LT4014B

LT4014B - Fungicidal composition

Info

Publication number: LT4014B
Application number: LTIP1864A
Authority: LT
Inventors: Satoru Kumazawa; Susumi Shimizu; Hiroyuki Enari; Atsushi Ito; Susumu Ikeda; Nobuo Sato; Toshihide Saishoji
Original assignee: Kureha Chemical Ind Co Ltd
Priority date: 1987-06-30
Filing date: 1994-01-31
Publication date: 1996-08-26
Also published as: LTIP1864A; GEP19981389B; LV10744A; RU1837767C; DD289523A5; LV10744B; UA18635A

Abstract

Chemical mixtures for the protection of plants, namely the fungicidal compounds on the basis of a compound of 1-(azol-1-ilmethyl)-2benzylcyclopenthanol, the active ingredient of which has a formulae: <IMAGE> where R<1> and R<2> are hydrogen or C1-C5-alkyl, with a condition, that one of these residuals is not hydrogen; Xn is hydrogen, the fluorine, chlorine, bromine, C1-C4-alkyl, phenyl in the fourth position; chlorine in the second or fourth position; or fluorine in the second position and chlorine in the fourth position; A is an atom of nitrogen or -CH- group, together with various appurtenances. The ratio of these components (mass per cent) is such: active ingredient - 3:50, appurtenances comprise the rest part.

Description

Išradimas priskiriamas augalų apsaugos cheminiams mišiniams, konkrečiai fungicidiniam mišiniui 1-(azol-l-ilmetil)2-benzilciklopentanolio darinio pagrindu.The invention relates to chemical compositions for plant protection, in particular to a fungicidal mixture based on a 1- (azol-1-ylmethyl) 2-benzylcyclopentanol derivative.

Yra žinomas fungicidinis mišinys azolo pagrindu (N.N. Melnikov, K.V. Novožilova, T.N. Pylova Chimičeskie sredstva zaščity rastenij. Spravočnik, M. Chimija, 1980, p.225).An azole-based fungicidal mixture is known (N.N. Melnikov, K.V. Novozilova, T.N. Pylova Chimičeskie sredstva zaščity rastenij. Spravočnik, M. Chimija, 1980, p.225).

Labiau artimas pareiškiamam junginiui yra mišinys 1-(azoll-ilmetil ) -2-benzilciklopentanolio darinio pagrindu (GB patentas Nr.2180236A TPK C2C, publ. 1987.03.23).More closely related to the claimed compound is a mixture based on a derivative of 1- (azoll-ylmethyl) -2-benzylcyclopentanol (GB Patent No. 2180236A TPK C2C, published March 23, 1987).

Tačiau nurodyti fungicidiniai mišiniai, esant nedidelėms koncentracijoms, pasižymi mažu aktyvumu.However, the indicated fungicidal mixtures exhibit low activity at low concentrations.

Šio išradimo tikslas yra mišinio fungicidinio aktyvumo padidinimas. Tolesni pavyzdžiai iliustruoja patentuojamą pasiūlymą.The object of the present invention is to increase the fungicidal activity of the mixture. The following examples illustrate a patentable proposal.

pavyzdysexample

5-(4-chlorbenzil)-2,2-dimeti1-1-(1H-1,2,4-triazol-lilmetil ) ciklopentanolio gavimasPreparation of 5- (4-chlorobenzyl) -2,2-dimethyl-1- (1H-1,2,4-triazol-1-ylmethyl) cyclopentanol

Į 30 ml bevandenio dimetilformamido įdedama ir ištirpinama, maišant helio atmosferoje, 5,0 g 7-(4-chlorbenzil)-4,4-dimetil1-oksapiro(2,4)heptano. Į gautą mišinį palaipsniui pridedama 2,2 g 1H-1,2,4-triazolo natrio druskos (90 % švarumo). Mišinys maišomas dvi valandas 70 °C temperatūroje, atšaldomas, išpilamas į vandeni su ledu ir ekstrahuojamas etilacetatu. Organinis sluoksnis atskiriamas, perplaunamas vandeniu ir džiovinamas bevandeniu natrio sulfatu. Tirpiklis iš išdžiovinto organinio sluoksnio pašalinamas žemame slėgyje. Gauta liekana valoma chromatografinėje silikagelio kolonėlėje, ir gaunama 3,1 g galutinio produkto (2 junginys).To 30 ml of anhydrous dimethylformamide was added 5.0 g of 7- (4-chlorobenzyl) -4,4-dimethyl-1-oxapyr (2,4) heptane under stirring under an atmosphere of helium. 2.2 g of 1H-1,2,4-triazole sodium salt (90% purity) are gradually added to the resulting mixture. The mixture was stirred for two hours at 70 ° C, cooled, poured into water with ice and extracted with ethyl acetate. The organic layer was separated, washed with water and dried over anhydrous sodium sulfate. The solvent is removed from the dried organic layer under reduced pressure. The resulting residue was purified by silica gel column chromatography to give 3.1 g of the final product (compound 2).

pavyzdysexample

5-(2,4-dichlorbenzil)-2,2-dimeti1-1-(lH-imidazol-1ilmetil)ciklopentanolio gavimasPreparation of 5- (2,4-dichlorobenzyl) -2,2-dimethyl-1- (1H-imidazol-1-ylmethyl) cyclopentanol

Į 18 ml bevandenio dimetilformamido įdedama ir ištirpinama, maišant helio atmosferoje, 996 mg natrio hidrido (gauto perplaunant 60 % natrio hidridą alyvoje bevandeniu benzenu). Į susidariusį mišinį įdedama 2,83 g ΙΗ-imidazoio, ir mišinys maišomas kambario temperatūroje iki pasibaigs skirtis dujų burbuliukai. Į gautą mišinį lašinamas tirpalas, gautas ištirpinus 5,93 g 7-(2,4-dichlorbenzil)-4,4-dimetil-loksapiro(2,4)heptano 10 ml bevandenio dimetilformamido, ir gautas mišinys ekstrahuojamas etilacetatu, atskiriant organinį sluoksnį. Organinis sluoksnis perplaunamas vandeniu ir džiovinamas bevandeniu natrio sulfatu. Tirpiklis iš išdžiovinto organinio sluoksnio pašalinamas žemame slėgyje.Add 186 ml of anhydrous dimethylformamide and dissolve, under stirring in an atmosphere of helium, 996 mg of sodium hydride (obtained by washing 60% sodium hydride in oil with anhydrous benzene). To the resulting mixture was added 2.83 g of ΙΗ-imidazole and the mixture was stirred at room temperature until the gas bubbles had ceased. To the resulting mixture was added dropwise a solution of 5.93 g of 7- (2,4-dichlorobenzyl) -4,4-dimethyl-oxapyr (2,4) heptane in 10 ml of anhydrous dimethylformamide, and the resulting mixture was extracted with ethyl acetate, separating the organic layer. The organic layer was washed with water and dried over anhydrous sodium sulfate. The solvent is removed from the dried organic layer under reduced pressure.

Gauta liekana valoma chromatografinėje silikagėlio kolonėlėje ir perkristalinama iš n-heksano ir etilacetato mišinio. Gaunama 2,7 g galutinio produkto (15 junginys).The resulting residue was purified by silica gel column chromatography and recrystallized from a mixture of n-hexane and ethyl acetate. 2.7 g of the final product are obtained (compound 15).

Analogiškai gaunami ir kiti I formulės junginiai:Similarly, other compounds of formula I are obtained:

pateikti 1 lentelėje.are presented in Table 1.

lentelėje pateikti BMR spektrai gauti naudojant tetrametilsilaną, kaip vidinį standartą. Naudoti tokie pažymėjimai: s - singletas, d - dubletas, t - tripletas, q kvartetas, m - multipletas, b - platus signalas, J - sąveikos konstanta (Hz).The NMR spectra shown in the Table are obtained using tetramethylsilane as an internal standard. The following notations were used: s - singlet, d - doublet, t - triplet, q - quartet, m - multiplet, b - broad signal, J - interaction constant (Hz).

Iš 1 j unginiai lentelėje pateiktų junginių labiausiai tinkami yra šie Nr. 1-3, 5, 9-11, 16, 18.Of the compounds listed in Table 1, the following are most suitable. 1-3, 5, 9-11, 16, 18.

pavyzdysexample

DulkėsDust

Trys svorio dalys 1 junginio, 40 svorio dalių molio ir 57 svorio dalys talko sumaišomos ir susmulkinamos i miltelius.Three parts by weight of compound 1, 40 parts by weight of clay and 57 parts by weight of talc are mixed and pulverized.

pavyzdysexample

Drėkstantys milteliaiMoisturizing powder

Penkiasdešimt svorio dalių 1 junginio, 5 svorio dalys ligninsulsorūgšties druskos, 3 svorio dalys alkilsulforūgšties ir 42 svorio dalys diatomitinės žemės sumaišoma ir susmulkinama į miltelius.Fifty parts by weight of compound 1, 5 parts by weight of lignin salt, 3 parts by weight of alkyl sulphonic acid and 42 parts by weight of diatomaceous earth are mixed and powdered.

pavyzdysexample

GranulėsGranules

Dvidešimt polioksietilenoTwenty polyoxyethylene

Penkios svorio dalys 1 junginio, 43 svorio dalys bentonito, 45 svorio dalys molio ir 7 svorio dalys ligninsulforūgšties druskos homogeniškai sumaišomos, permaišomos, pridėjus vandens, granuliatoriuje suformuojamos granulės ir džiovinamos.Five parts by weight of compound 1, 43 parts by weight of bentonite, 45 parts by weight of clay and 7 parts by weight of lignin sulphonic acid salt are homogeneously mixed, mixed with the addition of water and granulated in a granulator and dried.

pavyzdysexample

Besiemulguoj antis koncentratas svorio dalių 1 junginio, 10 svorio dalių alkilakrilo eterio, 3 svorio dalys polioksietilensorbitano monolaurato ir 67 svorio dalys ksileno homogeniškai sumaišomos.The bulk concentrate is mixed homogeneously with 1 part by weight of compound 1, 10 parts by weight of alkyl acrylic ether, 3 parts by weight of polyoxyethylene sorbitan monolaurate and 67 parts by weight of xylene.

