KR810000238B1 - Agricultural and horticultural fungicidal compositions - Google Patents

Agricultural and horticultural fungicidal compositions Download PDF

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KR810000238B1
KR810000238B1 KR7601543A KR760001543A KR810000238B1 KR 810000238 B1 KR810000238 B1 KR 810000238B1 KR 7601543 A KR7601543 A KR 7601543A KR 760001543 A KR760001543 A KR 760001543A KR 810000238 B1 KR810000238 B1 KR 810000238B1
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이지로오 세도
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기구지 우라지
구미아이 가가구 고오교 가부시끼 가이샤
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    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N27/00Biocides, pest repellants or attractants, or plant growth regulators containing hydrocarbons

Abstract

Agricultural and horticultural fungicidal compositions were prepd. Thus, benzanilide of formula I(R = alkyl, alkoxy; X = halogen, alkyl) was mixed at the ratio of 3 : 1 or 1 : 3 with one of the organic phosphorous compds. of formula A(R = alkyl), B (R = alkyl),C(R = alkyl; X = halogen. nitro or cyano. m = 0-3), D (R = alkyl; X = oxygen or sulfur, etc.) and E(R = R1 = alkyl) to give title compositions.

Description

농원예용 살균조성물Agricultural Horticulture Sterilization Composition

본 발명은 다음 일반식(Ⅰ)로 표시되는 벤즈아닐리드(benzanilide)와 다음 일반식(A), (B), (C), (D) 및 (E)로 표시되는 군에서 선택한 유기인화합물과를 함유하는 것을 특징으로 하는 농원예용 살균조성물에 관한 것이다.The present invention provides a benzanilide represented by the following general formula (I) and an organophosphorous compound selected from the group represented by the following general formulas (A), (B), (C), (D) and (E); It relates to a horticultural sterilizing composition comprising a.

[일반식][General Formula]

Figure kpo00001
Figure kpo00001

상기 일반식(Ⅰ)에서,In the general formula (I),

R은 알킬기 또는 알콕시기, X는 할로겐, 알킬기이고 상기 (A)식에서 R은 알킬기, (B)식에서 R은 알킬기, (C)식에서 R은 알킬기, X는 할로겐, 니트로기 혹은 시아노기, m은 0-3이며 (D)식에서 R은 알킬기, X는 산소 혹은 유황원자, R'는

Figure kpo00002
(여기서 X는 니트로기 혹은 메틸티오기),R is an alkyl or alkoxy group, X is a halogen, an alkyl group and R is an alkyl group in formula (A), R is an alkyl group in formula (B), R is an alkyl group in formula (C), X is a halogen, nitro group or cyano group, m is 0-3 and (D) where R is an alkyl group, X is an oxygen or sulfur atom, and R '
Figure kpo00002
(Where X is a nitro group or a methylthio group),

Figure kpo00003
Figure kpo00003

(여기서 X는 할로겐, n은 0-3)이고 (E)식에서 R 및 R'는 알킬기를 표시한다.Wherein X is halogen and n is 0-3 and R and R 'in the formula (E) represent an alkyl group.

본 발명은 상기 일반식으로 표시되는 벤즈아닐리드를 보다 적은 사용 약량(藥量)으로 식물의 병해를 방제하는 것을 목적하고, 협력제의 조색(操索)을 진행시킨 결과 완성시킨 것이다. 상기의 일반식으로 표시되는 벤즈아닐리드와 상기의 일반식의 유기인화합물과를 혼합 조제하여 사용하는 경우, 특히 벼문고병(紋枯病)에 대한 방제효과가 극히 높고, 이 혼합물의 각성분을 각각 단독으로 사용하는 경우에 나타나는 방제효과의 단순한 종합보다도 훨씬 큰 것을 발견하고, 상세히 연구한 결과, 상기 일반식에 나타난 벤즈아닐리드와 유기인화합물과의 사이에 소위 상승작용을 발견한 것이다.This invention aims at controlling the disease of a plant with the use amount of benzanilide represented by the said general formula in a lesser dosage, and was completed as a result of advancing the cooperative agent. In the case of mixing and using benzanilide represented by the above general formula and the organophosphorus compound of the above general formula, the control effect is particularly high against rice blight disease, and each component of the mixture is It was found that much larger than a simple synthesis of the control effect when used alone, and studied in detail, the so-called synergy between benzanilide and the organophosphorus compound shown in the general formula.

