Pyridazinone derivatives, and insecticidal, acaricidal and nematicidal compositions

Abstract

Compounds of the following formula: ##STR1## wherein Z.sup.3 represents halogen atom, straight or branched chain alkyl group having 1 to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms, alkylcarbonyl having 2 to 10 carbon atoms, alkoxyalkyl group having 2 to 4 carbon atoms, ##STR2## W represents halogen atom, alkyl group having 1 to 4 carbon atoms, alkoxy group having 1 to 4 carbon atoms, haloalkyl group having 1 to 4 carbon atoms, or nitro group, m is 0 or an integer of 1 to 2, and when m is 2, W may be same or different, and compositions for controlling insects, acari and nemati which contain such compound.

Description

BACKGROUND OF THE INVENTION

1. Field of the Invention

This invention relates to novel 3(2H)-pyridazinone derivatives; preparation thereof; insecticidal, acaricidal, and nematicidal compositions for agricultural and horticultural uses; and expellent compositions for ticks parasitic on animals; said compositions containing said derivatives as an active ingredient.

2. Description of the Prior Art

The present invention concerns EP-A-0088384, EP-A-0134439, EP-A-0183212 and EP-A-0199281. The known compounds contained in these patent applications are represented by the general formula (IV): ##STR3##

The characteristics of the compounds of these patent applications are, e.g., in the formula (IV):

in case of EP-A-0088384 and EP-A-0134439, Y represents oxygen atom or sulfur atom, but benzyl derivative group is bound thereto as -B'-Q';

in case of EP-A-0183212, A' represents alkyl group or it has double bond or triple bond as B';

in case of EP-A-0199281, Q' represents heterocyclic ring or specific substituent.

The present inventors have intensively conducted research on pyridazinone derivatives which are different from these EPC patent applications in chemical structure and have obtained the present compounds of the general formula (I) given below.

Furthermore, the present inventors have found out that the present compounds of the general formula (I) given below have excellent effective insecticidal, acaricidal and nematicidal activities.

For example, the group of known compounds represented by the aforesaid general formula (IV) have strong insecticidal, acaricidal and nematicidal activities. Even in comparison with those known compounds, however, the present compounds exhibited remarkable activity rise in respect to residual activity, especially for insecticidal and acaricidal activity. Therefore, the present invention was completed by finding out that the present compounds can effectively control pests which are agriculturally and horticulturally harmful even with an extremely low drug concentration in comparison with the known compounds represented by the general formula (IV).

SUMMARY OF THE INVENTION

An object of this invention is to provide novel 3(2H)-pyridazinone derivatives which have insecticidal, acaricidal and nematicidal activities.

Another object of this invention is to provide a process for preparing such 3(2H)-pyridazinone derivatives.

Further object of this invention is to provide insecticidal, acaricidal and nematicidal compositions containing 3(2H)-pyridazinone derivatives as an active ingredient.

Still further object of this invention is to provide a method for controlling pests by using the above-mentioned derivatives or compositions.

Other objects of this invention will become apparent from the description given below.

DETAILED DESCRIPTION OF THE INVENTION

The pyridazinone derivatives according to the invention have the general formula (I): ##STR4## wherein

R represents a straight or branched chain alkyl group having 2 to 6 carbon atoms,

A represents halogen atom,

X represents oxygen atom or sulfur atom,

Y represents oxygen atom, sulfur atom, or CH.sub.2,

R.sup.1 represents hydrogen atom or alkyl having 1 to 4 carbon atoms, Z.sup.1 and Z.sup.4 represent independently hydrogen atom, alkyl group having 1 to 4 carbon atoms, halogen atom, alkoxy group having 1 to 4 carbon atoms or nitro group, with the proviso that when X represents oxygen atom, Z.sup.1 and Z.sup.4 do not represent hydrogen atom; Z.sup.2 represents hydrogen atom, alkyl group having 1 to 4 carbon atoms or alkoxy group having 1 to 4 carbon atoms;

Z.sup.3 represents hydrogen atom, halogen atom, straight or branched chain alkyl group having 1 to 10 carbon atoms, alkenyl group having 2 to 5 carbon atoms, cycloalkyl group having 3 to 6 carbon atoms, straight or branched chain alkoxy group having 1 to 10 carbon atoms, alkylthio group having 1 to 10 carbon atoms, alkylsulfinyl group having 1 to 10 carbon atoms, alkylsulfonyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 5 carbon atoms, haloalkyloxy group having 1 to 5 carbon atoms, alkylcarbonyl amino group having 2 to 5 carbon atoms, nitro group, alkylcarbonyl group having 1 to 10 carbon atoms, napthylcarbonyl group, --COCH.sub.2 C.sub.6 H.sub.5 group, 2-phenylethyl group, hydroxyalkyl group having 1 to 4 carbon atoms, alkoxyalkyl group having 2 to 4 carbon atoms, alkylthioalkyl group having 2 to 4 carbon atoms, alkoxyiminoalkyl group having 2 to 4 carbon atoms, --NHSO.sub.2 CH.sub.3 group, --NHCON(CH.sub.3).sub.2 group, ##STR5## group, cycloalkylcarbonyl group having 4 to 7 carbon atoms or cycloalkylmethyl group having 4 to 7 carbon atoms, ##STR6## provided that l represents 0 or an integer of 1 to 2, R.sup.8 represents hydrogen atom, alkyl group having 1 to 4 carbon atoms or alkylcarbonyl group having 1 to 4 carbon atoms, R.sup.9 to R.sup.10 represent independently hydrogen atom, alkyl group having 1 to 4 carbon atoms, halogen atom, or alkoxy group having 1 to 4 carbon atoms,

W represents halogen atom, alkyl group having 1 to 4 carbon atoms, alkoxy group having 1 to 4 carbon atoms, haloalkyl group having 1 to 4 carbon atoms, or nitro group,

m is 0 or an integer of 1 to 2, and when m is 2, W may be same or different, with the proviso that Z.sup.1, Z.sup.2, Z.sup.3 and Z.sup.4 do not simultaneously represent hydrogen atom.

In respect to the activity for controlling pests, preferable compounds of the present invention are ones in which, in the general formula (I), R represents t-Bu, A represents chlorine atom, R.sup.1 represents hydrogen atom, and Y represents oxygen atom.

More preferred compounds of the general formula (I) among the compounds shown in Tables 1 to 3 are:

______________________________________Nos. 36, 38, 40, 46, 49, 55, 71, 72, 73, 74, 84, 85, 88, 89, 90, 92, 111, 112, 113, 127, 128, 129, 426, 427, 429, 430, 432, 438, 443, 463, 465, 466, 468, 470, 472, 474, 476, 477, 480, 481, 482, 484, 488, 490, 491, 492, 494, 496, 514, 517, 518, 520, 522, 524, 528, 540, 542, 850, 851, 852, 857, 863 and 895.______________________________________

The compounds shown in Tables 1, 2 and 3 are examples. However, the present invention is not restricted to these compounds which are shown as only exemplification.

In Tables 1, 2 and 3, t, i, c and s mean tertiary, iso, cyclo and secondary, respectively, and each symbol Me, Et, Pr, Bu, Am, Pen, Hex and Ph means methyl, ethyl, propyl, butyl, amyl, pentyl, hexyl and phenyl, respectively.

In case of the compounds containing asymmetric carbon atoms among the compounds covered by the present invention, optical isomers, i.e., (+)-isomers and (-)-isomers are also included in the present invention.

