloxy-, aroyloxy, alkylsulfonyloxy, Alkenylsulfonyloxj "-, aryl sulfonyl oxy, Haloalkylsulfonyloxy -,' Polyhaloalkylsulfonyloxy- , Aroylamino, haloacylamino, alkoxycarbonyl oxy, arylsulphonylamino, aminocarbonyloxy, cyanato, isocyanato, isothiozyano, cycloalkylamino, trialkylammonium, arylamino, aryl (alkydamino, aralkylamino, alkoxyalkylphosphinyl, Alkoxyalkylphosphinothioyl, alkylhydroxyphoaphinyl, dialkylphosphino, hydroxyamino, alkoxyamino, aryloxyimino, aryloxyamino, oxo, thiono, arylalkylaminoalkoxy, dialkylaminoalkoxy, alkoxyalkoxy, alkoxyalkenyl, cyanoalkoxy, dialkyrisulfonium, , , -Λ - R ^, - X-R ^ j, II ¹ II ¹ , - P ^ Y ₂ R ₄ , -Y ₄ - P - Y ₂ R ₄ X ₃ R ₅ Y ₃ R ₅ ^Y 2 ^R 4 A 'is defined as R.J in claim 41; X '.J ₀ as X is defined in claim 41 and Y'20 is halogen, a cyano group, alkyl, an alkoxy group, polyalkyl, a polyhaloalkoxy or polyhaloalkylsulfonyloxy group; wherein X, R_, R _4, R ^, Y ^, Y _2, Y_ and Y ₄ are as defined in claim 41st 63. The method according to claim 53, characterized in that the compound has the following formula: Y'X ₂₂ 23 wherein: R'22 like defined in point 42; Y _{22 is} halogen, a cyano group, alkyl, an alkoxy group, polyhaloalkyl, a polyhaloalkoxy group or a polyhaloalkylsulfonyloxy group, and Y'go hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiozyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxy, diminamidino, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, Polyhaloalkoxysulfony, hydroxy, amino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaiothiocarbonyl, dialkylaminothiocarbonyl, keto, cyano, hydroxycarbonyl and derived salts, boronamido, alkyl, alkoxy, polyalkyl, polyhaloalkoxy, alkoxycarbonyl, substituted amino, in which the permissible substituents are the same or different and one or two of the following are: propargyl, alkoxyalkyl, alkylthioalkyl, alkyl, alkenyl, haloalkenyl, polyhaloalkenyl; Alkylthio, Pölyhaloalkylthiogruppe, alkylsulfinyl, PoIyhaloalkylsulfinyl, alkylsulfonyl, Pölyhaloalkylsulfonyl, alkylsulfonylamino, Alkylkarbonylamino-, Polyhaloalkylsulfonylamino-, Polylialoalkylkarbonylaminogruppe, trialkylsilyl, aryldialkylsilyl, triarylsilyl, sulfonic acid and salts derived Phoophonsäure and salts derived, AIkoxykarbonylamino-, Alkylaminokarbonyloxy-, dialkylamino karbonyloxy group, alkenyl, polyhaloalkenyl, alkenyloxy group, alkynyl, alkynyloxy, polyhaloalkenyloxy group, polyhaloalkynyl, polyhaloalkynyloxy group, polyfluoroalkanol, cyanoalkylanilano group, semicarbazone toethyl, alkoxycarbonylhydrazonomethyl, alkoxyimnomethyl, unsubstituted or substituted aryloxyiniinomethyl, hydrazonomethyl, unsubstituted or substituted arylhydrazonomethyl, one with a mono-, di- or polysaccharide condensed hydroxy, haloalkyl, haloalkenyl, HaIoalkynyl, alkoxyalkyl, aryloxy, aralkoxy, arylthio, aralkylthio, AlkyIthiοalkyl, arylthioalkyl, arylsulfinyl, arylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, Haloalkenyloxy-, Haloalkynyloxy-, Haloalkynylthiogruppe, Haloalkenylsulfonyl, Polyhaloalkenylsulfonyl, alkoxysulfonyl, aryloxysulfonyl , Propargyloxy group, aroyl, haloacyl, polyhaloazyl, aryloxycarbonyl, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, arylaminosulfonyl, carboxyalkoxy, carboxyalkylthio, alkoxycarbo nylalkoxy, azyloxs ^, haloazyloxy, polyhaloazyloxy, aroyloxy, alkylsulfonyloxy, alkenylsulfonyloxy, arylsulfonyloxy, haloalkylsulfonyloxy, polyhaloalkylsulfonyloxy, aroylamino, haloazylamino, alkoxycarbonyloxy, arylsulfonylamino, aminocarbonyloxy, cyanato, isocyanato -, Isothiozyano-, Cycloalkylaniinogruppe, Trialkylammonium, Arylamino-,. Aryl (alkyl) amino, aralkylamino, jukoxyalkylphosphinyl, alkoxyalkylphosphinothioyl, alkylhydroxyphosphinyl, dialkoxyphosphino, hydroxyamino, alkoxyamino, aryloxyamino, aryloximino, oxo, thiono, alkylaminoalkoxy, dialkylarainoalkoxy, alkoxyalkoxy, alkoxyalkenyl, cyanoalkoxy, dialkylsulfoniuia . -A, = A, -A- ti- ,, - AK ^ ₁ -XR ₃ , -P- Y ₂ R ₄ , -Y ₄ - P- Y ₂ R ₄ is; ^Y 3 ^R 5 - wherein X, R ₃ , R ₄ , R ₅ , Y ₁ , Y ₂ , Y ₃ and Y _{4 are} as defined in claim. A method according to claim 53, characterized in that the compound has the formula: wherein: A '.. as Ri is defined in claim 41 and Y 'and Y'. are the same or different and are halogen, alkyl or an alkoxy group. 