JPS6041603A - Fungicide for agricultural and horticultural use - Google Patents

Abstract

PURPOSE:To provide an agricultural and horticultural fungicide containing 4,5,6, 7-tetrachlorophthalide and a specific imidazole derivative as active components, and exhibiting remarkable synergistic controlling effect especially to rice blast. CONSTITUTION:The objective agricultural and horticultural fungicide contains (A) 4,5,6,7-tetrachlorophthalide and (B) the compound of formula I )[R<1> is group of fomrula II or formula III (R<2> is lower alkyl, cycloalkyl, phenyl, or lower alkyl-substituted phenyl; R<3> is H or lower alkyl; m is 1 or 2; n is 0 or 1); A is group of formula IV or formula V (R<4>-R<6> are H or alkyl); X is halogen, lower alkyl or lower alkoxy; p is 0, 1 or 2] as active components. The fungicide has high remedying effect to rice blast in addition to the remarkably preventive effct. The rate of application can be reduced to 1/2-1/4 of the conventional fungicide resulting in the elimination of the problem of residual fungicide in the environment.

Description

[Detailed description of the invention]

The present invention is based on 4,5,6,7-tetrachlorophyll? t lido (
(hereinafter referred to as "compound A") and the general formula R, cycloalkyl, phenyl, or lower alkyl-substituted phenyl, and R3 (R4 represents a hydrogen atom or alkyl), independently a hydrogen atom or fcil' i, all alkyl groups], xi, t
-・Rogen atom, lower alkyl di, I; straddle lower alkyl 1/di・(indicates ■)It, L' 0,
1 or 2] with imidazole derivatives, which are used as active ingredients, are used as fungicides for rice fungicides, especially rice blast #1, which is the most common 4P disease of rice. On 1'j, Matsube hits a hit with E's Aizume effect. ('t 1-51 t?-(+tL).
Currently, it is widely known that it is used as a control agent for rice blast S''r.
(See Publication No. 62594). This compound Δ is human, animal, and fish f1
It is highly safe against insects, has excellent preventive effects and residual effects, and is the most useful among the many commercially available blast control agents. One of the δ agents τ! be. However, 11″, nri!
IA (') Imochi n (!'j 'Ir R kj
le actionll￥(',!Saiko(,r];714'',:
(7) Limited to only a few,

