LT4014B

Fungicidal composition

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.

LT4014B, drawing sheet 1 — Sheet 1 of 10

Term

Term ended

Expired 31 January 2014, 12.6 years ago.

1 claim: 1 independent, 0 dependent

1
IŠRADIMO APIBRĖŽTIS 1.Fungicidinis mišinys, kuriame yra aktyvusis ingredientas ir priedai, besiskiriantis tuo, kad aktyviuoju ingredientų yra 1-(azol-l-ilmetil)-2-benzilciklopentanolio darinys, kurio formulė:kurioje R 1 ir R 2 yra vandenilis arba Ci-C 5 -alkilas, su sąlyga, kad vienas iš šių radikalų yra ne vandenilis;X n yra: vandenilis,o 4-je padėtyje yra fluoras, chloras, bromas, Ci-C 4 -alkilas, fenilas;arba chloras 2-je ir 4-je padėtyje;arba fluoras 2-je padėtyje ir chloras 4-je padėtyje;A yra azoto atomas arba -CH- grupė, esant tokiam komponentų (svorio %) santykiui: aktyvusis ingredientas - 3 4- 50, priedai - likusi dalis.

892 paragraphs in 34 sections, as filed

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.

An azole-based fungicidal mixture is known (NN Melnikov, KV Novožilova, TN Pylova Chimičeskie sredstva zaščity rastenij. Spravočnik, M. Chimija, 1980, p.225).

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 23.03.1987).

However, the indicated fungicidal mixtures exhibit low activity at low concentrations.

The object of the present invention is to increase the fungicidal activity of the mixture. The following examples illustrate a patentable proposal.

example

Preparation of 5- (4-chlorobenzyl) -2,2-dimethyl-1- (1H-1,2,4-triazol-1-ylmethyl) cyclopentanol

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).

example

Preparation of 5- (2,4-dichlorobenzyl) -2,2-dimethyl-1- (1H-imidazol-1-ylmethyl) cyclopentanol

Add 186 ml of anhydrous dimethylformamide and dissolve, under helium atmosphere, 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 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.

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).

Similarly, other compounds of formula I are obtained:

are presented in Table 1.

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).

Of the compounds in the Table, the following are most suitable. 1-3, 5, 9-11, 16, 18.

example

Dust

Three parts by weight of compound 1, 40 parts by weight of clay and 57 parts by weight of talc are mixed and pulverized.

example

Moisturizing powder

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.

example

Granules

Twenty polyoxyethylene

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.

example

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.

Analogously obtained mixtures are shown in Table 2.

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 seedlings 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 of the control (untreated plants). The results are shown in Table 3.

example

One of each of the 3 cup cucumber sprouts grown in unglazed 10 cm diameter cups and in the second leaf stage was treated with 5 ml / cup of sample 4 aqueous suspension. After air-drying, spore brushes were applied to the spores of Sphaerotheca fuliginea 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.

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.

example

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 part of the leaf of the plant, which was grown for three days at 20 ° C in agar medium with the addition of sugar and potato broth. The cups were stored at 20-22 ° C at high humidity. After three days, the spread of disease (as in Example 11) was evaluated. The results are shown in Table 6.

example

Each 10 cm diameter non-glazed cup was planted with 16 rice grains and when the rice sprouts reached a 4-5 leaf stage, they were exposed to the diluted mixture of Example 4. 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.

example

The tests were carried out according to the procedure of Example 11 but using the mixture of Example 6. The results are shown in Table 8.

example

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.

example

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.

example

The tests were carried out according to the procedure of Example 13 but using the mixture of Example 9. The results are shown in Table 11.

example

The tests were carried out according to the procedure of Example 13 but using the mixture of Example 4. The results are shown in Table 12.

example

The tests were carried out according to the procedure of Example 11 but using the mixture of Example 4. The results are shown in Table 13.

example

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.

example

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.

example

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.

example

The tests were carried out according to the procedure of Example 14 but using the mixture of Example 8. The results are shown in Table 17.

example

The tests were carried out according to the procedure of Example 13 but using the mixture of Example 10. The results are shown in Table 18.

example

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.