65. The method according to claim 53, characterized in that the compound has the following formula: Γ24- ^X 12- \ Q> Ν- < γ " Y ' ^Χ 34 wherein: A'2 as defined in claim 41 RJ; X ».j2 ^{V |} ö- ^e X ^ n is defined in claim 41 and Y'03 and Y'j . are the same or different and are halogen, alkyl, an alkoxy group. 66. The method of claim 53> characterized in that the compound has a formula selected from: ^X 49s ( ^Χ 47 ^{Υ 61γ} / ^Υ 6 ₂ where Y ', 44 »* 45» > γ> γ »γ» 46 ' ^χ 47' 48 ' ^χ 49' V »Y» Y »Y» Y »Y» Y 'Y' YII 50 ' ^ί 51' 48 ' ^x 52' ^x 53 '54' 55 '56' 57 '59' are and Y ' 59 » ^ '62 ß -'- ^e ^ ^c ' ^{: 1} or different ₄₁ ^{Y> 52'Y>} 56 ^Y> 59 ^{a or} more of the following are: hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiozyano, propargylthio, hydroximino, alkoxyimino, trialkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxy, formamidino, alkylsulfamido, dialkylsulfamido, Alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, uitro, cyano, hydroxycarbonyl and derived salts, formamido, alkyl, alkoxy, polyhaloalkyl, polyhaloalkoxy, alkoxycarbonyl, substituted amines in which the permissible Substituents the same or different and one or two of the following are: propargyl, alkoxyalkyl, alkylthioalkyl, alkyl, alkenyl, haloalkenyl or polyhaloalkenyl, j alkylthio, polyhaloalkylthio group, alkylsulfinyl, polyhaloalkylsulfinyl, alkylsulfonyl, polyhaloalkylsulfo nyl, alkylsulfonylamino, alkylcarbonylamino, polyhaloalkylsulfonylamino, polyhaloalkylcarbonylamino, trialkylsilyl, aryldialkylsilyl, tri- arylail5 ^r l, sulfonic acids and derived salts, pho phonic acid and derived salts, alkoxycarbonylamino, alkylaminocarbonyloxy, dialkylaminocarbonyloxy, alkenyl, polyhaloalkenyl, alkenyloxy, alkynyl, allcynyloxy,. Polyhaloalkenyloxy group, polyhaloalkynyl, polyhaloalkynyloxy group, polyfluoroalkanol, cyanoalkylamino group, semicarbazonomethyl, alkoxycarbonylhydrazonomethyl, alkoxyiminomethyl, unsubstituted or substituted aryloxyiminomethyl, hydrazonomethyl, unsubstituted or substituted arylhydrazonomethyl, a mono-, di- or polysaccharide-fused hydroxy group, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, aryloxy -, aralkoxy, arylthio, aralkylthio, alkylthioalkyl, arylthioalkyl, arylsulfinyl, arylsulfonyl, haloalkylsulfinyl, Haloakylsulfonyl, Haloalkenyloxy-, Haloalkynyloxy-, Haloalkynylthiogruppe, Haiοalkenylsulfonyl, Polyhaloalkenylsulfonyl, Alkoxysulfonjrl, aryloxysulphonyl, propargyloxy, aroyl, Haloazyl, Polyhaloazyl, Aryloxykarbonyl, aminosulfonyl, Alkylaminosulfonyl, dialkylaminosulfonyl, arylaminosulfonyl, carboxyalkoxy, carboxyalkylthio, alkoxycarbonylalkoxy, azyloxy, haloazyloxy, polyhaloazyloxy, aroyloxy, alkylsulfonyloxy, alken nylsulfonyloxy, arylsulfonyloxy, haloalkylsulfonyloxy, polyhaloalkylsulfonyl oxy, aroylamino, haloazylamino, alkoxycarbonyloxy, arylsulfonylamino, aminocarbonyloxy, cyanato, isocyanato, cycloalkylamino, trialkylammonium, arylamino, aryl (alkyl) amino, aralkylarnino, Alkoxyalkylphosphinyl, AlkoxyalkylphoapbJ.no thioyl, Alkylh.ydroxyph.osph.inyl, Dialkylaminoalkoxy-, Dialkoxyphosphino-, hydroxyamino, alkoxyamino, Aryloxyimino-, Arj ^r loxyamino-, oxo, thiono, alkylaminoalkoxy, Dialkylarninoalkoxy-, alkoxyalkoxy, AIkoxyalkenyl , Cyanoalkoxy group, dialkylsulfonium, -X, = X, -X = E ₁ , = X-Ro, Y ₁ "1 II ¹ " -XR ^, - P ³ \ -Y ₂ R ₄
Y ₃ R ₅ ^Y 2 ^R 4 A ' ₄ , A'ci A'g, A'_7>A'g and A ' _{g are defined} as R ^ in claim 41, and X _'14, X' ₁₅ ' ' ^X ' i8 ^{and X} 'i9 S ^{light or} different the are and O, S, SO, SOG, NH, CHg, CO, a single divalent bond, -CH (CH ₃₎ O-, -CH (CII) O-, -CH = NO-, -O (CH ) = NO-, -CH ₂ CH ₂ O-, -C = C-, -CHgSO-, CHgSOg, OCHgCHgO-, -CH (alkyl) - or -CONH-; wherein X, R ₃ , R, R ₅ , Y ₁ , Y ₂ , Y ₃ , Y _{4 are} as defined in claim 41. 