KR840000203B1 - Compositions of the plant growth regulator - Google Patents

Compositions of the plant growth regulator Download PDF

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KR840000203B1
KR840000203B1 KR7702206A KR770002206A KR840000203B1 KR 840000203 B1 KR840000203 B1 KR 840000203B1 KR 7702206 A KR7702206 A KR 7702206A KR 770002206 A KR770002206 A KR 770002206A KR 840000203 B1 KR840000203 B1 KR 840000203B1
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phenyl group
carbon atoms
acid
thiadiazol
group substituted
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하르트 루쉬 라인
아른트 프리드리히
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게르하르트 리트케
쉐링 아크티엔 게젤샤프트
페터 호크스
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Abstract

Combinations contg. I (R1=H, C1-3 alkyl; R2=H, C1˜C4 alkyl; R3=C1˜C4 alkyl, cycloalkyl, ph, haloaryl, etc; X=O, S) and a plant-growth regulator are defoliants. Thus, in greenhouse experiments, a combination 50g 1-phenyl-3-(1,2,3-thiadiazol-5-yl)urea and 50g S,S,S-tri-n-butyl-trithiophosphate ester /ha defoliated cotton by 43.5%, whereas the components applied by themselves were 34.8% and 4.4% effective, respectively.

Description

식물 성장 조절용 조성물Plant growth regulation composition

본 발명은 다음 구조식(Ⅰ)의 1,2,3-티아디아졸-5-일우레아 유도체와 기타 식물성장조절제 및 또는 탈엽제와의 혼합물을 함유하는 식물 성장 조절제, 특히 탈엽제 조성물에 관한 것이다.The present invention relates to a plant growth regulator, in particular a defoliant composition, containing a mixture of 1,2,3-thiadiazole-5-ylurea derivative of formula (I) with other plant growth regulators and / or defoliation agents .

Figure kpo00001
Figure kpo00001

상기 구조식에서In the above structural formula

R1은 수소 또는 탄소수 1 내지 3인 알킬이며R 1 is hydrogen or alkyl having 1 to 3 carbon atoms

R2는 수소 또는 탄소수 1 내지 4인 알킬이며R 2 is hydrogen or alkyl having 1 to 4 carbon atoms

R3는 탄소수 1 내지 4인 알킬, 탄소수 5 내지 8인 시클로알킬, 비치환 페닐, 하나이상의 할로겐으로 치환된 페닐, 하나이상의 메틸로 치환된 페닐, 하나이상의 메톡시로 치환된 페닐 또는 하나이상의 니트로로 치환된 페닐이며R 3 is alkyl having 1 to 4 carbons, cycloalkyl having 5 to 8 carbons, unsubstituted phenyl, phenyl substituted with one or more halogens, phenyl substituted with one or more methyls, phenyl substituted with one or more methoxy, or one or more nitros Is phenyl substituted by

X는 산소원자 또는 황원자이다.X is an oxygen atom or a sulfur atom.

본 발명은 식물성장조절제, 특히 식물(예를들면 목화)의 탈엽에 관계되는 조성물에 관한 것으로 이것은 1,2,3-티아디아졸-5-일 우레아 유도체를 다른 성장조절제 및 또는 탈엽제와 혼합하여 제조한다.The present invention relates to a composition for plant growth regulators, in particular for defoliation of plants (eg cotton), which comprises mixing 1,2,3-thiadiazol-5-yl urea derivatives with other growth regulators and / or defoliation agents To prepare.

1,2,3-티아디아졸-5-일-우레아 유도체가 식물의 성장조절제로 이용되는 것은 기지의 사실이다.It is well known that 1,2,3-thiadiazol-5-yl-urea derivatives are used as plant growth regulators.

(참조 : 독일공개명세서제2,234,816호). 그러나 이러한 활성성분만으로는 모든 경우에 충분한 효력을 나타내지는 못한다.(See German Publication No. 2,234,816). However, these active ingredients alone are not sufficient in all cases.

또한 기타 성장조절제 및 탈엽제도 실제적 요구를 완전히 충족시키지는 못하는 것으로 알려졌다.In addition, other growth regulators and defoliators have not been found to fully meet practical needs.