Analogišku būdu gaunami ir mišiniai pateikti 2 lentelėje.Analogously obtained mixtures are shown in Table 2.

pavyzdys esančių kiekviename iš 3 puodelių kviečių daigų, kurie buvo auginami neglazūruotuose 10 cm diametro puodeliuose ir esančių antrojo lapelio stadijoje, buvo paveikti 5 ml/puodeliui 4 pavyzdžio mišinio vandenine suspensija. Išdžiovinus ore koncentratą, daigai buvo apipurkšti suspensija vasarinių Erysiphegraminis f. sp. tritici sporų, surinktų nuo pažeistų kviečių lapų, ir puodeliai buvo laikomi 20-24 °C temperatūroje 24 valandas, esant aukštam drėgmės lygiui, o po to puodeliai buvo laikomi šiltnamyje. Praėjus 10 ir 12 dienų, susirgimo išplitimas buvo įvertinamas procentais, lyginant su kontrole (neapdorotais augalais).Rezultatai pateikti 3 lentelėje.A sample of each of 3 cups of wheat sprouts grown in unglazed 10 cm diameter cups and in the second leaf stage was exposed to 5 ml / cup of sample 4 aqueous suspension. After air drying of the concentrate, the sprouts were sprayed with a suspension of summer Erysiphegraminis f. m.p. tritici spores collected from damaged wheat leaves and the cups were stored at 20-24 ° C for 24 hours at high humidity and then the cups were stored in a greenhouse. After 10 and 12 days, the spread of the disease was evaluated as a percentage relative to the control (untreated plants). The results are shown in Table 3.

pavyzdysexample

Po vieną iš esančių kiekviename iš 3 puodelių agurkų daigų, kurie buvo auginami neglazūruotuose 10 cm diametro puodeliuose ir esančių antrojo lapelio stadijoje, buvo paveikti 5 ml/puodeliui 4 pavyzdžio mišinio vandenine suspensija. Išdžiovinus ore, ant daigų teptuku buvo užtepta Sphaerotheca fuliginea sporų, surinktų nuo pažeistų agurkų lapų, ir po 9 ir 11 dienų susirgimo išplitimas buvo įvertinamas kaip 11 pavyzdyje.Rezultatai pateikti 4 lentelėje.One of each contained in each of 3 cup cucumber sprouts grown in unglazed 10 cm diameter cups and in the second leaf stage was exposed to 5 ml / cup of the aqueous suspension of sample 4. After air-drying, spore brushes were applied to Sphaerotheca fuliginea spores collected from damaged cucumber leaves, and after 9 and 11 days, the spread of the disease was evaluated as in Example 11. The results are shown in Table 4.

pavyzdys esančių kiekviename iš 3 puodelių kviečių daigų, kurie buvo auginami neglazūruotuose 10 cm diametro puodeliuose ir esančių antrojo lapelio stadijoje, buvo paveikti 5 ml/puodeliui 4 pavyzdžio mišinio vandenine suspensija. Išdžiovinus ore, daigai buvo apipurkšti suspensija vasarinių Puccinia recodita sporų, surinktų nuo pažeistų kviečių lapų, ir puodeliai buvo laikomi 20-23 °C temperatūroje 24 valandas, esant aukštam drėgmės lygiui, o po to puodeliai buvo laikomi šiltnamyje. Praėjus 7 ir 11 dienų, susirgimo išplitimas buvo įvertinamas taip, kaip 11 pavyzdyje. Rezultatai pateikti 5 lentelėje.A sample of each of 3 cups of wheat sprouts grown in unglazed 10 cm diameter cups and in the second leaf stage was exposed to 5 ml / cup of sample 4 aqueous suspension. After air-drying, the sprouts were sprayed with a suspension of summer Puccinia recodita spores collected from damaged wheat leaves, and the cups were stored at 20-23 ° C for 24 hours at high humidity, and then the cups were stored in a greenhouse. At 7 and 11 days, the spread of disease was assessed as in Example 11. The results are shown in Table 5.

pavyzdysexample

Pupelių daigai, kurie buvo auginami neglazūruotuose 10 cm diametro puodeliuose ir buvo antrojo lapelio stadijoje, buvo paveikti mi/puodeliui pavyzdžio mišinio vandenine suspensija. Išdžiovinus ore, centrinėje augalo lapo dalyje buvo priklijuota 4 mm diametro agaro nuopjova, turinti Botrytis cinerea grybelius, kurie tris dienas buvo auginami 20 °C temperatūroje agaro terpėje, į ją pridėjus cukraus ir bulvių buljono. Puodeliai buvo laikomi 20-22 °C temperatūroje esant aukštam drėgmės lygiui. Po trijų dienų buvo įvertinamas susirgimo išplitimas (kaip 11 pavyzdyje).Rezultatai pateikti 6 lentelėje.Bean sprouts grown in unglazed 10 cm diameter cups and in the second leaf stage were exposed to the mi / cup aqueous suspension of the sample mixture. After air drying, a 4 mm diameter agar slice containing Botrytis cinerea fungus was grown in the central portion of the leaf of the plant, which was grown for three days at 20 ° C in agar medium with added sugar and potato broth. The cups were stored at 20-22 ° C at high humidity. After three days, the spread of the disease was evaluated (as in Example 11). The results are shown in Table 6.

pavyzdysexample

I kiekvieną 10 cm diametro neglazūruotą puodelį buvo pasodinta po 16 ryžių grūdelių ir ryžių daigams pasiekus 4-5 lapų stadiją, jie buvo paveikti atskiestu 4 pavyzdžio mišiniu. Išdžiovinus ore, daigų lapai buvo apipurkšti iš anksto paruošta Cochliobolus miyabeanus sporų suspensija, po 5 ml kiekvienam puodeliui. Iš karto po užkrėtimo puodeliai buvo patalpinti į inokuliacijos kamerą dviems dienoms 25 °C temperatūroje, esant aukštam drėgmės lygiui, o po to buvo perkelti i šiltnamį. Po penkių dienų buvo įvertintas susirgimo išplitimas (kaip 11 pavyzdyj e).Rezultatai pateikti 7 lentelėje.Each 10 cm diameter non-glazed cup was planted with 16 rice grains and exposed to the diluted mixture of Example 4 when the rice sprouts reached a 4-5 leaf stage. After air drying, the seedlings were sprayed with a pre-prepared suspension of Cochliobolus miyabeanus spores, 5 ml per cup. Immediately after challenge, the cups were placed in an inoculation chamber for two days at 25 ° C under high humidity conditions and then transferred to the greenhouse. Five days later, the spread of the disease was assessed (as in Example 11). The results are shown in Table 7.

pavyzdysexample

Bandymai buvo atlikti pagal 11 pavyzdžio metodiką, bet naudojant 6 pavyzdžio mišinį. Rezultatai pateikti 8 lentelėje.The tests were performed according to the procedure of Example 11 but using the mixture of Example 6. The results are shown in Table 8.

pavyzdysexample

Bandymai buvo atlikti pagal 13 pavyzdžio metodiką, bet naudojant 6 pavyzdžio mišinį. Rezultatai pateikti 9 lentelėje.The tests were carried out according to the procedure of Example 13 but using the mixture of Example 6. The results are shown in Table 9.

pavyzdysexample

Bandymai buvo atlikti pagal 11 pavyzdžio metodiką, bet naudojant 9 pavyzdžio mišinį. Rezultatai pateikti 10 lentelėje.The tests were carried out according to the procedure of Example 11 but using the mixture of Example 9. The results are shown in Table 10.

pavyzdysexample

Bandymai buvo atlikti pagal 13 pavyzdžio metodiką, bet naudojant 9 pavyzdžio mišinį. Rezultatai pateikti 11 lentelėje.The tests were performed according to the procedure of Example 13 but using the mixture of Example 9. The results are shown in Table 11.

pavyzdysexample

Bandymai buvo atlikti pagal 13 pavyzdžio metodiką, bet naudojant 4 pavyzdžio mišinį. Rezultatai pateikti 12 lentelėje.The tests were performed according to the procedure of Example 13 but using the mixture of Example 4. The results are shown in Table 12.

pavyzdysexample

Bandymai buvo atlikti pagal 11 pavyzdžio metodiką, bet naudojant 4 pavyzdžio mišinį. Rezultatai pateikti 13 lentelėje.The tests were performed according to the procedure of Example 11 but using the mixture of Example 4. The results are shown in Table 13.

pavyzdysexample

Bandymai buvo atlikti pagal 13 pavyzdžio metodiką, bet naudojant 5 pavyzdžio mišinį. Rezultatai pateikti 14 lentelėje.The tests were carried out according to the procedure of Example 13 but using the mixture of Example 5. The results are shown in Table 14.

pavyzdysexample

Bandymai buvo atlikti pagal 11 pavyzdžio metodiką, bet naudojant 5 pavyzdžio mišinį. Rezultatai pateikti 15 lentelėje.The tests were carried out according to the procedure of Example 11 but using the mixture of Example 5. The results are shown in Table 15.

pavyzdysexample

Bandymai buvo atlikti pagal 13 pavyzdžio metodiką, bet naudojant^8 pavyzdžio mišinį. Rezultatai pateikti 16 lentelėje.The tests were carried out according to the procedure of Example 13 but using a mixture of Example 8. The results are shown in Table 16.

pavyzdysexample

Bandymai buvo atlikti pagal 14 pavyzdžio metodiką, bet naudojant 8 pavyzdžio mišinį. Rezultatai pateikti 17 lentelėje.The tests were performed according to the procedure of Example 14 but using the mixture of Example 8. The results are shown in Table 17.

pavyzdysexample

Bandymai buvo atlikti pagal 13 pavyzdžio metodiką, bet naudojant 10 pavyzdžio mišinį. Rezultatai pateikti 18 lentelėje.The tests were performed according to the procedure of Example 13 but using the mixture of Example 10. The results are shown in Table 18.

pavyzdysexample

Bandymai buvo atlikti pagal 11 pavyzdžio metodiką, bet naudojant 10 pavyzdžio mišinį. Rezultatai pateikti 19 lentelėje.The tests were carried out according to the procedure of Example 11 but using the mixture of Example 10. The results are shown in Table 19.

Tokie pateikti išradime mišiniai pasižymi aukštu fungicidiniu aktyvumu, esant mažoms koncentracijoms.Such mixtures of the present invention exhibit high fungicidal activity at low concentrations.

lentelėtable

Fizikinės-cheminės I formulės junginių savybėsPhysico-chemical properties of compounds of formula I

Jun- R¹ R² Xn A Stereo- Lyd.t. MBR spektras(CDC13,δ ginio izomero °C mln.d.)Jun- R ¹ R ² Xn A Stereo- Lyd.t. MBR spectrum (CDCl3, δ g of the isomer is C)

Nr. tipasNo. type

1. CH₃ CH₃ 4-C1 N A-tipas 113-114 0,60(s, 3H l,00(s,3H)1. CH ₃ CH ₃ 4 -C 1 N Type A 113-114 0.60 (s, 3H l, 00 (s, 3H)

1,07-1,90(m,5H) 2,33(s,2H) 3,53(s,lH) 4,13(s,2H) 6,80-7,23 (m,4H) 7,83(s,lH)1.07-1.90 (m, 5H) 2.33 (s, 2H) 3.53 (s, 1H) 4.13 (s, 2H) 6.80-7.23 (m, 4H) 7, 83 (s, 1H)

2. CH₃ CH₃ 4-C1 N B-tipas 113-114 0,82(s, 3H l,00(s,3H)2. CH ₃ CH ₃ 4 -C 1 N B Type 113-114 0.82 (s, 3H l, 00 (s, 3H)

1,23-1,93(m,4H) ch₃ ch₃ ch₃ ch₃ 1.23-1.93 (m, 4H) ch ₃ ch ₃ ch ₃ ch ₃

CH₃ CH ₃

CH,CH,

4-C1 CH A-tipas 113-1144-C1 CH A-Type 113-114

4-C1 'CH B-tipas 113-1144-C1 'CH B-Type 113-114

4-Br N A-tipas 113-1144-Br N A-Type 113-114

4-Br N B-tipas 113-1144-Br N B-Type 113-114

4-Br CH A-tipas 113-1144-Br CH A-Type 113-114

4-Br CH B-tipas 113-1144-Br CH B-Type 113-114

4-F N A-tipas 113-1144-F N A-Type 113-114

4-F N B-tiDas 113-1144-F N B-tiDas 113-114

4-F CH A-tipas 113-1144-F CH A-Type 113-114

4-F CH B-tipas 104-106 (m, 2H) 2,85-3,07(m, 1H)4-F CH Type B 104-106 (m, 2H) 2.85-3.07 (m, 1H)

3,90(s, 1H) 4,37(s, 2H)3.90 (s, 1H) 4.37 (s, 2H)

7,03(d, 2H, j=8) 7,25(d,7.03 (d, 2H, j = 8) 7.25 (d,

2H, j=8) 7,9 7 (s, 1H)2H, j = 8) 7.9 (s, 1H)