67. The method according to claim 53, characterized in that the compound has the following formula: '64 A '..Q as R ^ is defined in claim 41, as X is defined in claim 41, X'i ^ is a substituted or unsubstituted, five-membered heterocyclic ring system having at least one nitrogen atom in which the permissible substituents are the same or different and one or more of the following: hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, Thiozyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxy, formamidino, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylamino, thiocarbonyl , Dialkylaminothiokarbonyl, nitro, cyano group, hydroxy carbonyl and derived salts, lormamido group, alkyl, alkoxy group, polyhaloalkyl, polyhaloalkoxy, alkoxycarbonyl, substituted amino group in which the permissible substituents are the same or different and one or two of the success ends are: propargyl, alkoxyalkyl, alkylthioalkyl, alkyl, alkenyl, haloalkenyl. or polyhaloalkenyl; Alkylthio, Polyhaloalkylthiogruppe, alkylsulfinyl, Polyhaloalkylsulfinyl, alkylsulfonyl, Polyhaloalkylsuifonyl, alkylsulfonylamino, Alkylkarbonylamino-, polyhaloalkyl sulfonjrlamino-, Polyhaloalkylkarbonylaminogruppe, trialkylsilyl, aryldialkylsilyl, triarylsilyl sulfonic acid and derivative salts, phosphonic acid and derivative salts, Älkoxykarbonylamino-, Alkylaminokarbonyloxy-, Dialkylaminokarbonyl oxy group, Alkenyl, polyhaloalkenyl, alkenyloxy group, alkynyl, alkynyloxy, polyhaloalkenyloxy group, polyhaloalkynyl, polyhaloalkynyloxy group, polyfluoroalkanol, Zjranoßlkylaminogruppe, semicarbazonomethyl, alkoxycarbonylhydrazonomethyl, alkoxyiniinomethyl, unsubstituted or substituted aryloxyiminomethyl, hydrazonomethyl, unsubstituted or substituted Arylhydrazonomethyl, one condensed with a mono-, di- or polysaccharide Hydroxy, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, aryloxy, aralkoxy, arylthio, aralkylthio, alkylthioalkyl, arylth ioalkyl, arylsulfinyl, arylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, HaIoalkenyloxy-, Haloalkynyloxy-, Haloalkynylthiogruppe, haloalkenyl sulfonyl, Polyhaloalkenylsulfonyl, alkoxysulfonyl, aryloxysulfonyl, propargyloxy, aroyl, Haloazyl, PoIyhaloazyl, Aryloxykarbonyl, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, arylaminosulfonyl, Karboxyalkoxy-, Karboxyalkylthio- , Alkoxycarbonylalkoxy, azyloxy, haloazyloxy, polyhaloazyloxy, aroyloxy, alkylsulfonyloxy, polyhaloacyloxy, alkenylsulfonyloxy, arylsulfonyloxy, haloalkylsulfonyloxy, polyhaloalkylsulfonyloxy, aroylamino, haloazylamino, alkoxycarbonyloxy, arylsulfonylamino, aminocarbonyloxy, cyanato , Isocyanato, Isothiozyano, Cycloalkylamino, trialkylammonium, arylamino, aryl (alkyl) amino, aralkylamino, Alkoxyalkylpho sphinyl, Alkoxyalkylphosphinothioyl, Allcylhydroxyphosphinyl, Dialkylaminoalkoxy-, Dialkoxyphosphino-, hydroxyamino, alkoxyamino, Aryloxyamino-, Aryloxyimino-, oxo - Thiono- , Alkylaminoalkoxy, alkoxyalkoxy group, Alkoxyalkenyl, cyanoalkoxy, dialkylsulfonium, -Χ, = X, -Χ = Ro5 ⁼ X-Roj -XR ₃ , -P-Y ₂ R ₄ , -Y ₄ - P- Y ₂ R ₄ Y ₃ R ₅ Y ₂ R ₄ γ ", the same or different and one or more of the following are: hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiozyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxy , Formamidino, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, nitro, cyano, hydroxycarbonyl and derived salts, lamidamido, alkyl, alkoxy, polyhaloalkyl, polyhaloalkoxy, Alkoxy carbonyl, substituted amino group in which the permissible substituents are the same or different and one or two of the following: propargyl, alkoxyalkyl, alkylthioalkyl, alkyl, alkenyl, haloalkenyl or polyhaloalkenyl; Alkylthio, polyhaloalkylthio group, alkylsulfinyl, polyhaloalkylsulfinyl, alkylsulfonyl, polyhaloalkylaulphonyl, alkylsulfonylamino, alkylcarbonylamino, polyhaloalkylsulfonylamino, polyhaloalkylcarbonylamino, irialkylsilyl, aryldialkylsilyl, triarylsilyl, sulfonic acid and derived salts, phosphonic acid and derived salts, alkoxycarbonylamino, alkylaminocarbonyl oxy, Dialkylaroinocarbonyloxy group, alkenyl, polyhaloalkenyl, alkenyloxy group, alkynyl, alkynyloxy, polyhaloalkenyloxy group, polyhaloalkynyl, polyhaloalkynyloxy group, polyfluoroalkanol, cyanoalkylamino group, semicarbazonomethyl, alkoxycarbonylhydrazonomethyl, alkpxyiminomethyl, unsubstituted or substituted aryloxyiminomethyl, hydrazonomettiyl, unsubstituted or substituted