그러므로 본 발명의 목적은 기지의 성장조절제 및 탈엽제보다 더 좋은 효력을 나타내는 식물성장조절제용 제제를 제공하는 것이다.It is therefore an object of the present invention to provide an agent for plant growth regulators which exhibits better efficacy than known growth regulators and defoliants.

본 발명에서는 1,2,3-티아디아졸릴 우레아 유도체로서는 특히 1-페닐-3-(1,2,3-티아디아졸-5-일)-우레아가 적합하게 사용된다.In the present invention, 1-phenyl-3- (1,2,3-thiadiazol-5-yl) -urea is suitably used as the 1,2,3-thiadiazolyl urea derivative.

본 발명의 제제는 기타 활성성분으로서 다음과 같은 성장조절제 및 또는 탈엽제를 포함할 수 있다.The formulation of the present invention may include the following growth regulators and / or defoliants as other active ingredients.

옥신(auxin)Auxin

α-(2-클로로페녹시)-프로피온산, α-나프틸아세트산, 4-클로로페녹시아세트산, β-나프톡시아세트산, 2,4-디클로로페녹시아세트산, 나프틸아세트아미드, 인돌릴-3-아세트산, N-m-톨릴프탈아민산, 인돌릴-3-부티르산, 지베렐린, S,S,S-트리-n-부틸-트리티오포스포르산에스테르, 시토키닌, 2-클로로에틸포스폰산, 2-클로로-9-히드록시플루오렌-9-카복실산, 2-클로로에틸-트리메틸암모늄클로라이드, N,N-디메틸아미노석신산아미드, 2-이소프로필-4-트리메틸암모니오-5-메틸페닐피페리딘-1-카복실산 에스테르 클로라이드, 페닐-이소프로필카바메이트, 3-클로로페닐-이소프로필카바메이트, 에틸-2-(3-클로로페닐카바모일옥시)-프로피오네이트, 말레산히드라지드, 2,3-디클로로이소부티르산, 디-(메톡시티오카보닐)디설파이드, 1,1'-디메틸-4,4'-비피리딜륨-디클로라이드, 3,6-엔독소헥사히드로프탈산, 3-아미노-1,2,4-트리아졸α- (2-chlorophenoxy) -propionic acid, α-naphthylacetic acid, 4-chlorophenoxyacetic acid, β-naphthoxyacetic acid, 2,4-dichlorophenoxyacetic acid, naphthylacetamide, indolyl-3- Acetic acid, Nm-tolylphthalamic acid, indolyl-3-butyric acid, gibberellin, S, S, S-tri-n-butyl-trithiophosphoric acid ester, cytokinin, 2-chloroethylphosphonic acid, 2-chloro- 9-hydroxyfluorene-9-carboxylic acid, 2-chloroethyl-trimethylammonium chloride, N, N-dimethylaminosuccinate amide, 2-isopropyl-4-trimethylammonio-5-methylphenylpiperidine-1- Carboxylic acid ester chloride, phenyl-isopropylcarbamate, 3-chlorophenyl-isopropylcarbamate, ethyl-2- (3-chlorophenylcarbamoyloxy) -propionate, maleic acid hydrazide, 2,3-dichloroiso Butyric acid, di- (methoxythiocarbonyl) disulfide, 1,1'-dimethyl-4,4'-bipyridylium-dichloride, 3,6- Endotoxinhexahydrophthalic acid, 3-amino-1,2,4-triazole

1,2,3-티아디아졸릴-5-일-우레아 유도체, 1-(2-피리딜)-3-(1,2,3-티아디아졸-5-일)-우레아1,2,3-thiadiazolyl-5-yl-urea derivative, 1- (2-pyridyl) -3- (1,2,3-thiadiazol-5-yl) -urea