TABLE 1__________________________________________________________________________ ##STR7##No. R A X R.sup.1 Y Z.sup.1 Z.sup.2 Z.sup.3 Z.sup.4__________________________________________________________________________12 t-Bu Cl S H O Me H H H13 t-Bu Cl S H O H H Et H14 t-Bu Cl S H O H H Pr H15 t-Bu Cl S H O i-Pr H H H16 t-Bu Cl S H O H H Bu H17 t-Bu Cl S H O H H Pen H18 t-Bu Cl S H O H OPr H H19 t-Bu Cl S H O H H OBu H20 t-Bu Cl S H O H H SMe H21 t-Bu Cl S H O Me H Cl H22 t-Bu Cl S H O Me H Me H23 t-Bu Cl S H O H Me H Me24 t-Bu Cl S H O Me H H Me25 t-Bu Cl S H O Me H Pen H26 t-Bu Cl S H O Et H Pen H27 t-Bu Cl S H O Me H CO(CH.sub.2).sub.3 CH.sub.3 H28 t-Bu Cl S H O OMe H H OMe29 t-Bu Cl S H O Me H H Cl30 t-Bu Cl S H O Cl H H Cl31 t-Bu Cl S H O Me H Cl Cl32 t-Bu Cl S H O Me Me H Me33 t-Bu Cl S H O Me H Me Me34 t-Bu Cl S H O Me H Br Cl35 t-Bu Cl S H O Me H COCH.sub.2 CH.sub.3 Cl36 t-Bu Cl S H O Me H Pr Cl37 t-Bu Cl S H O Me H Bu Cl38 t-Bu Cl S H O Cl H COCH.sub.2 CH.sub.3 Cl39 t-Bu Cl S H O Cl H Et Cl40 t-Bu Cl S H O Cl H Pr Cl41 t-Bu Cl S H O Cl H i-Pr Cl42 t-Bu Cl S H O Cl H Bu Cl43 t-Bu Cl S H O Cl H i-Bu Cl44 t-Bu Cl S H O Cl H t-Bu Cl45 t-Bu Cl S H O Cl H Pen Cl46 t-Bu Cl S H O Cl H Ph Cl47 t-Bu Cl S H O Br H COCH.sub.2 CH.sub.3 Br48 t-Bu Cl S H O Br H Et Br49 t-Bu Cl S H O Br H Pr Br50 t-Bu Cl S H O Br H i-Pr Br51 t-Bu Cl S H O Br H Bu Br52 t-Bu Cl S H O Br H i-Bu Br53 t-Bu Cl S H O Br H t-Bu Br54 t-Bu Cl S H O Br H Ph Br55 t-Bu Cl S H O F H COCH.sub.2 CH.sub.3 F56 t-Bu Cl S H O F H CHCHCH.sub.3 F57 t-Bu Cl S H O F H Pr F58 t-Bu Cl S H O F H Bu F59 t-Bu Cl S H O F H Pen F60 t-Bu Cl S H O F H Et F61 t-Bu Cl S H O NO.sub.2 H Me NO.sub.262 t-Bu Cl S H O NO.sub.2 H Et NO.sub.263 t-Bu Cl S H O NO.sub.2 H Pr NO.sub.264 t-Bu Cl S H O NO.sub.2 H Bu NO.sub.265 t-Bu Cl S H O NO.sub.2 H Pen NO.sub.266 t-Bu Cl S H O OMe H Et OMe67 t-Bu Cl S H O OMe H Pr OMe68 t-Bu Cl S H O OMe H i-Pr OMe69 t-Bu Cl S H O OMe H Bu OMe70 t-Bu Cl S H O OMe H t-Bu OMe71 t-Bu Cl S H O Me H COCH.sub.3 Me72 t-Bu Cl S H O Me H COCH.sub.2 CH.sub.3 Me73 t-Bu Cl S H O Me H COCH.sub.2 CH.sub.2 CH.sub.3 Me74 t-Bu Cl S H O Me H COCH(CH.sub.3).sub.2 Me75 t-Bu Cl S H O Me H COc-Pr Me76 t-Bu Cl S H O Me H CO(CH.sub.2).sub.3 CH.sub.3 Me77 t-Bu Cl S H O Me H COc-Hex Me78 t-Bu Cl S H O Me H CO(CH.sub.2).sub.4 CH.sub.3 Me79 t-Bu Cl S H O Me H CO(CH.sub.2).sub.6 CH.sub.3 Me80 t-Bu Cl S H O Me H CO(CH.sub.2).sub.8 CH.sub.3 Me81 t-Bu Cl S H O Me H Cl Me82 t-Bu Cl S H O Me H Br Me83 t-Bu Cl S H O Me H I Me84 t-Bu Cl S H O Me H Et Me85 t-Bu Cl S H O Me H Pr Me86 t-Bu Cl S H O Me H i-Pr Me87 t-Bu Cl S H O Me H CH.sub.2 CHCH.sub.2 Me88 t-Bu Cl S H O Me H Bu Me89 t-Bu Cl S H O Me H i-Bu Me90 t-Bu Cl S H O Me H CH.sub.2c-Pr Me91 t-Bu Cl S H O Me H CH.sub.2 CCH Me92 t-Bu Cl S H O Me H t-Bu Me93 t-Bu Cl S H O Me H Pen Me94 t-Bu Cl S H O Me H t-Am Me95 t-Bu Cl S H O Me H Hex Me96 t-Bu Cl S H O Me H c-Hex Me97 t-Bu Cl S H O Me H (CH.sub.2).sub.7 CH.sub.3 Me98 t-Bu Cl S H O Me H (CH.sub.2).sub.9 CH.sub.3 Me99 t-Bu Cl S H O Me H CH.sub.2c-Hex Me100 t-Bu Cl S H O Me H Ph Me102 t-Bu Cl S H O Me H NO.sub.2 Me103 t-Bu Cl S H O Me H COOMe Me104 t-Bu Cl S H O Me H COOEt Me105 t-Bu Cl S H O Me H COOPr Me106 t-Bu Cl S H O Me H CH.sub.2 CF.sub.3 Me107 t-Bu Cl S H O Me H CH.sub.2 CH.sub.2 CF.sub.3 Me108 t-Bu Cl S H O Me H NMe.sub.2 Me109 t-Bu Cl S H O Me H NEt.sub.2 Me110 t-Bu Cl S H O Me H NPr.sub.2 Me111 t-Bu Cl S H O Me H OMe Me112 t-Bu Cl S H O Me H OEt Me113 t-Bu Cl S H O Me H OPr Me114 t-Bu Cl S H O Me H Oi-Pr Me115 t-Bu Cl S H O Me H OBu Me116 t-Bu Cl S H O Me H Ot-Bu Me117 t-Bu Cl S H O Me H OPen Me118 t-Bu Cl S H O Me H Oc-Hex Me119 t-Bu Cl S H O Me H OCH.sub.2 CHCH.sub.2 Me120 t-Bu Cl S H O Me H OCH.sub.2 CCH Me121 t-Bu Br S H O Me H COCH.sub.2 CH.sub.3 Me122 t-Bu OMe S H O Me H COCH.sub.2 CH.sub.3 Me123 t-Bu SMe S H O Me H COCH.sub.2 CH.sub.3 Me124 t-Bu Br S H O Me H Pr Me125 t-Bu OMe S H O Me H Pr Me126 t-Bu SMe S H O Me H Pr Me127 t-Bu Cl S H O Me H SMe Me128 t-Bu Cl S H O Me H SEt Me129 t-Bu Cl S H O Me H SPr Me130 t-Bu Cl S H O Me H SOMe Me131 t-Bu Cl S H O Me H SOEt Me132 t-Bu Cl S H O Me H SOPr Me133 t-Bu Cl S H O Me H SO.sub.2 Me Me134 t-Bu Cl S H O Me H SO.sub.2 Et Me135 t-Bu Cl S H O Me H SO.sub.2 Pr Me136 t-Bu Cl S H O Me H SCH.sub.2 CHCH.sub.2 Me137 t-Bu Cl S H O Me H SCH.sub.2 CCH Me138 t-Bu Cl S H O Me H SOCH.sub.2 CHCH.sub.2 Me139 t-Bu Cl S H O Me H SOCH.sub.2 CCH Me140 t-Bu Cl S H O Me H SO.sub.2 CH.sub.2 CHCH.sub.2 Me141 t-Bu Cl S H O Me H SO.sub.2 CH.sub.2 CCH Me142 t-Bu Cl S H O Me H Si-Pr Me143 t-Bu Cl S H O Me H St-Br Me144 t-Bu Cl S H O Me H Sc-Hex Me145 t-Bu Cl S H O Me H SO.sub.2i-Pr Me146 t-Bu Cl S H O Me H SO.sub.2t-Bu Me147 t-Bu Cl S H O Me H SOc-Hex Me148 t-Bu Cl S H O Cl Et Cl Cl149 t-Bu Cl S H O Cl Pr Cl Cl150 t-Bu Cl S H O Cl t-Bu Cl Cl151 t-Bu Cl S H S H H t-Bu H152 t-Bu Cl S H S Me H H Me153 t-Bu Cl S H S Me H Me Me154 t-Bu Cl S H S Me H COCH.sub.2 CH.sub.3 Me155 t-Bu Cl S H S Me H Pr Me156 t-Bu Cl S H S Me H OEt Me161 t-Bu Cl S H CH.sub.2 H H t-Bu H162 t-Bu Cl S H CH.sub.2 Me H H Me163 t-Bu Cl S H CH.sub.2 Me H COCH.sub.2 CH.sub.3 Me164 t-Bu Cl S H CH.sub.2 Me H Pr Me165 t-Bu Cl S H CH.sub.2 Me H OEt Me171 t-Bu Cl S Me O H H t-Bu H172 t-Bu Cl S Me O Me H H Me173 t-Bu Cl S Me O Me H COCH.sub.2 CH.sub.3 Me174 t-Bu Cl S Me O Me H Pr Me175 t-Bu Cl S Me O Me H OEt Me198 t-Bu Cl O H S Me H H Me199 t-Bu Cl O H S Me H Me Me219 t-Bu Cl O H O Me H H Me223 t-Bu Cl O H O OMe H H OMe224 t-Bu Cl O H O Me H H Cl225 t-Bu Cl O H O Cl H H Cl226 t-Bu Cl O H O Me H Cl Cl227 Pr Cl O H O Me H Cl Cl228 t-Bu Cl O H O Me Me H Me229 t-Bu Cl O H O Me H Me Me230 t-Bu Cl O H O Me H Br Cl231 t-Bu Cl O H O Me H COCH.sub.2 CH.sub.3 Cl232 t-Bu Cl O H O Me H Pr Cl233 t-Bu Cl O H O Cl H COCH.sub.2 CH.sub.3 Cl234 t-Bu Cl O H O Cl H Et Cl235 t-Bu Cl O H O Cl H Pr Cl236 t-Bu Cl O H O Cl H i-Pr Cl237 t-Bu Cl O H O Cl H Bu Cl238 t-Bu Cl O H O Cl H i-Bu Cl239 t-Bu Cl O H O Cl H t-Bu Cl240 t-Bu Cl O H O Cl H Pen Cl241 t-Bu Cl O H O Cl H Ph Cl242 t-Bu Cl O H O Br H COCH.sub.2 CH.sub.3 Br243 t-Bu Cl O H O Br H Et Br244 t-Bu Cl O H O Br H Pr Br245 t-Bu Cl O H O Br H i-Pr Br246 t-Bu Cl O H O Br H Bu Br247 t-Bu Cl O H O Br H i-Bu Br248 t-Bu Cl O H O Br H t-Bu Br249 t-Bu Cl O H O Br H Ph Br250 t-Bu Cl O H O F H COCH.sub.2 CH.sub.3 F251 t-Bu Cl O H O F H CHCHCH.sub.3 F252 t-Bu Cl O H O F H Pr F253 t-Bu Cl O H O F H Bu F254 t-Bu Cl O H O F H Pen F255 t-Bu Cl O H O F H Et F256 t-Bu Cl O H O NO.sub.2 H Me NO.sub.2257 t-Bu Cl O H O NO.sub.2 H Et NO.sub.2258 t-Bu Cl O H O NO.sub.2 H Pr NO.sub.2259 t-Bu Cl O H O NO.sub.2 H Bu NO.sub.2260 t-Bu Cl O H O NO.sub.2 H Pen NO.sub.2261 t-Bu Cl O H O OMe H Et OMe262 t-Bu Cl O H O OMe H Pr OMe263 t-Bu Cl O H O OMe H i-Pr OMe264 t-Bu Cl O H O OMe H Bu OMe265 t-Bu Cl O H O OMe H t-Bu OMe266 t-Bu Cl O H O Me H COCH.sub.3 Me267 t-Bu Cl O H O Me H COCH.sub.2 CH.sub.3 Me268 t-Bu Cl O H O Me H COCH.sub.2 CH.sub.2 CH.sub.3 Me269 t-Bu Cl O H O Me H COCH(CH.sub.3).sub.2 Me270 t-Bu Cl O H O Me H COc-Pr Me271 t-Bu Cl O H O Me H CO(CH.sub.2).sub.3 CH.sub.3 Me272 t-Bu Cl O H O Me H COc-Hex Me273 t-Bu Cl O H O Me H CO(CH.sub.2).sub.4 CH.sub.3 Me274 t-Bu Cl O H O Me H CO(CH.sub.2).sub.6 CH.sub.3 Me275 t-Bu Cl O H O Me H CO(CH.sub.3).sub.8 CH.sub.3 Me276 t-Bu Cl O H O Me H Cl Me277 t-Bu Cl O H O Me H Br Me278 t-Bu Cl O H O Me H I Me279 t-Bu Cl O H O Me H Et Me280 t-Bu Cl O H O Me H Pr Me281 t-Bu Cl O H O Me H i-Pr Me282 t-Bu Cl O H O Me H CH.sub.2 CHCH.sub.2 Me283 t-Bu Cl O H O Me H Bu Me284 t-Bu Cl O H O Me H i-Bu Me285 t-Bu Cl O H O Me H CH.sub.2c-Pr Me286 t-Bu Cl O H O Me H CH.sub.2 CCH Me287 t-Bu Cl O H O Me H t-Bu Me288 t-Bu Cl O H O Me H Pen Me289 t-Bu Cl O H O Me H t-Am Me290 t-Bu Cl O H O Me H Hex Me291 t-Bu Cl O H O Me H c-Hex Me292 t-Bu Cl O H O Me H (CH.sub.2).sub.7 CH.sub.3 Me293 t-Bu Cl O H O Me H (CH.sub.2).sub.9 CH.sub.3 Me294 t-Bu Cl O H O Me H CH.sub.2c-Hex Me295 t-Bu Cl O H O Me H Ph Me296 t-Bu Cl O H O Me H NO.sub.2 Me298 t-Bu Cl O H O Me H COOMe Me299 t-Bu Cl O H O Me H COOEt Me300 t-Bu Cl O H O Me H COOPr Me301 t-Bu Cl O H O Me H CH.sub.2 CF.sub.3 Me302 t-Bu Cl O H O Me H CH.sub.2 CH.sub.2 CF.sub.3 Me303 t-Bu Cl O H O Me H NMe.sub.2 Me304 t-Bu