arylhydra onomethyl, one with a mono -, di- or polysaccharide condensed hydroxy group, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, aryloxy, aralkoxy, arylthio, aralkylthio, alkylthioalkyl, A rylthioalkyl, arylsulfinyl, arylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, haloalkenyloxy, haloalkynyloxy, haloalkynylthio group, haloalkenylsulfonyl, polyhaloalkenylsulfonyl, alkoxysulfonyl, aryloxysulfonyl, propargyloxy group, aroyl, haloazyl, polyhaloazyl, aryloxycarbonyl, amino-sulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, Arylaminosulfonyl, carboxyalkoxy, carboxyalkylthio, alkoxycarbonylalkoxy, azyloxy, haloazyloxy, polyhaloazyloxy, aroyloxy, alkylsulphonyloxy, alkenylsulphonyloxy, arylsulphonyloxy, haloalkylsulphonyloxy, polyhaloalkylsulphonyloxy, aroylamino, haloazylamino, alkoxycarbonyloxy, Aryl sulfonylamino, amino! Carbonyl oxy, cyanato, Isocyanato, isothiocyanato, cycloalkylamino, trialkylammonium, arylamino, aryl (alkyl) amino, aralkylamino, alkoxyalkylphosphinyl, alkoxyalkylphosphinothioyl, alkylhydroxyphosphinyl, dialkoxyphosphino, hydroxyamino, alkoxyamino, aryloxyamino, aryloxyimino, oxo, thiono, alkylaminoalkoxy , Dialkylaminoalkoxy, alkoxyalkoxy, alkoxyalkenyl, cyanoalkoxy, dialkylsulfonium, -X, = X, -X = R_, = X-R ,, -X-Ry - P - b ^R 5 in which X, R 1, R,
are defined ". , Y ₃ and Y. as in claim 41 68. The method according to claim 53, characterized in that the compound has the formula selected from: wherein: 66 ' 67 ' Y ' Y \ 69 · γ »γ» γ »γ» ^x 70 ' ^x 71' 72 ' ^x 73' and same or and Υ '™ one ^x 75 '76' ^x 77 ' ^x 78' ^x 79 and Y'g-v, Y'70 '^ * 73' ^x 76 """""79 or more of the following are hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkykenylthio, thiozyano, Propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy; aryldialkylsilyloxy, triarylsilyloxy, pormamidino, alkylsulfido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino, aminocarbonyl, alkylaminocarbonyl, dialkylamiriocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl , Keto, cyano group, hydroxy carbonyl and derived salts, pormamido group, alkyl, alkoxy group, polyhaloalkyl, polyhaloalkoxy group, alkoxy carbonyl, substituted amino group in which the permissible substituents are identical or different and one or two of the following: propargyl, alkoxyalkyl, alkylthioalkyl, Alkyl, alkenyl, haloalkenyl or polyhaloalkenyl; alkylthio, polyhaloalkylthio, alkyls ulfinyl, polyhaloalkylsulfinyl, alkylsulfonyl, polyhaloalkylsulfonyl, alkyl sulfonylamino, alkylcarbonylamino, polyhaloalkylsulfonylamino, polyhaloalkylcarbonylaroino, trialkylsilyl, aryldialkylsilyl, arylsilyl, sulphonic acid and derived salts, phosphonic acid and derived salts, alkoxycarbonylamino, alkylaminocarbonyloxy, dialkylaminocarbonyloxy, alkenyl, polyhaloalkenyl, alkenyloxy, alkynyl, alkynyloxy, polyhaloalkenyloxy, Polyhaloalkynyl, polyhaloalkynyloxy group, polyfluoroalkanol, cyanoalkylamino group, semicarbazonomethyl, alkoxycarbonylhydrazonomethyl, alkoxyiminomethyl, unsubstituted or substituted aryloxyiminomethyl, hydrazonomethyl, unsubstituted or substituted arylhydrazonomethyl, a mono-, di- or polysaccharide-fused hydroxy group, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, aryloxy-, Aralkoxy, arylthio, aralkylthio, alkylthioalkyl, arylthioalkyl, arylsulfinyl, arylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, haloalkenyloxy, haloalkynyloxy, haloalkynylthi haloalkenylsulfonyl, polyhaloalkenylsulfonyl, alkoxysulfonyl, aryloxysulfonyl, propargyloxy group, aroyl, haloazyl, polyhaloazyl, aryloxycarbonyl, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, arylaminosulfonyl, carboxyalkoxy, carboxyalkylthio, alkoxycarbonylalkoxy, acyloxy, haloazyloxy, polyhaloazyloxy, aroyloxy , Alkylsulfonyloxy, alkenylsulfonyloxy, arylsulfonyloxy, haloalkylsulfonyloxy, polyhaloalkylsulfonyloxy, aroylamino, haloazylarnino, alkoxycarbonyloxy, arylsulfonylamino, aminocarbonyloxy, cyanato, isothiozyano, isocyanato, cycloalkylamino, trialkylammonium, arylamino, aryl (alkyl) amino, aralkylamino, alkoxyalkylphosphinyl, alkoxyalkylphosphinothioyl, alkylhydroxyphosphinyl, dialkoxyphosphino, hydroxyamino, alkoxyamino, aryloxyaroino, aryloxyimino, oxo, thiono, alkylaminoalkoxy, dialkylaminoalkoxy, alkoxyalkoxy, alkoxyalkenyl, cyanoalkoxy, dialkylsulfonium, -Λ j = Λ. , A - Ii. Ί ^ -X - R ₃ , - P ^ Y ₂ R ₄ , -Y ₄ - P ^ Y ₂ R ₄ Y ₃ R ₅ ^Y 2 ^R 4 ^Y 3 ^R 5
