Amidrazones and their use as insecticidal and acaricidal agents

Abstract

There are provided substituted acid amide, arylhydrazone compounds (amaidrazones) of formula I ##STR1## the use thereof for the control of insect and acarid pests and methods and compositions for the protection of crops from the damage and loss caused by said pests.

Description

BACKGROUND OF THE INVENTION

Certain insect and acarid pests are harmful and cause enormous losses annually in agricultural crops, stored products and human and animal health. It is an object of this invention to provide substituted acid amide, N-arylhydrazone compounds (amaidrazones) which are effective agents for the control of pestiferous insects and acarina.

It is another object of this invention to provide a method for the protection of important agronomic crops from-the harmful and damaging effects caused by insect and acarid pests.

It is a further object of this invention to provide insecticidal and acaricidal compositions.

SUMMARY OF THE INVENTION

The present invention provides a method for the control of insects or acarina which comprises contacting said insects or acarina or their food supply, breeding ground or habitat with an insecticidally effective amount of an amidrazone compound of formula I ##STR2## wherein A is C--R.sub.4 or N;

B is C--R.sub.5 or N; W is C--R.sub.6 or N with the proviso that one of A, B or W must be other than N; Y is hydrogen, halogen, CN, NO.sub.2, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.1 -C.sub.6 alkoxy or C.sub.1 -C.sub.6 halo-alkoxy; n is an integer of 0, 1 or 2; R is hydrogen, C.sub.1 -C.sub.10 alkyl optionally substituted with one or more halogens, C.sub.3 -C.sub.6 cycloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, (C.sub.1 -C.sub.4 alkyl)SO.sub.x, (C.sub.1 -C.sub.4 haloalkyl)SO.sub.x, phenyl optionally substituted with one to three halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, (C.sub.1 -C.sub.4 alkyl)SO.sub.x, (C.sub.1 -C.sub.4 haloalkyl)SO.sub.x, NO.sub.2 or CN groups, or phenoxy optionally substituted with one to three halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, (C.sub.1 -C.sub.4 alkyl)SO.sub.x, (C.sub.1 -C.sub.4 -haloalkayl) SO.sub.x, NO.sub.2 or CN groups, C.sub.3 -C.sub.12 cycloalakyl optionally substituted with one or more halogens, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, (C.sub.1 -C.sub.4 alkyl)SO.sub.x, (C.sub.1 -C.sub.4 haloalkyl)SO.sub.x, phenyl optionally substituted with one to three halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, NO.sub.2 or CN groups, or phenoxy optionally substituted with one to three halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalky, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, NO.sub.2 or CN groups, or phenyl optionally substituted with one or more halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, NO.sub.2 or CN groups; R.sub.1 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sub.2 and R.sub.3 are each independently hydrogen, C.sub.1 -C.sub.10 alkyl optionally substituted with one or more halogen, hydroxy, C.sub.1 -C.sub.4 alkoxy, (C.sub.1 -C.sub.4 alkyl)SO.sub.x, CONR.sub.7 R.sub.8, CO.sub.2 R.sub.9, R.sub.10, R.sub.11, C.sub.3 -C.sub.6 cycloalkyl optionally substituted with one to three halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 haloalkoxy, NO.sub.2 or CN groups, phenyl optionally substituted with one or more halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkayl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, CO.sub.2 or CN groups, or pyridyl optionally substituted with one or more halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, NO.sub.2 or CN groups, C.sub.3 -C.sub.10 alkenyl optionally substituted with one or more halogen, hydroxy, C.sub.1 -C.sub.4 -alkoxy, (C.sub.1 -C.sub.4 alkyl)SO.sub.x, CONR.sub.7 R.sub.8, CO.sub.2 R.sub.9, R.sub.10, R.sub.11, C.sub.3 -C.sub.6 cycloalkyl optionally substituted with one to three halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 halo-alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalakoxy, NO.sub.2 or CN groups, phenyl optionally substituted with one or more halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, CO.sub.2 or CN groups, or pyridyl optionally substituted with one or more halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, NO.sub.2 or CN groups, C.sub.3 -C.sub.10 alkynyl optionally substituted with one or more halogen, hydroxy, C.sub.1 -C.sub.4 -alkoxy, (C.sub.1 -C.sub.4 alkyl)SO.sub.x, CONR.sub.7 R.sub.8, CO.sub.2 R.sub.9, R.sub.10, R.sub.11, C.sub.3 -C.sub.6 cycloalkyl optionally substituted with one to three halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 halo-alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, NO.sub.2 or CN groups, phenyl optionally substituted with one or more halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, CO.sub.2 or CN groups, or pyridyl optionally substituted with one or more halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, NO.sub.2 or CN groups, C.sub.3 -C.sub.12 cycloalkyl optionally substituted with one or more halogen, hydroxy, C.sub.1 -C.sub.4 -alkoxy, (C.sub.1 -C.sub.4 alkyl)SO.sub.x, CONR.sub.7 R.sub.8, CO.sub.2 R.sub.9, R.sub.10, R.sub.11, C.sub.3 -C.sub.6 cycloalkyl optionally substituted with one to three halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, NO.sub.2 or CN groups, phenyl optionally substituted with one or more halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 -haloakoxy, CO.sub.2 or CN groups, or pyridyl optionally substituted with one or more halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, NO.sub.2 or CN groups or R.sub.2 and R.sub.3 may be taken together to form a ring represented by the structure ##STR3## R.sub.4, R.sub.5 and R.sub.6 are each independently hydrogen, halogen, CN, NO.sub.2, (C.sub.1 -C.sub.4 alkyl )SO.sub.x, (C.sub.1 -C.sub.4 -haloalkyl) SO.sub.x, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.1 -C.sub.6 alkoxy or C.sub.1 -C.sub.6 haloalkoxy, R.sub.7, R.sub.8 and R.sub.9 are each independently hydrogen or C.sub.1 -C.sub.4 alkyl; R.sub.10 is NR.sub.12 R.sub.13, ##STR4## R.sub.11 is ##STR5## R.sub.12, R.sub.13, R.sub.14 and R.sub.15 are each independently hydrogen or C.sub.1 -C.sub.4 alkyl; X is O, S or NR.sub.14 ; r is an integer of 0 or 1; p and m are each independently an integer of 0, 1, 2 or 3 with the provisos that only one of p, m or r can be 0 and that the sum of p+m+r must be 4, 5 or 6; x is an integer of 0, 1 or 2; or the acid addition salts thereof.