[7. l,)4
'617ir"!pi) Infection of rice cultivation V to a monster +1γ oI conversion f- -℃sil has no effect at all, and in the late stage of makai-haku raw stone 97"i, i(7j+, , if you do so, you will be stuck in the middle of nowhere, and the secondary damage will occur.
Because of this, there are problems such as the number of times it has been used is f, and there are 11 prefectures and 7 t/). The present inventors have discovered that 11C compounds have
5') 3'; Taking advantage of II effect and residual effect 1, 17 points were compensated for by the above points, and the 1st frf officer was immediately n
l! , 'j Excision of the bar - j 111 and the scales were tested. σ) Any one of 4 mino + so A and the compound 11 shown in the above general formula (1) to the paste piece and the compound
・Distributing 5/'H, -iruko 2(and J- means rice blast control (τ-(; ~ shows very high 1~lj 11γ efficacy7, and these effects are due to the effect of each active ingredient. Jlj X=IBfI
The agricultural and horticultural 1 Not only is he an author, but he also has a high level of healing (effects as well)
L. It has been completed as an ideal rice blast control agent that can be used by reducing the dose of conventional compounds to 2 to 1/4, and has no problems from browning. It is. The compound of general formula (1) used in the fa composition of the present invention can be produced by the method described in Table of Contents. In the reaction (7), the corresponding carbamoyl chloride and imidazole are mixed together as reaction components, and acetone, dimedylformamide 1-, dimethylchloride, and sulfoxide are reacted in a solvent inert to the reaction, including potassium carbonate, sodium carbonate, and water. The reaction is carried out in the presence of ρ1, water, IXt, hysodium, pyridine, and IXt. Next is the invention? Teitei(゛・In =sre2)−β′
Regarding the preparation of the compound of formula (1)■□'! ;
:'j 1"'"'show. 11! ! Preparation Example 1 (Compound 1', sl; 08) N-2
-(3-methylbutine-1-.1l)-11-α-n-
-j'Pe' Rubenzyl force/Simole chloride 80r (0,287 mol)'? i-Bath in Luno Ami F200r+g in Renotilf': ,・rmittf;t
8tJS' (1,17 mol) i;-, LbiL'2
r Potassium 1 [J[IY (0.72 mol) to force 1
1λte1;”l'4'l' l-dakaga7(]~81
] was heated for 201j. Outside the end of the reaction, 1 water []]
Or-Mold: Join!・Rue 7 f 4'+Q out shift'j
After that, 4'4'>II"I k j,", 'l water i I engineering r: Y dl thorium dried, 1 toluene fC distilled off?
6. Decompression, -", +': q L Te light blue liquid (D
it's Y/FJ 55f (-1'1.p, 195-
200'C/' 3 mmHq). Production Example 2 (Compound +!+163) N-1-cyclohexenyl-N-α-n-butylbenzylcarbamoyl chloride a49 ((1,029 mol)
was dissolved in dimethylformamide 50-, imidazole 10F (0,147 mol) and potassium carbonate IC1 (
0,072 mol) was added thereto and heated at 80° C. for 1 hour. After the reaction, the mixture was poured into water, extracted with toluene, concentrated, and recrystallized from toluene and n-hexano. . Representative examples of imidazole derivatives that can be used in the present invention are as follows. In addition, the compound number is also referred to in the following Examples and Test Examples. fg 1 Terra 34 C1,Q' n4) 15573CT(2 1 35' -C-CAH9(sec) n111.567
0a+2 ■ 37” -fC411q(nec) n,,1.
5514a+2 1 41 ・' -C-C4F+9(oec) nDl, 5
62950 Self 0 ″ ″ r・]', ”615446
(:11s54'-c+-;2- (,] nfi,' 1.
582055"'0 - nr, 1.5732 sen, u7(n) 62"-("[T-#r,.T), 86-87℃
C/positive (9(11) 65'-CH-' m, p, 94=95℃73,
Cl30Q "n"51.5595C7115 76'-CI+-' m, p, 82-87℃78a1
．． oO・” 1.5568ny) 87BTO#! I; 0″1.5679 CH 1 93 ' -(1(, -f-TI7--C-C 17
(i) r+ n L 547596# ″-〇 n's' 1.5528 [:83 102 ″-CR2-C)+2- On” 1.56
67103 ・tsu ntsu'1.5822 110 Ct-C)-' -guteI=:] m, p. 1
434-105℃ 112 hi nr, '1-5617 117C OO'''' n211.55, '+5]] To formulate the horticultural fungicide of the present invention, the active ingredients should be weighed using the conventional scales. By adding carriers and various auxiliary agents, powders (including LIL type powders), irrigation agents, flowable agents,
It can be used in any desired form such as a fine powder. ``Composition'' of active ingredients according to the present invention!+11, B H
It is common practice to mix 0.5 to 3 parts of imitazole to 1 part of compound A, but depending on the application conditions and 1 part of compound A. Ir1. as f
ii4. The combination 7+11 can be modified and used as appropriate. In addition to the active ingredients of Kisukemon, other fungicides, insecticide 1111,
It can be used in combination with a degreaser, degreaser, etc. Next, we will show five examples of the r''! gardening and gardening agents of the present invention. Example 1 Hydration Ha11 15 parts of compound A Ratio t!n 119207'lI, 17 parts of white carbon, polyA chisiniger 1/nonylphenol ether 29i(,') Kuninsulfone
3 parts of 8 resin and 1 part of clay (mix in total ribbon mill, A/Mizer C redundant A:) and wait for wettable powder. Dilute this water agent d water to 500-50 times and get 10 ares! 7100~200t +7)
Spray at 171 cups. Example 2 1.5 parts of powder compound A, 101.5 parts of compound 1, 2 parts of white carb, 0.3 parts of PAP (physical property improver) and 94.7 parts of clay were placed in a ribbon mixer and mixed.