2-부틸티오-벤조티아졸, 2-(2-메틸프로필티오)-벤즈티아졸, 3,4-디클로로이소티아졸-5-카복실산, 2,3-디하이드로-5,6-디메틸-1,4-디티인-1,1,4,4-테트라옥사이드, 아르센산, 카코딜산, 염소산염, 특히 염소산칼슘, 염소산칼륨, 염소산마그네슘 또는 염소산나트륨, 칼슘시안아미드, 요오드화칼륨, 염화마그네슘, 압시스산 및 노난올.2-butylthio-benzothiazole, 2- (2-methylpropylthio) -benzthiazole, 3,4-dichloroisothiazole-5-carboxylic acid, 2,3-dihydro-5,6-dimethyl-1 , 4-dithiin-1,1,4,4-tetraoxide, arsenoic acid, cacodylic acid, chlorate, in particular calcium chlorate, potassium chlorate, magnesium chlorate or sodium chlorate, calcium cyanamide, potassium iodide, magnesium chloride, absic acid And nonanol.

본 제제에는 1,2,3-티아디아졸-5-일-우레아 유도체로서 1-페닐-3-(1,2,3-티아디아졸-5-일)-우레아를, 기타 활성 성분으로서 S,S,S-트리-n-부틸-트리티오포스포르산 에스테르, 칼륨 또는 나트륨 클로레이트, 1,1,-디메닐-4,4'-비피리딜리늄 클로라이드, 2-부틸티오-벤즈티아졸, 2-(2-메틸프로필리오)-벤즈티아졸, 3,4-디클로로이소티아졸 5-카복실산 또는 2,3-디하이드로-5,6-디메틸-1,4-디티인-1,1,4,4-테트라옥사이드를 함유시키는 것이 유리하다.This formulation contains 1-phenyl-3- (1,2,3-thiadiazol-5-yl) -urea as 1,2,3-thiadiazol-5-yl-urea derivative and S as other active ingredient. , S, S-tri-n-butyl-trithiophosphoric acid ester, potassium or sodium chlorate, 1,1, -dimenyl-4,4'-bipyridinium chloride, 2-butylthio-benzthia Sol, 2- (2-methylpropylio) -benzthiazole, 3,4-dichloroisothiazole 5-carboxylic acid or 2,3-dihydro-5,6-dimethyl-1,4-dithiin-1, It is advantageous to contain 1,4,4-tetraoxide.

놀랍게도 본 발명에 따른 제제는 그 안에 함유되어 있는 활성성분 각각의 작용보다 훨씬 강한 식물성장조절작용을 나타낸다.Surprisingly, the preparations according to the invention exhibit a much stronger plant growth regulation than the action of each of the active ingredients contained therein.

본 발명의 제제는 특히 목화의 탈엽에 적합하며, 이것으로 인해 열매 수확시에 수확기계로 열매를 따기에 이상적이 되도록한다.The formulations of the invention are particularly suitable for defoliation of cotton, which makes them ideal for picking berries by harvesting machines at the time of fruit harvesting.

본 발명의 제제는 또한 그밖의 식물에도 성장에 영향을 주거나 또는 탈엽을 일으키도록 할 수 있다. 즉, 예를들면 목초의 저부에 위치한 싹에서의 곁가지 성장을 촉진하며 쌍떡잎식물, 특히 무궁화, 사과 및 기타 수목의 곁가지 형성을 촉진한다.The formulations of the invention can also cause other plants to affect growth or cause defoliation. That is, for example, it promotes the growth of side branches in the shoots located at the bottom of the grasses and promotes the formation of the dicotyledons, especially the leaves of green leaves, apples and other trees.

본 발명은 본 발명의 제제로 식물을 처리함으로써 생장하는 식물의 성장을 조절하거나 또는 탈엽시키는 방법도 제공한다.The present invention also provides a method of controlling or defoliating the growth of a growing plant by treating the plant with an agent of the present invention.

본 발명은 또한 작물을 본 발명의 제제로 처리함으로써 성장하는 작물의 성장을 조절하거나, 탈엽시키는 방법을 제공한다.The present invention also provides a method of controlling or defoliating the growth of a growing crop by treating the crop with a formulation of the invention.

원하는 탈엽작용을 일으키는 사용비율은 보통 헥타르당 활성물질 1 내지 10,000g, 특히 헥타르당 활성물지 10 내지 1000g의 비율이다.The rate of use which gives rise to the desired defoliation is usually from 1 to 10,000 g of active substance per hectare, in particular from 10 to 1000 g of active substance per hectare.