r 'is a Voff of O or 1; A _'12 , A' ₁₃ , A » ₁₄ , A _'15 , A» ₁₆ and A' _1? as R., are defined in claim and X _'21, X' _22, X _'23, X' _24th X '
are defined. X _'26 as X in claim 41 wherein X, R ₃ , R ₄ , R ₅ , Y ₁ , Y ₂ , Y ₃ and Y _{4 are} as defined in claim 41. 69. The method according to claim 53, characterized in that the compound has the following formula: >
^Y 62 wherein: Y ', Y', Y ^ ₄ , Y ^ ₅ and R ^ are the same or different and are the following: hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, carboxyalkylcarbonylalkylthio, polyhaloalkenylthio, thiozyano, propargylthio, hydroxyindno , Alkoxyimino, trialkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxy, samaramidino, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino, aminocarboxy nyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, nitro, cyano, hydroxycarbonyl and derived salts, imidamamido, alkyl, alkoxy, polyhaloalkyl, polyhaloalkoxy, alkoxycarbonyl, substituted amino in which the permissible substituents are the same or different and one or two of the following are: propargyl, alkoxyalkyl, alkylthioalkyl, alkynyl, alkenyl, haloalkenyl or polyhaloalkenyl; Alkylthio, polyhaloalkylthio group, alkylsulfinyl, polyhaloalkylsulfinyl, alkylsulfo, nyl, polyhaloalkylsulfonyl, alkylsulfonylamino, alkylcarbonylamino, polyhaloalkylsulfonylaraino, polyhaloalkylcarbonylamino, trialkylsilyl, aryldialkylsilyl, triarylsilyl, sulfonic acid and derived salts, phosphonic acid and derived salts, alkoxycarbonyland.no-, alkylaminocarbonyloxy , Dialkylaminocarbonyloxy group, alkenyl, polyhaloalkenyl, alkenyloxy group, alkynyl, alkynyloxy, polyhaloalkenyloxy group, polyhaloalkynyl, polyhaloylkynyloxy group, polyfluoroalkanol, cyanoalkylamino group, semicarbazonomethyl, alkoxycarbonylhydrazonomethyl, alkoxyiminomethyl, unsubstituted or substituted aryloxyiminomethyl, hydrazonomethyl, unsubstituted or substituted arylhydrazonomethyl, one with a mono-, di- or polysaccharide fused hydroxy, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, aryloxy, aralkoxy, arylthio, aralkylthio, alkylthioalkyl, arylthioal alkyl, ArylBulfinyl, arylsulfonyl ^ haloalkylsulfinyl, haloalkyl sulfonyl, thio Haloalkenyloxy-, Haloalkynyloxy-, haloalkynyl, Haloalkenylsulfonyl, Polyhaloalkenylsulfonyl, Alkoxysulfonyl, aryloxysulphonyl, propargyloxy, aroyl, Haloazyl, Polyhaloazyl, Aryloxykarbonyl, Aminoaulfonyl, Alkylaminoaulfonyl, dialkylaminosulfonyl, arylaminosulfonyl, Karboxyalkoxy-, Karboxyalkylthio , Alkoxycarbonylalkoxy, azyloxy, haloazyl0x5 ', polyhaloazyloxy, aroyloxy, alkylsulfonyloxy, alkenylsulfonyloxy, arylsulfonyloxy, haloalkylsulfonyloxy, polyhaloalkylsulfonyloxy, aroylamino, haloazylamino, alynoxycarbonyloxy, arylulfonylamino, alniocarbonyloxy , Cyano-to, isocyanato, isothiocyanato, cycloalkylamino, trialkylammonium, arylamino, aryl (alkyl) amino, aralkylamino, alkoxyalkylphosphinyl, alkoxyalkylphosphinothioyl, alkylhydroxyphosphinyl, dialkoxyphosphino, hydroxyamino, alkoxyamino, aryloxyamino, aryloxyimino, Oxo, thiono, alkylaminoalkoxy, dialkylamine alkoxy, alkoxyalkoxy, alkoxyalkenyl, cyanoalkoxy, dialkylsulfonium, T "VΎ -"D - T-P "dft. j" - Λ. f "" Λ - XIn) - -Λ- 1V * j J Fri. P
\ Y ₂ R ₄ ; and -X - R ₃ , - P ^ - Y ₂ R ₄ , -Y ₄ - ^Y 3 ^E 5 X 'as defined in claim 41; wherein X, R ₃ , R ₄ , R ₅ , Y ₁ , Y ₂ , Y ₃ and Y _{4 are} as defined in claim 41. 