The present invention further provides N-arylamidrazone compounds of formula I wherein A, B, W, Y, n, R, R.sub.1, R.sub.2, and R.sub.3 are as described hereinabove with the proviso that when all of A, B and W are other than N, then R and one of R.sub.2 or R.sub.3 must be other than hydrogen and with the further proviso that when one of A, B or W is N, then Y, R.sub.4, R.sub.5 or R.sub.6 must be other than C.sub.1 -C.sub.10 alkyl.

Compositions and methods for the protection of growing plants from attack and infestation by insects and acarina are also provided.

DETAILED DESCRIPTION OF THE INVENTION

A variety of insects and acarina cause great economic loss by damaging or destroying agricultural crops and other valuable plants; by aiding in the spread and development of bacteria, fungi and viruses that produce diseases of plants; and by destroying or lowering the value of stored foods, other products and possessions. Insects and acarina present some of the farmers' greatest problems the world over. The need for alternative and effective insect and acarid control is a global concern.

It has now been found that the substituted acid amide, N-arylhydrazone compounds of formula I are especially efficacious insecticidal and acaricidal agents, particularly against Coleoptera, Lepidoptera and Acarina.

The formula I amidrazone compounds of the present invention have the structural formula ##STR6## wherein A, B, W, Y, n, R, R.sub.1, R.sub.2 and R.sub.3 are described hereinabove. The term halogen as used in the specification and claims designates chlorine, fluorine, bromine or iodine. The term acid addition salts designates those salts formed by acids commonly known in the art such as hydrogen chloride, hydrogen bromide, hydrogen bisulfate, hemi-hydrogen sulfate and the like. In the above definition when n is O then Y is hydrogen.

Preferred compounds of the invention are those wherein R, R.sub.2 and R.sub.3 are each independently hydrogen or C.sub.1 -C.sub.6 alkyl, A is C--R.sub.4, B is C--R.sub.5, W is C--R.sub.6, Y is halogen and n is 1. Particularly preferred compounds are those wherein R.sub.1 is hydrogen, R.sub.4 is halogen, R.sub.5 is hydrogen and/or R.sub.6 is C.sub.1 -C.sub.6 alkyl substituted with one or more halogens, preferably trifluoromethyl.

Other preferred compounds of the invention are compounds having the structure ##STR7## wherein R is C.sub.1 -C.sub.10 alkyl;

R.sub.1 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sub.2 is C.sub.1 -C.sub.10 alkyl; R.sub.3 is hydrogen or C.sub.1 -C.sub.10 alkyl; and R.sub.4, R.sub.6 and Y are each independently hydrogen, halogen, CN, NO.sub.2, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.1 -C.sub.6 alkoxy, or C.sub.1 -C.sub.6 haloalkoxy.

The N-arylamidrazones of formula I may be prepared by reacting an acid chlorides hydrazone (hydrazinoyl chloride) of formula II with an amine compound, HNR.sub.2 R.sub.3, as shown in flow diagram I, ##STR8##

Compounds of formula II may be prepared by reacting a suitable arylhydrazine of formula III with the appropriate acid chloride, RCOC1, to obtain an N-arylhydrazide of formula IV and reacting the formula IV hydrazide with a chlorinating agent such as thionyl chloride to give the desired formula II N-arylhdrozinoyl chloride product. The reaction is illustrated in flow diagram II. ##STR9##

The substituted N-arylamidrazone compounds of the present invention are effective for controlling insect and acarid pests. Said compounds are also effective for protecting growing or harvested crops from attack and infestation by such pests.

In practice, generally about 10 ppm to 10,000 ppm, preferably about 100 to 5,000 ppm of the formula I compound dispersed in a liquid carrier, when applied to the plants or the soil or water in which they are growing, is effective to protect the plants from insect and acarina attack and infestation. Soil application of the formula I compounds is particularly effective for the control of the post-embryonic development stages of Coleoptera and Diptera. Applications, such as spray applications, of compositions of the invention are generally effective at rates which provide about 0.125 kg/ha to about 250 kg/ha, preferably about 10 kg/ha to 100 kg/ha. Of course, it is contemplated that higher or lower rates of application of the N-aryl-amidrazone compounds may be used dependent upon the prevailing environmental circumstances such as population density, degree of infestation, stage of plant growth, soil conditions, weather conditions and the like.

Advantageously, the compounds of the invention may be used in conjunction with, or in combination with other biological and chemical control agents including other insecticides, nematicides, acaricides, molluscicides, fungicides and bactericides such as nuclear polyhedrosis viruses, pyrroles, arylpyrroles, halobenzoylureas, pyrethroids, carbemates, phosphates, and the like.

Typical formulations suitable for the formula I compounds of the invention are granular compositions, flowable compositions, wettable powders, dusts, micro-emulsions, emulsifiable concentrates and the like. All compositions which lend themselves to soil, water and foliage application and provide effective plant protection are suitable. Compositions of the invention include the formula I N-arylamidrazone amide compound admixed with an inert solid or liquid carrier.

Where compositions of the invention are to be employed in combination treatments with other biological or chemical agents, the composition may be applied as an admixture of the components or may be applied sequentially.