본 발명의 제제는 각각 원하는 목적에 따라 기타 활성물질, 예를들면 탈엽제, 식물보호제 또는 해충방지제 등과 함께 혼합하여 사용할 수 있다.The formulations of the present invention may each be used in admixture with other active substances, such as defoliants, plant protection agents or pest control agents, depending on the desired purpose.

그밖에도 유기용매, 습윤제 및 오일과 같은 약효증가용 첨가제를 사용하여 본 발명의 제제의 약효를 증가 및 촉진시킬 수 있다. 따라서 각각의 활성성분의 사용비율이 훨씬 감소된다.In addition, additives for increasing efficacy such as organic solvents, wetting agents and oils can be used to increase and promote the efficacy of the formulations of the present invention. Therefore, the use rate of each active ingredient is much reduced.

본 발명의 제제는 액체 및 또는 고체 담체 또는 희석제, 경우에 따라서는 습윤제, 점착제, 유화제 및 또는 분산제등의 한가지 이상의 계면활성제등을 첨가하여 산제, 분무제, 약제, 유제 또는 현탁제와 같은 제제의 형태로 만들어 사용할 수 있다.The formulations of the invention are in the form of preparations such as powders, sprays, medicaments, emulsions or suspensions, with the addition of one or more surfactants such as liquid and / or solid carriers or diluents, in some cases, wetting agents, tackifiers, emulsifiers and / or dispersants. Can be used to make.

적절한 액상담체로는 예를들면 물, 지방족 및 방향족 탄화수소 예를들어, 벤젠, 톨루엔 및 크실렌, 사이클로헥산온, 이소포론, 디메틸설폭사이드 및 디메틸포름아미드와 광유획분이 있다.Suitable liquid carriers include, for example, water, aliphatic and aromatic hydrocarbons such as benzene, toluene and xylene, cyclohexanone, isophorone, dimethylsulfoxide and dimethylformamide and light fractions.

적절한 고체 담체에는 예를들면 톤실, 실리카겔, 활석, 카올린, 아타클레이, 석회석, 이산화규소와 같은 토양광물 및 밀가루와 같은 식물생산물이 포함된다.Suitable solid carriers include, for example, tonsil, silica gel, talc, kaolin, atacclay, limestone, soil minerals such as silicon dioxide and plant products such as flour.

계면활성제로는 칼슘리그닌설포네이트, 폴리옥시에틸렌-알킬페닐에테르, 나프탈렌설폰산 및 그의 염, 페놀설폰산 및 그의 염, 포름알데하이드 축합물, 지방알콜 설페이트 및 치환된 벤젠설폰산 및 그의 염이 있다.Surfactants include calcium lignin sulfonate, polyoxyethylene-alkylphenylether, naphthalenesulfonic acid and salts thereof, phenolsulfonic acid and salts thereof, formaldehyde condensates, fatty alcohol sulfates and substituted benzenesulfonic acids and salts thereof .

이러한 여러가지 제제에서 총 활성성분의 비율은 넓은 범위로 변경될 수 있다. 예를들면 제제는 약 10 내지 80중량퍼센트의 활성물질과 약 90 내지 20중량퍼센트의 액체 또는 고체담체를 함유하며 경우에 따라서는 계면활성제를 20중량퍼센트까지 함유한다.The proportion of total active ingredients in these various formulations can vary over a wide range. For example, the formulation contains about 10 to 80 weight percent of the active substance and about 90 to 20 weight percent of the liquid or solid carrier and optionally up to 20 weight percent of the surfactant.

제제내의 각각의 활성성분의 중량비는 약 100 : 1 내지 1 : 1000, 바람직하기로는 10 : 1 내지 1 : 100이며 이 비율은 식물의 감수성 및 저항력의 정도, 사용시기, 기후조건 및 토양조건에 따라 변경된다.The weight ratio of each active ingredient in the formulation is about 100: 1 to 1: 1000, preferably 10: 1 to 1: 100, depending on the degree of plant sensitivity and resistance, the time of use, climatic conditions and soil conditions. Is changed.