Cl O H O Me H NEt.sub.2 Me305 t-Bu Cl O H O Me H NPr.sub.2 Me306 t-Bu Cl O H O Me H OMe Me307 t-Bu Cl O H O Me H OEt Me308 t-Bu Cl O H O Me H OPr Me309 t-Bu Cl O H O Me H Oi-Pr Me310 t-Bu Cl O H O Me H OBu Me311 t-Bu Cl O H O Me H Ot-Bu Me312 t-Bu Cl O H O Me H OPen Me313 t-Bu Cl O H O Me H Oc-Hex Me314 t-Bu Cl O H O Me H OCH.sub.2 CHCH.sub.2 Me315 t-Bu Cl O H O Me H OCH.sub.2 CCH.sub.3 Me316 t-Bu Br O H O Me H COCH.sub.2 CH.sub.3 Me317 t-Bu OMe O H O Me H COCH.sub.2 CH.sub.3 Me318 t-Bu SMe O H O Me H COCH.sub.2 CH.sub.3 Me319 t-Bu Br O H O Me H Pr Me320 t-Bu OMe O H O Me H Pr Me321 t-Bu SMe O H O Me H Pr Me322 t-Bu Cl O H O Me H SMe Me323 t-Bu Cl O H O Me H SEt Me324 t-Bu Cl O H O Me H SPr Me325 t-Bu Cl O H O Me H SOMe Me326 t-Bu Cl O H O Me H SOEt Me327 t-Bu Cl O H O Me H SOPr Me328 t-Bu Cl O H O Me H SO.sub.2 Me Me329 t-Bu Cl O H O Me H SO.sub.2 Et Me330 t-Bu Cl O H O Me H SO.sub.2 Pr Me331 t-Bu Cl O H O Me H SCH.sub.2 CHCH.sub.2 Me332 t-Bu Cl O H O Me H SCH.sub.2 CCH.sub.3 Me333 t-Bu Cl O H O Me H SOCH.sub.2 CHCH.sub.2 Me334 t-Bu Cl O H O Me H SOCH.sub.2 CCH.sub.3 Me335 t-Bu Cl O H O Me H SO.sub.2 CH.sub.2 CHCH.sub.2 Me336 t-Bu Cl O H O Me H SO.sub.2 CH.sub.2 C CH.sub.3 Me337 t-Bu Cl O H O Me H Si-Pr Me338 t-Bu Cl O H O Me H St-Bu Me339 t-Bu Cl O H O Me H Sc-Hex Me340 t-Bu Cl O H O Me H SO.sub.2i-Pr Me341 t-Bu Cl O H O Me H SO.sub.2t-Bu Me342 t-Bu Cl O H O Me H SO.sub.2c-Hex Me343 t-Bu Cl O H O Cl Et Cl Cl344 t-Bu Cl O H O Cl t-Bu Cl Cl360 t-Bu Cl O Me O Me H Pr Me__________________________________________________________________________ TABLE 2__________________________________________________________________________ ##STR8##No. R A X R.sup.1 Y Z.sup.5 Q Z.sup.6.sub.n__________________________________________________________________________421 t-Bu Cl S H O H O H422 t-Bu Cl S H O H O 4-Cl423 t-Bu Cl S H O H O 4-Me424 t-Bu Cl S H O Cl O H425 t-Bu Cl S H O Cl O 4-Me426 t-Bu Cl S H O Me O H427 t-Bu Cl S H O Me O 4-Cl428 t-Bu Cl S H O Me O 2-Me429 t-Bu Cl S H O Me O 4-Me430 t-Bu Cl S H O Me O 4-Et431 t-Bu Cl S H O Me O 4-t-Bu432 t-Bu Cl S H O Me O 4-OMe433 t-Bu Cl S H O Me O 4-CF.sub.3434 t-Bu Cl S H O Me O 4-NO.sub.2435 t-Bu Cl S H O Me O 4-CN436 t-Bu Cl S H O Me O 4-OCF.sub.3437 t-Bu Cl S H O Me O 2-Cl,4-Cl438 t-Bu Cl S H O Me O 2-Me,4-Me439 t-Bu Cl S H O Me O 2-Cl,4-Cl,6-Cl440 t-Bu Cl S H O Me O 2-Me,4-Me,6-Me441 t-Bu Cl S H O H S H442 t-Bu Cl S H O H S 4-Me443 t-Bu Cl S H O Me S H444 t-Bu Cl S H O Me S 4-F445 t-Bu Cl S H O Me S 4-Cl446 t-Bu Cl S H O Me SO 4-Cl447 t-Bu Cl S H O Me SO.sub.2 4-Cl448 t-Bu Cl S H O Me S 4-Me449 t-Bu Cl S H O Me SO 4-Me450 t-Bu Cl S H O Me SO.sub.2 4-Me451 t-Bu Cl S H O H NH H452 t-Bu Cl S H O H NH 4-Cl453 t-Bu Cl S H O Me NH H454 t-Bu Cl S H O Me NH 4-Cl455 t-Bu Cl S H O Me NMe H456 t-Bu Cl S H O Me NMe 4-Cl457 t-Bu Cl S H O Me NCOMe H458 t-Bu Cl S H O Me NCOMe 4-Cl459 t-Bu Cl S H O H CO H460 t-Bu Cl S H O H CO 4-Cl461 t-Bu Cl S H O H CO 4-Me462 t-Bu Cl S H O Cl CO H463 t-Bu Cl S H O Cl CO 4-Cl464 t-Bu Cl S H O Cl CO 4-Me465 t-Bu Cl S H O Me CO H466 t-Bu Cl S H O Me CO 2-Cl467 t-Bu Cl S H O Me CO 3-Cl468 t-Bu Cl S H O Me CO 4-Cl469 t-Bu Cl S H O Me CO 2-F470 t-Bu Cl S H O Me CO 4-F471 t-Bu Cl S H O Me CO 2-Br472 t-Bu Cl S H O Me CO 4-Br473 t-Bu Cl S H O Me CO 4-I474 t-Bu Cl S H O Me CO 2-Me475 t-Bu Cl S H O Me CO 3-Me476 t-Bu Cl S H O Me CO 4-Me477 t-Bu Cl S H O Me CO 4-Et478 t-Bu Cl S H O Me CO 4-Bu479 t-Bu Cl S H O Me CO 4-i-Pr480 t-Bu Cl S H O Me CO 4-t-Bu481 t-Bu Cl S H O Me CO 4-CF.sub.3482 t-Bu Cl S H O Me CO 4-NO.sub.2483 t-Bu Cl S H O Me CO 4-CN484 t-Bu Cl S H O Me CO 4-OMe485 t-Bu Cl S H O Me CO 4-OEt486 t-Bu Cl S H O Me CO 4-SMe487 t-Bu Cl S H O Me CO 4-NMe.sub.2488 t-Bu Cl S H O Me CO 2-F,4-F489 t-Bu Cl S H O Me CO 2-F,6-F490 t-Bu Cl S H O Me CO 2-Cl,4-Cl491 t-Bu Cl S H O Me CO 2-Cl,6-Cl492 t-Bu Cl S H O Me CO 3-Cl,4-Cl493 t-Bu Cl S H O Me CO 3-Cl,5-Cl494 t-Bu Cl S H O Me CO 2-Cl,4-NO.sub.2495 t-Bu Cl S H O Me CO 2-NO.sub.2,4-Cl496 t-Bu Cl S H O Me CO 2-Me,4-Me497 t-Bu Cl S H O Me CO 2-Me,6-Me498 t-Bu Cl S H O Me CO 3-Me,4-Me499 t-Bu Cl S H O Me CO 3-Me,5-Me500 t-Bu Cl S H O Me CO 3,4-CHCHCHCH501 t-Bu Cl S H O Me CO 2-Cl,4-Me502 t-Bu Cl S H O Me CO 2-Cl,6-Me503 t-Bu Cl S H O Me CO 2-Me,4-Cl504 t-Bu Cl S H O Me CO 2-Cl,4-Cl,6-Cl505 t-Bu Cl S H O Me CO 2-Me,4-Me,5-Me506 t-Bu Cl S H O Me CO 2-Me,4-Me,6-Me507 t-Bu Br S H O Me CO H508 t-Bu OMe S H O Me CO H509 t-Bu SMe S H O Me CO H510 t-Bu Cl S H O i-Pr CO H511 t-Bu Cl S H O H CH.sub.2 H512 t-Bu Cl S H O H CH.sub.2 4-Cl513 t-Bu Cl S H O H CH.sub.2 4-Me514 t-Bu Cl S H O Cl CH.sub.2 H515 t-Bu Cl S H O Cl CH.sub.2 4-Cl516 t-Bu Cl S H O Cl CH.sub.2 4-Me517 t-Bu Cl S H O Me CH.sub.2 H518 t-Bu Cl S H O Me CH.sub.2 2-Cl619 t-Bu Cl S H O Me CH.sub.2 3-Cl520 t-Bu Cl S H O Me CH.sub.2 4-Cl521 t-Bu Cl S H O Me CH.sub.2 2-F522 t-Bu Cl S H O Me CH.sub.2 4-F523 t-Bu Cl S H O Me CH.sub.2 2-Br524 t-Bu Cl S H O Me CH.sub.2 4-Br525 t-Bu Cl S H O Me CH.sub.2 4-I526 t-Bu Cl S H O Me CH.sub.2 2-Me527 t-Bu Cl S H O Me CH.sub.2 3-Me528 t-Bu Cl S H O Me CH.sub.2 4-Me529 t-Bu Cl S H O Me CH.sub.2 4-Et530 t-Bu Cl S H O Me CH.sub.2 4-Bu531 t-Bu Cl S H O Me CH.sub.2 4-i-Pr532 t-Bu Cl S H O Me CH.sub.2 4-t-Bu533 t-Bu Cl S H O Me CH.sub.2 4-CF.sub.3534 t-Bu Cl S H O Me CH.sub.2 4-NO.sub.2535 t-Bu Cl S H O Me CH.sub.2 4-CN536 t-Bu Cl S H O Me CH.sub.2 4-OMe537 t-Bu Cl S H O Me CH.sub.2 4-OEt538 t-Bu Cl S H O Me CH.sub.2 4-SMe539 t-Bu Cl S H O Me CH.sub.2 4-NMe.sub.2540 t-Bu Cl S H O Me CH.sub.2 2-F,4-F541 t-Bu Cl S H O Me CH.sub.2 2-F,6-F542 t-Bu Cl S H O Me CH.sub.2 2-Cl,4-Cl543 t-Bu Cl S H O Me CH.sub.2 2-Cl,6-Cl544 t-Bu Cl S H O Me CH.sub.2 3-Cl,4-Cl545 t-Bu Cl S H O Me CH.sub.2 3-Cl,5-Cl546 t-Bu Cl S H O Me CH.sub.2 2-Cl,4-NO.sub.2547 t-Bu Cl S H O Me CH.sub.2 2-NO.sub.2,4-Cl548 t-Bu Cl S H O Me CH.sub.2 2-Me,4-Me549 t-Bu Cl S H O Me CH.sub.2 2-Me,6-Me550 t-Bu Cl S H O Me CH.sub.2 3-Me,4-Me551 t-Bu Cl S H O Me CH.sub.2 3-Me,5-Me552 t-Bu Cl S H O Me CH.sub.2 3,4-CHCHCHCH553 t-Bu Cl S H O Me CH.sub.2 2-Cl,4-Me554 t-Bu Cl S H O Me CH.sub.2 2-Cl,6-Me555 t-Bu Cl S H O Me CH.sub.2 2-Me,4-Cl556 t-Bu Cl S H O Me CH.sub.2 2-Cl,4-Cl,6-Cl557 t-Bu Cl S H O Me CH.sub.2 2-Me,4-Me,5-Me558 t-Bu Cl S H O Me CH.sub.2 2-Me,4-Me,6-Me559 t-Bu Br S H O Me CH.sub.2 H560 t-Bu OMe S H O Me CH.sub.2 H561 t-Bu SMe S H O Me CH.sub.2 H562 t-Bu Cl S H O i-Pr CH.sub.2 H563 t-Bu Cl S H O Me CHMe H564 t-Bu Cl S H O Me CHMe 4-Cl565 t-Bu Cl S H O Me CHMe 4-Me566 t-Bu Cl S H O Me CHMe 4-OMe567 t-Bu Cl S H O i-Pr CHMe H568 t-Bu Cl S H O i-Pr CHMe 4-Cl569 t-Bu Cl S H O i-Pr CHMe 4-Me570 t-Bu Cl S H O i-Pr CHMe 4-OMe575 t-Bu Cl S H O H OCH.sub.2 H576 t-Bu Cl S H O H OCH.sub.2 4-Cl577 t-Bu Cl S H O H OCH.sub.2 4-Me578 t-Bu Cl S H O H OCH.sub.2 4-OMe579 t-Bu Cl S H O H COCH.sub.2 H583 t-Bu Cl S H O Cl COCH.sub.2 H587 t-Bu Cl S H O Br COCH.sub.2 H589 t-Bu Cl S H O Me COCH.sub.2 H593 t-Bu Cl S H O H CH.sub.2 CH.sub.2 H597 t-Bu Cl S H O Me CH.sub.2 CH.sub.2 H604 t-Bu Cl O H O Cl O H605 t-Bu Cl O H O Cl O 4-Me606 t-Bu Cl O H O Me O H607 t-Bu Cl O H O Me O 4-Cl608 t-Bu Cl O H O Me O 2-Me609 t-Bu Cl O H O Me O 4-Me610 t-Bu Cl O H O Me O 4-Et611 t-Bu Cl O H O Me O 4-t-Bu612 t-Bu Cl O H O Me O 4-OMe613 t-Bu Cl O H O Me O 4-CF.sub.3614 t-Bu Cl O H O Me O 4-NO.sub.2615 t-Bu Cl O H O Me O 4-CN616 t-Bu Cl O H O Me O 4-OCF.sub.3617 t-Bu Cl O H O Me O 2-Cl,4-Cl618 t-Bu Cl O H O Me O 2-Me,4-Me619 t-Bu Cl O H O Me O 2-Cl,4-Cl,6-Cl620 t-Bu Cl O H O Me O 2-Me,4-Me,6-Me623 t-Bu Cl O H O Me S H624 t-Bu Cl O H O Me S 4-F625 t-Bu Cl O H O Me S 4-Cl626 t-Bu Cl O H O Me SO 4-Cl627 t-Bu Cl O H O Me SO.sub.2 4-Cl628 t-Bu Cl O H O Me S 4-Me629 t-Bu Cl O H O Me SO 4-Me630 t-Bu Cl O H O Me SO.sub.2 4-Me633 t-Bu Cl O H O Me NH H634 t-Bu Cl O H O Me NH 4-Cl635 t-Bu Cl O H O Me NH 4-Me636 t-Bu Cl O H O Me NMe H637 t-Bu Cl O H O Me NMe 4-Cl638 t-Bu Cl O H O Me NMe 4-Me642 t-Bu Cl O H O Cl CO H643 t-Bu Cl O H O Cl CO 4-Cl644 t-Bu Cl O H O Cl CO 4-Me645 t-Bu Cl O H O Me CO H646 t-Bu Cl O H O Me CO 2-Cl647 t-Bu Cl O H O Me CO 3-Cl648 t-Bu Cl O H O Me CO 4-Cl649 t-Bu Cl O H O Me CO 2-F650 t-Bu Cl O H O Me CO 4-F651 t-Bu Cl O H O Me CO 2-Br652 t-Bu Cl O H O Me CO 4-Br653 t-Bu Cl O H O Me CO 4-I654 t-Bu Cl O H O Me CO 