8,27(s, 1H)8.27 (s, 1H)

0,80(s, 3H) l,03(s, 3H)0.80 (s, 3H) 1.03 (s, 3H)

1.13- 2,93(m, 8H) 3,97(s,1.13-2.93 (m, 8H) 3.97 (s,

2H) 7,02(s, 2H) 6,80-7,33 (m, 4H) 7,60(s, 1H)2H) 7.02 (s, 2H) 6.80-7.33 (m, 4H) 7.60 (s, 1H)

0,83(s, l,03(s, 3H) 1,133,13(m, 8H) 4,03(s, 2H) 8,70~7,23(m, 6H) 7,63(s,0.83 (s, 1.03 (s, 3H) 1.133.13 (m, 8H) 4.03 (s, 2H) 8.70 ~ 7.23 (m, 6H) 7.63 (s,

1H)1H)

0,63(s, 3H) l,00(s, 3H)0.63 (s, 3H) 1.00 (s, 3H)

1.13- 1,93(m, 5H) 2,33(s,1.13-1.93 (m, 5H) 2.33 (s,

2H) 3,60(s, 1H) 4,20(s, 2H) 6,93-7,50(m, 4H) 7,97(s,2H) 3.60 (s, 1H) 4.20 (s, 2H) 6.93-7.50 (m, 4H) 7.97 (s,

1H) 8,17(s, 1H)1H) 8.17 (s, 1H)

0,77(s, 3H),0,97(s, 3H) 2,20-3,03(m, 7H) 3,80(s,0.77 (s, 3H), 0.97 (s, 3H) 2.20-3.03 (m, 7H) 3.80 (s,

1H) 4,33(s, 2H) 6,87-7,47 (m, 4H) 7,93(s, 1H) 8,20(s, 1H)1H) 4.33 (s, 2H) 6.87-7.47 (m, 4H) 7.93 (s, 1H) 8.20 (s, 1H)

0,80(s, 3H) l,03(s, 3H)0.80 (s, 3H) 1.03 (s, 3H)

1.13- 2,53(m, 8H) 4,00(s,1.13-2.53 (m, 8H) 4.00 (s,

2H) 6,80-7,50(m,6H) 7,63(s, 1H)2H) 6.80-7.50 (m, 6H) 7.63 (s, 1H)

0,83(s, 3H) l,03(s, 3H) l,17~2,97(m, 8H) 4,03(s,0.83 (s, 3H) 1.03 (s, 3H) 1.17 ~ 2.97 (m, 8H) 4.03 (s,

2H) 6,70-7,40(m, 6H) 7,57 (s, 1H)2H) 6.70-7.40 (m, 6H) 7.57 (s, 1H)

0,67(s, 3H) l,03(s, 3H)0.67 (s, 3H) 1.03 (s, 3H)

1.17- 2,42(m, 4H) 2,50(s,1.17 - 2.42 (m, 4H) 2.50 (s,

3H) 3,63(s, 1H) 4,23(s, 2H) 6,73~7,33(m, 4H) 7,93(s,3H) 3.63 (s, 1H) 4.23 (s, 2H) 6.73 ~ 7.33 (m, 4H) 7.93 (s,

1H) 8,13(s, 1H)1H) 8.13 (s, 1H)

0,80 (s, 3H) l,02(s, 3H) 1,27-3,10(m, 7H) 3,90(m,0.80 (s, 3H) 1.02 (s, 3H) 1.27-3.10 (m, 7H) 3.90 (m,

1H) 4,37(s, 2H) 6,73-7,27 (m, 4H) 7,97(s, 1H) 8,27(s, 1H)1H) 4.37 (s, 2H) 6.73-7.27 (m, 4H) 7.97 (s, 1H) 8.27 (s, 1H)

0,83(s, 3H) l,07(s, 3H)0.83 (s, 3H) 1.07 (s, 3H)

0,90-2,00(m, 5H) 2,25(s,0.90-2.00 (m, 5H) 2.25 (s,

2H) 2,57(s, 1H) 4,03(s, 2H) 6,73-7,27(m, 6H) 7,67(s,2H) 2.57 (s, 1H) 4.03 (s, 2H) 6.73-7.27 (m, 6H) 7.67 (s,

1H)1H)

0,87 (s, 3H), 1,03 (s, 3H),0.87 (s, 3H), 1.03 (s, 3H),

1.17- 3,03 (m, 8H), 4,10 (s, 2H), 6,70-7,27 (m, 6H),1.17-3.03 (m, 8H), 4.10 (s, 2H), 6.70-7.27 (m, 6H),

7,73 (s, 1H)7.73 (s, 1H)

0,56 (s, 3H), 1,01 (s, 3H),0.56 (s, 3H), 1.01 (s, 3H),

0,79—(m,5H), 2,66 (s, 2H),0.79- (m, 5H), 2.66 (s, 2H),

3,97 (s, 1H) 4,2 H) 7,2 (s.3.97 (s, 1H) 4.2 H) 7.2 (s.

2,4- N B-tipas Cl₂ 2,4- N B-Type Cl ₂

126-127126-127

CH₃ gh₃ ch₃ ch₃ CH ₃ gh ₃ ch ₃ ch ₃

CH₃ HCH ₃ H

4-C14-C1

H CH₃ H CH ₃

- Cl- Cl

H CH₃ H CH ₃

4-C14-C1

GH₃ HGH ₃ H

4-C14-C1

2,4ci₂ 2.4ci ₂

2,4Gl₂ 2.4Gl ₂

4-C14-C1

2H), 7,2 1H), 7,92 1H) 2H), 7.2 1H), 7.92 1H) (s, (s, (s, (s, 2H) , 1H) , 2H), 1H), 7,28 (s. 7.28 (s. 8,12 8.12 (s, (s, N N B-tipas Type B 108-110 108-110 0,80 (s, 0.80 (s, 3H) , 3H), 1,02 1.02 (s , (s, 3H) , 3H), 1,25-1,88 1.25-1.88 (m, (m, 4H) , 4H), 2,33-3,03 2.33-3.03 (m. (m. 2H) , 2H), 3,75 3.75 (s, (s, 1H), 4,37 1H), 4.37 (s, (s, 2H) , 2H), 7,08-7,37 7.08-7.37 (m, (m, 3H) , 3H), 7,93 7.93 (s, (s, 1H), 8,23 1H), 8.23 (s, (s, 1H) 1H) CH CH A-tipas Type A 131-132 131-132 0,70 (s. 0.70 (s. 3h) , 3h), 1,03 1.03 (s. (s. 3H) , 3H), 1,16-2,65 1.16-2.65 (m, (m, 5H) , 5H), 2,53 2.53 (s, (s, 2H), 2,72 2H), 2.72 (s, (s, 1H) , 1H), 4,01 4.01 (s, (s, 2H), 6,99 2H), 6.99 (s, (s, 1H) , 1H), 7,03 7.03 (s, (s, 1H), 7,24 1H) 1H), 7.24 1H) (s, (s, 1H) , 1H), 7,58 7.58 (s, (s, N N A-tipas Type A 100-102 100-102 0,74 (d, 0.74 (d, 3H, 3H, J=5) , J = 5),

1,00-2,27 (m, 6H), 2,49(d, 2H, J=6,4), 3,07 (s, 1H), 4,20 (s, 2H), 7,03(d, 2H, J=8,4), 7,22(d, 2H, J~8,4), 7,95(s, 1H), 8,08(s, 1H)1.00-2.27 (m, 6H), 2.49 (d, 2H, J = 6.4), 3.07 (s, 1H), 4.20 (s, 2H), 7.03 ( d, 2H, J = 8.4), 7.22 (d, 2H, J = 8.4), 7.95 (s, 1H), 8.08 (s, 1H)

CH A-tipas 118-119 0,85(d, 3H, J=5,8),CH A-type 118-119 0.85 (d, 3H, J = 5.8),

1,07-2,23 (m, 6H), 2,51 (s, 2H, J=6,4), 3,34 (s, 1H) , 3,95 (s, 2H) , 6,95(s, 1H) , 6,98(d, 2H, J=8), 7,01 (s, 1H), 7,18(d, 2H, J=8), 7,48(s, 1H)1.07-2.23 (m, 6H), 2.51 (s, 2H, J = 6.4), 3.34 (s, 1H), 3.95 (s, 2H), 6.95 ( s, 1H), 6.98 (d, 2H, J = 8), 7.01 (s, 1H), 7.18 (d, 2H, J = 8), 7.48 (s, 1H)

N A-tipas 75-76 0,90(d, 3H),N A-type 75-76 0.90 (d, 3H),

J=6,4)1,28-2,24(m, 6H), 2,28, 2,58(m, 2H), 3,60(s, 1H) , 3,99 (d, 1H, J=14) ,J = 6.4 1.28-2.24 (m, 6H), 2.28, 2.58 (m, 2H), 3.60 (s, 1H), 3.99 (d, 1H, J = 14),

4,39(d, 1H, J=14), 6,97(d, 2H, J=9) , 8,00 (s, 1H) ,4.39 (d, 1H, J = 14), 6.97 (d, 2H, J = 9), 8.00 (s, 1H),

8,18 (s , 1H) , 7,24(d, 2H, J=9)8.18 (s, 1H), 7.24 (d, 2H, J = 9)

N B-tipas 79-81 0,80(d, 3H, J=6,4),N-type 79-81 0.80 (d, 3H, J = 6.4),

0,99-2,56(m, 7H), 2,73~3,39(m, 1H), 3,90(s, 1H), 4,1(d, 1H, J=14),0.99-2.56 (m, 7H), 2.73 ~ 3.39 (m, 1H), 3.90 (s, 1H), 4.1 (d, 1H, J = 14),

4,38(d, 1H, J=14), 7,04(d, 2H, J=9,4), 7,26(d, 2H, J=9,4) , 7,2 (s, 1H), 8,22 (s, 1H)4.38 (d, 1H, J = 14), 7.04 (d, 2H, J = 9.4), 7.26 (d, 2H, J = 9.4), 7.2 (s, 1H ), 8.22 (s, 1H)

N B-tipas aliejus o,88 (d, 3H, J=6,6),N type B oil o, 88 (d, 3H, J = 6.6),

1,05-2,45(m, 7H),1.05-2.45 (m, 7H),

2,62-2,92(m, 1H),2.62-2.92 (m, 1H),

3,95-4,25(m, 1, 1H, OH),3.95-4.25 (m, 1, 1H, OH),

4,31 (s, 2H) , 6,98(d, 2H,4.31 (s, 2H), 6.98 (d, 2H,

J=8,8), 7,22(m. 1, 2H,J = 8.8), 7.22 (m. 1.2H,

J=8,8), 7,95 (s, IH) ,J = 8.8), 7.95 (s, 1H),

8,26(s, IH)8.26 (s, 1H)

ch₃ ch ₃ ch₃ ch ₃ H H N N A-tipas Type A aliejus oil 0,63 (s, 3H) , 1,03 (s, 3H), 1,13-2,83(m, 7H), 3,57(s, IH) , 4,23 (s, 2H) , 7,23(s, 5H) , 8,00 (s, IH) , 8,17 (s, IH) 0.63 (s, 3H), 1.03 (s, 3H), 1.13-2.83 (m, 7H), 3.57 (s, 1H), 4.23 (s, 2H), 7 , 23 (s, 5H), 8.00 (s, 1H), 8.17 (s, 1H) ch₃ ch ₃ gh₃ gh ₃ H H CH CH A-tipas Type A 128-130 128-130 0,77 (s, 3H), 1,03 (s, 3H), 0.77 (s, 3H), 1.03 (s, 3H),