Such mixtures of the present invention exhibit high fungicidal activity at low concentrations.

table

Physico-chemical properties of compounds of formula I

Jun-R1 R2 Xn A Stereo- Lyd.t. MBR spectrum (CDCl3, δ g of the isomer is C)

No. type

1. CH3 CH3 4-C1 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, 1H) 4.13 (s, 2H) 6.80-7.23 (m, 4H) 7, 83 (s, 1H)

2. CH3 CH3 4-C1 N Type B 113-114 0.82 (s, 3H l, 00 (s, 3H)

1.23-1.93 (m, 4H) ch3 ch3 ch3 ch3

CH3

CH,

4-C1 CH A-Type 113-114

4-C1 'CH B-Type 113-114

4-Br N A-Type 113-114

4-Br N B-Type 113-114

4-Br CH A-Type 113-114

4-Br CH B-Type 113-114

4-FN A-Type 113-114

4-FN B-tiDas 113-114

4-F CH A-Type 113-114

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

3.90 (s, 1H) 4.37 (s, 2H)

7.03 (d, 2H, j = 8) 7.25 (d,

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

8.27 (s, 1H)

0.80 (s, 3H) 1.03 (s, 3H)

1.13-2.93 (m, 8H) 3.97 (s,

2H) 7.02 (s, 2H) 6.80-7.33 (m, 4H) 7.60 (s, 1H)

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)

0.63 (s, 3H) 1.00 (s, 3H)

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,

1H) 8.17 (s, 1H)

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)

0.80 (s, 3H) 1.03 (s, 3H)

1.13-2.53 (m, 8H) 4.00 (s,

2H) 6.80-7.50 (m, 6H) 7.63 (s, 1H)

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)

0.67 (s, 3H) 1.03 (s, 3H)

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,

1H) 8.13 (s, 1H)

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)

0.83 (s, 3H) 1.07 (s, 3H)

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,

1H)

0.87 (s, 3H), 1.03 (s, 3H),

1.17-3.03 (m, 8H), 4.10 (s, 2H), 6.70-7.27 (m, 6H),

7.73 (s, 1H)

0.56 (s, 3H), 1.01 (s, 3H),

0.79- (m, 5H), 2.66 (s, 2H),

3.97 (s, 1H) 4.2 H) 7.2 (s.

2,4- N B-Type Cl2

126-127

CH3 gh3 ch3 ch3

CH3 H

4-C1

H CH3

- Cl

H CH3

4-C1

GH3 H

4-C1

2.4ci2

2.4Gl2

4-C1

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-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)

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),

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)

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),

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 type B oil o, 88 (d, 3H, J = 6.6),

1.05-2.45 (m, 7H),

2.62-2.92 (m, 1H),

3.95-4.25 (m, 1, 1H, OH),

4.31 (s, 2H), 6.98 (d, 2H,

J = 8.8), 7.22 (m. 1.2H,

J = 8.8), 7.95 (s, 1H),

8.26 (s, 1H)

1.10-2.17 (m, 5H), 1.97 (s, 1H), 2.17-2.50 (m, 2H),

2H), 6.68-7.20 (m, 5H),

2.13 ~ 2.47 (m, 2H), 3.33 (s,

1H), 4.00 (d, 1H, J = 14),

4.30 (d, IK, J = 14), 6.88 (d,

HC2H5 4-C1

C2H5 H 4 -C 1

C2H5 C2H5 4 - Cl

C2H5 C2H5 4-C1

C2H5 C2H5 4 - Cl

CH

C2H5 C2Hs 4 - Cl

CH

HC3H7 H 4 -C 1

H H-C3H7 4-C1

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

7.93 (s, 1H), 8.17 (s, 1H)

Type B 76-78 0.67-3.33 (m, 13H), 3.07 (d,

1H, J = 10), 4.13 (d, 1H,

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)

Type B 110-112 0.67 ~ 2.20 (m, 12H), 2.73 (d,

1H, J = 10), 4.15 (s, 1H),

4.30 (s, 2H), 6.95 (d, 2H,

J = 8), 7.20 (d, 2H, J = 8), 7.97 (s, 1H), 8.25 (s, 1H)

Type A 124-126 0.67 ~ 1.07 (m, 6H),

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)

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

1.10-1.97 (m, 8H),

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)