제제는 통상의 방법에 의해 시용할 수 있다. 예를들어 물을 담체로 사용하여 약 100 내지 1000리터/헥타르 비율로 분무한다. 또한 본 제제는 "저용적법" "극소용적법"으로 사용할 수도 있다.The formulations can be applied by conventional methods. For example, water is used as the carrier and sprayed at a rate of about 100 to 1000 liters / ha. In addition, this formulation can also be used by the "low volume method" and the "small volume method".

상기 화합물이외에도 구조식(Ⅰ)의 티아디아졸 유도체로서 다음 화합물을 사용할 수 있다.In addition to the above compounds, the following compounds may be used as the thiadiazole derivatives of formula (I).

Figure kpo00002
Figure kpo00002

다음의 실시예는 본 발명을 설명한 것이다.The following examples illustrate the invention.

[실시예 1]Example 1

온실에서 7 내지 11엽단계 목화의 활짝 펴진 잎에 제제를 4번 반복하여 처리하여 일련의 실험을 수행한다. 헥타르당 500ℓ의 물에 사용되는, 혼합 성분 및 각 활성성분의 분량은 다음 표에 기재되어 있다.In a greenhouse, a series of experiments are carried out by repeatedly treating the preparation four times with the expanded leaves of the 7-11 leaf stage cotton. The amounts of the mixed ingredients and the amounts of each active ingredient used in 500 liters of water per hectare are listed in the following table.

처리한 14일후 떨어진 잎의 수를 확인한다. 이와같은 결과를, 처리하기 전에 존재하던 나무잎의 수와 비교해 볼 때 탈엽작용이 있음을 나타내고 있다.Check the number of leaves fallen after 14 days of treatment. These results indicate that there is defoliation activity when compared to the number of tree leaves that existed before the treatment.

또한 에스. 알. 콜비의 방법["Calculating Synergistic and antagonistic responses of herbicide combinations" Weeds, 15/1 (1967), 20에서 22페이지]에 따라 기대되는 각 활성성분의 상가작용인 값 E를 측정한다.Also s. egg. Colby's method ["Calculating Synergistic and antagonistic responses of herbicide combinations" Weeds, 15/1 (1967), pages 20 to 22] measures the value E, the additive behavior of each expected active ingredient.

계산방법은 각각 다음과 같은 공식에 의미한다.Each calculation method is represented by the following formula.

Figure kpo00003
Figure kpo00003

여기서here

X=A 제제의 탈염백분율(활성성분 p kg/ha)Desalting percentage of X = A formulation (active ingredient p kg / ha)

Y=B 제제의 탈엽백분율(활성성분 q kg/ha)Defoliation percentage of Y = B formulation (active ingredient q kg / ha)

Z=C 제제의 탈엽백분율(활성성분 r kg/ha)Defoliation percentage of Z = C formulation (active ingredient r kg / ha)

E=A + B제제(p+q kg/he) 및 A+B+C제제(p+q+rkg/ha)에 대한 탈엽 기대값.Expectation of defoliation for E = A + B formulations (p + q kg / he) and A + B + C formulations (p + q + rkg / ha).

만일 콜비식 방법에 의해 계산된 값 E보다 관찰된 값이 더 높으면 이 물질은 상승효과를 가진 것이다.If the observed value is higher than the value E calculated by Colby's method, the material has a synergistic effect.

[표][table]

Figure kpo00004
Figure kpo00004

[실시예 2-실시예 7]Example 2-Example 7

상기 실시예 1의 방법에 따라 목화를 처리한다. 결과는 다음 표에 기록하였다.Cotton is treated according to the method of Example 1 above. The results are reported in the following table.

Figure kpo00005
Figure kpo00005

[실시예 8]Example 8

목화를 상기 실시예 1의 방법에 따라 처리한다. 본 실시예는 상기 실시예 7 보다 훨씬 더 빈약한 일광 조건하에서 수행된다. 결과는 다음 표에 기술되어 있다.Cotton is treated according to the method of Example 1 above. This example is performed under daylight conditions that are much poorer than Example 7 above. The results are described in the following table.