1,10-2,17(m, 5H) , 1,97 (s, IH), 2,17-2,50(m, 2H),1.10-2.17 (m, 5H), 1.97 (s, 1H), 2.17-2.50 (m, 2H),

3,97(s, 2H), 7H), 7,57(s, 3.97 (s, 2H), 7H), 7.57 (s, 6,87-7,33(m, IH) 6.87-7.33 (m, 1H) ch₃ ch ₃ ch₃ ch ₃ 4-CH₃ 4-CH ₃ N N A-tipas Type A 123-124 123-124 0,57(s, 3H), 1,10-2,57(m, 3H) , 4,20 (s, 4H) , 7,95 (s, IH) 0.57 (s, 3H), 1.10-2.57 (m, 3H), 4.20 (s, 4H), 7.95 (s, 1H) l,02(s, 3H), 8H), 2,27(s, 2H), 7,02(s, IH) , 8,13 (s, 1.02 (s, 3H), 8H), 2.27 (s, 2H), 7.02 (s, 1H), 8.13 (s, ch₃ ch ₃ ch₃ ch ₃ 4 - CH₃ 4 - CH ₃ N N B - tipas B - type 114-115 114-115 0,73 (s, 3H) , 1,67-3,00(m, 3H) , 3,72 (s, 2H), 6,93 (s, IH) , 8,10 (s. 0.73 (s, 3H), 1.67-3.00 (m, 3H), 3.72 (s, 2H), 6.93 (s, 1H), 8.10 (s. 0,98 (s , 3H) , 7H), 2,25(s, IH) , 4,28 (s, 4H) , 7,83 (s, IH) 0.98 (s, 3H), 7H), 2.25 (s, 1H), 4.28 (s, 4H), 7.83 (s, 1H) ch₃ ch ₃ ch₃ ch ₃ 4-CH₃ 4-CH ₃ CH CH A-tipas Type A 132-133 132-133 0,75(s, 3H) , 1,02—2,42(m, 3H), 3,93(s, 4H), 7,02(s, IH) 0.75 (s, 3H), 1.02 - 2.42 (m, 3H), 3.93 (s, 4H), 7.02 (s, 1H) 1,02 (s, 3H) , 3H), 2,27(s, 2H), 6,98(s, 2H) , 7,58 (s, 1.02 (s, 3H), 3H), 2.27 (s, 2H), 6.98 (s, 2H), 7.58 (s, ch₃ ch ₃ ch₃ ch ₃ 4-CH₃ 4-CH ₃ CH CH B-tipas Type B 130-131 130-131 0,83 (s, 3H), 1,17-3,07(m, 3H), 4,07(s, 6,77-7,20(m, 4H) , 7,62 (s. 0.83 (s, 3H), 1.17-3.07 (m, 3H), 4.07 (s, 6.77-7.20 (m, 4H), 7.62 (s). 1,07 (s, 3H) , 8H), 2,27(s, 2H) , 2H) , 6,98 (s, IK) 1.07 (s, 3H), 8H), 2.27 (s, 2H), 2H), 6.98 (s, IC) ch₃ ch ₃ ch₃ ch ₃ 2-F 4-CI 2-F 4-CI N N A-tipas Type A 129-130 129-130 0,62(s, 3H), 1,13-2,67(m, 1H), 4,2i(s, 6,23-7,23(m, IH), 8,ll(s, 0.62 (s, 3H), 1.13-2.67 (m, 1H), 4.2i (s, 6.23-7.23 (m, 1H), 8.11 (s, 1,02 (s, 3H), 7H) , 3,82 (s, 2H) , 3H) , 7,89 (s, IH) 1.02 (s, 3H), 7H), 3.82 (s, 2H), 3H), 7.89 (s, IH) ch₃ ch ₃ ch₃ ch ₃ 2-F 4-CI 2-F 4-CI CH CH A-tipas Type A 152-154 152-154 0,73(s, 3H) , 1,10-2,80(m, 0.73 (s, 3H), 1.10-2.80 (m, l,02(s, 3H) , 8H), 3,98(s. 1.02 (s, 3H), 8H), 3.98 (s.

2H), 6,68-7,20(m, 5H),2H), 6.68-7.20 (m, 5H),

c₂h₅ c ₂ h ₅ H H 4-CI 4-CI N N A-tipas Type A 82-84 82-84 7,57(s, IH) 0,67-2,23(m, 7.57 (s, 1H) 0.67-2.23 (m, 11H), 2,43 (d 11H), 2.43 (d H H c₂h₅ c ₂ h ₅ 4-CI 4-CI N N A-tipas Type A 93-95 93-95 2H, J=7) , 2,93 (s, IH) , 4,20 (s, 2H) , 6,93-7,33 (m, 4H) , 7,93 (s, IH) , 8,07 (s, IH) 0,70-2,13(m, 11H), 2H, J = 7), 2.93 (s, 1H), 4.20 (s, 2H), 6.93-7.33 (m, 4H), 7.93 (s, 1H), 8.07 (s, 1H) 0.70-2.13 (m, 11H),

2,13~2,47(m, 2H), 3,33(s,2.13 ~ 2.47 (m, 2H), 3.33 (s,

IH), 4,00(d, IH, J=14),1H), 4.00 (d, 1H, J = 14),

4,30(d, IK, J=14), 6,88(d,4.30 (d, IK, J = 14), 6.88 (d,

H C₂H₅ 4-C1HC ₂ H ₅ 4 -C 1

C₂H₅ H 4-C1C ₂ H ₅ H 4 -C 1

C₂H₅ C₂H₅ 4 - ClC ₂ H ₅ C ₂ H ₅ 4 - Cl

C₂H₅ C₂H₅ 4-C1C ₂ H ₅ C ₂ H ₅ 4-C1

C₂H₅ C₂H₅ 4 - ClC ₂ H ₅ C ₂ H ₅ 4 - Cl

CHCH

C₂H₅ C₂H_s 4 - ClC ₂ H ₅ C ₂ H _s 4 - Cl

CHCH

H-C₃H₇ H 4-C1HC ₃ H ₇ H 4 -Cl

H H-C3H7 4-C1H H-C3H7 4-C1

2H, J=8), 7,18(d, 2H, J=8),2H, J = 8), 7.18 (d, 2H, J = 8),

7,93(s, IH), 8,17(s, IH)7.93 (s, 1H), 8.17 (s, 1H)

B-tipas 76-78 0,67-3,33(m, 13H), 3,07(d,Type B 76-78 0.67-3.33 (m, 13H), 3.07 (d,

IH, J=10), 4,13(d, IH,1H, J = 10), 4.13 (d, 1H,

J=14), 4,40(d, IH, J=14), 7,03(d, 2H, J=8), 7,23(d, 2H, J=8) , 7,97 (s, IH), 7,18(s, IH)J = 14), 4.40 (d, 1H, J = 14), 7.03 (d, 2H, J = 8), 7.23 (d, 2H, J = 8), 7.97 (s, 1H), 7.18 (s, 1H)

B-tipas 110-112 0,67~2,20(m, 12H), 2,73(d,Type B 110-112 0.67 ~ 2.20 (m, 12H), 2.73 (d,

IH, J=10), 4,15(s, IH),1H, J = 10), 4.15 (s, 1H),

4,30 (s, 2H) , 6,95 (d, 2H,4.30 (s, 2H), 6.95 (d, 2H,

J=8) , 7,20(d, 2H, J=8), 7,97(s, IH), 8,25(s, IH)J = 8), 7.20 (d, 2H, J = 8), 7.97 (s, 1H), 8.25 (s, 1H)

A-tipas 124-126 0,67~l,07(m, 6H),Type A 124-126 0.67 ~ 1.07 (m, 6H),

1,07-2,40(m, 11H), 3,52(s, IH), 4,30 (s, 2H), 6,87(d, 2H, J=9), 7,18(d, 2H, J=9), 7,93(s, IH), 8,18(s, IH)1.07-2.40 (m, 11H), 3.52 (s, 1H), 4.30 (s, 2H), 6.87 (d, 2H, J = 9), 7.18 (d, 2H, J = 9), 7.93 (s, 1H), 8.18 (s, 1H)

B-tipas 143-145 o,87(t, 6H, J=6),Type B 143-145 °, 87 (t, 6H, J = 6),

1.10- 1,97(m, 8H),1.10-1.97 (m, 8H),

1,97—2,54(m, 2H) , 2,73(d, IH, J=9), 2,33-3,70(d, IH) , 4,43(s, 2H), 6,92(d, 2H, J=9), 7,20(d, 2H, J=9), 7,97(s, IH), 8,27(s, IH)1.97-2.54 (m, 2H), 2.73 (d, 1H, J = 9), 2.33-3.70 (d, 1H), 4.43 (s, 2H), 6, 92 (d, 2H, J = 9), 7.20 (d, 2H, J = 9), 7.97 (s, 1H), 8.27 (s, 1H)

A-tipas aliejus o,87(t, 6H, J=6),Type A oil o, 87 (t, 6H, J = 6),

1,07-2,50 (m, 11H) , 3,33 (s, IH) , 3,90(d, IH, J=14) ,1.07-2.50 (m, 11H), 3.33 (s, 1H), 3.90 (d, 1H, J = 14),

4,18(d, IH, J=14),4.18 (d, 1H, J = 14),

6,70-7,23(m, 6H) , 7,67 (s, IH)6.70-7.23 (m, 6H), 7.67 (s, 1H)

B-tipas 143-145 0,87 (t, 6H, J=6) ,Type B 143-145 0.87 (t, 6H, J = 6),

1.10- 2,33(m, 10H), 2,53~2,88(m, 2H), 4,13(s, 2H), 6,75-7,35(m, CH),1.10- 2.33 (m, 10H), 2.53 ~ 2.88 (m, 2H), 4.13 (s, 2H), 6.75-7.35 (m, CH),

7,70 (s, IH)7.70 (s, 1H)

A-tipas 83-85 0,61~2,26(m, 13H),A-type 83-85 0.61 ~ 2.26 (m, 13H),

2,26-2,57(m, 2H), 2,51-2,81(1, IH), 2,21(s, 2H), 7,03(d, 2H, J=9),2.26-2.57 (m, 2H), 2.51-2.81 (1, 1H), 2.21 (s, 2H), 7.03 (d, 2H, J = 9),

7,23(d, 2H, J=9) , 7,96 (s, IH) , 8,07(s, IH) ·7.23 (d, 2H, J = 9), 7.96 (s, 1H), 8.07 (s, 1H) ·

A-tipas 75-77 0,65~l,04(m, 3H),Type A 75-77 0.65 ~ 1.04 (m, 3H),

1,04-2,18(m, 10H),1.04-2.18 (m, 10H),

2,18-2,48(m, 2H) , 3,70 (s,2.18-2.48 (m, 2H), 3.70 (s,

IH), 3,98(d, IH, J=14),1H), 3.98 (d, 1H, J = 14),

4,29(d, IH, J=14), 6,86(d,4.29 (d, 1H, J = 14), 6.86 (d,

2H, J=8,4), 7,16(d, 2H,2H, J = 8.4), 7.16 (d, 2H,

H-C3H7 HH-C 3 H 7 H

J=8,4), 7,94 (s, 1H),J = 8.4), 7.94 (s, 1H),

8,12(s, 1H)8.12 (s, 1H)

4-G1 CH A-tipas 115-117 0,57~l,04(m, 3H),4-G1 CH Type A 115-117 0.57 ~ 1.04 (m, 3H),