70. The method according to claim 53, characterized in that the compound has a formula which is selected from: 90 R 'and Y'q ₀ are the same or different unary' ₁₈ is one or more of the following: hydrogen, halogen, Alkylkarbonyl, Alkoxykarbonylalkylthiogruppe, Alkylkarbonyl- alkyl, alkoxycarbonylalkyl, polyhaloalkenylthio, thiozyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, aryldialkylsilyloxy, triarylailyloxy, jormama-midino, alkylaulamido, dialkylsulfoylidido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxyl, amino group, Aminocarbonyl, alkylaminocarbonyl, bialkylaiainocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, nitro, cyano, hydroxycarbonyl and derived salts, formamido, alkyl, alkoxy, polyhaloalkyl, polyhaloalkoxy, alkoxycarbonyl, substituted amino in which the permissible substituents are the same or different and one or two of the following are: propargyl, alkoxyalkyl, alkylthioalkyl, alkyl, alkenyl, haloalkenyl or polyhaloalkenyl; Alkylthio, polyhaloalkylthio group, alkylsulfinyl, polyhaloalkylsulfinyl, alkylsulfonyl, polyhaloalkylsulfonyl, alkylsulfonylamino, alkylcarbonylamino, polyhaloalkylsulfonylamino, polyhaloalkylcarbonylamino, trialkylsilyl, aryldialkylsilyl, triarylsilyl, sulfonic acid and derived salts, phosphonic acid and derived salts, alkoxycarbonylamino, alkylaminocarbonyloxy, dialkylaminocarbonyloxy, alkenyl ; kenyl, polyhaloalkenyl, alkenyloxy group, alkynyl, alkynyloxy, polyhaloalkenyloxy group, polyhaloalkynyl, polyhaloalkynyloxy group, polyfluoroalkanol, cyanoalkylamino group, semicarbazonomethyl, alkoxycarbonylhydrazonomethyl, alkoxyiminomethyl, unsubstituted or substituted aryloxyiminomethyl, hydrazonomethyl, unsubstituted or substituted arylhydrazonomethyl, one with a mono-, di- or polysaccharide condensed hydroxy group, HaIoalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, aryloxy, aralkoxy, arylthio, aralkylthio, alkylthioalkyl, arylthioalkyl, arylsulfinyl, Aryl3ulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, Haloalkenyloxy-, Haloalkynyloxy-, Haloalkynylthiogruppe, Haloalkenylsulfonyl, Polyhaloalkenylsulfonyl, alkoxysulfonyl, aryloxysulfonyl , Propargyloxy group, aroyl, haloazyl, polyhaloazyl, aryloxylcarboxylate, amino sulfonyl, alkylaminosulfonyl, dialkylarninosulfonyl, arylaminosulfonyl, carboxyalkoxy, carboxyalkylthio, alicyloxycarbonylakoxy, azjr ioxy, haloazyloxy, polyhaloazyloxy, aroyloxy, alkylruloyl, alkenylsulfonyloxy,
Arylsulfonyloxy, Haloalkylaulfonyloxy, Polyhaloalkylsulfonyloxy, Aroylaiiiino, Haloazylamino, Alkoxykarbonyloxy, Arylsulfonylamino, Aminokarbonyl oxj-, cyanato,
Isocyanato, isothiocyanato, cycloalkylamino, irialkylanimoniuronic, aryl-amino, aryl (alkyl) amino, aralkylamino, alkoxyalkylphosphinyl, alkoxyalkylphosphinothioyl, alkylhydroxyphosphinyl, dialkoxyphosphino, hydroxyamino, alkoxyamino, aryloxyimino, aryloxyamino, oxo, thiono, alkylaminoalkoxy , Dialkylaminoalkoxy, alkoxyalkoxy, alkoxyalkenyl, cyanoalkoxy, dialkylsulfonium, -Z, = X, -X = R ₃ , = XR ₃ , -X - R ₃ , - P- Y ₂ R ₄ , -Y ₄ - P- ^Y 2 ^R 4 Y ₃ R ₅ AJg as R .. is defined in claim 41 and
XIg as X is defined in claim 41, wherein X, R ₃ , R ₄ , Rp, Y, Y ₂ , Y and Y ₄ as claimed in claim 41
are defined. 71. The method according to claim 53, characterized in that the compound has the following IOrmel: ^ζ ΐ wherein: R '^ g is defined as R.J in claim 1; X'og as X is defined in claim 1; Z'.j and Z ' _{2 are} independently 0, S, CL-Cg-alkylidene, substituted or unsubstituted benzylidene, WH or KR "', wherein R ¹ " is alkyl, aryl, aralkyl, alkenyl or alkynyl, and ^Y> 91 and ^Y> 92 inde-Sig alkyl, halo or "an Alkoxj ^r group from each other. 72. The method according to claim 53, characterized in that the compound has the following formula: wherein: R ⁵ _{20 is} as defined in claim 1 R ₁ ; X ' ₁ as X is defined in claim 1; Z'.j is 0, S, C.j-Cg-alkylidene, substituted or unsubstituted benzylidene, MH or HR "', wherein R"' is alkyl, aryl, aralkyl, alkenyl or alkynyl, and ^Y> 93 '^Y> 94 ^{and Y>} 95 are ^{each or} different and are hydrogen, halogen, alkylcarbonyl, alkylcarbonyloxyalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiozyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, Aryldialkylsilyloxy, triarylsilyloxy, imomamidino, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaniinothiocarbonyl, dialkylaminothiocarbonyl, khio, cyano, hydroxycarbonyl and derivative salts, pyramido, alkyl, alkoxy , Polyhaloalkyl, polyhaloalkoxy group, alkoxycarbonyl, substituted amino group in which the permissible substituents are the same or different and one or two of the following: propargyl, alkoxyalkyl, alkylthioalkyl, alkyl, alkenyl, haloalkenyl