Pulverize thoroughly with an atomizer to obtain a powder. This powder is directly sprayed on the rice crop before or after the outbreak of rice blast at a rate of 3 to 4 Ky per 10 acres using an appropriate spraying device. Example 3 Flowable Agent 15 parts of Compound A, 820 parts of Compound +1, 1.5 fil+ of polyoxyethylene (alkyl allyl ether), 6 parts of 4-rivinyl alcohol, and 5 parts of water were uniformly mixed to make a flowable t74). This flowable agent I [Original 4 trenches Karoroi #-t yJ
: If the rare T is 8 to 30 times higher, 9100 lights to 4 tons per 10 ares will be air-ripened, or 500 to 30 times.
00 times diluted to 10 ares (Hl-200j'
, it is possible to run and spray all over the ground. Test example 1 Field trial F/H with rice potato leaf control. Appearance 9 m in diameter. Rice with soil ax [8] 1.
Asahi)'s 3-leaf raccoon 1゛17 - non-use, preventive bird sickness r (1"
i J・People treatment effect vc, r* was carried out. Chemical dispersion number F Mi (Ti 1 to 1 n1 rule J-
Dilute the water 11161j to a predetermined concentration on the turntable to 341°.
``t'fi'J cloth (, fc. Wr i'i゛+ 4
”: 1 layer was prepared in advance on Matemil agar medium -, -+i
'? = stop (7tei3daineimochi1) pyric
A spore suspension (Microscope, 150x magnification, 1 x 1 J'J 50 spores) of J'J 50 spores was inoculated. In the preventive efficacy test, the sacrificial agent was sprayed using the above method, and one day later, it was placed in a greenhouse and stored for 24 hours in a 7-foot chamber at 24°C. Poster effect test r)
Then, 24 hours after being inoculated with the disease bacteria, rice potato f7 seedlings were inoculated with the seedlings using the distribution method, and as in the preventive effect test, the seedlings were stimulated to develop in a greenhouse. Release E'i n! Is the third test a preventive effect test? 60 days after inoculation with n bacteria, the number of rice blasts per leaf on the third leaf (%i'i n'5.7 Control value @ compared to ward
) was issued p:. The results are shown in Table 1. Note 1) I Immediately US-Benzyl 0.0-Di 4 Sotulo Bilvospo 11f71 Knee 1 Not Containing 1 Old 1! This is the f-mouth side. N12) ','' in parentheses!
Show k. Test example 2 Rice blast control effect: 0 Kawaguchidai control effect: Kenshimon Benlate 1° Hydrating agent 20 (Ichibaibai 7'' as agent) 24 times n:j lil l;:,, li'f extinguisher rf
Did you do it? +r'Q-7 (product scale: Puzanishiki) was sown in rows at the cutting edge using the 7+1 J-removal test r1 method. In order to measure the effect under multiple conditions, 1, % Bl, we added (1 weighed rice (
Item f1:・Lisa gonk) to rice rice mochi1:'i t''(
Iii's 1st child was released from school by Park I, and from this point on he was 4 years old.
Potato jl-j rl Kawa 1 child has 3 stains 5'ζ 1 naturally grown on the rice of regular seedlings. ? h agent 1fk cloth 1i'i 'J ＆l 1 ni 3'+shite H': S':! L/ 7j 4'1 supply r (2, 1 section of prescribed concentration liquid of drug (113, 1m23 consecutive)) To!7
The mixture was sprayed twice with a small automatic sprayer. The first spraying was carried out when the initial moon spots began to appear on the lower leaves 2, 8
At the leaf stage, the second application of 17C was carried out 6 days after the first application. Development fq p, y inspection tj: tn 2 times q agent spraying (7)
After 7 days, 14 days, and 21 days, the residual efficacy of each drug was investigated. The investigation method was to investigate rice blast n spot dead area ratio @) and calculate the control value of each chemical using the following formula. The red color is shown in Table 2. Note 1) R: DIJP47iC1-x is a commercially available mouthcide containing S, S-diphenyl dithiophosphate. Note 2) The numbers in parentheses indicate the average number of mullets 1nn withered and dead in the area where the mulberry was sprayed. 9? r1 out to Komajin Kitamon Chemical, ``ni+i'l R:i-
s 4'e IJ times Ube 1ryo lda,' deletion ceremony meeting Jindai Jsuj person dialect 1111 Toyama F ``1[
, h, :t? Mountain 11. l: ``1'!
11 (・) / り小 ” し る : 1',, いL i'”l+'l lj+
f j i', 1 toi tl I):,'','(2, name of the invention (,'j, 1, (Sien)'', month 1 z゛之 IY+ ii'
ni', (S, :(, i'11i 1st) Ro Akane "11th and b') IXI Ill", Q, i4. 'l' IM
! ! I'l kllll・ha east・:1.1;1 (Naka Riko 1me 11・1・1.) 11'll'4 l' II
frlltf+ i4+,,u; Q! ! 11;°
``Pa''''＋i Ju S: II ,,, , ?1゜・[,6JMr.
I 21 frll phase 11th Hiba) 5, Supplementary 111 notice 1lf 1 (Platinum: lO0 Sode 11 no Yo 1 Xiang Ming 1, 1: Invention of 1.
'lll positive internal medicine 11 ;'JS 10 LI's, lg, combination, 15)
iJl'i, 22 to 22゜J~ru2) i4;
"Yes" and answered no. ro) No. 20 gi gf45 '<工(') [chemical D''
l! ”) A to J'; “Compound A” and extraction 11-
To do. 4) 24Bo Sadashita 21t 51r, "r 2
r''Q A, 15 jijj J as ``compound'A
Part 15,” said the oil stop [7 ma! . s) a+'422 ts j-"' r in the second row from the bottom
'1' Z+l l j 久r ')ry7+FLe
J and i11 faces! t-f. 1, no, ten

Claims (1)

[Claims] 4.5,6.7-tetrachlorophthalide and the general formula R group,
represents a cycloalkyl group, a phenyl group or a lower alkyl-substituted phenyl group, and R5 independently represents a hydrogen atom or an alkyl group], XI represents a rogen atom, a lower alkyl group or a lower alkoxy group, So,
and p is 0.1 or 2] as an active ingredient.