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

1.07-2.50 (m, 11H), 3.33 (s, 1H), 3.90 (d, 1H, J = 14),

4.18 (d, 1H, J = 14),

6.70-7.23 (m, 6H), 7.67 (s, 1H)

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),

7.70 (s, 1H)

A-type 83-85 0.61 ~ 2.26 (m, 13H),

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, 1H), 8.07 (s, 1H) ·

Type A 75-77 0.65 ~ 1.04 (m, 3H),

1.04-2.18 (m, 10H),

2.18-2.48 (m, 2H), 3.70 (s,

1H), 3.98 (d, 1H, J = 14),

4.29 (d, 1H, J = 14), 6.86 (d,

2H, J = 8.4), 7.16 (d, 2H,

H-C 3 H 7 H

J = 8.4), 7.94 (s, 1H),

8.12 (s, 1H)

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)

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

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)

treasury11

C2H5 H i-HC3H7

H- H CsHu

H-H

CsHn c2h5 h

CH3 ch3

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),

4.23 (s, 2H), 7.07 (d, 2H, J = 8.3), 7.28 (d, 2H, J = 8.3),

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)

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) ,

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-C1

CH A-Type 92-95

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;

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-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),

7.68 (s, 1H)

H-4-C1 N CsHn

CH3 4 - C6H5 N

CH3 4 - C6Hs N

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,

J = 8.3), 7.117 (d, 2H,).

, 3), 7.99 (s, 1H), 8.15 (s, 1H)

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)

Type B 116-118 0.77 (s, 3H), 0.98 (s, 3H),

CH3

CH3 of Treasury G3H7 ch3 ch3

H

H io C3H7 hc4h

H

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)

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)

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),

6.90 ~ 7.87 (m, 12H)

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),

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)

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)

CH3 4-C6Hs CH A-Type 162-163

CH3 4-C6H5 CH B-Type 165-167

4-C1 CH A-type oil

CH3 4 - N tretC4H9

A-type 107-108

CK3 4 · tret C4H9 io- 4-C1 NC3H7 ijo- 4-C1 NC3H7 iso-4-Cl CH3H7

Type B oil

A-type 102-103

A-type 146-147

4-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)

0.70-2.33 (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)

0.70-2.63 (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 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- Type A 94-95 0.63-1.43 (m, 17H), 3.67 (s,

1H), 3.95 (d, 1H, J = 14),

3.25 (d, 1H, J = 14), 6.77 (d,

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

7.83 (s, 1H), 8.02 (s, 1H)

H HCl4H9 4-C1 i-H 4-C1

C4H9 Iso-HC4H9

NC1

N type B oil 0,60 ~ 2,33 (m, 16H),

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 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),

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

1H), 8.05 (s, 1H)

4-C1 CH Type A oil 0.81 (d, 3H, J = 6), 0.88 (d,

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, 1H)

<td> 72</td><td>iz ome</td><td>c2h5</td><td>4-C1</td><td>N</td><td>Type A</td><td>blend</td><td>0.57-1.02 (m, 6H),</td>

<td> 73</td><td>iz ome</td><td>c2h5</td><td>4-C1</td><td>N</td><td>Type B</td><td>blend</td><td>0.67-1.05 (m, 6H),</td>

<td> 74</td><td>iz ome</td><td>c2h5</td><td>4-C1</td><td>CH</td><td>B - type</td><td>blend</td><td>0.63-1.08 (m, 6H),</td>

<td></td><td></td><td></td><td>tertiary</td><td></td><td></td><td></td><td>1.28 (s, 9H), 1.39-2, 11 (m,</td>

<td></td><td></td><td>Table 2</td>

<td>Mixture Form Active No. ingraday it oh, 5</td><td>Liquid or% solid carrier</td><td>% Emulsifier</td>

<td>Example powder 50</td><td>diatomic 42 the land</td><td>lignin sulphonic acid 5 salt alkyl sulphonic acid 3 at the salt</td>

<td>Example powder</td><td>bentonite 40</td><td>lignin sulphonic acid 7 to salt</td>

<td>Example 9 Emulsifiable Concentrate</td><td>cyclohexanone xylene</td><td>P AB 10</td>