상기의 벤즈아닐리드는, 벼문고병, 수병(銹病), 리조구토니아등의 토양병해등에 대하여 높은 방제효과를 갖지만, 보다 경제적인 방제를 고려할 때, 가능한한 사용약량을 절감하는 것이 바람직하다.The benzanilide has a high control effect against soil diseases such as rice paddy disease, water bottle, risogonia, etc., but in consideration of more economical control, it is desirable to reduce the amount of use as much as possible.

한편, 일반식으로 나타난 유기인화합물은, 농업용 살충제 혹은 도열병(稻熱病)용 살균제로서 사용되고 있는데, 벼문고병에 대해서도 어느정도의 방제효과를 갖는 것이 알려져 있다. 그러나 실용적으로는 충분한 효과를 갖는다고 하기에는 곤란하다.On the other hand, the organophosphorus compound represented by the general formula is used as an insecticide for agriculture or as a fungicide for thermal diseases, and it is known to have some control effect against rice paddy disease. However, practically, it is difficult to say that it has sufficient effect.

본 발명자들은, 상기의 일반식으로 나타내는 벤즈아닐리드와 상기 일반식으로 나타내는 유기인화합물을 혼합사용하는 경우의 상승효과에 의해서, 벤즈아닐리드를 단독으로 사용하는 경우에 비해서 훨씬 낮은 농도로 벼문고병을 방제하는 것이 가능한 것을 발견하여 본 발명을 완성함에 이르렀다. 그밖에, 본 발명의 혼합물은 상기의 일반식으로 표시된 벤즈아닐리드의 단제(單劑)로서는 방제가 불가능한 도열병, 깨엽고병(葉枯病)등의 병해를 방제하는 것이 가능하다.MEANS TO SOLVE THE PROBLEM The present inventors control rice paddy disease at much lower concentration compared with the case where benzanilide is used alone by the synergistic effect when mixing benzanilide represented by said general formula and organophosphorus compound represented by the said general formula. The inventors have found that it is possible to complete the present invention. In addition, the mixture of the present invention can control diseases such as heat diseases, sesame leaves, and the like, which are impossible to control with the monosaccharide of benzanilide represented by the above general formula.

상기 일반식으로 표시된 벤즈아닐리드로서As benzanilide represented by the above general formula

화합물 A 3'-메틸-2-클로로벤즈아닐리드(m.p. 124℃)Compound A 3'-methyl-2-chlorobenzanilide (m.p. 124 ° C)

화합물 B 3'-메톡시-2-브로모벤즈아닐리드(m.p. 162-164℃)Compound B 3'-methoxy-2-bromobenzanilide (m.p. 162-164 ° C)

화합물 C 3'-이소프로폭시-2-요오도벤즈아닐리드(m.p. 94-96℃)Compound C 3'-isopropoxy-2-iodobenzanilide (m.p. 94-96 ° C)

화합물 D 3'-에틸-2-메틸벤즈아닐리드(m.p. 125℃)Compound D 3'-ethyl-2-methylbenzanilide (m.p. 125 ° C)

화합물 E 3'-이소프로폭시-2-메틸벤즈아닐리드(m.p. 92-94℃)Compound E 3'-Isopropoxy-2-methylbenzanilide (m.p. 92-94 ° C)

화합물 F 3'-sec-부톡시-2-메틸벤즈아닐리드(m.p. 75-77℃)Compound F 3'-sec-butoxy-2-methylbenzanilide (m.p. 75-77 ° C)

화합물 G 3'-sec-부톡시-2-요오도벤즈아닐리드(m.p. 86-87℃)Compound G 3'-sec-butoxy-2-iodobenzanilide (m.p. 86-87 ° C)

등을 들 수 있다.Etc. can be mentioned.

또, 상기 일반식으로 표시된 유기인화합물로서Moreover, as an organophosphorus compound represented with the said general formula

화합물 Ⅰ S-벤질-O,O-디이소프로필포스포로티올레이트,Compound I S-benzyl-O, O-diisopropylphosphothiolate,

화합물 Ⅱ O-에틸-S,S-디페닐포스포로디티올레이트,Compound II O-ethyl-S, S-diphenylphosphorodithiolate,

화합물 Ⅲ O-에틸-O-(P-니트로페닐)페닐포스포노티오네이트,Compound III O-ethyl-O- (P-nitrophenyl) phenylphosphonothionate,

화합물 Ⅳ O,O-디메틸-O-(4-니트로-m-톨릴)포스포로티오에이트,Compound IV O, O-dimethyl-O- (4-nitro-m-tolyl) phosphothioate,

화합물 Ⅴ O,O-디메틸-O-(2-이소프로필-4-메틸-6-피리미딜)포스포로티오에이트,Compound V O, O-dimethyl-O- (2-isopropyl-4-methyl-6-pyrimidyl) phosphothioate,

