74115-24-5

Usage

Uses

Used in Agriculture:
Clofentezine is used as a miticide for the protection of a wide variety of crops, including fruit, cereals, rangeland, and ornamentals. It is classified as a U.S. EPA restricted Use Pesticide (RUP) and is effective in controlling mite populations, thus contributing to the overall health and yield of the crops.
Used in Ornamental and Food Crops Protection:
In addition to its use on a wide range of crops, Clofentezine is also utilized in the protection of ornamentals and food crops in the field. As a mite growth regulator, it helps maintain the quality and appearance of these plants by preventing damage caused by mite infestations.

Trade name

APOLLO?; OVATION?

Potential Exposure

Tetrazine miticide used on a wide variety of crops
fruit, cereals, rangeland, ornamentals, etc. An EPA Restricted Use Pesticide (RUP).

Shipping

UN3077 Environmentally hazardous substances, solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required

Incompatibilities

Oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); strong acids. Decomposes above 185°C

Waste Disposal

Do not discharge into drains or sewers. Consult with environmental regulatory agencies for guidance on acceptable disposal practices. In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers. Containers must be disposed of properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office.

InChI:InChI=1/C14H8Cl2N4/c15-11-7-3-1-5-9(11)13-17-19-14(20-18-13)10-6-2-4-8-12(10)16/h1-8H

Upstream product

• 74115-15-4 3,6-bis(2-chlorophenyl)-1,2-dihydro-1,2,4,5-tetrazine 
• 74115-15-4 3,6-bis(2-chlorophenyl)-1,4-dihydro-1,2,4,5-tetrazine 
• 873-32-5 2-Chlorobenzonitrile 
• 6830-78-0 3,6-diphenyl-1,2,4,5-tetrazine 
• 100-47-0 benzonitrile 

Downstream Products

• 1026774-68-4 1,4-bis(2-chlorophenyl)-6,7-dihydro-5H-cyclopenta[d]pyridazine 

Relevant academic research and scientific papers

PROCESS FOR PREPARING FUNCTIONALIZED 1,2,4,5-TETRAZINE COMPOUNDS

The present invention relates to a process for the synthesis of 3,6 functionalized 1,2,4,5-tetrazine compounds of formula (I); wherein A and B being the same; and wherein at least one of R1, R1', R2 and R2' and at least one of R10 and R10' is a halogen atom or acetate group; said process comprising reacting the corresponding 1,2,4,5-tetrazine compounds wherein at least one of R1, R1', R2 and R2' and at least one of R10 and R10' is a hydrogen atom with an oxidative reagent in presence of a catalyst.

Building Diversity in ortho-Substituted s-Aryltetrazines by Tuning N-Directed Palladium C-H Halogenation: Unsymmetrical Polyhalogenated and Biphenyl s-Aryltetrazines

We report a general route for synthesizing ortho-substituted unsymmetrical biphenyl and polyaromatic s-aryltetrazines. These compounds are inaccessible by classical Pinner hydrazine condensation or by the current s-aryltetrazine aromatic core functionalization methods described up to now. We exploited multiple versatile N-directed palladium C-H activation/halogenation of s-aryltetrazine to form C-X bonds (X = I, Br, Cl, F), which collectively produced polyhalogenated unsymmetrical building blocks. We achieved a sequence of selective C-H halogenation reactions in a specific order to produce reactive aryl halides. Polyhalogenated s-aryltetrazines can then be used for controlled cross-coupling reactions toward ortho-substituted polyaromatic s-aryltetrazines. In general, this C-H functionalization route gives access to a large number of variously halogenated building blocks practical for further synthetic implementation of tetrazines (arylation, cycloaddition, etc.). Herein, we exemplified their potential by using halogen-selective Suzuki-Miyaura reactions for divergent construction of novel biphenyl s-tetrazines. Therefore, we deliver original poly(hetero)aromatic tetrazine structures, such as new typically "Z-shaped" and "T-shaped" species. We examined by DFT calculation the origin of the remarkable regioselectivity in some C-H concurrent halogenation reactions. Computations focused at free enthalpy profiles for C-H activation of aryltetrazines to form the intermediate palladacycles by CMD process. We showed that the presence of halogen substituents on aryl groups before further halogenation increases the activation barrier to form the determining C-H activation intermediate palladacycle. XRD studies of functionalized tetrazines evidenced planarity ruptures in the mutual arrangement of aromatic cycles. Finally, this methodology allowed us to deliver a unique tetrahalogenated s-aryltetrazine holding not less than four different halogens arranged in ortho-aryl positions.