or polyhaloalkenyl; Alkylthio, polyhaloalkylthio group, alkylsulfinyl, polyhaloalkyl, quifinyl, alkylsulfonyl, polyhaloalkylsulfonyl, alkylsulfonylamino, alkylcarbonylamino, polyhaloalkylsulfonylamino, polyhaloalkylcarbonylamino, trialkylsilyl, aryldialkyrileilyl, triarylsilibryl, sulfonic acid and derived salts, phosphonic acid and derived salts, alkoxycarbonylamino, alkylaminocarbonyloxy , Dialkylaminocarbonyloxy group, alkenyl, polyhaloalkenyl, alkenyloxy group, alkynyl, alkynyloxy, polyhaloalkenyloxy group, polyhaloalkynyl, polyhaloalkynyloxy group, polyfluoroalkanol, cyanoalkjetramino group, semicarbazonomethyl, alkoxycarbonylhydrazonomethyl, ¹ alkoxyiminomethyl, unsubstituted or substituted aryloxyiminomethyl, hydrazonomethyl, unsubstituted or substituted arylhydrazonomethyl, one with a mono-, di- or polysaccharide condensed hydroxy group, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, aryloxy, aralkoxy, arylthio, aralkylthio, alkylthioalkyl, arylth ioalkyl, arylsulfinyl, arylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, · Haloalkenyloxy-, Plaloalkynyloxy-, haloalkynyl thio group, Haloalkenylsulfonyl, Polyhaloalkenylsulfonyl, Alkoxysulfonyl, aryloxysulphonyl, propargyloxy, aroyl, Haloazyl, Polyhaloazyl, Aryloxykarbonyl, aminosulfonyl, alkylaminosulfonyl, dialkyl amino sulfonyl, Arylainino sulfonyl, Karboxyalkoxy , Carboxyalkylthio, alkoxycarbonylalkoxy ', azyloxy, haloazyloxy, polj'haloazyloxy, aroyloxy, alkylsulphonyloxy, alkenylsulphonyloxy, arylsulphonyloxy, haloalkylsulphonyloxy, polyhaloalkylsulphonyloxy, aroylamino, haloazylamino, alkoxycarbonyloxy, arylsulphonylamino, Aminocarbonyloxy, cyanato, isocyanato, isothiocyanato, cycloalkylaraino, trialkylammonium, aryl-amino, aryl (alkyl) amino, aralkyl-ino, alkoxyalkylphosphinyl, .alkoxyalkyl, phosphinethioyl, alkyldiamydroxyphosphinyl, dialkylaminioalkoxy, dialkoxyphosphino, hydroxyanino, alkoxyamino, aryloxyamino, aryloxyimino, oxo, thiono, alkylaroinoallcoxy, alkoxyalkoxy, allcoxyalkenyl, cyanoalkoxy, dialkylsulfonium, -X, = X, -X = R o, - X-R Q, -X-R ₃ , -P-Y ₂ R ₄ , -Y ₄ -p-Y ₂ R ₄ i are Y ₃ R ₅ . wherein X, R ₃ , R ₄ , R ₅ , Y 1, Y ₂ , Y ₃ and Y _{4 are} as defined in claim 1. 73. Method according to claim 53, characterized in that the connection has the following formula: R '. ₂₁ -X _'32 -N
0 ' '96 Y97  98 wherein: R ' ₂ -] is as defined in claim 1 R ₁ ; X ', ._ as X is defined in claim 1 and Y'g, Υ'ηγ »Y'g3 ^{un (i)} '99 are the same or different and are hydrogen, halogen, alkyl or an alkoxy group. 74. A method according to claim 53, characterized in that the compound has the formula: X ₃₃ O ₂ C Cl wherein: R _{'22 is} as R .. defined in claim 1 and X'_ ₃ and Z ', independently of one another, are hydrogen, halogen, a hydroxy group, alkyl, alkoxy group, alkylcarbonyl or alkoxycarbonyl. Process according to claim 53, characterized in that the compound has the following formula: Cl 76. The method according to claim 53, characterized in that the compound has the following formula: Cl 77. The method according to claim 53, characterized in that the compound has the following formula: Cl 78. The method according to claim 53i, characterized in that the compound has the following formula: Cl Cl 79 «Method according to claim 53, characterized in that the compound has the following formula: Cl 80. The method according to Atispruch 53, characterized in that the compound has the following formula: Cl Cl 81. The method according to claim 53, characterized in that the compound has the following formula: 82. The method according to claim 53, characterized in that the compound has the following formula: 83. The method according to claim 53, characterized in that the compound has the following formula: 84. A method according to claim 53, characterized in that the compound has the formula: Cl OO Process according to claim 53, characterized in that the compound has the following formula: Cl H - < Cl 86. The method according to claim 53 »characterized in that the compound has the following formula: > Y ^C1   MI-K || ^ ⁰¹ A method according to claim 53, characterized in that the