For a more clear understanding of the invention, specific examples thereof are set forth below. These examples are merely illustrative, and are not to be understood as limiting the scope and underlying principles of the invention in any way.

EXAMPLE 1

Preparation of 2,2-Dimethylpropionic acid,2-(2,6- dichloro-.alpha.,.alpha.,.alpha.-trifluoro-p-tolyl)hydrazide ##STR10##

A solution of 2,6-dichloro-4-(trifluoro-methyl)phenylhydrazine (50.0 g, 0.20 mol) in methylene chloride is treated dropwise with trimethylacetyl chloride (30.6 g, 0.254 mol), stirred for 30 minutes, treated with 10% aqueous NaOH and stirred for 3 hours. The phases are separated; the organic phase is washed with water, dried over MgSO.sub.4 and concentrated in vacuo to give an off-white solid residue. The solid is recrystallized from 1,2-dichloroethane to give the title product as a white solid, 55 g (82% yield), mp 140.degree.-141.degree., identified by .sup.1 HNMR, .sup.13 CNMR and IR spectral analyses.

EXAMPLES 2-42

Preparation of substituted N-arylhydrazide derivatives ##STR11##

Using essentially the same procedure described above for Example 1 and substituting the appropriate aryl-hydrazine and acid chloride, the compounds shown in

TABLE I__________________________________________________________________________ ##STR12##ExampleNumber A B W Yn R mp .degree.C.__________________________________________________________________________ 2 CCl CH CCF.sub.3 6-Cl (CH.sub.3).sub.2 CHCH.sub.2 135-136 3 CCl CH CCl 6-Cl (CH.sub.3).sub.3 C 124-125.5 4 CCl CH CH 6-Cl (CH.sub.3).sub.3 C 114-115 5 CBr CH CCF.sub.3 6-Br (CH.sub.3).sub.3 C 118-120 6 CBr CH CCF.sub.3 6-Br CH.sub.3 173-175 7 CBr CH CCF.sub.3 6-Br C.sub.6 H.sub.5 181-184 8 CCH.sub.3 CH CCl H (CH.sub.3).sub.3 C 103-106 9 CCl CH CCF.sub.3 6-Cl (CH.sub.3).sub.3 CCH.sub.2 125-12710 CCl CH CCl 6-Cl pClC.sub.6 H.sub.5 188-19011 CCl CH CCF.sub.3 6-Cl (CH.sub.3).sub.2 CH 158-15912 CCl CH CCl 6-Cl cylopropyl 186-18813 CCl CH CCF.sub.3 6-Cl CH.sub.3 CH.sub.2 C(CH.sub.3).sub.2 121-12314 CH CH CCF.sub.3 H (CH.sub.3).sub.3 C 136-13915 CCl CH CCF.sub.3 H (CH.sub.3).sub.3 C 143-14516 CCl CH CCF.sub.3 6-Cl ##STR13## 125-12717 CCl CCl CCl 5,6-diCl (CH.sub.3).sub.3 C18 N CH CCF.sub.3 6-Cl (CH.sub.3).sub.3 C 151-151.519 CCl CH CCl 6-Cl ##STR14## 138-14020 CCl CH CCF.sub.3 6-Cl pClC.sub.6 H.sub.5 OC(CH.sub.3).sub.2 137-13921 CCF.sub.3 CH CH H (CH.sub.3).sub.3 C 98-10022 CCl CH CCF.sub.3 6-Cl ##STR15## 101-10323 CCl CH CCl 6-Cl cyclohexyl 188-18924 CCl CH CCF.sub.3 6-Cl C.sub.6 H.sub.5 C(CH.sub.3).sub.2 104-10525 CCl CH CCl 6-Cl CF.sub.3 CF.sub.2 131-13226 CCl CH CCl 6-Cl (CH.sub.3).sub.2 CH 164-16527 CCl CH CCF.sub.3 6-Cl cyclopropyl 172-17428 CCl CH CCl 6-Cl CH.sub.3 CH.sub.2 C(CH.sub.3).sub.2 132-13429 CCl CH CCF.sub.3 6-Cl ##STR16## 160-16230 CBr CH CCF.sub.3 6-Br (CH.sub.3).sub.3 C 140-14131 CCl CH CCl 6-Cl CH.sub.3 (CH.sub.2).sub.5 C(CH.sub.3).sub.232 N N CCl H (CH.sub.3).sub.3 C 178-18233 CCl CH CCF.sub.3 6-Cl ##STR17## 121-12334 CCl CH CCF.sub.3 6-Cl pClC.sub.6 H.sub.5 C(CH.sub.3).sub.2 105-10735 CCl CH CCF.sub.3 6-Cl ClCH.sub.2 C(CH.sub.3).sub.2 119-12036 CCl CH CCF.sub.3 6-Cl ##STR18## 174-17537 CCl CH CCl 6-Cl ClCH.sub.2 C(CH.sub.3).sub.2 124-12538 CCl CH CH 5-CF.sub.3 (CH.sub.3).sub.3 C 170-177.539 CCl CH CCF.sub.3 6-Cl 1-methylcyclohexyl 105-10740 CH CCF.sub.3 CH H (CH.sub.3).sub.3 C 158-16041 CF CF CF 5,6-diF (CH.sub.3).sub.3 C 154-15742 CBr CH F 6-Br (CH.sub.3).sub.3 C 118-120__________________________________________________________________________

EXAMPLE 43

Preparation of 1-chloro-2,2-dimethylpropionaldehyde, 2-(2, 6-Dichloro-.alpha.,.alpha.,.alpha.-trifluoro-p-tolyl)hydrazone ##STR19##

A mixture of 2,2-dimethyl-2-(2,6-dichloro-.alpha.,.alpha.,.alpha.-trifluoro-p-tolyl)hydrazide propionic acid (50.0 g 0.152 mol) and thionyl chloride (53.8 g, 0,452 mol) in toluene is heated at reflux temperature for 8 hours, cooled to room temperature and concentrated in vacuo to give an oil residue. The oil is dissolved in hexanes and passed through a silica gel filtercake. The filter-cake is washed with several portions of hexanes. The filtrates are combined and concentrated in vacuo to give the title product as a yellow oil, 47.2 g (90% yield), identified by .sup.1 HNMR, .sup.13 CNMR and IR spectral analyses.