1,04-2,24(m, 10H), 2,43(s, 2H), 2,55(s, 1H) , 3,96 (s, 2H) , 6,99 (d, 2H, J=8,4), 7,02 (s, 2H) , 7,20(d, 2H, J=8. 4) , 7,45(s, 1H)1.04-2.24 (m, 10H), 2.43 (s, 2H), 2.55 (s, 1H), 3.96 (s, 2H), 6.99 (d, 2H, J = 8.4), 7.02 (s, 2H), 7.20 (d, 2H, J = 8.4), 7.45 (s, 1H)

40 40 C₂H₅ C ₂ H ₅ H H 2,4- Cl₂ 2,4-Cl ₂ N N A- tipas Type A- 124-127 124-127 0,63—2,40(m, 2,68'(d, 2H, 1H), 4,23(s, 2H), 7,30(s, 1H) , 8,10 (s , 0.63-2.40 (m, 2.68 '(d, 2H, 1H), 4.23 (s, 2H), 7.30 (s, 1H), 8.10 (s, s, 11H), J=6), 3,10(s, 2H), 7,13(s, ĮH) , 7,93 (s, 1H) s, 11H), J = 6), 3.10 (s, 2H), 7.13 (s, 1H), 7.93 (s, 1H) 41 41 C2H5 C2H5 H H 2,4- CI2 2,4- CI2 CH CH A-tipas Type A 111-113 111-113 0,67-2,27(m, 2H, J=7), 2, 3,98 (s, 2H) , 6,97(s, 2H), 7,50(s, 1H) 0.67-2.27 (m, 2H, J = 7), 2. 3.98 (s, 2H), 6.97 (s, 2H), 7.50 (s, 1H) 11H), 2,50(d 63 (s, 1H), 6,90(s, 2H) , 7,37(s, 1H), 11H), 2.50 (d 63 (s, 1H), 6.90 (s, 2H), 7.37 (s, 1H), 42 42 c₂H₅ c ₂ H ₅ H H 4-F 4-F N N A-tipas Type A 73-74 73-74 0,62-2,19(m, 2,30~2,51(m, 1H), 4,15(s, 6,64-7,23(m, 1H), 8,99(s, 0.62-2.19 (m, 2.30 ~ 2.51 (m, 1H), 4.15 (s, 6.64-7.23 (m, 1H), 8.99 (s, 11H) , 2H) , 2,62 (s, 2H) , 4H) , 7,38 (s, 1H) 11H), 2H), 2.62 (s, 2H), 4H), 7.38 (s, 1H) 43 43 c₂h₅ c ₂ h ₅ H H 4-F 4-F CH CH A-tipas Type A 111-113 111-113 0,66-2,07(m, 0.66-2.07 (m, 11H) , 2,19 (s 11H), 2.19 (s

1H), 2,35-2,60(m, 2H),1H), 2.35-2.60 (m, 2H),

44 44 c₂h₅ c ₂ h ₅ H H 4-Br 4-Br N N A-tipas 80-82 A-type 80-82 3,93 (s, 2H) , 6,63-7,20 (m, 6h) , 7,41 (s, 1H) 0,68—2,25 (m, 11H), 2,43 (d 3.93 (s, 2H), 6.63-7.20 (m, 6h), 7.41 (s, 1H) 0.68-2.25 (m, 11H), 2.43 (d

2H, J-^_7), 2,85(s, 1H),2H, ^_ J-7), 2.85 (s, 1H)

4,22 (s, 2H), 6,37(d, 2H, J=7) , 7,93 (s, 1H) , 8,09 (s, 1H)4.22 (s, 2H), 6.37 (d, 2H, J = 7), 7.93 (s, 1H), 8.09 (s, 1H)

45 45 c₂h₅ c ₂ h ₅ H H 4-Br 4-Br CK CK A- tipas Type A- 117-119 0,60-2,50(m, 11H), 2,33~3,02(m, 2H), 3,18(s, 117-119 0.60-2.50 (m, 11H), 2.33 ~ 3.02 (m, 2H), 3.18 (s, 1H) , 4,00 (s, 6,88-7,02(m, 7,03-7,35(m, 1H) 1H), 4.00 (s, 6.88-7.02 (m, 7.03-7.35 (m, 1H)) 2H) , 2H) , 3H) , 2H), 2H), 3H), 7,48 (s, 7.48 (s, 46 46th c₂h₅ c ₂ h ₅ H H 4-C₆H₅ 4-C ₆ H ₅ N N A-tipas Type A 107-109 0,56-2,34(m, 2,40-2,60(m, 1H) , 4,20 (s, 6,05-7,70(m, 1H) , 8,05 (s, 107-109 0.56-2.34 (m, 2.40-2.60 (m, 1H), 4.20 (s, 6.05-7.70 (m, 1H), 8.05 (s) , 11H) 2H) , 2H) , 9H) , 1H) 11H) 2H), 2H), 9H), 1H) Z 2,65(s, 7,95 (s, Z 2.65 (s, 7.95 (s, 47 47 c₂h₅ c ₂ h ₅ H H 4 - C₆H₅ 4 - C ₆ H ₅ CH CH A-tipas Type A 169-170 0,66-2,28(m, 1H), 2,45-2, 3,96 (s, 2H) , 12H) 169-170 0.66-2.28 (m, 1H), 2.45-2, 3.96 (s, 2H), 12H) 11H) 72 (m, 6,8 5· 11H) 72 (m, 6.8 5 · , 2,01(s 2H) , -7,63(m, , 2.01 (s 2H), -7.63 (m, 48 48 c₂h₅ c ₂ h ₅ H H 4- 4- CH CH A-tipas Type A aliejus o,85(t, 3H, oil o, 85 (t, 3H, J=7) , J = 7), 1,29 (s, 1.29 (s,

ižo11treasury11

C₂H₅ H ižo- H C₃H₇ C ₂ H ₅ H i-HC ₃ H ₇

H- H CsHuH- H CsHu

H- HH-H

CsHn c₂h₅ hCsHn c ₂ h ₅ h

CH₃ ch₃ CH ₃ ch ₃

C4H9 9H) , 0,90-1,90 (m, 8H),C 4 H 9 9 H), 0.90-1.90 (m, 8H),

2,41(d, d, 1H, J=14,10), 2,49(d, d, 1H, J=14.5),2.41 (d, d, 1H, J = 14.10), 2.49 (d, d, 1H, J = 14.5),

4,23 (s, 2H) , 7,07 (d, 2H, J=8,3), 7,28(d, 2H, J=8,3),4.23 (s, 2H), 7.07 (d, 2H, J = 8.3), 7.28 (d, 2H, J = 8.3),

7,96 (s, 1H) , 7.96 (s, 1H), 8,01(s, 1H) 8.01 (s, 1H) 4- CH tret C₄H₉ 4- CH tret C ₄ H ₉ A-tipas Type A 132-133 132-133 0,67-2,83(m, 9H) , 4,08 (s, 6,97-7,53(m, 1H) 0.67-2.83 (m, 9H), 4.08 (s, 6.97-7.53 (m, 1H) 14H) , 1,32 (s 2H) , 6H) , 7,58(s, 14H), 1.32 (s 2H), 6H), 7.58 (s, 4-C1 N 4-C 1 N A - tipas A - type 91-92 91-92 0,95(d, 3H, 0.95 (d, 3H, J=7), 0,97(d, J = 7), 0.97 (d,

3H, J=7), 1,17-2,93(m, 10H), 4,12(d, 1H, J=14), 4,41(d, 1H, J=14),3H, J = 7), 1.17-2.93 (m, 10H), 4.12 (d, 1H, J = 14), 4.41 (d, 1H, J = 14),

6,87-7,40(m, 4H), 7,97(s, 1H) , 8,13 (s, 1H)6.87-7.40 (m, 4H), 7.97 (s, 1H), 8.13 (s, 1H)

4-C1 N A-tipas aliejus o,86(t, 3H, J=6,8),4-C1 N A-type oil o, 86 (t, 3H, J = 6.8),

0,90-1,98(m, 14h), 2,38(d, d, 1H, J=13,4; 9,3) , 2,46(d, d, 1H, J=13,4),0.90-1.98 (m, 14h), 2.38 (d, d, 1H, J = 13.4; 9.3), 2.46 (d, d, 1H, J = 13.4) ,

2,57 (s, 1H) , 2,23(s, 2H) , 7,06(d, 2H, J=8,3) 7,22(d, 2H, J=8,3) , 7,97 (s, 1H) , 8,08(s, 1H)2.57 (s, 1H), 2.23 (s, 2H), 7.06 (d, 2H, J = 8.3) 7.22 (d, 2H, J = 8.3), 7.97 (s, 1H), 8.08 (s, 1H)

4-C14-C1

CH A-tipas 92-95CH A-Type 92-95

0,87(t, 3H, J=6,8),0.87 (t, 3H, J = 6.8),

1,05-1,95(m, 14H0, 2,43(d, d, 1H, J=13,7; 10,3) , 2,569d, d, 1H, J=13,7;1.05-1.95 (m, 14H0, 2.43 (d, d, 1H, J = 13.7; 10.3), 2.569d, d, 1H, J = 13.7;

4,4) , 3,47 (s, 1H) , 3,99 (s, 2H) , 6,94 (s, 1H) , 7,05(d, 2H, J=8,3) , 7,06 (s, 1H) , 7,22 (d, 2H, J=8,3) , 7,48 (s, 1H)4.4), 3.47 (s, 1H), 3.99 (s, 2H), 6.94 (s, 1H), 7.05 (d, 2H, J = 8.3), 7.06 (s, 1H), 7.22 (d, 2H, J = 8.3), 7.48 (s, 1H)

CH B-tipas 138 -140 0,57-0,98(m, 3H) ,CH B-type 138 -140 0.57-0.98 (m, 3H),

0,98-2,17 (s, 1H), 4,03 (s, 2H), 6,83; 7,03(m, 6H),0.98-2.17 (s, 1H), 4.03 (s, 2H), 6.83; 7.03 (m, 6H),

7.68(s, 1H)7.68 (s, 1H)

H- 4-C1 N CsHnH-4-C1 N CsHn

CH₃ 4 - C₆H₅ NCH ₃ 4 - C ₆ H ₅ N

CH₃ 4 - C₆H_s NCH ₃ 4 - C ₆ H _s N

A-tipas aliejus 0,88(t, 3H, J=6,8),Type A oil 0.88 (t, 3H, J = 6.8),

1,00-1,94(m, 14H), 2,31(m, 2H) , 3,70 (s, 1H), 4,05(d, 1H, J=13,7), 4,26(d, 1H, J=13,7), 4,26(d, 1H, J=13,7), 6,89(d, 2H,1.00-1.94 (m, 14H), 2.31 (m, 2H), 3.70 (s, 1H), 4.05 (d, 1H, J = 13.7), 4.26 ( d, 1H, J = 13.7), 4.26 (d, 1H, J = 13.7), 6.89 (d, 2H,

J=8,3) , 7,117(d, 2H,.J = 8.3), 7.117 (d, 2H,).