connection has the following formula: 0 MH-N OCH ₃ 0 88. The method according to claim 53 »characterized in that the compound has the following formula: ! JH-N ' 89. The method according to claim 53, characterized in that the compound has the following formula: 90. The method according to claim 53 »characterized in that the compound has the following formula: 91. The method according to claim 53, characterized in that the compound has the following formula: Cl 92. The method according to claim 53 »characterized in that the compound has the following formula: br A method for increasing the crop yield, characterized by the application of an effective, sufficient for the increase of crop yield, the photosynthetic Klektronentranaport the plant substantially but not interfering amount of the compound according to claim 41 on the crop. A method according to claim 53, characterized in that the compound is applied to the crop in an amount sufficient to increase crop yield without causing substantial inhibition of the photosynthetic light responses of the plant. Process according to claim 53, characterized in that the compound is applied to the crop under the conditions in which the plant has substantially no water stress. 96. A method according to claim 53, characterized in that the compound is applied to the crop in a period of time prior to the reproductive growth phase of the plant. - A method according to claim 53, characterized in that the compound is applied to the crop in a period of time prior to significant soil moisture loss. 98. The method of claim 53 »characterized in that the compound is applied to the crop in a period of time during the reproductive growth phase of the plant. 99. The method according to claim 53, characterized in that the compound on the crop in a concentration between about 0.045 - 45.359 kg ie 4047 m is applied. 100. The method according to claim 53, characterized in that the compound on the crop in a concentration between about 0.113-6.804 kg of the compound per 4047 m is applied. 101. The method according to claim 53, characterized in that the plant is an agricultural or horticultural crop. 102. The method of claim 53, characterized in that the plant is selected from corn, cotton, sweet potatoes, white potatoes, alfalfa, wheat, rye, highland rice, barley, oats, sorghum, dried beans, Segabohnen, sugar beets, sunflowers, tobacco, tomatoes , Canola, deciduous fruits, citrus fruits, tea, coffee, olives, pineapple, cocoa, bananas, sugarcane and oil palms. 103. The method according to claim 53, characterized in that 'the plant is transplanted plant material. 104. The method according to claim 103, characterized in that the transplanted plant is selected from tobacco, tomatoes, egg plants, cucumbers, lettuce, strawberries, perennial border plants, wood shrubs and tree seedlings. A composition for reducing the moisture loss of plants, characterized by an acceptable carrier and an effective amount of a compound according to claim 41 which is sufficient to reduce plant moisture loss and which does not substantially inhibit the photosynthetic electron transport of the plants. 106. A composition for increasing crop yields, characterized by an acceptable carrier and an effective, sufficient to increase crop yields, the photosynthetic electron transport of plants not substantially inhibiting amount of a compound according to claim 41 ♦ 107. Process according to
the connection
biologically 108. Method according to
the connection
biologically Claim 1, characterized in that in combination with one or more other active compounds is used. Claim 53, characterized in that in combination with one or more other active compounds is used. Process for reducing the moisture loss of soil in which plants or crops have been planted, characterized in that an effective amount of a compound which is not substantially inhibiting the photosynthetic electron transport of the plant is present on the plant surface or the fruit in an effective manner to reduce soil moisture loss is applied with the following formula ^D - ^T - H ₂ R ₁ -X- in which X and R "are as defined in claim 1.