2-Me655 t-Bu Cl O H O Me CO 3-Me656 t-Bu Cl O H O Me CO 4-Me657 t-Bu Cl O H O Me CO 4-Et658 t-Bu Cl O H O Me CO 4-Bu659 t-Bu Cl O H O Me CO 4-i-Pr660 t-Bu Cl O H O Me CO 4-t-Bu661 t-Bu Cl O H O Me CO 4-CF.sub.3662 t-Bu Cl O H O Me CO 4-NO.sub.2663 t-Bu Cl O H O Me CO 4-CN664 t-Bu Cl O H O Me CO 4-OMe665 t-Bu Cl O H O Me CO 4-OEt666 t-Bu Cl O H O Me CO 4-SMe667 t-Bu Cl O H O Me CO 4-NMe.sub.2668 t-Bu Cl O H O Me CO 2-F,4-F669 t-Bu Cl O H O Me CO 2-F,6-F670 t-Bu Cl O H O Me CO 2-Cl,4-Cl671 t-Bu Cl O H O Me CO 2-Cl,6-Cl672 t-Bu Cl O H O Me CO 3-Cl,4-Cl673 t-Bu Cl O H O Me CO 3-Cl,5-Cl674 t-Bu Cl O H O Me CO 2-Cl,4-NO.sub.2675 t-Bu Cl O H O Me CO 2-NO.sub.2,4-Cl676 t-Bu Cl O H O Me CO 2-Me,4-Me677 t-Bu Cl O H O Me CO 2-Me,6-Me678 t-Bu Cl O H O Me CO 3-Me,4-Me679 t-Bu Cl O H O Me CO 3-Me,5-Me680 t-Bu Cl O H O Me CO 3,4-CHCHCHCH681 t-Bu Cl O H O Me CO 2-Cl,4-Me682 t-Bu Cl O H O Me CO 2-Cl,6-Me683 t-Bu Cl O H O Me CO 2-Me,4-Cl684 t-Bu Cl O H O Me CO 2-Cl,4-Cl,6-Cl685 t-Bu Cl O H O Me CO 2-Me,4-Me,5-Me686 t-Bu Cl O H O Me CO 2-Me,4-Me,6-Me687 t-Bu Br O H O Me CO H688 t-Bu OMe O H O Me CO H689 t-Bu SMe O H O Me CO H690 t-Bu Cl O H O i-Pr CO H694 t-Bu Cl O H O Cl CH.sub.2 H695 t-Bu Cl O H O Cl CH.sub.2 4-Cl696 t-Bu Cl O H O Cl CH.sub.2 4-Me697 t-Bu Cl O H O Me CH.sub.2 H698 t-Bu Cl O H O Me CH.sub.2 2-Cl699 t-Bu Cl O H O Me CH.sub.2 3-Cl700 t-Bu Cl O H O Me CH.sub.2 4-Cl701 t-Bu Cl O H O Me CH.sub.2 2-F702 t-Bu Cl O H O Me CH.sub.2 4-F703 t-Bu Cl O H O Me CH.sub.2 2-Br704 t-Bu Cl O H O Me CH.sub.2 4-Br705 t-Bu Cl O H O Me CH.sub.2 4-I706 t-Bu Cl O H O Me CH.sub.2 2-Me707 t-Bu Cl O H O Me CH.sub.2 3-Me708 t-Bu Cl O H O Me CH.sub.2 4-Me709 t-Bu Cl O H O Me CH.sub.2 4-Et710 t-Bu Cl O H O Me CH.sub.2 4-Bu711 t-Bu Cl O H O Me CH.sub.2 4-i-Pr712 t-Bu Cl O H O Me CH.sub.2 4-t-Bu713 t-Bu Cl O H O Me CH.sub.2 4-CF.sub.3714 t-Bu Cl O H O Me CH.sub.2 4-NO.sub.2715 t-Bu Cl O H O Me CH.sub.2 4-CN716 t-Bu Cl O H O Me CH.sub.2 4-OMe717 t-Bu Cl O H O Me CH.sub.2 4-OEt718 t-Bu Cl O H O Me CH.sub.2 4-SMe719 t-Bu Cl O H O Me CH.sub.2 4-NMe.sub.2720 t-Bu Cl O H O Me CH.sub.2 2-F,4-F721 t-Bu Cl O H O Me CH.sub.2 2-F,6-F722 t-Bu Cl O H O Me CH.sub.2 2-Cl,4-Cl723 t-Bu Cl O H O Me CH.sub.2 2-Cl,6-Cl724 t-Bu Cl O H O Me CH.sub.2 3-Cl,4-Cl725 t-Bu Cl O H O Me CH.sub.2 3-Cl,5-Cl726 t-Bu Cl O H O Me CH.sub.2 2-Cl,4-NO.sub.2727 t-Bu Cl O H O Me CH.sub.2 2-NO.sub.2,4-Cl728 t-Bu Cl O H O Me CH.sub.2 2-Me,4-Me729 t-Bu Cl O H O Me CH.sub.2 2-Me,6-Me730 t-Bu Cl O H O Me CH.sub.2 3-Me,4-Me731 t-Bu Cl O H O Me CH.sub.2 3-Me,5-Me732 t-Bu Cl O H O Me CH.sub.2 3,4-CHCHCHCH733 t-Bu Cl O H O Me CH.sub.2 2-Cl,4-Me734 t-Bu Cl O H O Me CH.sub.2 2-Cl,6-Me735 t-Bu Cl O H O Me CH.sub.2 2-Me,4-Cl736 t-Bu Cl O H O Me CH.sub.2 2-Cl,4-Cl,6-Cl737 t-Bu Cl O H O Me CH.sub.2 2-Me,4-Me,5-Me738 t-Bu Cl O H O Me CH.sub.2 2-Me,4-Me,6-Me739 t-Bu Br O H O Me CH.sub.2 H740 t-Bu OMe O H O Me CH.sub.2 H741 t-Bu SMe O H O Me CH.sub.2 H742 t-Bu Cl O H O i-Pr CH.sub.2 H743 t-Bu Cl O H O Me CHMe H744 t-Bu Cl O H O Me CHMe 4-Cl745 t-Bu Cl O H O Me CHMe 4-Me746 t-Bu Cl O H O Me CHMe 4-OMe747 t-Bu Cl O H O i-Pr CHMe H748 t-Bu Cl O H O i-Pr CHMe 4-Cl749 t-Bu Cl O H O i-Pr CHMe 4-Me750 t-Bu Cl O H O i-Pr CHMe 4-OMe763 t-Bu Cl O H O Cl COCH.sub.2 H767 t-Bu Cl O H O Br COCH.sub.2 H769 t-Bu Cl O H O Me COCH.sub.2 H777 t-Bu Cl O H O Me CH.sub.2 CH.sub.2 H781 t-Bu Cl S H O H CHOH H782 t-Bu Cl S H O H CHOH 4-Cl783 t-Bu Cl S H O Cl CHOH H784 t-Bu Cl S H O Cl CHOH 4-Cl785 t-Bu Cl S H O Me CHOH H786 t-Bu Cl S H O Me CHOH 4-Cl787 t-Bu Cl S H O Me CHOH 4-F788 t-Bu Cl S H O Me CHOH 4-Me789 t-Bu Cl S H O Me CHOH 2-Cl,4-Cl790 t-Bu Cl S H O Me CHOH 2-Me,4-Me791 t-Bu Cl S H O H CHOMe H792 t-Bu Cl S H O H CHOMe 4-Cl793 t-Bu Cl S H O Me CHOMe H794 t-Bu Cl S H O Me CHOMe 4-Cl795 t-Bu Cl S H O Me CHOMe 4-F796 t-Bu Cl S H O Me CHOMe 4-Me797 t-Bu Cl S H O Me CHOMe 2-Cl,4-Cl798 t-Bu Cl S H O Me CHOMe 2-Me,4-Me799 t-Bu Cl S H O Me CHOEt H800 t-Bu Cl S H O Me CHOPr H801 t-Bu Cl S H O H C(OMe).sub.2 H802 t-Bu Cl S H O H C(OMe).sub.2 4-Cl803 t-Bu Cl S H O Cl C(OMe).sub.2 H804 t-Bu Cl S H O Cl C(OMe).sub.2 4-Cl805 t-Bu Cl S H O Me C(OMe).sub.2 H806 t-Bu Cl S H O Me C(OMe).sub.2 4-Cl807 t-Bu Cl S H O Me C(OMe).sub.2 4-F808 t-Bu Cl S H O Me C(OMe).sub.2 4-Me809 t-Bu Cl S H O Me C(OMe).sub.2 2-Cl,4-Cl810 t-Bu Cl S H O Me C(OMe).sub.2 2-Me,4-Me811 t-Bu Cl S H O H CHCl H812 t-Bu Cl S H O H CHCl 4-Cl813 t-Bu Cl S H O Cl CHCl H814 t-Bu Cl S H O Cl CHCl 4-Cl815 t-Bu Cl S H O Me CHCl H816 t-Bu Cl S H O Me CHCl 4-Cl817 t-Bu Cl S H O Me CHCl 4-F818 t-Bu Cl S H O Me CHCl 4-Me819 t-Bu Cl S H O Me CHCl 2-Cl,4-Cl820 t-Bu Cl S H O Me CHCl 2-Me,4-Me__________________________________________________________________________ TABLE 3______________________________________ ##STR9##No. R A X R.sup.1 Y Z.sup.5 Z.sup.6______________________________________841 t-Bu Cl S H O Me CH.sub.2 OH842 t-Bu Cl S H O Me CH(OH)CH.sub.3843 t-Bu Cl S H O Me CH(OH)CH.sub.2 CH.sub.3844 t-Bu Cl S H O Me CH(OH)CH.sub.2 CH.sub.2 CH.sub.3845 t-Bu Cl S H O Me CH.sub.2 CH.sub.2 CH.sub.2 OH846 t-Bu Cl S H O Me CH.sub.2 OCOCH.sub.3847 t-Bu Cl S H O Me CH.sub.2 OCOEt848 t-Bu Cl S H O Me CHMeOCOCH.sub.3849 t-Bu Cl S H O Me CHEtOCOCH.sub.3850 t-Bu Cl S H O Me CH.sub.2 OMe851 t-Bu Cl S H O Me CH.sub.2 OEt852 t-Bu Cl S H O Me CH.sub.2 OPr853 t-Bu Cl S H O Me CH.sub.2 Oi-Pr854 t-Bu Cl S H O Me CHMeOMe855 t-Bu Cl S H O Me CHMeOET856 t-Bu Cl S H O Me CHMeOPr857 t-Bu Cl S H O Me CHEtOMe858 t-Bu Cl S H O Me CHEtOEt859 t-Bu Cl S H O Me C(OMe).sub.2 CH.sub.3860 t-Bu Cl S H O Me C(OEt).sub.2 CH.sub.3861 t-Bu Cl S H O Me C(OMe).sub.2 CH.sub.2 CH.sub.3862 t-Bu Cl S H O Me C(OEt).sub.2 CH.sub.2 CH.sub.3863 t-Bu Cl S H O Me CH.sub.2 SMe864 t-Bu Cl S H O Me CH.sub.2 SEt865 t-Bu Cl S H O Me CH.sub.2 SPr866 t-Bu Cl S H O Me CH.sub.2 S-i-Pr867 t-Bu Cl S H O Me CH.sub.2 SOMe868 t-Bu Cl S H O Me CH.sub.2 SOEt869 t-Bu Cl S H O Me CH.sub.2 SOPr870 t-Bu Cl S H O Me CH.sub.2 SOi-Pr871 t-Bu Cl S H O Me CH.sub.2 SO.sub.2 Me872 t-Bu Cl S H O Me CH.sub.2 SO.sub.2 Et873 t-Bu Cl S H O Me CH.sub.2 SO.sub.2 Pr874 t-Bu Cl S H O Me CH.sub.2 SO.sub.2i-Pr875 t-Bu Cl S H O Me CH.sub.2 NMe.sub.2876 t-Bu Cl S H O Me CH.sub.2 NEt.sub.2877 t-Bu Cl S H O Me CH.sub.2 NPr.sub.2878 t-Bu Cl S H O Me CH.sub.2 COCH.sub.3879 t-Bu Cl S H O Me CH.sub.2 COEt880 t-Bu Cl S H O Me CH.sub.2 COPr881 t-Bu Cl S H O Me CH.sub.2 CH.sub.2 COCH.sub.3882 t-Bu Cl S H O Me CH.sub.2 CH.sub.2 COEt883 t-Bu Cl S H O Me CH.sub.2 CO.sub.2 Me884 t-Bu Cl S H O Me CH.sub.2 CO.sub.2 Et885 t-Bu Cl S H O Me CH.sub.2 CH.sub.2 CO.sub.2 Me886 t-Bu Cl S H O Me CH.sub.2 CH.sub.2 CO.sub.2 Et887 t-Bu Cl S H O Me CH.sub.2 CN888 t-Bu Cl S H O Me CH.sub.2 CH.sub.2 CN889 t-Bu Cl S H O Me CH.sub.2 CH.sub.2 CH.sub.2 CN890 t-Bu Cl S H O Me CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CN891 t-Bu Cl S H O Me CHCNCH.sub.3892 t-Bu Cl S H O Me CHCNCH.sub.2 CH.sub.3893 t-Bu Cl S H O Me CHCNCH.sub.2 CH.sub.2 CH.sub.3894 t-Bu Cl S H O Me CHNOMe895 t-Bu Cl S H O Me CMeNOMe896 t-Bu Cl S H O Me CMeNOEt897 t-Bu Cl S H O Me CEtNOMe898 t-Bu Cl S H O Me CEtNOEt899 t-Bu Cl S H O Cl CH.sub.2 OMe900 t-Bu Cl S H O Cl CH.sub.2 OEt901 t-Bu Cl S H O Me OCH.sub.2 OMe902 t-Bu Cl S H O Me OCH.sub.2 OEt903 t-Bu Cl S H O Me OCH.sub.2 OPr904 t-Bu Cl S H O Me OCH.sub.2 Oi-Pr905 t-Bu Cl S H O Me OCH.sub.2 CH.sub.2 OMe906 t-Bu Cl S H O Me OCH.sub.2 CH.sub.2 OEt907 t-Bu Cl S H O Me OCH.sub.2 CH.sub.2 OPr908 t-Bu Cl S H O Me OCH.sub.2 CH.sub.2 Oi-Pr909 t-Bu Cl S H O Me OCH.sub.2 SMe910 t-Bu Cl S H O Me OCH.sub.2 SEt911 t-Bu Cl S H O Me OCH.sub.2 CH.sub.2 SMe912 t-Bu Cl S H O Me OCH.sub.2 CH.sub.2 SEt913 t-Bu Cl S H O Me OCH.sub.2 SOMe914 t-Bu Cl S H O Me OCH.sub.2 SO.sub.2 Me915 t-Bu Cl S H O Me OCH.sub.2 CH.sub.2 SOMe916 t-Bu Cl S H O Me OCH.sub.2 CH.sub.2 SO.sub.2 Me917 t-Bu Cl S H O Me OCH.sub.2 NMe.sub.2918 t-Bu Cl S H O Me OCH.sub.2 CH.sub.2 NMe.sub.2919 t-Bu Cl S H O Me OCH.sub.2 COCH.sub.3920 t-Bu Cl S H O Me OCH.sub.2 COEt921 t-Bu Cl S H O Me OCH.sub.2 CH.sub.2 COCH.sub.3922 t-Bu Cl S H O Me OCH.sub.2 CH.sub.2 COEt923 t-Bu Cl S H O Me OCH.sub.2 CO.sub.2 Me924 t-Bu Cl S H O Me OCH.sub.2 CO.sub.2 Et925 t-Bu Cl S H O Me OCH.sub.2 CH.sub.2 CO.sub.2 Me926 t-Bu Cl S H O Me OCH.sub.2 