,3), 7,99(s, 1H), 8,15(s, 1H), 3), 7.99 (s, 1H), 8.15 (s, 1H)

A-tipas 122-124 0,63 (s, 3H) , l,02(s, 3H) , 1,10-2,13(m, 4H) , 2,47 (s, 3H) , 3,62 (s, 1H) , 4,23 (s, 2H), 7,10-7,73(m, 9H),Type A 122-124 0.63 (s, 3H), 1.02 (s, 3H), 1.10-2.13 (m, 4H), 2.47 (s, 3H), 3.62 ( s, 1H), 4.23 (s, 2H), 7.10-7.73 (m, 9H),

7,97 (s, 1H) , 8,17(s, 1H)7.97 (s, 1H), 8.17 (s, 1H)

B-tipas 116-118 0,77(s,3H), 0,98(s, 3H),Type B 116-118 0.77 (s, 3H), 0.98 (s, 3H),

CH₃ CH ₃

CH₃ ižo G₃H₇ ch₃ ch₃ CH ₃ Treasure G ₃ H ₇ ch ₃ ch ₃

HH

H ižo C₃H₇ h-c₄hH io C ₃ H ₇ hc ₄ h

HH

1,10-2,80 (s, 5H) , 2,33(d, 1H, J=9), 2,98(d, 1H, J=9)1.10-2.80 (s, 5H), 2.33 (d, 1H, J = 9), 2.98 (d, 1H, J = 9)

3,88 (s, 1H), 4,33 (s, 2H) , 7,07-7,73(m, 9H), 7,97(s, 1H) , 8,25 (s, 1H)3.88 (s, 1H), 4.33 (s, 2H), 7.07-7.73 (m, 9H), 7.97 (s, 1H), 8.25 (s, 1H)

0,80 (s, 3H) , 1,03 (s, 3H) ,0.80 (s, 3H), 1.03 (s, 3H),

1.12- 2,08(m, 4H), 2,37 (s, 3H) , 2,43 (s, 1H) , 4,00 (s, 2H), 6,88-7,78(m, 12H)1.12-2.08 (m, 4H), 2.37 (s, 3H), 2.43 (s, 1H), 4.00 (s, 2H), 6.88-7.78 (m, 12H)

0,85 (s, 3H) , 1,03 (s, 3H) ,0.85 (s, 3H), 1.03 (s, 3H),

1.13- 2,77(s, 5H), 2,30(d, 1H, J=9), 2,95(d, 1H, J=9) 3,60(s, 1H) 4,18(s, 2H),1.13-2.77 (s, 5H), 2.30 (d, 1H, J = 9), 2.95 (d, 1H, J = 9) 3.60 (s, 1H) 4.18 (s, 2H),

6,90~7,87(m, 12H)6.90 ~ 7.87 (m, 12H)

0,97 (d, 3H, J=7) , 1,00(d, 3H, J=7), 1,23-2,53(m,0.97 (d, 3H, J = 7), 1.00 (d, 3H, J = 7), 1.23-2.53 (m,

10H), 3,90(d, 1H, J=14), 4,17(d, 1H, J=14),10H), 3.90 (d, 1H, J = 14), 4.17 (d, 1H, J = 14),

6,90-7,43(m, 6H), 7,53(s, 1H)6.90-7.43 (m, 6H), 7.53 (s, 1H)

0,62 (s, 3H), 1,01 (s, 3H) , 1,27(s, 9H), 1,17-2,00(m, 2H) , 3,50 (s, 1H) , 4,22 (s, 2H) , 7,00 (d, 2H, J=8,4) , 7,25(d, 2H, J=8,4) , 7,92 (s. 1H), 8,12(s, 1H)0.62 (s, 3H), 1.01 (s, 3H), 1.27 (s, 9H), 1.17-2.00 (m, 2H), 3.50 (s, 1H), 4 , 22 (s, 2H), 7.00 (d, 2H, J = 8.4), 7.25 (d, 2H, J = 8.4), 7.92 (s. 1H), 8.12 (s, 1H)

CH A-tipas 167-168 0,78(s, 1H), l,02(s, 3H), 1,29 (s, 9H), 1,14-2,10(m, 5H), 2,14-2,57(m, 2H),CH Type A 167-168 0.78 (s, 1H), 1.02 (s, 3H), 1.29 (s, 9H), 1.14-2.10 (m, 5H), 2.14 -2.57 (m, 2H),

2,40 (s, 1H) , 3,97 (s, 2H) , 6,96(d, 2H, J=8,4), 7,59(s, 1H)2.40 (s, 1H), 3.97 (s, 2H), 6.96 (d, 2H, J = 8.4), 7.59 (s, 1H)

CH₃ 4-C₆H_s CH A-tipas 162-163CH ₃ 4 -C ₆ H _s CH A-Type 162-163

CH₃ 4-C₆H₅ CH B-tipas 165-167CH ₃ 4-C ₆ H ₅ CH B-Type 165-167

4-C1 CH A-tipas aliejus4-C1 CH A-type oil

CH₃ 4 - N tretC₄H₉ CH ₃ 4 - N tretC ₄ H ₉

A-tipas 107-108A-type 107-108

CK₃ 4· tret C4H9 ižo- 4-C1 N C₃H₇ ižo- 4-C1 N C₃H₇ ižo- 4-C1 CH C₃H₇ CK ₃ 4 · tret C4H9 io-4-C1 NC ₃ H ₇ io-4-C1 NC ₃ H ₇ io-4-C1 CH C ₃ H ₇

B-tipas aliejusType B oil

A-tipas 102-103A-type 102-103

A-tipas 146-147A-type 146-147

4-C1 N B-tipas 120-1214-C1 N B-Type 120-121

0,60-3,17(m, 15H) , 3,43 (s, 1H) , 4,20(s, 2H) , 6,92(d, 2H, J=8) , 7,15 (d, 2H, J=8) 7,87 (s, 1H) , 8,07(s, 1H)0.60-3.17 (m, 15H), 3.43 (s, 1H), 4.20 (s, 2H), 6.92 (d, 2H, J = 8), 7.15 (d, 2H, J = 8) 7.87 (s, 1H), 8.07 (s, 1H)

0,70-2,33 (m, 15H) , 3,47 (s, 1H), 3,97(d, 1H, J=14), 4,38(d, 1H, J=14), 6,73(d, 2H, J=8), 7,10(d, 2H, J=8) 7,93 (s, 1H) , 8,10 (s, 1H)0.70-2.33 (m, 15H), 3.47 (s, 1H), 3.97 (d, 1H, J = 14), 4.38 (d, 1H, J = 14), 6, 73 (d, 2H, J = 8), 7.10 (d, 2H, J = 8) 7.93 (s, 1H), 8.10 (s, 1H)

0,83-2,43(m, 16H), 3,73(d, 1H, J=14), 4,22(d, 1H, J=14), 6,60-6,27(m, 6H), 7,53(s, 1H)0.83-2.43 (m, 16H), 3.73 (d, 1H, J = 14), 4.22 (d, 1H, J = 14), 6.60-6.27 (m, 6H) ), 7.53 (s, 1H)

0,70-2,63 (m, 15H) , 3,70 (s, 1H), 4,33(s, 2H), 7,00(d, 2H, J=8) , 7,27(d, 2H, J=8) 8,07(s, 1H), 8,40(s, 1H)0.70-2.63 (m, 15H), 3.70 (s, 1H), 4.33 (s, 2H), 7.00 (d, 2H, J = 8), 7.27 (d, 2H, J = 8) 8.07 (s, 1H), 8.40 (s, 1H)

4-C1 CH A-tipas aliejus 0,57-2,67(m, 17H), 3,05(s, 1H), 3,95(s, 2H), 6,68~7,25(m, 6H), 7,38 (s, 1H)4-C1 CH Type A Oil 0.57-2.67 (m, 17H), 3.05 (s, 1H), 3.95 (s, 2H), 6.68 ~ 7.25 (m, 6H) ), 7.38 (s, 1H)

H-C4H9 4-C1 4- A-tipas 94-95 0,63!2,43(m, 17H), 3,67(s,H-C4H9 4-C1 4- A-type 94-95 0.63! 2.43 (m, 17H), 3.67 (s,

IH), 3,95(d, IH, J=14),1H), 3.95 (d, 1H, J = 14),

3,25 (d, IH, J=14), 6,77(d,3.25 (d, 1H, J = 14), 6.77 (d,

H, J=8), 7,07(d, 2H, J=8),H, J = 8), 7.07 (d, 2H, J = 8),

7,83 (s, IH) , 8,02 (s, IH)7.83 (s, 1H), 8.02 (s, 1H)

H H-C₄H₉ 4-C1 ižo- H 4-C1H HC ₄ H ₉ 4 -C 1 i-H 4 -C 1

C₄H₉ ižo- H C₄H₉ C ₄ H ₉ i-HC ₄ H ₉

NC1NC1

N B-tipas aliejus 0,60~2,33(m, 16H),N B-type oil 0.60 ~ 2.33 (m, 16H),

2,90-3,20 (m, IH), 3,30 (s, IH) , 3,22 (s, 2H), 6,88(d, 2H, J=8), 7,12(d, 2H, J=8), 7,83 (s, IH), 8,02(s, IH)2.90-3.20 (m, 1H), 3.30 (s, 1H), 3.22 (s, 2H), 6.88 (d, 2H, J = 8), 7.12 (d, 2H, J = 8), 7.83 (s, 1H), 8.02 (s, 1H)

N A-tipas aliejus 0,78 (d, 3H, J=6), 0,88(d,N Type A oil 0.78 (d, 3H, J = 6), 0.88 (d,

3H, J=6), 1,07-2,27(m, 9H), 2,33-2,67(m, 3H), 4,22(s, 2H), 7,00(d, 2H, J=9),3H, J = 6), 1.07-2.27 (m, 9H), 2.33-2.67 (m, 3H), 4.22 (s, 2H), 7.00 (d, 2H, J = 9),

7,2 (d, 2H, J=9), 7,93 (s,7.2 (d, 2H, J = 9), 7.93 (s,

IH) , 8,05 (s, IH)1H), 8.05 (s, 1H)

4-C1 CH A-tipas aliejus 0,81(d, 3H, J=6), 0,88(d,4-C1 CH Type A Oil 0.81 (d, 3H, J = 6), 0.88 (d,

3H, J=6), l,03~2,10(m, 9H), 2,26-2,70 (m, 2H) , 3,88 (s, IH), 4,00 (s, 2H) ,3H, J = 6), 1.03 ~ 2.10 (m, 9H), 2.26-2.70 (m, 2H), 3.88 (s, 1H), 4.00 (s, 2H) ,

6,70-7,30 (m, 6H), 7,46 (s, IH)6.70-7.30 (m, 6H), 7.46 (s, 1H)