EXAMPLES 44-84

Preparation of substituted N-arylhydrazinoyl chlorides ##STR20##

Using essentially the same procedure as described above in Example 43 and substituting the appropriate hydrazide substrate, the compounds shown in Table II are prepared and identified by .sup.1 HMR, .sup.13 CNMR and IR spectral analyses.

TABLE II__________________________________________________________________________ ##STR21##ExampleNumber A B W Yn R mp .degree.C.__________________________________________________________________________44 CCl CH CCF 6-Cl (CH.sub.3).sub.2 CHCH.sub.245 CCl CH CCl 6-Cl (CH.sub.3).sub.3 C 44.5-45.546 CCl CH CH 6-Cl (CH.sub.3).sub.3 C47 CBr CH CF 6-Br (CH.sub.3).sub.3 C48 CBr CH CCF.sub.3 6-Br CH.sub.349 CBr CH CCF.sub.3 6-Br C.sub.6 H.sub.550 CCH.sub.3 CH CCl H (CH.sub.3).sub.3 C51 CCl CH CCF.sub.3 6-Cl (CH.sub.3).sub.3 CCH.sub.252 CCl CH CCl 6-Cl pClC.sub.6 H.sub.5 12053 CCl CH CCF.sub.3 6-Cl (CH.sub.3).sub.2 CH54 CCl CH CCl 6-Cl cyclopropyl55 CCl CH CCF.sub.3 6-Cl CH.sub.3 CH.sub.2 C(CH.sub.3).sub.256 CH CH CCF.sub.3 H (CH.sub.3).sub.3 C57 CCl CH CCF.sub.3 H (CH.sub.3).sub.3 C58 CCl CH CCF.sub.3 6-Cl ##STR22##59 CCl CCl CCl 5,6-diCl (CH.sub.3).sub.3 C60 N CH CCF.sub.3 6-Cl (CH.sub.3).sub.3 C61 CCl CH CCl 6-Cl ##STR23##62 CCl CH CCF.sub.3 6-Cl pClC.sub.6 H.sub.5 OC(CH.sub.3).sub.263 CCF.sub.3 CH CH H (CH.sub.3).sub.3 C64 CCl CH CCF.sub.3 6-Cl ##STR24##65 CCl CCH CCl 6-Cl cyclohexyl66 CCl CCH CCF.sub.3 6-Cl C.sub.6 H.sub.5 C(CH.sub.3).sub.267 CCl CH CCl 6-Cl CF.sub.3 CF.sub.268 CCl CH CCl 6-Cl (CH.sub.3).sub.2 CH69 CCl CH CCF.sub.3 6-Cl cyclopropyl70 CCl CH CCl 6-Cl CH.sub.3 CH.sub.2 C(CH.sub.3).sub.271 CCl CH CCF.sub.3 6-Cl ##STR25## 110-11172 CBr CH CCF.sub.3 6-Br (CH.sub.3).sub.3 C73 CCl CH CCl 6-Cl CH.sub.3 (CH.sub.2).sub.5 C(CH.sub.3).sub.274 N N CCl H (CH.sub.3).sub.3 C75 CCl CH CCF.sub.3 6-Cl ##STR26##76 CCl CH CCF.sub.3 6-Cl pClC.sub.6 H.sub.5 C(CH.sub.3).sub.2 85-8877 CCl CH CCF.sub.3 6-Cl ClCH.sub.2 C(CH.sub.3).sub.278 CCl CH CCF.sub.3 6-Cl ##STR27## 71-7379 CCl CH CCl 6-Cl ClCH.sub.2 C(CH.sub.3).sub.280 CCl CH CH 5-CF.sub.3 (CH.sub.3).sub.3 C81 CCl CH CCF.sub.3 6-Cl 1-methylcyclohexyl82 CH CCF.sub.3 CH H (CH.sub.3).sub.3 C83 CH CH CH 5-F (CH.sub.3).sub.3 C84 CBr CH F 6-Br (CH.sub.3).sub.3 C__________________________________________________________________________

EXAMPLE 85

Preparation of N-Ethyl-2,2-dimethylpropionamide, 2-(2,6- Dichloro-.alpha.,.alpha.,.alpha.-trifluoro-p-tolylhydrazone ##STR28##

A solution of (2,6-dichloro-.alpha.,.alpha.,.alpha.-trifluoro-p-tolyl)hydrazone 1-chloro-2,2-dimethylpropionaldehyde (20.0 g, 0.0575 mol) in tetrahydrofuran is treated dropwise with 70% aqueous ethylamine (28.0 g, 0.144 mol) at room temperature, stirred for 1 hour and concentrated in vacuo to give a semi-solid residue. The semi-solid is dispersed in ether and water. The phases are separated; the organic phase is washed with water, dried over MgSO.sub.4 and concentrated in vacuo to give the title product as a yellow oil, 19.8 g (97% yield), identified by .sup.1 HNMR, .sup.13 CNMR and IR spectral analyses.

EXAMPLES 86-169

Preparation of substituted N-arylamidrazones ##STR29##

Using essentially the same procedure described above in Example 85 and substituting the appropriate hydrazinoylchloride and a suitable amine, the compounds shown in Table III are prepared and identified by .sup.1 HNMR, .sup.13 CNMR and IR spectral analyses.

Hydrochloride salts of the invention may be prepared in accordance with the procedure outlined below.