CH.sub.2 CO.sub.2 Et927 t-Bu Cl S H O Me OCH.sub.2 CN928 t-Bu Cl S H O Me OCH.sub.2 CH.sub.2 CN929 t-Bu Cl S H O H OCH.sub.2 OMe930 t-Bu Cl S H O H OCH.sub.2 OEt931 t-Bu Cl S H O Me COCH.sub.2 F932 t-Bu Cl S H O Me COCH.sub.2 Cl933 t-Bu Cl S H O Me COCH.sub.2 Br934 t-Bu Cl S H O Me COCF.sub.3935 t-Bu Cl S H O Me COCHClCH.sub.3936 t-Bu Cl S H O Me COCHBrCH.sub.3937 t-Bu Cl S H O Me COCH.sub.2 CF.sub.3938 t-Bu Cl S H O Me COCH.sub.2 CH.sub.2 F939 t-Bu Cl S H O Me COCH.sub.2 CH.sub.2 Cl940 t-Bu Cl S H O Me COCH.sub.2 CH.sub.2 Br941 t-Bu Cl S H O Me COCH.sub.2 OMe942 t-Bu Cl S H O Me COCH.sub.2 OEt943 t-Bu Cl S H O Me COCH.sub.2 OPr944 t-Bu Cl S H O Me COCHMeOMe945 t-Bu Cl S H O Me COCHMeOEt946 t-Bu Cl S H O Me COCH.sub.2 CH.sub.2 OMe947 t-Bu Cl S H O Me COCH.sub.2 CH.sub.2 OEt948 t-Bu Cl S H O Me COCH.sub.2 SMe949 t-Bu Cl S H O Me COCH.sub.2 SEt950 t-Bu Cl S H O Me COCH.sub.2 SPr951 t-Bu Cl S H O Me COCHMeSMe952 t-Bu Cl S H O Me COCHMeSEt953 t-Bu Cl S H O Me COCH.sub.2 CH.sub.2 SMe954 t-Bu Cl S H O Me COCH.sub.2 CH.sub.2 SEt955 t-Bu Cl S H O Me COCH.sub.2 SOMe956 t-Bu Cl S H O Me COCH.sub.2 SOEt957 t-Bu Cl S H O Me COCH.sub.2 CH.sub.2 SOMe958 t-Bu Cl S H O Me COCH.sub.2 SO.sub.2 Me959 t-Bu Cl S H O Me COCH.sub.2 SO.sub.2 Et960 t-Bu Cl S H O Me COCH.sub.2 CH.sub.2 SO.sub.2 Me961 t-Bu Cl S H O Me COCH.sub.2 NMe.sub.2962 t-Bu Cl S H O Me COCH.sub.2 NEt.sub.2963 t-Bu Cl S H O Me COCH.sub.2 CH.sub.2 NMe.sub.2964 t-Bu Cl S H O Me COCH.sub.2 CH.sub.2 NEt.sub.2965 t-Bu Cl S H O Me COCH.sub.2 COCH.sub.3966 t-Bu Cl S H O Me COCH.sub.2 CO.sub.2 Me967 t-Bu Cl S H O Me COCH.sub.2 CO.sub.2 Et968 t-Bu Cl S H O Me COCH.sub.2 CH.sub.2 CO.sub.2 Me969 t-Bu Cl S H O Me COCH.sub.2 CH.sub.2 CO.sub.2 Et970 t-Bu Cl S H O Me COCH.sub.2 CN971 t-Bu Cl S H O Me COCH.sub.2 CH.sub.2 CN972 t-Bu Cl S H O Me COCHMeCN973 t-Bu Cl S H O H COCH.sub.2 Cl974 t-Bu Cl S H O H COCH.sub.2 Br975 t-Bu Cl S H O H COCH.sub.2 F976 t-Bu Cl S H O H COCH.sub.2 CH.sub.2 Cl977 t-Bu Cl S H O H COCH.sub.2 CH.sub.2 F978 t-Bu Cl S H O H COCH.sub.2 OMe979 t-Bu Cl S H O H COCH.sub.2 OEt980 t-Bu Cl S H O H COCH.sub.2 OPr981 t-Bu Cl S H O H COCH.sub.2 SMe982 t-Bu Cl S H O Cl COCH.sub.2 Cl983 t-Bu Cl S H O Cl COCH.sub.2 Br984 t-Bu Cl S H O Cl COCH.sub.2 F985 t-Bu Cl S H O Cl COCH.sub.2 CH.sub.2 Cl986 t-Bu Cl S H O Cl COCH.sub.2 CH.sub.2 F987 t-Bu Cl S H O Cl COCH.sub.2 OMe988 t-Bu Cl S H O Cl COCH.sub.2 OEt989 t-Bu Cl S H O Cl COCH.sub.2 OPr990 t-Bu Cl S H O Cl COCH.sub.2 SMe991 t-Bu Cl O H O Me CH.sub.2 OH992 t-Bu Cl O H O Me CH(OH)CH.sub.3993 t-Bu Cl O H O Me CH(OH)CH.sub.2 CH.sub.3994 t-Bu Cl O H O Me CH(OH)CH.sub.2 CH.sub.2 CH.sub.3995 t-Bu Cl O H O Me CH.sub.2 CH.sub.2 CH.sub.2 OH996 t-Bu Cl O H O Me CH.sub.2 OCOCH.sub.3997 t-Bu Cl O H O Me CH.sub.2 OCOEt998 t-Bu Cl O H O Me CHMeOCOCH.sub.3999 t-Bu Cl O H O Me CHEtOCOCH.sub.31000 t-Bu Cl O H O Me CH.sub.2 OMe1001 t-Bu Cl O H O Me CH.sub.2 OEt1002 t-Bu Cl O H O Me CH.sub.2 OPr1003 t-Bu Cl O H O Me CH.sub.2 Oi-Pr1004 t-Bu Cl O H O Me CHMeOMe1005 t-Bu Cl O H O Me CHMeOEt1006 t-Bu Cl O H O Me CHMeOPr1007 t-Bu Cl O H O Me CHEtOMe1008 t-Bu Cl O H O Me CHEtOEt1009 t-Bu Cl O H O Me C(OMe).sub.2 CH.sub.31010 t-Bu Cl O H O Me C(OEt).sub.2 CH.sub.31011 t-Bu Cl O H O Me C(OMe).sub.2 CH.sub.2 CH.sub.31012 t-Bu Cl O H O Me C(OEt).sub.2 CH.sub.2 CH.sub.31013 t-Bu Cl O H O Me CH.sub.2 SMe1014 t-Bu Cl O H O Me CH.sub.2 SEt1015 t-Bu Cl O H O Me CH.sub.2 SPr1016 t-Bu Cl O H O Me CH.sub.2 S-i-Pr1017 t-Bu Cl O H O Me CH.sub.2 SOMe1018 t-Bu Cl O H O Me CH.sub.2 SOEt1019 t-Bu Cl O H O Me CH.sub.2 SOPr1020 t-Bu Cl O H O Me CH.sub.2 SOi-Pr1021 t-Bu Cl O H O Me CH.sub.2 SO.sub.2 Me1022 t-Bu Cl O H O Me CH.sub.2 SO.sub.2 Et1023 t-Bu Cl O H O Me CH.sub.2 SO.sub.2 Pr1024 t-Bu Cl O H O Me CH.sub.2 SO.sub.2i-Pr1025 t-Bu Cl O H O Me CH.sub.2 NMe.sub.21026 t-Bu Cl O H O Me CH.sub.2 NEt.sub.21027 t-Bu Cl O H O Me CH.sub.2 NPr.sub.21028 t-Bu Cl O H O Me CH.sub.2 COCH.sub.31029 t-Bu Cl O H O Me CH.sub.2 COEt1030 t-Bu Cl O H O Me CH.sub.2 COPr1031 t-Bu Cl O H O Me CH.sub.2 CH.sub.2 COCH.sub.31032 t-Bu Cl O H O Me CH.sub.2 CH.sub.2 COEt1033 t-Bu Cl O H O Me CH.sub.2 CO.sub.2 Me1034 t-Bu Cl O H O Me CH.sub.2 SO.sub.2 Et1035 t-Bu Cl O H O Me CH.sub.2 CH.sub. 2 CO.sub.2 Me1036 t-Bu Cl O H O Me CH.sub.2 CH.sub.2 CO.sub.2 Et1037 t-Bu Cl O H O Me CH.sub.2 CN1038 t-Bu Cl O H O Me CH.sub.2 CH.sub.2 CN1039 t-Bu Cl O H O Me CH.sub.2 CH.sub.2 CH.sub.2 CN1040 t-Bu Cl O H O Me CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CN1041 t-Bu Cl O H O Me CHCNCH.sub.31042 t-Bu Cl O H O Me CHCNCH.sub.2 CH.sub.31043 t-Bu Cl O H O Me CHCNCH.sub.2 CH.sub.2 CH.sub.31044 t-Bu Cl O H O Me CHNOMe1045 t-Bu Cl O H O Me CMeNOMe1046 t-Bu Cl O H O Me CMeNOEt1047 t-Bu Cl O H O Me CEtNOMe1048 t-Bu Cl O H O Me CEtNOEt1049 t-Bu Cl O H O Cl CH.sub.2 OMe1050 t-Bu Cl O H O Cl CH.sub.2 OEt1051 t-Bu Cl O H O Me OCH.sub.2 OMe1052 t-Bu Cl O H O Me OCH.sub.2 OEt1053 t-Bu Cl O H O Me OCH.sub.2 OPr1054 t-Bu Cl O H O Me OCH.sub.2 Oi-Pr1055 t-Bu Cl O H O Me OCH.sub.2 CH.sub.2 OMe1056 t-Bu Cl O H O Me OCH.sub.2 CH.sub.2 OEt1057 t-Bu Cl O H O Me OCH.sub.2 CH.sub.2 OPr1058 t-Bu Cl O H O Me OCH.sub.2 CH.sub.2 Oi-Pr1059 t-Bu Cl O H O Me OCH.sub.2 SMe1060 t-Bu Cl O H O Me OCH.sub.2 SEt1061 t-Bu Cl O H O Me OCH.sub.2 CH.sub.2 SMe1062 t-Bu Cl O H O Me OCH.sub.2 CH.sub.2 SEt1063 t-Bu Cl O H O Me OCH.sub.2 SOMe1064 t-Bu Cl O H O Me OCH.sub.2 SO.sub.2 Me1065 t-Bu Cl O H O Me OCH.sub.2 CH.sub.2 SOMe1066 t-Bu Cl O H O Me OCH.sub.2 CH.sub.2 SO.sub.2 Me1067 t-Bu Cl O H O Me OCH.sub.2 NMe.sub.21068 t-Bu Cl O H O Me OCH.sub.2 CH.sub.2 NMe.sub.21069 t-Bu Cl O H O Me OCH.sub.2 COCH.sub.31070 t-Bu Cl O H O Me OCH.sub.2 COEt1071 t-Bu Cl O H O Me OCH.sub.2 CH.sub.2 COCH.sub.31072 t-Bu Cl O H O Me OCH.sub.2 CH.sub.2 COEt1073 t-Bu Cl O H O Me OCH.sub.2 CO.sub.2 Me1074 t-Bu Cl O H O Me OCH.sub.2 CO.sub.2 Et1075 t-Bu Cl O H O Me OCH.sub.2 CH.sub.2 CO.sub.2 Me1076 t-Bu Cl O H O Me OCH.sub.2 CH.sub.2 CO.sub.2 Et1077 t-Bu Cl O H O Me OCH.sub.2 CN1078 t-Bu Cl O H O Me OCH.sub.2 CH.sub.2 CN1081 t-Bu Cl O H O Me COCH.sub.2 F1082 t-Bu Cl O H O Me COCH.sub.2 Cl1083 t-Bu Cl O H O Me COCH.sub.2 Br1084 t-Bu Cl O H O Me COCF.sub.31085 t-Bu Cl O H O Me COCHClCH.sub.31086 t-Bu Cl O H O Me COCHBrCH.sub.31087 t-Bu Cl O H O Me COCH.sub.2 CF.sub.31088 t-Bu Cl O H O Me COCH.sub.2 CH.sub.2 F1089 t-Bu Cl O H O Me COCH.sub.2 CH.sub.2 Cl1090 t-Bu Cl O H O Me COCH.sub.2 CH.sub.2 Br1091 t-Bu Cl O H O Me COCH.sub.2 OMe1092 t-Bu Cl O H O Me COCH.sub.2 OEt1093 t-Bu Cl O H O Me COCH.sub.2 OPr1094 t-Bu Cl O H O Me COCHMeOMe1095 t-Bu Cl O H O Me COCHMeOEt1096 t-Bu Cl O H O Me COCH.sub.2 CH.sub.2 OMe1097 t-Bu Cl O H O Me COCH.sub.2 CH.sub.2 OEt1098 t-Bu Cl O H O Me COCH.sub.2 SMe1099 t-Bu Cl O H O Me COCH.sub.2 SEt1100 t-Bu Cl O H O Me COCH.sub.2 SPr1101 t-Bu Cl O H O Me COCHMeSMe1102 t-Bu Cl O H O Me COCHMeSEt1103 t-Bu Cl O H O Me COCH.sub.2 CH.sub.2 SMe1104 t-Bu Cl O H O Me COCH.sub.2 CH.sub.2 SEt1105 t-Bu Cl O H O Me COCH.sub.2 SOMe1106 t-Bu Cl O H O Me COCH.sub.2 SOEt1107 t-Bu Cl O H O Me COCH.sub.2 CH.sub.2 SOMe1108 t-Bu Cl O H O Me COCH.sub.2 SO.sub.2 Me1109 t-Bu Cl O H O Me COCH.sub.2 SO.sub.2 Et1110 t-Bu Cl O H O Me COCH.sub.2 CH.sub.2 SO.sub.2 Me1111 t-Bu Cl O H O Me COCH.sub.2 NMe.sub.21112 t-Bu Cl O H O Me COCH.sub.2 NEt.sub.21113 t-Bu Cl O H O Me COCH.sub.2 CH.sub.2 NMe.sub.21114 t-Bu Cl O H O Me COCH.sub.2 CH.sub.2 NEt.sub.21115 t-Bu Cl O H O Me COCH.sub.2 COCH.sub.31116 t-Bu Cl O H O Me COCH.sub.2 CO.sub.2 Me1117 t-Bu Cl O H O Me COCH.sub.2 CO.sub.2 Et1118 t-Bu Cl O H O Me COCH.sub.2 CH.sub.2 CO.sub.2 Me1119 t-Bu Cl O H O Me COCH.sub.2 CH.sub.2 CO.sub.2 Et1120 t-Bu Cl O H O Me COCH.sub.2 CN1121 t-Bu Cl O H O Me COCH.sub.2 CH.sub.2 CN1122 t-Bu Cl O H O Me COCHMeCN1132 t-Bu Cl O H O Cl COCH.sub.2 Cl1133 t-Bu Cl O H O Cl COCH.sub.2 Br1134 t-Bu Cl O H O Cl COCH.sub.2 F1135 t-Bu Cl O H O Cl COCH.sub.2 CH.sub.2 Cl1136 t-Bu Cl O H O Cl COCH.sub.2 CH.sub.2 F1137 t-Bu Cl O H O Cl COCH.sub.2 OMe1138 t-Bu Cl O H O Cl COCH.sub.2 OEt1139 t-Bu Cl O H O Cl COCH.sub.2 OPr1140 t-Bu Cl O H O Cl COCH.sub.2 SMe1141 t-Bu Cl S H O Me NHSO.sub.2 Me1142 t-Bu Cl S H O Me NHCONMe.sub.21143 t-Bu Cl S H O Me C(Me)NNMe.sub.2______________________________________