Ortho-Functionalized Aryltetrazines by Direct Palladium-Catalyzed C-H Halogenation: Application to Fast Electrophilic Fluorination Reactions

A general catalyzed direct C-H functionalization of s-tetrazines is reported. Under mild reaction conditions, N-directed ortho-C-H activation of tetrazines allows the introduction of various functional groups, thus forming carbon-heteroatom bonds: C-X (X=I, Br, Cl) and C-O. Based on this methodology, we developed electrophilic mono- and poly-ortho-fluorination of tetrazines. Microwave irradiation was optimized to afford fluorinated s-aryltetrazines, with satisfactory selectivity, within only ten minutes. This work provides an efficient and practical entry for further accessing highly substituted tetrazine derivatives (iodo, bromo, chloro, fluoro, and acetate precursors). It gives access to ortho-functionalized aryltetrazines which are difficult to obtain by classical Pinner-like syntheses.

ACTIVE COMPOUND COMBINATIONS HAVING INSECTICIDAL AND ACARICIDAL PROPERTIES

The novel active compound combinations comprising a compound of the formula (I-1) or (I-2) and the active compounds (1) to (26) listed in the description have very good insecticidal and acaricidal properties.

Synthesis, structure analysis, and antitumor activity of 3,6-disubstituted-1,4-dihydro-1,2,4,5-tetrazine derivatives

Fourteen compounds of 3,6-disubstituted-1,4-dihydro-1,2,4,5-tetrazine derivatives were prepared and their structures were confirmed by single-crystal X-ray diffraction and the semi-empirical calculation of PM3 method. This reaction yields the 1,4-dihydro derivatives rather than the 1,2-dihydro derivatives. The central six-membered ring of 1,4-dihydro-1,2,4,5-tetrazine has a chair conformation and therefore is not homoaromatic. Their antitumor activities were evaluated in vitro by SRB method for A-549 and BEL-7402 cells, and MTT method for P-388 and HL-60 cells. The results show that there is one compound which is highly effective against P-388 cells and one compound which is highly effective against HL-60 cells. So it is a kind of compound which possesses potential antitumor activities and is worth to research further.

Synthesis and antitumor activity of s-tetrazine derivatives

Fifty-five compounds of s-tetrazine derivative including hexahydro-, 1,6-dihydro, 1,4-dihydro-, 1,2-dihydro- and aromatic s-tetrazine were prepared. Their antitumor activities were evaluated in vitro by MTT method for P-388 cell and SRB method for A-549 cell. The results show that there are 9 compounds which in 10-6 μM have more than 50% inhibition rate to A-549 cancer cell growth, and 7 compounds in 10-6 μM have more than 50% inhibition rate to P-388 cancer cell growth. The IC50 of compound 3q for P-388, Bel-7402, MCF-7 and A-549 are 0.6 μM, 0.6 μM, 0.5 μM and 0. 7 μM, respectively. So s-tetrazine derivative is a kind of compound which possesses potential antitumor activities and is worth to research further.

Use of citric acid derivatives as pesticidal adjuvants

The invention provides the use as a pesticidal adjuvant of at least one citric acid derivative and compositions containing the derivative, which has a log octanol-water coefficient (log P) of 2.6 to 11 and an equivalent hydrocarbon (EH) value of 29 to 47. The invention has been shown to enhance the efficacy of a range of pesticides.

Insecticidal compositions and methods of use employing imidacloprid and another insecticide

The present invention relates to insecticidal mixtures of chloronicotinyl insecticides of the formula (I) STR1 in which R1 represents C1 -C5 -alkyl, R2 represents hydrogen or C1 -C5 -alkyl, or R1 and R2 together represent --CH2 --CH2 --; --CH2 --CH2 --CH2 -- or STR2 X represents an NH group, NCH3 group or represents sulphur, Y represents nitrogen or a CH group and Z represents cyano or nitro, with one or more of the synergists mentioned in the description.

Acaricidally active tetrazine derivatives

The invention relates to novel 1,2-dihydro-1,2,4,5-tetrazine derivatives of the formula (IV) STR1 wherein means fluorine, chlorine or bromine; and Y stands for hydrogen or fluorine, as well as to a process for the preparation thereof. The compounds according to the invention have acaricidal, larvicidal and ovicidal effects.

Macrocyclic plant acaricides

Compounds of the formula I STR1 in which either R is methyl and there is a double bond in the 9,10-position, or in which R is hydrogen and there is a single bond in the 9,10-position, are highly active against Acarina which damage plants.