EXAMPLE 146

Preparation of N-Ethyl-2,2-dimethyl-proprionamide, 2-(2,6-dichloro-.alpha.,.alpha.,.alpha.-trifluoro-p-tolylhydrazone hydrochloride ##STR30##

A stirred mixture of N-ethyl-2,2-dimethylpropionamide, 2-(2,6-dichloro-.alpha.,.alpha.,.alpha.-trifluoro-p-tolylhydrazone (0.1 g, 2.8 mmol) and hexane is bubbled through with HCl gas for a 30 minute period. The resultant reaction mixture is filtered to give the title compound as a white solid, 1.13 g, mp 202.degree.-202.5.degree.0 C.

TABLE III__________________________________________________________________________ ##STR31##ExampleNumber A B W Yn R R2 R3 mp .degree.C.__________________________________________________________________________ 86 CCl CH CCF.sub.3 6-Cl (CH.sub.3).sub.3 C pClC.sub.6 H.sub.5 H 87 CCl CH CCl 6-Cl (CH.sub.3).sub.3 CH.sub.3 CH.sub.2 CH.sub.2 H 88 CCl CH CCl 6-Cl (CH.sub.3).sub.2 CH CH.sub.3 CH.sub.2 CH.sub.2 H 48-50 89 CCl CH CCF.sub.3 6-Cl (CH.sub.3).sub.3 CCH.sub.2 CH.sub.3 CH.sub.2 CH.sub.2 H 90 CCl CH CCl 6-Cl (CH.sub.3).sub.2 CH cyclopropyl H 91 CCl CH CCF.sub.3 6-Cl (CH.sub.3).sub.3 CCH.sub.2 CH.sub.3 CH.sub.2 H 92 CCl CH CCF.sub.3 6-Cl (CH.sub.3).sub.2 CH CH.sub.3 CH.sub.2 H 62-64 93 CCl CH CCF.sub.3 6-Cl (CH.sub.3).sub.3 C CF.sub.3 CH.sub.3 H 94 CBr CH CCF.sub.3 6-Br (CH.sub.3).sub.3 C CH.sub.3 CH.sub.2 H 95 CBr CH CCF.sub.3 6-Br (CH.sub.3).sub.3 C CH.sub.3 CH.sub.2 CH.sub.2 H 96 CBr CH CCF.sub.3 6-Br (CH.sub.3).sub.3 C C.sub.6 H.sub.5 CH.sub.2 H 97 CBr CH CCF.sub.3 6-Br (CH.sub.3).sub.3 C furfuryl H 98 CBr CH CCF.sub.3 6-Br CH.sub.3 CH.sub.3 CH.sub.2 H 99 CBr CH CCF.sub.3 6-Br C.sub.6 H.sub.5 CH.sub.3 CH.sub.2 H100 CCl CH CCl 6-Cl (CH.sub.3).sub.3 C H H 131-135101 CCl CH CCl 6-Cl (CH.sub.3).sub.3 C CH.sub.3 CH.sub.3 61-63102 CCl CH CCl 6-Cl (CH.sub.3).sub.3 C CH.sub.3 CH.sub.2 H103 CCl CH CCF.sub.3 H (CH.sub.3).sub.3 C CH.sub.3 CH.sub.2 CH.sub.2 H104 CCl CH CH 6-Cl (CH.sub.3).sub.3 C CH.sub.3 CH.sub.2 CH.sub.2 H105 CCl CH CCF.sub.3 6-Cl (CH.sub.3).sub.3 C H H 100-102.5106 CCl CH CCF.sub.3 6-Cl (CH.sub.3).sub.3 C CH.sub.3 H 78-79.5107 CCl CH CCF.sub.3 6-Cl (CH.sub.3).sub.3 C CH.sub.3 CH.sub.3108 CCl CH CCF.sub.3 6-Cl (CH.sub.3).sub.3 C CH.sub.3 CH.sub.2 CH.sub.2 H109 CCl CH CCF.sub.3 6-Cl (CH.sub.3).sub.3 C (CH.sub.3).sub.3 C H 67.5-68.5110 CCl CH CCF.sub.3 6-Cl (CH.sub.3).sub.3 C (CH.sub.3).sub.2 CHCH.sub.2111 CCl CH CCF.sub.3 6-Cl (CH.sub.3).sub.3 C CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2112 CCl CH CCl 6-Cl cyclopropyl CH.sub.3 CH.sub.2 H 65-67113 CCl CH CCF.sub.3 6-Cl CH.sub.3 CH.sub.2 C(CH.sub.3).sub.2 CH.sub.3 CH.sub.2 H114 CBr CH CCF.sub.3 6-Br (CH.sub.3).sub.3 C (CH.sub.3).sub.2 CH H115 CCl CH CCF.sub.3 H (CH.sub.3).sub.3 C CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2116 CCl CH CCF.sub.3 6-Cl CH.sub.3 CH.sub.2 C(CH.sub.3).sub.2 CH.sub.3 CH.sub.2 CH.sub.3 CH.sub.2117 CCl CH CCF.sub.3 H (CH.sub.3).sub.3 C CH.sub.3 CH.sub.2 H118 CCl CH CCl 6-Cl CH.sub.3 CH.sub.2 C(CH.sub.3).sub.2 CH.sub.3 CH.sub.2 H119 CCl CH CCF.sub.3 6-Cl C.sub.6 H.sub.5 C(CH.sub.3).sub.2 CH.sub.3 CH.sub.2 H120 CCl CH CCF.sub.3 H (CH.sub.3).sub.3 C CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2121 CH CH CCF.sub.3 H (CH.sub.3).sub.3 C CH.sub.3 CH.sub.2 H122 CH CH CCF.sub.3 6-Cl (CH.sub.3).sub.2 CHCH.sub.2 CH.sub.3 CH.sub.2 H 86.5-88.5123 CCl CH CCF.sub.3 6-Cl (CH.sub.3).sub.3 C CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2124 CCl CH CCF.sub.3 6-Cl (CH.sub.3).sub.3 C cyclohexyl H125 CCl