Preferred compounds according to the present invention include:

2-t-butyl-4-chloro-5-[2-2,6-dimethyl-4-(4-methylphenoxy)phenoxy ethylthio]-3(2H)-pyridazinone of claim 1 having the formula: ##STR10##

2-t-butyl-4-chloro-5-[2-(2,6-dimethyl-4-phenoxyphenoxy)ethylthio]-3(2H)-pyridazinone of claim 1 having the formula: ##STR11##

2-t-butyl-4-chloro-5-[2-{2,6-dimethyl-4-(2,4-difluorobenzoyl)phenoxy}ethylthio]-3(2H)-pyridazinone of claim 1 having the formula: ##STR12##

2-t-butyl-4-chloro-5-[2-(2,6-dimethyl-4-ethoxyphenoxy)ethylthio]-3(2H)-pyridazinone of claim 1 having the formula: ##STR13##

2-t-butyl-4-chloro-5-[2-(2,6-dimethyl-4-methoxy-methylphenoxy)ethylthio]-3(2H)-pyridazinone of claim 1 having the formula: ##STR14##

The compound numbers in Tables 1 to 3 are referred to in preparation examples, formulation examples and test examples, which will be mentioned below.

The compounds of the present invention can be prepared by reacting a compound of the general formula (II): ##STR15## with a compound of the general formula (III): ##STR16## wherein R, A, R.sup.1, Y, and Z.sup.1 -Z.sup.4 have the same meanings as defined above, and X' and X" represent halogen atom, --SM or --OM in which M means hydrogen atom or alkali metal atom.

In general, it is preferable to use --SM or --OM as X" in the general formula (III) when X' in the general formula (II) is halogen atom, and to use halogen atom as X" in the general formula (III) when X' in the general formula (II) is --SM or --OM (wherein M represents hydrogen atom or alkali metal atom), with the proviso that when X' is halogen atom, X" represents --Sm or --OM, and when X' is --SM or --OM, X" represents halogen atom.

It is also preferable to prepare the compounds of the present invention in the presence of appropriate bases and in solvents which do not affect the reaction. When M is alkali metal atom, the presence of the base is not necessarily needed.

As the solvents in the present invention can be used lower alcohols such as methanol, ethanol, etc.; ketones such as acetone, methylethylketone, etc.; hydrocarbons such as benzene, toluene, etc.; ethers such as isopropylether, tetrahydrofuran, 1,4-dioxane, etc.; amides such as N,N-dimethylformamide, hexamethyl phosphoric triamides, etc.; halogenated hydrocarbons such as dichloromethane, dichloroethane, etc. As necessary, mixtures of these solvens or mixtures of these solvents and water can also be used.

Inorganic bases such as sodium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen-carbonate, etc., and organic bases such as sodium methoxide, sodium ethoxide, triethylamine, pyridine, etc. can be used as the base. If necessary, tetraammonium salts, for example, triethylbenzylammonium chloride, etc., may be added to the reaction system as catalyst.

The reaction temperature may be in a range of from -20.degree. C. to the boiling point of the solvent to be used in the reaction. The reaction temperature is preferably in a range of from -5.degree. C. to the boiling point of the solvent to be used in the reaction.

The ratio of the raw material can be optionally selected, but it is advantageous to conduct the reaction using equimolar or nearly equimolar amount of the materials.

Preparation of compounds of the present invention is described in more detail by the way of the following examples which are not to restrict to the invention.

PREPARATION EXAMPLE 1

Preparation of 2-t-butyl-4-chloro-5-(2'-[2",6"-dimethylphenoxy) ethylthio]-3-(2H)-pyridazinone (Compound No. 24)

In 30 mm of N,N-dimethylformamide was dissolved 2.2 g of 2-t-butyl-4-chloro-5-mercapto-3(2H)-pyridazinone and 2.3 g of 2-(2',6'-dimethylphenoxy)ethyl bromide, and thereto were added 1.1 g of anhydrous sodium carbonate. The resulting solution was stirred at room temperature for fifteen hours. This solution was poured into water and extracted with diethyl ether. The organic layer was dried over anhydrous sodium sulfate and freed of solvent under reduced pressure to give crystals. The crystals thus obtained were washed with n-hexane to give 3.5 g of the intended compound. m.p. 104.3.degree..about.105.2.degree. C.

PREPARATION EXAMPLE 2

Preparation of 2-t-butyl-4-chloro-5-(2'-[2",6"-dimethyl-4"-butylcarbonylphenoxy)ethylthio]-3-(2H)-pyridazinone (Compound No. 78)

In 30 mm of N,N-dimethylformamide was dissolved 2.2 g of 2-t-butyl-4-chloro-5-mercapto-3(2H)-pyridazinone and 3.0 g of 2-(2',6'-dimethyl-4'butylcarbonylphenoxyethyl bromide and thereto were added 1.5 g of anhydrous sodium carbonate. The resulting solution was stirred at room temperature for fifteen hours. This solution was poured into water and extracted with diethyl ether. The organic layer was dried over anhydrous sodium sulfate and freed of solvent under reduced pressure to give a crude product. The crude product thus obtained was purified by means of column chromatography (on silica gel, eluting with benzene) to give 3.3 g of the intended compound as an oil.

PREPARATION EXAMPLE 3

Preparation of 2-t-butyl-4-chloro-5-[2'-(2",6"-dimethyl-4"-benzoylphenoxy)ethylthio]-3-(2H)-pyridazinone (Compound No. 465)

In 50 ml of N,N-dimethylformamide were dissolved 6.6 g of 2-t-butyl-4-chloro-5-mercapto-3(2H)-pyridazinone and 10 g of 2-(2',6'-dimethyl-4'-benzoylphenoxy)ethyl bromide, and thereto was added 5 g of anhydrous sodium carbonate. The solution was stirred at room temperature for seventeen hours. The resulting solution was poured into water and extracted with diethyl ether. The organic layer was dried over anhydrous sodium sulfate and freed of solvent by distillation under reduced pressure to give a crude product. The crude product thus obtained was purified by means of column chromatography (on silica gel, eluting with benzene) and crystallization (from 50 ml of n-hexanediethyl ether (4:1)) to give 13.3 g of the intended compound. m.p. 94.6.degree..about.96.2.degree. C.

PREPARATION EXAMPLE 4

Preparation of 2-t-butyl-4-chloro-5-[2{-2,6-dimethyl-4-(4-methylphenoxy)phenoxy}ethylthio]-3(2H)-pyridazinone (Compound No. 429).

In 10 ml of N,N-dimethylformamide were dissolved 1.5 g of 2-t-butyl-4-chloro-5-mercapt-3(2H)-pyridazinone and 2.3 g of 2-{2,6-dimethyl-4-(4-methylphenoxy)phenoxy}ethylbromide, and thereto was added 1.0 g of anhydrous sodium carbonate. The mixture was stirred for 15 hours at room temperature. The resulting solution was poured into water (50 ml) and then extracted with 50 ml of diethyl ether and further with 50 ml of ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate and freed of solvent by distillation under reduced pressure to give 3.2 g of a crude product. The crude product was recrystallized from benzenehexane (1:3)(20 ml) to obtain 2.5 g of the intended compound. m.p.: 137.7.degree.-140.7.degree. C.