<td>Example 10 Emulsifiable Concentrate</td><td>cyclohexanone xylene 25</td><td>calcium dodecylbenzosulfate 8</td>

butylphenolpoly- 12 ethylene glycol ether table

<td>Compound no.</td><td>Concentration, min.d.</td><td>Protective effect,</td>

<td>triadimephone</td><td> 125</td><td> 100</td>

(of course)*

Control 0 (no treatment) * Triadimefon is a commercial product and, as an active ingredient, activates a compound of the formula:

table

<td>Compound no.</td><td>Concentration, million d.</td><td>Protective effect,%</td>

<td>triadimefon (known) *</td><td> 125</td><td> 100</td>

<td>Control (no processing)</td><td></td><td> 0</td>

table

Compound no. Concentration, million d. Protective effect,%

<td>triadimefon (known) *</td><td> 125</td><td> 100</td>

<td>Control (no processing)</td><td></td><td> 0</td>

tables

Compound no. Concentration, million d. Protective effect,%

table

Compound no. Concentration, min.d. Protective effect,%

<td>Control (no processing)</td><td></td><td> 0</td>

table

<td>Compound no.</td><td>Concentration, million d.</td><td>Protective effect,%</td>

<td>Control (no processing)</td><td> 0</td><td> 0</td>

table

<td>Compound no.</td><td>Concentration, million d.</td><td>Protective effect,%</td>

<td>Control (no processing)</td><td> 0</td><td> 0</td>

table

<td>Compound no.</td><td>Concentration, min.d.</td><td>Protective effect,%</td>

<td>Control (no processing)</td><td> 0</td><td> 0</td>

table

<td>Compound no.</td><td>Concentration, million d.</td><td>Protective effect,%</td>

<td>Control (no processing)</td><td> 0</td><td> 0</td>

table

<td>Compound no.</td><td>Application rate, kg / ha</td><td>Protective effect,%</td>

<td>Control (no processing)</td><td> 0</td><td> 0</td>

table

<td>Compound no.</td><td>Application rate, kg / ha</td><td>Protective effect,%</td>

<td>Control (no processing)</td><td> 0</td><td> 0</td>

table

<td>Compound no.</td><td>Application rate, kg / ha</td><td>Protective effect,%</td>

<td>Control (no processing)</td><td> 0</td><td> 0</td>

table

<td>Compound no.</td><td>Application rate, kg / ha</td><td>Protective effect,%</td>

<td>Control (no processing)</td><td> 0</td><td> 0</td>

table

<td rowspan="2">The compound</td><td>Concentration, parts per million</td><td>Protective effect,%</td>

<td>A * (known)</td><td> 30</td><td> 70</td>

<td>B ** (known)</td><td> 30</td><td> 50</td>

<td>C (known)</td><td> 20</td><td> 65</td>

<td>D (known)</td><td> 0</td><td> 10</td>

* Compound A:

**** Compound D:

tables

<td>The compound</td><td>Concentration, parts per million</td><td>Protect</td>

<td>E * (known)</td><td> 500</td><td> 15</td>

<td>F * * (known)</td><td> 500</td><td> 10</td>

<td>G * * * (known)</td><td> 500</td><td> 30</td>

<td>H **** (known)</td><td> 500</td><td> 40</td>

* Compound E:

* Compound F:

** Compound G:

*** Compound H:

table

<td>Compound no.</td><td>Concentration, min.d.</td><td>Protective effect,%</td>

<td>Control</td><td> 0</td><td> 0</td>

(without processing) table

<td>Compound no.</td><td>Concentration, million d.</td><td>Protective effect,%</td>

<td>Control (no processing)</td><td> 0</td><td> 0</td>

Contents34

Every citation, both waysCites: the store holds 1 of 2

Citations
Document	Relation	Office	Cited during
GB2180236A	Cites	United Kingdom	Applicant
N. N. MELNIKOV ET AL.: "Chimičeskie sredstva zaščity rastenij", pages: 225	Non-patent	–	Applicant

64 members in 28 offices

This recordMember, by publication datePriority claim18 more offices are in the list below

Priority claims3

Priority claims
Document	Office	Kind	Date
16112687	Japan	A	1987-06-30
62161126	–	–	–
JP19870161126	–	–	–