CH CCF.sub.3 6-Cl (CH.sub.3).sub.3 C C.sub.6 H.sub.5 CH.sub.2 CH.sub.2 H126 CBr CH CF 6-Br (CH.sub.3).sub.3 C CH.sub.3 CH.sub.2 H127 CCl CCl CCl 5,6-diCl (CH.sub.3).sub.3 C CH.sub.3 CH.sub.2 H 63-65128 CCl CH CCl 6-Cl CH.sub.3 (CH.sub.2).sub.5 C(CH.sub.3).sub.2 CH.sub.3 CH.sub.2 H129 CCl CH CCF.sub.3 6-Cl ##STR32## CH.sub.3 CH.sub.2 H130 CCl CH CCF.sub.3 6-Cl (CH.sub.3).sub.3 C CH.sub.3 (CH.sub.2).sub.2 CH.sub.2 H131 CCl CH CCF.sub.3 6-Cl (CH.sub.3).sub.3 C (CH.sub.3).sub.2 H132 CCl CH CCF.sub.3 6-Cl (CH.sub.3).sub.3 C ##STR33## H133 CCl CH CCl 6-Cl pClC.sub.6 H.sub.5 (CH.sub.3).sub.2 CH H 124-127134 CCl CH CCl 6-Cl pClC.sub.6 H.sub.5 CH.sub.3 CH.sub.2 H 127-132135 CCl CH CCF.sub.3 6-Cl C.sub.6 H.sub.5 C(CH.sub.3).sub.2 C.sub.6 H.sub.5 CH.sub.2 CH.sub.2 H136 CCl CH CCF.sub.3 6-Cl ##STR34## CH.sub.3 CH.sub.2 H 74-75137 CCF.sub.3 CH CH H (CH.sub.3).sub.3 C CH.sub.3 CH.sub.2 H138 CCl CH CCF.sub.3 H (CH.sub.3).sub.3 C C.sub.6 H.sub.5 CH.sub.2 CH.sub.2 H139 CCl CH CCF.sub.3 H (CH.sub.3).sub.3 C ##STR35## H140 CH CH CCF.sub.3 H (CH.sub.3).sub.3 C ##STR36## H141 CCl CH CCF.sub.3 6-Cl pClC.sub.6 H.sub.5 C(CH.sub.3).sub.2 CH.sub.3 CH.sub.2 H142 CCl CH CCF.sub.3 6-Cl (CH.sub.3).sub.3 C C.sub.6 H.sub.5 CH(CH.sub.3) H143 CCl CH CCF.sub.3 6-Cl (CH.sub.3).sub.3 C (CH.sub.3).sub.2 NCH.sub.2 CH.sub.2 H144 CCl CH CCF.sub.3 6-Cl (CH.sub.3).sub.3 C CH.sub.3 CH.sub.2 C(CH.sub.3).sub.2 H145 CCl CH CCF.sub.3 6-Cl (CH.sub.3).sub.3 C ##STR37## H 100.5-101.5 146* CCl CH CCF.sub.3 6-Cl (CH.sub.3).sub.3 C CH.sub.3 CH.sub.2 H 202-202.5147 CBr CH CCF.sub.3 6-Br (CH.sub.3).sub.3 C ##STR38## H148 CCl CH CCF.sub.3 6-Cl ##STR39## CH.sub.3 CH.sub.2 H149 CCl CH CCF.sub.3 6-Cl ##STR40## CH.sub.3 CH.sub.2 H150 CCl CH CCF.sub.3 6-Cl CH.sub.3 CH.sub.2 C(CH.sub.3).sub.2 C.sub.6 H.sub.5 CH.sub.2 CH.sub.2 H151 CCl CH CCF.sub.3 6-Cl (CH.sub.3).sub.3 C C.sub.6 H.sub.5 CH.sub.2 H152 CCl CH CCF.sub.3 6-Cl (CH.sub.3).sub.3 C CH.sub.3 CH.sub.2 CH.sub.3 CH.sub.2153 CCl CH CCF.sub.3 6-Cl ##STR41## CH.sub.3 CH.sub.2 H154 CCl CH CCF.sub.3 6-Cl ##STR42## (CH.sub.3).sub.2 CH H155 CCl CH CCF.sub.3 6-Cl ClCH.sub.2 C(CH.sub.3).sub.2 pCF.sub.3 OC.sub.6 H.sub.5 H 203-205156 CCl CH CCF.sub.3 6-Cl (CH.sub.3).sub.3 C neopentyl H157 CCl CH CCF.sub.3 6-Cl (CH.sub.3).sub.3 C H.sub.2 NCOCCH(CH.sub.3).sub.2 H 160-162158 CCl CH CCF.sub.3 6-Cl (CH.sub.3).sub.3 C ##STR43##159 CCl CH CCF.sub.3 6-Cl (CH.sub.3).sub.3 C pClC.sub.6 H.sub.5 CH.sub.2 CH.sub.2 H160 CCl CH CCF.sub.3 6-Cl (CH.sub.3).sub.3 C ##STR44## H161 CCl CH CCF.sub.3 6-Cl (CH.sub.3).sub.3 C ##STR45## H162 CCl CH CCF.sub.3 6-Cl (CH.sub.3).sub.3 C CH.sub.3 (CH.sub.2).sub.4 CH(CH.sub.3) H163 CCl CH CCF.sub.3 6-Cl (CH.sub.3).sub.3 C (C.sub.2 H.sub.5).sub.2 N(CH.sub.2).sub.3 CH(CH.sub.3) H164 CCl CH CCF.sub.3 6-Cl (CH.sub.3).sub.3 C CH.sub.2 CHCH.sub.2 H165 CCl CH CCF 6-Cl 1-methylcyclohexyl CH.sub.3 CH.sub.2 H166 CCl CH CH 5-CF.sub.3 (CH.sub.3).sub.3 C CH.sub.3 CH.sub.2 H167 CF CF CF 5,6-diF (CH.sub.3).sub.3 C CH.sub.3 CH.sub.2 H168 CBr CH CF 6-Br (CH.sub.3).sub.3 C CH.sub.3 CH.sub.2 H169 CCl CH CCF.sub.3 6-Cl (CH.sub.3).sub.3 C ##STR46## H__________________________________________________________________________ *Hydrochloride salt

EXAMPLE 170

Insecticidal and Acaricidal Evaluation of N-aryl-amidrazone compounds

Test solutions are prepared by dissolving the test compound in a 35% acetone in water mixture to give a concentration of 10,000 ppm. Subsequent dilutions are made with water as needed.