71 71 H H H H 4-C1 4-C1 N N A-tipas Type A aliejus oil 0,60~3,63(m, 17H), 2,80(s, IH) , 6,23 (s, 2H) , 7,07(d, 2H, J=8), 7,27(d, 2H, J=8) 8,00 (s, IH) , 8,13 (s, IH) 0.60 ~ 3.63 (m, 17H), 2.80 (s, 1H), 6.23 (s, 2H), 7.07 (d, 2H, J = 8), 7.27 (d, 2H, J = 8) 8.00 (s, 1H), 8.13 (s, 1H) 72 72 i z ome i z ome c₂h₅ c ₂ h ₅ 4-C1 4-C1 N N A-tipas Type A mišinys blend 0,57-1,02(m, 6H), 0.57-1.02 (m, 6H), ras a ch₃ ras a ch ₃ 72 -a 72-a l,12~2,55(m, 9H), 3,55-3,67 (2s, IH) , 4,20 (s, 1.12 ~ 2.55 (m, 9H), 3.55-3.67 (2s, 1H), 4.20 (s, i z ome i z ome 75-b 75-b 2H) 2H) ras b ras b ch₃ ch ₃ N N A-tipas Type A 98-101 98-101 6,95 (d, 2H, J=9), 7,18(d, 6.95 (d, 2H, J = 9), 7.18 (d, c₂h₅ c ₂ h ₅ 2H, J=9) , 7,92 (s, IH) , 8,12(s, IH) 2H, J = 9), 7.92 (s, 1H), 8.12 (s, 1H) 73 73 i z ome i z ome c₂h₅ c ₂ h ₅ 4-C1 4-C1 N N B-tipas Type B mišinys blend 0,67-1,05(m, 6H), 0.67-1.05 (m, 6H), ras a ch₃ ras a ch ₃ a 73-a the 73-a 1,05-3,12(m, 9H), 3,77-3,92 (2s, IH) , 4,35 (s, 1.05-3.12 (m, 9H), 3.77-3.92 (2s, 1H), 4.35 (s, i z ome i z ome b 75-b b 75-b 2H) 2H) ras b ras b ch₃ ch ₃ 4-C1 4-C1 N N 117-119 117-119 6,95(d, 2H, J=8), 7,18(d, 6.95 (d, 2H, J = 8), 7.18 (d, C₂H₅ C ₂ H ₅ 2H, J=8) , 7,90 (s, IH) , 8,15(2s, IH) 2H, J = 8), 7.90 (s, 1H), 8.15 (2s, 1H) 74 74 i z ome i z ome c₂h₅ c ₂ h ₅ 4-C1 4-C1 CH CH B - tipas B - type mišinys blend 0,63-1,08(m, 6H), 0.63-1.08 (m, 6H), ras a ch₃ ras a ch ₃ 74-b 74-b l,08~3,07(m, 9H), 3,33(s, IH) , 4,12 (s, 2H) 1.08 ~ 3.07 (m, 9H), 3.33 (s, 1H), 4.12 (s, 2H) i z ome i z ome 74 - a 74 - a 6,80-7,30 (m, 6H), 7,70 (s, 6.80-7.30 (m, 6H), 7.70 (s, ras b c₂h₅ ras bc ₂ h ₅ ch₃ ch ₃ 4-C1 4-C1 CH CH B - tipas B - type 122-127 122-127 IH) IH) 75 75 ch₃ ch ₃ ch₃ ch ₃ 4- 4- N N B - tipas B - type aliejus oil 0,77 (s, 3H) , 1,01 (s, 3H) , 0.77 (s, 3H), 1.01 (s, 3H), tret- tertiary l,28(s, 9H) , 1,39-2,ll(m, 1.28 (s, 9H), 1.39-2, 11 (m, -c₄h₉ -c ₄ h ₉ 5H), 2,12-2,54(m, 2H), 3,78(b, s, IH) , 4,31 (s, 2H), 6,95(d, 2H, J=8,4), 7,20 (d, 2H, J=8,4) , 7,88 (s IH), 8,14(s, IH) 5H), 2.12-2.54 (m, 2H), 3.78 (b, s, 1H), 4.31 (s, 2H), 6.95 (d, 2H, J = 8.4), 7.20 (d, 2H, J = 8.4), 7.88 (s 1H), 8.14 (s, 1H) 76 76 ch₃ ch ₃ ch₃ ch ₃ 4- 4- CH CH 132 -133 132-133 0,84 (s, 3H), 1,06 (s, 3H), 0.84 (s, 3H), 1.06 (s, 3H), tret - tert - 1,30 (s, 9H) , 1,43-3,10(m, 1.30 (s, 9H), 1.43-3.10 (m,

~c₄h₉ ~ c ₄ h ₉ 8H) , 4 1H) , 7 7,19 (s J=8,4) 8H), 4H), 7 7.19 (s J = 8.4) , 13 (s, 2H), 6,87 (s, ,01(d, 2H, 8,4), , 1H), 7,29(d, 2H, , 7,73(s, 1H) , 13 (s, 2H), 6.87 (s,, 01 (d, 2H, 8.4), , 1H), 7.29 (d, 2H, , 7.73 (s, 1H) 2 lentelė Table 2 Mišinio Forma Aktyvus Nr. ingradien- tas o, 5 Mixture Form Active No. ingraday it oh, 5 Skystas ar % kietas nešiklis Liquid or% solid carrier Emulgatorius % % Emulsifier 7 Pavyzdys milteliai 50 Example powder 50 diatominė 42 žemė diatomic 42 land ligninsulforūgš- 5 ties druska alkilsulforūgš- 3 ties druska lignin sulphonic acid 5 salt alkyl sulphonic acid 3 at the salt 8 Pavyzdys milteliai 8 Example powder bentonitas 40 bentonite 40 ligninsulforūgš- 7 ties druska lignin sulphonic acid 7 to salt 9 Pavyzdys emulguoja- 10 mas koncentratas Example 9 Emulsifiable Concentrate cikloheksa- 15 nonas ksilenas cyclohexanone xylene P AB 10 P AB 10 10 Pavyzdys emulguoja- 40 mas koncentratas Example 10 Emulsifiable Concentrate cikloheksa- 15 nonas ksilenas 25 cyclohexanone xylene 25 kalcio dodecilben- 8 zosulfatas calcium dodecylbenzosulfate 8

butilfenolpoli- 12 etilenglikolio eteris lentelėbutylphenolpoly- 12 ethylene glycol ether table

Junginio Nr. Compound No. Koncentracija, min.d. Concentration, min.d. Apsauginis efektas, Protective effect, 1 1 125 125 100 100 2 2 125 125 100 100 3 3 125 125 95 95 4 4 125 125 100 100 5 5 125 125 100 100 6 6th 125 125 100 100 7 7th 125 125 95 95 8 8th 125 125 95 95 9 9th 125 125 100 100 10 10th 125 125 100 100 11 11th 125 125 100 100

125 125 90 90 125 125 100 100 125 125 100 100 125 125 95 95 125 125 100 100 125 125 95 95 125 125 100 100 125 125 100 100 125 125 50 50 125 125 100 100 125 125 100 100 125 125 100 100 125 125 100 100 125 125 100 100 125 125 100 100 125 125 100 100 125 125 100 100 125 125 100 100 125 125 100 100 125 125 100 100 125 125 100 100 125 125 100 100 125 125 100 100 125 125 100 100 125 125 100 100 125 125 100 100 125 125 100 100 125 125 100 100

125 125 100 100 125 125 100 100 125 125 100 100 125 125 95 95 125 125 100 100 125 125 100 100 125 125 95 95 125 125 100 100 125 125 100 100 125 125 100 100 125 125 100 100 125 125 100 100 125 125 100 100 125 125 75 75 125 125 100 100 125 125 100 100 125 125 100 100 125 125 100 100 125 125 100 100 125 125 100 100 125 125 100 100 125 125 100 100 125 125 100 100 125 125 100 100 125 125 100 100 125 125 100 100 125 125 100 100 125 125 100 100

68 68 125 125 100 100 69 69 125 125 100 100 70 70 125 125 100 100 71 71 125 125 100 100 72 72 125 125 100 100 73 73 125 125 100 100 74 74 125 125 100 100 75 75 125 125 100 100 76 76 125 125 100 100 triadimefonas triadimephone 125 125 100 100

(žinoma)*(of course)*

Kontrolė 0 (be apdorojimo) * triadimefonas yra komercinis produktas ir kaip aktyvų ingradientą įjungia junginį pagal formulę:Control 0 (no treatment) * Triadimefon is a commercial product and, as an active ingredient, activates a compound of the formula:

lentelėtable

Junginio Nr. Compound No. Koncentracija, mln.d. Concentration, million d. Apsauginis efektas, % Protective effect,% 1 1 125 125 100 100 2 2 125 125 100 100 3 3 125 125 100 100 4 4 125 125 100 100 5 5 125 125 100 100 6 6th 125 125 100 100 7 7th 125 125 100 100

8 8th 125 125 100 100 9 9th 125 125 100 100 10 10th 125 125 100 100 11 11th 125 125 100 100 12 12th 125 125 100 100 13 13th 125 125 100 100 14 14th 125 125 100 100 15 15th 125 125 100 100 16 16th 125 125 100 100 17 17th 125 125 100 100 triadimefonas (žinomas)* triadimefon (known) * 125 125 100 100 Kontrolė (be apdorojimo) Control (no processing) 0 0

lentelėtable

Junginio Nr. Koncentracija, mln.d. Apsauginis efektas, %Compound No. Concentration, million d. Protective effect,%

1 1 125 125 100 100 2 2 125 125 95 95 3 3 125 125 100 100 4 4 125 125 95 95 5 5 125 125 100 100 6 6th 125 125 100 100 7 7th 125 125 100 100 8 8th 125 125 95 95 9 9th 125 125 100 100 10 10th 125 125 100 100 11 11th 125 125 100 100 12 12th 125 125 95 95

125 125 100 100 125 125 100 100 125 125 100 100 125 125 100 100 125 125 95 95 125 125 100 100 125 125 100 100 125 125 100 100 125 125 100 100 125 125 100 100 125 125 100 100 125 125 70 70 125 125 100 100 125 125 100 100 125 125 100 100 125 125 100 100 125 125 100 100 125 125 100 100 125 125 100 100 125 125 100 100 125 125 100 100 125 125 100 100 125 125 100 100 125 125 100 100 125 125 100 100 125 125 100 100 125 125 100 100 125 125 100 100

125 125 100 100 125 125 100 100 125 125 100 100 125 125 100 100 125 125 100 100 125 125 100 100 125 125 100 100 125 125 100 100 125 125 90 90 125 125 100 100 125 125 100 100 125 125 100 100 125 125 95 95 125 125 100 100 125 125 100 100 125 125 100 100 125 125 100 100 125 125 90 90 125 125 100 100 125 125 90 90 125 125 90 90 125 125 100 100 125 125 100 100 125 125 100 100 125 125 100 100 125 125 100 100 125 125 100 100 125 125 100 100

69 69 125 125 100 100 70 70 125 125 100 100 71 71 125 125 100 100 72 72 125 125 100 100 73 73 125 125 100 100 74 74 125 125 100 100 75 75 125 125 90 90 76 76 125 125 90 90 triadimefonas (žinomas)* triadimefon (known) * 125 125 100 100 Kontrolė (be apdorojimo) Control (no processing) 0 0

lenteltables

1 1 500 500 100 100 2 2 500 500 100 100 3 3 500 500 90 90 4 4 500 500 80 80 5 5 500 500 100 100 6 6th 500 500 100 100 7 7th 500 500 70 70 8 8th 500 500 70 70 9 9th 500 500 100 100 10 10th 500 500 100 100 11 11th 500 500 85 85 12 12th 500 500 80 80 13 13th 500 500 100 100 14 14th 500 500 100 100

500 500 90 90 500 500 100 100 500 500 80 80 500 500 100 100 500 500 100 100 500 500 100 100 500 500 100 100 500 500 65 65 500 500 100 100 500 500 90 90 500 500 85 85 500 500 100 100 500 500 90 90 500 500 100 100 500 500 100 100 500 500 60 60 500 500 100 100 500 500 85 85 500 500 100 100 500 500 100 100 500 500 75 75 500 500 100 100 500 500 100 100 500 500 100 100 500 500 100 100 500 500 70 70 500 500 60 60 500 500 100 100

500 500 100 100 500 500 100 100 500 500 100 100 500 500 100 100 500 500 95 95 500 500 70 70 500 500 70 70 500 500 80 80 500 500 80 80 500 500 85 85 500 500 100 100 500 500 100 100 500 500 80 80 500 500 100 100 500 500 60 60 500 500 100 100 500 500 65 65 500 500 100 100 500 500 100 100 500 500 80 80 500 500 60 60 500 500 85 85 500 500 60 60

lentelėtable

Junginio Nr. Koncentracija, min.d. Apsauginis efektas, %Compound No. Concentration, min.d. Protective effect,%