The physical properties of the compounds prepared according to one of the methods of the Preparation Examples 1 to 4 are shown in the following Table 4.

TABLE 4______________________________________No. m.p. (.degree.C.) No. m.p. (.degree.C.)______________________________________12 109.2-111.6 56 86.4-91.513 oil 61 109.7-112.014 oil 70 oil15 oil 71 152.9-153.716 61.0-63.0 72 116.9-118.217 65.0-70.0 73 106.9-108.618 oil 74 127.9-130.119 oil 75 126.1-129.221 87.0-88.5 76 oil22 96.8-98.5 77 152.7-156.423 112.4-113.3 78 oil24 104.3-105.2 79 oil25 oil 80 oil26 78.3-80.7 82 107.0-108.827 98.6-102.1 84 79.7-80.828 oil 85 90.0-91.529 oil 87 oil30 oil 88 103.5-104.831 95.7-98.0 89 119.8-124.532 109.0-111.2 90 oil33 106.6-109.2 92 117.2-120.134 95.4-97.0 93 oil36 oil 94 108.2-109.238 123.4-127.3 95 oil40 94.0-96.0 97 oil41 oil 98 oil44 oil 99 oil45 oil 112 107.7-108.346 115.0-118.1 113 86.2-88.549 oil 148 oil53 oil 150 oil55 92.8-93.6 151 88.0-89.0 161 55.0-60.0 270 156.0-160.5174 oil 271 116.1-117.6202 85.0-87.0 272 159.9-161.3219 126.5-127.7 273 122.0-124.8223 111.1-113.5 275 98.1-104.2224 97.0-101.0 277 143.1-145.6225 oil 279 107.6-109.5226 124.6-129.5 280 102.8-106.5227 135.6-139.2 283 86.7-88.1228 131.1-132.6 284 108.8-110.5229 133.2-134.7 285 94.5-100.0230 120.0-124.0 287 173.3-176.3232 79.0-80.3 288 86.6-87.9233 142.5-146.5 289 147.1-148.3235 85.0-87.0 290 73.1-75.5236 96.0-98.0 292 oil239 155.7-157.4 293 64.1-64.2240 oil 294 103.4-104.4241 108.2-111.8 343 96.1-97.3248 149.5-151.2 344 117.9-120.9250 137.9-139.2 360 oil251 88.0-93.0 421 120.3-128.2256 130.6-134.1 463 150.2-151.8265 112.9-114.5 465 94.6-96.2266 171.0-173.8 466 156.9-158.1267 150.6-152.9 467 oil268 131.5-133.5 468 142.2-144.1269 135.2-137.8 470 oil472 153.1-154.5 656 113.0-116.0474 129.2-131.4 660 143.9-145.6475 oil 662 193.0-196.0476 oil 664 168.6-170.9480 138.0-140.0 670 153.0-154.3482 162.0-164.6 672 143.0-144.8484 125.1-126.4 673 177.5-179.0490 108.9-111.2 676 122.7-123.4492 126.5- 128.0 678 157.6-159.1493 158.7-161.3 680 137.1-138.1494 134.4-135.4 694 139.2-140.4496 121.7-122.5 697 163.4-165.0498 113.8-115.9 698 179.8-182.2500 135.3-137.3 699 116.7-117.7514 oil 722 58.0-62.0517 123.1-126.1 725 130.0-131.0518 136.4-137.5 111 91.1-92.1519 98.3-99.2 491 212.6-213.6520 oil 477 116.6-118.6527 105.9-107.6 306 125.9-127.6542 115.2-116.4 671 224.5-226.5545 130.7-132.5 657 137.6-139.1643 156.8-158.0 152 98.9-101.5646 202.3-204.0 489 161.0-163.6647 135.8-137.8 83 121.0-122.0652 163.9-166.0 278 142.7-144.7654 168.9-170.1 153 87.5-90.0655 134.1-135.9198 93.3-94.8 609 153.1-157.0100 104.7-106.7 610 134.0-136.0102 135.4-136.5 612 180.0-183.0127 119.0-120.6 618 126.9-128.9128 93.2-95.2 661 165.0-167.0129 74.8-76.5 668 145.8-146.7131 118.5-121.3 702 57.0-60.0134 141.9-142.7 704 98.8-101.1135 125.3-127.4 708 143.7-145.3199 70.4-71.2 720 118.5-120.1296 166.8-167.8 843 147.8-150.4323 105.0-107.2 850 67.0-70.0324 81.1-83.6 851 oil426 119.3-120.4 852 oil427 102.2-102.9 857 oil429 137.7-140.7 863 oil430 95.3-98.0 895 106.7-109.2432 112.8-113.4 1000 105.0-107.0438 102.2-102.9 1001 103.7-105.7443 120.0-123.2 1002 94.3-96.7481 142.4-143.5 1045 141.5-143.1488 123.8-124.9 1141 216.0-218.0522 oil 1142 173.6-175.8524 oil 1143 121.4-124.1528 103.4-104.5 589 oil540 93.0-94.1 597 oil606 167.5-170.3 777 101.5-105.6______________________________________

When the compounds according to the present invention are used for insecticidal, acaricidal and/or nematicidal agents for agricultural and horticultural uses or for expellents of ticks parasitic on animals, they are generally mixed with appropriate carriers, for instance, solid carriers such as clay, talc, bentonite or diatomaceous earth, or liquid carriers such as water, alcohols (e.g., methanol and ethanol), aromatic hydrocarbons (e.g., benzene, toluene and xylene), chlorinated hydrocarbons, ethers, ketones, acid amides (e.g., dimethylformamide (DMF)) or esters (e.g., ethyl acetate). If desired, to these mixtures can be added a surfactant, eumulsifier, dispersing agent, suspending agent, penetrating agent, spreader, stabilizer and the like to put them into practical uses in the form of liquid preparation, smulsifiable concentration, wettable powder, dust, granule, flowable or the like. Moreover, the resulting mixtures may be incorporated with other herbicides, various insecticides, plant-growth regulating agents and/or synergists during preparation or application thereof, as necessary.

When the present compounds are used in the agricultural and horticultural fields, the amount to be applied as an active ingredient is in the range of 0.005 to 50 kg per hectare. It is more preferable to apply 0.01 to 5 kg/hectare.

When the present compounds are used for controlling ectoparasites on animals, in general, diluted aqueous solution of 2 to 50,000 ppm can be used as concentration of active ingredient, more preferably 10 to 1,000 ppm.

In the following, there are shown component ratios of formulations and formulation examples of insecticidal, acaricidal and/or nematicidal compositions and expellent compositions for ticks parasitic on animals, said compositions containing the compounds of the present invention as active ingredients. These examples are merely illustrative and not to restrict the invention. In the following examples, "part" means "part by weight" and "%" means "% by weight".

1. Components Ratio of Formulation

(1) Emulsifiable concentrates

______________________________________Active ingredient: 5-25%liquid carrier: 52-90% (Xylene, DMF, Methyl naphthalene, Cyclo- hexanone, Dichloro- benzene, Isophorone)surface active agent: 5-20% (Sorpol 2680, Sorpol 3005X, Sorpol 3346)others: 0-20% (Piperonyl butoxide: 0-20% Benzotriazole: 0-5%)______________________________________

(2) Oil solutions

______________________________________Active ingredient: 5-30%liquid carrier: 70-95% (Xylene, Methyl cellosolve, Kerosene)______________________________________

(3) Flowables

______________________________________Active ingredient: 5-70%liquid carrier: 12.4-78.4% (water)surface active agent: 1-10.5% (Lunox 1000C, Sorpol 3353, Soprophor FL, Nippol, Agrisol S-710, Lignin sulfonic acid soda)others: 0-10% Formalin 0-0.3%, Ethylene glycol 0-10%, Propylene glycol 0-10%)______________________________________

(4) Wettable powders (W.P.)

______________________________________Active ingredient: 5-70%Solid carrier: 15-89% (Calcium carbonate, Kaolinite, Zeeklite D, Zeeklite PFP, Diatomaceous earth, Talc)surface active agent: 3-10% (Sorpol 5039, Lunox 1000C, Sulfonic acid calcium, Sodium dodecyl-sulfonate, Sorpol 5050, Sorpol 005D, Sorpol 5029-O)______________________________________

(5) Dusts

______________________________________Active ingredient: 0.01-30%solid carrier: 67-99% (Calcium carbonate, Kaolinite, Zeeklite, Talc)others: 0-3% (Diisopropylphos- phate 0-1.5%, Carplex #80: 0-3%)______________________________________

(6) Granules

______________________________________Active ingredient: 0.1-30%solid carrier: 67-99% (Calcium carbonate, Kaolinite, Talc, Bentonite)others: 0-8% (Calcium lignin sulfonate: 0-3 wt %, Polyvinylalcohol: 0-5%)______________________________________

2. Formulation Examples

Formulation Example 1: Emulsifiable concentrates

______________________________________Active ingredient 20 partsXylene 55 partsN,N--dimethylformamide 20 partsSolpol 2680 (trade name, a mixture of 5 partsa non-ionic surface-active agent andan anionic surface-active agentmanufactured by Toho Chemicals, Co.,Ltd., Japan)______________________________________

The above components are mixed intimately together to form an emulsifiable concentrate. Upon use, the emulsifiable concentrate is diluted with water up to one fiftieth to one twenty thousandth in concentration and applied at a rate of 0.005 to 50 kg of the active ingredient per hectare.

Formulation Example 2: Wettable powders

______________________________________Active ingredient 25 partsZeeklite PFP (trade name, a mixture of 66 partskaolinite and sericite manufacturedby Zeeklite Mining Industries Co., Ltd.)Solpol 5039 4 parts(trade name, an anioic surface-activeagent manufactured by Toho ChemicalCo., Ltd., Japan)Carplex #80 3 parts(trade name, white carbon manufacturedby Shionogi Seiyaku K.K., Japan)Calcium lingin sulfonate 2 parts______________________________________

The above components are homogeneously mixed together and ground to form a wettable powder. Upon use, the wettable powder is diluted with water up to one fiftieth to one twenty thousandth and applied at a rate of 0.005 to 50 kg of the active ingredient per hectare.

Formulation Example 3: Oil solutions

______________________________________Active ingredient 10 partsmethylcellosolve 90 parts______________________________________

The above components are homogeneously mixed together to form an oil solution. Upon use, the oil solution is applied at a rate of 0.005 to 50 kg of the active ingredient per hectare.

Formulation Example 4: Dusts

______________________________________Active ingredient 3.0 partsCarplex #80 (trade name, white carbon 0.5 partsmanufactured by Shionogi SeiyakuK.K., Japan)Clay 95.0 partsdi-isopropyl phosphate 1.5 parts______________________________________

The above components are homogeneously mixed together and ground to form a dust. Upon use, the dust is applied at a rate of 0.005 to 50 kg of the active ingredient per hectare.

Formulation Example 5: Granules

______________________________________Active ingredient 5 partsBentonite 54 partsTalc 40 partsCalcium lignin sulfonate 1 part______________________________________

The above components are mixed intimately together and ground, incorporated with a small amount of water and mixed together with stirring. The resulting mixture is granulated by means of extrusion-granulator and dried to form granules. Upon use, the granule is applied at a rate of 0.005 to 50 kg of the active ingredient per hectare.

Formulation Example 6: Flowables

______________________________________Active ingredient 25 partsSolpol 3353 (trade name, a nonionic 10 partssurface-active agent manufacturedby Toho Chemical Co., Ltd., Japan)Runox 1000C (trade name, an anionic 0.5 partssurface-active agent manufacturedby Toho Chemical Co., Ltd., Japan)1% aqueous solution of Xanthan gum 20 parts(natural high-molecular compound)Water 44.5 parts______________________________________

The above components except the active ingredient are homogeneously mixed together to form a solution, and thereto is added the active ingredient. The resulting mixture is throughly stirred, and wet-ground by means of sand mill to form a flowable. Upon use, the flowable is diluted up to one fiftieth to one twenty thousandth with water and applied at a rate of 0.005 to 50 kg of the active ingredient per hectare.