Spodoptera eridania, 3rd instar larvae, southern armyworm

A Sieva limabean leaf expanded to 7-8 cm in length is dipped in the test solution with agitation for 3 seconds and allowed to dry in a hood. The leaf is then placed in a 100.times.10 mm petri dish containing a damp filterpaper on the bottom and ten 3rd instar caterpillars. At 3 and 5 days, observations are made of mortality, reduced feeding, or any interference with normal molting.

Tetranychus urticae(OP-resistant strain), 2-spotted spider mite

Sieva limabean plants with primary leaves expanded to 7-8 cm are selected and cut back to one plant per pot. A small piece is cut from an infested leaf taken from the main colony and placed on each leaf of the test plants. This is done about 2 hours before treatment to allow the mites to move over to the test plant to lay eggs. The size of the cut, infested leaf is varied to obtain about 100 mites per leaf. At the time of test treatment, the piece of leaf used to transfer the mites is removed and discarded. The newly mite-infested plants are dipped An the test solution for 3 seconds with agitation and set in the hood to dry. After 2 days, one leaf is removed and mortality counts are made. After 5 days, another leaf As removed and observations are made of mortality of the eggs and/or newly emerged nymphs.

Diabrotic undecimpunctata howardi, 3rd instar southern corn rootworm

One cc of fine talc is placed in a 30 ml wide-mouth screw-top glass jar. One mL of the appropriate acetone test solution is pipetted onto the talc so as to provide 1.25 mg of active ingredient per jar. The jars are set under a gentle air flow until the acetone is evaporated. The dried talc is loosened, 1 cc of millet seed is added to serve as food for the insects and 25 mL of moist soil is added to each jar. The jar is capped and the contents thoroughly mixed on a Vortex Mixer. Following this, ten 3rd instar rootworms are added to each jar and the jars are loosely capped to allow air exchange for the larvae. The treatments are held for 6 days when mortality counts are made. Missing larvae are presumed dead, since they decompose rapidly and can not be found. The concentrations used in this test correspond approximately to 50 kg/ha.

The data obtained are shown in Table IV.

TABLE IV______________________________________Insecticidal and Acaricidal Evaluationof N-Arylamidrazones% MortalityCompound Armyworm.sup.1 2-Spotted Mite.sup.2 Corn Rootworm.sup.3(Ex. No.) (300 ppm) (300 ppm) (50 kg/ha)______________________________________ 85 0 0 100 86 100 0 80 87 40 90 100 88 -- -- -- 89 0 0 100 90 0 0 20 91 0 80 100 92 0 0 100 93 0 0 100 94 -- 80 100 95 80 0 100 96 100 40 80 97 0 0 100 98 40 0 40100 0 40 0101 0 0 60102 0 60 100103 40 0 100104 0 90 50105 20 0 90106 40 0 100107 -- -- 100108 90 50 100109 0 0 50110 0 0 100111 100 40 90112 40 100 20113 20 100 100114 40 100 100115 0 0 100116 20 50 100117 20 0 100118 50 70 100119 100 50 90120 -- 30 20121 80 40 100122 0 0 40123 0 0 60124 50 80 100125 0 30 100126 0 80 90128 0 0 30129 100 40 0130 80 80 100131 70 0 100132 -- 40 100133 -- 0 0134 0 30 0135 0 0 0136 0 70 100137 0 0 100138 0 0 100139 0 70 100140 0 0 50141 100 0 0142 0 0 100143 0 0 100144 0 0 100145 0 0 100146 0 0 100147 0 0 100148 50 0 100149 100 80 80150 0 60 100152 80 0 100153 100 0 100156 -- 0 100157 0 0 100158 40 0 100159 0 0 100160 0 0 100161 0 0 --162 0 100 100163 0 0 100164 0 0 100167 0 0 100168 0 80 90169 0 0 100______________________________________ .sup.1 Armyworm is 3rd instar larvae, southern armyworm .sup.2 2Spotted Mite is 2spotted spider mite (OPresistant) .sup.3 Corn Rootworm is 3rd instar southern corn rootworm

Claims

1. A compound having the structure of formula I ##STR47## wherein A is C--R.sub.4 ;

B is C--R.sub.5 ;

W is C--R.sub.6 ;

Y is halogen, CN, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.1 -C.sub.6 alkoxy or C.sub.1 -C.sub.6 haloalkoxy;

n is an integer of 0, 1 or 2;

R is C.sub.1 -C.sub.10 alkyl optionally substituted with one or more halogens,

C.sub.3 -C.sub.6 cycloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, (C.sub.1 -C.sub.4 alkyl)SO.sub.x, (C.sub.1 -C.sub.4 haloalkyl)SO.sub.x,

phenyl optionally substituted with one to three halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, (C.sub. -C.sub.4 alkyl)SO.sub.x, (C.sub. -C.sub.4 haloalkyl)-SO.sub.x, NO.sub.2 or CN groups, or

phenoxy optionally substituted with one to three halogen, C.sub.1 -C.sub.4 alkyl, C.sub. -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, (C.sub.1 -C.sub.4 alkyl)SO.sub.x, (C.sub.1 -C.sub.4 haloalkyl)SO.sub.x, NO.sub.2 or CN groups,