[표][table]

Figure kpo00006
Figure kpo00006

[실시예 9-실시예 31]Example 9-31

상기 실시예 1의 방법에 따라 목화를 처리하여 다음 결과를 언는다.The cotton is treated according to the method of Example 1, and the following results are frozen.

Figure kpo00007
Figure kpo00007

Figure kpo00008
Figure kpo00008

Figure kpo00009
Figure kpo00009

[실시예 30-실시예 33]Example 30-33

상기 실시예 1의 방법에 따라 어린 무궁화 나무에 화합물을 처리하여 다음 결과를 얻는다.Treatment of the compound with young green tree according to the method of Example 1 above yields the following results.

[표][table]

[실시예 30]Example 30

Figure kpo00010
Figure kpo00010

[실시예 31]Example 31

Figure kpo00011
Figure kpo00011

[실시예 32]Example 32

Figure kpo00012
Figure kpo00012

[실시예 33]Example 33

Figure kpo00013
Figure kpo00013

Claims (1)

하기 일반식(Ⅰ)의 1,2,3-티아디아졸-5-일-우레아 유도체를 총활성 성분에 대해 10 : 1 내지 1 : 100비율로 지베렐린, S,S,S-트리-n-부틸-트리티오포스포르산 에스테르, 2-클로로에틸포르폰산, 1,1'-디메틸-4,4'-비피리딜륨 디클로라이드, 3,6-엔독소헥사하이드로프로탈산 나트륨염, 3-아미노-1,2,4-트리아졸, 1-(2-피리딜)-3-(1,2,3-티아디아졸-5-일)-우레아, 2-부틸티오벤조티아졸, 2-(2-메틸프로필티오)-벤조티아졸, 3,4-디클로로이소티아졸 5-카복실산, 2,3-디하이드로-5,6-디메틸-1,4-디티인-1,1,4,4-테트라옥사이드, 염소산염, 요오드화칼륨, 및 염화마그네슘 중에서 선택한 활성성분과 혼합시킴을 특징으로 하는 식물성장 조절용 조성물.The 1,2,3-thiadiazol-5-yl-urea derivative of the following general formula (I) is given in a ratio of 10: 1 to 1: 100, based on the total active ingredient, gibberellin, S, S, S-tri-n- Butyl-trithiophosphoric acid ester, 2-chloroethylphosphonic acid, 1,1'-dimethyl-4,4'-bipyridylium dichloride, 3,6-endoxohexahydroprotalate sodium salt, 3-amino -1,2,4-triazole, 1- (2-pyridyl) -3- (1,2,3-thiadiazol-5-yl) -urea, 2-butylthiobenzothiazole, 2- ( 2-methylpropylthio) -benzothiazole, 3,4-dichloroisothiazole 5-carboxylic acid, 2,3-dihydro-5,6-dimethyl-1,4-dithiin-1,1,4,4 A composition for controlling plant growth, characterized in that it is mixed with an active ingredient selected from tetraoxide, chlorate, potassium iodide, and magnesium chloride.
Figure kpo00014
Figure kpo00014
상기일반식에서 R1은 수소 또는 탄소수 1 내지 3의 알킬기이며 R2는 수소 또는 탄소수 1 내지 4의 알킬기이며 R3는 탄소수 1 내지 4의 알킬기, 탄소수 5 내지 8의 시클로 알킬기, 비치환 페닐기, 하나 이상의 할로겐으로 치환된 페닐기, 하나 이상의 메틸기를 치환된 페닐기, 하나 이상의 메톡시기로 치환된 페닐기 또는 하나 이상의 니트로기로 치환된 페닐기이며 X는 산소원자 또는 황원자이다.In the general formula, R 1 is hydrogen or an alkyl group having 1 to 3 carbon atoms, R 2 is hydrogen or an alkyl group having 1 to 4 carbon atoms, and R 3 is an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms, and an unsubstituted phenyl group. Or a phenyl group substituted with one or more halogens, a phenyl group substituted with one or more methyl groups, a phenyl group substituted with one or more methoxy groups, or a phenyl group substituted with one or more nitro groups, and X is an oxygen atom or a sulfur atom.
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