화합물 Ⅵ O,O-디메틸-O-(3,5,6-트리클로로-2-피리딜)포스포로티오에이트,Compound VI O, O-dimethyl-O- (3,5,6-trichloro-2-pyridyl) phosphothioate,

화합물 Ⅶ O,O-디메틸-O-2-클로로-1-(2,4-티클로로페닐)비닐포스페이트,Compound Ⅶ O, O-dimethyl-O-2-chloro-1- (2,4-thichlorophenyl) vinylphosphate,

화합물 Ⅷ O,O-디메틸-S-α-에톡시카아보닐벤질포스포로디티오에이트,Compound VII O, O-dimethyl-S-α-ethoxycarboylbenzylphosphorodithioate,

등을 열거할 수 있다.And the like.

이들의 유효성분에 활석, 고령토, 점토, 규조토, 벤토나이트, 화이트카아본, 식물가루, 크실렌, 톨루엔, 미크로핵사논, 메틸에틸케톤, DMF, DMSO, 알킬벤젠, 알킬벤젠술폰산염류, 리그닌폰산염류(Ligninsulfonate), 폴리옥시에틸렌, 알킬알릴에테르, 폴리옥시에틸렌솔비탄 모노라우레이트, 등의 담체희석제, 계면활성제, 분산제, 보조제 등을 배합하여 분제, 수화제 유제, 유동현탁액, 또는 미립제, 미립제F, 입제로 제제하여 적당한 농도로 희석하여 살포하든가 직접 사용한다.These active ingredients include talc, kaolin, clay, diatomaceous earth, bentonite, white carbon, plant powder, xylene, toluene, micronucleanone, methyl ethyl ketone, DMF, DMSO, alkylbenzene, alkylbenzenesulfonates, and ligninfonates ( Ligninsulfonate), polyoxyethylene, alkylallyl ether, polyoxyethylene sorbitan monolaurate, and the like, by mixing a carrier diluent, a surfactant, a dispersant, an auxiliary agent, and the like, a powder, a hydrating emulsion, a fluid suspension, or a fine granule F. Use it as a granule, dilute it to a suitable concentration, or spray it directly.

다음에 실시예를 들지만, 본 발명은 실시예의 범위에 한정되는 것은 아니다. 또 화합물 번호는 상기를 참조한다. 실시예에서 %는 중량 100분율을 표시한다.Although an Example is given to the following, this invention is not limited to the range of an Example. In addition, the compound number is referred to the above. In the examples,% indicates the weight percentage.

[실시예 1. 분제]Example 1. Powder

화합물 A 3%, 화합물 Ⅰ 2%, 활석 및 점토의 균등혼합물 95%를 균일하게 혼합 분쇄하여 분제로 한다.3% of Compound A, 2% of Compound I, and 95% of an equal mixture of talc and clay are mixed and ground to obtain a powder.

[실시예 2. 수화제]Example 2. Hydration

화합물 B 25%, 화합물 Ⅱ 25%, 규조토 45%, 디나프틸메탄디술폰산의 소오다염 3%, 리그닌술폰산소오다 2%를 균일하게 혼합분쇄하여 수화제로 한다.25% of Compound B, 25% of Compound II, 45% of diatomaceous earth, 3% of soda salt of dinaphthylmethane disulfonic acid, and 2% of soda lignin sulfonic acid were mixed and ground to obtain a hydrate.

[실시예 3. 입제]Example 3. Granulation

화합물 G 3%, 화합물 Ⅲ 3%, 화이트카아본 3%, 벤토나이트 20%, 활석 47%, 점토 20%, 알킬알릴술폰산소오다 1%, 리그닌술폰산소오다 3%를 균일하게 혼합 분산하여 소량의 물을 가하여 연합(練合)하고, 조립(造粒)가공후 건조하여 입제로 한다.3% of compound G, 3% of compound III, 3% of white carbon, 20% of bentonite, 47% of talc, 20% of clay, 1% of alkylallyl sulfonic acid sodium, 1% of sodium lignin sulfonic acid It is combined with water, granulated, dried and granulated.

[실시예 4. 유제]Example 4. Emulsion

화합물 D 20%, 화합물 Ⅳ 20%, 시클로헥사논 30%, 크실렌 20%, 폴리옥시에틸렌알킬알릴에테르, 폴리옥시에틸렌솔비탄모노라울레이드, 알킬알릴술폰산소오다의 혼합물 10%를 균일하게 용해하여 유제로 한다.20% of compound D, 20% of compound IV, 30% of cyclohexanone, 20% of xylene, 10% of a mixture of polyoxyethylene alkylallyl ether, polyoxyethylene sorbitan monolaurate, and alkylallyl sulfonic acid sodium hydroxide Emulsion.