C.sub.3 -C.sub.12 cycloalkyl optionally substituted with one or more halogens,

C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, (C.sub.1 -C.sub.4 alkyl)SO.sub.x, (C.sub.1 -C.sub.4 haloalkyl)SO.sub.x,

phenyl optionally substituted with one to three halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, NO.sub.2 or CN groups, or

phenoxy optionally substituted with one to three halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, NO.sub.2 or CN groups;

R.sub.1 is hydrogen;

R.sub.2 and R.sub.3 are each independently hydrogen,

C.sub.1 -C.sub.10 alkyl optionally substituted with one or more halogen, hydroxy, C.sub.1 -C.sub.4 alkoxy,

(C.sub.1 -C.sub.4 alkyl)SO.sub.x, CONR.sub.7 R.sub.8, CO.sub.2 R.sub.9 R.sub.10, R.sub.11,

C.sub.3 -C.sub.6 cycloalkyl optionally substituted with one to three halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, NO.sub.2 or CN groups,

phenyl optionally substituted with one or more halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub. -C.sub.4 haloalkoxy, NO.sub.2 or CN groups, or

pyridyl optionally substituted with one or more halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, NO.sub.2 or CN groups,

C.sub.3 -C.sub.10 alkenyl optionally substituted with one or more halogen, hydroxy, C.sub.1 -C.sub.4 alkoxy, (C.sub.1 -C.sub.4 alkyl)SO.sub.x, CONR.sub.7 R.sub.8, CO.sub.2 R.sub.9, R.sub.10, R.sub.11,

C.sub.3 -C.sub.6 cycloalkyl optionally substituted with one to three halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, NO.sub.2 or CN groups,

phenyl optionally substituted with one or more halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, NO.sub.2 or CN groups, or

pyridyl optionally substituted with one or more halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, NO.sub.2 or CN groups,

C.sub.3 -C.sub.10 alkynyl optionally substituted with one or more halogen, hydroxy, C.sub.1 -C.sub.4 alkoxy, (C.sub.1 -C.sub.4 alkyl)SO.sub.x, CONR.sub.7 R.sub.8, CO.sub.2 R.sub.9, R.sub.10, R.sub.11,

C.sub.3 -C.sub.6 cycloalkyl optionally substituted with one to three halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, NO.sub.2 or CN groups,

phenyl optionally substituted with one or more halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, NO.sub.2 or CN groups, or

pyridyl optionally substituted with one or more halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, NO.sub.2 or CN groups,

C.sub.3 -C.sub.12 cycloalkyl optionally substituted with one or more halogen, hydroxy, C.sub.1 -C.sub.4 alkoxy, (C.sub.1 -C.sub.4 alkyl)SO.sub.x, CONR.sub.7 R.sub.8, CO.sub.2 R.sub.9, R.sub.10, R.sub.11,

C.sub.3 -C.sub.6 cycloalkyl optionally substituted with one to three halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, NO.sub.2 or CN groups,

phenyl optionally substituted with one or more halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, NO.sub.2 or CN groups, or

pyridyl optionally substituted with one or more halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, NO.sub.2 or CN groups or

R.sub.2 and R.sub.3 may be taken together to form, a ring represented by the structure ##STR48## R.sub.4, R.sub.5 and R.sub.6 are each independently hydrogen, halogen, CN, NO.sub.2, (C.sub.1 -C.sub.4 alkyl)SO.sub.x, (C.sub.1 -C.sub.4 haloalkyl)SO.sub.x, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.1 -C.sub.6 alkoxy or C.sub.1 -C.sub.6 haloalkoxy;

R.sub.7, R.sub.8 and R.sub.9 are each independently hydrogen or C.sub.1 -C.sub.4 alkyl;

R.sub.10 is NR.sub.12 R.sub.13, ##STR49## R.sub.11 is ##STR50## R.sub.12, R.sub.13, R.sub.14 and R.sub.15 are each independently hydrogen or C.sub.1 -C.sub.4 alkyl ;

X is O, S or NR.sub.14 ;

r is an integer of 0 or 1;

p and m are each independently an integer of 0, 1, 2 or 3 with the proviso that the sum of p+m+r must be 4, 5 or 6;

x is an integer of 0, 1 or 2; or the acid addition salts thereof;

with the proviso that one of R.sub.2 and R.sub.3 is other than hydrogen and with the further proviso that if R.sub.4, R.sub.5 and R.sub.6 are all hydrogen then n cannot be 0.

2. A compound having the structure ##STR51## wherein R is C.sub.1 -C.sub.10 alkyl;

R.sub.1 is hydrogen

R.sub.2 is C.sub.1 -C.sub.10 alkyl;

R.sub.3 is hydrogen or C.sub.1 -C.sub.10 alkyl; and

R.sub.4, R.sub.6 and Y are each independently hydrogen, halogen, CN, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.1 -C.sub.6 alkoxy or C.sub.1 -C.sub.6 haloalkoxy.

3. The compound according to claim 2 wherein R.sub.1 are R.sub.3 are hydrogen.

4. The compound according to claim 3 wherein Y is halogen, R.sub.4 and R.sub.6 are each independently halogen or C.sub.1 -C.sub.6 alkyl substituted with one or more halogens.

5. The compound according to claim 4 wherein Y is chlorine and R.sub.6 is trifluoromethyl.

6. The compound according to claim 4 wherein R is t-butyl and R.sub.2 is ethyl.

7. The compound according to claim 6 N-ethyl-2,2-dimethylpropionamide, 2-(2,6-dichloro-.alpha.,.alpha.,.alpha. trifluoro-p-tolylhydrazone.