The compounds according to the present invention not only exhibit superior insecticidal action on hemiptera insect such as green rice leafhopper (Nephotettix cincticeps), lepidoptera insect such as diamondback moth (Plutella xylostella), Coleoptera and sanitary insect pests such as pale house mosquito (Culex pipiens), but are also useful for expelling mites parasitic on fruits and vegetables, such as two-spotted spider mite (Tetranychus urticae), Kanzawa spider mite (Tetranychus kanzawai), Carmine mite (Tetranychus cinnabarinus), citrus red mite (Panonychus citri) and European red mite (Panonychus ulmi), as well as ticks parasitic on animals, such as southern cattle tick (Boophilus microplus), cattle tick (Boophilus annulatus), gulf coast tick (Amblyomma maculatum), brown-ear tick (Rhipicephalus appendiculaturs) and Haemaphysalis longicornis. The main features of the compounds of the present invention reside in that the compounds are useful for the prevention or control of blight (or disease) of fruits and vegetables, such as powdery mildew, downy mildew, rust, rice blast disease (or rice blight) etc. in addition to having the above mentioned insecticidal, acaricidal and nematicidal actions. Accordingly, the compounds of the present invention are an excellent agricultural drug which enables control of pests and blight (or disease) simultaneously. Moreover, they are excellent as an expellent for ticks parasitic on animals such as domestic animals (e.g. cattle, horse, sheep and pig), domestic fowls, and other animals such as dog, cat, rabbit and the like.

The present invention is further explained in detail by way of the following test example.

TEST EXAMPLE 1

Insecticidal test on Green rice leafhopper (Nephotettix cincticeps)

20% emulsifiable concentrate of each of the present compounds described in the specification (some of which were applied with 25% wettable powder) was diluted with water containing an extender to prepare a 1000 ppm aqueous emulsion. This aqueous emulsion was dispersed in full amount to stems and leaves of paddy planted in a pot of 1/20000 and air-dried. Twenty second instar green rice leafhopper larvae which would show resistance to organic phosphorus type insecticides or carbamate type insecticides, per pot, were released in the pots. The paddies were covered with a cylindrical wire gauge and then placed in a thermostatic chamber. The numbers of the larvae killed was determined after 96 hours and the mortality thereof was calculated according to the equation below. Incidentally, the test was repeated twice for each compound. ##EQU1##

As the results, the following compounds exhibited 100% of mortality.

______________________________________Compound Nos. 14, 16, 17, 21, 22, 24, 25, 26, 29, 30, 31, 32, 33, 36, 38, 40, 41, 44, 45, 49, 53, 56, 61, 71, 72, 73, 75, 76, 77, 78, 79, 80, 82, 83, 84, 85, 87, 88, 89, 90, 92, 93, 97, 98, 99, 111, 112, 113, 127, 128, 129, 131, 148, 150, 174, 191, 202, 217, 220, 221, 226, 232, 235, 236, 239, 240, 267, 268, 269, 273, 277, 279, 280, 283, 284, 285, 288, 292, 323, 324, 359, 360, 364, 398, 426, 427, 429, 430, 432, 438, 443, 465, 466, 467, 468, 470, 472, 474, 475, 476, 477, 481, 482, 484, 488, 489, 490, 492, 494, 496, 498, 500, 514, 517, 518, 519, 520, 522, 524, 527, 528, 529, 540, 542, 565, 606, 609, 610, 643, 647, 652, 656, 657, 661, 664, 668, 670, 672, 676, 680, 702, 704, 708, 720, 722, 850, 851, 852, 857, 895, 1000, 1001, 1002 and 1143.______________________________________

TEST EXAMPLE 2

Insecticidal test on 28-spotted Lady beetle (Henosepilachna vigintioctopunctata)

A leaf of tomato was immersed for about 10 seconds in a 1000 ppm aqueous emulsion which had been prepared by diluting a 20% emulsifiable concentrate containing each compound described in the present specification (some of which were applied with 25% wettable powder) with water containing an extender and then air-drying. The leaf thus treated was placed in a laboratory dish, into which 10 second inster 28-spotted lady beetle larvae were released. The dish was then fitted with a cap provided with pores and then placed in a thermostatic chamber kept at 25.degree. C. The number of the larvae killed was determined after 96 hours and the mortality thereof was calculated according to the equation described in the Test Example 1. Incidentally, the test was repeated twice for each compound.

As the results, the following compounds exhibited 100% mortality.

______________________________________Compound Nos. 13, 14, 16, 17, 18, 21, 24, 25, 26, 29, 30, 31, 32, 33, 34, 36, 38, 40, 41, 44, 45, 46, 49, 53, 55, 56, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 82, 83, 84, 85, 87, 88, 89, 90, 92, 93, 94, 95, 97, 99, 100, 111, 112, 113, 127, 128, 129, 131, 134, 150, 161, 174, 191, 192, 193, 194, 202, 216, 217, 218, 220, 221, 226, 232, 235, 236, 248, 250, 251, 268, 269, 279, 280, 283, 284, 285, 288, 290, 323, 324, 360, 426, 427, 429, 430, 432, 438, 443, 463, 465, 466, 467, 468, 470, 472, 474, 475, 476, 477, 480, 481, 482, 484, 488, 489, 490, 492, 494, 496, 498, 500, 514, 517, 518, 519, 520, 522, 524, 527, 528, 529, 540, 542, 609, 618, 643, 652, 657, 662, 664, 668, 702, 704, 722, 843, 850, 851, 852, 857, 863, 895, 1002, 1141 and 1143.______________________________________

TEST EXAMPLE 3

Acaricidal test on Kanzawa Spider Mite (T. kanzawai)

A leaf of kidney bean was cut into a round piece of 1.5 cm in diameter by a leaf punch, and then placed on a moistened filter paper on a polystyrol cup of 7 cm in a diameter. Each piece of the leaf was inoculated with 10 Kanzawa Spider Mite nymphs. Half a day after the inoculation, each 2 ml of an aqueous emulsion containing 1000 ppm of the present compuond described in the speciication (some of which were applied with 25% wettable powder) diluted with water containing an extender was applied to each polystyrol cup by means of a rotary spray tower. After 96 hours, the mortality of the nymph was determined according to the equation described in the Test Example 1. Incidentally, the test was repeated twice for each compound.

As the results, the following compounds exhibited 100% mortality.

______________________________________Compound Nos. 13, 14, 15, 16, 17, 18, 24, 25, 26, 28, 29, 30, 31, 32, 33, 36, 40, 41, 44, 45, 49, 53, 55, 56, 70, 74, 76, 77, 78, 80, 83, 84, 85, 87, 88, 89, 90, 92, 93, 95, 97, 98, 99, 100, 111, 112, 113, 120, 129, 148, 150, 152, 161, 174, 191, 193, 194, 195, 197, 220, 221, 224, 226, 232, 235, 236, 240, 241, 250, 283, 287, 288, 290, 324, 344, 359, 360, 364, 398, 410, 421, 426, 427, 429, 430, 432, 438, 443, 463, 466, 467, 468, 470, 472, 475, 476, 477, 480, 481, 482, 488, 489, 490, 494, 514, 517, 518, 519, 520, 527, 529, 542, 606, 609, 610, 612, 643, 702, 704, 708, 720, 850, 851, 852, 857, 863, 895, 1001, 1002 and 1142.______________________________________

TEST EXAMPLE 4

Nematicidal test on Root-knot Nematode (Meloidogyne sp.)

Soil contaminated with root-knot nematode was placed in a polystyrol cup 8 cm in diameter. A liquid containing 1000 ppm of an active ingredient was prepared by diluting 20% emulsifiable concentrate containing a compound of the present invention (some of which were applied with 25% wettable powder) with water containing an extender. The soil contaminated with nematode and placed in the polystyrol cup was drenched with each 50 ml of the resulting liquid. After 48 hours, a tomato seedling as an indicator was transplanted into the soil thus treated. Thirty days after the transplanation, the roots of the tomato were washed with water and the root-knot parasitism was checked by observation. Incidentally, the test was repeated twice for each compound. As a result, no root-knot parasitism was observed in the roots of the tomato treated with the exhibit a strong nematicidal activity:

______________________________________Compound Nos. 17, 72, 73, 76, 78, 84, 85, 90, 92, 93, 221, 268, 269, 280, 283, 359, and 465.______________________________________

TEST EXAMPLE 5

Insecticidal test on Green rice leafhopper (Nephotettix cincticeps)(Comparative test)

Test was conducted in accordance with Test Example 1 except that the concentration of each of the present compound and a control compound was changed to 500 ppm. The results are shown in Table 5. From the results, it can be seen that the present compounds exhibit much higher insecticidal activity than the known control compounds.

TEST EXAMPLE 6

Insectical test on 28-spotted Lady Beetle (Henosepilachna vigintioctopunctata)(Comparative test)

Test was conducted in accordance with Test Example 2 except that the concentration of each of the present compound and a control compound was changed to 500 ppm. The results are shown in Table 5. From the results, it can be seen that the present compunds exhibit much higher insecticidal activity then the known control compounds.

TEST EXAMPLE 7

Acaricidal test on Kanzawa Spider Mite (T. kanzawai)(Comparative test)

Test was conducted in accordance with Test Example 3 except that the concentration of each of the present compound and a control compound was changed to 500 ppm. The results are shown in Table 5. From the results, it can be seen that the present compounds exhibit much higher acaricidal activity than the known control compounds.

TABLE 5______________________________________Insecticidal Test (Comparative test) Green rice 28-spotted lady Kanzawa leafhopper beetle spider miteCompound No. (mortality %) (mortality %) (mortality %)______________________________________Present compound 100 100 100No. 40Present compound 100 100 100No. 92Present compound 100 100 100No. 465Control 0 20 0compound AControl 20 0 50compound B______________________________________

The structural formulae of the present compounds in Table 5 are as follows: ##STR17##

On the other hand, the structural formulae of the control compounds are as follows: ##STR18##

TEST EXAMPLE 8

Residual activity text on 28-spotted lady beetle (Henosepilachna vigintioctopunctata)

Tomato planted in a pot of 1/5000 are was sprayed well with a 500 ppm aqueous emulsion which had been prepared by diluting with water containing an extender 20% emulsifiable concentrate containing each compound described in the present specification (some of which were applied with 25% wettable powder), air-dried and kept in a greenhouse. After 10 days, leaf of the tomato thus treated was cut out and placed in a laboratory dish, into which 10 second inster 28-spotted lady beetle larvae were released. The dish was then fitted with a cap provided with pores and then placed in a thermostatic chamber kept at 25.degree. C. The number of the larvae killed was checked after 96 hours and the mortality thereof was calculated according to the equation described in the Test Example 1. Incidentally, the test was repeated twice for each compound.

The following compounds exhibited 100% mortality.

______________________________________Compound Nos. 22, 84, 85, 89, 90, 112, 113, 426, 427, 429, 430, 432, 438, 443, 465, 468, 470, 472, 481, 490, 496, 517, 520, 522, 528, 857 and 895.______________________________________

Claims

1. A compound of the following formula: ##STR19## wherein Z.sup.3 represents halogen atom, straight or branched chain alkyl group having 1 to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms, alkylcarbonyl having 2 to 10 carbon atoms, alkoxyalkyl group having 2 to 4 carbon atoms, ##STR20## W represents halogen atom, alkyl group having 1 to 4 carbon atoms, alkoxy group having 1 to 4 carbon atoms, haloalkyl group having 1 to 4 carbon atoms, or nitro group, m is O or an integer of 1 to 2, and when m is 2, W may be same or different.

2. A composition for controlling insects, acari and nemati for argricultural and horticultural use and containing as active ingredient a compound of the following formula: ##STR21## wherein Z.sup.3 represents halogen atom, straight or branched chain alkyl group having 1 to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms, alkylcarbonyl having 2 to 10 carbon atoms, alkoxyalkyl group having 2 to 4 carbon atoms, ##STR22## W represents halogen atom, alkyl group having 1 to 4 carbon atoms, alkoxy group having 1 to 4 carbon atoms, haloalkyl group having 1 to 4 carbon atoms, or nitro group, m is O or an integer of 1 to 2, and when m is 2, W may be same or different.

3. A 2-t-butyl-4-chloro-5-[2-2,6-dimethyl-4-(4-methylphenoxy)phenoxy ethylthio]-3(2H)-pyridazinone of claim 1 having the formula: ##STR23##

4. A 2-t-butyl-4-chloro-5-[2-(2,6-dimethyl-4-phenoxyphenoxy)ethylthio]-3(2H)-pyridazinone of claim 1 having the formula: ##STR24##

5. A 2-t-butyl-4-chloro-5-[2-{2,6-dimethyl-4-(2,4-difluorobenzoyl)phenoxy}ethylthio]-3(2H)-pyridazinone of claim 1 having the formula: ##STR25##

6. A 2-t-butyl-4-chloro-5-[2-(2,6-dimethyl-4-ethoxyphenoxy)ethylthio]-3(2H)-pyridazinone of claim 1 having the formula: ##STR26##

7. A 2-t-butyl-4-chloro-5-[2-(2,6-dimethyl-4-methoxymethyl-phenoxy)ethylthio]-3(2H)-pyridazinone of claim 1 having the formula: ##STR27##