1 1 125 125 100 100 2 2 125 125 100 100 3 3 125 125 100 100 4 4 125 125 100 100 5 5 125 125 100 100 6 6th 125 125 100 100 7 7th 125 125 100 100 8 8th 125 125 100 100 9 9th 125 125 100 100 10 10th 125 125 100 100 11 11th 125 125 100 100 12 12th 125 125 100 100 13 13th 125 125 100 100 14 14th 125 125 95 95 15 15th 125 125 90 90 16 16th 125 125 100 100 17 17th 125 125 100 100 Kontrolė (be apdorojimo) Control (no processing) 0 0

lentelėtable

Junginio Nr. Compound No. Koncentracija, mln.d. Concentration, million d. Apsauginis efektas, % Protective effect,% 1 1 125 125 100 100 2 2 125 125 100 100 3 3 125 125 100 100 4 4 125 125 95 95 5 5 125 125 100 100 9 9th 125 125 100 100 13 13th 125 125 95 95 14 14th 125 125 90 90 15 15th 125 125 95 95 16 16th 125 125 100 100 18 18th 125 125 100 100 23 23rd 125 125 100 100 24 24th 125 125 100 100 29 29th 125 125 95 95 30 30th 125 125 90 90 33 33 125 125 100 100 37 37 125 125 100 100 38 38 125 125 100 100 50 50 125 125 100 100 63 63 125 125 100 100 69 69 125 125 100 100 71 71 125 125 100 100 Kontrolė (be apdorojimo) Control (no processing) 0 0 0 0

lentelėtable

Junginio Nr. Compound No. Koncentracija, mln.d. Concentration, million d. Apsauginis efektas, % Protective effect,% 1 1 125 125 100 100 2 2 125 125 95 95 3 3 125 125 100 100 4 4 125 125 95 95 5 5 125 125 100 100 9 9th 125 125 100 100 13 13th 125 125 100 100 14 14th 125 125 100 100 15 15th 125 125 95 95 16 16th 125 125 100 100 18 18th 125 125 100 100 23 23rd 125 125 100 100 24 24th 125 125 100 100 29 29th 125 125 100 100 30 30th 125 125 100 100 33 33 125 125 100 100 37 37 125 125 100 100 38 38 125 125 100 100 50 50 125 125 100 100 63 63 125 125 100 100 69 69 125 125 100 100 71 71 125 125 100 100 Kontrolė (be apdorojimo) Control (no processing) 0 0 0 0

lentelėtable

Junginio Nr. Compound No. Koncentracija, min.d. Concentration, min.d. Apsauginis efektas, % Protective effect,% 1 1 125 125 100 100 2 2 125 125 95 95 3 3 125 125 100 100 4 4 125 125 95 95 5 5 125 125 100 100 9 9th 125 125 100 100 13 13th 125 125 95 95 14 14th 125 125 95 95 15 15th 125 125 100 100 16 16th 125 125 100 100 18 18th 125 125 100 100 23 23rd 125 125 100 100 24 24th 125 125 100 100 29 29th 125 125 100 100 30 30th 125 125 100 100 33 33 125 125 100 100 37 37 125 125 100 100 38 38 125 125 100 100 50 50 125 125 100 100 63 63 125 125 100 100 69 69 125 125 100 100 71 71 125 125 100 100 Kontrolė (be apdorojimo) Control (no processing) 0 0 0 0

lentelėtable

Junginio Nr. Compound No. Koncentracija, mln.d. Concentration, million d. Apsauginis efektas, % Protective effect,% 1 1 125 125 100 100 2 2 125 125 95 95 3 3 125 125 100 100 4 4 125 125 95 95 5 5 125 125 100 100 9 9th 125 125 100 100 13 13th 125 125 95 95 14 14th 125 125 95 95 15 15th 125 125 100 100 16 16th 125 125 100 100 18 18th 125 125 100 100 23 23rd 125 125 100 100 24 24th 125 125 100 100 29 29th 125 125 100 100 30 30th 125 125 100 100 33 33 125 125 100 100 37 37 125 125 100 100 38 38 125 125 100 100 50 50 125 125 100 100 63 63 125 125 100 100 69 69 125 125 100 100 71 71 125 125 100 100 Kontrolė (be apdorojimo) Control (no processing) 0 0 0 0

lentelėtable

Junginio Nr. Compound No. Dozė, kg/ha Application rate, kg / ha Apsauginis efektas, % Protective effect,% 1 1 125 125 100 100 2 2 125 125 100 100 3 3 125 125 100 100 4 4 125 125 100 100 5 5 125 125 100 100 9 9th 125 125 100 100 13 13th 125 125 90 90 14 14th 125 125 90 90 15 15th 125 125 90 90 16 16th 125 125 100 100 18 18th 125 125 100 100 23 23rd 125 125 100 100 24 24th 125 125 95 95 29 29th 125 125 100 100 30 30th 125 125 100 100 33 33 125 125 100 100 37 37 125 125 100 100 38 38 125 125 100 100 50 50 125 125 100 100 63 63 125 125 100 100 69 69 125 125 100 100 71 71 125 125 100 100 Kontrolė (be apdorojimo) Control (no processing) 0 0 0 0

lentelėtable

Junginio Nr. Compound No. Dozė, kg/ha Application rate, kg / ha Apsauginis efektas, % Protective effect,% 1 1 125 125 100 100 2 2 125 125 100 100 3 3 125 125 100 100 4 4 125 125 100 100 5 5 125 125 100 100 9 9th 125 125 100 100 13 13th 125 125 100 100 14 14th 125 125 95 95 15 15th 125 125 90 90 16 16th 125 125 100 100 18 18th 125 125 100 100 23 23rd 125 125 100 100 24 24th 125 125 95 95 29 29th 125 125 100 100 30 30th 125 125 100 100 33 33 125 125 100 100 37 37 125 125 100 100 38 38 125 125 100 100 50 50 125 125 100 100 63 63 125 125 100 100 69 69 125 125 100 100 71 71 125 125 100 100 Kontrolė (be apdorojimo) Control (no processing) 0 0 0 0

lentelėtable

Junginio Nr. Compound No. Dozė, kg/ha Application rate, kg / ha Apsauginis efektas, % Protective effect,% 1 1 125 125 100 100 2 2 125 125 90 90 3 3 125 125 100 100 4 4 125 125 85 85 5 5 125 125 100 100 9 9th 125 125 100 100 13 13th 125 125 80 80 14 14th 125 125 80 80 15 15th 125 125 85 85 16 16th 125 125 100 100 18 18th 125 125 100 100 23 23rd 125 125 100 100 24 24th 125 125 85 85 29 29th 125 125 100 100 30 30th 125 125 100 100 33 33 125 125 95 95 37 37 125 125 100 100 38 38 125 125 100 100 50 50 125 125 100 100 63 63 125 125 100 100 69 69 125 125 100 100 71 71 125 125 100 100 Kontrolė (be apdorojimo) Control (no processing) 0 0 0 0

lentelėtable

Junginio Nr. Compound No. Dozė, kg/ha Application rate, kg / ha Apsauginis efektas, % Protective effect,% 1 1 125 125 100 100 2 2 125 125 98 98 3 3 125 125 100 100 4 4 125 125 90 90 5 5 125 125 100 100 9 9th 125 125 100 100 13 13th 125 125 90 90 14 14th 125 125 95 95 15 15th 125 125 85 85 16 16th 125 125 100 100 18 18th 125 125 100 100 23 23rd 125 125 100 100 24 24th 125 125 95 95 29 29th 125 125 100 100 30 30th 125 125 100 100 33 33 125 125 95 95 37 37 125 125 100 100 38 38 125 125 100 100 50 50 125 125 100 100 63 63 125 125 100 100 69 69 125 125 100 100 71 71 125 125 100 100 Kontrolė (be apdorojimo) Control (no processing) 0 0 0 0

lentelėtable

Junginys The compound Koncentracija, dal/mln Concentration, parts per million Apsauginis efektas, % Protective effect,% 7,8 7.8 15,6 15.6 1 1 100 100 100 100 3 3 75 75 100 100 9 9th 100 100 100 100 16 16th 85 85 90 90 55 55 90 90 ⁹⁵⁹⁵ A* (žinomas) A * (known) 30 30th 70 70 B** (žinomas) B ** (known) 30 30th 50 50 C (žinomas) C (known) 20 20th 65 65 D (žinomas) D (known) 0 0 10 10th

* Junginys A:* Compound A:

**** Junginys D:**** Compound D:

lenteltables

Junginys The compound Koncentracija, dal/mln Concentration, parts per million Apsaugin Protect 13 13th 500 500 100 100 15 15th 500 500 90 90 48 48 500 500 100 100 49 49 500 500 100 100 E*(žinomas) E * (known) 500 500 15 15th F* *(žinomas) F * * (known) 500 500 10 10th G* * * (žinomas) G * * * (known) 500 500 30 30th H****(žinomas) H **** (known) 500 500 40 40

* Junginys E:* Compound E:

* Junginys F:* Compound F:

** Junginys G:** Compound G:

*** Junginys H:*** Compound H:

lentelėtable

Junginio Nr. Compound No. Koncentracija, min.d. Concentration, min.d. Apsauginis efektas, % Protective effect,% 1 1 125 125 100 100 2 2 125 125 100 100 3 3 125 125 100 100 4 4 125 125 99 99 5 5 125 125 100 100 9 9th 125 125 100 100 13 13th 125 125 95 95 14 14th 125 125 90 90 15 15th 125 125 95 95 16 16th 125 125 100 100 18 18th 125 125 100 100 23 23rd 125 125 100 100 24 24th 125 125 95 95 29 29th 125 125 100 100 30 30th 125 125 100 100 33 33 125 125 100 100 37 37 125 125 100 100 38 38 125 125 100 100 50 50 125 125 100 100 63 63 125 125 100 100 69 69 125 125 100 100 71 71 125 125 100 100 Kontrolė Control 0 0 0 0

(be apdorojimo) lentelė(without processing) table

Junginio Nr. Compound No. Koncentracija, mln.d. Concentration, million d. Apsauginis efektas, % Protective effect,% 1 1 125 125 100 100 2 2 125 125 100 100 3 3 125 125 100 100 4 4 125 125 95 95 5 5 125 125 100 100 9 9th 125 125 100 100 13 13th 125 125 100 100 14 14th 125 125 95 95 15 15th 125 125 95 95 16 16th 125 125 100 100 18 18th 125 125 100 100 23 23rd 125 125 100 100 24 24th 125 125 100 100 29 29th 125 125 100 100 30 30th 125 125 100 100 33 33 125 125 100 100 37 37 125 125 100 100 38 38 125 125 100 100 50 50 125 125 100 100 63 63 125 125 100 100 69 69 125 125 100 100 71 71 125 125 100 100 Kontrolė (be apdorojimo) Control (no processing) 0 0 0 0

Claims

DEFINITION OF INVENTION

1. A fungicidal mixture containing the active ingredient and additives, wherein the active ingredient is a 1- (azol-1-ylmethyl) -2-benzylcyclopentanol derivative having the formula:

wherein R ¹ and R ² are hydrogen or C ₁ -C ₅ alkyl, provided that one of these radicals is not hydrogen;

X _n is: hydrogen and at the 4-position is fluorine, chlorine, bromine, C ₁ -C ₄ alkyl, phenyl; or chlorine at the 2-position and 4-position; or fluorine at position 2 and chlorine at position 4;

A is a nitrogen atom or a -CH- group at the following ratio (% w / w) of the active ingredient: 3 to 50, the additives being the remainder.