[실시예 5. 유동현탁액]Example 5 Flow Suspension

화합물 E 25%, 화합물 Ⅲ 25%, 에틸렌글리콜모노부틸에테르 10%, 폴리옥시에틸렌노릴에놀에테르, 폴리옥시에틸렌솔비탄모노부틸레이트 및 알킬알릴술포네이트의 혼합물 8%, 콜로이드성 함수규산알미늄 3% 및 물 29%를 혼합한 후, 습식분쇄를 행하여 균일한 유동현탁액으로 한다. 다음에 본 발명 농원예용 살균조성물의 효과를 시험예에 의해 표시한다.25% compound E, 25% compound III, 10% ethylene glycol monobutyl ether, 8% mixture of polyoxyethylene noryl enol ether, polyoxyethylene sorbitan monobutylate and alkylallylsulfonate, colloidal hydrous aluminum silicate 3 % And water 29% are mixed, followed by wet grinding to obtain a homogeneous flow suspension. Next, the effect of the agricultural and horticultural sterilizing composition of the present invention is shown by the test example.

[시험예 1][Test Example 1]

직경 15㎝의 백자폿트에 벼묘(품종 : 금남풍) 3그루씩 이식하고, 그의 6-7엽기(葉棄)에 각약제를 턴테이블과 스프레이건을 사용하여, 1m거리에서 3폿트당 20cc를 살포했다. 살포후는 온실속에서 24시간 방치하고, 미리 배양해둔 벼문고 병균을 겨로 중량하며, 벼의 기부(基部)에 접종했다. 접종후 27-28℃, 포화습도의 접종실에 넣고, 7일간 보존후에 병반(病斑)길이를 조사하고 다음 계산식에 의해 방제가를 산출하였다.Three rice seedlings (kind: Geumnam style) were transplanted into a 15cm diameter white pot, and each of them was sprayed 20cc per 3 pots at a distance of 1m using a turntable and a spray gun. did. After spraying, the cells were left in a greenhouse for 24 hours, weighed with rice bran cultured beforehand, and inoculated at the base of rice. After inoculation, the resultant was placed in an inoculation chamber of 27-28 ° C. and saturated humidity, and after storage for 7 days, the length of the lesion was examined, and the control value was calculated by the following formula.

Figure kpo00004
Figure kpo00004

[기험결과][Experience Result]

Figure kpo00005
Figure kpo00005

Claims (1)

다음 일반식(Ⅰ)로 표시되는 벤즈아닐리드와 다음 일반식(A), (B), (C), (D) 및 (E)로 표시되는 군에서 선택한 유기인 화합물과를 3 : 1 내지 1 : 3의 중량비율로 함유하는 것을 특징으로 하는 농원예용 살균조성물.Benzanilide represented by the following general formula (I) and the organophosphorus compound selected from the group represented by the following general formula (A), (B), (C), (D) and (E) are 3: 1-1 : Agricultural horticultural sterilization composition, characterized by containing at a weight ratio of 3.
Figure kpo00006
Figure kpo00006
상기 일반식(Ⅰ)에서,In the general formula (I), R은 알킬기 또는 알콕시기, X는 할로겐, 알킬기이고 상기 (A)식에서 R은 알킬기, (B)식에서 R은 알킬기, (C)식에서 R은 알킬기, X는 할로겐, 니트로기 혹은 시아노기, m은 0-3이며 (D)식에서 R은 알킬기, X는 산소 혹은 유황원자, R'는
Figure kpo00007
(여기서 X는 니트로기 혹은 메틸티오기),
R is an alkyl or alkoxy group, X is a halogen, an alkyl group and R is an alkyl group in formula (A), R is an alkyl group in formula (B), R is an alkyl group in formula (C), X is a halogen, nitro group or cyano group, m is 0-3 and (D) where R is an alkyl group, X is an oxygen or sulfur atom, and R '
Figure kpo00007
(Where X is a nitro group or a methylthio group),
Figure kpo00008
Figure kpo00008
(여기서 X는 할로겐, n은 0-3)이고 (E)식에서 R 및 R'는 알킬기를 표시한다.Wherein X is halogen and n is 0-3 and R and R 'in the formula (E) represent an alkyl group.
KR7601543A 1976-06-23 1976-06-23 Agricultural and horticultural fungicidal compositions KR810000238B1 (en)

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