Members64

Family members, oldest first
Document	Office	Kind
DK588687D0	Denmark	D0	1987-11-10
DK588687A	Denmark	A	1988-05-11
EP0267778A2	European Patent Office (EPO)	A2	1988-05-18
AU8096187A	Australia	A	1988-05-19
BR8706104A	Brazil	A	1988-06-14
IL85428A0	Israel	A0	1988-07-31
IL85428D0	Israel	D0	1988-07-31
MA21204A1	Morocco	A1	1988-10-01
IE880375L	Ireland	L	1988-12-30
CN1030232A	China	A	1989-01-11
HUT47254A	Hungary	A	1989-02-28
JPH0193574A	Japan	A	1989-04-12
EP0267778A3	European Patent Office (EPO)	A3	1989-04-19
AU584530B2	Australia	B2	1989-05-25
KR890012981A	Republic of Korea	A	1989-09-20
ZA878260B	South Africa	B	1989-09-27
KR900003269B1	Republic of Korea	B1	1990-05-12
NZ223444A	New Zealand	A	1990-06-26
US4938792A	United States of America	A	1990-07-03
CS103388A2	Czechoslovakia (until 1993)	A2	1990-12-13
DD289523A5	German Democratic Republic (until 1990)	A5	1991-05-02
US5028254A	United States of America	A	1991-07-02
CS274740B2	Czechoslovakia (until 1993)	B2	1991-10-15
CN1059825A	China	A	1992-04-01
HU206023B	Hungary	B	1992-08-28
US5159118A	United States of America	A	1992-10-27
IL85428A	Israel	A	1992-12-01
JPH0565243A	Japan	A	1993-03-19
EP0267778B1	European Patent Office (EPO)	B1	1993-03-24
AT87309T	Austria	T	1993-04-15
ATE87309T1	Austria	T1	1993-04-15
DE3784999D1	Germany	D1	1993-04-29
CN1020606C	China	C	1993-05-12
DE3784999T2	Germany	T2	1993-07-01
US5239089A	United States of America	A	1993-08-24
RU1837767C	Russian Federation	C	1993-08-30
AR245703A1	Argentina	A1	1994-02-28
JPH0625140B2	Japan	B2	1994-04-06
CA1331006C	Canada	C	1994-07-26
ES2053564T3	Spain	T3	1994-08-01
TR26948A	Türkiye	A	1994-09-12
JPH06263693A	Japan	A	1994-09-20
JPH06279424A	Japan	A	1994-10-04
MD74B1	Republic of Moldova	B1	1994-11-30
JPH06104643B2	Japan	B2	1994-12-21
LV10436A	Latvia	A	1995-02-20
MD74C2	Republic of Moldova	C2	1995-03-31
US5414105A	United States of America	A	1995-05-09
JPH0747565B2	Japan	B2	1995-05-24
LV10744A	Latvia	A	1995-08-20
LTIP1864A	Lithuania	A	1995-08-25
RU2047605C1	Russian Federation	C1	1995-11-10
JPH07108905B2	Japan	B2	1995-11-22
LV10744B	Latvia	B	1995-12-20
LV10436B	Latvia	B	1996-08-20
LT4014BThis record	Lithuania	B	1996-08-26
DK171542B1	Denmark	B1	1996-12-30
MD422C2	Republic of Moldova	C2	1997-04-30
IE74147B1	Ireland	B1	1997-07-02
UA18635A	Ukraine	A	1997-12-25
GEP19981269B	Georgia	B	1998-07-07
GEP19981389B	Georgia	B	1998-11-10
CN1044659C	China	C	1999-08-18
UA27101A1	Ukraine	A1	2000-02-28

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	Event	Code
2014-02-25	Expiry of a patentMK9A	MK9A
2006-11-27	Change of patent ownerPD9A	PD9A

Abstract

Term

CH,

CH,

CH,

CH,

CH,

CH,

CH,

CH,

CH,

CH,

CH,

CH,

CH,

CH,

CH,

CH,

CH,

1H)

1H)

4-C1

4-C1

4-C1

4-C1

CH

CH

H H-C3H7 4-C1

H-C 3 H 7 H

H-H

4-C1

4-C1

H

H

H

NC1

Priority claims3

Members64

Over the term

Events

Numbers

Titles

Classification